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Synopsis I was an occasional cross dresser. My wife caught me.
She was very much upset. Our marriage went downhill from that point.
Little did I know that she had planned my dénouement. My life took many interesting turns after that.
Categories CD TG
Keywords High Heels French Maid Bestiality Bondage
Cuckoldry
By Janet Baker
She returned unexpectedly from shopping and caught me at the computer wearing a bra with forms under my t-shirt. I was also wearing my highest heels -- I only had two pairs -- three inch and five inch heel pumps -- both shiny erotic exotic very black patent pumps. Yes! I love heels! Storage -- concealment from my conventional -- I believed -- wife limited the amount of treasures I could amass and hide. One dress, lingerie, stockings, a wig and heels were all I could hope to own. They were indeed my treasures -- my precious pretties.
I knew that my activities were unconventional but I also knew that thousands, if not millions of men also enjoyed cross dressing so while I certainly did not want anyone to know of my hobby, I was not ashamed of my desire to dress. I especially liked wearing my satin bra and my silicone forms -- it gave me such pleasure to sit at my computer or watch TV caressing my breasts -- false as they were. I was proud and delighted at the feminine figure they gave me. I felt so gloriously female. When I walked throughout the house my walk became feminine -- my ass wiggled -- I thrust my chest out proudly.
Ironic! I was somewhat smaller than average but in school I had been quite athletic and was a fine skater. My graduate school, Wharton, put me on the fast track to become a very young CFO. Naturally I wanted to keep my hobby a secret so no one knew of my pretty stash kept in a locked tool box.
A scream -- a screech -- and my soul was laid bare.
“Oh my God Jay! What the hell is this?”
“Janet, honey, I can explain -- it’s nothing -- really -- just a little hobby of mine -- nothing for you to worry about.”
“Well?!”
“Janet Hon. It’s simple, really. I like putting on these things that you see. It gives me some modest amount of pleasure. I’m not sure I could explain the underlying psychology but quite simply, I like to dress -- cross dress.”
“You’re a pervert -- a queer! My God! What the hell did I marry?”
“Janet. No! I am not a pervert! I am not gay! I simply like to cross-dress.
If you’ll take the time to look into the subject you’ll find that it is common and quite benign.”
“Oh Christ Jay! What the hell am I to do? I married a man -- not a secret girl. Are you half girl -- half woman? Do you want to become a woman?”
“No sweetie, I don’t want to be a woman. I’m the man I always was. I love you. We have been successful lovers ever since we married.”
“Who says?” She sneered.
“I thought we had a good marriage -- a good sex life. I’m happy, aren‘t you?”
“Not… really… Jay… Not completely.”
“Ahh, what do you mean Janet? What would you like me to do? Is there something special you want from me?”
“We’ll discuss that subject later. But now we’re talking about this dressing perversion. I want you to stop it and stop it now!”
“Janet! Please! This… hobby… of mine is and should be insignificant to our love and our marriage. It’s a… nothing… nothing at all!”
“I don’t want to see you like that! Please go get dressed properly. We have things to do today and I can’t take you to the mall with your chest bulged out like that. Hah! And those heels are too high for mall crawling. My God! I can‘t even wear heels that high. Yeah Jay, now I understand why you wanted me to buy and wear sexy heels! You‘ve got a shoe fetish! You‘re really perverted!”
“Holy shit Janet! What’s wrong with you wearing pretty shoes? I am not perverted -- at least I don’t define it as perverted. Hum, maybe a tad off the norm but the odd thing is -- I like my little hobby. I like dressing. I tried to keep it from you. You’re finding me like this was an accident.”
“A good accident for me Jay. I understand you better now, I think. I’ve wondered why our sex life was less than pleasing to me. Maybe this thing -- this stupid hobby -- of yours explains some things of which I’ve been concerned. “
“What Janet? What do you mean?”
“Jay, to begin with, I don’t always have orgasms. My girlfriends and I talk about sex and they claim they always have earth shaking orgasms. I don’t! I hardly ever have an orgasm.”
“I’m sorry Janet. I didn’t realize… You discuss our sex life? -– the most intimate secrets of our life…?”
“No! Of course not! Furthermore you goddamn men only think of yourselves, never of us.”
“C’mon, Jan, I always think of you. I try to satisfy you. I stay hard until you’ve finished, then I orgasm.”
“Yes, I may have finished. Not from pleasure but from fatigue. I get on top and pound away at you until I’m dog tired but I still can’t orgasm. Only occasionally do I have good soul filling orgasms. Maybe you‘re thinking of someone -- something -- else while making love with me. Do you ever have a fantasy? Thoughts about someone else?”
“No Jan, I think of you and I’m sorry Jan. I try to make you happy. I try to please you. If you know what you want of me, tell me! I’ll do anything I can to please you. Janet, why do you bring up fantasies?” She ignored my question but then…
“Jay, I’m trying to believe you…. I want to believe you… but… but it’s impossible for me to believe that while you’re pounding away on me, your mind is a blank. Truth now. What do you think of?”
“Well… I think of you… now and then I think of you dressed in something sexy.”
“Should I wear whatever you have in mind?”
“Ehhh, not really.”
“Why not?”
“Ahhh, some things I think of are rather outré… exotic. Things I wouldn’t really expect of you.”
“For example? And why not?”
“Ahhh, c’mon sweetie, I’d rather not… some are… maybe… rather silly… just fantasies, that’s all… nothing serious.”
“Who! Who? Who is in your… fantasies?”
“You sweetie, only you. You’re my one and only Janet. Really! My one and only.”
“Uh huh! Tell me! Tell me dammit.”
“I told you. You’re the only one I think about.”
“I don’t mean that dammit! I want to know what you think about -- your fantasies -- the dreams -- fantasies you have while we’re having sex!”
“Well… there are a few. They sort of run in spurts. A fantasy might help my… a… sexual… strength for a while, then fade and I might think of something else.”
“How does that work? What happens? Sexual strength? What the hell?”
“Uhhh, if I feel my erection fading, I might think of something really erotic to help me keep my erection up for you. That’s all. Just a little mind game to improve my performance.”
“Ooo Kkkk! Now! Does your dressing ever play a part in your fantasies?”
