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It Started With A Date

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If the idea of feminized men, transsexuals, crossdressers of sex changes offends you, then stop now, this story is not for you.

This is a work of erotic fiction. Any resemblance to real people and situations is entirely coincidental. All of the characters in this story are over the age of 18.

I appreciate getting feedback, both positive and negative, as long as it is constructive. I will not hesitate, however, to delete any nasty or abusive anonymous comments. I enjoy corresponding with my readers, and if you send me an e-mail I will respond.

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I stumbled upon a picture of a rather hot looking cross-dresser a while ago and it looked like (s)he was dressed up for an evening out. For some reason, the idea of this man dressed as (s)he was, going on a date with his wife and her lover was intriguing. I really had no idea where this one was going to go but I knew I had to at least start with that idea and let it develop.

.....

I guess what makes my story so strange is that I never fancied myself as a woman. Never thought of myself as being born in the wrong body. Never, ever thought about sex with men. I just enjoyed dressing up in women's clothing.

Now, I suppose that last bit is not really all that strange either. At least not if you have ever surfed any of the millions of transvestite and cross-dressing sites on the web, but it was strange enough in the world in which I lived.

I don't suppose there's any sense in starting way back in the beginning, since who among us has the perspective to see our own past and what events triggered our current individual fetishes? So I'll start with my relationship with my wife Wendy.

I was very up front with Wendy about my penchant for wearing women's clothes right from the beginning. I had long ago discovered that surprising a woman with that kind of information after you had been dating a while did nothing to extend the relationship and everything to shorten it. Although I can't say she was enamored with the idea, it didn't send her screaming from the room.

As our relationship progressed, Wendy made it plain that although she accepted my cross-dressing fetish, she had no interest in lesbian sex, and therefore, no interest in sex with me while I was dressed. After laying down some ground rules about dry cleaning bills and closet organization, she even allowed me to borrow pretty much any of her clothes with the exception of her undergarments. Those she kept completely off-limits, although it didn't stop me from coveting some of her finest lingerie.

After we were married, we slipped into a routine where I worked my software company from a home office and she took a position as a legal secretary at a small law firm downtown. During our first year together things were great. We were in love and still willing to overlook each other's flaws. Being home alone, it slowly became normal for me to dress "en femme" almost every day.

After our first anniversary, Wendy's acceptance of my dressing started to wane. I was wearing a lot of her clothes and she often went to the closet looking for a dress or skirt that I had worn and sent to the laundry. This whole thing became a thorn in her side and she became increasingly reluctant to share her wardrobe with me, comparing me to a bad roommate.

In the mean time, our sex life had also changed. True to her word, Wendy had little interest in sex with me when dressed, and since I was dressed almost every day, our relationship declined even more to that of roommates.

Although we still professed to love each other, our marriage was clearly in trouble. Then just after our second anniversary, Wendy's attitude changed for the better. She had an almost sunny disposition I had not seen in over a year. She signed up for evening classes at the local college and even started going to the gym. In retrospect, I should have seen the signs, but I was so happy to have her happy, my eyes and mind were closed to it.

About 6 weeks after life got better, life got worse. Wendy announced that she had been having an affair and that she was finally getting what she needed from a man. She claimed that she still loved me, in a more sisterly sort of way, but indicated that even though it had stared out as a fling, something that "just happened" because she was so sexually frustrated and unhappy, she would be continuing the affair indefinitely.

I was dumbstruck. I asked for some details, which she seemed happy to supply. He was a local Veterinarian, unmarried, handsome and fun-loving. He liked to take her out and show her off, and he dressed like a man. All the time. Yes, they had been having regular sex, and he was very good in bed.

Then she dropped the bombshell. Apparently she and David had talked at some length about me and my fetish, and he had asked if he could meet me. Wendy then told me that she had agreed and that we would all be going out to dinner on Friday night.

My mind was reeling. He wanted to meet me. Meet his lover's husband. Take us out to dinner. What in hell was he thinking? That we would all be friends or something?

