Crossdressing Stories

14

Rachelcd

My First Cock

My cousin's Suprise for me

I am now Staying with my cousin after my previous story so I can dress up as much as I like. my Birthday was coming up soon and my cousin said she would have a celebration all weekend for me as it was during the week she said this would be my entrance into womanhood. It finally arrived this weekend I thought would be the best I just showered shaved what body hair I had off then left...Read On

27

vote

Cdashlynninsc

Two girlfriends stay in for the night

Wife pleases her girlfriend then tells her whats going to happen next

The other day I came home from work and was looking forward to spending the evening with my wife. We had the next day off, and it was going to be great to just get some time with her. After I was home and settled my wife Dawn came and found me and told me she wanted to spend the evening with a girlfriend and have some fun. I was a little disappointed, but a few seconds later, she told me...Read On

12

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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

29

vote

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

29

vote

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

11

vote

LarsKaiden

Tennis

A panty sniffer is tamed

Sandra and I had been going out together for about six months. She was the perfect looking girl for me, with her beautiful freckled face, slim turned-up nose, pouty red lips, light green eyes, long blonde hair that she usually kept in a ponytail or braids, a great body topped with perky B-cup tits, and a cute firm ass that just screamed to be pumped. She was only 23, but Sandra already knew...Read On

37

vote

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

17

vote

CourtneyFux

Mom's Old Boyfriend: Part One

Courtney seduces her mom's old boyfriend and sleeps with him, all weekend..

It happened quite by chance and we managed to keep it a secret, ever since. I was home alone on a Friday evening wearing my mom's favorite black lace lingerie and her old boyfriend, Ron, came by to see her. He still had a key from when he was seeing my mom and he walked in without knocking on the door, startling me. And he caught me playing with myself through the sexy little black lace...Read On

15

vote

ChelseyR

In Wonderland, Pt.1

Costume mandatory...

When I was in high school I was always very camp, which was probably why almost all of my friends were girls. This was definitely why I first ended up crossdressing. I was sixteen and round one of my 'girlfriends' house for a few drinks on Halloween before we went to a house party nearby. I never much cared for Halloween, so just came as myself. When I came in they all sighed since I wasn't in...Read On

38

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PlayfulAshley

TV Repair Man

DISCLAIMER: Story is merely fantasy and completely fictional. So please do not believe this happened to me or ask me questions about it, thinking it is true. I am writing from the first person perspective simply because it is a fantasy and it’s just more fun that way;) About a month ago my TV broke and it is kinda big and expensive, so I decided to have it fixed rather than buy a new one....Read On

20

vote

Amatramp

Caribean Vacation part 2

Lost luggage leads to wearing girlfriend's panties as a swim suit and more

We strolled down the hall to the elevator. I did not notice what floor we went to, as I was so pre-occupied examining my sexy self in the reflective surface of the elevator. We got off the elevator and walked down the hall to a door marked 469. “This isn’t the dining room,” I objected. “No, this isn’t,” she replied as she knocked on the door. “Who’s room is this.” I asked. Before...Read On

17

vote

purekink

Becky's Video

I watch a movie that surprises me in more ways than one.

I suppose I was the one that first mentioned porn to Nikki. We'd been chatting on a girls' night out and laughed abut how I'd never found any porn in the house. She giggled and said I was bound to find some sooner or later – all men had some, somewhere. A few days later, I'd completely forgotten our drunken conversation and so when Nikki showed up at mine after you'd gone out with...Read On

6

vote

luvinia

birthday gift

gift given to a cd by his/her boyfreind

hi to all my readers and freinds today i m going to tell u about my meeting with my boyfreind i was sleeping in my baby pink color nghtie it was early morning i felt that someone was at the door. i quickly woke up and somehow managed to change in to my shorts and vest striping my nightie i was wearing pantie inside my shorts and rushed to the door when i opened it i was surprised to...Read On

Added: 31 Aug 2008 | Category: Crossdressing | Avg Score: 3.67 | Words: 988 | Tags: crossdressing skirts anal and oral sex love

14

vote

Bunny12

Sissy Slut Gets All His Holes Filled

Desperate sissy slut boy gets what he wants.

He was waiting for me as instructed, dressed in the bag of clothes I had left for him earlier in the week. I entered the motel room to find him sitting on the bed in the mini skirt, sheer blouse, lace topped thigh high stockings and stiletto heels from his goodie bag. With his legs crossed, he appeared to be quite demure but I knew the desperate, horny slut that was raging beneath the...Read On

9

vote

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

35

vote

Karin

Old Friend, New Relationship-Part 1

As it turns out, I confided my crossdressing desires in just the right person

Old Friend, New Relationship-Part 1 I met Karen in my divorce support group while I was dealing with my second divorce and she was trying to cope with her first. About the only thing that we had in common was that both our spouses had cheated with good friends of ours. She was a couple years older and very attractive. I remember that she always dressed so well for our group meetings. We...Read On

