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Crossdressing

Our crossdressing (cross-dressing) stories feature tales of either gender (usually male) dressing up in the clothes of the opposite sex, for reasons of sexual gratification. Crossdressers are akin to the transvestic fetishism, which is a sexual fetish for the clothing of the opposite gender. The crossdresser can be of any sexual orientation.

8

Aunt and Uncle Sex Slave

It was the summer of '82 and mom and dad were going through an awful divorce. They decided that it would be best that I stay with some good friends of theirs, Charles and Betty, while they got through this difficult time. They were an older couple, both were around sixty at the time. By this time I was a fully fledged cross dresser and no one knew of my secret except a neighbor. I had all of...Read On

4

Crossdresser in Love

A closeted crossdresser finds love with man

I woke up with my hands bound, my mouth gagged, and my ass plugged. The bed I was on was comfortable enough. This was just a reminder that these parts of my body were no longer mine to do with as I pleased. For tonight would be my wedding night. For months we had planned things out. Picking out a dress, a place for the ceremony, all the things that brides do with their future husbands. But...Read On

8

Losing at Strip Poker with Three Women

Oh my god, what did i get into?

Well, last night was quite a night to say the least. Three girl/friends came by with wine coolers and tequila to do a little partying. The four of us have been very tight for over fifteen years. We are very special friends that can talk about anything to each other. I should have known they were up to something when they said the tequila was all mine and the coolers theirs. They know I...Read On

13

Born to Be a Babe

Sexy girly boy ponders the allurement of lingerie.

I don't know why I started wanting to be a girl. But I do know when it started. I was sixteen when I first started looking at photos of sexy models wearing lingerie in Cosmo . These beautiful, statuesque women wearing the sexiest clothes I'd ever seen turned me on so much. In fact, I was more turned on by looking at these women in lingerie than I was looking at the naked women in...Read On

6

The Sexy Ball Girl

Being a sexy ball girl for her boyfriend's baseball team gets Courtney very horny.

When I was twenty years old and going to college, I had a steady boyfriend who treated me just like a girlfriend at all times. He opened car doors for me and he always paid when we went on dates. He was very sweet to me, making me feel feminine like a girl. He also liked having lots of sex with me in public places like the beach and parks and movie theaters, so we had an exciting, fun...Read On

8

Bookstore Bunny Gang Bang

Dressing as a Playboy bunny at the bookstore lands Courtney four big cocks.

Dressing as a sexy girl is my favorite way to meet men and have fun. There are so many different sexy outfits a girl can wear to attract men and turn them on, they ensure it never gets boring for a man. Every girl wants to be her sexiest when wearing lingerie and I am no different. Recently, I was on a business trip which included spending the night in a motel located across the street from...Read On

24

Hot Fuzz

Caught by a cop

If you have read my profile you would know that I am married with three kids, and no privacy. That being said, I try to indulge in my favorite pastime of cross dressing whenever and wherever I can. I was working as a manager for a convenience store where I would have to get up early in the morning to open the store. It was a 24 hour store, so I just had to get there to send the graveyard...Read On

4

Adventures in a Woman’s Body – Chapter 5: Secretarial Duties

Serving some very important people as the secretary

John waited for me to finish eating my cum burger, and then he told me to get up because we were leaving. I stood back up onto my six inch stilettos and walked with his arm around me, which firmly grabbed my ass. We exited the food court and made our way to his office building. The mall had a vast underground network so we were able to walk to his workplace without going outdoors. Along the...Read On

34

A Little Naughty Fun When My Wife Is Away

A little wicked fun

When I was in high school, I always loved to dress in women’s clothes. The problem is I'm a guy. Whenever my mother was out, I'd always go into her room and try on her intimate apparel. I just loved how it felt on my skin. I'd especially liked how her bras and panties felt. I loved to get dressed in her dresses and even apply make-up. I really never told anybody about this. The lacier...Read On

9

Jason and Kym ~ Part Two

A story about self-discovery, now turns into a rollercoaster ride!