“Ummm, nooo.”
“I don’t believe you! It just doesn’t make sense. Dressing is too important to you. Tell me dammit!”
“Mostly I just think about a new pair of heels, really high heels. Dressing is not as significant for me but you wearing heels is important.”
“Hmm.… has something to do with you wanting me to wear heels. OK!
So it’s mostly heels. But that’s for your pleasure. What do your fantasies have me doing?”
“Well! I love you Janet and my dreams -- fantasies -- are about you and you being different women. For example I might imagine you as a maid, a French maid, dressed in all the stereotypical accoutrements -- cute black satin costume, net stockings, gloves, cap, apron and most importantly high black patent heels with ankle straps. I would have you serving me a cocktail then making love with me. Hot, passionate love with me.”
“Oh God, you’re a nut! What else?”
“I’ll tell you more but what about you? Do you lie there -- under me or over me -- with a blank mind, or do you also have thoughts -- dreams -- fantasies?”
“You won’t like what I could tell you. It’s best if I don’t.”
“You’re kidding! What is so terrible that you can’t tell me?”
“If I tell you, you may be seriously hurt -- embarrassed. I’m angry about this dressing thing but I really don’t want to hurt you -- badly.”
“Please! I can’t imagine how you could hurt me by sharing a fantasy.”
“OK! But don’t say I didn’t warn you. My girl friends talk about how big are their husbands’ penises. True or not I don’t know but they say the penises are almost twice as big as yours. They talk about how quickly they reach orgasms because the penises are so long and so thick. I know their husbands and whenever I look at them, I fantasize about having one of those big penises in me. I dream about thrusting myself up and down, up and down on an enormous penis. They call them cocks. I guess I should. The problem, darling, is that your little cock does not bring me to orgasm without a great effort. Sooo… I end up thinking about my friends’ husbands and how it would be like to make love with them. I actually fantasize about having the two of them in me at the same time! How about that!?”
I was speechless. Utterly speechless! I mulled this bombshell for a few moments, collected my thoughts and said, “Darling! You never did it did you? By… the… way… darling… how do they know of my penis size?”
“Of course not! What do you think I am? And I may have said something about size… maybe… I’m not sure.”
“Yeah right… You’re my darling wife! Now you understand fantasies. They please you but you don’t act on them unless…”
“Unless what?”
“Well… unless they are well within the realm of practicability. For example, if I fantasize about you’re wearing special, erotic heels; you could easily fulfill that little, limited fantasy. You could dress as a French maid.”
“That doesn’t seem to be much of a fantasy. Dressing like that would just be silly.”
“Silly, maybe, maybe not – to each his own. But having a ménage a trois with your friends’ husbands is a fantasy beyond reality. That would be a marriage breaking occurrence. It could be a great fantasy but…”
“But nothing! If you can fantasize, so can I. Hmm, suppose I dress as a French maid. Would you like that? Do you think it would enhance our sex life?”
“I think that it would be delightful. You’d make a charming and sexy maid. I’ll order a costume for you, OK?”
“Hmmm, maybe… but don’t you think you should do something for me?”
Considering that I was in the dog house I willingly said yes.
“What do you have in mind Jan? I don’t want to give up my little ‘hobby’ if that’s your scheme.”
“Hmmm, actually Jay, I’m beginning to see… beginning to think about something else. You look kinda cute with your boobies sticking out. I’d like to see you completely dressed. You get dressed. I’ll start dinner.”
I was nonplussed, a little confused and a little more than worried with this change of direction. What did she have in mind? Or am I just being paranoid?
I went to our bedroom and dressed in my only outfit, my jersey LBD – I love the way it hugs my curves – my lingerie, my five inch heels, wig and a little jewelry. I admired myself in the mirror – satisfied. Feeling quite femme I presented myself to my wife, twirled for her approval. She smiled – enigmatilly.
“You’re fairly convincing Jay. I think that with a little professional hands-on improvement, you’ll look good enough to pass. Have you ever thought of passing?”
“Only in passing – no pun Hon. My pleasure, currently, comes only from dressing by myself. I can imagine, speculate about passing but in the past, no, I have not really thought myself passable.”
“Jay, I look at you dressed in that cute little black dress and I swear you look good! Really good! I’m convinced that with some professional attention you’ll pass and pass anywhere. Nice, huh?”
“I dunno, Hon, it’ll take some thought. I’ve never thought that far ahead. I’ve been content with my homebound activity -– never had a need for an outing. It could be interesting - – could be fun. Maybe. But why? You’ve come a long way in a short time from a screech to more than acceptance. You’re actually encouraging me to dress and even get professional help. I presume you mean a trip to a salon.”
“Jay, our discussion of fantasies has opened my eyes to new horizons. I can see from your perspective the pleasure you derive from dressing and if dressing will improve our sex life… well… I say ‘let’s try it’. I’ll buy and wear anything you like but ahh, you’ll do the same, right? I do believe that your wardrobe needs major improvement. In fact, I want all your measurements so I can buy for you, assuring good fitting.”
“Uhh Jan, what are you buying for me? I may have some preferences.”
“You may offer suggestions but I’ll approve or disapprove. My taste is probably more developed than yours. I like your LBD but the world wants more than one little black dress. You’ll need many outfits with coordinated accessories, bags, jewelry, and most important, the correct shoes. Your shoe collection must include colors matching your dresses. You must have pumps, sandals, high heels, flats, and those in between. Shoes are most important for a girl.”
Intrigued, puzzled, somewhat relieved and more than a bit anxious I smiled and said, “Janet darling, I’m so happy, so relieved that you are… interested in my situation – my little hobby. What sort of clothing do you have in mind? Just ordinary dresses and separates? Lingerie? I’ve thought about buying a bullet bra so my figure will resemble a girl of the forties and fifties. What would you think of that, Jan?”
“I think it’s a good idea and… when I get a maid’s costume I’ll order one for you too. We can be twin maids! How erotic! How sexy!
Hey! I’ll wear a bullet bra too! Won’t that be cute?!”
“Hell yes! Especially with your ‘D’ cups! Good lord will that be hot!”
“Then it’s settled. I’ll buy you some clothes and you will go to a salon for some modest improvement.”
