SALLY'S RELUCTANT CROSSDRESSER

CHAPTER ONE

       

       Sally and Dave had been dating since high school, it was a turbulent relationship, and at this moment in time they were having a few arguments, Sally called them dicusions. They were both nineteen and in love with each other, and both were jealous and possessive of each other. Sally was the one with the ideas, and Dave let things fall into place as he could never emulate her suggestions. They were sitting in the lounge of the flat they rented, they were not married but in a good relationship. They were both the same height at about five feet ten, both slim and Sally’s curves were something to behold, and very pleasant to the eyes. “Don’t forget Sally, I have to go to my mother’s this afternoon, I cannot get in my clothes cupboard, the keys are in my other jacket, and that was left around there yesterday. Why did the builders put locks on wardrobes I have no idea, they must have had a warped sense of humour?”

“We can go there after we have been to the shops, but I have to get some new shoes first.”

They had been walking around town for a while when one of Dave’s mates met them in the high street. They were chatting for a while leaving Sally out of the conversation, “Come on Dave it looks like rain and we don’t want to get caught up in the downfall.”

       Dave’s friend looked at him and asked, “Do you always do as she says?”

       Dave went red in the face and answered “No of course not, just wait for a moment Sally until I have finished talking.” These were the wrong words to say to her, and when Dave glanced at her out of the corner of his eye, her look said it all. His face went red once more, and he said quickly, “Damn, I have just thought I have to collect a key, Sally is right and we must go.” He knew though that the damage had been done, and the last time he had upset her, it was as if, Pandora’s Box had been opened, and her face was looking like the Devil had possessed her. Dave was not frightened of Sally, but he was frightened of her temper, and she was very domineering when she wanted to be. He also knew that he would be held to ransom now, and there would be damn all he could do about it, he was also in no doubt that this time it was a big mistake, and his penance would be high.

       It could only get better or so he thought, and he went to put his arm around her back, but she pulled away, at the same time giving him a cold look. “Don’t for one second think you can get round me like that, you humiliated me, treated me like a second class person. You big head, just like you, doing all that your mates tell you, what’s up did I eat into your ego? Well after I have finished with you, there will be no ego to damage, so you had better prepare for the worst because it is going to happen.”

Rather nervously Dave asked, “What do you have in mind lover?”

“Don’t you call me lover, you have just lost that right, and I am not sure what I will do to you, but it won’t be very nice I can assure you of that.”

They walked around to his mother’s house, but it was only to be told that she had gone away for the weekend, and there would be no one there until Monday. “Now I will have to stay in these clothes all weekend, what a flipping mess.” It was just then that there was a crash of thunder and the sky’s opened up, within two minutes he was like a drowned rat, and so too was Sally.

“You see if you had walked on like I said big head, this would never have happened. Well it serves you right, and this is another thing that I will punish you for when we get home. I’m drowned, because you wanted to be the macho man, but I have just thought of something very funny that has cheered me up.”

“What’s cheered you up Sally, you’re drowned and so am I, so tell me and cheer me up?”

“No, you’ll have to wait and find out.” She laughed as she walked just in front of him, and he followed behind with misgivings.

It had taken just over an hour to walk from the west end of London to the house, and they were both saturated. Sally ran to the bedroom and Dave walked to the toilet, five minutes later she was sitting in the lounge smiling. She watched as Dave walked out of the toilet and bathroom naked, and there was now a bigger smile across her face. She heard him shout out, “Bloody hell, I’ve got no clothes to wear, now what the hell am I going to do?”

Sally smiled once more and then shouted, “What’s up Dave is there something wrong?”

“What’s up Dave is there something wrong,” he mimicked “Of course there is something wrong, I will have to walk around naked for the rest of the evening, because I can’t get into my wardrobe.”

Sally was sitting on the couch laughing and she said through her tears, “Oh good.”

“What did you say, I couldn’t quite hear you?”

Still laughing she answered “I said oh dear what a pity.”

Dave walked out of the bedroom covering his genitals with both of his hands, “What the hell is so funny, for god’s sake help me out.”