Then as if this hadn't already been unbearable enough, Wendy threw in that I was expected to "dress" for the date, and she wanted me to go all out to impress her lover. We were to be two roommates on a double date. Taking my stunned silence for acquiescence, she continued on to describe how I was to dress, giving me access to one of her sexiest little black dresses.

I could see it all in my mind's eye.

"Oh yes this is David and his girlfriend Wendy. That guy? Oh he's just Wendy's husband. He likes to dress like a girl. Pay no mind to him."

Over the course of that week, Wendy took great interest in my appearance. Even though I was never particularly hairy, she insisted I use a depilatory cream to remove all traces of manliness and a bronzer to give my skin a warm glow. She waxed and thinned my eyebrows and I was shown repeatedly how to apply makeup. She insisted that I make an appointment at the beauty parlour and have my hair done to achieve my most feminine appearance.

I had never been able to share Wendy's shoes since we were quite different sizes, so she bought me a pair of black stilettos with a sexy ankle strap in my size and made me practice until I was comfortable walking in them. Finally she made me practice pulling my cock and balls back between my legs and binding them there.

"After all this work making you presentable, I do not want you to embarrass me in front of my boyfriend by having your dick bulging out under your dress."

There's a sentence a guy never expects to hear from his wife.

When Friday finally arrived, Wendy's parting instructions had been clear. I was to be ready, bathed, tucked, nails painted and in full makeup with every hair in place by the time she arrived home so she could get ready without any interruption from me.

"It will never do to have two girls trying to get ready for their date in the same bathroom at the same time and I want you done and out of my way."

I would be allowed to put on the thong panties garters and hose she had supplied me for tonight, but the dress and shoes were to remain in the closet until just before I was presented to David.

And that's exactly how she found me when she breezed into the bedroom after work. I stood stock still as she cast an appraising eye over every part of my body, nodding and smiling. When she was satisfied that I had passed muster, she pulled out a small bag from her purse and told me to come to the bathroom and stand still.

The breast forms were no more than a small C cup, but when she glued them to my chest they looked enormous as I looked down at them. Wendy cemented them to my chest, told me to hold them there until the glue set, then scooted me back out into the bedroom. When the glue finally set I removed my hands from my new breasts and I stared into the mirror in wonder. What was I becoming?

Wendy came out of the bathroom and told me to get on with it. It took me only a couple of minutes to slip into the little black dress and buckle up the stilettos. This time when I looked in the mirror, I was completely stunned. There looking back at me was a very attractive woman dressed for an evening out. The breast forms were perfectly sized and placed to ensure that the dress hung properly over my body. As I looked at the vision in the mirror, I felt a stirring in my groin and was glad Wendy had dictated that I tuck myself.

"David wanted me to give you a little something for your nerves," Wendy announced as she handed me two little tablets. "Go take these while I finish my make up."

I didn't know what they were but I was certain that Wendy would never do anything to harm me so I trotted off to the bathroom and swallowed them both.

It was only a few minutes later that the doorbell rang. I suddenly knew how a schoolgirl feels on her prom night. My tummy did a flip and I felt a strange tingle all over as Wendy told me to wait while she answered the door. I stood riveted to the spot as I heard his deep voice answering hers and then silence as I imagined their greeting kiss. It took a couple minutes before Wendy called for me to come down.

Four eyes followed my every step as I descended the stairs. Wendy was smiling as was David. When I reached the bottom step, Wendy turned to David,

"Honey. I'd like you to meet Terry. Terry this is my boyfriend David."

"Pleased to finally meet you Terry."

He was a tall fit looking man who appeared to be fully at ease with himself and his surroundings. My first impression was one of confidence and strength. His smooth deep voice filling the room. Even in this strange circumstance, I somehow found myself immediately attracted to him.

"Wendy has told me a lot about you and your situation, but she failed to mention how lovely you were."

This whole scenario was so insane that my mind refused to function. Another man might have shouted a curse, another might have hit him, I was neither of those men. For some reason, (was it those two little pills?) his complement warmed my heart. It felt good to be appreciated, and I found myself liking him even more because of it. Strangely, I found myself wanting to please him to have him like me too and somehow unconsciously my voice took on a slightly feminine timbre as I simply thanked him for the complement.

