Her Son's Best Friend
This starts slowly. It is a story about domination and control, before it is a story about sex. It is in two parts, with the second part to come soon. It is mostly written.
Caroline Barron was an impressive, majestic woman. At 5'11" and 160 lbs with long red hair, she commanded any room she was in. It was a good thing, too, because as a mother forced to raise a son on her own, it helped reinforce her authority. Raising Doug was always going to be a challenge, the more so since he had a lot of his father in him. He, too, was tall and athletic, and girls swooned over him. The same girls did not seem to have much of an eye for Gary, Doug's best friend, and that suited Caroline just fine because she decided she would have Gary herself.
For as long as Caroline could remember, she enjoyed sexually dominating the men with whom she had relationships. As her boyfriends of the time would attest, she was a natural. Yet, when she graduated college and her sights were set on building a career and getting married and having a family, that ardor cooled somewhat. As a result, she ended up marrying a man with whom she would play rope and bondage games from time to time but also alternating control. When Caroline took time off from her career to raise her son, her desire to sexually dominate her husband rose greatly while Doug was a toddler and, as a result, her marriage collapsed. Caroline didn't mind being home as a housewife and mother, but it had the perverse effect of wanting to dominate more in the bedroom because she had less control outside of it. Conversely, her husband's career, for which Caroline had sacrificed much, was blossoming but his idea of fun wasn't to come home and supplicate on his knees at night when so many beautiful young things were throwing themselves at him at work.
By the time Doug was nine and Caroline 31, she was divorced. She received a nice settlement, courtesy of her husband's stock options, and regular alimony. Rather than restart a career in a town where her husband was thriving, Caroline moved herself and her son to the outskirts of a city several hundred miles away. She didn't need to work full-time, but found a satisfying job with a non-profit that allowed her to use her skills and keep to school hours to care for her child.
From the beginning, Caroline always thought Doug's friendship with Gary peculiar. They were opposites in many ways. Doug was outgoing and athletic, while Gary was neither. Still, they became fast friends and stayed that way to the present day. Years later Doug would explain to his mother that at the new school when they had first moved, Gary was the only child for a long time who would be friends with the "new kid." It was something he never forgot and would never forget. And through the years, the boys helped each other. Doug grew tall and athletic like his mother and father, smart but not brilliant, weak at math. He was popular and well-liked. Gary's growth stopped at 5'8'. In high school, he was not overly nerdy, though much more bookish than Caroline's son. Ordinarily he might have been a regular target for rough treatment at the hands of the school's athletes, but everyone knew about Doug's friendship with Gary and no ever tried anything with him, at least not for very long. Gary, for his part, year in and year out, helped Doug with math. With Gary, Doug was a B-student. Without him, C or D. Gary spent many early evenings, after Doug's daily sports practices, tutoring his friend in math.
Although Caroline dated new men in the new city, she did not develop any lasting relationships. Caroline dominated in most of those relationships but none were especially satisfying, many of the men actually too needy emotionally.
Gary was 15 when the thought first crossed Caroline's mind that she could dominate him, physically and sexually. He was a cute young man, wiry, not buff, always polite with a seemingly eager-to-please personality. She quickly put it out of her mind, however, scolding herself for thinking about actions that were frankly illegal. At 16, Caroline thought Gary was gay, in light of the fact he never mentioned or talked about girls. When she finally raised this possibility with Doug, he assured his mother that Gary indeed liked girls and was not gay. "Just because he doesn't go on about the cheerleaders in front of you, that doesn't make him gay, Mom!" The truth was that he was simply too shy to try very often to go with out girls and the couple of times he tried, it hadn't worked, Doug told his mother.
When Gary was 17 at the start of their senior year in high school, Caroline decided she wanted Gary, that she wanted to dominate him completely and make him her sex slave. If she did this right, she thought, he would be devoted to her by the time he turned 18 in January and, then, he was fair game to make her conquest of him complete.
Caroline was actually a little surprised at herself, at the fact that her mind was turning in the direction of wanting her son’s best friend, a 17-year old boy. But on the other hand, why not? She had no intentions of doing anything truly serious with him until he was of legal age. It was her age and maturity, unlike the girls of Gary’s age, that saw in him numerous things that they were missing. He was not unattractive, he was a nice and polite young man, he was clearly going to be eager to please and malleable. Unlike some 40-year old male, even a submissive one, she would be able to mold the virginal teenager into her ideal lover. And what is more, she knew that once she was able to take him completely, his age meant he was almost certainly energetic enough and having the stamina to keep up with her demands.
The question was: how to do it? It had been some time since she had tried to seduce someone and two lives ago since she had tried to seduce a teenager. The first step, prior to the start of Doug’s and Gary’s senior year was to simply look attractive and sexy when Gary was around, expecting him to notice her and at least get his mind to think from time to time how great it would be to have her. This was not hard to do. The summer permitted shorts, halter tops or tight t-shirts, and pumps which accented her already long, attractive, and shapely legs. This worked. She noticed Gary's lingering stares at her from time to time, although the guys were always doing things, so he didn't spend much time in her presence for long. Still, it was a start.
Once school began, Gary spent more and more time around the Barron residence, helping Doug with his math, routinely three days a week after sports practice was over, not counting time they spent together on the weekends. It was not unusual for Gary to spend eight hours at Caroline's house during the week, as he often showed up before Gary arrived home on the late bus. It was in those moments, when she and Gary were alone, that Caroline slowly began to reel him in.
At first she would just chit-chat with him, about anything really, often doing things that kept his clearly interested face focused on her sexy body. She wanted to make it easy for him to look at her. Over the course of a couple of weeks, she had numerous encounters with Gary like this, always dressed sexily and revealingly---but not too much. Caroline began to work into her interactions with Gary many small touches and brushes with her hands, legs, and breasts. And the more she did of this, the earlier Gary was showing up at her house. At first, he had been only 15 minutes before Gary came home, but at the end of three weeks of this treatment, Gary was showing up almost an hour early, even volunteering to help Caroline with anything she needed help with.
One day she decided to steer the conversation towards sex. "So, Gary, why is it you don't have a girlfriend, instead of hanging around an old lady like me? Lord knows Doug seems to have a steady stream of them!"
Gary turned red a bit at this unexpected turn in the conversation. "Well, uh, I, uh, don't know. I'm not very good at talking with them beyond school stuff. I'm a little shy, I guess, and girls don't seem to like shy."
"Really," Caroline replied. "I've always found it rather cute myself." Gary turned redder at this statement but she doubted he knew it. "You have many desirable qualities, Gary. You're smart, you're loyal, you're kind, you're a handsome young man!. It would seem to me that that is a winning combination."
Gary's embarrassment grew at the sound of these words, yet inside he loved hearing the flattery. However, he was a little embarrassed to find himself growing a rather strong erection and made some effort to hide it from Mrs. Barron. He was not completely successful. By now he had had a number of sexual fantasies with the mother of his best friend in mind, especially at home and in bed, so hearing her say those things about him kindled them again. "Uh, well, thanks. That's nice of you to say but frankly the girls favor Doug's type: you know, tall, good-looking, athletic. It is actually kind of unappealing to see so many of them throw themselves at the jocks."
Gary decided to try to regain some control of the situation and turn the tables. "So, why haven't you remarried or dated more?"
Caroline was actually surprised at Gary's boldness in asking the question but quickly turned it around. "Yes, well, that is a fair question, I guess, after what I had said. Many of the men I meet are either too overbearing and macho or too needy, looking for a mother to take care of them. Bleahh! And so long as man is physically fit, seems to care about himself, I don't care if he is shorter than I am. No, if I really wanted to be with someone, I would look for someone with your qualities, Gary: smart, loyal, someone who respects women, and is easy to get along with."
Gary's eyes were glued to Caroline's body as she said those things about him again. The look of lust in his eyes was apparent and he was still trying hard to cover his clearly larger erection. Gary laughed a nervous laugh. "Well, I guess then it's too bad I'm not a few years older because I would love to date someone like yourself!"
Caroline saw her opening and decided it was the moment. Gary wouldn't be home for 40 more minutes. Caroline walked over to Gary, who was seated at a stool on the island in Caroline's kitchen. Wearing her four-inch heeled boots, being taller, and the fact that Gary was seated on a stool, Caroline was a head taller than he was. Swiftly she unbuttoned the tight white silk shirt she has been wearing, exposing to Gary's bulging eyes her large, slightly sagging, but utterly beautiful and braless breasts. Because of the exaggerated height difference, those breasts were positioned right at Gary's face. "Go on, Gary, suck them. I know you want to," Caroline said huskily. At first Gary didn't move. His mind was reeling from this wholly unexpected development, this fantasy coming to life. Exceedingly slowly, as if he was making sure he wasn't in a dream or Caroline wasn't going to change her mind, Gary closed in on the first nipple, mouth open, as if he were about to receive the most succulent treat of a lifetime, which for him it was. Once his mouth connected, however, he began to lick and suck hungrily. First one breast then the other. Then back again. Finally, Caroline said, "Come with me." And Gary eagerly followed her to her bedroom, but as they walked, her hand firmly grasping and pulling on his, Caroline said, "Don't get overly excited, Gary. I can't make love to you, not yet, you're under age. It would be illegal." The look of disappointment on the boy's face was measurable.
"I wouldn't tell anyone!" Gary blurted out.
"I am sure you wouldn't but mistakes are made, things are discovered. Look, it is three months to your 18th birthday, we can wait until then and still enjoy each other's company in the meantime," she answered, as she drew him into her bedroom and sat Gary down on the bed.
Crazed with lust, but almost pouting with frustration, Gary asked, "then why did you allow me to touch your breasts and why are we in your bedroom?" His face seemed confused and yet hoping she was saying one thing while doing another.
"I said we can enjoy each other's company, and we can. It can include, I think, you worshipping my breasts more, but you must do as I say, and you must exercise some self-discipline and control. It can involve some nudity on your part and pleasure, but do not attempt to push this further than we can. If you do, there will be consequences. Okay?"
Disappointed but anxious to spend more time with this goddess before him, Gary replied: "okay."
Smiling broadly---it was going so well---Caroline said, "Very good. Now. When we are together and alone, I want you to call me 'Mistress.' It's a sign of respect for me and you must promise to do as I say. Also, go ahead and strip."
"Yes, mistress," Gary replied a little uncertainly and proceeded with a full blush Caroline found adorable to strip down to his underwear.
"Take it all off." And Gary took off the last vestige of his privacy, presenting the sight of a naked teenage male before a fully clothed, if open shirted, tall, beautiful woman. His cock had been hard but was now a little limp from his initial embarrassment. She then laid Gary back on the bed, while sitting beside his naked form, and began kissing him aggressively on the mouth. Her tongue forced its way into his mouth, dominating it, exploring every corner, which he accepted. While doing so, she gently rubbed her breasts in a small circling motion against Gary's own chest and nipples. His penis returned almost instantly to a rock-hard state. Caroline also stroked the boy's body with one hand, up and down the side of his chest and leg. This went on for quite some time, with Caroline deliberately making Gary hotter and hotter, knowing he would soon do something he shouldn't.
Sure enough, Gary's arms, which had been around Caroline's chest as she kiss-tortured him, moved down to her skirt and made a slight attempt to take them off. Gary hoped that perhaps Caroline would be carried away in the excitement of their activities and take things further. Little did he understand how much Caroline had hoped he would try but not for the reasons he imagined.
"STOP!" she shouted and slapped Gary on the face. "I told you there would be none of that, for now! I told you, you must do as I say! I told you if you didn't there would be consequences! Didn't I!?"
Fearful that he had blown the best thing that had happened to him with woman so far in his life, Gary meekly replied, "yes...mistress. I'm sorry, it won't happen again! Please, I just want to continue to be here with you!"
Thrilled to hear him begging to stay, Caroline pressed her advantage as she intended. "Sorry isn't going to be good enough, Gary. I said there would be consequences. I'll give you a choice: you can leave and we would never do this again or" --- and Caroline paused for a second for effect--- "you can be spanked for being the naughty boy that you are!" Caroline did not doubt for a minute what Gary would choose. His cock had weakened again at this fear of what he had done, but otherwise it has been completely stiff all the time they had been together.
"I, I'll take the spanking," Gary answered quietly.
Caroline sat up on the bed and pointed to her lap. Gary got up and crawled over and laid himself down in the ancient spanking position of young children. Caroline grabbed Gary's arm, pulling it painfully behind and up his back, and began spanking with the other hand.
However, it was unlike any spanking Gary remembered as a child. Those had been hard and fast and soon over. Caroline was going less hard at first, slowly, rubbing his bottom after each blow, scolding him along the way. By the tenth spank, Gary's bottom was red and he was pleading her to stop. Yet, the more he begged, the more excited Caroline became. By the 20th blow, Caroline stopped, Gary's eyes were watery, and said over and over loudly, "I'll behave, I promise, I won't do it again! Please stop!' She enjoyed it so much she had a small orgasm, although he didn't know that.
Once she let Gary up and he had wiped his eyes, she said, "lay back down and we will begin again." Surprised, Gary gingerly laid down on his back again, and Caroline started kissing him again, and rubbing her breasts against his chest. After doing this long enough to be convinced Gary wouldn't try anything he shouldn't, she moved her breasts again to his mouth. "Pleasure yourself, Gary. I told you there would be pleasure in this for you if you could behave. But don't let yourself cum until I say you can."
Gary was rock-hard again and could have come in seconds if he wanted to, but he stroked himself lightly enough to prevent that from happening. So lightly, at one point Caroline asked if he was obeying her, and he assured her he was, explaining he would come too soon otherwise. Finally after almost 15 minutes of this sensual torture, Caroline ordered: "Cum now, Gary! Fast" The boy immediately trebled his rate of action and brought himself to the best masturbatory orgasm of his life. Once completed, Caroline scooped up a healthy amount of cum on two fingers and put them in front of Gary's mouth. "Suck my fingers clean." Hesitating only a moment, he did so.
"There now. Was that not fun? Did you not get everything I promised?"
"Yes, Mistress."
"Very good. Well, Gary, this is what I have to offer, for now. We can either forget this all happened today or do more of it as the opportunities allow us. It must be between us alone. No one else must know and certainly not Doug. Am I clear? Any hint of this at any time and it's over."
"I would like nothing better than to continue with you---Mistress. I'll never breathe a word about it."
"Excellent. But just to make sure we are clear as to where this is headed. You are here to help me, to do as I say, completely. In effect, my young friend, I intend nothing less than to make a slave out of you when we are together. There will be a lot of pleasure for you, but a lot of service, too. And discipline, because I sense you are going to need it and I, frankly, find it very amusing to discipline young males. Doug has gotten too big for it, but you I think can take his place."
Turning red of embarrassment of the implied mention of his relative stature to Doug and to her, Gary answered with a mouth as dry as desert, "yes mistress." He was at the moment excited and infatuated with this sexy, mature woman, the mother of his best friend. He wasn't sure what it was going to mean to be a "slave" when he was with her, but if it was anything like today, he was all in favor of being completely enslaved. The thought of submitting and obeying one of the girls he lusted after at school did not come quite as easily as the thought of being this beautiful woman's boy-slave. It was actually quite exciting as he swelled to the various imagined activities.
