Crossdressing Stories

10

Heytherebaby

Becoming John Collins' Mistress - Part One

I get to know Mr. Collins and get invited to meet his friends

Hi. My name is Chris, though some know me as Christine. I am John Collins’ mistress. We care deeply for each other. John “keeps” me. He supports me financially and in return it is my pleasure to keep his sex life exciting, as well as entertaining any of his gentleman friends who drop over. It all began innocently enough, I suppose. I had just turned eighteen and had moved out from my...Read On

15

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CourtneyFux

Sexy Stewardess on a Hot Flight: Part One

Working as a tranny call boy leads to a high flying adventure.

After arriving in Los Angeles, I became a tranny call boy to support myself. Working for an agency, I was sent to perform sex on many older rich men. Being a hot twenty year-old tranny slut with fresh meat in my panties, I instantly became one of the more popular call boys in the agency. Some men even took me out on dates for dinner then back their places or motel rooms for lots of sexy...Read On

38

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Tanksdad

Who Knew a Physical Could Be Fun

Discussing Lush had an added benefit.

I woke up grumpy. I couldn’t eat or pee this morning. I had a physical scheduled for first thing this morning. Even worse, the doctor had warned me that today I even got a prostate exam. Oh well, I hope his hands aren’t too big. I arrived at the doctor’s office early and waited for my turn. The nurse ushered me into the exam room and drew blood then gave me the little plastic cup I had to...Read On

22

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HollyInPantyhose

Adventures in a Woman’s Body – Chapter 2: Tease and Please

Things are happening under the table

After I got out of my house, I walked for about 20 minutes to get to this fancy restaurant I made reservations for. It was a long and tiring walk, but I loved cat walking in my sky-high stilettos and hearing the click of my heels with every step. I couldn't pay much attention to what was going on around me as I walked down the streets. I was focused on swaying my hips and crossing my heels...Read On

19

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Heytherebaby

Meeting One of the Neighbors

I meet one of my neighbors and he invites me over for drinks.

Tom was almost seventy. We lived on adjacent streets and his property backed on mine. I had moved in only a couple of weeks earlier. I was renting the place. I was so excited to be on my own at last, especially because I loved to crossdress. My new freedom was exhilarating. One day I’d been in my back yard in the late evening, dressed in a cute white bikini. I was lying face down on a...Read On

28

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HollyInPantyhose

Adventures in a Woman’s Body – Chapter 1: Plugging Up

Dressed up, plugged up, and ready for some cocks

After two years of hard work, I've finally come as close to being a woman as possible. The hormones and drugs that I've been taking for the past five years have made my body and voice quite feminine. With the help of toning exercises, I now have long slender legs, a soft and juicy ass, very feminine hips and a thin waist. My skin is very soft, smooth, and white thanks to the skin care...Read On

6

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CourtneyFux

Hitch-hiking Baby Doll: Part Three

My cross-dressing cross country trip continues with my trucker stud.

When it comes to getting men to want to fuck her, a girl has to put her ass to good work. I discovered this when I was eighteen and first started being a tranny hooker around the adult book store. I was wearing my first miniskirt with a thong panty underneath, walking down the street. My ass cheeks were hanging out of the bottom of the miniskirt and men were slowing down to look at me, blow...Read On

8

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hoterotica

Allen's Sweet Surprise - Part Two: The Yummy Conclusion

When my boyfriend dresses in ladies clothing I'm in for a sweet surprise.

I felt a light tapping on my bottom. "Mmmm," I said. It felt kinda good, this mysterious spanking. "You can open your eyes now," said Allen. I opened my eyes and turned around. "Meet Kandi," said Allen, blinking her lush eyelashes and smiling at me sweetly like a schoolgirl. Kandi had stunning electric blue hair and dazzling green eyes. She was sporting a pink polka dot skirt that...Read On

18

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vanessagrrl

Just For The Taste Of It

Vanessa is trained to love the taste of cum

Many years ago, before I was the experienced sissy girl I am now, I was living with a man named Jake. Jake took me under his wing. He wanted to help me become as girly as I could be. One of the things that he wanted to get me used to was the taste of cum. I had tasted it before, but only my own and his. Jake wanted to make sure that I was a cum expert. He said to me, “A true sissy...Read On

14

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hoterotica

Allen's Sweet Surprise Part One

Seeing my boyfriend in ladies clothing is sweeter than I expected.

My pussy was dripping as I zipped my car into the parking spot in front of the mall. I was having another secret meeting with my boyfriend, Allen. Only, this time we'd arranged a little twist to our usual tryst. After years of Allen and I seeing each other, I'd finally worked up the nerve to share my fantasy of him dressing up like a woman for me. It wasn't easy for me to do. I'm a...Read On

9

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hoterotica

Fucked in the Fitting Room Part Two: The Explosive Conclusion

When my lover finds a dress on the sales rack, I get more than I bargain for.

