Crossdressing Stories

11

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

14

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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

11

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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

7

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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

10

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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

11

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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

14

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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

14

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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

13

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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

9

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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

8

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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

8

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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

4

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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

7

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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

15

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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

15

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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

14

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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

40

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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

10

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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

10

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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

30

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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

16

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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

14

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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

9

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philippasubmaid

Caught and the Consequences Part 3

Husband caught dressing and the wife's retribution continues

Part 3 I signed the contract and handed it back to my wife, well my Mistress now I guess. She took it from me and said ‘Good girl’ ‘As you will have seen you are now Philippa, now go and get all your male clothes.’ ‘Can I get dressed’ I said. She slapped me hard across the cheek. ‘When you speak it will...Read On

14

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pam1950

Lingerie and Domination

Lingerie Shopping and something more

I had answered an ad on telephone dating service. She described herself as a ‘bedroom dom’. I am not sure why I answered the ad and I did not really expect a reply. She phoned when I least expected. I did not think she would be interested but I had mentioned in my reply that I like to dress in lingerie — panties in particular. I met her for a drink. She was younger ( 38 ) than me and...Read On

34

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Chrissy_CD_slut

Chrissy's First Bookstore Trip

Chrissy's First trip to an Adult Bookstore Arcade

After my first night dressed up like a girl in my very own clothes I started to wear panties and thigh highs under my pants when I went to class or anywhere for that matter. I couldn't get over the sexy feeling of the panties on my cock and the nylons on my legs. By now I had purchased quite a few women's clothes. I had all different colors of matching bras and thongs, I loved the way the...Read On

10

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philippasubmaid

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

9

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philippasubmaid

Caught and the Consequences

Husband caught dressing and the wife's retribution

‘What the hell do you think you are’ I just lay there not knowing what to say and I am sure going very red under my make up. ……….. I will go back many years and start at an earlier age. For as long as I can remember I have cross dressed, always in private, without my partners or girlfriends knowing, totally in the closet,...Read On

25

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SashaCD_ThongPanties

My first halloween night as a teen CD!

My first time i dressed up like a chick and how lucky i got that whole night

This is halloween!! A day that everyone goes out and dresses up in costumes and other things, and go to parties and drink and show off their wild side until the wee hours of the next day. And I thought to myself, since everyone goes out and wears costumes, why not dress up myself into something wild and willy?? Or in fact, why not dress up in a manner of expressing who I am and what I...Read On

26

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Chrissy_CD_slut

My First Real Outfit

My First Real Outfit I started completely dressing in women’s clothes shortly after high school. I didn’t really own anything of my own but I would fully dress in my mothers clothes a few times when I knew she would be gone for a few hours.. Usually it was just pantyhose, bras, and panties that I would borrow from my mom . I had experimented with it a bit when younger, stealing my...Read On

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Crossdressing

A Nanny Femtastic - 6

A Nanny Femtastic - 5

A Nanny Femtatastic - 4

A Nanny Femtastic - 3

The Adventures of Kristof and Marci Part 2

A Nanny Femtastic -2

A Nanny Femtastic - Chapter 1

Felix becomes Felicity - Chapter 7

Felix becomes Felicity - Chapter 6

Felix becomes Felicity - Chapter 5

Felix becomes Felicity - Chapter 4

Adventures of Kristof and Marci - Part 1

Crossdresser's Spanking Scene

Felix becomes Felicity - Chaopter 3

Felix becomes Felicity - Chapter 2

felix becomes felicity

Webmeets Diary Ch. 03

Chrissy's First Black Cock

A Gift for Daddy

Crossdresser and I at Costco

Cruising The Drive In

Caught and the Consequences Part 4

Group Fun

Caught and the Consequences Part 3

Lingerie and Domination

Chrissy's First Bookstore Trip

Caught and the Consequences Part 2

Caught and the Consequences

My first halloween night as a teen CD!

My First Real Outfit