When Gary got home that evening, after helping Doug, who had arrived home a scant eight minutes after Mrs. Barron had told him to get dressed, he greeted his mother who was there as always. "Oh, Gary," his mother said after he came through the door, "Mrs. Barron called." Gary froze, inside in a state of panic. "She simply wanted to compliment me, and you, for being a well-behaved guest in her house---although she did not mention you briefly acted up for a moment and then settled down after a minor scolding. (Gary involuntarily rubbed his behind.) But she said very nice things about you. Now, you make sure you keep doing what you were doing today. And when you are there, do as Mrs. Barron says. It's nice to hear nice things said about you."
Gary just grinned, partly at relief. "I'll be down for dinner in a few minutes. I just have to use the bathroom first." Gary ran upstairs, shocked that Mrs. Barron would make any oblique reference about what happened today to his mother and yet unbelievably excited at this twist to her game. It took him only a minute to masturbate to an orgasm again behind the locked bathroom door.
The Second Time
Two days later, Gary was due to meet up with Doug at his house again to help with that day's math lesson. Doug typically got home on the sports late bus at 5:30. Gary, however, headed straight to Doug's house after he left school at 3:30. When he arrived, he let himself in as he usually did and Mrs. Barron came out from the kitchen to greet him, wearing the same black silk bra, but with black spandex pants, and the same heeled ankle boots as two days earlier.
"Gary, it's good to see you. How was school?" And before he could answer, she swooped over him, grabbed his head and planted her full, luscious lips on his and began deeply kissing Gary. They pulled each other into a tight embrace and Gary's now surging erection could be felt by Caroline against her leg. "Happy to see me, I see," Caroline laughed.
"Yes, Mrs. Barron---I mean, yes mistress!"
"Good boy!" Caroline smiled at her young friend. "Let's go up to the bedroom, shall we? I want to continue where we were." As they entered the bedroom, Caroline ordered: "Strip." Gary knew this time that it meant everything and so it all came off. Standing seven inches above him in her heels, Caroline ran her hands all over Gary's smooth, virtually hairless body. "You are a handsome young man, Gary. I get wet from excitement just thinking of all delicious things we are going to do together in the coming weeks and months," she whispered in his ear, a full erection bobbing ever so slightly at every other words. "But let's repeat some of last time. I call it conditioning." Caroline opened the top four buttons of her blouse, pulling the material aside, letting her braless breasts fall out. She once again drew Gary's mouth to them, ordering him to worship again.
After 15 minutes or so of this, Caroline laid Gary back on the bed again and began to kiss him, passionately and with control. But rather than let Gary embrace her as she had the first time, she pinned his wrists to the bed, arms stretched out. Gary could hardly the stand the raging erection he was having. He desperately wanted relief but knew that he dare not do anything Caroline did not order him to do.
"You're a good kisser, Gary," Caroline told him after some time. "I very much enjoy it. I must also say you are doing a very good job with that talented mouth of yours in worshiping my breasts. I look forward to your 18th birthday and seeing what else you’re capable of with your tongue!' Gary flushed red in embarrassment, guessing what Mrs. Barron had in mind, and not really sure what he thought of it.
"I want you to get up now and come brush my hair." Caroline got up from her sitting position on the bed and walked over to the chair at her cosmetics desk and mirror. She motioned Gary to follow her. She sat down and unleashed her long red hair from its tight bun and handed a brush to Gary, who now stood behind her, as she watched him in the mirror, with his powerful erection unabated. Gary wasn't sure where this was all going, he only knew for sure that he found Mrs. Barron enormously exciting and that if she wanted him to brush her hair, he could certainly do so. For a hundred strokes he brushed her hair as they made idle chit-chat about school, life, Doug, or other subjects.
"Lovely," Caroline said once Gary has finished. "Time for your reward." She stood up and guided Gary by the arm back to the bed, his hard-on unabated during his caressing of her long, silky, red hair. "Now, lay down and pleasure yourself, Gary, but do not come until I tell you that you may. Stop if you must to prevent yourself from cumming." Gary began to stroke his cock, slowly, because he was far too excited to hold back for long once a little friction was applied. Repeatedly, he would stop for a while as he felt his eruption build and waited until it subsided. It did not help matters that Caroline frequently caressed the boy's arms and chest while he did so, further adding to his sexual tension, which of course was exactly what Caroline had in mind.
Finally, Caroline ordered him: "Beg me for it, Gary, beg me to give you permission to come."
Gary didn't need to be told a second time. "Please, please, Mistress, please let me cum! I beg you to let me cum!"
The sounds of genuine desperation in Gary's voice and the begging made Caroline quite wet. She, too, was ready for some relief. "Very well, Gary. But you must do exactly as I say. First close your eyes." After Gary had done so, Caroline leaned over and pressed her breasts down on Gary's face, making it rather difficult for him to breath and impossible to open his eyes. "Do not suck. But make yourself come! NOW!"
As Caroline clutched Gary's head with one hand, pressing his face into her buxom, she fingered herself with the other inside her pants. Meanwhile, Gary feverishly applied his own hands to his penis, bringing an explosion of cum within just a few seconds. Just as his was ending, Caroline came as well, though she managed to keep herself quiet and Gary, of course, was in no position to see a thing.
Once they were all cleaned up and Gary had put his clothes back, Caroline embraced the boy once more. "Wonderful. A wonderful afternoon, Gary. I look forward to next time. I’ll see you in a couple of days, again?"
"Yes, Mistress. We have a math test on Friday, so I plan to come over Thursday to help Doug study for it."
"Lovely. One other thing, however. Do you masturbate when you are home and alone in bed?"
Gary's face reddened at the question, but he saw no reason not to give a truthful answer. "Uh, yes ma'am."
"Am I now the object of your fantasies as you pleasure yourself?"
"Uh, well, yes Mistress, I confess you are."
"Don't be shy or embarrassed about it, Gary. I love the idea. I wouldn't want or expect it any differently. We have something very special going right now and with the promise it will soon get much more wonderful and special. However," and Caroline gave a long pause for effect, "you have a cell phone do you not?"
"Yes, ma'am," Gary answered, quite unsure where this was leading.
"Good. From now on, when you are home in bed, at night, desiring to jack-off, I want you to call me on my cell phone for permission. We will do it together over the phone. Starting tonight. I know you will want to cum again tonight. Most boys your age cum two or three times a day. Gary certainly does, although he has no idea that I know that."
Gary didn't think he wanted to know how she knew that either and made no comment. "But does that mean if you don't answer the phone, I cannot do it?" he asked apprehensively.
Caroline gave him a smile and the twinkle in her eye suggested that she was considering this, but: "No, if I do not answer, you may assume you have permission. If you were 35, I would have said yes, but since you are 17, I have no desire to drive you crazy, at least not yet. But I expect a call every time, regardless. Are we clear?"
"Yes, ma'am," Gary answered with relief. "We'd better get downstairs, Doug will be here soon." As Gary turned to leave the room, Caroline game him a hard smack on his butt.
That night, as he settled into his bed to bring himself off, he got out his cell phone and called his Mistress, feeling a degree of excitement and infatuation he had never felt in his life.
"Hello?"
"Uh, Mrs. Barron? It's Gary."
"Well, I know that from the caller id."
"Uh, right. Well, I'm in bed and I was wondering if I have permission to cum?"
Caroline, who herself had now settled in bed to watch TV as Doug played some video games in the basement, could not believe how instantly excited she became when Gary called. The sense of excitement, thrill and above all power that was coursing through her in this new relationship with her son's best friend was an aphrodesiac she had not experienced before. "Yes, my young slave," deliberately using that term on the phone, "but do not cum without final permission. I intend to listen."
As Caroline heard the rustling on the other end of the line and heard Gary's breathing become more labored, she fingered herself, actually coming before he did. "Don't forget to beg for it, Gary." And several times Gary begged to be allowed final release, moaning into the phone loudly when she finally said yes.
"Good night," and Caroline hung up.
The Third Time
On Thursday, prior to Gary's arrival that afternoon, Caroline went shopping at one of the sex shops downtown in the red light district. The relationship with Gary was going far better than she had dreamed. But when she thought about it, why wouldn't it? She was a sexy, attractive, available older woman. Teenage boys have been having fantasies about such women for time immemorial. Especially ones like Gary, who did not fair well with girls his own age. And why was that, anyway? Perhaps it was her age or maturity, but she saw many fine qualities in Gary and did not understand why young girls wouldn't be interested in him. I suppose he is not what they would consider hip or cool, she thought, but this was hardly the first instance in which woman of her generation would not understand the woman of the younger generation. Their loss, she thought. Gary is my delicious toy and I intend to play with him for as much and as long as I can.
While Caroline owned a number of leather or fetish garments, which she would start wearing when she and Gary were together, she wanted a couple of small items. One was a black leather collar and a long metal leash. Caroline had always been turned on by the thought or image of men in collars and leashes held by strong, powerful woman. Gary would have to submit to that now. And the other was a sex toy. She was going to need all the time between now and his 18th birthday to train Gary in some degree of self-control. It is probably and impossible task, for a 17-year old, but she was going to have fun trying in any event. But the toy was for a little later.
When Gary arrived that afternoon, he virtually burst into Caroline's house. It's a good thing he has been doing this for years, she thought, or some people might get suspicious. Caroline had on a white robe today, but underneath she was wearing leather boots, skin-tight leather pants, and a leather vest that revealed a satisfying amount of her ample cleavage.
"Hi Gary," Caroline called when she heard the door slam.
"Hi Mrs. Barron, I mean, hello Mistress," Gary said as he walked into the kitchen and found himself looking at a white robe.
"I was thinking," she started, "that you are probably wondering what exactly I meant when I said you would have to be my slave." The look on Gary's face told her she was right. "Well, as you can imagine from Tuesday, you have to do what I tell you to do---or not do something you want to do because I said you shouldn't. I like control, Gary, I like to control the men in my life. It's exciting. It is my greatest thrill. So you will do the things I tell you, when we are alone together, you will even start cleaning for me, but I doubt you will find that unpleasant as you will have to be nude and under my close and watchful eye." Caroline smiled at her boy-slave, expectantly.
"Uh, yes, Mistress. I want to do anything you want me to do." In saying that, Gary meant it with the bottom of his heart.
"Wonderful! Now, we both must look the part. If I am to be your dominant mistress, then I need to look something like this," and Caroline removed the robe as she walked from around the counter to stand in front of Gary. Her image took Gary's breath away. Above all, it was the skin-tight leather pants, which Gary suddenly and desperately wanted to feel with his hands. "Take off your clothes, Gary, now."
As he did so, Caroline pulled at the brown bag she had left on the counter. Once Gary was naked she told him to get down on his knees, taking out of the bag, the leather collar and metal leash. Gary turned beet red as she put the collar on her slave, which Caroline never failed to find exciting. After all, giving embarrassment to her young friend was a form of control. She only wished she had opportunities outside of the house to do that. "There! Now you look the part as well." And Caroline had Gary crawl over to the hall mirror where they both looked at both their images and both became excited at what they saw: an older, mature, but incredibly sexy woman in black leather holding the leash of a collared teenage male on his knees before her.
"Bend down, Gary, kiss my boots." He hesitated only a second, now quite used to doing as Mrs. Barron told him to do. He kissed her boots over and over. "Now lick them, Gary, until I tell you to stop." And Gary did so, first working the right boot and then the left. "Wonderful. Come. You may stand. Let's walk upstairs." Caroline led Gary by the leash to her bedroom. She sat in her chair, motioning Gary down on his knees again. "Take off my boots." Gary carefully undid the laces, finally freeing Caroline's feet. "Make yourself comfortable Gary, because you are going to give me a pedicure." For the next 40 minutes, Gary did that, following Caroline's detailed instructions, finally finishing with applying bright red polish, the whole exercise he found surprisingly erotic.
"You have actually done a creditable job, Gary for your first time. I almost feel bad about what happens next." Gary looked alarmed at first, thinking something really bad was going to happen. "Time for your next spanking."
Gary was partly relieved but also a little petulant. "But I didn't do anything wrong! I have behaved myself!" he pleaded.
"Well, that's true, up until that little tantrum right there. But you forget my young slave, I really enjoy disciplining young men. I almost felt guilty when Doug would get a spanking as he grew up, because I secretly enjoyed it so much. Now, however, there isn't the slightest trace of guilt. This is purely for my pleasure."
So again Caroline made Gary crawl on to her lap, pinning his arm and clamping his penis between her leather-clad thighs. The strokes that Caroline administered were as erotically delivered as before, even more so. She noticed this time, however, that Gary wasn't growing any softer, if anything, his hard-on was become more hard. And she realized that with blow, Gary's body twitched some, and his penis rubbed between her firmly clamped thighs. She knew it was exciting him, even if he found the spanking uncomfortable. She decided to proceed to see what would happen. By the ninth or tenth stroke, Gary spoke up.
"Mistress, I am going to cum!" Caroline was thrilled. Gary was about to come while being in one of the most humiliating positions a young male could be in, while still suffering some moderate pain. Rather than stop, however, Caroline said: "Oh really, you like this, do you?" It was more of a statement than a question and she did not expect Gary to answer. He didn't, in large part because she deliberately picked up the pace of her strokes and thus the rubbing of Gary's cock. In three or four more spanks, Gary's breathing increasing, finally saying, "oh, God, Mistress, please, ah, AAAHHHHHHHHHH," cumming violently inside Caroline's thighs. Once he finished, Caroline spanked a few times more, especially hard.
"Get up, Gary, and clean up this mess," Caroline finally announced. "With your tongue." And Gary got down on his knees and licked all of his cum off his Mistress's leather pants and a little that had gotten on the bed.
"I hope you enjoyed that!"
"Oh, yes, Mistress, thank you."
"Well, now is the time pay. I want some fun, too." Caroline laid Gary back on the bed, undid her leather vest, pinning Gary's arms, kissing him and having him suck her breasts. Then she repeatedly smothered Gary's face with her bosom, denying him air repeatedly for up to 90 seconds at a time. The utter control she felt, and she knew by now that the control was quite real, for she was clearly stronger than Gary, as well as having the weight advantage over him, was a complete aphrodesiac. Finally, she had Gary cover his groin with his arm, which allowed her to grind herself to an orgasm on it and prevent Gary from being stimulated to another himself.
For her part, Caroline at times could barely stand the wait herself and several times nearly succumbed to the temptation to fuck Gary during their playtime together. But she resisted. She wanted to wait, both for legal reasons, and the torment it was causing Gary. It excited her to see him so desperate to have her, yet be constantly denied.
The Device
When Gary arrived at the Barron residence the following week, Caroline explained a new conditioning program.
