Crossdressing Stories

18

CourtneyFux

A Terrific Threesome: Part One

Wearing my girlfriend's panties leads to a big cock for both of us. .

When my girlfriend and I moved into our new apartment, the tall handsome maintenance man came by to put a hand-held spray-jet nozzle on our shower for us. I was home alone and dressed in a sexy little pair of Sherry's panties when he arrived and I put on her little short black silk robe to answer the door. When I opened the door, the maintenance man's eyes went directly down to my...Read On

7

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allfours

Carl, Carla and Hannah - Part 10

Hannah tells Carla about her night with Claire, and then takes her to a dogging spot...

Hannah took a different route than usual into town, and she surprised me by parking in an area we don't often go to. Once we'd left the car, we nipped into the Bullring and picked up the few things I needed. I was so nervous that I could hardly speak, but Hannah insisted that I did so. I imagined that everyone was staring at me, but after a while, I came to realise that most people didn't...Read On

37

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sluttracy99

My Sexual Odyssey Part 1 How I Got Started

This is the first in a series of stories that will cover my sexual experiences in chronological orde

I was always extremely sensuous, expressed in the love of the feel of satin and silk, as well as the feel of going barefoot, which was nearly impossible in the city, even indoors, not part of the culture. Where I live now it is, and so I go not only barefoot but also nude when at home. I don’t know if this is significant or not. However, the first time I noticed anything unusual was...Read On

8

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cheryl_lover

Christina and Cheryl - part 2

Christina and Cheryl venture in to the public

"Pedicure?!" I was alarmed. This had all been fun and very sexy, but a pedicure? That would mean I would be venturing in to the public, something I had previously barely even considered. Would I pass? Would I be ridiculed? Would I be verbally abused? Would I be physically abused? These were the things that crossed my mind at first. But then I considered a different scenario. Would I be...Read On

7

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allfours

Carl, Carla and Hannah - Part 9

Hannah meets Claire, while Carla keeps herself amused...

The rest of the week followed a similar pattern to the last couple of days. Get up, work, back home, then change into Clara and feminine training. The only difference was that on Thursday, when we got back home after the weekly shop, Hannah suggested I try speaking a little more like a woman. We looked on the net and found loads of helpful videos, hints and tips, so after that, I...Read On

22

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DaniCD

Nice surprise for the delivery man

Me and the delivery man get cosy

I'm a crossdresser in my early 20's and still live at home unfortunately. The day started as it usually does when I'm home alone, dressing up. On this day I had gone for a pink G-string with a matching bra, my breast forms, and some tight leggings which showed off my pert bum very nicely. A black lace top and of course my light brown shoulder-length wig and my make-up. I was in a bit of...Read On

6

vote

Cdashlynninsc

My wife takes what she needs and wants

Normally conservative wife suddenly decides what she is going to take what she needs

I'm a very lucky husband. I have an extremely sexy wife, who is open minded, and loves to please. If she has any faults, it's that she doesn't realize how sexy she is. At 37, she has extremely long red hair (which she jokingly calls stripper hair, but it's actually the truth because it's so sexy how long it is and how it falls against her backside), really fantastic legs, nice curves, lots...Read On

9

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allfours

Carl, Carla and Hannah - Part 8

Carla goes shopping and makes a realisation, while Hannah rekindles an old flame

As we drove to work the next morning, Hannah told me to meet her in reception at twelve so we could go shopping. Because the office ran a flexi-time approach to lunch hours, and provided the time was made up, staff were allowed to lunch between twelve and two. So, at one minute past twelve we met and headed out into town. The cool air round my legs felt different through the tights, but by now...Read On

Added: 28 Jan 2014 | Category: Crossdressing | Avg Score: 5 | Words: 3,021 | Tags: crossdressing feminization lesbian office work

1

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Heytherebaby

Becoming John Collins' Mistress - Part Two

I'm invited to spend a day with one of John's hunky friends

The next day, everyone was a bit hung over. I needed to pick up my car, which I’d left at the bar the night before. Joe said it was on his way and he’d be glad to take me. I borrowed a raincoat from John to wear over my skimpy outfit, then Joe and I headed out. Joe was making eyes at me during the drive, and I decided it would be best to come clean. “Joe, there’s something you...Read On

Added: 28 Jan 2014 | Category: Crossdressing | Avg Score: 3 | Words: 2,744 | Tags: crossdressing

12

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allfours

Carl, Carla and Hannah - Part 7

Claire starts work at the office as Carla continues her voyage of discovery into femininity...

I switched the six-thirty alarm off with a groan and turned to cuddle Hannah. After our customary two minute huddle, I kissed her and then wearily got out of bed. Without thinking, I sat down on the toilet and relieved my bladder, and then took off my bra and panties before stepping into the shower. The soothing warmth of the water managed to ease some of the ache in my body from the...Read On

13

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allfours

Carl, Carla and Hannah - Part 6

Carl becomes Carla...