“Wait a minute! Is this salon stuff gonna be permanent? I never wanted to do makeup, just dress.”
“You’re gonna do it for me Jay, I want you to. It’s a fantasy we can make real.”
“Who’s fantasy Janet? I never wanted to make up – to pass. Is this one of your fantasies? If it is, you didn’t mention it during our discussion today. Have you thought of making me up in the past? And why? Have I ever given you the merest hint of my hobby?”
“Heavens no! Today is the first time I’ve been aware of your interest in dressing. After the first shock I’ve begun to learn a little and perhaps even understand your feelings. I also see some potential for sexual amusement. There’s another fantasy I never told you about. Can you guess?”
“I… don’t… think… I could ever imagine what it might be. If I would imagine something, it would be a fantasy anyway… so, tell me.”
“Well Jay, have you ever thought about tying me up or putting handcuffs on me and then taking your pleasure with me?”
“Nooo… Oh my! Your water runs deep. I could do that… if you wish.
You do surprise me darling. How many layers will I peel back until I find the real you?”
“I really don’t know Jay. I always thought I was uncomplicated but as I reflect on my past and our chat I begin to wonder. I’ve had some most interesting fantasies – dreams.”
“Were your dreams different from your fantasies? Did a fantasy follow a dream? Or what?”
“I seem to recall that most dreams were cock centered. Some of my fantasies were also cock centered but the fantasies ranged farther afield.”
“Describe a dream, if you can recall.”
“Oh my! Let me think a moment. Hmm. OK. Generally a cock centered dream focused on my impaling myself on a cock. I don’t know whose cock – I don’t know. The owners were faceless, amorphous but I felt the cock and achieved an orgasm. Basically I believe that my body was experiencing arousal before the orgasm and the dream was created as a result of the feelings the body was experiencing. It all seemed so real and the orgasms were certainly real – I dripped….”
“OK, so you had dreams leading to or resulting from sexual arousal and subsequent orgasms. Did these experiences lead you to creating your own fantasies?”
“Well… I guess so… I’m not sure when I started fantasizing but my fantasies generally involve cock.”
“Janet, cocks are attached to men. What men did you use in your fantasies? Who were they Janet? Who were you thinking about when we were making love…? Janet?”
“I told you earlier Jay that they were my girl friends’ husbands. The girls bragged about the size… and the pleasure…”
“Janet! Bragging about size does not make it so. My penis is of normal size – normal length and thickness. I discussed this with my doctor years ago. I think your problem stems from your friends teasing you. I do not want you experimenting to determine whether or not I’m telling you the truth. Take for granted that we are physically compatible and that any improvements must be home grown. I’ll do anything reasonable to enhance our sex life and I hope you’ll do the same. Do you really want me to tie you? How would you like me to do that?”
“Wellll, once I had this dream – daydream – of you coming home and tying me to the bed, spread out, legs apart. Then you slowly undressed and mounted me. I was extremely excited and thrust myself upward to meet you -- and then I had the most awesome orgasm. I was at work at my desk and embarrassed myself by crying out and wetting my panties. I had to rush to the ‘ladies’ to clean myself but the image of being restrained and helpless remained with me. Oh! I loved it!”
“Darling that sounds soooo exciting! I would love to do that for you. Were there any other tying games you thought of -- dreamt of?”
“Yes, I’ll tell you more later, but now let’s get properly dressed and do some shopping. You need lots of things and I want to make an appointment at Jenna’s Salon. I want you to learn how to do makeup.”
“We’re moving awfully fast Jan, don’t you think? It was only hours ago that you caught me wearing my bra and heels. I don’t quite understand -- I really don’t.”
“Jay! Don’t complain! You enjoy ‘dressing’ so I’m helping you. I don’t see a problem. What’s wrong with my helping you?”
“Nothing Janet except that it seems well out of character. I appreciate your interest, your apparent forgiveness but it seems too good to be true.”
“Don’t knock it, fella, count your blessings. I’m helping, understanding, not divorcing, not screaming – be happy guy! Now! Let’s go shopping! You need everything -- everything -- from stockings to wigs and all in between. Things we can’t find locally, we’ll order on line. I’m so anxious to get us a pair of maid’s costumes. We’ll look so cute together. And Jay, remember we were talking about tying -- restraint -- games? Wellll, I’ll search the net to see what I can buy there. I think that we’ll have lots of fun together!”
“I’m game, let’s go. I’m thrilled! I’d love to have some new things. I’ve always held back, trying to conceal my hobby from you. I’m so happy that you’re accepting this aspect of my persona.”
“Jay, this is just the beginning. We’ll have a ball together. I’ve already thought about some things we can do and as soon as we buy you some more clothes you’ll be ready to dress and dress and dress.”
“Janet, I can’t begin to tell you how much this means to me. I’m so happy!”
A chill! Something is wrong here. She can’t have changed so much so quickly… but… should I confront her? What good would that do? If she were plotting something, she’d simply lie. Maybe there’s nothing to my concern. I’ll go along… at least I’ll get a wardrobe.
“C’mon Jay! We have much to do -- stores to visit. Let’s start with Victoria’s Secret; they have the most beautiful lingerie. They won’t have bullet bras but we’ll buy them online. Now! I want you to have satin pajamas, satin bras, camisoles and lots of pretty panties. You’re going to be in seventh heaven wearing these pretty things. After VS we’ll buy some dresses, tops, skirts and then Bakers for some cute pumps. Oh yes, let’s not forget jewelry.”
I was losing my mind with the pleasure of all the pretties, so much that when she suggested piercing my ears I didn’t object and came away with studs and some chandeliers. At the shoe store I started to get a hard on. I was so bedazzled I didn’t care that the sales staff looked at me askance. Loaded with packages we then went to Janet’s salon where she made an appointment for me to have a makeover.
“Oh Janet honey, I’m so freaking thrilled! All the shoes! Heels, flats, even boots. Jan, if I’m going to dress shouldn’t I have powder, perfume? I should smell pretty as well as look pretty, shouldn’t I? What wigs do you think would look well on me? I really want to look perfect.”
“Yes Jay, definitely. We’ll perfume you, powder you and when we’re done you’ll have to fight off the men! You are going to look great!”