“Do you see this device, Gary? It’s tube with pump designed to excite men. It fits over your cock and is designed to simulate a woman’s pussy. We are going to start practicing with this so you do not cum so quickly. When you are 18, I want you to last for your first time.” For the next hour and for the next several months each time they were together, Caroline would force Gary to practice holding back his orgasm. It usually did not work.
The Birthday
On his 18th birthday, Gary could barely stand to wait for school to come to an end that day. Nevertheless, when it let out, he played it cool, told Doug he'd see him tonight and headed on his way to Doug's house. He called out as he usually did when he closed the door behind him. As he walked past the doorway to the living room, he did not see Caroline standing there to the side out of eyeshot. She immediately stepped into the hall and grabbed Gary quite firmly around the neck with her left arm. She was wearing long black leather gloves. "Happy Birthday, Gary," she whispered into his ear. "I've waited for this day for ages." As she said this, Caroline ever so lightly stroked Gary's face and arms. She moved her hand down to Gary's crotch and felt his hardness. "Oh, you're happy to be here, too?"
"Yes, Mistress," Gary whispered back.
"I'm so very glad, my young slave, because today I intend to rape you, undoubtedly more than once." Indeed, Caroline thought they'd be able to do it three times before Doug got home. Gary was 17---18---after all. "Today," Caroline continued to whisper, "I make you mine in every way. It will be a joyous union, Gary, but remember you do absolutely nothing you are not told to do."
"Yes, Mistress."
"Now, let us begin." With that, Caroline, still gripping Gary tightly by the neck, ripped his t-shirt right off his body. She then unsnapped his shorts and pushed them and his underwear down. "Kick off your sneakers." Gary did so and Caroline was able to push his shorts down far enough until they fell down on their own. She decided to let him keep his socks on. She found him naked but with socks quite adorable. "Don't move." Caroline released Gary's neck and quickly slipped the now quite familiar collar with leashed around him. "Now, get down on your hands and knees and crawl behind me. Make sure you keep up."
Gary did as was told and for the first time saw Caroline in full view. She was wearing ankle-high black boots with four-inch heels, fishnet stockings up to the top of her thighs, very tight, very short black latex shorts, and the leather gloves. Her chest was clearly bare, though he could not see it as he crawled behind her.
Once in the bedroom, Caroline ordered Gary to lie on his back and he got to see her magnificent breasts, nipples firm and protruding with obvious desire. She secured his arms to the two posts above him and cuffed his feet together and then tying them down in the center of the king-sized bed. Gary now also saw that her shorts had a large opening in their center, showing Caroline to be a true redhead. Her bush was neat and beautifully trimmed. For her part, Caroline surveyed her handiwork, reflecting on how long it had been since she first wanted this boy, this young man, so helpless before her. Despite a terrific urge to just jump him at this point, she laid down beside Gary, pushing her breasts against his chest, fondling his balls first (but not his supercharged cock) and then his nipples, pinching and twisting them in a mildly painful, but not unpleasant way, smiling at all times, oohing and aahing every time Gary yelped, feigning sympathy for every mild discomfort she inflicted upon him.
Caroline then spent some time kissing him, slowly working herself on top of Gary's stomach. She pressed her breasts against his face, first to smother him and then to have him use his tongue to worship them as he had so often these past five months.
"Now, Gary, I've wanted for so long to feel that warm, talented tongue of yours on me," she said as she pulled her groin up over his chest to his face, sitting up high to do so. "You will now lick and suck and penetrate me with your tongue until I tell you to stop." With that Caroline dragged her pussy over Gary's mouth and pressed down, gently at first but eventually with more force. Caroline moaned and groaned at the sensations electrifying her body. Her excitement at the moment was almost as great as Gary's when he walked through the door, so it did not take the boy long to bring her to a thundering orgasm, drenching his mouth. "Wonderful!" She did not stop, however, although she let up on the pressure a bit, allowing Gary to work her over as best he could for the first time.
Finally, she stopped that. "All right, Gary, here it comes. Remember to control yourself, hold back for as long as you can, think of other things."
"Oh, God, thank you, Mistress!"
Caroline moved down and took Gary's hard cock deep inside her pussy. He held out maybe 30 seconds, which was better than Caroline thought he would do, under the circumstances. He came screaming but so did she. That was okay because she came again as well and was almost as loud. She had wanted to fuck this young man---she liked to think of it as raping him---for months. Once they both had come, Caroline lied down on top of Gary, but otherwise made no move to disentangle herself from his body. For Gary's part, he had wanted nothing more than fuck his best friend's mother for months and actually found himself crying a little at how good, how relieved he felt, and how wonderful the whole experience has been. Caroline was shocked to find Gary shedding tears.
"Gary, what is the matter?" she asked, not a little bit concerned.
"Don't worry, Mistress," Gary answered, trying desperately to get control of himself. "I was just overwhelmed by the sheer joy I felt at the moment. It was unlike anything I have ever experienced in my life. Thank you, thank you, thank you."
Caroline smiled at her young sex slave, feeling both maternal affection and lascivious, predatory thoughts. "I'm glad, Gary. I haven't taken a virgin since I was 16. It's been a real joy for me as well. But we aren't done. Far from it. But first, here, nurse on this, I promise you will feel better," offering her breast to him. And Gary did, performing an act of security and intimacy ingrained in young men when they were babies.
After some time after this, with Gary still ensconced in her vagina, Caroline was fully aware that Gary had not softened up much and, to the extent that he had, he was now hard again. Caroline began to move to take Gary a second time. But this time, she was rougher, pinching Gary repeatedly and painfully on his nipples, and as they approached orgasm together again, she pulled Gary's face into her breasts with her hands, smothering him to the point where he couldn't breath for the last minute of pounding on his cock until they both screamed again. She could feel him start to struggle for breath under him but of course there was no escape. His terror excited her. Caroline felt energized by her exertions, particularly as she hurt and smothered her slave in the ultimate act of physical conquest. Gary's mind was a mix sensations and emotions. He was excited, pained, and terrified at the same time by what Caroline, his Mistress, was doing to him. But he did not want her to stop, he wanted to do or let her do whatever she wanted to him that would make her happy and give her pleasure. When they both came, she released him and got off, allowing him to catch his breath.
They both were sweaty, gooey, and reeked of sex. "We must shower, Gary. Doug won't be home for an hour, your hair will dry by then. Come, we'll go in together." She released Gary from his bonds and the boy staggered a bit into the bathroom, where Caroline began running the oversized shower with several heads. She took off her boots and removed Gary's collar. Once inside the glass doors, she handed the soap to Gary and ordered him to wash her body. Gary did so reverently, exploring every crack and crevice of Caroline's body with his soapy hands under the guise of cleaning but they both knew it was more than that. Once they both were clean, however, Caroline stopped Gary from turning off the water and embraced him with long, passionate, domination kisses. She forced Gary to his knees and then shoved his head into her crotch.
"Lick me, Gary, lick and suck until I tell you to stop." Gary did as he was told, with an enthusiasm Caroline repeatedly praised. She then ordered Gary to lie down and with the water streaming over them, she planted her ass squarely on Gary's mouth. "Lick it, Gary, you've made it clean, now worship my asshole, any slave of mine must worship me there." Gary was shocked at how excited he was becoming by this. Although the image of Caroline's beautiful cheeks right at this eyes, with water streaming down her back and her long red hair all wet certainly helped. As his erection grew stronger, Caroline noticed and eventually began lubricate it with soap and her hands. And once Gary had licked her rosebud long enough, she increased her tempo and brought the boy to his third orgasm of the afternoon.
They the dried off, got dressed, Gary helped Doug when he got home, and then went out to dinner with his parents. At 11:00 that night, he called Caroline for permission to come one more time, which she gave, but ordered him to whisper into the phone his thanks to his Mistress and praise for her over and over. She ordered him to describe what he was fantasizing about as he did it. She knew she was his fantasy and thrilled to hear him describe an almost repeat of their afternoon before hanging up.
From Behind
For the succeeding several weeks, Caroline's and Gary's couplings continued but with less intensity, usually, and more domination. Caroline continued to make Gary work for his pleasure and Caroline loved watching him do it, whether it was her hair, her toes, or her bathroom floor. It was ended happily enough for them both, though the positions and details varied each time. Finally, however, she decided she wanted to rape Gary from behind. No act was more dominating by a female over a male than taking a slave with a strap-on dildo.
Caroline planned to do it the next time Gary was going to come by, Thursday. She warned him ahead of time the night before on the phone that she was going to take their relationship to a new level the next day and that he should be mentally prepared for it.
Gary arrived that day with not a little bit of trepidation. He was enjoying his relationship with Caroline more than he ever imagined but knew perfectly well how different it was. His fantasies had never been quite like this, though he did see some resemblance. His fantasies often revolved around having sex with an older women, usually the teachers rather than his fellow students. In his fantasies they always seduced him, controlled the relationship, were on top during sex. Since falling in with Caroline, Gary had read a lot more about female domination and male submission, admittedly most of it pornography, but he was aware that there were a lot of things they did not do and that he did not want to do and hoped that Caroline would not do them. Still, whatever she came up with, he knew he could not stop. He was devoted to his Mistress and did not want to stop enjoying what she did with him and to him.
After Gary let himself in, he called out to Caroline to let her know he had arrived. "Come to the bedroom Gary, immediately." Caroline's voice was loud and authoritative, she wanted to proceed at once. When Gary saw her, she looked as breathtakingly beautiful as always, dress in tall black patent leather boots, crotchless leather shorts, a leather halter, and gloves. Her hair, unusually, was tied up in a tight bun on her head. It was a severe and powerful look.
"Strip. Now." It was all Caroline said. Gary did so as quickly as he could and was soon kneeling before Caroline's boots with his cock fully erect and already glistening with droplets of precum. Caroline proceeded to put leather cuffs on his wrists and ankles as well as his collar on his neck. "You may kiss my boots." Gary had learned over the past few weeks that "kiss my boots" meant exactly that but after an appropriate amount of time also meant that he was to proceed with his kisses to Caroline's crotch and worship her pussy until she came. After she did so, Caroline got up from the bed and began to get some things out of her drawer. First, she laid out a thick and heavy rubber across part of the bed, squirting a liberal amount of lubricant cream over its center when she had done so.
"Lay stomach done on the mat, Gary, with you legs on the floor and your cock square on the lubricant." Gary did so, although he found the lubricant rather cold to his initial touch but sooner found his body warming it and mat up. As this proceeded, Caroline chained his legs to the bed, pulling them far apart before attaching one end to his ankle cuffs and the other to opposite bed posts. She then did the same thing with his hands, until he he was stretched pretty tight, but with half his body on the bed, bent at the waste and the other half vertical from the floor.
"There. That will do nicely my young slave." Caroline lied down on top of Gary's back, pushing his body against the mat and the oozing cream and then whispered into his ear: "No boy is truly a slave to his Mistress until he has been raped by her with a strap-on dildo. That's what we’re going to do today. I am going to rape you---from behind. What do you think of that Gary?"
Gary knew it. He did not like the idea. "I don't think I really like the idea, Mistress."
"I'm sure you don't. I'm willing to listen to you beg me not to do it. I'm always up for some begging."
Gary whispered back, with some genuine fear in his voice, "please, please, please, Mistress, don't rape me with your strap-on, please." Gary repeated this several times, until finally Caroline laughed with mock sympathy.
"I think not. We'll proceed just the same." Gary was not surprised and his hard-on had wilted considerably. Caroline got up from the bed and put on her "cock." It wasn't a big one, she did not want to hurt Gary after all and it was his first time. But before beginning, she knew Gary needed a little warming up and encouragement if this was going to be the experience she wanted it to be. First she lubed the dildo and then Gary's ass. But before she began, she stroked and caressed Gary all over, bringing his cock back to life as he involuntarily responded to Caroline's sexual attentions.
And then he heard her say, 'relax, here we go." Gary at first felt the pressure on his anus and then felt it give way, somewhat uncomfortably, as the dildo at first penetrated and then found its way all the way in. Caroline went in and out a few times before pushing a little harder and laying back down on top of Gary, whispering again. "You know what you are, Gary? You're my bitch. Say it for me. Say you are Caroline's bitch."
"I am Caroline's bitch."
"Say it again," Caroline ordered as she stood up again and began to thrust into Gary's ass more vigorously. "Say it over and over again, loud, until I tell you to stop!"
Gary began repeating his fate, not quite shouting but loud enough that if anyone else in the house had been home, they would have heard him. "I am Caroline's bitch! I am Caroline's bitch! I am Caroline's bitch." As Gary repeated his line, Caroline's thrusting grew to a bit more intensity such that he could feel his whole body move, hearing her body slapping against his butt. But as his whole body moved, so did his well-lubricated cock against the now warm rubber mat. The dildo in his ass was hardly comfortable but the whole experience was exciting him intensely and he knew he was going to come. He knew Caroline meant for him to come as she fucked him. And after about a minute more, he screamed an orgasm and Caroline only stopped thrusting when he stopped moaning.
For her part, Caroline came as well as she fucked Gary in the ass. Her thoughts dwelled on the fact this 18-year old boy was her sex slave and that she was fucking him in the ass with a dildo and the dildo was putting pressure on her crotch with each thrust, leading her to come as well.
After they had cleaned up---Gary needed a shower---they resumed more conventional activities shared between a dominant female and a servile male.
The Future
The school year was winding down and all the students were deciding where they were going to college. Gary and Doug were no different. Doug would be entering a decent, though not top tier liberal arts college about two hundred miles away. Gary had a choice. Of the several schools he had gotten into, he had narrowed them down to two. A good school right here at home. It had the advantage of keeping him in the same town as Caroline or a slightly better school about 300 miles to the north. Ordinarily he would have gone north. His parents had put their house on the market in anticipation of early retirement farther south. They had only stayed as long as they did so he could finish school. His home, in effect, was moving whether he did or not. But he wasn't going to make this decision without Caroline. He knew in his heart of hearts that this relationship was not going to go on forever. He wasn't going to marry the mother of his best friend after all. And he didn't think that he and Caroline loved each in that way. They loved each other all right, but more as lustful, very best friends, rather than as boyfriend and girlfriend. Caroline had always made that rather clear: he was a piece of meat to her, one she was very fond of, but there was no room for cupid. Still, by no means did he want their relationship to end now. He enjoyed it far too much and saw no reason why it could not continue while he was in college. But did Caroline think that way? They would have to talk before he made his decision.
Gary arrived at Caroline's house 20 minutes before Doug was to get home. She was surprised. Gary wasn't due to come today at all and now that he has, there really wasn't any time for them to do anything.
"Hi Caroline," Gary said announcing his presence.
"Why, hello," Caroline said a little surprised. "I didn't expect to see you today and it is a little late."
"I know. I actually came to talk."
"Oh, what do we need to talk about? Your lingerie chafing?" Gary turned beet-red at this comment, a reference to Caroline's habit from time to time of ordering him to wear women's underwear under his clothes on some school days as a constant reminder that he belonged to her. It had that effect as well as giving a near constant hard-on if he wasn't otherwise focused on other things.