 Later that same night, I strolled down to my favorite watering hole to tip a few strong drinks in the hopes of either clearing my head or dulling the noises within. After flirting over those drinks with a short blonde haired gal named Kym, we stepped out onto the dance floor to press our bodies against one another to an old Jonny Cash tune. She’d been waiting for some guy to meet her for...Read On

7

A Lifelong Love Of Lingerie

An introduction to a lifelong love affair with women's clothes

At the time I was sixteen, my mother was divorced and living with me, and she still worked and was gone until late in the afternoon on some days, so I would have the house to myself. I did not have access to porn until later, but there was Cosmopolitan magazine and other magazines which had the sorts of ads and stories that intrigued me, underwear ads, tampon ads - they all did the trick. I...Read On

12

Rose Otto

Man is the only creature who refuses to be himself...

"Ah, ah, ah..." cried Brenda ecstatically, hoping that tonight, of all nights, might be different. She was completely naked, her 38c natural tits swaying with the rapid thrusts, her thick hairy legs locked around Doug's firm arse, her hands clasping him as if to keep him in place. Brenda's husband Doug was fucking her passionately, he had fingered her to climax prior to climbing on top of...Read On

8

Learning To Be Submissive - Part 2

My second meeting with Jack

I arrived slightly earlier than I was meant to. After our first meeting I had been given specific instructions. Jack had allowed me to shower and change back into my normal clothes. Once I had returned to the kitchen, I found a note with a key. "Today you excelled yourself, but you have more to learn. Next week on Monday you are to come directly here after you finish for the day. I will...Read On

13

What I Do When I'm Alone

The fun I have when I am alone.

With the wife off to work today, I decide to indulge in my fetish. I wait a little bit till I know she is at work and it's upstairs I go. I take my computer with me to chat with friends and others I happen to meet in chat rooms. I lie down on my bed and start chatting with people and seeing which friends are on. It takes about an hour before I finally find someone to chat with. What follows...Read On

3

Night at the Video Store, part 3

bimbo crossdresser cruises video store in Black part of town

There I was a sissy bimbo dressed like a slut in a short black micro mini skirt, spike heels, lots of junk jewelry, huge platinum blonde wig, shoulder strap white fur purse and, of course, perfect make up. I had never been to this video theatre before and was nervous at first, but I waited for my eyes to adjust to the darkness and then moved into the theatre area. Screen five was recommended...Read On

12

I am Sissy

a fantasy of a taken slave by a pirate captain

The year was 1888. My name was Sebastian but I was now called Sissy since I was taken a slave. My father’s merchant ship was captured and sunk by the pirate crew of the Black Bess. I alone was saved for Captain Booth's pleasure. He was an escaped convict from the prison island of Australia. He was a huge beast of a black man, dark ebony skin stretched tight over enormous muscles that...Read On

20

Learning to be submissive - part 1

A gift comes at a cost

Before the days of internet chat rooms and social media I was very lonely as a young cross dresser. I can't speak for everyone of course but I would use telephone messaging services to talk to like minded people. I had received my first mobile phone for a recent birthday and I would often call up to chat to people. Sometimes things would turn into phone sex and on the rare occasion I would...Read On

11

Memories

Reminiscing about time spent before dating

Just for fun, I though it might be nice to share some of the experiences I went through on my way to becoming the sexy slut I am. Before I had the confidence to fully dress and go out, and to go on the few dates I've been on, I was completely closeted. The only way I could express my girly side was through playing on the phone and all alone. I loved dressing up a few times a week. I...Read On

10

Queen of all Hearts

College Queen finds the King!