“Uhhh Jan, I’m not so sure I want to have contact with men. This is my personal game.”
“I understand Jay, no problem. Jay. From now on, for a while at least, I want you to dress when you come home from work. I want you to practice womanly characteristics – movements – walking, sitting, fluffing your hair, checking yourself before leaving the house, making sure your purse has all the things a woman might need. When I feel that you present yourself adequately we’ll go out together as two girlfriends, perhaps out to lunch, perhaps to dinner or a bar. It should be a blast. I’m looking forward to it.”
“Sounds great Jan! Let’s go home. I want to try on my dresses and heels.”
Day after day I pleased and pleasured myself dressing and applying makeup on arrival from work. Janet’s work day extended beyond mine so I had ample time to practice my womanly skills. Each week I went to Janet’s favorite salon where I was welcomed by the staff, all used to pampering me, doing my nails and toes. These Thursday visits took time but I was still able to get home before Janet and start dinner. In fact, Thursday dinner was frequently delayed until nine o’clock or later. Janet would call when she was ready to leave work.
A few weeks later the maid’s costumes arrived. Special pumps with six inch heels were also delivered. We both found them a bit too high but they were so erotic we persevered and eventually we were able to walk proficiently albeit with quite short steps.
“Jan, these heels are awesome. I think they’d look even better with shoe locks, don’t you?”
“Jay, where did you learn about shoe locks?”
“From the internet. I also found a source for ballet boots and some bondage toys so we could play restraint games. Remember that some time ago you described the pleasure of being restrained.”
“Yes Jay but first I want us to dress in our new maid’s costumes and play at being maids. I want to take a picture of the two of us together –- for our pleasure. You look just perfect Jay, you’re really becoming womanly. In a few weeks Jay, I’d like us to go out and dine together.”
“Janet, don’t you think my voice will betray me?”
“Not really Jay, I think your voice is alright but we can improve it a little. I know how. A doctor I know can adjust your vocal cords just a little so your voice will rise somewhat. It would be in keeping with your womanly persona and still be ok for your manliness. It’ll be ideal. You’ll have a slightly higher man’s voice and a slightly lower woman’s tone. You’ll fool everyone. Just think Jay! A husky Jane Russell sound! So sexy! We’ll talk with the doctor as soon as possible. He might also be able to shrink or shave your Adam’s apple but your cheekbones are perfect. We just might think about growing your hair longer.”
“I don’t think so Jan, I’d have work problems. I’d like to stick to wigs if it’s OK with you.”
“Well Jay, we’ll see. Perhaps sometime later we’ll discuss it again. At least one’s hair is not apt to fall off and you do have a lovely head of hair. Now, Jay let’s put on our maid’s dresses and see how cute we are.”
“Janet, these heels are awfully high, I can hardly walk in them, how are you doing?”
“Quite well Jay, but then I’m more practiced than you. Jay… from now on you should wear them at home and that way you’ll get used to them. I so like to watch you walk – it’s so erotic for me. You’re so cute! We have to give you a femme name. I know! Jane! It’s obvious! Just think -- Jane and Janet off to dinner -- dinner and dancing.”
“I’m not quite ready for that Jan. I think I need more practice in the womanly arts. I love the idea though.”
“OK Jay -- Jane -- enjoy your practice, your dressing. Let’s target three weeks from now for our first outing as girls. We’ll see a movie. You’ll feel more secure in the dark. Then we’ll go eat.”
“Mmmm, fun! Janet, I’d like to wear slacks, mid heels and knit top, OK?”
“Yesss, velvet slacks with knit sparkle top sound great. We’ll find some within the next few weeks. Not only that Jane slacks and heels are commonly worn. They look sexy.”
A few weeks later with considerable effort I was walking gracefully with a feminine stride, holding my elbows close, keeping my chest up and out and my makeup skills had improved markedly. I was ready to sally forth as a confident woman. Sex life remained status quo ante -- neither good nor bad. With Janet’s erratic hours I had lots of time to dress and practice being femme. I loved it. I really did not suspect any
untoward behavior from my wife.
“Jay, it’s time for us to go out. Guess where we’re going.”
“No idea. Where?”
“We’re going to a bar where different lifestyles are tolerated. We’ll encounter folks who are gays, lesbians, cross dressers and anything in between. I went there with my girl friends and it’s very colorful. You’ll like it.”
“What’ll I wear Jan?”
“Just like a woman! ‘What’ll I wear’? Jane, in order to look like a pair of lesbians we’ll wear the same thing – slacks, knit tops, bullet bras and four inch heels, gold necklaces, gold chandeliers and Chanel number five. We’ll dance together and look hot. Then we’ll come home and fuck like mink. We’ll have a ball.”
“Why lesbians, Jan?”
“That’ll help keep the men off us. This’ll be fun Jane, it’s another of my fantasies -- well, maybe fantasy is too strong. I’ll just call it a cute idea.”
“I’m beginning to think that your fantasies are never ending -- anymore?”
“Yes. In fact I’m going to Hollywood to do a screen test.”
“You’re kidding!”
“Hell no! Why not! I’m pretty and I’ve acted in amateur works in college. The last director I worked with told me that I had potential and set me up for a test.”
“When?”
“Not sure, probably within weeks. I’ll let you know.”
“Sounds great Jan, I’ll see if I can get time off from work.”
“Welll Jane, if you come along with me will it be as Jane or Jay?”
“As Jay, certainly. What do you think I am?”
“I know what you are Janey darling -– my own little transvestite. Oh Janey, my baby is so cute in her maid’s dress. We have such cute pictures of us don’t we?”
“Uh hum.”
A few days later I arrived home finding a note from my wife telling me she had flown to Hollywood on regrettably short notice and expected to return in a few days. I consoled myself by buying some new shoes and a new dress. She didn’t leave a phone number and left her cell phone behind -- typical woman.
Days passed and I became somewhat nervous. I was especially concerned since I had no way to contact my wife. I even thought about informing the police. I fed myself and had a great time dressing. Being alone was starting to wear on me so I dressed one evening and went to the gay bar that Janet and I visited. I was greeted by a few of the girls we met previously. Linda asked about Janet. I told her that Janet had gone to Hollywood, presumably to take a screen test. I replied that I was worried since I couldn’t contact her.