She stood up still laughing, “You had better come into the bedroom and I will see what I can do.” Dave followed her, as there was nothing more that he could do. Once inside she went to her wardrobe, and pulled out a dress and walked over to him. His eyes now were like pigeon eggs, and he backed off, but she pressed it against his body saying, “Yes flowers really suit you Dave.”

“I’m not putting that dress on, and that is all there is to it.”

“Shut up! You will do as I say you asshole, you humiliated me, and now it is my turn to do it to you. Put the dress on or you can kiss me goodbye, because you owe me big time.” She threw the dress at him and went back to her wardrobe, when she walked back she handed him a pair of yellow briefs. “You had better put those on as well, because I don’t want to look at your prick all night.”

“Please Sally, haven’t you got any jeans?”

“Yes but they won’t fit you, now get a move on I want to see how you look, I’ll bet you will look very sexy,” and she once again laughed. She watched as Dave reluctantly put the clothes on, and as he put the briefs on she could see the bulge in the front. Once he had completed the task, pure devilment made her walk over and put her arms around him, then pulling him tight she rubbed her body against his crutch. Sally could feel his hardness through her own clothes, and as she pushed him away, again she laughed. “I think you like wearing my clothes Dave, because that is one hell of a reaction to wearing my knickers. Do you like wearing my knickers Dave,” and as she spoke softly to him she was giving him a little smile.

“No I don’t, how could you ask such a silly question, I’m a man and men don’t dress like this.” Sally could see that his face was now bright red, and she couldn’t help smiling more, well to be truthful it was a grin. My clothes will have to be washed and dried, I will have to use some of that money we won to buy new clothes, and it’s a damn good job I get an allowance from my father. I suppose the only lucky thing is, that tomorrow is Saturday and the shops will be still open.”

             They were a very lucky couple, in the fact that neither had to work, Dave’s

Parents were middle class with money of their own, but they had split up when he was ten years old. His father gave him a large allowance every week, but his mother thought his father was a cheapskate and gave him more. Sally had been given an inheritance, and received dividends from shares that had come with the inheritance. Sally looked at Dave and said “You had better go and dry your hair or you will catch your death from cold.” As Dave turned to walk back to the bathroom, Sally couldn’t help herself, she patted his buttocks and said, “Mnnn, nice ass love,” and laughed when she saw his face go a scarlet in colour.

It was twenty minutes later when he walked back out, the hair dryer had fluffed up his hair as it always did. Dave’s hair was blonde, and when washed and shiny, it had that same sparkly tint; his hair was also long and come below his neckline. As he sat next to her on the couch, Sally looked at him and smiled. Dave felt her eyes, and turned to look at her, and in a questioning voice asked “What?”

“Nothing lover,” Sally answered.

“By calling me lover, does that mean you have forgiven me Sally?”

“God forbid no, I said that because you are, but your punishment has not started yet, as I still have to find the correct solution.”

       “Err umm, is this punishment going to be hard Sally?”

       “Of course it is silly, that is what punishment is all about, it might be hard or it might be difficult, but it will be humiliating. It has to be, to compensate me for your indiscretion, and insult to my femininity. Your disgusting behaviour this afternoon, where you publicly displayed your chauvinist ways has to be dealt with before we can move on.”

       “Listen to you, you never by any chance swallowed a dictionary while in town today, you’re beginning to sound like my mother, and she’s a local councillor. What do you mean by humiliating, are we talking about public or private?”

“We are not talking about anything, it is me that is talking about it, and you will know what it is all about when I am ready to tell you. I do think however, that there should be some sort of public humiliation, after all that big mouthed mate of yours will have spread it around, that you chastised me in public.”

“I never touched you Sally.”

“I’m talking about verbal chastisement, sometimes I wonder if you were in the same class as me at school. I was just wondering how you were going to walk down the chip shop like that?” She smiled as she watched his jaw drop, “Well I suppose that is asking a lot, so I had better do it, but that is something else you will be punished for, not doing your weekly chores.”

“How can you punish me for that, I can’t go out dressed like this, and it is not my fault that I haven’t any clothes to wear.”

