Crossdressing

NylonsLover88

She'll Never Know... (Part 1)

A young man discovers a taste for the finer things in his wife's lingerie drawer.

Once again they had argued before she went to work. The reason was also the usual one – sex. This particular morning Mark had woken unusually early, with his usual erection. Deciding to test Clare's mood, he had rolled over and nudged his naked penis against her, just after the alarm had gone. Letting his hand slide up her thigh, she had moaned gently and pushed back into him, letting his...Read On

Added: 29 Aug 2014 | Category: Crossdressing | Avg Score: 4.56 | Words: 648 | Tags: panties  pantyhose  masturbation   | 10 Comments

cdbottom2

Missy Returns

It had been a long time from the seven days I spent with my studs, but sadly I went off to school and Missy had to go on an extended vacation. However, school did not work out as planned and I found myself in a new city and my own apartment with a small job. I had to help pay the bills. For a while I lived with a roommate who was a little homophobic and despised the ideas of trannies. He...Read On

Added: 26 Aug 2014 | Category: Crossdressing | Avg Score: 4.43 | Words: 4,031 | Tags: crossdressing  oral sex  sci fi  alien  stud  ufo   | 1 Comment

cum_dump_boy

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

Added: 28 Jul 2014 | Category: Crossdressing | Avg Score: 4.58 | Words: 1,351 | Tags: crossdressing  anal  cum   | 8 Comments

vanessagrrl

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

Added: 24 Jul 2014 | Category: Crossdressing | Avg Score: 4.63 | Words: 1,013 | Tags: crossdressing  anal  oral  hormones  making love  wedding   | 7 Comments

satisfierest

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

Added: 21 Jul 2014 | Category: Crossdressing | Avg Score: 4.09 | Words: 628 | Tags: strip poker  three woman  one loser  no-sex   | 6 Comments

CourtneyFux

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

Added: 18 Jul 2014 | Category: Crossdressing | Avg Score: 4.79 | Words: 3,685 | Tags: crossdressing  oral sex  exhibitionism  bisexual  daddy   | 9 Comments

CourtneyFux

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

Added: 16 Jul 2014 | Category: Crossdressing | Avg Score: 4.78 | Words: 3,825 | Tags: crossdressing  exhibitionism  oral  anal  group sex  bisexual  voyeurism   | 7 Comments

CourtneyFux

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

Added: 15 Jul 2014 | Category: Crossdressing | Avg Score: 4.88 | Words: 5,652 | Tags: crossdressing  exhibitionism  oral  anal  group sex  bisexual   | 10 Comments

CallmeJulie

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

Added: 06 Jul 2014 | Category: Crossdressing | Avg Score: 4.8 | Words: 1,195 | Tags: bisexual  anal  oral   | 10 Comments

HollyInPantyhose

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

Added: 02 Jul 2014 | Category: Crossdressing | Avg Score: 4.88 | Words: 1,919 | Tags: crossdress  pantyhose  vibrator  high heels  slut  cum  humiliation   | 3 Comments

shootersr9

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

Added: 28 Jun 2014 | Category: Crossdressing | Avg Score: 4.67 | Words: 6,995 | Tags: bisexual  kissing  oral  cock  anal  pussy  tits   | 4 Comments

mtnbiker1

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

Added: 27 Jun 2014 | Category: Crossdressing | Avg Score: 3.89 | Words: 1,478 | Tags: lingerie  masturbation  sex toys  pantyhose  girdles  bras  foundation garments   | 3 Comments

Jess_cd

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

Added: 20 Jun 2014 | Category: Crossdressing | Avg Score: 4.8 | Words: 1,956 | Tags: maid  lingerie  submission  oral  anal  cum   | 8 Comments

SxyJackyLeggs

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

Added: 19 Jun 2014 | Category: Crossdressing | Avg Score: 4.63 | Words: 1,066 | Tags: crossdressing  toys  masturbation   | 16 Comments

jerrixdresser

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

Added: 14 Jun 2014 | Category: Crossdressing | Avg Score: 4 | Words: 936 | Tags: crossdressing  anal  black     | 3 Comments

marietv

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

Added: 07 Jun 2014 | Category: Crossdressing | Avg Score: 5 | Words: 1,902 | Tags: creampied  transvestite  big cock  master/slave   | 13 Comments

Jess_cd

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

Added: 02 Jun 2014 | Category: Crossdressing | Avg Score: 4.84 | Words: 2,200 | Tags: lingerie  oral  anal  cross dressing  stockings  submission   | 15 Comments

vanessagrrl

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

Added: 30 May 2014 | Category: Crossdressing | Avg Score: 4.8 | Words: 619 | Tags: crossdressing  toys  phone sex  ass play   | 7 Comments

Jess_cd

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

Added: 24 May 2014 | Category: Crossdressing | Avg Score: 4.92 | Words: 2,045 | Tags: lingerie  masturbation  domination   | 13 Comments

Jess_cd

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

Added: 22 May 2014 | Category: Crossdressing | Avg Score: 4.93 | Words: 1,399 | Tags: solo  cross dressing  lingerie  toys  masturbation   | 12 Comments

CallmeJulie

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

Added: 19 May 2014 | Category: Crossdressing | Avg Score: 5 | Words: 646 | Tags: bi  oral  anal  dp   | 3 Comments

Jess_cd

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

Added: 18 May 2014 | Category: Crossdressing | Avg Score: 4.89 | Words: 1,822 | Tags: crossdressing  helping  oral  lingerie  strap on   | 15 Comments

Jess_cd

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

Added: 14 May 2014 | Category: Crossdressing | Avg Score: 4.73 | Words: 2,157 | Tags: lingerie  straight sex  oral  toys  dressing   | 5 Comments

SkittleMonster

Jack's Dirty Secret

Jack walked into his bedroom, seeing his wife laying on the bed with a dildo in hand.

Jack and Mary had been married for ten years or so. Mary never thought that Jack would keep such a large secret from her. She sat at the house all day and did laundry, Jack's and hers. She never usually did his since he's picky, but she was bored and it needed to be done. As she was putting away some of Jack's clothing in his dresser, she saw something. It was a shiny pair of silk gray...Read On

Added: 08 May 2014 | Category: Crossdressing | Avg Score: 4.78 | Words: 1,355 | Tags: wife  husband  anal  vaginal  sex  love  marriage   | 7 Comments

Jess_cd

One of my first times

My first time with a guy

They say you never forget your first time. For me that's kind of true but in my attempts to seduce over the years I've claimed to have so many first times and I definitely don't remember all of them. Being bisexual and, of course, with my dual gender identities I have probably had more first times than most though. I was still cross-dressing in secret in my late teens and I'd never had...Read On

Added: 04 May 2014 | Category: Crossdressing | Avg Score: 4.76 | Words: 1,146 | Tags: cross dressing  gay  anal   | 13 Comments