I took Allen's hard cock in my mouth and began to suck it slowly. "Oh, God," said Allen. I rolled my tongue around the tip of his cock and then ran it up and down the sides. "Suck it faster, babe," said Allen. I happily complied, bobbing my head up and down on his cock as fast as I could. I grabbed his balls in my hand and stroked them gently with my fingers. "Oh, baby, that feels...Read On

13

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hoterotica

Fucked in the Fitting Room Part One

When my lover finds a dress on the sales rack, I get more than I bargain for.

My boyfriend, Allen, loves to wear women's clothing. It's something he's been doing awhile now, probably three or four years. We both get very excited about going to our local department store to hunt for new additions to Allen's wardrobe. Last night we had one such shopping trip and we both had a luscious time. "Grab a buggy," said Allen when we entered the store. "I plan to load up tonight."...Read On

9

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ThePhantom

My First Time Final Chapter

The conclusion of this story

The Friday that Lydia told me about had finally arrived and she would be bringing some of her friends over for drinks after work, and I was to serve them as Melissa. Lydia had also advised me that unlike the dominatrix persona I used during my first outing on Halloween, Melissa the maid, was totally subservient. That morning after my usual visit to the gym I cleaned the house and set up...Read On

9

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hoterotica

Steve the Crossdressing Cat Lover

Cat lovers are a breed of their own and my boyfriend, Steve, is one of them.

My boyfriend, Steve, has a lot of cats. I can't tell you exactly how many because the little critters come and go out the pet door and scatter as their furry little paws please. Steve lives on a farm. Well, it's kind of a farm. I mean, he has a lot of land, but he doesn't exactly grow anything on it except cats from what I've seen. And he has a barn, too. You'd think with all that land...Read On

36

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hoterotica

My Boyfriend's Blue Silk Panties

a crossdressing shortie

My boyfriend, Allen, is a man's man. Let's get that straight from the start. He rides a Harley and he scoops me up in his big strong arms like I'm light as a feather (which I'm not...let's get that straight from the start, too). So it was a big stretch for me to ask my masculine lover to slip into a pair of silk panties just for me. It was a secret fantasy I'd harbored for years but had...Read On

63

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Lucy_CD

First time sex with a man!

How my first time anal started and happened.

So there is this guy who I've been talking with for awhile. I wasn't too interested because I was still on the edge about meeting up dressed with another person. At the time I was under the influence and I sent him this message. "I have recently been dressing up more as a woman as my family have been busy. I have been eating my cum all dressed up like a sissy! I have been eating my...Read On

24

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kylie_kained

The Wedding Present

Chardonnay wants to show her boyfriend and lover how committed she is to him.

Chardonnay had been Phil’s live in sissy lover and constant companion for just coming up to two years. She wanted to do something very special for him and had saved enough money at last. She phoned an exclusive hotel, giving great detail into what she required. She made a few more calls that afternoon while Phil was working. As she finished the last call, she gave a huge grin to herself in...Read On

47

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AbigailThornton

The Neighbour's Knickers - Part 1

A man who just can't resist the opportunity to get into his neighbour's knickers

It was a sultry summer night but it wasn’t the muggy air that was making me hot. It was my clothes. I’d felt the urge to dress up in a very sexy outfit. My preparations had started much earlier in the day, and they had been thorough: my whole body was clean and smooth, shaved so that there was not the slightest hint of hair anywhere other than on my head. My heart thumped wildly as I...Read On

19

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biguy2play

After the Show

An invitation to a drag show proved to be an invitation to more.

I‘d met David through my (now ex) wife. He lived in the Twin Cities with his partner Dennis. His being gay made it very easy for me to talk openly about being Samantha. He hosted a drag show on Saturday nights at a small gay bar so he’d invited me to come along, meet the ‘girls’ and see the show. I could stay the night so I could go dressed and have a fun ‘girl’s night out’ while he MC’d...Read On

29

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biguy2play

Keeping A Secret

The drive home from the Cities was always long. After work I had stopped at Kim’s to change and emerged as Samantha. I drove to the meeting and then went out for a drink (or maybe two) with some of the other ‘girls’. By the time I was half way home my eyes just wouldn't stay open any longer. I decided to pull over in a secluded wayside rest area. If I could just catch a little catnap I knew...Read On

14

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novaguy

Ready to Perform, Part Two – All Crossed Up

I get more than I bargained on!