“You really are adding to your punishment by the minute, every time you open your mouth you drop yourself in it. Now you are lying to me. Of course it’s your fault, because if the keys to the wardrobe were in your pocket, and not around your mothers, then I am sure that you would be dressed differently. By the way that you have taken to dressing in my clothes like a duck to water, and no pun intended, I get the feeling that you are a secret cross dresser,” and once again she laughed at his red face. “I think I am going to have so much fun with you from now on, and just to make sure you toe the line, I might even draw up a contract of do’s and don’ts.”

It was some hours later and they had both been watching a film on TV; Dave stood up and stretched himself after yawning. “How come it took you so long to get the fish and chips?”

“I was talking to the girl in the hardware store, I knew her from school.”

“What were you doing in there?”

“Getting some shopping and it was things I might need later, I need things to experiment.”

“Well I’m going to bed are you coming Sally?”

“Yes because we are going to play a little game, but I’m not sure that you are going to like it or not, but it doesn’t matter anyhow.”

Inside the bedroom Dave stripped off the dress and was just about to push the briefs to the floor. “Stop, that’s far enough, I would like you to leave my knickers on, and lay on the bed Dave.”

“You’re joking right?” he asked her.

“Do I look as though I am joking, just do as I say, remember you owe me big time, you have a long way to go before you are forgiven.” She stepped back and watched as he did as she instructed, and he was now in the middle of the bed. “Now put your arms out to the corner of the bed, and I dare you to move them until I say so.” Once again Dave did as instructed, he knew that to argue would be useless, and it would mean that he was in trouble for a lot longer. He watched as she walked to the edge of the bed, and she repeated what she had said about moving, and straddled his chest with her legs. Then without warning she leaned forward left and right, and slipped his wrists into cord with a slip knot attached, and removed her body from his chest. “Can you move your hands Dave?” She watched as he tried to pull them down, and the immediate look of shock.

“I can’t move, what the hell are you playing at Sally?”

“As you can see I’m not playing at anything, this is all very serious, and now I am going to lay out the rules. First though I have to check something out, I was wondering if I ought to bring Jill over here to have a look at the way you are dressed.” She looked at the shock on his face and then he started to wriggle, now stop doing that, it was a question and not a fact. But looking at the lump in my knickers, I think that you were relishing the thought of being seen in female attire. Now I am going to put some more clothes on you, but if you kick and struggle I will go and get Jill, she is in tonight and only two doors away.”

“Let me go Sally please, I will do all you ask without all this nonsense.”

“Now you know lover that I cannot do that, you have a penance to pay, and it starts right here tonight. Now lay back and relax, and I will dress you up as I see fit,” and he watched as she walked over to her wardrobe and opened the door. She picked up a few items and walked back to the bed, and looked down at Dave, “You’re going to love this, and then again maybe not,” and she gave a little giggle. She opened a bag and took out a stocking, after slipping her arm inside she rolled it down to her wrist, and holding the ring with both hands she slipped it up his leg, and did the same with the other stocking. Sally put her arm across and felt his manhood, and it was rock hard. “Wow, you really must like my clothes,” and then before he knew what was happening, she had slipped more bonds onto his ankles. Then Dave watched as Sally fitted a suspender belt, and attached the stockings, she made sure that the suspenders went under the knickers, there was plenty of time for a little fun later. “I wonder if I ought to put a bra on you,” and she laughed and added, “No, I think I will leave that until the next time.”

“Err umm, what exactly do you mean by the next time, this will be the last time you can bet on that.”

“Oh dear Dave, there you go once again spouting off at the mouth, now for that remark you will have to wear high heels all day tomorrow. In fact just to show you that I mean what I say, I will put a pair on your feet now.” Once again she walked over to the wardrobe, and walked back with the said shoes in her hand. She pushed them on his feet and said, “Same size as me, aren’t you lucky.”

“How” he asked in a squeaky voice and then cleared his throat. “How do you mean that it is lucky?”

