Crossdressing

purekink

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

Added: 11 Apr 2010 | Category: Crossdressing | Avg Score: 4.69 | Words: 1,637 | Tags: crossdressing  strapon  ffm   | 9 Comments

purekink

A Taste of my Girlfriend's Dildo

I'm caught - and made to love it.

I can’t think of anything I’d rather be doing than sneaking into my girlfriend’s wardrobe while she’s out and trying on her lingerie. The moment she leaves the house, I head for her garter belts, bras and knickers. I don’t have anything to put into her 36C bra cups, and my cock barely fits her panties but all that silk, satin and lace is irresistibly sissy and feminine. On the day...Read On

Added: 10 Apr 2010 | Category: Crossdressing | Avg Score: 4.93 | Words: 1,562 | Tags: crossdressing  strapon  fm   | 12 Comments

JesseS

This one is for Tracy

Submission of a crossdresser to his boyfriend's girlfriend.

This story requires a short preamble. I had e-mailed erotic stories and fantasies back and forth with my friend Paul for several months. He liked to be a dominant, so one day I asked him to send me exacting instructions on how he would like me to masturbate, which I would have to do and then describe back to him. He sent the instructions, which involved me getting fully cross-dressed...Read On

Added: 28 Mar 2010 | Category: Crossdressing | Avg Score: 4.89 | Words: 1,277 | Tags: fmm  cd  tv  anal  bi  fem-dom   | 7 Comments

trinitytowers

The Feminisation of Michael. - Chapter 7

The Feminisation of Michael. Chapter 7 I settled in at Stanmore House quickly and Sam helped a lot and we would spend most days together with her showing me around the estate. I soon persuaded Sam to wear prettier things and we were often seen., me blonde, her brunette, rushing around giggling in little floral dresses. Alternatively we would ride the beautiful horses in...Read On

Added: 24 Mar 2010 | Category: Crossdressing | Avg Score: 4.91 | Words: 2,001 | Tags: | 8 Comments

Driver1963

An Old Friend

Found out by a friend - hope the length is not a turn off...

   Jerri is a close friend whom I have known for a long time. I was on an interview board for her when she joined the volunteer fire department. I was a little skeptical about her joining, especially since her husband seemed to be rather indifferent about it, but was overridden by the rest of the board. As time went on, she proved herself to be one of the top responders and an...Read On

Added: 16 Mar 2010 | Category: Crossdressing | Avg Score: 4.38 | Words: 2,915 | Tags: crossdressing  friends  work  affair   | 11 Comments

trinitytowers

The Feminisation of Michael. - Chapter 6

The Feminisation of Michael. Chapter 6 The taxi dropped me off at a top hotel in London.  I checked in as Miss Michaela Wilson. My new name! I had credit cards and bank account details sorted out when I was in hospital so had a purse full of plastic! A bit like I now had a bra full as well! After the porter had left me alone in my suite of rooms I just collapsed onto my bed. ...Read On

Added: 16 Mar 2010 | Category: Crossdressing | Avg Score: 4.73 | Words: 1,894 | Tags: | 3 Comments

trinitytowers

The Feminisation of Michael. - Chapter 5

The Feminisation of Michael. Chapter 5 I found out later that I had been in a coma for two months.  I was unrecognisable and unconscious but still just alive. I remember waking up and being totally lost and I didn’t feel like me. Sue was there when I woke and the memory of her face returned as did the events of the run up to that fateful night. When I first woke, I couldn’t...Read On

Added: 11 Mar 2010 | Category: Crossdressing | Avg Score: 4.82 | Words: 1,386 | Tags: | 6 Comments

trinitytowers

The Feminisation of Michael. - Chapter 4

The Feminisation of Michael. Chapter 4 Sue had replenished my wardrobe again with new work clothes and had taken the secretary theme to heart! The skirt suits had been replaced with pencil skirts and pencil dresses. The blouses had been supplemented further with lace and ruffle fronted blouses. There were also several ribbed tight fitting cardigans in black, red and various...Read On