Wendy led the way into the rec room where David chivalrously opened, then poured us each a glass of the wine he had brought. I was still a bit shell shocked and kept mostly quiet as the two lovers chatted with each other and Wendy described all the work she had done this week to get me ready.

I couldn't help but notice David's eyes passing over me repeatedly, lingering on my chest as she described the breast forms, then pausing to inspect my legs and stilettos when she mentioned them. I'm almost sure I saw him try to sneak a peak up my dress as I nervously crossed my legs while they talked about me. It didn't make any sense to me, but I found myself enjoying his attention. Each time he looked away, I felt a slight tinge of jealousy. Where did that come from?

I was so nervous and confused by my reaction to this whole scene, that I drained my wineglass rather quickly. Being a gentleman, David picked up the bottle and came to refresh my glass. His strong hand covered mine as he steadied it to pour me my refill. It felt strange, exciting and confusing all at once. I had been dressing as a woman for years, but this was the first time I had acted the part with anyone, let alone a handsome man. Why was I so attracted to this guy. He was my wife's lover, not mine.

"Drink up girls," he intoned after looking at his watch. "Our reservation is in 30 minutes and we have to get going."

The combination of the wine and my excited and anxious state caused me to stumble in my heels as I stood. Luckily, David was standing there and was able to grab my waist to steady me. I felt the warmth of his strong hands through the fabric of the dress as he held me until I was steady on my feet, and was completely unprepared for the warmth that it caused to spread through my crotch. What in hell was wrong with me?

Placing one hand on the small of my back, David guided me through the house and out to the car. Opening the door for me he apologized profusely for having me sit in the back, and held my hand gently as I slid into the seat, showing him a hint of stocking top before he closed the door and helped Wendy into the front.

I was extremely apprehensive when we arrived at the restaurant, but David and Wendy both said I was totally "passable" and had nothing to worry about if I just kept a feminine tone to my voice. At the table, the wine flowed freely and David was a kind and generous host. I found myself increasingly enjoying his company and his sense of humour as the evening passed. It was the strangest feeling. Almost like falling in love. But he was a MAN!

The coffee after dinner was insufficient stimulant to offset the wine I had consumed and I found myself quite tipsy as we stood to leave. Once again, David was there with a steadying hand. This time he wrapped his arm around my waist and steadied me all the way out to the car. I'm pretty sure he was rewarded for his chivalry with a vision of my bare ass as I stumbled my way into the back seat.

The ride home was very quiet, almost anticipatory and I nearly nodded off a couple times as we made our way back to the house. Ever the gentleman, David took Wendy and I each around the waist and walked us to the front door. A jolt of adrenaline shot through me, making me instantly sober. We were back home and at the front door. What now?

Wendy fished her key out of her clutch and handed it to David, who opened the door and ushered us both inside. Pushing the door closed behind him, David wrapped Wendy up in his arms and pasted his lips to hers. I watched in stunned silence as their lips parted and tongues fought with each other. A pang of jealousy sliced through me as I realized that she hadn't kissed me like that for a long, long time. I suddenly wanted someone to kiss me like that. Then after that thought passed through my mind, I was shocked to realize that it wasn't Wendy that I wanted kissing me, it was David.

After a couple minutes of heavy necking Wendy broke off and pulled back.

"OK Terry. David was nice enough to treat us to a night out, the least you can do is give him a nice good night kiss."

Before I could react, David slipped his arm around my waist, pulled me close and kissed me. Hard. His lips were hardly touching mine before he was pushing his tongue into my mouth and Frenching me just like he had been doing to Wendy moments before. Unfamiliar emotions coursed through me. Up until that moment, I would have bet money that I was not gay, but I couldn't deny that I really wanted him to continue kissing me. My brain screamed no, but my resistance melted as unbidden arousal coursed through me. It had been months since Wendy and I had any kind of sex and this stimulation, however unwelcome was turning me on.