“Well, think about it, the shoes could have been smaller and your little toes would be crushed,” and she gave another laugh. “Now for the little bit of insurance,” and she walked to the chest of drawers and came back with a digital camera. Then for the next few minutes, Sally was taking photos from all angles, at one time she was up close and she said “Smile,” and like a rabbit caught in the headlights of a car, he did just that. “Damn, damn, damn, that was not called for,” he shouted, but she just pouted her lips in a kiss and then smiled. The session was over, and she walked across to the computer.

“Of all the people that I could have been in love with, I had to go and choose the twisted female version of David Bailey.” He tried to turn his head to see what she was doing, and in desperation asked her that very question?

“I’m just putting the photos in e mails to all your friends.”

“Do you hate me Sally?”

She burst out laughing and answered, “No, I am not sending them, but they can be sent any time I check into my mail box on my mobile, and then if you are naughty, zap, and your life as you know it will be over,” and once again she laughed.

“That lightning today Sally, it never struck you on the head did it, because there is still time to go to the hospital before the damage is permanent.”

Sally burst out laughing once more, and after a moment trying to control herself she replied, “That’s right lover, keep your sense of humour.” Dave then watched as she walked across to the bed with a piece of A4 paper in her hand. “Now listen in slave, and until you show me remorse that is exactly what you are, my slave. On this piece of paper are the rules that you will abide by, or I will send the e mails, do you understand slave?”

“Err do I get the chance to appeal against your judgment?”

“Let me think!” and she tapped her finger on the side of her face, “In an answer of one syllable, no. Now, answer the question, are you going to abide by the rules?”

“Yes,” he answered reluctantly, “Do I get to see them?”

“Of course you do,” and she turned the paper so that he could read what was written down. There was only one sentence saying; you will do all I say at all times, and punishment will be painful.

“Is that all, and what is the painful punishment, and after asking you I am not sure if I really want to know. I am getting feelings of misgivings and fear, but mostly fear.”

“Well I think we could start off with some gentle caning.”

“Gentle caning you crackpot, what planet did you come from, because it will sting like hell?”

She was laughing at his outburst and then said, “You now owe me three strokes for calling me a crackpot, and you know the saying slave, you have to be cruel to be kind.”

“Well if it’s all the same to you, I don’t want your kindness.”

“There are ways that you can reduce your strokes of the cane, and that is I will give you marks out of five for your love making. So you had better start improving, because you have been slacking of late, and if your points are above three you lose to strokes, and if your marks are below three, then you gain two. Wow, I’m beginning to like this game already, and I’ll bet you wish you had not humiliated me now slave?”

“To be quite honest, I’m beginning to wish that I had not been born, anyway, where did you learn to use the cane?”

“It just so happens I have been reading a training book of punishment, and it tells you the correct way to strike the buttocks with a cane.”

“I just know I am going to regret asking this question, but what is the book called.”

“The Marquis de Sade, and it was one hell of a good book, I’m still reading it and picking up points.”

“You are joking right Sally, and you’re not really reading it?”

“Of course I’m joking you silly fool, I have already read it at school,” and she snatched the paper from him and laughed. “One other thing, from now on you can call me Mistress.” Sally walked back over to the bed and said, “Seeing as you have been a good slave and done all I asked, I will give you a treat.” She then pulled the two bows on either side of the yellow knickers, and they fell from his body. She saw his manhood standing proud, and said, “Keep that thought.” Then she slowly began to strip off all of her clothes, and once she was naked she knelt down at the edge of the bed. Her hand slipped out to grasp Dave’s manhood, and at the moment she touched it, he gasped for air and held his breath. She was playing with it and gently masturbating him; and with her other hand she played with his glands watching him shut his eyes. Sally was doing this for some time, and then he started to buck his hips, in the hope of speeding up his climax, but she had better and far more rewarding ideas, but they were for her benefit. She was still masturbating him, and when he was ready to cum, she stopped, smiled and said, “Damn my arm is tired and it needs a rest.” She heard him groan, and asked, “Is something wrong slave?”

“Nothing at all you bitch,” he murmured.

She smiled and asked, “What did you say slave only I never heard?”