Added: 10 Mar 2010 | Category: Crossdressing | Avg Score: 4.93 | Words: 2,101 | Tags: | 5 Comments

sweetriyacd

Losing my virginity

Sometimes you just have to give in

I'm a 21 year old attractive crossdresser from Mumbai, India. I am sharing a true story of how my roommate turned into a permanent fuck buddy! I've been crossdressing for 10 yrs now and have my own collection of all kinds of stuff you can think of. I moved into the city 2 years back and rented an apartment with a guy called Vishal who I didn't know at the time.  The first few days...Read On

Added: 03 Mar 2010 | Category: Crossdressing | Avg Score: 4.47 | Words: 1,326 | Tags: crossdressing  virginity   | 9 Comments

pornoperson

An Afternoon with Suzie C*cksucker

A Mistress directs a scene with two sissies

One of the strangest relationships I've had over the years was with awoman named Laura. She saw my profile on Yahoo and dropped me a note. It was like manna from heaven. She was very into the idea of fucking a man in the ass with a strap-on dildo. She'd not done it before but had fantasized about it for years. Would I be willing to help? You bet! We chatted for a long time before we...Read On

Added: 03 Mar 2010 | Category: Crossdressing | Avg Score: 4.09 | Words: 862 | Tags: anal  crossdressing  oral  fellatio   | 1 Comment

jules86

Chelsea's New Slut

Chelsea makes me her new slut and begins to train me.

            I was wondering why Chelsea wanted to go swimming with me that day.   She had never shown interest in hanging out with me before, but I figured why not go for a swim with friends.   I thought she was way out of my league; she was 5’ 9’’ with beautiful straight black hair and huge double d breasts.   I was just 5’3’’ and a science nerd.   I mean she said it was just between the two...Read On

Added: 21 Feb 2010 | Category: Crossdressing | Avg Score: 4.63 | Words: 1,995 | Tags: swimsuit  strapon  mistress   | 6 Comments

trinitytowers

A Nanny Femtastic! - Chapter 11

A NANNY FEMTASTIC! Chapter 11 We walked to the harbour and found the boat. There were too bulky security guards checking people as they entered. The boat was in fact a massive cruiser! We joined the queue, it was obviously not a little gathering. The other women were dressed in classy whites and float summer dresses, we looked like too cheap hookers! “Trinity this was a...Read On

Added: 18 Feb 2010 | Category: Crossdressing | Avg Score: 4.85 | Words: 1,638 | Tags: | 4 Comments

trinitytowers

The Feminisation of Michael - Chapter 3

The Feminisation of Michael. Chapter 3 I endured the rest of the afternoon with continued suppressed sniggers and laughter. I was glad when 5.00pm came and I buttoned up my jacket and put my handbag over my shoulder and left with a big sigh of relief. Sue was waiting outside in the car. “Hi Michaela,” she greeted me. “How did it go honey?” she beamed. “Fucking awful!” I blurted out....Read On

Added: 17 Feb 2010 | Category: Crossdressing | Avg Score: 4.83 | Words: 2,202 | Tags: | 4 Comments

trinitytowers

A Nanny Femtastic - 10

A NANNY FEMTASTIC! Chapter 10 I rose early the next day and put on my white lace bikini, and took a dip in the pool. I was sitting on a lounger drying myself when Felicity came out. “Good morning gorgeous!” she said kissing me on the cheek. Our breasts rubbed together. “You know we have that party with those guys today sweetie?” “Are you sure we should go Felicity?” I said...Read On

Added: 16 Feb 2010 | Category: Crossdressing | Avg Score: 4.83 | Words: 1,397 | Tags:

trinitytowers

A Nanny FEmtastic - 9

A NANNY FEMTASTIC! Chapter 9 Thomas quickly pulled his hand from under my skirts, and stood up abruptly. “Fucking hell I don’t believe it!” he blurted out. Felicity was suddenly by my side. “What’s wrong?” she said. “forget it!” Thomas said, and stormed back inside, knocking over the table and drinks as he went. Bradley chased after him. I burst into tears and Felicity put her...Read On

