My Little Cuckold

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 it.

My Little Cuckold

By Janet Baker

Copyright © 2009 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.”


“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!   You want to attract men? My God!   What the hell did I marry?”

“Janet.   No! I am not a pervert! And I don’t want to attract men and 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.   H’m, 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!”

I was, but I felt a chill!   Something seemed wrong here.   She can’t have changed so much so quickly, I was thinking, … 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 — any more?”

“Yes.   One of my fantasies is turning real.   I’m going to Hollywood to do a screen test.”

“You’re kidding!”

“Hell no! Why not! I’m pretty and you know I’ve acted in lots of amateur works in college, and in our regional summer theater here too.   Well, the   director of that play I did last summer is working in the film industry now.   I told him some of my ideas -- some of your fantasies really --   and told him I was willing to act them out on camera.   He thought the ideas had potential and he’ll set me up for a screen test.”


“Not sure, probably within weeks [he says]. I’ll let you know.”

“Sounds great Jan, I’ll see if I can get time off from work.”

“Well 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 and found a note from my wife telling me she had gotten a call and flown to Hollywood on regrettably short notice and expected to return in a few days.   She told me to enjoy myself in my special way.   So I consoled myself by buying some new shoes and a new dress.   She didn’t leave a phone number and I saw she had also 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 had 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, you left your cell phone home, 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… A bit shocking I think.”

“You’re shocked?   Just wait darling, you ain’t seen nothing 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 maid’s 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 have been cuckolding him for some time with many men friends -- real men-- and finally, I had a great time in Hollywood, and 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! Cuckold! 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 my little cuckold performs 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.”

“When   I discovered my inadequate spouse dressed as a woman,” she confided with a faint snicker,   “I decided to leave him and strike out on my own. So I started aiding his dressing, helping him become more and more of a woman and less and less of a man, so I’d have no regrets when I finally left him.   He cooperated in everything, and I have some delightful photos as evidence. He then began telling me about his fantasies, and I told him about mine.   He had no idea, but I started incorporating those fantasies into screenplays for pornographic movies, and sent them to the director I knew.   I indicated that I would be interested in participating as an actress and principal. He showed them to others in the porn business and not long ago I made arrangements to visit Hollywood.   And there I commenced 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 hell! Look at yourself in the mirror Jane… all dressed up to serve…
to serve… to be submissive… to be submissive to me.   Look at yourself.   Aren’t you soooo pretty with your corseted waistline, your fetish heels, your black satin maid’s costume, you net stockings.   You are no longer a man!   You are…”

“Janet this was not my idea.   You have perverted my modest desire to cross dress.   I don’t like it!   I don’t like what you’re doing.   This is so humiliating.”  

“Whether you like it or not, I’m doing it!   I have a website.   My work is under copyright 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, these segments are all mine, my screen plays, my imagination, the fantasies I wanted to make real, though some of them are based on Jane‘s imagination..   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 bring about a divorce!”

“Sorry, Jane but the divorce is already a foregone conclusion.   Now sit and be entertained.”

“You mean sit and be humiliated, appalled, disgraced, disgusted?”

“Yes Jane, all of the above!”

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 had written 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, especially if it was my wife.

Over the weeks since she had caught me dressed I had became increasingly convinced that I might like to be a woman… not to perform as she had now done but simply to be one of that preferred sex.   I’d become more and more content with dressing modestly, part time, as a woman.   As I watched her DVD I realized that this divorce could provide just the opportunity to further my explorations into femininity.

The following segment showed her tying herself up, immobilized while waiting for a husband or lover to release and take her.   She tied rope around her ankles and then her 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, and finished by carefully putting her wrists in cuffs behind her.   She was totally and irrevocably restrained by herself, unable to do anything until he — or she — arrived to release her. Her release was unexpected!   Her apartment was invaded by three men seemingly intent on burglary.   They discussed her predicament and ungagged her but left 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, pleaded, cried, 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 you’ve been doing very good 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!”

In the months that followed Janet starred in numerous segments, some of which were too intense to be recounted here but may be found on the sites where they’re offered for sale.   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.   There were other acts too extreme to be noted here but again may be found described elsewhere.

My disgrace and my humiliation were such that we divorced immediately. More months passed.   I continued my dressing and found increasingly that I loved it.   I eventually entered into therapy and ultimately HRT.   I became a rather attractive shemale with lovely breasts and a sterling cock.   I am my own best wet dream and I 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 assumed she was doing well.   After my SRS, I may ask her for work in one of them.   After all, by then I’ll know how both sexes feel when they’re living their fantasies.

So I evolved into a functioning shemale.   Without my wife, unmarried, and a shemale, normal relationships were beyond question.   I knew I was a freak of sorts with the ability to satisfy only a limited percentage of the extant population but I loved it!   I loved my appearance.   I loved to dress.   My career did taken a turn for the worse, because my evolution to shemale caused serious employment problems and I found I had to find a new source of income.   I found some work on the streets.   Not enough, so…. I called the number on my former wife’s website.

“Janet it’s me, Jane.   Are you still doing films Janet?”

“Yeah, so….?”

“Janet I have a long story to tell you.   I am now a shemale on my way to SRS.   I need money.   Due to my transgendering I have job problems.   I am very pretty and wonder if I could perform in a picture of yours.”

“Hmm, maybe.   Hmm, email me some photos, nude, dressed.   No hair.   I want you to be shaved -- totally.   Well, not your head, stupid.”

“Chill out Jan, you started me on this path.   I’m in trouble now.   I’m left with nothing to do but hook. Hooking as a shemale can be tricky… can be dangerous.   I’ve seen your films.   You do well -- very well… and I was hoping that perhaps… you might use me.”

“I… think… so… Yes… I believe that I may be able to use you if your photos are satisfactory.   If I’m pleased I’ll send you plane fare and we’ll do some screen testing.   The work is not just sex but real acting.   I’m developing longer and better films that emphasize story more so than just simple bang bang thank you ma’am shorts.”

“I believe that I have developed some experience in acting.   It’s been necessary as part of my ‘profession’.   In any event, I’ll do my best.”

“OK Janey, let’s see what you can do.   C’mon out to LA.   We’ll see.”

“Thanks Jan, ‘see you soon. And thanks again.”

Janet met me at the airport, took me to a motel within walking distance of her studio, showed me a nearby diner, left a script with me and departed, telling me to come to the studio in the morning.   The script presaged more and indeed excessive humiliation.   I called Janet and complained but she told me to shut up, learn my lines, or leave.

The next morning, having little choice, I appeared on time at the studio and mentally prepared myself for the ordeal.   The script called for me to be a humiliated, ravaged victim of my wife.   She and a lover were to strap me to a bench.   She was to wear a strap-on and fuck me in the ass while her lover was forcing his cock down my throat.   I was determined to be a success so I did my best to be convincing.

Janet reviewed the take and cried out, “Jane, you were great!   Good job! The action was quite realistic, believable!   You’re hired! I have a shemale script I want you to study.   I think that you have a future in porn but you must realize that we have relatively short life spans as porn performers.  

She was right.   We have since made many films, but they are being   released gradually to keep up interest in the works of the featured performers.”



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