Crossdressing

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: 4.82 | Words: 6,290 | Tags: crossdressing  bisexual  sissy  forced  strap-on  goth  lesbian   | 2 Comments

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: 4.81 | Words: 2,088 | Tags: crossdressing  anal  friends     | 4 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: 4.5 | Words: 1,072 | 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: 4.58 | Words: 738 | Tags: crossing dressing  gay  interracial  first time   | 5 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: 4.67 | Words: 2,938 | 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: 4.79 | Words: 1,157 | Tags: crossdressing  tranny  oral   | 19 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: 4.71 | Words: 1,666 | Tags: crossdressing     | 12 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: 4.77 | Words: 2,508 | Tags: | 4 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: 4.48 | Words: 1,728 | 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: 4.6 | Words: 976 | Tags: crossdressing  anal  gay  first time   | 10 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: 4.63 | Words: 714 | Tags: panties  forced fem  blackmail   | 15 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: 5 | Words: 4,396 | Tags: bi curious  mind games  tights fetish  cock sucking   | 3 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: 4.84 | Words: 5,508 | 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 | Words: 1,123 | Tags: caught  crossdressing  anal  torture   | 4 Comments

pantylovincumguzzler

having some in panties with friend

guzzling cum for the first time

First time ever sucking cock in panties:              This is the first encounter Taylor had with another man. Taylor had just started wearing his mothers panties after taking interest in a mesh thong he found in the laundry. After a few weeks of wearing them he wanted to share his passion with someone else but never thought of who it could be with. All he knew is that it had to happen...Read On

Added: 26 Jun 2009 | Category: Crossdressing | Avg Score: 3.87 | Words: 582 | Tags: gay male  oral  anal  first time   | 8 Comments

Erincd1785

Caught

i was caught by my Hated(at the time) Step-father

I see all these girls with the first time or the first time they got caught dressing and it turns me on looking back and thinking of mine. Well I was young when I started getting into my moms and soon to be step sister’s clothes. My mother divorced my father when I was young but never really knew my dad do to the fact that he was always in the military and my mother was tired of moving...Read On

Added: 16 Jun 2009 | Category: Crossdressing | Avg Score: 4.78 | Words: 2,975 | Tags: crossdressing  first time  oral  anal   | 12 Comments

cad4488

my first time

    I’m 28 now. I have been interested in women’s clothing as long as I can remember. I can remember when I was around 7 my sister caught me trying on a pair of her panties that I stole out of her room, I don’t think she ever told on me about that. As I grew I was always stealing pantyhose, dresses, skirts and etc from mostly my family and my friends sisters. I wasn’t really ...Read On

Added: 11 Jun 2009 | Category: Crossdressing | Avg Score: 4.67 | Words: 1,146 | Tags: | 1 Comment

summer1979

The Afterparty Part 2

As Summer lay in a pool of sperm soaken sheets, she dazed in and out from the hangover and the multiple orgasms she just had. She dazed in and out, coming into consciousness as she heard voices of two men down the hall. Neither one was the voice of Pete. The door was still open and the voices got closer. It took a lot of her strength just to try and pry her legs close as much as possible...Read On

Added: 03 Jun 2009 | Category: Crossdressing | Avg Score: 4.29 | Words: 1,479 | Tags: crossdressing  bondage  fetish   | 1 Comment

CDinhiding1

Warehouse slut

There I sat at my computer, ready for another morning of chatting with my new online lover, much like all other mornings for the last two weeks.  It had become quite routine for us to chat for about an hour in the mornings, then off to our lives.  I was, quite honestly, starting to lose interest, figuring he was just another of the "Internet fakes".  We have all run into them, the guys who...Read On

Added: 01 Jun 2009 | Category: Crossdressing | Avg Score: 3.2 | Words: 1,428 | Tags: | 1 Comment

summer1979

The Afterparty

Steve awoke dizzy and confused. His head was spinning from all the alcohol he consumed from the party last night. As he tried to focus his eyes in the pitch black bedroom he realized he was bound to each corner of the bed. He struggled to free himself but the straps were to tight. It wasn't his bedroom; the sheets didn't feel the same and the bed was much bigger than his. Perhaps someone...Read On

Added: 31 May 2009 | Category: Crossdressing | Avg Score: 5 | Words: 1,592 | Tags: crossdressing  bdsm  voyeur  

CDinhiding1

Caught by Uncle in Aunts things

When I was a young boy, I started to find a fascination with feminine things.  Not sure how it started, but one day I found myself trying on some of my Moms things and enjoyed the feeling.  The issue I found early was that my Mom was very vanilla in her things, so I started to explore with an Aunts things, one I spent a lot of time with, as her son and I were very close.  She had very...Read On

Added: 29 May 2009 | Category: Crossdressing | Avg Score: 4.17 | Words: 964 | Tags: | 2 Comments