"No, no. It's about next year and what I am going to do."
Caroline looked at him. "Look, Gary, I know we've enjoyed our time together but I've always known that you would have to go to college. That is something you must do. You certainly can't sacrifice that to stay here with me. If for no other reason than I have no intention of supporting you for the rest of your life just to be my sex slave."
"No, I understand that. I agree with that. I want to go to college. But what if I went to college and stayed in town?" Gary went on to explain the choice he had. "What I want to know is, if I stayed in town would you want to continue? If not, I think it would be best all around if I went north."
Caroline was surprised at this turn of events. She had always assumed that Gary would move away to college and, knowing his parents were leaving the area, figured their fun and games would be over. But now the prospect appeared to continue, possibly for years to come! Caroline walked over to Gary, grabbed him and firmly and deeply kissed him. "Gary, if you stay, yes I would keep you. Our relationship is one of the very highlights of my life. I know eventually that you will have to move on in life, but the prospect of having you around under my heel, literally, for four more years is one I would relish!"
Gary smiled hugely and at that moment Doug came in. "Hey dude, what's up? We weren't supposed to study today."
"No, I just came by to tell you---I was telling your mother---that I have decided to go to Elliott, which means I'll be around. But since my parents are moving, I won't be able to save all the money on room and board as I was hoping."
"Why don't you stay here?" Doug asked.
Caroline and Gary looked at him. "Hey," he said, "it makes sense. I'm leaving. You could take my room---redo it the way you want---it would save you a bundle. "It's not like the house couldn’t hold three of us when I come home to visit."
Gary and Doug looked at Caroline.
In a split second after Doug finished, Caroline imagined what it could be like. This young man would live in her house full-time and Doug wouldn't be here. It opened up all sorts of possibilities. He could be naked when he wasn't at the college, in class. He would be available to satisfy her sexual urges whenever she had them! She could introduce numerous new games with him. She would increase his tolerance for pain, for example. He could be in bondage for days at a time! Finally Caroline spoke: "Why that would be a great idea!!"
Her Son's Best Friend, Part II
(It may be longer than two parts.)
Almost Six Years Later
Caroline knew it would have to come to an end. For the past six years, while Gary shared a room in her house, earned first a bachelor's degree and now almost finished with a master's degree, he was her lover and her slave. Caroline dominated Gary sexually more completely than she had ever dominated anyone in her life. She reflected fondly on the depths of submission and depravity to which she subjected Gary during that time, points at which she had not even imagined six years ago as Gary first succumbed to her designs for his place in her life. When out of the house, Gary always wore female lingerie or chastity belts or both. When at home, Gary was always completely naked except for his leather collar, whether he was with Caroline, or doing chores, or even just sitting and doing his college homework. Gary performed service and sexual activity on Caroline whenever she demanded, which was pretty much daily, often more than once a day. If Gary didn't spend at least an hour a day with his head clamped between her thighs just worshipping her pussy, it was a slow day.
When Caroline had first set her sights on Gary, he knew very little about the ways of women, truly, and what he has learned over the past six years was more than most men knew, but still resembled an incredibly narrow range of women. Caroline realized that she has without a doubt ruined Gary for most other women. He would be incapable of functioning sexually in a "normal" relationship. Caroline regretted this, but in the end she would not have done anything different. She loved Gary as her lover and her slave but it was time for him to move on. Oh, she thought, he could stay with her forever, but that would be a waste of a talented young man with a gift for mathematics who could make a real contribution to the world. Unfortunately, the kinds of jobs and the contributions Gary could make could not be done in this town. He had to seek his fortune elsewhere, without her, because she had no intention of uprooting her life here.
She would have to tell him soon. She was not sure what thought he had given to the idea that he must move on in a few months, but he certainly must suspect what's coming, unless he thinks I am not planning to let him go.
Caroline took some consolation in the situation with the knowledge that Gary was not, apparently, incapable of interacting with the opposite sex outside of her home. In the past year, Gary had struck up a platonic friendship with Heather, a fellow graduate student, but in the engineering department. Heather was about as tall as Gary, around 5'7" and had a deceptively pretty face that was not at all obvious from a first glance, as it was hidden behind not-very-flattering glasses and a bit of late acne. She was the same age as Gary now, 24. Of course, when she came by the house, all was perfectly normal, nothing at all hinted at the unusual relationship Caroline had with Heather's friend.
A few days after Caroline had contemplated her dilemma about what to do about Gary, Heather dropped in, waiting for Gary to get out of classes. They planned to do some studying and, Heather hoped, to grab something to eat.
"Hi Caroline," Heather said as Caroline opened the door, "I assume Gary isn't back from classes yet. Do you mind if I hang out here until he gets back? We're planning to study for Friday's test."
"Not at all dear, do come in."
Caroline wasn't sure why she said what said next, perhaps because it seemed like a natural line of conversation for a 45-year old "normal" landlady. "It's so nice to see that Gary has found such a nice person as a girlfriend." (It was a comment Caroline never would have made in front of Gary, and Heather was almost never at her house by herself.)
Heather sighed deeply. "Oh, I am not his girlfriend. I wish I were, but I am not. Gary has never shown much interest in me, or any other girl for that matter, and has brushed me off the couple of times I mentioned it would nice to be something more than just friends. I decided he is gay but doesn't want to talk about."
Before she could stop herself, Caroline laughed and blurted, "Oh, he's not gay!"
Heather studied Caroline closely now and did not say anything for a long time. Caroline, surprising herself, grew uncomfortable in the silence and under the gaze of this obviously intelligent young woman.
"You said that as if you know it for a fact but yet I have never seen or heard him discuss a girlfriend." Heather finally made this statement as a set of facts, waiting to see if Caroline would challenge them.
Caroline felt that any denial at this point wouldn't be believable, but she tried anyway. "Oh, no, no, I just don't think he is gay, that's all." It sounded lame and both Caroline and Heather knew it.
"Look, Mrs. Barron," ---Caroline noted the sudden formality--- "I like Gary a lot. He is the nicest, sweetest guy I know. Always very generous with time and help, and by far the most respectful of women in the math and engineering departments. I'd appreciate you helping me understand him. You probably know him better after these past six years than anyone else."
Caroline now realized she would have to be more forthcoming, especially since Heather was just the type of woman that Caroline had ruined Gary for.
"All right dear, I'll try to explain. But please don't be judgmental of him. Gary could use friends like you and I don't want to say anything that will ruin that."
"I doubt there is anything you could say that would stop me from liking him." Indeed, Heather thought to herself, I love him. Nothing could be worse than this feeling of unrequited love.
Caroline ventured forth. "If Gary doesn't show much interest in other women, it's, well, because he and I are lovers, and have been since he first went to college."
Heather's mouth dropped open, and then tears glistened in her eyes but she didn't lose herself to her emotions. "Do you love him? Does he love you?"
"Well, it is clear we enjoy each other's company tremendously, but it is a little hard to explain because our relationship is a bit unusual."
"How?" Heather asked, feeling not a little bit of anger welling inside of her.
"Gary. . . Gary is my slave, my sex slave. I love to dominate him and he enjoys submitting to me."
"You mean . . . as in black leather, whips, and bondage?"
"Yes."
Heather continued, slowly winning the struggle with her emotions, "so he really enjoys that or is it something you force on him?"
"Well, I suppose in the beginning I did force the issue. I made it clear as I seduced him---and I admit I did seduce him---that if we were going to enjoy an intimate relationship, it would have to be this way. And at 18, a young male would be willing to do almost anything for regular sex."
"I see." For a full minute Heather said nothing and Caroline didn't either. Finally, Heather got up: "I have to go, Please tell Gary I had to cancel. Give him any excuse you want.
"Heather. . ." But it was too late, she had moved swiftly out of the house and showed no desire to continue the conversation. That night, Gary tried to call to find out why Heather had cancelled but she had turned off her cell phone.
The next day, Heather dropped in to see Caroline when she knew Gary wouldn't be there.
"Heather!" Caroline said in surprise as she opened the door. "I'm so glad you came back. I feel I need to explain more."
"It's okay Caroline. You don't have to explain anything. I came back because I have a proposition for you." Caroline noted the use of her first name, Heather was deliberately making her equal. After they sat down and Caroline poured some tea, Heather stated baldly: "I want to propose a trade: Gary for my brother."
"What?!?"
"You heard me perfectly well. I want Gary. I love him and I'll take him the way you trained him and continue it if that is what he wants. We all know Gary is leaving anyway, but maybe we can do it in a way that sends him into my arms. In return, I'll convince my brother, Christopher, to live here. He is planning on attending college here as well, he just turned 18, and I happen to know he'll love what you will do with and to him. So how about it? The only thing is, to get this deal, you start pushing Gary into my arms immediately. I want him and I have wanted him practically since the day I met him."
Caroline's mind reeled with what she had just heard. "How do you know your brother would love to be dominated, to be sexually enslaved by a woman, particularly a woman much older than himself? I'm 45 now."
"Easy. I more than once came across his stash of pornography he hides from our parents. The one recurring theme over and over in almost everything he had was a strong, powerful woman dominating a weak or submissive male. Stories, letters, pictures, it was all the same. I actually found it quite intriguing myself, but I've never really tried it."
Caroline was now thinking that not only could this work, but how it would work. Moreover, it would be the best possible outcome, to release Gary to another woman willing to dominate him but yet also love him. All of the heartbreak she was sure Gary might have otherwise endured could be eliminated. Heather and Gary are friends. All he has to do is see her as a woman who would love to go with him, and dominate him, and the rest would follow.
"All right, Heather. I like the idea. I will entrust Gary to you even if it doesn't work out with your brother, but I would dearly love another nice young man to do my bidding."
"Oh, he'll be yours all right, the only question I have to think about is whether to put it to him up front, or simply convince him to live here, and then I guess he would easily fall under your sway. You would be like gasoline to his fire."
"Very well. Let's talk about how to make it work with you and Gary. I think the best thing to do is to have you observe us together for a bit, to see what we do, how he behaves, and what he likes. Then, with him blind-folded, bring you into our get togethers. This has happened occasionally in the past when a couple of dear friends from college would visit. I could then leave and let you have him for a while, but you will have to decide when and how to tell him. If you do it right, he will embrace you. I am sure he knows that he and I cannot continue on after this year, but I have not yet told him that directly. I think he wants me to push him out, rather than tell me he has to go. I haven't done it yet."
Heather was nervous about this prospect: it was an all or nothing gamble, but knew she had to take it. If Gary never showed any interest in her because he already had everything he wanted at Caroline's, then perhaps the prospect of continuing on with her would permanently change the shape of their relationship the way she wanted.
Heather stated, "Gary will be here soon. He's expecting us to study. I called him this morning, feigning illness yesterday, and suggest we pick up where we left off today. Do we start now or wait until another time?"
"Let's do it tomorrow. Your test will be over and Gary's coming straight here. Here's a key to the house and you can come after classes. Gary is due home at 4:00, where he already knows we will be "playing" immediately. When you come in, go to my room. You'll find plenty of appropriate clothing in my bureaus and closets. They will be a little big on you, but you must look the part for it to work. Then hide in the closet until I tell you to come out. Have you read enough about this to understand the psychology behind dominating a male?"
"I think so. I guess we'll see."
"In the meantime, why don't you go home and have a conversation with your brother." Heather could see the excitement in Caroline's eyes. She clearly had a desire for fresh meat.
"Okay, but let take of picture you first. I think that will help sell the deal."
Caroline was about to smile when she said: "wait, let me put on some more appropriate clothes." Caroline left and five minutes later came back wearing tall, high-heeled leather boots, tight black shorts, and a tight black t-shirt, accentuating her magnificent breasts. Sexy to the vanilla observer, but sure to turn-on a submissive young male.
Selling the Deal
When Heather arrived back at her apartment, having thought all day yesterday and the way home what she would say, she immediately dialed her younger brother. "Hi Chris. I've got good news. I've found a great place for you to live next year. You'll love it." Only Heather called him Chris, because he hated it.
Christopher was surprised. "What are you talking about? I'm planning on living in the dorms."
"Well, you see, I think you'll like this place better. You would be renting a room in a house, the same room used by a friend of mine whose leaving. The landlady is just your type. You'll like her."
"And why would I want to live in that situation? The dorm has got to be more fun."
Heather warmed to her subject carefully. "Chris, I have a confession to make. I know about you. I know what you like."
Christopher hesitated briefly, wondering if his sister was talking generally or really knew more about him than he wanted her to. "You know many things I like. What are you getting at, Heather?"
"I know about your pornography stash. I have read it all."
After a very long silence, Christopher only said, "oh." And then, "um, so?"
"Look baby brother, I'm cool with it. You like what you like. I admit, I found your stuff exciting, too, but from the woman's perspective. Really, it's okay. I won't tell anyone."
"Well, then, why are we having this conversation?"
Heather chose her next words carefully. "Let's face it, Chris, you want to be dominated, sexually, by a woman. It is what you have always wanted. Some of the dates in your pornography stash date back to when you were 12. Your every sexual thought since you first had them were about being dominated, weren't they?"
"Uh, I guess so." Even so, just having the conversation about domination was giving Christopher a hard-on.
"The landlady who owns the house where you would rent a room, she'd dominate you, she likes bondage and domination, she particularly likes to dominate young men. She's beautiful, here let me send you the picture."
Within a few seconds, Christopher was looking at the picture of Caroline Barron in black books and skin tight clothing. His cock grew even harder.
"And she's tall, Chris, four or five inches taller than you." Heather had noticed the large number of amazon-themed stories in her brother's stash. "This is your opportunity to live the sexual adventure you have always wanted."
Christopher was thinking with his head now, but not the one with a brain in it. "Sh- Shouldn't I meet or speak with her or something?" But then he thought, who am I kidding. I am going to do this. After all, if it doesn't work, I could always leave.
"Tell you what, I'll have her call you, okay?"
Mouth dry, Chris replied, "okay, sure, that's a good idea. Bye."
Heather immediately called Caroline, gave her the details, let her take it from there.
Capturing Gary
When Heather arrived the next day, she was excited about what was coming, but still couldn't wait to ask. "So, did you call Chris?"
"Oh, yes," Caroline replied. "Thank you. He sounds really sweet, I love them that way you know. He was already calling me mistress by the end of the conversation. We exchanged some emails and pictures. He needs someone like me very badly, doesn't he?"
"Yeah, but I expect you won't hurt---I mean, harm---him. You’ll treat him well? He is still my brother, after all."
"Of course, I'll treat him as well as I have treated Gary, the only difference is that I'll be able to move things along much faster with Christopher."
With that Heather bounded up the stairs, her heart pounding in her chest so hard she thought it would break her open.
Heather found among Caroline's things enough to make her look like a totally hot dominatrix. She put on a pair of her boots, two sizes too big, but not unmanageable. A black hat, black gloves, and a black corset she could tighten completed her outfit. She then staked out a position in the closet that afforded her a clear view of the bed area from the crack in the door.