“I spoke with her a few nights ago; she was fine, having a good time and expected to return home shortly.”
“That’s great Linda! Why the hell didn’t she call me -- her husband?”
“Dunno, Jane but she sounded great. She was really thrilled. She did say that she was anxious to return home.”
“Linda, something is definitely wrong here. I’m her husband and she hasn’t called me. You don’t have her number, do you?”
“No Jane, I don’t but I wouldn’t worry. She sounded great.”
“Hmph! She and I are going to have words when she comes home. There’s no excuse for this crap.”
I was worried, scared, confused. All sorts of scenarios ran through my mind. A few days later she called.
“Hi Hon, I’m finished working and I’ll be home in a few days. It’s been a blast and I can’t wait to see you and tell you all about it!”
“Dammit Janet I’ve been worried sick about you. You didn’t leave a phone number and you left your cell phone home so I had no idea where you were.”
“I’m so sorry but I received instructions at the last minute and had to run. I’ll call when I have my flight schedule. ‘Bye Hon’” She hung up before I could ask another question.
I was on tenterhooks for the few days before her arrival. I met her at the airport. I was waiting at baggage claim when I saw her arrive wearing tight pants, a revealing top and the highest heels I could imagine.
“Janet! I’m so glad to see you… but… that outfit… I bit shocking I think.”
“You’re shocked? Just wait darling, you ain’t seen nothin’ yet. Wait’ll we get home. I have a lot to tell you, a lot to show you, we’ll have some friends over, we’ll have a party! It’ll be a real blast!”
I was puzzled. She was hiding something from me, I could tell. Something was dreadfully wrong in spite of her cheery greeting.
At home she prepared for a small party. She showered and dressed -- provocatively and asked me to dress as a maid.
“You’re having company. I don’t want to put on a dress. Are you daft?”
“Well then Jay – oops – Jane you don’t have to. Ha!”
That evening with a few friends gathered in the living room Janet served drinks and snacks and loaded a disk into the disk player.
“Friends, hubby, tonight we will have the unveiling of many secrets. The first thing you all must know is that my husband is a transvestite. Secondly, I had a great time in Hollywood and finally, I am now in business. The nature of the business will be revealed shortly.”
“Janet! Why! What are you doing! That’s very private! Janet! Please!”
“Worm! That’s just the beginning! Sit tight! Say nothing until I’m done!”
“Janet please!”
“Please nothing! You go put on your maid’s dress -- complete with accessories -- or there will be retribution. Then come back here and show our friends how cute you are. Oh! Bring a tray of drinks too. Show how well you perform as my little maid.”
“Perhaps we should leave” said Roger, one of our friends of long standing.
“Don’t leave Rog. You’ll love the evening, there is so much more to come.”
“Ever since I discovered my inadequate spouse” she snarled, “dressed as a woman I decided to leave him and strike out on my own. I started aiding his dressing and have some delightful photos as evidence. After our discussions about fantasies I started writing screen plays for pornographic movies. I submitted samples to people in the porn business and indicated that I would be interested in participating as an actress and principal. Not long ago I made arrangements to visit Hollywood and commence my career in adult movies.”
“Oh for God’s sake Janet, are you nuts? That’s terrible!”
“Jane -- Jay is hardly relevant anymore -- adult movies are more accepted and almost respectable now, even more so than being a transvestite, twerp!”
“Crap!”
“Whether you like it or not, I’m doing it! I have a website. My work is under copy write and I’ve already earned a great deal in just the few weeks I was in Hollywood. When we’re done here, Jay or Jane, we’ll divorce. Playing at being a woman was bad enough Jane but concealing it was worse.
We’re through. Now folks I’ll play a DVD and show you what I can do as an actress. Remember, these pieces, segments are all mine, my screen plays, my imagination, the fantasies I wanted to make real. Some of them are a bit… shall we say… adult -- very adult. Some are likely beyond your comprehension.”
Linda jumped to her feet and shouted, “Wow, let’s see! Start the disk.”
“Janet! Please don’t do it. It may cause a divorce though cross dressing was never grounds for divorce.”
“Sorry Jane but the divorce is already a foregone conclusion. Now sit and be entertained.”
“You mean sit and be humiliated, appalled, disgraced, and disgusted?”
“Yes Jane, all of the above! Jane now is the time to enlighten you to the real facts of life. I knew about your cross dressing some time ago and laid my plans, exposing you when I was ready to proceed into my new life. Enjoy the movies Jane!”
She ran the disk. I hated to admit it but she was an outstanding porn performer. Her first segment was tame. She met a fellow at a bar they danced intimately kissed and left. They were next seen in a hotel room.
She undressed him, dropped to her knees and sucked him to an erection, jumped up onto the bed, placing herself on all fours. He lubed himself and thrust his formidable cock into her rectum while holding her by the waist. She, a good actress responded in good voice, yowling, howling and begging for more. I was shamed and humiliated yet impressed by her professionalism.
In the next segment she arranged with two men to fuck her. They adjourned to the hotel where she explained what she wanted done. “You! Luther! I’m going to lie down prone. You push your cock into my ass. When you’re all the way in, hold me and we’ll roll over and Allen can enter me from the top. I want you two to alternate thrusts. I want to feel that in-out, in-out movement.”
They commenced the fuck as she outlined and she again emoted with genuine passion. In spite of myself I enjoyed the spectacle. She continued to play the disk, showing many different faces of Janet. I could not believe the imagination represented by her porn segments. She insisted she wrote all the screen plays. For me, I was glad to be faced with a divorce. I wanted nothing to do with someone in the adult entertainment business, including my wife.
Over the weeks since she caught me dressed, I became increasingly convinced that I might like to be a woman… not to perform as she did but simply to be one of that preferred sex. I was more and more content with my part time role as a woman. This divorce could be just the opportunity to further my explorations into femininity.
The following segment showed her tying herself to be immobilized while waiting for a husband or lover to release and take her. She tied rope around her ankles, then legs above her knees. She tied a pair of handcuffs onto a length of rope and tied the rope around her waist with the cuffs behind her.
