Crossdressing

shazstoned

What's In The Name Shazstoned

It was a Saturday night some years ago, I was home alone, it was time to dress fully for the first time. I showered and had a good shave. I started with my false eyelashes on the top and bottom of my eyes, next the foundation and powder, eye shadow, a glittery green, dark red blusher to highlight my cheeks, black eye liner and masscarra followed. I added bright red lippy, all was applied...Read On

Added: 05 Sep 2009 | Category: Crossdressing | Avg Score: 4.11 | Tags: crossdressed slut  oral  drunk.   | 10 Comments

starbelliedboy

Fulfilling A Girl's Male Fantasy Part 2

Jenny and her friends have a party with a surprise.

Since our first meeting had gone so well, Jennifer and I started going out together. Other than the fact that in the bedroom I was the "man" only about half the time, it was a fairly normal relationship, apart from possibly being even more open with each other about our desires. One day a couple of months after our first encounter, we were both in her room talking and listening to music. ...Read On

Added: 31 Aug 2009 | Category: Crossdressing | Avg Score: 4.86 | Tags: crossdressing  bisexual  sissy  forced  strap-on  goth  lesbian   | 1 Comment

summer1979

Busted by a bud

Caught on home turf.

It's a hot summer day in 1994. Nowhere is a small, fairly poor, rural Illinois town; the kind of town where nobody locks their doors. Summer seems to be an average 19 year old. He goes to a small community college and works on the weekend's. He's kind of quiet and doesn't like to be around his parents. Both parents have jobs where they have to work the night shift. Summer's mom works for...Read On

Added: 29 Aug 2009 | Category: Crossdressing | Avg Score: 4.71 | Tags: crossdressing  anal  friends     | 3 Comments

CHRISSY_SISSY

Serving my master part 2

This is part two of how I was transformed into a sissy maid.

　 I’m a teenage white cross-dressing sissy: My master is a tall muscle bound black man. After my first encounter with him he told me to come home with him, as we walked to his car he had his hand on my ass. I felt so sexy as he fondled me. When we got into his car he grabbed me by the hair "Here’s the rule from now on I own you you’re my slave and I’m your Master, you will do everything...Read On

Added: 28 Aug 2009 | Category: Crossdressing | Avg Score: 4.71 | Tags: anal  gay male  interracial  crossdressing   | 1 Comment

CHRISSY_SISSY

serving my master part 1

I'm a submissive panty wearing sissy

　 　 My name is Chris I may have a penis but deep down I was born a girl. I have long red hair baby blue eyes a soft shapely hairless body and an overpowering obsession for wearing frilly lingerie. My obsession started at a young age I found a pair of my sisters panties in the bathroom and took them back to my room. I stripped off my clothes and rubbed the dirty panties over my...Read On

Added: 19 Aug 2009 | Category: Crossdressing | Avg Score: 4.33 | Tags: crossing dressing  gay  interracial  first time   | 2 Comments

starbelliedboy

Fulfilling A Girl's Male Fantasy Part 1

Jennifer has a surprise request for Jack.

"Get undressed," the pretty brunette told me, and I obeyed. She was called Jennifer, we'd met the night before at the rock nightclub, and I'd thought that she looked gorgeous in her goth make up so she invited me back to her place. It turned out that she was eighteen and still living at home, so we locked her door and did our best to keep quiet as we fucked the night away. Now it was noon,...Read On

Added: 18 Aug 2009 | Category: Crossdressing | Avg Score: 4.69 | Tags: oral  crossdressing  sex  strap-on  gender bending  anal   | 1 Comment

LisaLeeCD

Ray and the Halloween Party Part Two

Part two of my wild night at the Halloween party and with Ray...

   When Ray and I arrived at the front door at Sharon ’s house I noticed my lipstick on Ray’s lips from passing the tequila bottle and as I was wiping if off with my fingers the door sprung open. Sharon was dressed as a Playboy bunny and she looked surprised when she saw us. I thought it was because she recognized me but evidently not. “Well, well, Ray, you dirty dog....Read On

Added: 15 Aug 2009 | Category: Crossdressing | Avg Score: 4.86 | Tags: crossdressing  tranny  oral   | 16 Comments

LisaLeeCD

Ray and the Halloween Party

My friend Ray meets Lisa for the first time as we go to a Halloween party....