It wasn't long before Heather had someone enter the house. She had left the door to the bedroom open and listened carefully for Caroline and Gary to come upstairs. She heard Gary call a "hi Caroline" and Caroline respond with: "no chores today, Gary, I want you upstairs right away." Gary answered with a "yes Mistress."
A minute or two later, Heather was shocked and titillated by what she saw. Gary had entered the room wearing nothing but a tight-fitting pair of pink women's panties with decorative lace. It could barely contain his clearly bulging erection. Gary immediately dropped to his knees, clearly waiting for Caroline, who arrived about a minute later.
Caroline knew exactly what she wanted Gary to do. It would be a sensual, service-oriented day for Gary. She wanted Heather to get excited by what she was going to see, to want it for herself, rather than be repelled by one of her more intense sessions with her slave. Caroline commanded Gary to brush her hair and give her a massage.
The effect on Heather was precisely what Caroline wanted. Heather was surprised how hard Gary remained doing these things to Caroline. He was sexually excited to be serving Caroline in any way she wanted! It made Heather want Gary all the more, her mind now flashing to what life could be like with him. After about 15 minutes of those sorts of activities, Caroline ordered Gary onto the bed, but out of his panties first.
"Lay back, get in the position." Gary spread out his legs and arms and Caroline cuffed them tightly to the bed's posters. Then she also blindfolded him. Caroline then began a favorite of the two. After a bout of deep-throated kissing, she alternated between having Gary suck on her large, ripe breasts and smothering him with them up to a minute at time. Heather observed how Gary's erection never wavered and remained poking into the air the entire time. After satisfying her desires this way, Caroline moved her bottom up to where her pussy pressed against Gary's mouth. "Stick out your tongue, Gary, and get to work. I want a lot of action here now. I want to feel your tongue inside me."
Gary did completely as he was told, bringing Caroline to two orgasms before she climbed off. She did nothing for her slave, however. "Gary, I have a friend here today whom you will now entertain as you entertained me. You will follow her orders as if they were mine. Are we clear?"
"Yes, Mistress," was Gary's answer, but he was not a little bit nervous and it showed by his suddenly weakening cock. Caroline had on a number of occasions over the years forced Gary to satisfy one of her friends from college or even a relative, but those events always began downstairs and stayed there. They had never gone to a bedroom, he was never tied down when they happened, certainly never blindfolded, and Caroline always remained in the room.
Heather emerged from the closet as Caroline left the room, but not before giving the younger woman an encouraging smile. Disguising her voice just enough so as not to give things away right away, Heather said: "You are a lovely young man, Gary. Caroline has said so many nice things about you. I think we are going to enjoy our time together very much."
"Thank you, Ma'am, Gary said, straining to see something through his blindfold but failing.
Heather ran her hands up and down Gary's body, feeling him in a way she had always wanted but couldn't because it would have been far more than a platonic touch. The gentle voice and the caress of her hand relaxed Gary and caused his cock to return to its previously hard state.
She seems nice, he thought.
Finally, the mystery woman climbed onto the bed with Gary and began to kiss him with an intense passion he found surprising for one of Caroline's friends. Usually they showed little interest in that. It also afforded him the first opportunity to smell her and found her scent familiar but unable to pinpoint why. As they kissed, Heather continued to touch, caress, and stroke Gary all over his body, in a way that was so sensual he began to yearn for this woman to fuck him. This surprised him because usually he did not want Caroline's friends to do that and she did not let them. Oral service had been her limit. And that came here as well. Heather desperately needed some relief from the fires burning in her groin and she soon settled her pussy down on Gary's mouth as well. "Lick me, Gary, lick me until I come."
As he did so, Gary could tell this woman was not of Caroline's generation. She's a younger woman, he thought. The thought excited him and worked hard to please her and brought her to two successive orgasms over the next 10 minutes.
After that, thinking that at least she could experience that much but was unwilling to proceed to intercourse until they talked, Heather dropped her voice disguise, her heart pounding, removed the blindfold. "Let's talk."
"Oh My God! HEATHER! What are you doing here?!" Gary strained against his bonds but they didn't give way. Heather did not remove herself from Gary's chest. At the same time, she observed that Gary's erection was rapidly deflating and the blood from that part of the body was moving to his face, which was now quite red from acute embarrassment.
"Calm down, Gary. I said we should talk."
"I don't want to talk; I want you to get the hell out of here!"
Heather thought that this was not a good start but nothing would be gained by letting Gary go. If she did, she'd never get him back. "No!" she said firmly. "Not until we talk about what happened here!"
Gary finally stopped pulling on his restraints, rested his head back on the pillow and looked with angry, watery eyes. "Fine. Go ahead and talk. What the hell are you doing here?!" Gary never felt so mortified in his life. His best friend from college was sitting here, in Caroline's house, in full knowledge of his secret life of all these years. He wanted it to all go away. He wasn't sure if he was more angry with Heather being there, knowing what she now knew, or Caroline who obviously set it all up. He tried hard to simply not cry.
Even angry he is adorable, Heather thought. She hoped this would work out. "Caroline and I talked, Gary---"
"Clearly!"
"Will you just shut up a minute and listen, or I'll take that whip off the wall and make you truly regret it?" Heather said pointed to one of Caroline's more ominous looking implements.
Looking chastened, Gary simply said: "okay."
"While it wasn't her intent to do so, it came out when we were talking, the nature of your relationship with her. But you both already know that it is coming to an end. You're going your separate ways. And, well, let's face it, you need this Gary, you need to be dominated by a woman. Admit it. And I want to be the one who does it."
Gary paused a long time before speaking. "I admit I will be leaving Caroline for good when we graduate. I admit that I want...I need to be dominated. But so what? It's not like we're going to be together in a few weeks either. And your my friend...I thought."
Now it was Heather's turn for her eyes to well up a bit. "I am still your friend, Gary. And we can still be together. The fact is, you stupid idiot, is...is that I love you. I have loved you practically from the day we met. I want to marry you. We could start our careers together and take what life gives us, together. And if you would want to be ordinary husband and wife, I would love that, too. But, frankly, I would love even more if when you came home at night, you fell to your knees, kissed my black boots and served as my love slave. Forever."
Gary stared at Heather with his mouth open and, he discovered, a growing erection. The thought of what Heather just described sounded wonderful! He needed what she was offering. And if he never thought of Heather in romantic terms it was because he was completely absorbed by Caroline. But now, confronted with those thoughts directly and having a choice to make, he realized that perhaps he loved Heather as well. He had always enjoyed her company in everything they did and shared many interests and many values. He had had few sexual thoughts about her because, well, Caroline was focus of all of his sexual energy, and he did not imagine Heather as the dominatrix type. Looking at her, sitting on his chest in black leather was helping to dispel that notion.
Heather continued to say nothing in the long silence but glanced momentarily behind her to see Gary had in the long silence grown fully erect again. She grabbed his cock gently but firmly, and broke the silence: "Is this your answer?" she asked smiling.
The sound of Heather's voice brought Gary's mind back into focus. "I, I guess it is. Maybe that head understands better than the one on my shoulders. I have loved you so long as a friend, I just never thought about you as a girlfriend. I mean, let's face it, with Caroline in the picture, I wasn't ever thinking about finding one. So now what?"
Heather giggled with joy, with waves of relief and happiness flowing through her but not so much as to reveal to Gary just how desperately she wanted him. "Well, it seems a shame to waste this," she said rubbing his cock, "but I would understand if you want to wait a bit before getting so...intimate again."
Gary looked at the door and saw it was still closed and locked from the inside. He smiled at his girlfriend. "I'll leave it up to you. After all, you're going to be the one in charge, right?"
"Ohhh, yes! I'll command and you'll obey. For the rest of your life." Heather then bent down, grabbed a fist-full of Gary's hair and began kissing him with a passion held in for more than a year. Soon Heather slid her groin down over Gary's penis, lingering for a few seconds and then ever so slowly taking him inside her, at a pace Gary couldn't help but find maddening. She eased herself all the way down his shaft until his envelopment was complete. Only then did she release his lips from hers and begin a slow but increasing grinding motion with her pelvis. As Gary opened his eyes when she did, he saw Heather with hers closed, her tongue licking her lips and clearly in an ecstasy greater than sexual pleasure alone. He closed his eyes again to enjoy the ride. Neither young woman and young man, mistress and slave lasted very long. They came together in shouting match of sexual climax loud enough to bring a smile to Caroline Barron's mouth half a house away.
Moving Out, Saying Good-bye
The succeeding two months were rather hard on Caroline. She felt that she and Gary couldn't continue as they had been now that he and Heather were joined at the hips, as it were. Moreover, Gary was still a renter in her house and was therefore entitled to all the rights and privileges tenants have, such as overnight guests. Heather came over frequently and Caroline's home afforded the two more privacy or, arguably, less of a need for privacy than Heather's, which she shared with two other students. Neither of those girls could possibly understand the new, dynamic and very different relationship Heather and Gary were forging.
And truth be told, Caroline didn't mind. It gave her regular opportunities to talk with Heather, usually about Gary, when he wasn't around, and often when he was. Caroline and Heather talked at length about dominating a male, sexually and beyond, the latter still very new to the practice. Gary didn't mind this either, even if it seemed a little embarrassing and objectifying at times. But, like most guys, he didn't mind being objectified either.
Caroline often got to listen, unbeknownst to Heather and Gary, to the young mistress discipline and conquer her young slave. She had discovered long ago the heating ducts in her house provided very easy listening to Doug's room, which Gary rented, and she could almost hear everything if she listened carefully and very quietly. It was in that way she often headed off some of Doug's more stupid ideas when he was growing up and her son had never quite figured out how his mother was always one step ahead of her. So for the last two months Caroline lived vicariously through Heather's and Gary's antics. She knew Christopher would be moving in about a month after Gary left and that seemed very promising indeed, but having been used to dominating a young man virtually daily for six years, it was hard not to partake in the interim.
Finally, Memorial Day weekend rolled around and Gary, with Heather's help, was packing up and moving out. They were headed west to start their careers and lives together. Both had graduated with honors, with Caroline a guest of them both. The parents of the twenty-somethings each commented to their children after having met Caroline what a good influence Gary's landlady must have been on them. If they only had known, Caroline thought.
Heather and Gary carried the last two boxes down from the stairs. "Well, that's all my stuff, Caroline," Gary said. "The furniture of course is yours, so it is all set for your next tenant." The way Gary said that suggested to Caroline that Heather had never told him who the next tenant was going to be or about the "deal." On the other hand, Gary may not want to dwell on it either, in light of their long relationship.
Heather returned from putting her box in the car and then grabbed the one in Gary's hand. She had thought about this for a long time and while she had some misgivings, thought this was the decent thing to do. "Look, I've a got a couple of errands I need to run. It'll take me a couple of hours. Gary, why don't you stay here. You and Caroline could, uh, you know, say a meaningful good-bye." Heather noted that Caroline's face brightened momentarily and then retreated to her cool reserve and Gary looked shocked.
"Really?" he said.
"It'll be. . .---I'm cool with it," Heather replied. "But after today," she grabbed his shirt and pulled him close to her lips and eyes, "I am your world." She then let him go, choosing not to reinforce the point in front of Caroline with a possessive kiss. "Have fun and, Caroline, no permanent damage, okay?"
Caroline smiled, "thank you dear. That was really very sweet of you."
"See you in two hours." Heather left, closing and locking the door behind her.
Caroline wasted not one second. "Strip and get on your knees, with your head down, Gary. I have hated seeing you in clothes in my house these last two months." Gary did so as fast as he could and within one minute was kneeling down with his forehead touching the floor. Caroline took off her shirt and dress, leaving her standing there in a black lace bra and panties and four-inch pumps. "Now crawl over to me, and begin kissing my feet and legs, work your way up to my pussy, and then lower my panties with your teeth and worship me until I come!"
"Yes, Mistress, thank you Mistress." It felt like old times to Gary, as much as he loved Heather and looked forward to their life together as mistress and slave, Gary always felt overwhelmed by Caroline. Her height, her intelligence, her beauty---she was superior to him in every way and he knew it. That innate sense of inferiority he felt before Caroline always made him want to do anything she desired. The past two months, apparently, had not changed that at all.
Gary kissed Caroline's feet, flicking her ankles with his tongue. Slowly he worked his mouth up each of her legs, finally nuzzling her crotch with his face, a spot that made him feel very at home and a sensation at which he was certain Caroline shuddered. As he began to work Caroline's black panties down just enough to give him access to her pussy, his eyes widened at the sight. Caroline's bush had more hair than he was used to seeing, clearly she had stopped trimming it when Heather entered the picture, but it was beautiful and full, and smelled of perfume mixed with feminine excitement. His hands stroked Caroline's legs, running them slowly up and down, feeling the strength and glory as they seemed to go on forever.
His tongue began to probe through the forest and when it found her labia, he slowly licked up and down. Caroline had missed Gary's touch so much; she gave in to the temptation to push him along once his tongue met her sex. Shortly after the licking began, Caroline grabbed Gary's head and started to control the pace of the action. She forced his face into his pussy while at the same time rubbing herself up and down as Gary struggled to breathe. Gary by this point had grabbed hold of Caroline's buttocks with his hands, in part to steady himself against Caroline's increasing control of his movements. Soon he could feel and hear Caroline come in repeated shudders accompanied by loud groans of ecstasy.
"Don't stop, Gary. Again," Caroline commanded and while she no longer was forcing Gary into her, she did not remove her hands from his head, waiting rather to see her former slave begin on his own where she had left off. Gary took the opportunity to press Caroline against his face, as he stretched out his tongue, entering her vagina with it as far as he could with a swirling motion he learned long ago Caroline loved.
"Oh god, Gary! Deeper! Push in deeper!" Caroline moaned over and over until she felt herself coming again, and she cried out more screams of delight.
Finally she released Gary's head and he sat backward on his haunches, his face glistening with the juices from Caroline's pussy. Pulling up her panties, Caroline declared grinning, "I've missed that! But let's go. Crawl upstairs. I have an hour and forty minutes. I intend to use every one of them." Caroline followed him as he climbed the stairs on his hands and knees, punctuating his movements periodically with the occasional smack on his rear. Once Gary was in the room, Caroline ordered him to lie down on the bed on his stomach with his feet on the floor. Caroline meanwhile put on a pair of soft leather, thigh high but low-heel boots. She wanted to wear them the rest of their time together and sometimes heels get on the way of certain activities. She put on opera-length leather gloves and then strapped on a rather substantial looking dildo. Gary has come a long way since his first time, Caroline thought as she admired her look in the mirror.
She then dipped the phallus in lube and walked over to her prostrate slave. She then twisted both of Gary's arms behind his back as she rested the tip of the dildo on his anus, between his checks. Gary could feel the cold hard object violating him even as his erection grew harder. "You loved being my bitch, didn't you Gary?" Caroline whispered.
"Yes, Mistress."
"Then let's make this one to remember, shall we? Say it!"
"I'm Caroline's bitch!"
"Louder!"