Much happened in the next twelve months following that first session with my ex and her new partner: Ann began divorce proceedings which I didn’t contest, I financed myself into another home, and Ann, David and I met for two more sessions of torrid sex. These sessions were pretty much replays of the first; I would first screw Ann thoroughly through at least two climaxes, and then she would...Read On

67

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hummmph

A surprise ass-fucking in panties

A friend displays her kinkier side

A very curious thing happened to me the other day and I feel I need to share it with you... I have been 'mildly’ crossdressing for over a year now. I say 'mildly' because I am not into full feminization, I just love the feel and look of lace panties when they are hugging a good looking cock, not to mention the taboo. I have taken to wearing stockings too which feel amazing, it's like...Read On

44

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snowball

What a Girl Wants

'Katie' finally fulfills her fantasy of having sex with a man.

"Come on, Katie. Give in to your desires. You've gone this far. You're almost there. You're so close to your goals and dreams of being treated like a lady. Accept it. Embrace it. Give in and complete your journey. Tell me what you want." Todd and I had been friends for years and even co-workers at one point in our respective careers. It had been almost ten years since I'd seen him and it...Read On

10

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ThePhantom

My First Time - Part 3

The story continues...

As Lydia had promised, on the first day of her vacation I got my first lessons in high heels. It took most of the day before I was able to walk across the room and not fall on my face, and these were only a moderate heel. I took her to dinner to celebrate and, at her request, I wore the satin thong under my jeans. Lydia could not resist reaching out and squeezing the bulge in my jeans,...Read On

21

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torpedoman

July 4th Celebration

My wife Ann sets up a mini vacation over the 4th of July.

On July first I returned home from our health club. Ann was packing my suitcase for a mini vacation at a bayside resort. My suitcase was filled with all my girlie things: lubes, vibes, wrist and ankle restraints and the paddle she used on me when I was bad. She also said Ben, his brother Josh, and two others were joining us. Before continuing, I should mention how I became the man I am...Read On

7

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iluv2tosssalad

The Business Trip - Part 1

A man has a wild experience on an unexpected business trip.

I work for a small web design company in northern Connecticut. We acquired a rather large account with a lawn care company in Virginia, and my boss asked me to go with him to present the design we had created, since I was the only other male at the company. My boss told me he didn’t want any of the women to think he was hitting on them. Never having been asked to go on a business trip for...Read On

8

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vanessagrrl

Just the Two of Us, or Four

Vanessa and Greg fail at trying to spend a night alone

As time went on, the line was beginning to blur between me being Greg's girlfriend and Amber's pet. Greg decided that we needed a night alone. That didn't work out exactly as planned. He booked us into a lovely, fancy hotel in the heart of the city. Next up was going to be a nice dinner at a gourmet restaurant, and then we'd see where the night went from there. I wanted to impress, so I took...Read On

24

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libertina

Caught!

Crossdresser is caught by his flatmate and fuckec

I stood in front of my full length mirror wearing my new black heels. Not just the heels of course! I had a sexy, short black dress to go with them. Underneath, I had some incredible purple and black underwear; all silk and lace. I twisted on my heels and pulled my dress up a little, wiggling my thong covered ass at the mirror pretending somebody could see... ...And that’s when he knocked!...Read On

24

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xavier5269

Caught By My Girlfriend

Hitting puberty late in high school had its disadvantages. A slender, almost feminine body and a small dick was not something a lot of women tended to go for, however, I was lucky enough to find Adrian. We hit it off right away, shared many things in common and we couldn’t get enough of each other. She was gorgeous, standing at six feet, she was just as tall as me. Her beautiful crystal blue...Read On

21

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libertina

An Uneven Romance - Part Two

He's taken further into her strange, kinky world

“Hey, Sam.” I jumped and spun around, startled. One of my housemates, Mark, had walked into the kitchen where I was preparing breakfast for Sarah, the incredible girl I’d brought home the night before. Sarah was a pretty special girl; after a night spent with my head between her legs she had eventually let me cum this morning. She’d somehow coaxed me into wearing her wet panties from...Read On

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Crossdressing

Becoming John Collins' Mistress - Part One

Sexy Stewardess on a Hot Flight: Part One

Who Knew a Physical Could Be Fun

Adventures in a Woman’s Body – Chapter 2: Tease and Please

Meeting One of the Neighbors

Adventures in a Woman’s Body – Chapter 1: Plugging Up

Hitch-hiking Baby Doll: Part Three

Allen's Sweet Surprise - Part Two: The Yummy Conclusion

Just For The Taste Of It

Allen's Sweet Surprise Part One

Fucked in the Fitting Room Part Two: The Explosive Conclusion

Fucked in the Fitting Room Part One

My First Time Final Chapter

Steve the Crossdressing Cat Lover

My Boyfriend's Blue Silk Panties

First time sex with a man!

The Wedding Present

The Neighbour's Knickers - Part 1

After the Show

Keeping A Secret

Ready to Perform, Part Two – All Crossed Up

A surprise ass-fucking in panties

What a Girl Wants

My First Time - Part 3

July 4th Celebration

The Business Trip - Part 1

Just the Two of Us, or Four

Caught!

Caught By My Girlfriend

An Uneven Romance - Part Two