“I just said that I had an itch Mistress,” but he was thinking, ‘steady Davey boy, you nearly got a few more strokes, and you don’t know what they feel like yet.’

She smiled at his answer, “Well speak up in future, I don’t want to think that you are disrespecting me again.”

“God forbid I should ever do that Mistress,” and again thinking, ‘bloody hell I’ve started to creep to save my ass.’

While he was creeping to save pain, Sally was looking at his body, and the first thing she noticed was, that he had very little body hair if any, even the ones around his groin area and armpits were soft and few. She lifted herself up from the side of the bed, and then she looked down and smiled, she was going to get her own satisfaction first. She once again straddled his body, and his erect penis was just touching her buttocks, he was trying in vain to get relief, but she was not going to allow that. Sally moved her body forward so that her sex was almost touching his chin, “Now slave, you have work to do before you get your satisfaction, and if you are not very good at the task, that I am about to set you, then your own satisfaction will not be forthcoming.” She moved closer, but not before looking down into his eyes, and then the final movement, and his mouth was clamped over her sex.

Dave was looking up at her body, and he could just see her breasts quivering like jelly, but it was only fleeting. His tongue was darting in and out of her sex, and he was now and again gently biting the soft folds that filled his mouth, but her hips were moving and pushing down. It was not a hard movement, and he could feel that she was using her legs to check her weight. There were times when she lifted up, and he lifted his head to lick the entrance to her sex. The pungent smell of sex and scent so close to his nose, was almost overpowering his breathing, but he knew now and just like the many other occasions her needs came first. There had never been a time that he had let her down, and failed in his quest to satisfy her craving for a powerful orgasm.

Sally was gently moving her body, now and again lifting it from his face and allowing him to breathe, there was no need to be cruel, and he was her lover as well as her slave. She had her hands on her breasts and playing with her nipples, tweaking and twisting pulling and making them rise tom the occasion. She was near to completion of her own sexual gratification, and she could feel the tremors running through her body, and exploding into the waiting orifice that was giving her so much pleasure. He had done well and it was only right that she should reward his efforts, but it was a foregone conclusion before the act that it would happen. Her body slipped down to his chest, and then down further so that their sexes were now touching, the fluids from the orgasm had lubricated her entrance, and she impaled herself on his manhood. She fell to his body pressing her breasts tight to his, and at the same time kissing him full on the mouth, and not for the first time tasting her own juices. It was giving her a feeling of immense pleasure just holding her lover so tight and close, but her lusts were on the boil once more, and she started her methodical movements of rising and falling.

As her sex enclosed his manhood, Dave closed his eyes and he never saw her mouth reaching out for him, but his response was instantaneous. The pleasure that this kiss was giving him was the compensation for the humiliation she was inflicting now, and he knew that there was more to come. But live for the moment he was thinking, there was nothing he would not do for the love of his woman, and now his Mistress. Her soft breasts were pressing against his, and her arms had slipped behind his back, and her strength was pulling him to her. In an instance Sally was again upright, he wanted to feel and play with her breasts, pull the nipples and torment them, but he could only pull on his bonds with frustration. Her body was lifting up and down, and he wanted her to go faster to quell the aching in his loins, but she only looked down and smiled.

Sally could see that his bonds were holding him fast, and she also knew what he wanted, and it was what she wanted also. Still keeping the rhythm, she lowered her body so that he could use his mouth on her breasts, and it was like a giant suction pipe, as he manipulated her nipples with his tongue. It was shortly after that when she pulled away and let him have his way, as she fell on his manhood, he was pushing hard to meet her, she saw his eyes turn upwards like many other occasions, and their orgasms met in the fires of ecstasy. Sally gently lay on Dave’s chest, her cheeks touching his, he had once again excelled in his love for her, and she appreciated his every effort. Without saying a word she slipped from the bed, and walked to the end, where she took the shoes off of Dave’s feet, and then after releasing his bonds she removed the stockings and belt. The last thing was to release his wrists before getting beside him and pulling the covers over them, “Good night slave.”

“Good night Mistress,” Dave replied with his eyes closed, Sally smiled and closed hers.