"I'M CAROLINE'S BITCH!!" And with that, Caroline plunged her phallus into Gary's ass and worked the tempo faster, yet still painfully twisting Gary's arms all the while listening to him yell over and over that he was Caroline's bitch. Finally it was all too much and Gary screamed out, coming on the sheets as the abrasion against his cock and prostrate was too much.
After such an intense start, Caroline took it more sensuously for the next hour, allowing Gary his old habits of brushing her hair doing her nails, worshiping her breasts for what seemed like an eternity. By the end of all that, Gary's erection had returned and she wanted to end on a particularly intense note. Using much of her bondage gear, Caroline trussed Gary to the bed to the point of near immobility with leather straps, cuffs and mitts criss-crossing every part of his body, topped off with a bondage hood and gag that left only two small holes through which Gary could breathe. Caroline then sat down on the bed, stroking, lovingly, every exposed inch of her soon-to-be-ex-boarder’s skin, including painfully working the nipples. She sat there, touching and relishing the moment, the complete control she had over this young man. And when she knew it was nearing the end, she mounted Gary's penis, fucking him to one final tremendous climax, which was quite loud even through the hood and gag.
When they were done, Caroline released Gary from her bondage for the last time. "Stand up, Gary," Caroline ordered, but not at all unkindly. She pull him into her, standing eight inches taller in her usual high-heeled boots, bending his head back and gave him a long deep passionate kiss. With tears in her eyes, "these past six years have been some of the best in my life. Thank you."
"Oh, Caroline." It was Gary's turn to turn teary-eyed now. "It was a wonderful, wonderful ride and I wouldn't have traded it for anything. I love Heather, but know that there is a part of me that truly wishes this were not coming to an end and I could stay here forever."
For a long time, both former mistress and former slave said nothing and continued their embrace and gentle caressing. Finally, it was Caroline who broke the silence. "You must shower now. Heather will be back soon."
"Yeah." And Gary left for the bathroom.
Caroline put on some more appropriate clothes and went downstairs to wait for Heather and Gary both. Soon enough Heather pulled up and came in. "Hi," she said a little uncertainly.
"Gary's in the shower. He'll be down shortly," Caroline replied. After a longish pause, Caroline added: "You have a wonderful young man there. I'll admit to you that I will miss him very much."
"I know. I have known that since the day I met him."
"Of course."
After another long pause, Caroline spoke again. "That said, if you ever need any advice or suggestions on how to break him to your will, I'm just a phone call away!"
Both women just laughed.
"What's so funny?" Gary had come down the stairs at that moment. Both women laughed again at his exquisite timing.
"Nothing. Nothing you have to worry your pretty little head about," Heather answered. "Well, I guess were all set to go?"
"Yeah, you have everything in the car. I guess this is good-bye, Caroline."
She gave them both one final hug and said, "do keep in touch. I look forward to hearing from you both about everything."
And with that, Heather and Gary went out the door, followed by Caroline, got into the car (Heather got behind the well) and drove off.
Chapter 3: Her Son's Best Friend: Christopher joins the Barron household.
Four weeks had passed since Heather and Gary had driven away to start the rest of their lives together. It had been a very bittersweet moment for Caroline. She was happy---more relieved---that she wasn't simply casting Gary off with his now twisted sexuality. She had also grown quite fond of him, especially the time they spent together, and she frankly missed him.
Today, however, she didn't feel that way and was quite excited. Today was the day Christopher, Heather's brother, was set to move into Gary's old room to attend the same college Gary and Heather had gone to. It had been Heather's idea, once Caroline had explained to her the nature of their relationship. She had fallen in love with Gary and wanted him for herself. In exchange, Heather had proposed to convince her brother---Christopher---to rent the room Gary had. Heather explained that Christopher secretly fantasized and craved being sexually dominated by a woman and would very likely jump at the opportunity to be under Caroline's velveted fist. And, not without some trepidation, he had. Caroline remembered her phone conversation with him vividly. . .
"Hello?" Christopher said, a little uncertainly.
"Hello, Christopher. My name is Caroline. Caroline Barron. Your sister said you would be interested in staying at my house while you attended college next year. Is that true?"
"Oh. Hi, Mrs. Barron. Yes. I guess I am. Is that all Heather said?"
"You sound very sweet, Christopher. No, that is not all she said. Are you alone right now? Can we talk freely?"
"Yes, I am home alone at the moment. My parents went out for dinner."
"Very good. Well, Heather described you as a remarkable young man. But the focal point of our conversation about you was that you fantasize about being dominated by a tall, beautiful, sexually powerful woman. Christopher, I am such a woman. I can make every fantasy you've had come true, and then some. Is this what you want?"
"Ohh, yes." Caroline remembered Christopher's voice sounding very hoarse at this point.
"You sound like a delightful young man, Christopher. But before you say yes, to be fair, I want to be sure you know what you are getting yourself into. You will have very little freedom, outside of attending your classes and very little time for other extracurricular activities. If you live here with me, I will dominate you completely---physically, mentally, sexually. You will of course have the necessary time to do your school work, but pretty much the rest of your waking---and sleeping---hours will be devoted to service to me. You will be my plaything, my pet, and very much my slave. I ask again, is that what you want?"
Caroline remembered the long pause and then asked: "Are you hard right now, Christopher?"
After a moment's hesitation, "Yes. I am harder now than I think I ever have been."
"Then this is what you want."
"Yes. Actually, it is something I want, desperately. For as long as I could remember, I have wanted it. But. . ."
"But what?"
"Well, I have never had what you describe. I mean, I've played around with a girlfriend on occasion, but those experiences were lame and she was never into it. What if, what if the reality is not as good as the fantasy? Can we stop? Can I leave? What would happen?"
"Those are good questions and it shows you have a head on your shoulders as well as in your pants. I’ll be honest. You don't get to cut and run just because sometimes it is a little uncomfortable. But I don't plan to abuse you, Christopher. I will discipline you from time to time..."
"Oh, that's okay--"
"Please don't ever interrupt me again, Christopher."
"I'm sorry." Chris sounded genuinely contrite over his impoliteness.
"That is all right. I expect that you have much to learn. What I expect is you commit to this for a semester. We will talk extensively and over time when we meet about what you think is interesting and appealing and what isn't. I will take your opinions into account. But I expect you to try to make this work. I will as well. If, after a semester, you decide that this isn't you after all, we can part as friends. You can live in my house as a regular boarder or move out. Although, I'll tell you now, I will probably prefer if we make a clean break of it."
"That sounds. . .good."
"Excellent. So. Have you been touching yourself as we talked?"
"Yes, I confess I have."
"Stop it at once. How often do you masturbate?"
Clearly a bit embarrassed at being caught, "uh, two to three times a day."
"Wonderful. Just wonderful. Christopher, we are going to have such a good time together, I am sure. When do you expect you will want to move in?"
"I was thinking about July 1. I could tell my parents I have some sort of summer thing here, but in reality we could take the two months before school starts to, well, figure out how it will work."
"I love the idea, Christopher. I'll plan on taking some extended vacation time starting on the first. I think we will get along swimmingly and have a wonderful ride over the next four years. You have my number if you need anything. And I will call from time to time to check in, or you can feel free to call me. To ask any questions you want or state any preferences you have. Or you can wait till we meet. Ultimately, you will have to bare your soul to me Christopher, tell me every fantasy, every preference, every fear you have about being totally and utterly dominated and controlled by me."
After a little more chit chat, Caroline ended the phone call. In truth, Christopher didn't call much and neither did Caroline. He had preferred to wait until they met and that day was finally today.
Chris Becomes Caroline's Slave
When Chris arrived at Caroline Barron's house his mind was virtually reeling from various thoughts. Foremost was probably relief that, because he was not starting school right way and was going to have an "internship" over the summer, his parents had decided not to come and had decided to buy him a decent used car for school. That said, it had been a difficult drive from his parents’ home to here. The road was usually not what he was thinking about. As he turned off the engine, double-checking the address, his heart was pounding so hard from excitement and fear that he felt as if it would burst through his chest. While the car was loaded with various bags, boxes, and small electronics, he simply grabbed his backpack and headed for the door.
He knocked, and then waited what seemed like an eternity. Finally he heard the tell-tale sound of heels clicking on a hardwood floor. When the door opened, the image of Caroline Barron made his mouth go dry. Heather had not lied and Caroline was more attractive than her pictures. First, she seemed very tall, a fact helped by the four inch heels on the tall black boots that Caroline wore over her capri pants. At only 5'7", Chris stood eight inches shorter than Caroline, which was evident since he was forced to bend his neck up to be able to look her in the face. And that was a pretty image as well. Caroline retained a lot, though certainly not all, of her youthful beauty even though she was now 45. However, she had, it was said, "aged well." Her very long red hair was tied in a ponytail, which swayed beautifully as she walked. Her breasts were large and rounded, Chris could tell, trapped behind a quite tight fitting white satin blouse.
"Christopher! Do come in! It is so good to meet you at last. How was the drive? Any problems finding the place?" Caroline's warm greeting set Chris at ease a bit as he walked into her house. Caroline liked what she saw, too. Chris was cute more than handsome, a quality he shared with Gary but not her son Doug, who had his father's ruggedly handsome good looks. Chris looked fit, but clearly did not work out. I could take him, she thought, if it came to that.
Hoping his nervousness was not too evident, Chris replied: "Thanks. No, the drive was fine. And it is great to meet you, too."
"Come sit down for a minute, let me get you something to drink. What would you like?"
"Oh, anything will do. I'll need to unload the car soon, because I need to get my computer and stuff out of the heat."
"Of course. Well, then, why don't we go do that. I can help you, then once you have your things settled, we can sit down and talk. You have no plans for later, correct?"
Chris smiled. He was pretty sure it wasn't a question. "No ma'am. I'm---(hestitating ever so slightly)---yours for the evening."
"Wonderful. Let's get on with it then."
It did not take Caroline and Chris long to empty his car and it did not go unnoticed by Chris that Caroline had no trouble whatsoever carrying one-handed his heaviest bags. He doubted he could take her if it came to something like that, he thought. Once unloaded, however, Caroline showed Chris Doug's and Gary's old room, which was now his, and let him spend a couple of hours unpacking and setting things up.
Finally, Chris came down. "All finished, more or less."
"Excellent," Caroline replied. "I've ordered some Chinese take-out for dinner, if that is all right. We can relax and talk and not have to worry about cooking or even cleaning up very much."
"Sounds great to me." And as if on cue, the doorbell rang and Caroline brought back the food---dumplings, fried rice, and a couple of meat dishes. They sat down to eat. Chris waited for Caroline to start the conversation rolling toward the elephant in the room.
"So, Christopher. Again, I'm delighted you're here. I've been looking forward to your arrival for quite some time. I think we are going to enjoy each other's company tremendously. But why don't you talk to me first. Why are you here? Why do you want to do this?"
"By 'this,' do you mean submit. . . become your sex slave?"
Caroline couldn't help but smile at the cute, naive young man at her table. She felt herself wet just thinking about taking all of that innocence from him. He would soon learn that his slavery was going to involve more than just sex. "Yes, dear, that is exactly what I meant," her eyes penetrating deeply into his soul.
"Um, yes, sure. Well, and I gather Heather must have told you this, and while I don't know why, but for as long as I can remember, every sexual thought I ever had was that I was with a strong, powerful woman who would completely dominate me, sexually. The fantasies changed over the years. At first, you know, when I was, say 12, I’d imagine older women, teachers, nurses, baby-sitters, whatever, who were clearly stronger than me, would simply force themselves on me. Rape me, you might say, but it was something I wanted. When I discovered the female domination stuff on the internet, it was so exciting!" Chris was rapidly growing more comfortable with the conversation as Caroline did not interrupt but nodded approvingly throughout.
"My fantasies took lots of different forms, with dominant women in lots of black leather or latex using bondage, whips, or whatever, and then using my body to satisfy their sexual desires. Sometimes it would be rough and hard, others soft and more sensual, but the woman was always dominant, always in complete control.
"Alas, it just never happened in real life."
Listening to Chris speak and knowing it had been more than a month since her last time with Gary, it was all Caroline could do to resist bursting up, ripping their clothes, forcing him to knees and brutally shoving his face into her crotch. "That is too bad. I think people should be true and accepting of themselves. I am a little surprised that more of the young women of your age aren't more inclined to be dominant."
"Oh, I think they are," Chris replied. "It just that it never happened to me. There were a couple of girls I knew in high school who I am sure like to sexually dominate guys, but if so, they liked doing it to the athletic jock types. And I am just not. While the girls who I think would have dated me, weren't."
"You probably should have given them a chance. You can't always tell. Look at your sister, for example."
Chris reddened a bit at the thought. He had no desire to discuss any aspect of his sister's sex life. And the one conversation they had had that hinted at was the one that got him to this house.
"Still, Christopher, you don't have to worry about that with me." She took his hand into hers. "You won't find me pining for some athlete. I very much prefer young men like yourself. The hulking jocks are usually too full of themselves and even if they weren't, I like being physically superior to my lovers as well."
Chris reddened some more at that thought. She thinks she can take me, too, he said to himself. Oh, it is what I have always wanted.
"Go on, Christopher. Describe your fantasies in excruciating detail. You must be forthcoming, no matter how embarrassing you think it might me. You must have no hidden secrets, fears, or desires for this to work." Caroline thought that that was not strictly true, but to know his fears was especially desirable, in part to avoid them or to use them for control.
Christopher thought for long time, before finally taking a deep breath. This is really happening, he thought, so, Chris, be careful what you wish for, he said to himself.
"Well, while the scenarios vary, the result is always the same. I am behind a closed door with a dominant woman who----"
"Stop. Don't gloss over how you get there. Describe some of them, even a little, before you go on."
"Okay, I'm in detention with a teacher, who takes advantage of the situation. Or I am pulled over by a female police officer for a traffic ticket. Or I spend the summer with an aunt or older cousin. Or I have a girlfriend who is dominant. Or a neighbor who seduces me. Really, there have been so many."
"Very well, Christopher, go on then. What happens behind the door?" Caroline made a mental note of this. If Chris proved game, then they could do play-acting when they were together sometimes. She had a mean looking policewoman's outfit, for example.
“Well, uh, I imagine she completely dominates me. She rips off my clothing, she forces me down to my knees, she ties me up, I am forced to worship every part of her body, but especially her pussy, she torments me in many different ways before she rapes me."
Caroline wanted to hear more details, but it was clear that Chris was having a hard time giving them. No matter. She heard all she needed for now. Chris appeared to be a true submissive, a man born to the need to be sexually dominated by a woman. She would love exploring the rest of the summer just how far this could go.
"All right, Christopher. Let me explain some things. I will give you what you crave, what you so desperately need. I will dominate you, but not only when we have sex, but mentally and physically as well. You are to be my slave in this house. You will do almost all of the chores around the house, such as the cleaning and gardening. You serve as my body servant as well, brushing my hair, polishing my toenails, giving me daily massages, washing me when we bath. You will spend all of your time in the house either naked or wearing whatever frilly clothing I give you. Outside, at college, you may keep your secret, although you will still wear what I tell you under your outside clothes. Do you understand?"