CDinhiding1

Caught at the Target

I had been dressing in private for years and never have tried to be passable, as I get my thrill out of being all man to the world, yet so girly just underneath what everyone sees.  I decided that I wanted a thrill, so I went to the local Target, with my leopard panties, matching leopard camisole, black garter belt and with stockings on, under my man clothes.  I picked out a pair of Dockers...Read On

Added: 28 May 2009 | Category: Crossdressing | Avg Score: 4.5 | Words: 1,133 | Tags: | 4 Comments

MicheleNylons

Whores and Pimps - Part III

Third installment; our reluctant transvestite heroine gets a gang bang

Whores and Pimps - Part III By Michele Nylons   Michele pulled at her bonds, struggling and wriggling on the bed trying to break free for a few minutes until she realised that she was securely tied and had no way of escaping. Ellie sauntered over to the bed and looked down at Michele, "Well honey, looks like we have you just where we want you; I think we are going...Read On

Added: 27 May 2009 | Category: Crossdressing | Avg Score: 4.67 | Words: 4,006 | Tags: crossdresss  transvestite  nylon  stocking  pantyhose  

tinycush

The Opportunity

a journey from gentle travestism to anal slut

THE OPPORTUNITY PART ONE     I suppose looking back, that my childhood was to blame, that is if there was any real blame to be attached. It could have just been my inherited genes so I can happily blame my mother and father for being the smallest in the class, but I somehow also got left out when the popularity genes were issued, I became a loner and spent far too much...Read On

Added: 26 May 2009 | Category: Crossdressing | Avg Score: 3.8 | Words: 785 | Tags: | 1 Comment

summer1979

Airing Out the Laundry

sex at the laundry mat

Rick was so excited to be moving to the big city. He was 22, from a small town, and got a good factory job in the city a few hours from his home town. Rick would be far enough away from his parents that Renae would be able to roam free. Rick found a little 2 bedroom apartment on the ground floor of a building in a gay community, though he did not tell his parents it was. Rick's parents...Read On

Added: 24 May 2009 | Category: Crossdressing | Avg Score: 4.46 | Words: 1,378 | Tags: anal  crossdressing  oral  firsttime   | 1 Comment

summer1979

Summer sexing a friend

A tale of sex, not love.

The night was especially dark that night. The moon was hid by a blanket of clouds. It was only 6:30, but that time of year it always gets dark that early. I left the empty bar after a couple of drinks, but I didn't want to go home. I wore skin tight jeans, a cute little tee, some cute tennis shoes, and a sexy underwear set. I took a little detour and found that Rod was having a fire....Read On

Added: 21 May 2009 | Category: Crossdressing | Avg Score: 4.39 | Words: 1,167 | Tags: crossdressing  anal  oral  rimming  voyeur  

summer1979

Summer in the fields

A one nooner stand

Steve is an average 19 year old on the outside. He has a full time job, a live in girlfriend (Amanda), divorced parents, and 2 cats. On the inside he's about to erupt. Summer is the eruption. Summer is Steve's "alter ego" who comes around every now and then. Steve used to let Summer drive around on the many less traveled roads in the area. Summer has never been with a guy, and she only...Read On

Added: 20 May 2009 | Category: Crossdressing | Avg Score: 4.63 | Words: 841 | Tags: oral  anal  crossdressing  rimming  roleplaying   | 1 Comment

summer1979

A night at the resturant

I was looking sexy enough to eat at the resturant.

I met John online; he was the owner of a small town restaurant, who was also married.  I agreed to meet him that night after he closed.  When I pulled up to the restaurant the lot was dark.  I hustled up to the door in my tight mini and stiletto heels, my heart was racing faster with each step.  When I got to the door John was waiting and quickly let me in.  We sat in the back and he offered...Read On

Added: 18 May 2009 | Category: Crossdressing | Avg Score: 4.5 | Words: 471 | Tags: gay  crossdressing  anal   | 6 Comments

LisaLeeCD

The very first time....with lots more to come...

My very first sex as a crossdresser.

I guess we all remember our “first time”, and in my case the first time I was with a man while dressed was a awesome experience that I still remember vividly, and it happened by accident.   I started crossdressing when I was about 14 due to my fascination with sexy women. The first time I slipped into a bra and panties and put on mascara and lipstick I knew I was hooked. I felt...Read On

Added: 18 May 2009 | Category: Crossdressing | Avg Score: 4.75 | Words: 1,910 | Tags: | 14 Comments

MicheleNylons

Whores and Pimps - Part II

The party begins and Michele has fun with Jill however the evil TV Ellie has other plans

Whores and Pimps - Part II By Michele Nylons Michele sat silently in the car as she watched the taillights of the police car disappear in the distance; the bitter aftertaste of the policeman's sperm still in her mouth. She was confused; the fat cop with his stubby fat cock had forced her to fellate him; but she had become sexually aroused and hadn't even realised it. She...Read On

Added: 16 May 2009 | Category: Crossdressing | Avg Score: 4.56 | Words: 4,245 | Tags: crossdress  transvestite  reluctant