Justin sprawled himself on the sofa, dressed in his pretty frock. He flicked through the TV channels, feeling rather content. Justin was always different, even as a child, he preferred to play with girls, with their dolls, and wanted to wear frocks and dresses. His mother encouraged his development by taking him to ballet classes, needlework, and flower arranging. Justin relished his...Read On

8

Taking panties as payment for sucking cock: A delicious arrangement

Wearing hot slutty panties and sucking four cocks

As you all know, I love stuffing my cock into panties and I love sucking dick. My lingerie collection is pretty big now, but I cannot seem to stop expanding it. One way that I have managed to keep my collection growing and ensuring that I have plenty of cute outfits to wear on my dicksucking expeditions is that I developed a very convenient relationship with a very generous sugar-daddy. ...Read On

14

The Secretary - Part 1

I receive an interesting job offer

A lot of my stories are based upon the more formative years of my sexuality. Things are much less complicated these days. There's less sneaking around as I am not quite so in the closet any more, as well as the fact I live alone in my own apartment. I divide my time quite evenly between my identities although work is somewhere I still don't bring my cross dressing. Sometimes I feel like a...Read On

8

Essence of woman

Gay boyfriend's mum shows affection

They placed John in their laps, turn by turn, as he rode their pre-match hard-ons. Their silk concealed behind their football kits: satin knickers, cami knickers, garters, bras, stockings and suspenders. John, or Janine, as he liked to be called, was the college tosspot. The college football team slept with him whenever their girls were away. The team guys were six foot two beefcakes...Read On

9

Returning To Old Habits

After an extended break, I return to an old hobby.

Like many cross dressers, I found my habit has a certain ebb and flow. I would bury myself into my kinky hobby for several weeks, only to hide everything away again. I used to have purges too from time to time, where I'd convince myself it was wrong and throw my clothes away, swearing I'd never do it again. The last time I purged was in my mid twenties. I'd been with my then girlfriend for...Read On

3

West meets East hospitality

Hospitality Indian style

The shalwar (Indian baggy trousers) felt so sensuous on Charles's legs and groin as he gently rubbed himself through the raw silk. He was wearing Rani's Mangla Sutra (Indian lady's wedding necklace) together with anklets that had individual toe rings. The more he thought about Rani, the closer his hard-on approached climax as the silky shalwar sent tingles down his spine. Rani was the head...Read On

7

Call Me Julie part 5

Julie is not the only one with a secret.

Kelly is kissing me passionately, and I am kissing her back. Her hands are all over me as she feels me up. My tucked package is straining against the material of my panties as she grabs and gropes at my feminine attired body. Her hand snakes its way under my dress and into my panties, which she pulls down enough to release my cock, and tugs on it vigorously. She breaks the kiss and snakes down...Read On

12

Peer Pressure, Both Ways...

Girlfriend's boyfriend cums to the rescue!

"Fucking pervert, fucking pouffe, tosser, sissy...." Lenny had become accustomed to these names over the years, as he went about minding his own business, but the lads from out of town were relentless, as they began pushing and shoving Lenny. He tried to walk away, but they roughed him up a bit, before laughing hysterically and then shooting off. Lenny wasn't physically hurt, just a...Read On

16

My birthday treat

After months of helping me dress, my neighbour plans a special night.

My next door neighbour had begun helping me with my crossdressing by buying me my own clothes, and despite her initial stipulation that I continue to dress in secret, we had experienced a moment where that had all changed. Once that day had passed, Ellie and I became almost inseparable. If we weren't together, we were texting or talking on the phone. We would do everything an ordinary pair...Read On

21
Banes1
away

The Day My Secret Was Discovered

My wife surprises me.

My wife and I have been happily married for four years. She is the dominant one in this marriage. Just recently I have discovered how much I enjoy wearing women's clothes. I love how the panties feel between my ass cheeks. The silkiness of the nylons on my legs as I slide them causes an erection every time.  My wife had no idea until one day when I had Friday off from work. As soon as she...Read On

6

Taking silk with Miss Ackleton

Cross dressing in silk, satin, and velvet.

The intercity train station was bustling with passengers, as well as trains, as folks prepared to head off in all directions. "While there's still time", were the words that Seymour could not get out of his mind. "What did she mean by those words?" he kept asking himself as he reached for inside jacket pocket to read the letter for the umpteenth time. The letter was hand written on the...Read On

9

Making friends with my housemates

People always react in different ways when they find out about my cross dressing. Girls are usually more accepting than guys but everyone is different. I was twenty-two when I went to university and decided I would be completely open about it with everyone I met there. I found that most people were pretty cool with it, although some took some time to get used to it. I spent the first...Read On