   I have had sex with a few guys since my last story but there nothing much worth writing about so I thought I would “go retro” and tell you about a hot experience I had in my senior year of high school.    At that time I kept my crossdressing pretty much private and only a handful of people knew about my slutty side as Lisa. Even most of my best friends had no clue. (At...Read On

Added: 10 Aug 2009 | Category: Crossdressing | Avg Score: 4.73 | Tags: crossdressing     | 9 Comments

SashaCD_ThongPanties

My First Thong

How the thong panty changed my sex life so young

When I was a little boy in grade school, I developed a curiosity so strong that it could not dare be mentioned to my parents...well, except for my father, since he was quite a perv despite being married to my mother who was more conservative than he was. Typical behaviors in a hispanic couple's life, really. No, it was not about my sexuality, but it involved underwear. Specifically, a...Read On

Added: 04 Aug 2009 | Category: Crossdressing | Avg Score: 4.76 | Tags: | 3 Comments

AmandaK

An Unforgetable Experience

Caught By The Best

I will never forget the day Carrie enter my secret world. It was the summer I was 17, I had been dressing my sisters clothes since I was about 8yo. In more recent years I had started buying a few of my own clothes and lingerie nylons and make-up. It was a Saturday and I was home alone and decided it would be a good day to dress and be girlie, excited about my day I waxed my legs and bikini...Read On

Added: 01 Aug 2009 | Category: Crossdressing | Avg Score: 4.44 | Tags: basement   | 4 Comments

LisaLeeCD

Loverboy Ricky

Nasty sex with my loverboy Ricky

It’s been some time since I wrote about my crazy life as a slutty crossdresser so with some free time right now I thought I might tell you about Ricky, one of my early boyfriends when I was a teenager….   Ricky moved into our neighborhood when I was 17 and he was 18 and I had a crush on him right away. He was so damn good looking with dark brown hair, brown eyes and strong...Read On

Added: 24 Jul 2009 | Category: Crossdressing | Avg Score: 4.48 | Tags: crossdressing  anal  gay  first time   | 9 Comments

Teresab

Panty Slut

Caught wearing my panties, he soon gets a taste of his own medicine

You little bitch! I can’t believe you're wearing my panties again. Do you want to be a girl? Do you? Well that bulge in your panties tells me you're lying. Come on in here Jennifer. That’s right, I told Jennifer all about you jerking off in my lingerie. I don’t think she believed me. Stay right there so Jenn can see what a little sissy you are. Isn’t he...Read On

Added: 07 Jul 2009 | Category: Crossdressing | Avg Score: 4.48 | Tags: panties  forced fem  blackmail   | 14 Comments

jools

Capri

My first driving lesson

Friend of the family -Bi Curious story This is my very first story, I hope you enjoy reading it and I hope it inspires you to contribute My name is Jools I grew up in the west country from the late 60’s until the present day My tale based on a true story happen in 1970. At the time I would be at the tender age of 16. When your young the time can't pass...Read On

Added: 05 Jul 2009 | Category: Crossdressing | Avg Score: 4.75 | Tags: bi curious  mind games  tights fetish  cock sucking   | 2 Comments

Teresab

Miss Teresa's Beauty School

Princess has been caught stealing at work and has to pay the price!

I wrote this story as a narrative and I made it into a 45 minute audio story. The Interview: Come in, I've been expecting you. I had a long talk with your boss the other day and it seems that you have a little fetish for women's underwear, isn't that right? In fact-you've been caught stealing things from the other girls lockers. Mostly their panties and pantyhose. Is it just too hard to...Read On

Added: 01 Jul 2009 | Category: Crossdressing | Avg Score: 4.79 | Tags: crossdressing  forced fem  sissy  strapon   | 3 Comments

simonelovesyou

Caught in a Prom Dress

I Should of Listened to What my G/F Said!!!!

If you can remember the stories LUCK RAN OUT AND I GOT CAUGHT then good this has escalated from there if not please read it first. It was a few weeks before my G/f college prom and said had her prom dress all prepared and hung up in the spare bedroom where i stayed. (her folks where very strict) As you can probably guess by now i wanted to try it on, it was a gorgeous gold long dress...Read On

Added: 30 Jun 2009 | Category: Crossdressing | Avg Score: 4.16 | Tags: caught  crossdressing  anal  torture   | 1 Comment