Just before he arrived she put a gag in her mouth and a blindfold covering her eyes. She finished by carefully putting her wrists in the cuffs behind her. She was totally and irrevocably restrained by herself, unable to do anything until he -- or she -- arrived to release her. The release was unexpected! Her apartment was invaded by three men seemingly intent on burglary. They discussed her predicament and ungagged her, leaving the blindfold in place. She cried out, “Who are you? Where’s Sam?”
“Janet we gave Sam 100 hundred dollars to take his place. We’re going to have fun, fun, fun with you… whether you like it or not. Open your mouth girl we’re going to fill it for you, one of us at a time.”
So saying, the three men took turns ravaging Janet’s mouth. She sputtered, plead, cried and begged, all to no avail as the men pleased themselves with her.
They finally left leaving Janet still self tied, crying. I could not help myself. I said, “Janet, dammit, I hate it but that was a good piece of work.”
“Hmph, thank you twerp, but we are still divorcing. You know, Jane if you make a pretty enough shemale maybe I’ll hire you. Ha!”
Janet starred in numerous segments, some of which were too intense to be recounted here but may be found elsewhere. Her work ran the gamut of adult fantasies. She performed in femdom skits where she humiliated her spouse. Bondage was explored intimately not excluding severe restraint and even whipping. Her skit spouse was tied prone on a table. Flogging began and continued until he screamed for release. I never realized Janet was so strong. She really beat the hell out of the poor guy. She pulled his legs apart and snapped her finger on his testicles causing more pain and pleading.
She performed in a submissive skit where her husband, finding fault with her dinner, tied her wrists together and suspended her from the ceiling commencing a slow rhythmic whipping, starting from her ankles and stopping at shoulder height. She screamed continually as he whaled away at her, stopping finally from exhaustion.
In the following segment she changed places and severely thrashed her submissive girl friend whilst the girl was chained to a pole with her wrists high above her in handcuffs. She and another friend named Laura went to a bar and she made Laura kneel before her with her head up Janet’s skirt simulating cunnilingus, simply to humiliate Laura.
Further forced rape scenes followed. She had her men tie her wrists pulling her up off her feet and pulling her legs apart while two men fucked her brutally anally and vaginally. Then following the script, the men tied narrow cords around her breasts, forcing them to bulge out and turn color. One man then flogged her breasts while she screamed for them to stop. They finally did release her but left behind a really realistic segment of bondage rape.
Janet loved dogs. Even then I was dismayed by the segment where she had relations with specially trained dogs, ponies and even a donkey. I asked her why she would do something so… beyond the pale.
She answered saying, “people love this stuff. Fucking the dogs and ponies and incidentally playing as a pony girl is fun and is very popular with viewers of adult films. Pony boys are quite popular with dommes.
The pony boys are submissives and enjoy humiliation. I demand that they
don their harnesses, bend over for a tail to be inserted in the anus and place themselves between the cart rails for me to chain them in place. They are then made to prance as they pull the pony cart. If they flag I tickle them with a whip. Tickle hell! I really lay into them. While I’m riding the cart the other submissives are made to watch.”
“Holy shit Janet they must be a little nuts. Do they really get off on that stuff?”
“God Roger, you have no idea of the extent to which a male submissive will debase himself for his mistress. I advertised for a male sub and received several replies. Currently there are two subs living in my home in Hollywood. They dress as French maids -- constantly. One wears ballet boots while I’m present; the other wears six inch heels at least 12 hours a day. When they dress in the morning they present themselves to me, don their chastity belts and hand me the keys. Then they dress. Their heads are shaved. They wear steel collars and must answer the door as such.
They cook and clean. If I have guests they serve and indeed may service the guests. They are rewarded by being chained to a cross and flogged. At night with the chastity belts off they are allowed to masturbate or fuck each other. They take turns polishing my nails. They care for my clothing, carry my groceries and if they misbehave I hang weights from their testicles and their pierced nipples until they beg for forgiveness. It’s amazing. They are truly pathetic but unbelievably content as my submissives. I do have to treat them equally. If I cruel to one the other expects the same treatment. It gets tiring at times so I make them abuse each other. Tricky though, making a submissive abuse another sub.”
Her dog segment was quite lengthy and detailed. She had three stud dogs, big ones with big cocks that were well trained to fuck women. She had the producer supply custom made benches for the purpose. There were two; one for prone, rear entry both anal and vaginal and one bench/chair made to permit supine positioning with face to face activity. The chosen dog was led up onto a low table where Janet washed his genitals with a warm washcloth. If this didn’t excite him enough she would lick and suck his prick. When fully erect the dog would be led to the preferred bench. Janet took the first dog in her ass, holding him place whilst he drained and his knot shrank. The next dog entered her vaginally whilst she relaxed on the supine bench. She clearly loved this game, smiling, cooing at the dogs.
“My God Janet, I can’t believe you’ve fallen so low. Dogs! My God!”
“Oh you, my virginal twerp, you’re sooo innocent. Wait! Watch the next skit where I become a pony girl. My take on the pony game includes fucking a real pony after showing the pony how to prance whilst pulling the pony cart. I have the most erotic harness for this show.”
Janet stood naked while her attendants dressed her in the pony harness. They liked fitting the harness around her breasts, caressing and fondling them with delight. Head harness and bit followed the waist belt constructed to accept links to the cart rails. They cuffed her wrists to the rails then put on her pony shoes. The final touch was a butt plug with horse tail. With one fellow holding her ass cheeks apart, the other shoved the plug into her ass. Her mistress stepped onto the cart seat flicked her whip, a real whip, and Janet started to prance around the exercise ring, her harness bells ringing merrily and her tail wagging with each step. Since Janet was taking the submissive role her next task was fucking the pony -- a real pony that was also used to pull the cart with half naked mistresses wielding the whip. As with the dogs, a special bench was constructed. Janet lay down, the pony was led over her and she wriggled onto his prick wrapping her legs around him. The event was accompanied by much screaming as she orgasm’d over the thrill of the enormous cock thrusting tirelessly as she held on with legs and arms wrapped tightly around him.
“How about that folks!?” “Hot, not?”
Jay responded, “Disgraceful Janet, absolutely disgusting!”
“Jay, you pathetic shit! My darling cuckold! You didn’t like that? Well, try this story.”