By the time I awoke the next morning, it was already getting light. I'd not had the best night's sleep as my uncomfortable boobs kept waking me up everytime I lay on them. Now I needed to pee. I opened my eyes and looked at the alarm clock which read seven-fifteen. Then I looked across at Hannah. She looked adorable as she lay sleeping, so I slowly and carefully slipped out of bed so as not...Read On

8

vote

allfours

Carl, Carla and Hannah - Part 5

Carl takes on a bet...

We lay in each others arms for a while and then Hannah raised herself up and got off the bed. She unbuckled the strap-on cock attached to her. It was only as she took it off that I saw that this one was not only slightly bigger than the one she used earlier, it also had a dildo for her. No wonder she'd enjoyed that last fuck as much as she had. She passed it to me, telling me to take it to...Read On

11

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pentup47

Trio

A secret assignation in a country hotel turns into an unusual menage a trois

Dusk. As he turned off the highway into the country park hotel, Nick was relieved to note that its car park was barely a quarter full. Pulling his overnight bag from the back seat, he headed for the brightly-lit reception lobby. A giggly gang of women were disembarking from a mini-coach. Most were clearly very drunk. In the hotel's spacious lobby he quickly spotted Mark,...Read On

11

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allfours

Hannah, Carl and Carla - Part 4

Hannah explains herself.

When we got home, Hannah told me to take the bags upstairs to the bedroom and strip down to my lingerie. Once there, she started looking through the bags that she'd got while I was trying got undressed. In the first bag, there was a pair of black court shoes with a two-inch heel. She told me to try them on, which I did. Six hours ago I would have felt stupid and embarrassed to even...Read On

14

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allfours

Carl, Carla and Hannah - Part 3

Carl starts down the road of feminisation

Hannah released my hair and left me on my knees as I gasped for breath. My throat felt sore from the fucking she'd given it with her dildo, and my legs trembled beneath me. I hoped that I had done enough to satisfy her, but with the rest of the weekend still ahead I knew deep down that there would more ordeals to come. As she got back onto the bed, she told me to go and get her breakfast. As...Read On

4

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culotte_de_dentelle

Leigh and Leila - Fantasy of a First Night

CD Leila gets read for her first encounter with her girlfriend.

“I don’t know when to stop talking, do I?” I asked. You smiled and kissed me again. It took my breath away. I closed my eyes and let myself get lost in the feeling. It was like nothing I’d ever imagined, nothing I’d ever felt before, nothing I could imagine living without. Your fingers moved just the slightest bit. I nearly came, my cock straining hard against the white satin thong. Your...Read On

15

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cheryl_lover

Christina and Cheryl

Girlfriend makes me cross dress and fulfill her fantasies.

Christina and I had been dating for nearly two years. Within six months into our relationship, I confessed that I enjoyed dressing in women's clothing. She'd been more than accepting and encouraged me to indulge in this. She'd bought me bras, made me wear panties, painted my nails, and given me make overs. Seeing how horny it would make me turned her on even more so. I knew Christina was bi...Read On

16

vote

allfours

Carl, Carla and Hannah - Part 2

Hannah gets the upper hand.

I awoke to the sound of running water. Hannah was in the shower, leaving me alone in bed. A dull ache in my backside reminded me of what had happened last night: Hannah had tied me up, blindfolded me and then fucked me using a strap-on. She had called me a bitch and a slut as she held my legs over her shoulders and pounded me like a whore. And, apart from when she forced me to swallow my own...Read On

33

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allfours

Carl, Carla and Hannah - Part 1

Carl gets pegged by his girlfriend

It's funny the places life leads you to. Sometimes you think you know where you want to go, be who you want to be, and then from nowhere something or someone comes along and knocks you way off course. For example, if you'd have told me a year ago that on my wedding night I'd be on my knees being spit-roasted by two guys while dressed in my wife's wedding dress, I'd have said you were crazy....Read On

13

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bbra

Night on the Town

The girls and I go out to a lesbian bar.

Night on the Town Barbara Marsh “Well, come on, chicken!” I responded, “Cluck, cluck.” Okay, so I know it’s not original, but it was the best I could do. Despite my misgivings, I got out of the minivan, smoothed my skirt across my hips, and waited for Alexis. Her name’s really Alice, but she was Alexis for the night. The same way Jeanna was Gina and I was Betinna. I don’t...Read On

24

vote

SubGuy128

Oh, Daddy

Making of a cum slut

It all started with an online ad. I had always known I was different. I tried to pretend I liked girls, but I really wanted to be one. Let me describe myself. My name is Tony. I am 17. I'm 5' 10", 125 pounds. I have long blonde hair that girls are always jealous of, but it's always my blue eyes that draw everyone's attention. I was pretty shy and mostly kept to myself. I had a few friends,...Read On

12

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libertina

An Uneven Christmas

He is dressed up by a girl for his friend's entertainment.

