Crossdressing

Pamala2000

Pamala's first adventure

This happened to me years ago when i was in the Army

I joined the army after I quit school in the 12 th grade. After joining the army it put a crimp in my dressing up as a girl. I did wear panties whenever I got the chance but I really wanted to dress up completely as a girl. I wanted to go out dressed and I have to admit I was attracted to several guys in my unit. My third year in the army I went to Viet Nam in December 1967. I was in the 101...Read On

Added: 07 Dec 2010 | Category: Crossdressing | Avg Score: 4.94 | Tags: crossdressing  sex  anal   | 18 Comments

GirlyWorld

Jack's Little Bitch

Learning to be a girlfriend

Steph had been gone for about one week out of her two week visit to her Mom. She'd asked me to pick up the mail and water the plants while she was away, because her boyfriend, Jack, was also going to be away for the month on a business trip abroad. “Jack wouldn’t remember to water the plants even if he was there,” said Steph, laughing. “At least I can trust you.” Steph was right...Read On

Added: 10 Apr 2011 | Category: Crossdressing | Avg Score: 4.56 | Tags: crossdress  oral  bisexual  masturbation   | 4 Comments

jennaryder13

Prom Date- Part 1

Jody is forced to dress as a girl for prom.

Jody was pretty much a typical 18 year old boy. He liked sports, hanging out with his friends, and playing video games. However, Jody had one deep, dark secret. He was addicted to wearing his sister's clothes. Every time the house was empty and he had the chance, he would sneak into her room and try on something pretty. Jody was always mortified of getting caught so he was very careful....Read On

Added: 01 Dec 2011 | Category: Crossdressing | Avg Score: 4.48 | Tags: prom   | 3 Comments

sissyslut_trish

Caught in my girlfriend's lingerie by her friends

My girlfriend lives alone, so whenever I am at her house by myself, while she's out clubbing or working, I always take the opportunity to go through all of her sexy clothes and lingerie and dress up like the slut that I crave to be. I undressed and put on a pair of white fishnet stockings, a black thong, mini skirt, black and white see through top and a sexy pair of silver high heels. I set...Read On

Added: 03 Aug 2012 | Category: Crossdressing | Avg Score: 4.53 | Tags: crossdressing anal humiliation   | 9 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: 4.21 | Tags: crossdressing  anal  bondage  fellatio    

Willingsubmissive

A Fantasy Come True

My wife and I went on a four day vacation to Charleston to enjoy the sights and especially to enjoy the nights. Our first night there I was no sure how it would go. I was wandering if my wife could really get in the role of being a Dominatrix. Would she really enjoy having DD as her Slave? Could my wife become the Dominatrix that I want and need? All my questions were answered that night. ...Read On

Added: 14 Aug 2011 | Category: Crossdressing | Avg Score: 3.83 | Tags: submissive  watersports  domination     | 4 Comments

MicheleNylons

Violation

Michele is a closet TV and awaits her lover so they can play out their fantasy

Violation By Michele Nylons I have been home from work for over an hour; I lift my head from the brief that I have been reading by the light of a desk-lamp. The room is full of shadows. I look at the antique clock on the mantle and see it is approaching eight o'clock and I look over at the window; it is dark out. I close the file on my desk and then close the curtains in the study. I...Read On

Added: 15 May 2009 | Category: Crossdressing | Avg Score: 4.67 | Tags: crossdress  transvestite  reluctance  stockings  panties   | 3 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: 4.39 | Tags: crossdressing  female domination  bondage  cuckold   | 2 Comments

AshleyBarnes888

The Birth of Amber Lynn

A man plays dressup and realizes it has been the missing ingredient in his sex life

I had been dating Suzanne for about two months. She was a gorgeous woman I met while working as a computer technician at Aritech Computing. A successful sales consultant for the company, she made them a lot of money through all her sales. One look at Suzanne, and men would open their wallets to buy whatever new gadget or software she touted as being new and improved. As such, she in turn made...Read On

Added: 12 Sep 2011 | Category: Crossdressing | Avg Score: 4.92 | Tags: crossdressing  oral sex  anal sex  straight sex   | 13 Comments

Ginna_CD

Becoming Ginna

First time sucking cock, first time fucked, first time girl !

We were just over 16 years old when I and my childhood best friend Tim, discovered masturbation. And once we did, we couldn't have enough of it. More often than not we would be at secluded places jerking off over porn magazines. From then onwards I realised I was getting more excited watching Tim masturbating rather than the porn, and soon I started wondering rather intensively how would his...Read On

Added: 03 Feb 2012 | Category: Crossdressing | Avg Score: 4.86 | Tags: passive  cd  fucked   | 12 Comments

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

Added: 02 Nov 2010 | Category: Crossdressing | Avg Score: 4.86 | Tags: panties  crossdressing  anal sex  humiliation     | 3 Comments

Nicole94127

Crossdressing Fun From A Woman's Point of View

I have enjoyed reading the stories written by men to get a better understanding of what it is like to crossdress. As a woman, I find that I really enjoy and am very aroused with a feminized man. I guess I have always been a bit of a tomboy and enjoy doing athletic things, so being with a man that is the opposite seems natural to me. I used to play gender swap cross dress role play with my...Read On

Added: 26 Dec 2011 | Category: Crossdressing | Avg Score: 4.73 | Tags: crossdressing  gender role swap     | 21 Comments

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

Added: 12 Nov 2009 | Category: Crossdressing | Avg Score: 4.58 | Tags: crossdressing  masturbation     | 7 Comments

Markdwyer1984

Phoenix Park Night

My first time getting a blowjob from another man while wearing lingerie

I am a 32 year old married guy who happens to like wearing ladies' lingerie. My fondness for wearing lingerie goes back to my late teen years when I would wear my mother's clothes and underwear. I went on to wear my sister's undies and this continued into adult life where I have worn the undies of many ladies (without them knowing it). Until the time of this story, I never ventured...Read On

Added: 17 Sep 2010 | Category: Crossdressing | Avg Score: 4.73 | Tags: crossdressing  first time  bi  tights  blowjob   | 6 Comments

salidin

A weekend with Nancy part 3

Get used to it, you're going to be my bitch alot from now on.

Upon arriving back at the car Nancy said that we had to hurry to our next destination because it would be closing soon and then she instructed me to drive while Alice and herself got in the backseat. "Honey, do you know that porn shop up the road a couple of miles?" said Nancy. I nodded that yes I did and I was instructed to drive there quickly. At the porn shop, Nancy suggested that I...Read On

Added: 31 Jan 2011 | Category: Crossdressing | Avg Score: 4.94 | Tags: strapon  anal  crossdressing   | 4 Comments