Crossdressing

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

trinitytowers

Felix becomes Felicity - Chapter 4

FELIX  becomes FELICITY Chapter 4 ..what a day I loved the tennis, Bradley was a pretty cool guy, but crikey what was happening! I only had something like 4 weeks left now so I was determined not to buckle under this, for my Mum and sisters sake. The next two weeks were quiet, I lounged around the house that suited me counting down the days. David continued to do our breakfast but...Read On

Added: 27 Jan 2010 | Category: Crossdressing | Avg Score: 4.75 | Words: 1,411 | Tags: | 2 Comments

KrissyS

Adventures of Kristof and Marci - Part 1

After a long internet relationship, Kristof and Marci finally get together to explore their fetishes

ADVENTURES OF KRISTOF AND MARCI PART I The Meeting I sat on the chair in front of the computer, wearing a tiny black swing skirt, black nylons and red high heels.   Beneath the skirt I wore a little pale pink lycra thong and I was naked from the waist up, save for the chain that hung at my chest, the ends connected to each nipple by a little clip.   ‘I really need to pee’...Read On

Added: 26 Jan 2010 | Category: Crossdressing | Avg Score: 4.75 | Words: 4,384 | Tags: crosdressing  spanking  watersports  fetish   | 3 Comments

JesseS

Crossdresser's Spanking Scene

The CD to CD variation of an erotic 'spanking leads to sex' scene, already posted.

My roommate and I were both bi and part-time cross-dressers. We were also familiar with consensual B & D and had already worked out several code words, then went a step further and wrote scenes for each other, so that when we're in the mood, we could call up the scene rather than try to explain it or coach someone through it.   Sometimes we did a scene to please each other sometimes we...Read On

Added: 25 Jan 2010 | Category: Crossdressing | Avg Score: 5 | Words: 1,372 | Tags: crossdresser  spanking  m-m  anal   | 2 Comments

trinitytowers

Felix becomes Felicity - Chaopter 3

FELIX  becomes FELICITY Chapter 3 ..He bent forward and thrust his large hands up my skirt on my thighs with his thumbs resting on the root of my penis, and put his face close to mine, “You had better be a good girl for everyone’s sakes sweetness. I know you love your Mum and Sister!” He slowly moved his hands up to my breasts and squeezed them hard looking into my eyes. I was...Read On

Added: 25 Jan 2010 | Category: Crossdressing | Avg Score: 4.71 | Words: 1,331 | Tags: | 1 Comment

trinitytowers

Felix becomes Felicity - Chapter 2

Life gets more girly for Felix!

FELIX  becomes FELICITY Chapter 2 My Mum and Sister went downstairs and I had a moment to myself looking in the mirror.  I didn’t recognise me in the reflection I saw a teenage girl, a very attractive teenage girl! I joined my Mum and sister downstairs. I was becoming better on the heels “Mum I have to reiterate that this all ends in 6 weeks time right?”, “Of course sweet that’s...Read On

Added: 23 Jan 2010 | Category: Crossdressing | Avg Score: 4.27 | Words: 2,359 | Tags: crossdressing breasts   | 5 Comments

trinitytowers

felix becomes felicity

bullied into becoming a girl!

FELIX  becomes FELICITY Chapter 1 “Gynecomastia is the abnormally large development of mammary glands in males, resulting in breast enlargement……… In teenage boys this does not have to be linked to obesity……… The word Gynecomastia  derives from the Greek for woman and breast”     I logged off from my regular searches on the internet and felt sick as usual. I am 16 and a normal...Read On

Added: 22 Jan 2010 | Category: Crossdressing | Avg Score: 4.4 | Words: 3,310 | Tags: schoolgirl  forced  breasts   | 7 Comments

starbelliedboy

Webmeets Diary Ch. 03

I become Sarah to meet an older couple.

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. I'd been using the swingers' site for more than a...Read On

Added: 09 Jan 2010 | Category: Crossdressing | Avg Score: 4.36 | Words: 2,812 | Tags: bisexual  crossdressing  sissy  mature  oral  anal  blowjob   | 2 Comments

Chrissy_CD_slut

Chrissy's First Black Cock

Chrissy gets fucked by a big black cock for the first time

  After I awoke from a deep slumber of a much needed nap, I laid there recounting memories from the night before with Todd. I got out of bed, walked to the kitchen and grabbed a soda from the fridge before sitting down on the sofa. As I sat down, a pain rippled through my ass, reminding me of the brutal fucking I had received from Todd. I sat there smoking a...Read On

Added: 17 Dec 2009 | Category: Crossdressing | Avg Score: 4.95 | Words: 5,433 | Tags: anal  interracial  oral sex     | 13 Comments

pornoperson

A Gift for Daddy

A CD Sub gives her owner a new toy...

"I brought you a present, Daddy," Stephanie said, giggling, as we stood on the porch in the run-down neighborhood in the industrial part of town. The man standing inside was in the shade inside of the house and I squinted to get a look at him. "Eyes down," Stephanie hissed, elbowing me. I did as she said and smiled inwardly. She was usually very submissive and proper when we were together and...Read On

Added: 08 Dec 2009 | Category: Crossdressing | Avg Score: 4.25 | Words: 2,100 | Tags: crossdressing  anal  bondage  fellatio     | 2 Comments

hardjake

Crossdresser and I at Costco

I went to Costco over the weekend with my friends girlfriend. She went off shopping, and I went off to get a few things. I walked down some random isle, and saw a girl leaning down. I snuck a peek at her butt and saw a little bit of a thong showing over the top of her shorts. She was wearing a blue hoody. I looked up and saw that she had really short brown hair. I tried to see her face, when...Read On

Added: 04 Dec 2009 | Category: Crossdressing | Avg Score: 4.3 | Words: 1,353 | Tags: crossdress handjob thong cum   | 3 Comments

cum_dump_boy

Cruising The Drive In

It was a Friday night and all of my friends were at home with family. I was really bored and I asked my dad if I could take the van and go to the movies. He said it was ok and told me to be home by midnight. The van was a 1977 Chevy van, it was brown in color and had the moon windows cut into the side. It had the typical "Captain' s chairs" up front and in the back had what you'd expect from...Read On

Added: 28 Nov 2009 | Category: Crossdressing | Avg Score: 4.86 | Words: 1,748 | Tags: | 13 Comments

philippasubmaid

Caught and the Consequences Part 4

Husband caught dressing and the wife's retribution continues

Part 4   I served dinner at 7.00pm as requested and I was made to stand by the table so that I could serve wine as their glasses were emptied and attend to them as requested. I did find the whole experience satisfying in a kind of way as I knew I was pleasing my Mistress and hopefully Sir as well, although neither of them had any conversation for me.   ...Read On

Added: 23 Nov 2009 | Category: Crossdressing | Avg Score: 4.28 | Words: 1,058 | Tags: crossdressing  female domination  bondage  cuckold   | 6 Comments

Candy_Gurl

Group Fun

Caught outside and forced to suck.

  This is a story of what happened a long time ago. I was 20 years old. I have always been a small guy, 5-5, maybe 125lbs on a good day. All the girls called me cute and I hated it. Until I tried on my girlfriends panties. Wow, I thought how girls were so lucky to wear all this sexy stuff. Well within a year I had gathered a couple of very slutty outfits. I loved Garters and stockings,...Read On

Added: 21 Nov 2009 | Category: Crossdressing | Avg Score: 4.06 | Words: 940 | Tags: gangbang  outside  forced  panties  heels   | 7 Comments