Rodney is trying to persuade his innocent girl friend to attend an adult show with him.
“Oh Rodney, an adult show? I’m not sure I should.”
“You’ll love it Lisa, I attended one once, they’re quite innocent and lots of fun.”
“We’ll, OK Rodney, if you think it’s alright.”
“Sure it is Lisa you’ll love it I’m sure. We’ll go tomorrow. Lisa, I have errands to run, I’ll pick you up tomorrow at three.”
“OK Rod, tomorrow at three. ‘Bye now.”
Rodney drives to the adult show venue and converses with the management. We are not able to hear the conversation although we see money change hands.
The next day, Rodney picks up his girl friend and they drive to the show.
We now hear Lisa’s recounting of the events that followed their arrival.
“Rod parked the car and we bought tickets and entered the building. Suddenly we were intercepted by a group of really big guys. One of them grabbed Rod and the others grabbed me. I struggled but was overpowered.
Someone forced my mouth open and gagged me, fastening a strap around my neck. Another guy strapped a blindfold on me then handcuffed me and held my hands above me while they stripped my clothes off. They carried me through a door into another room. I sensed that I was in a large open area and I could hear murmuring from many people. I sniffed and detected animal odors. I couldn’t struggle since I was pulled from all sides by unseen people. They maneuvered me under an animal -- I knew because I felt hair above me and could smell animal odor. Suddenly I felt something at the opening of my vagina. They pulled my legs and this thing pushed into me -- into my virgin vagina. I tried to scream but the gag prevented anything more that grunts and squeals. They continued to pull me onto the thing that I later learned was a donkey’s prick. It hurt terribly since it was so long and I was a virgin. They pulled me up close to the animal and used wide belts to fasten me tightly to its belly. They put leather cuffs on my wrists linking them around the animal. Similarly they did the same with my ankles. I was so tightly strapped to the animal I could hardly move. The animal could only move slightly, thrusting his thing in and out but only a little since we were strapped tightly together. Suddenly the animal started to walk and then trot. I could hear people gasping, tittering and laughing. Evidently the animal trotted around in a circle. This went on for some time. Finally it stopped and I could feel his thing move and then spurt something into my vagina. People clapped and cheered. The animal walked somewhere and stopped and waited. I was so humiliated, naked, tied to an animal, raped in front of an audience, unable to speak or see. Finally they unstrapped me from the animal, took my blindfold off and stood me before the audience. I was so embarrassed, so humiliated, standing there dripping from my vagina. I could see the animal to which I was strapped – a donkey!!”
Lisa could see that Rodney was chained to a chair and gagged. She ran to him, hugged him and cried. The managers threw a gown over her and released Rodney. The two ran out of the building, got into his car and drove off at high speed. Lisa thought that Rodney was also a victim and never learned that she had been set up and that Rodney had received $1000 for delivering his girl friend to the show.
“These skits were all short. I do have a lengthy story in which I fuck gloriously fulfilling a long held dream. It’s the story of how I destroyed my husband and set myself up for continuous fucking.”
“At the risk of learning more than I want to learn, how did you do that?” asked Laura’s husband.
“Wellll! OK! I told my husband that we won a trip to a resort but that it was for singles only and if he wanted to come with me, he would have to disguise himself as a woman. He complained saying that he would never look good enough to pass. I embarked on a program to feminize him. He cooperated reluctantly but eventually he looked good enough to pass and we flew to the resort.
The ‘get together’ dinner was followed by the activities director introducing herself and asking everyone to leave his or her table and go to a table occupied by a person of the opposite sex. I had been making eye contact with a very handsome fellow sitting with another equally handsome hunk. As I walked toward his table, his tablemate came to our table, frightening my poor hubby who was terrified of being ‘made’. I sat down at this fellow’s table and we started to make small talk. He was so charming that I decided to bed him and after a discrete time we rose and went to his room where of course we proceeded to fuck -- noisily.
My husband chatted with his new acquaintance that had ‘made’ him immediately. The fellow -- Grant -- told hubby that he understood and that he was gay. He explained that for cover purposes he traveled with his friend also a well known golfer. Hubby complained that his wife wandered off with this hunk. Grant suggested that they also adjourn to his room. Approaching Janet’s room, Hubby could hear Janet screaming with joy at the good fucking she was receiving so Grant led him away to their room where Hubby engaged in anal and oral sex. Days later Hubby had hardly seen his wife who spent most of her time on her back being fucked, fucked and fucked some more.
“Janet” asked Laura, “Returning to the discussion of submissive men, have any of the submissive men described to you the process, the events in their lives that resulted in their becoming so submissive that they debase themselves so completely?”
“Laura they have no idea why they are submissive. It just happens. Certainly it is possible that a psychiatrist could fathom the problem but for you and I -- no!”
“Well… Is a sub also a sub to a man as well as a woman?”
“Possibly but generally only to one gender. It is also very difficult for a sub to find the ideal master or mistress. The sub may be brutally treated -- far beyond his desires or capability to withstand the treatment. The sub may not be treated harshly enough for his tastes. By the way, the same may be said for female subs.”
“Well Janet, what about Jay -- or Jane -- if you prefer?”
“Jane had sub tendencies. I knew that when I found her clothing stash and debased her from that point until she reached the point you see her at now, wearing a maid’s costume with her very high heels. She loves them, she loves the costume. She has become a submissive. She is thoroughly debased and we will divorce. I found the process so entertaining that I decided to continue with other men. Someday I might do a film featuring a submissive. It could be fun, putting a few whippings on screen. I’d have to find the right actor. He must be attractive and have acting experience. It will take some research to be able to place myself in that mindset and write a suitable screenplay.”
I listened with chagrin and deepening horror realizing how far I had sunk as a man. My disgrace and humiliation were such that we divorced immediately. Months passed as I continued my dressing and eventually entered into therapy and then HRT. I am an authentic shemale now with lovely breasts and a superbly functioning cock and am now planning SRS. Ironically had it not been for my wife, I might never have taken this route. She is still producing adult movies. From the list of her productions, I assume she is doing well.
Since I am having financial problems I decided to contact her and inquire about a job.