"Yes ma'am."
Caroline then explained to Christopher that he would face discipline for failing to obey her and probably would be disciplined occasionally even when he did. "Does that frighten you Christopher?"
"No ma'am."
"Really?" Caroline was a little disappointed and taken aback by this answer. She liked inspiring a little fear in her slaves and she could always count on the threat of physical discipline to have the desired effect on Gary.
"No ma'am, I think I would like it. I always kind of enjoyed it when my Mom spanked me as a boy and when she thought I was too old to spank, I used to provoke my baby-sitter into doing it."
(Christopher flashed back to when he was 10 and his 16-year baby-sitter, Melissa, finally acted to spank him after pushing her just a little too far. She had actually apologized afterward, fearing she would get in trouble when he told his parents. But he never said a thing and actually made a point of saying how wonderfully the evening went with Melissa in front of her. But then he would do it every time she came over, and she would finally be forced to spank him again to "calm" him down. After several such occurrences, Melissa figured out that he liked it and asked him after finishing spanking him the fourth time it happened: "Chris, admit it, you like it when I spank you, don't you? You're deliberately provoking me to do it, aren't you?" Chris had answered, "yeah, I do. I don't know why, but I do." "It's okay, Chris. Tell you what. You don't have to be such a brat when I come over. You be good, we have some fun, watch tv, and I'll still give you a good spanking. Do we have a deal?" Chris had given Melissa big smile and hug after that and, true to their deal, Chris always behaved after that and Melissa always gave Chris a good spanking before bed-time, until Melissa went to college and Chris was then too old for a sitter. It was more fun than he ever had when Heather sat for his parents, which wasn't often because she usually liked to go out on Saturdays.)
Caroline smiled quite broadly. "Christopher that is just wonderful! I think you and I are going to get along very well." They had finished eating. "Why don't you clean up and then we can enjoy some one-on-one time." Chris smiled nervously and stood up. Caroline could see the outline of a massive erection in Chris's pants and even a small wet stain, showing he had been releasing pre-cum throughout dinner. As Chris made to pick a few things up, Caroline stopped him.
"Chris, it begins now. Strip. I want you completely nude."
Reddening again, he simply answered: "yes, Mistress." Chris unveiled a solid, wiry body as well as an erection so hard that it stood up, pointing toward the ceiling and almost never bobbed downward as he worked.
When he had finished, Caroline ordered him down. "Another rule. Unless you have reason to stand, you crawl in my presence in this house. Now follow." Caroline's voice was matter-of-fact, rather than stern. Caroline led Chris up the stairs, past his room and to the hall bathroom.
"Chris, you may stand up now and go take a shower. I wish to take one as well, but we will do it separately for the moment. I will use my own bath. In precisely 30 minutes, you will crawl down to my room and enter without knocking. Exactly 30 minutes. Understood?"
"Yes, Mistress, I understand." Chris then stood up and headed into the bath where he found white, fresh towels waiting for him as well as soap and shampoo. As he showered, he felt much more excited than apprehensive. Caroline seemed like a nice woman---she certainly gave him no reason to think otherwise. And he found her incredibly attractive, just his type: tall, older, beautiful hair, and clearly a firm body. Chris was an "ass man" and there Caroline did not appear to disappoint as well. Her cheeks were tight and rounded from what he could observe through her clothes. He thought that this was impressive for a woman in her forties.
It was all he could to keep from stroking himself in the shower. He took a long, hot shower and that did nothing to shake his constantly raging erection. His spun out a thousand scenarios of what he thought would come next. After he finished, he took a long time drying himself, to burn up as much as the 30 minutes as possible. He was now impatient to continue but knew that "precisely 30 minutes" clearly meant just that.
Finally, 30 seconds to go, Chris got back down on his hands and knees---naked---and crawled out into the hall. When he reached Caroline's room, he found the door slightly ajar and entered the room.
If it was possible for Chris to get even more excited at this second, he did. As he entered the room, it was decorated in red and black. Hanging from the walls were a variety of pictures and artwork that showed men being sexually dominated by women: bound, whipped, and kneeling before mistresses. In the center of one wall was a large armoire, whose doors were wide open, revealing a variety of whips, bondage devices, and leather clothing. In the center of the room was a king-sized bed with four posters with chains and handcuffs attached to them. From the ceiling over the bed, hung a number of chains in different positions. Other than those additions, the bed itself was made up of normal sheets and a comforter, though ones consistent with the decor of the room.
Caroline herself was sitting in a large chair in the room. No longer wearing a satin blouse and pants with boots, she had kept the boots on, wore a black leather corset that zippered in the front, and her hair was clearly done up in a bun and hiding under a black, policeman-like hat. Everything else above and blow the waist was exposed. Chris believed her to be the most beautiful thing he had ever seen.
"You look absolutely beautiful, Mistress."
"Why, thank you, Christopher. You look very handsome yourself, and it has been some time since I had a young man in this room to take advantage of. Come here. Let met get a good look at you."
Chris crawled over to Caroline and sat up, but remained on his knees. She stood up and walked around him, touching him constantly about the head, shoulders, arms. As she did so, she put a black leather collar around his neck. "This is a sign of your status to me," she said. Finally, she squatted down in front of him with the leather of her boots aching with every move she made. Caroline grabbed Christopher very firmly by his balls, not enough to really hurt but enough to make him suck in his breath. With her other hand, she grabbed a fistful of his hair on the top of his head.
"This is where we begin, Christopher. So long as I wish to have you and you wish to be here, I can do anything I want with you. Your cock and balls are my property to use and restrain as I see fit. Your head and especially your mouth are here for my pleasure. All of these parts of your body will get a daily workout." Without letting go, Caroline asked: "Do you understand?"
"Yes, Mistress."
Caroline felt like a kid in candy shop. It had taken her months before she felt she could be so direct, so bold, and so controlling with Gary. But Chris's ready-made orientation allowed her to by-pass that training stage with Gary. All she had to do was not be too severe so as to frighten the boy off, but so far, based on how hard his cock felt in her hand, there seemed to be little chance of that.
"You are so delicious, young man. Come let's get started. Stand and come over to the bed." Caroline released Chris and walked over to the bed, unzipped her corset, and lied on her stomach. Give me a massage, all over, until I tell you stop."
Christopher got to work, and for the next half hour gave the best massage he knew how. Caroline encourage him repeatedly, telling him what she liked, and when and where to do more. The feeling of a young male's hands on her body in service to her was one she relished and never, ever tired of.
Finally she ordered him to stop. She turned over and got into a sitting position with her back against a large stack of pillows against the headboard, spreading her legs wide. She wanted to do so much with Chris tonight, but right now she wanted some immediate relief.
"All right, Christopher. I gather from our conversations that you have never eaten a woman's pussy in your life, am I right?"
"Yes, Mistress. But it is something I have always fantasized about."
"So you have told me. Well now it can be reality. Indeed, worshipping my pussy will be one of your core responsibilities almost every day. Lie down and position your mouth here," she said pointing to her crotch.
Chris approached almost reverently, longing for this day for as long as he could remember, but a little uncertain as well. Caroline's vagina was neat and trimmed, invitingly so. And once he got near it, found it fresh and clean smelling after her shower, though emanating moisture from her excitement. Caroline lifted her thighs slightly to allow Christ to slide his hands underneath her buttocks. Once that done, however, Chris felt Caroline's leather booted legs close around his body and lock behind his back. She had a very firm grip on his position that indicated he was not going anywhere. Still, it felt really good, comforting even, as if that was where he was always meant to be.
"Since you have never done this before, I am going to start off by giving you some instructions. But I expect that pretty soon I will just take over and we'll have to continue the lesson later."
Chris was not at all sure what that meant, however, but he figured he would soon find out.
"Begin by licking the outside, Christopher. Start off slowly, with short licks, but then gradually increase your strokes until you are licking with long strokes from top to bottom."
Chris did his best to do exactly what Caroline said. In return, he was rewarded with various sounds of pleasure, moans and groans from his Mistress. Her hair down there was not as soft as he expected but nor was it unpleasant. The more he progressed into his rhythm, the more he enjoyed giving so much pleasure to Caroline. And while he did his work, he noticed Caroline would tighten her legs around him from time to time and she never let go of his head with her hands, although neither was she hindering his movement.
"Ohhh, ohhh, yes, wonderful, Christopher. You're doing very well!"
Chris thought he spent a good 10 minutes at this activity before Caroline gave him further direction.
"Now then, stick out your tongue as far as you can and push it inside. I literally want you to fuck me with your tongue."
Chris dutifully complied. He angled his head down a bit and pushed his mouth as much as possible into Caroline's vagina.
"Swirl your tongue around in there!" Caroline's voice was rising and getting a bit more excited.
As Chris moved his tongue, he noticed a change in Caroline's actions. She was increasingly moving Chris's head with her hands, pushing him harder and into her. Soon Chris realized that for all intents and purposes, Caroline was masturbating herself using his face. She was rubbing his mouth and nose against her pussy reducing dramatically the amount of air Chris was able to take in. As he attempted to move or resist that a little in order to catch a breath, Caroline locked her legs even more tightly around his torso, if that was possible, to prevent him from moving away from her even a millimeter.
And the more Caroline pressed Chris's face into her pussy, the tighter the seal her lips made around his mouth and nose. Increasingly, he was finding it difficult, if not impossible to breath at moments and this caused him to struggle a little harder to free himself a little. But he also never felt so turned on in his life. Here was the ultimate moment he had always fantasized about: a taller, stronger woman who was completely dominating him and using him as her sexual plaything.
For her part, Caroline loved the position she (and Chris) were in. Moreover, the more Chris struggled to escape her grasp, the more turned on she got and the more roughly she used his face as her dildo and the more tightly she locked and squeezed her legs around his body, making it virtually impossible for Chris to move on his own, much less escape her control. It wasn't long like this before Caroline came, which was a good thing for the last minute Chris was completely unable to breath and completely unable to do anything about it.
"AAAAAAAHHHHHHHHH! Yes, oh YES, God, Christopher, that was so good!" Caroline relaxed her grip on Chris's head, who immediately pulled back and sucked in air. "Not bad at all for your first time. But the good news is that we will have lots of time to perfect your technique. Here." Caroline handed Chris a face cloth to wipe his face, after using it on herself, which he did. "What about you?"
"Caroline, I have never been so turned on in my life as I have been since I arrived here today. I absolutely love worshipping your pussy. It was better than I had ever dreamed it would be, but . . ."
"But what?"
"Mistress, may I please have some relief? I am so turned on it actually hurts."
Caroline thought this a good idea. They were less than an hour into what she expected would be six hours of dominant female lovemaking, but she was far from ready to take his slave virginity from him, especially since she had just come. "All right Christopher," she said getting up. "Lie down on your back." Chris did what he was told and Caroline then chained his legs to the bottom four posts of the bed. "Now, I want you to make yourself cum, but don't release until I tell you to." Caroline thought this hilarious as she seriously doubted Chris would be able to restrain his orgasm much at all the minute he started to touch himself. And sure enough, that is what happened. While Caroline ordered Chris to stop a couple of times, the next time the slightest touch started his eruption, which Caroline ordered him to finish.
"You did not wait for my permission," she accused.
"I am so sorry Mistress, it's, it's just that right now I feel like I have very little self-control, especially in your presence." Chris meant that with all his heart. So far, the time he has spent with Caroline was far better than he ever imagined, but he felt chagrined that he could not contain himself when told to do so.
"Yes, well, nevertheless, it appears some appropriate discipline is in order." Caroline unchained Chris's legs, sat on the bed, and ordered Chris across her lap. She began spanking Christopher and, to test what he had said earlier, did not go slowly or erotically at first, in the way she had done so with Gary. Chris was getting a more traditional spanking: Smack! Smack! Smack! Smack! Smack! Smack! Smack! Smack! Smack! Smack! She then stopped and noticed Chris's cock hardening again between her legs. So, she thought, he wasn't fooling. He's got a bit of masochism in him. Wonderful. And she promptly gave Chris 10 more. "Now thank me for it. You clearly seemed to enjoy it."
"Thank you, Mistress. Thank you for spanking me for not following your orders."
Caroline ordered Chris back down on the bed where she stretched and tied all four of his limbs to the four-poster bed. Caroline then lied down beside Chris, where she began kiss her new young slave quite passionately. Caroline always enjoyed kissing and enjoyed teaching Gary how to do it right. Chris appeared to be more of a natural at it, so she enjoyed that for a long time. As her kissing continued, she worked his nipples over, eliciting small moans and groans of pain from Chris.
Slowly Caroline moved herself on top of Christopher, so that she was lying on top of him. In her bedroom mirror, Caroline could see that her taller, somewhat larger frame seemed envelope Chris's smaller profile, as if she were consuming him. It was a thought and image that excited her, because that is the way she felt: she was continue to consume Christopher before she was through, consume him in a sexual, animalistic sense. She slid up his body until her breasts were positioned over his, like large melons dangling from a vine. She lowered her right breast to Chris's mouth just enough so that it pressed his face into a the pillow a little, while at the same time she slid her hand behind his head and pushed his mouth onto them. She did not speak. There was no question what Chris was to do.
And do so he did eagerly. He licked, lapped and sucked Caroline's breast for what seemed like ages, causing her to elicit a number moans, groans, and sounds of pleasure. When one was done, she moved the other into position for equal treatment. And when that was done, Caroline began to play with Chris's face with her magnificent breasts, at first slapping him with them but eventually and repeatedly pressing Chris's face into her overwhelming cleavage, cutting off his air for increasing amounts of time. At first it was for a few seconds, but as she increased the time, there were moments Chris grew uncomfortable at this lack of oxygen and would suddenly struggle to gasp some air. It was this struggle for air in panic that Caroline loved and she sought it repeatedly, smothering her breasts on Chris's face for up to 90 seconds at a time over and over, as each time ended with Chris struggling to escape, but Caroline knowing he couldn't if she didn't want him to.
After more than 40 minutes at her breasts, Caroline sat up and turned herself around. Planting her almost equally magnficent ass on Chris's face, she ordered: "Lick and worship my ass Chris. You must pay homage to every part of my body." Hesitant at first, but soon with little choice, Chris stuck out his tongue and ran it up and down her crack before plunging it in. He was surprised to find it did not smell or taste bad because Caroline had showered before they started. As a consequence, he was more turned on than ever, with his cock having returned to a permanent hard-state during the breast worship session. Caroline then played the same breath control game, except with her ass, savoring Chris's struggling beneath her to breathe when time was running out.
Finally, after what seemed like an eternity to Chris, Caroline got off from her slave and went to her lingerie chest, pulling out a small object. "Time for the main event, Chris, but despite granting you relief earlier, I detect you're enjoying this still a little too much for my taste. This is a cock ring." She held up a small silvery circle. "Once I put it on you, you will find I will be able to fuck you but you won't be able to come, at least not until I remove it." Caroline slipped the ring over Chris's engorged penis pushing down the base where it rested snuggly. "This will allow me full satisfaction before giving you yours."