19

vote

pantyslut

My Parents Friend

Get's Me Hot Every Time I think About It

The year was 1987 and I was home on leave from the military. One particular Saturday night my parents were haveing a get together with some friends so I decided to go out and try and find someone to have fun with. I couldn't decide what to wear until I just decided on what I thought would make me look sexy. I grab my things and head into the bathroom and put on my sexiest black...Read On

17

vote

LingerieBoy

Been A Long Time

Once I got married I pretty much gave up my crossdressing lifestyle to lead a more "normal" life.You know,settle down,have a couple of kids. I was a happily married man with two kids,what could be missing? Well one day while at work,I was on the internet and stumbled onto a crossdressing website,and all kinds of memories came rushing back to me. The feeling of sexy panties,bras...Read On

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1ball

Mistress Hannah's Pathetic Husband Part 3

I learn how manly my mistress wife can be

The first week of having a useful cock went well. For the first time since we got married, we had sex every night. After strapping my extension on, I would lick Hannah's pussy enough to get her turned on and then she'd choose a position. If I got physically worn out, she would choose another position. Because I was having sex so often and doing some research on the Internet, I was able to...Read On

Added: 20 Oct 2011 | Category: Crossdressing | Words: 3,357 | Tags: humiliation feminization strapon anal | 3 Comments

27

vote

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

21

vote

TaraNicole

Smooth Sensation

A t-girl get what she wants......

God I was glad to be home, a two-hour train nightmare. Every stop from Liverpool Street London on the 6pm slow train to the dreary little Essex village that was the only place I could afford to rent a studio flat. My only consolation was the bag of goodies I brought in my lunchtime and the anticipation that tomorrow was Friday and my big night in with my mysterious blind date. I had...Read On

14

vote

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

24

vote

SosaGood

My Mother's Boyfriend, My Slut

He seemed like a slut to begin with, who knew he really was.

Divorce often times traumatizes the children, but in my case, it set me free from all their arguments. Dad signed the papers and walked out the door on my seventeenth birthday; it was the best present he could have ever given me. I was finally free, I could go to parties and hang with guys. Mom was the lenient one who was always gone on some major trip. I was cool with it until she brought...Read On

31

vote

cassandrababy

Confessions of a Sex Crazy Cross Dresser

The first two chapters of my first novel

The Confessions of a Sex-Crazy Cross Dresser Book I: The incredible first few weeks Chapter 1: Panties Thief and the Late Night Swim My name is Sandy. My name is Tony. I know it sounds confusing, but when you are a cross dresser life is always confusing. Just the terminology alone to describe you…crossdresser or cross dresser? Transvestite, tranny, she-male and many other names used...Read On

12

vote

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

16

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Toby

My first Cross Dresser and me

My first cross dressing experience

I laid down beside her and gave her the soda. We sipped slowly and talked about what had just happened. I sat the sodas on the night stand and moved up closer to Toni (a name we will use for this article) crossing my leg over hers so that my clitty rested on her nylons. We kissed for several minutes as I played with her nipples thru the silky bra. Toni looked up with lust in her eyes and said...Read On

31

vote

libertina

A Whole New Me - Part 1

Borrowed panties and a day with my friend reveal a whole new side to me!

“Honey! Are you around?” I shouted from my room, rummaging through my drawers and naked from the shower. “What’s up, sweetie?” My girlfriend, Lisa, popped her head around the bedroom door. Her eyes taking in my body and a cheeky smile forming on her pretty face “Oh, looking good.” I wasn’t the most muscular guy but I wasn’t fat at all and Lisa always claimed she liked my body not being...Read On

26

vote

rushman1uk

The feeding of sissy

I hold a prominent position in a world wide business firm and make a six figure salary and had been divorced for several years. I met Wendy through a newspaper add in the singles columns, she was a knockout looking gal. We dated for some time and she moved in with me. One night when we were out having drinks she ask what my deepest secrets were. She would share hers with me in return if I...Read On

19

vote

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

21

vote

duke1933

Halloween

Boys will be boys

This story is not to be copied or moved to another web site Well here it is Halloween and I have an idea to dress up with my older bro and take the two younger bros out to trick or treat. When the big night came I got some of my sisters things to dress up in. I took all I needed to look just like her with the panties bra and skirt and blouse with a short jacket over it all. I must say...Read On

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Popular Tags

Crossdressing

My First Cock

Two girlfriends stay in for the night

The Feminisation of Michael - Chapter 3

Chelsea's New Slut

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

Tennis

My Boyfriend's Blue Silk Panties

Mom's Old Boyfriend: Part One

In Wonderland, Pt.1

TV Repair Man

Caribean Vacation part 2

Becky's Video

birthday gift

Sissy Slut Gets All His Holes Filled

Caught and the Consequences Part 3

Old Friend, New Relationship-Part 1

My Parents Friend

Been A Long Time

Mistress Hannah's Pathetic Husband Part 3

My First Real Outfit

Smooth Sensation

Lingerie and Domination

My Mother's Boyfriend, My Slut

Confessions of a Sex Crazy Cross Dresser

An Uneven Christmas

My first Cross Dresser and me

A Whole New Me - Part 1

The feeding of sissy

Caught and the Consequences Part 4

Halloween