Added: 12 Feb 2010 | Category: Crossdressing | Avg Score: 4.86 | Words: 1,447 | Tags:

trinitytowers

The Feminization of Michael - 2

The Feminization of Michael. Chapter 2 I continued with the “weekend” clothes for another few weeks and consistently had people commenting, laughing and making things difficult when I was out shopping. I continued at work in the more feminine suits and blouses too.  The rumours increased and somehow word had got around that at the weekend I wore dresses and full make up! This couldn’t...Read On

Added: 11 Feb 2010 | Category: Crossdressing | Avg Score: 4.83 | Words: 1,144 | Tags: | 4 Comments

trinitytowers

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

Added: 09 Feb 2010 | Category: Crossdressing | Avg Score: 4.92 | Words: 3,237 | Tags: | 6 Comments

trinitytowers

A Nanny Femtastic - 8

A Nanny Femtastic Chapter 8 When we got back to the villa I needed some time alone and left Thomas with Bradley and Felicity. We were all to meet for dinner that evening on the terrace. I had a few hours to myself and ran a big deep, bubbly bath. I had got used to pampering myself with an array of oils and scents. This and of course the regular hormone injections had softened my skin...Read On

Added: 08 Feb 2010 | Category: Crossdressing | Avg Score: 4.64 | Words: 1,487 | Tags:

starbelliedboy

Webmeets Diary Ch. 04

Celebrating the end of university as a slutty schoolgirl.

Note to the reader: In this diary I will tell the true stories of my sexual encounters that have come about thanks to the internet. Some more precise details such as names and places will be left out to protect mine and others privacy, and also because they don't matter, but otherwise I will try to be as accurate and truthful as possible. As I neared the end of my university course I had...Read On

Added: 08 Feb 2010 | Category: Crossdressing | Avg Score: 4.86 | Words: 3,281 | Tags: crossdress  gay  69  blowjob  anal  schoolgirl   | 3 Comments

trinitytowers

A Nanny Femtastic - 7

A NANNY FEMTASTIC! Chapter 7 After that first dinner Bradley and Felicity retired to their bedroom. And even though they were in a separate wing of the sprawling villa I could hear them making love! I thought of what Felicity felt as a transsexual woman having had a vagina created out of what was her penis. To feel Bradley rigid penis inside her. I wondered how nice it would be to put on...Read On

Added: 07 Feb 2010 | Category: Crossdressing | Avg Score: 4.69 | Words: 936 | Tags: | 2 Comments

trinitytowers

A Nanny Femtastic - 6

A Nanny Femtastic Chapter 6 ......... felt incredibly empowered, with women and Men coming onto me! I was loving being between the two sexes but presenting as a glamorous female. Alex was very dominant and bought me drinks and acted in the male role very much that night. Lou and her slept together generally, but there was no issue with Alex coming onto me. Later in the evening...Read On

Added: 05 Feb 2010 | Category: Crossdressing | Avg Score: 4.73 | Words: 735 | Tags: | 1 Comment

trinitytowers

A Nanny Femtastic - 5

A NANNY FEMTASTIC! Chapter 5 ... I looked gorgeous now with my ample breasts and thin waist! I would really enjoy this upcoming holiday! The electrolysis treatments had continued, and I now was pretty hairless and did not need to shave or wax. I did however remove all my pubic hair and became obsessed with having a completely hairless body. This included around my scrotum...Read On

Added: 04 Feb 2010 | Category: Crossdressing | Avg Score: 4.79 | Words: 962 | Tags: | 1 Comment

trinitytowers

A Nanny Femtatastic - 4

 NANNY FEMTASTIC! Chapter 4 ….I was aware I may be called upon by one of the girls in the night so would have to stay in bra and panties. I also had to ensure I shaved thoroughly early in the morning and hid away my razor and foam! I woke very early the next morning, thankfully no calls in the night! I shaved everywhere and slipped into a fresh bra and knickers, ensuring my...Read On