By Christmas, Sarah and I had been ‘dating’ for a few weeks. If you could call it that. I had been spending a lot of my time with her, but I often felt more like a servant than her boyfriend. Most couples might curl up together to watch a film, I was more used to curling up at her feet. Worse, I was sure my friends realised there was something odd going on. Mark, who had the room next to...Read On

12

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HollyInPantyhose

Adventures in a Woman’s Body – Chapter 4: Public Humiliation

Used as a playtoy at the mall

I stepped out of the shower and began to dry myself with a towel. On this bright Monday morning, all I could think about was what happened on Friday night. After being gangbanged and cumed on thoroughly, Daddy drove me home that night. On our way there, he explained to me the situation that I am in. Daddy took out his phone and showed me pictures he had taken of me being a dirty little whore....Read On

28

vote

ericamalamute7

Shopping with the Boss's Daughter

I came home from work after a successful morning meeting where we finalized a big project. I decided to celebrate by going out to buy a new dress. I changed out of my business suit and grabbed a quick shower to shave smooth. I put on my make-up, choosing to go with a conservative look for the day with a pink lipstick. I got dressed with black panties and bra, and pulled on the silky nylons...Read On

10

vote

PantyWearingBJgiver

Being Slutty at a Panty Party

A hot CD gave me a sexy choiceI

I would love to tell you about my most recent adventure in my new life of wearing panties and sucking cock. I was invited to a panty party, and was so excited that I had just gotten all my stuff waxed just for this occasion. This was the first one and I was so excited. I took me awhile to pick out the right panties, but I settled on a hot little sequined thong. I made sure it could hold my...Read On

23

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CourtneyFux

Workouts with My P.E. Coach

Courtney has a crush on her P.E.coach, Coach Cocker.

My P.E.coach, Coach Cocker, was a tall, handsome man. More than once when I saw him blow into his whistle, I wished he was blowing me. I was a seventeen-year-old tranny-in-training and I loved having a big handsome man sucking my dickie for me. So, it was only natural that I would want Coach Cocker sexually. I already liked flirting with him like the girls did. And I thought he liked me, too. ...Read On

20

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Green_Man

A Real Lady

What's a real lady, anyway.

It doesn't matter to me in the least. I just love it. Sex, that is. I love it all. Well, I don't suck cock, and I don't take it up the ass, except from a beautiful woman, after I have screwed her ass hole, and every other hole she has. Turn about is fair play for the ladies. I don't play that game with the guys. She was a pretty little thing in a red dress. I was sitting at the bar. We...Read On

20

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HollyInPantyhose

Adventures in a Woman’s Body – Chapter 3: Used by Strangers

I become their powerless cumslut

I put his softening cock back into his pants as he parked the car. He got out and I crawled up after him. Having been on my knees for so long, my knees were aching and my legs were sore, but at least my feet got a rest from walking in my seven inch black stilettos. “What’s your name, by the way?” I asked him, since I don’t know what to call him by. “Just call me your Daddy, sugarslut.”...Read On

36

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Poppet

Can't I Have Them Both?

Can I Make This Work?

Waking up to the sound of my alarm blaring, I roll over and slam on it. Of course it doesn't go off, just crashes to the floor. I know I shouldn't have stayed up so late last night playing video games, but what can I say? Too late now, I suppose. I reach down to pick up the clock, seeing the time blinking at me. Getting out of bed, I grab the shower before anyone else can. I know what...Read On

13

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CourtneyFux

Two Cowboys and One Dancehall Girl: Part One

With the rodeo in town, Courtney looks for a cowboy to ride her.

I live in a town where the national rodeo cowboys come to town every year. And each time they come the testosterone level in town goes up, immensely. All of the big handsome, strong men in spurs and chaps and jeans and western-cut shirts and cowboy boots and cowboy hats get my clitty dick stirring down in my little panties when I see them around town in their pickup trucks or sitting tall in...Read On

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Crossdressing

A Terrific Threesome: Part One

Carl, Carla and Hannah - Part 10

My Sexual Odyssey Part 1 How I Got Started

Christina and Cheryl - part 2

Carl, Carla and Hannah - Part 9

Nice surprise for the delivery man

My wife takes what she needs and wants

Carl, Carla and Hannah - Part 8

Becoming John Collins' Mistress - Part Two

Carl, Carla and Hannah - Part 7

Carl, Carla and Hannah - Part 6

Carl, Carla and Hannah - Part 5

Trio

Hannah, Carl and Carla - Part 4

Carl, Carla and Hannah - Part 3

Leigh and Leila - Fantasy of a First Night

Christina and Cheryl

Carl, Carla and Hannah - Part 2

Carl, Carla and Hannah - Part 1

Night on the Town

Oh, Daddy

An Uneven Christmas

Adventures in a Woman’s Body – Chapter 4: Public Humiliation

Shopping with the Boss's Daughter

Being Slutty at a Panty Party

Workouts with My P.E. Coach

A Real Lady

Adventures in a Woman’s Body – Chapter 3: Used by Strangers

Can't I Have Them Both?

Two Cowboys and One Dancehall Girl: Part One