“Jan, it’s Jay. I understand that you are doing very well in your business. I’m not doing so well since people know more about me than I like and I suffer discrimination and I find it difficult to find work. I have even tried ‘the street’ but it is fraught with hazard and grossly demeaning. On the plus side, I am very pretty -- thank you -- and I’m wondering if I could work with your production company as a shemale.”
“I’ll consider it. If I do employ you, it’s simply a business decision. We will have no -- repeat no -- contact outside of business. Fly out here and we’ll test you, do some training and we’ll see. No guarantees, mind you. You must produce, do the job, do it well. We have no room for inadequacy. We’ll pay you enough for expenses but profits must flow before you earn real money. Oh yes, one more thing -- you may perform many very debasing acts as part of a performance. You will do as asked or you will leave.”
“Uh Janet, uh what do you mean, debasing?”
“No questions! Are you coming or not?”
Having no choice but frightened I said I would depart the next day.
Dressed discretely but fashionably I arrived at the studio a few days later. I could not afford a flight so I was forced to take a bus. I was dressed as a woman but as my beard grew I had difficulty in entering the ladies’ restroom to shave. I was ‘made’ and experienced several embarrassing squabbles. My hotel room was less than adequate.
Feeling rather low I introduced myself to the receptionist and asked for Janet. She curtly told me to go into dressing room ‘C’, strip and wait for instructions. I did so and sat down and waited. Eventually Janet entered, said nothing but looked me over. She left and was replaced by a woman carrying clothing and accessories. The dumped them on a couch and told me to dress from bottom up, inside out. I dressed. Lovely ensemble. It was a short blue maid’s dress with petticoats, garter belt, stockings, seamed and a pair of gorgeous blue patent pumps.
“Alright Jay, screen test now. You’re dressed. You’re a maid in this house. The owner knows that you’re a shemale, that’s why he hired you. You’ll be dusting in the dining room, he’ll enter, bend you over the table, pull your panties down and fuck you. Your job is to pull your ass cheeks apart to aid his entry. This is not a surprise for you, he does it daily. After he squirts in your ass, you’ll kneel and suck him up to an erection again. When you’ve sucked him off you’ll pull your petticoats out of the way and fuck him in the ass. Understood? Yes! Get to it! Cameras guys!”
I could not believe what I was supposed to do. I had not even done this when working the street. I had no choice. I was supposed to be an actor. I’d better get to it. He entered, I kissed him, he pointed to the table, I bent over, pulled my panties down, spread my cheeks and waited for him to lube me. I felt the tip press against my anus. I relaxed as best I could and invited him in. “Honey, gently darling, at first.” He pressed it in farther while I wiggled my ass, aiding his penetration. I gasped. He pushed harder. “Ahhhh.” He passed the sphincter. Easy going now. The pleasure, the joy started now as he thrust in and out. “Honey, stroke deeply now please, way in, way out. Ohhh my God, deeper, deeper honey please. Make me yours, make me your slave maid.”
“I’m almost ready Fifi, a little longer.”
“Faster Honeyyyy, faster, harder, deeper. Shoot Honey, I’m ready! I’m ready! Please!”
With a mighty grunt he slammed his cock deeply into my rectum, spurting again and again. Resting finally collapsing across my back. We breathed deeply, waiting.
“Cut! Scott, pull out, clean up rest until you’re ready for Jay to suck you to an erection and an orgasm. Jay, don’t you dare cum. After you suck him off you must fuck him so keep your stamina up. Now listen Jay. While you‘re resting the camera will shoot you as you undress and prepare for fucking Scott. I want you to pull of your dress and petticoats leaving your garter belt, stockings, pumps and matching bra. Keep your panties on and stroke your cock while you‘re waiting for Scott to revive.”
Scott revived quickly -- I was so cute -- and I knelt before him and started to suck. I was inexperienced but he didn’t seem to mind. I sucked every which way I could, eliciting cries of pleasure from Scottie and finally with a surge and cry he squirted, spurted and poured into my mouth. I swallowed as quickly as I could finishing by holding his now limp cock in my mouth, sucking gently, gazing up into his eyes.
“Cut! Good job Jay. Now the final segment where you fuck Scott. Same table Jay, bend him over, pull his jeans, panties down, lube yourself. Now show us what that big cock of yours can do. Make him squeal. Make him beg for more.”
“Well Janet, how’d I do? Am I hired?”
“That was good work Jay but I have some really bad ass stuff for someone to do and I guess you got the brass ring.”
“Uhhh, bad ass? How bad? What stuff?”
“A girl is going to ask you to do something distasteful, you will refuse. You will then find yourself chained to a cross and flogged -- brutally. Your genitals will be whacked, you will scream. You will agree to submit. Your ankles will be chained, your neck will have a collar. You will be led to a bench where a dog is standing. Your job is to suck him to an erection so he can fuck one of the actresses then to your surprise you will be forced onto all fours and the mutt will fuck you.”
“Oh God Janet! Do you really hate me so?”
“You are an employee in the sex industry. You will do as asked or leave. Very simple.
Do it or go.”
“Oh shit Janet! I’ll do it. I have no choice. I need the money, I need a job. Let’s get to it. What else do you have in mind for me?”
“Hmmm, my films showing my fucking others are simply professional output. To get personal I’ll have to fuck some men -- friends -- in front of you to reinforce your status as my little cuckold. Hmmm, yes. That’s what I’ll do, and you, cuckold will be chained to a cross watching us. Yes, watching me fuck our brains out, screaming howling with unbridled passion -- for your benefit. Yes, we’ll do that shortly after I arrange the men. I want more than one man to fuck me. Hmmm, yes, how many? How many men will fuck me for… your… benefit. No I don’t hate you, I just don’t… even… think… of you -- cuckold.”
“Oh my God Janet you do hate me. I’m so sorry Jan. What the hell did I ever do to make you hate me so?”
“Nothing really, it’s just the way I am, perhaps this business is warping me. Oh yeah, Jay we will be shooting this exhibition so make it good. Tomorrow Jay. I think that five studs will be enough. I’ll be fucked to a frazzle and I’ll be so fucking happy watching you hang in chains against the cross never able -- never again able to fuck me -- me -- your former wife.”
© 2009 Janet Baker
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