With that, Caroline climbed back on top of the boy and holding his cock in position, impaled herself on him, pressing him hard into the bed. For Chris, it was a dream, a fantasy of a half dozen years come true. He was tightly bound, completely dominated, being fucked by an older, taller, stronger woman that he longed for. The sensations were warm, velvety and utterly delicious. Caroline at the same time was reaching her state of ecstasy: she had a new, young slave, who truly craved what she offered and was now going to be able to screw him until she was satisfied. And so she did. For better than a half hour, Caroline rode Chris's cock, bringing herself to multiple orgasms. A number of times Chris felt sure he was going to come but the cock ring held back completion, leaving a sense of frustration in its wake every time he felt he was getting close.
Finally, Caroline dismounted her slave. She grabbed a cloth from the bathroom soaking with icy cold water. When she applied it to Chris's cock, he screamed in shock, and she laughed in return. "If you want to come, the ring has to come off." While it took a minute, Chris's cock finally wilted enough so Caroline could take the ring off. With a brush or two of her hand, she made it erect again. As she made to mount him again, Caroline said, "here it comes Chris, enjoy." Caroline slid Chris's cock inside her and within just a few strokes of her vagina, Chris screamed his orgasm: "AHHHHHHH, OHHHHH, GOD!" And Caroline felt him shoot inside her for a long time, as he bucked and strained against his bonds.
When they were finally all done, Caroline released Chris and they took a shower together, where he was required to bath and pleasure her just a little more with his mouth. Having a male worship her pussy on his knees in the shower was something Caroline always loved.
After they were cleaned and dried once more, Caroline turned up the thermostat in the room to 78 degrees and put Chris's collar back on. She put a sexy top on herself as well as a crotchless pair of leather panties with some eye-rings attached to them. "You'll sleep in my bed, Chris, but only in ways I permit," she said as she lied down. "Come here." Chris, completely naked except for his collar, climbed onto the bed. Caroline sat up, grabbed a fistful of Chris's hair, bringing his head over to her groin. Then, with several hooks, Caroline attached Chris's collar to her panties, so that his head rested on top of her pussy, in a sense becoming his pillow. Caroline then tossed a blanket on Chris and one on her own torso, leaving the boy's head and her groin to steam in the open air. It was not the most comfortable arrangement for either of them to sleep, which probably explained why Caroline forced Chris awake several times for more pussy worship and once more to fuck him, but always returning him to that position. As inconvenient as it was, Chris never slept more contentedly.
Caroline had awakened in the morning and actually dislodged her exhausted slave to go make breakfast without waking him. Once ready, she rousted Chris with a few smart smacks to his exposed ass. After they had finished breakfast, Caroline told Chris: "It is time for you to begin your chores. The house needs a good cleaning. It should take you most of the day. You'll find all the cleaning supplies you need in the laundry room. But before you begin, come here." Caroline then pulled from a kitchen drawer a few items she had placed there yesterday: a hood and some leather straps. Caroline first connected the black cuffs Chris was wearing together. Then she put the black hood over Chris's head. It laced tightly in the back but had openings in the front that allowed him to see, breath, and speak---if Caroline wanted. "I know it will be harder for you to do your job handcuffed like that, but I like the constant reminder of your status."
Chris thought: how could I forget? but simply answered "yes, Mistress." He had read enough femdom porn over the years to know that "yes, Mistress" and "no, Mistress" were the words he'd be using most often.
With that, Caroline put the small gag of the mouth piece into Chris's mouth and strapped that closed. He could no longer effectively speak. The gag was not so tight however that he could not move it around or swallow saliva. Finally, Caroline attached a peculiar device to his genitals. The black straps were very thin and went around his legs and buttocks. They then attached to two small circular straps, which themselves could be tightened. Caroline fitted the small circular straps over Chris's cock, one near the head, the other two-thirds of the way down. She then attached the long straps to the loops on two sides each, pulling the whole package painfully snug. It had the effect of restraining his erect penis and forcing it to lay fairly flat against his groin. The same effect would have been occurred if he had had an erection inside a jock-strap, the difference being his cock was in full view. He realized he wasn't in a chastity belt really, but his cock was in bondage as well.
"Now, get to work."
Throughout the morning, Chris proceeded to clean Caroline's house. It was a slow process at times, in light of the restrictions he was under, but he gradually got the job done. Caroline, fully decked out in leather boots, pants, and halter watched him workall day, as she read, watched tv or relaxed. She held the leash, a long riding crop, and a cat'o nine tails with her the whole time, regularly checking on Chris's work or suggesting improvements, always touching him as she did or a stroking him as she simply walked by, especially when his focus on his work actually led to a softening of his erection. She knew it wouldn't stay in position all the time, but she tried her hardest to keep him hard all day long, this first day.
About mid-morning, having watched the arousing sight of an 18-year male serve as her slave, cleaning her house handcuffed and gagged, wearing nothing more than a slave hood, Caroline ordered Chris over to her and made him kneel in front where she was sitting. She unstrapped his gag, unzipped her pants, pushing them down just enough give Chris access, ordering him to bring her to an orgasm. Chris embraced that chore with relish, much preferring it to cleaning. Caroline did not control Chris's actions so much this time, as she had the previous night, preferring to let him go about it and bringing her off twice in a 20 minute period.
Caroline then made lunch while he worked, but Chris was required to serve it to her and clean up afterwards. Chris resumed his chores after lunch with Caroline moving with him from room to room to watch. This was something Chris did not mind at all. He utterly enjoyed being Caroline's slave so far. As he worked, he reflected on how a mere 24 hours earlier he was simply driving his car to "college." It was if he had entered a different universe and he never wanted to go back. The more Caroline looked at him lustfully, the more he enjoyed her dominion over him.
But Chris was not paying attention to his work when he accidentally knocked over a glass vase in the living room. Of course it broke. Caroline looked up immediately. She was quite annoyed. "Well, wasn't that stupid of you. First, go clean it up!" Chris left hurriedly and Caroline thought, it is really no big deal, but I might as well have some fun with it. After Chris finished picking up the glass and vacuuming up the small pieces, Caroline said: "Those kinds of mistakes will be punished Chris. Come here."
Chris crawled over to Caroline, who by now had the leash and cat in her hand. She attached the leash to his collar. "Put your head to the ground." Chris did as he was told, and was now a very prostrate position with his buttocks in the air. Caroline then planted he heel of one of her boots on his neck, pulling the leash so tight, it choked a little. She then began whipping Chris. She thought: Let's see how much of a masochist he really is. She gave Chris 40 strokes this way and found to her considerable delight that by the 25th stroke Chris screamed out in pain with each blow. Clearly I do have a disciplinary option that he doesn't love, then. She covered his back and buttocks with red welts.
Chris found himself very afraid of what had happened, because Caroline was clearly incredibly angry, or so he thought. More than anything else, he momentarily thought he had put their arrangement in jeopardy. He then realized that that was unlikely, but worried about his punishment. When he realized what would happen, he was afraid. Spankings were one thing, a full whipping another. At first it was exciting but as the whipping went on and the sting of more and more nerve endings could be felt, he did not like it. Eventually he was screaming with each blow, hoping it would stop, but still gagged and unable to beg Caroline to stop. When she did, it felt as if his back and bottom were on fire.
Caroline removed his gag and hood. "Don't worry, there's no permanent damage, not even broken skin. You'll be sore for a day or two, but it'll start to feel better in a few hours. Lay down on your back."
"Yes, Mistress. Thank you, Mistress. I am so sorry, Mistress," Chris pleaded. He then did as he was told, even though the carpet fibers against his welts was extremely painful.
Caroline then unzipped her pants and lowered them to her ankles with her panties. She then immediately planted herself on Chris's mouth. Caroline had been intensely turned on by both whipping Chris while he was pinned prostrate to the floor and by the welts that remained on his body. She had rarely subjected Gary to such punishment, because he couldn't take. He had nearly left for good when she had done this to him one time, but she talked him out of it. And while she disciplined again, she had not ever gone so far again. If only Gary had understood how excited it made her.
Chris stuck out his tongue and went to work, inwardly relieved that Caroline wanted him right away. But for all intents and purposes, Caroline controlled it all. She grinded her crotch against Gary's mouth and nose, and rode his face to two more orgasms before she got off and ordered the boy back to work.
God, how I am going to love the next four years! she thought.
By early evening, all the work was done. Caroline and Chris showered together again. He washed her body as he had the night before, licked Caroline to more orgasms while on his knees and the water poured over him. Caroline, however, used a soapy hand to bring Chris off as well. She decided to take them both out to dinner, to celebrate the past 24 glorious hours, knowing there would be many more to come.
The restaurant Caroline chose was an elegant one, with fine dining and dark lighting. She insisted that Christopher wear a suit, and of course he complied. The restaurant was designed to enable intimate conversation if so desired.
Caroline found to her delight that Christopher was an able conversationalist, able and willing to talk about a variety subjects at length with her. She wanted to enjoy his company outside of the specific reasons he was in her home, and now she knew she would.
By the time dessert rolled around, Caroline steered the subject back to their relationship, finally asking: "So, Christopher, I have very much enjoyed myself over these past 24 hours. Have you? Has it been what you hoped for, what you expected you were getting yourself into?"
"Oh, man absolutely! Honestly, Caroline, this has been better than my fantasies." He hesitated a moment before going on. "I mean, I wish I weren't wired this way, but I am, and I have loved every minute of it---well, almost every minute." He shifted a little uncomfortably on his welt-tracked buttocks but smiled while he did so.
"So, you never did any of this before?"
"No, not really. I have had girlfriends but they really weren't into this. Ironically, the closest I ever came to this experience was when I ran into my old baby-sitter in the mall parking lot a few years after she last sat for me."
"Really! Tell me about that," Caroline was intrigued by this sudden revelation.
"Well, it wasn't much, unfortunately, but it was enough to hold out hope for a relationship with a dominant woman one day."
Chris Tells His Story
”I was leaving the mall one day, after parting with some friends of mine when I heard a voice call to me. It was Melissa, my old baby-sitter, calling me from her parents’ minivan, but she was alone. She was home visiting after having just finished college. I was 16 at the time, which made her 22. She wasn't the prettiest girl in her face but she was built. This was how I remembered the conversation:”
"Hi Chris! Do you remember me? It's Melissa, I used to babysit you."
"Oh, sure, it's great to see you! How are you doing, how is college?"
"Just graduated. In fact, I'm headed to New York tomorrow to start a new job there. I majored in finance and I'm going to work on Wall Street. You?
"That's great. I'm doing fine. Just winding my way through high school."
”At this point, there was a moment of silence in the conversation, as if neither of us knew what to say next. I remember being totally shocked at what she said next.”
"So, you find a nice girl to take up where I left off in giving you regular spankings?"
I'm sure I turned beet red at that and I just stuttered after that: "Uhh, uh, n- no. You remember that, huh?"
"I babysat a lot of kids over the years, Chris. You were the only one who wanted regular spankings. It is kind of hard to forget."
After a long pause again, she asked: "Would you like one more---for old times sake?" I remember how she just stared right into my eyes, it felt like she was penetrating to my soul, and she had the slightest curl on the sides of her mouth. I am not sure she truly cared what my answer would be but she clearly liked asking the question, putting me on the spot. The answer, though, was a no brainer.
"Uh, yeah, that would be fun, if you want to."
"Okay. Walk away for a minute then come back and enter the van by the side door."
She didn't get out of the car and I did what she said. When I climbed in, I saw that she had folded some of the seats down to make some room. And she was clearly waiting for me.
"Close the door, Chris. Lay across my lap."
After I did that, she started to spank me. "You know, Chris, I've missed baby-sitting you. You were always my favorite. Truthfully, I enjoyed spanking you as much you enjoyed having me do it."
After about six blows, though, she stopped and said: "You know, I think this will be more fun for us both if you dropped your pants. Let's make this a bare-bottomed spanking, truly like old times." So I did, but the difference between 10 and 16 was that now I had a raging hard-on. But obviously she knew that and liked it, and was one of the reasons she had me drop my pants. I was mortified and excited at the same time. I felt like should leave and couldn't at the same time. At the time, Melissa was the one person who knew about this. And I frankly trusted her a lot, after all those experiences with her baby-sitting. She made it easy, too.
"Don't be embarrassed, Chris, I've seen hard cocks before. Common, let's continue."
So I laid back down across her lap, with my pants and underwear pulled down. She nestled my penis between her thighs and continued spanking. Hard, but not too hard, she wanted it to go on a long time, nor did she seem to want either of us to make a lot of noise. Good thing the car had tinted windows. She didn't say much, but she would murmur from time to time things like "this is what you want" or "this is what you need" or, and this I remember clearly, "I like it, too, Chris." After about 25 more strokes, she started to rub her thighs together---with my cock in between. As she did so, she picked up the spankings and made them a little harder. Well, needless to say, with a few more strokes I came, all over her car floor. When I stopped, she stopped, and said:
"Pull up your pants, Chris."
"I'm sorry about that but---"
"Shh, never mind about that. It's not a problem." She looked at me, gave me a kiss on the cheek, and said: "If only you were a few years older."
She then told me to open the door and get out of the car. We said our good-byes and she drove off. I went home and have never seen Melissa again.
Caroline finally spoke, after being mesmerized by this tale. "She sounds like a wonderful, generous person Chris."
"Yes, I guess so. She certainly understood me and I will forever remember that day in the parking lot."
"I would think so."
At that point, Caroline got the check, paid for dinner, and mistress and slave drove home. In bed that night, Caroline took Chris twice more, although a little more intimately and with a little less dominance than the previous day would have suggested.
That became the routine in the Barron household over the summer. Christopher did all the chores around the house and served Caroline her every whim. He was used and abused sexually several times a day, punished for cause and punished for no good reason. They played many games together, with Caroline trying to act out the various fantasies Christopher had about policewomen, teachers, relatives, even baby-sitters. When Christopher's parents came for visit, Caroline was nothing but friendly and proper, no hint whatsover of the real nature of their relationship ever came out. By the time school started in the fall, Christopher was Caroline's slave more completely and more thoroughly than Gary had been. There was almost nothing Christopher wasn't willing to endure to please his mistress. The amount of sex that was going on would have put a rabbit colony to shame.
And on the night after Chris came home from the first day of classes, as he lay kneeling on the floor, with his arms strapped to his sides, and his head inside her short black leather skirt, firmly clamped between Caroline's thighs, Christopher thought to himself just how good it all felt, how right: the prostrate position, the bonds feeling like caresses, and with nothing in his sightline but Caroline's pussy. He felt so completely at peace, that there was nowhere else he wanted to be and nothing he would rather be doing more.
For herself, Caroline thought how incredibly lucky she was to have a devoted slave for at least four more years---and in Christopher's case, maybe a whole lot more. . .
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