As I was focusing on the the feel of David's slightly rough face and lips, I hardly noticed his hands moving to my ass cheeks. I broke the kiss long enough to say no, but my weak rebuff was ignored as he dug his fingers deeply into my flesh and kissed me again.

"All right you two. That's enough. C'mon David. Let's take this upstairs to bed."

"Terry. David and I are going to turn in. Why don't you go on into the guest room? I think you've had enough excitement for one night. Just make sure to get all your makeup off so you don't ruin the bed linens OK?"

The next thing I heard was her giggling and the sound of the bedroom door closing behind them.

After cleaning up in the guest bath, I crawled into bed alone. I could clearly hear the sounds of lovemaking from the master suite. It was obvious from the squeals and grunts that Wendy was enjoying David's efforts as much as he was hers. Jealousy and envy fought for top billing in my mind as I visualized them together. Jealousy that he was getting the sex I had so long been missing and envy that she was the object of his desire. Where had that come from?

It was a fitful night's sleep for everyone. I had been unable to pry off the breast forms Wendy had glued to my chest leaving me to toss and turn in vain attempts at getting comfortable. David and Wendy had a restless night too. I heard them wake several times to make love. The sounds of their passion clearly audible from down the hall.

In the morning, I awoke to the realization that all my clothes were in the master suite with Wendy and David. I had nothing else to wear, so I simply slipped back into the little black dress from last night before heading down, barefoot, to make coffee.

It wasn't long before I heard David enter the kitchen humming. He was obviously naked under one of my disused men's robes and I was totally unprepared as he walked up to me and patted my ass.

"Nice outfit," he opined. "I'm not sure I told you last night how much I like the look of your legs and ass in that tight little dress. It even looks good without the heels."

The robe was quite small for his frame and he was rather lax about keeping it closed as he moved around the kitchen and filled his coffee cup. I noticed the front of the robe open several times as he moved and then it opened enough to reveal a rather large cock hanging loosely between his legs. When I glanced back up he was looking at me and smiling as he pulled the sides together.

"OK Terry, show's over for now, but maybe I'll let you see some more another time."

Another time? Why would I care. I'm a man. I've seen plenty of cocks in my day. At the gym, in the restroom, on the Internet. Plenty, yes, but never while I was standing barefoot in the kitchen wearing a little dress from the date I had been on with that man the night before. Embarrassed, I looked down at the floor and for some reason I could not fathom, I hoped I would get to see him again. Why was I so attracted to this man?

"Listen Terry, I like you and I want to make you an offer. My receptionist at the practice is going away on maternity leave starting next week. I was hoping that you would consider filling in for her while she is gone. Just to help me out. I'll pay you, of course. How about it? Will you help a guy out of a jam?"

Oh I wanted to. I really did. For some reason I had bonded with this man. I liked him, I wanted him to like me, and I wanted to be near him. My own business was actually pretty slow right now and there was no real reason not to help David out.

"I don't know David. I don't have any veterinary experience and I don't have any appropriate clothes to wear. What will Wendy say?"

"The practice uses a uniform service, so I'll provide the uniform. Nice white starched dress, mid thigh length, name tag, the whole deal. I've already spoken to Wendy and she's OK with it. What do you say? Will you help me out?"

A tornado of thoughts whirled through my mind. A white starched uniform dress? Why did I want to please him so much? Passing as his female receptionist. No I can't do this. But why do I want to so badly? I'm not attracted to men. Dressing for him every day. Why had Wendy agreed? What has come over me? I'd have to be totally hairless. I'd have to wear the breast forms every day. I wonder if I should wear stockings or pantyhose? I wonder where I can go to buy a pair of those white shoes?

The last four thoughts made me realize that I had already unconsciously made my decision. A warm happy feeling passed through me as I looked up into his smiling face and agreed to work for him.

"Great," he enthused. "I'll call the service and have your uniforms delivered tomorrow. Now. You run along upstairs and make yourself pretty while I fix my girls a nice breakfast."

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