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Crossdressing

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27

Dad Pimps Me Out

I think once dad caught Jack fucking me,he wasn't upset,but more so he thought of a way to use this to his advantage. After that it was nothing for me to walk around the house in womens clothing,for my dad and I had a talk and I told him that it felt right. One night when he brought home a sexy outfit for me,I knew he was up to something. He handed me a bag and said "here,go put this on". ...Read On

34

Two girlfriends have a couple over for a fun night

Wife sets up night for us to be girlfriends, then invites another couple over for fun

My wife Dawn had surprised me by saying we were spending the night in as two girlfriends, laying out my clothes so we matched. Then after having amazing sex, Dawn surprised me by telling me that she had invited her friend, Maria, and Maria’s husband, Mark, over for some fun with the two of us and to fulfill the fantasies of all of us. So I was standing there with my red plaid skirt,...Read On

45

The Feminization of Michael - Chapter 1

The Feminization of Michael. Chapter 1 How I had found myself in this predicament Ill never fully understand. Ok I guess it was my own fault but why I didn’t kick against it when I could Ill never know. I had been involved in a sordid night of drink drugs and sex with a young transsexual hooker! Including her/him putting a bra and panties on me! I didn’t know any of this until my...Read On

90

A helping hand

Found out by a mature woman

It all started a few years ago. I was dating a girl who was bisexual. So much so that she wanted me dressed as a woman for sex. To begin with I was not sure, but eventually I came round to the idea. It was mainly just some lipstick and perfume. After a few months we split up, but I continued to dress up. One day I decided to venture out as a woman. I lay in bed thinking what I should wear....Read On

27

Truck Stop Tranny Sluts

Steamy Tranny encounter at a truck stop

My girlfriend and lover Candi and I were driving back to her place for some steamy tranny sex after a night of partying at a tranny/gay bar in town when we passed a truck stop on the highway. Buzzed and horny as we were, we laughed about stopping in the lot and doing so hookin’ as a means to get us some trucker cock. After a minute or two of silence, Candi said lets do it and before I...Read On

57

Miss Teresa's Beauty School

Princess has been caught stealing at work and has to pay the price!

I wrote this story as a narrative and I made it into a 45 minute audio story. The Interview: Come in, I've been expecting you. I had a long talk with your boss the other day and it seems that you have a little fetish for women's underwear, isn't that right? In fact-you've been caught stealing things from the other girls lockers. Mostly their panties and pantyhose. Is it just too hard to...Read On

57

His Dirty Little Secret

His wife finds his stash of clothing, leading to some role reversal

Julia was doing some spring cleaning in the house. She had scrubbed everything, cleaned the oven, scrubbed the floors and was in the process of cleaning out the closets. Stuffed in the back of a closet was a bin. She didn’t know what was in it. The sight that greeted her caused a jumble of emotions in her. The bin was full of women’s clothing. It was all silky and sexy; Nightgowns,...Read On

27

Our Sissy Slave

Will you be our full-time cross-dressing lesbian boislut?

Let me remind you how you came to be in this situation before you refuse. I've been bi-sexual since I was old enough to have noticed how horny women made me. From the moment I noticed, I was unstoppable. My dominant personality seemed to bring me more girlfriends than I could really use. But I always thought the only thing better than a submissive girl is a submissive boy. And what...Read On

32

She wears the pants, over her cock

I stepped off the plane after three days travelling and was looking forward to going home after a long few weeks of travelling for work. My work regularly has me travelling and I don’t seem to get home as much as I would like anymore.   But it does make it even more enjoyable when I do get home.   Leaving the gate, I walked down the corridor, past the last security checkpoint, and toward...Read On

78

Vicky's First Time

My first time having sex as Vicky

I was very open about crossdressing when I met my wife when we were in our 20s. She has been very supportive and helpful. She helps me with my hair, makeup, and picking outfits. We started having sex with me dressed up as Vicky. This soon escalated to her taking me with a strap on. I loved the times she would fuck my ass with her cock. I had never considered myself gay or bisexual but the...Read On

46

Caught in my girlfriend's lingerie by her friends

My girlfriend lives alone, so whenever I am at her house by myself, while she's out clubbing or working, I always take the opportunity to go through all of her sexy clothes and lingerie and dress up like the slut that I crave to be. I undressed and put on a pair of white fishnet stockings, a black thong, mini skirt, black and white see through top and a sexy pair of silver high heels. I set...Read On

10

s(he) finds her man

story when i replaced my friend at a wedding

My house was not more than 250 meters away from the bus stop where I got down; but the sudden and heavy downpour caught me totally unprepared. Being one those new housing colonies there were no houses or trees where I could take shelter. By the time I reached our new house I was drenched to my skin. My younger sister Putti who opened the door started laughing at my plight. My elder...Read On

29

Friend's Treat

A divorced man gets a treat

I had recently split with my wife and was feeling very down. I was invited to spend a few days with my old friend Dave and his wife Tracey. The first night I was there Tracey turned to Dave and said that we needed a boys' night out and why not go to his club. Dave agreed it was a good idea and within minutes Tracey was dropping us outside what appeared too be a Georgian townhouse. I...Read On

12

Caught and the Consequences Part 2

Crossdresser caught by wife finding our what she has in store for him

Part 2   While sitting there I went through the usual stages, despair that I had been caught, fright as to what would happen next, would she still want me as her husband or was this going to be a third divorce, and that made me feel very sad as it suddenly dawned on me how much I loved her and I quietly resolved to do anything I could to save my marriage.   ...Read On

27

The Worm Turns-Part 1

My submissive girlfriend turns into my dominant wife

I must have read about a million of these stories and I have to confess that mine isn’t so unique--maybe only in the details, but not so much in how things started or how things ended. You can probably write the first lines yourself: “Things started out so innocently. We had a typical relationship that somewhere, some way, took a dramatic turn that I never saw coming. At first, I was all for...Read On