Added: 03 Feb 2010 | Category: Crossdressing | Avg Score: 4.64 | Words: 1,153 | Tags: | 4 Comments

trinitytowers

A Nanny Femtastic - 3

A NANNY FEMTASTIC! Chapter 3 ..That night me and the girls celebrated, I was about to start work at last next week! Ok as a woman but I kind of liked the idea more and more! The weekend passed quickly and I packed all my new wardrobe into a couple of large suitcases ready for the new start at  Hanover House. I was to be dropped off on Sunday evening and was to have dinner...Read On

Added: 02 Feb 2010 | Category: Crossdressing | Avg Score: 4.57 | Words: 1,328 | Tags: | 2 Comments

KrissyS

The Adventures of Kristof and Marci Part 2

Marci continues Krissy's slut training, putting her maid into some uncomfortable situations...

ADVENTURES OF KRISTOF AND MARCI PART 2 Training     As I stood outside the study, my mind was racing, the day had been pretty exciting already and it was only mid afternoon; what else was to come I wondered with excitement.   After a few minutes, Marci came down and entered the study and I followed.   ‘I told you to wait outside; you come in when I...Read On

Added: 02 Feb 2010 | Category: Crossdressing | Avg Score: 4.4 | Words: 3,848 | Tags: crossdressing  slut training  spanking  watersports  peeing   | 4 Comments

trinitytowers

A Nanny Femtastic -2

A NANNY FEMTASTIC! Chapter 2 …I just couldn’t work out what was happening. I loved dressing in girl clothes, I felt relaxed and unstressed. But where was this leading! How could this work? I had never seen my parents that regularly maybe twice a year and they had mentioned on the telephone about meeting a few times. I put it off due mainly to my eyebrows!  But I couldn’t put them...Read On

Added: 01 Feb 2010 | Category: Crossdressing | Avg Score: 4.73 | Words: 1,977 | Tags: | 1 Comment

trinitytowers

A Nanny Femtastic - Chapter 1

A NANNY  FEMTASTIC! Chapter 1 My story starts during a very bleak time in my life where I was unable to find continuous work of any meaningful type. I had, I suppose, looking back now, rather stupidly pursued Child and Nursery Care as a further education route. Much to my parents consternation!  Yes I was the only guy in the college but I thought I would soon move into...Read On

Added: 31 Jan 2010 | Category: Crossdressing | Avg Score: 4.53 | Words: 1,954 | Tags: | 2 Comments

trinitytowers

Felix becomes Felicity - Chapter 7

FELIX  becomes FELICITY Chapter 7 …We both fell asleep almost immediately. I got up whilst he was still asleep in the morning and put on his shirt loosely over my naked body. I woke him up with breakfast , we kissed and he left late morning.  I had been lucky to escape him not discovering my penis! I had to think hard about what to do about this. I would just have to have to tell him...Read On

Added: 30 Jan 2010 | Category: Crossdressing | Avg Score: 4.86 | Words: 688 | Tags: | 4 Comments

trinitytowers

Felix becomes Felicity - Chapter 6

FELIX  becomes FELICITY Chapter 6 ..I put the gingham dress on that fit well and completed the ensemble with the shoes and cardigan. I looked like a fully grown woman in a school girl outfit. My breasts seemed to project and fill the dress with the buttons on the front tight. The fabric belt pinched in my already slim waste and the skirt part of the dress flared slightly emphasizing my...Read On

Added: 29 Jan 2010 | Category: Crossdressing | Avg Score: 4.85 | Words: 2,196 | Tags: | 5 Comments

trinitytowers

Felix becomes Felicity - Chapter 5

FELIX  becomes FELICITY Chapter 5 ..My Mum and David had announced their impending marriage with a ceremony planned in about 6 weeks time. No guessing who was to be bridesmaids. The week before we were due to start back to school Jasmine mentioned at breakfast that Thomas wanted to take her to the cinema that night and that they had talked about a foursome me with Bradley .  “Not...Read On

Added: 28 Jan 2010 | Category: Crossdressing | Avg Score: 4.89 | Words: 1,623 | Tags: | 1 Comment