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cuckoldmalesub
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1936Storyguy

Crossdressing

31
vote
GirlyWorld

The Panty Princess

Dominant girlfriend discovers her love for submissive boyfriend

Jane and I had only been living together for three weeks when I was caught red-handed. I was mortified when I saw her in the mirror, standing behind me with her mouth wide open. She had managed to come through the front door, up the stairs and into the bedroom without making any noise. I tried to explain that it was the first time I’d ever done such a thing, but she was having none of it. ...Read On

Added: 11 Jul 2011 | Category: Crossdressing | Avg Score: 4.86 | Tags: cross-dressing  humiliation  femdom  panties  blowjob  straight sex   | 14 Comments

6
vote
ejls

Can't Judge A Book By Its Cover

Not everything is as it seems.

Hillary sat on the bench outside the courtroom that Monday morning. She tugged at her skirt, trying to make it appear longer. She tucked stray tendrils of hair back into her casual chignon. Hillary was nervous and it showed. Even though everyone told her that she had an absolute barracuda for a lawyer, she still had nightmares as to how this would all turn out. Yes, Will had verbally agreed...Read On

Added: 10 Jul 2011 | Category: Crossdressing | Avg Score: 4.67 | Tags: crossdressing  cheating  oral   | 4 Comments

12
vote
ssuzie

Suzie and Cindy are taken to their first gay club

this is my fantasy life

As Cindy walked into the room with the outfit I picked for her, she had a distinct glow of a satisfied girl. Harry and Jack added pink nail polish, matching garter belt, thigh high fishnet stockings, jewelry, high heels and they cut bangs into her hair. She really was pretty. The three of them stood there while I was still riding Joe's cock, he was in no hurry. I must be becoming a good...Read On

Added: 08 Jul 2011 | Category: Crossdressing | Avg Score: 4.67 | Tags: oral  anal  crossdressing  prostitution  loving it  

16
vote
ssuzie

I am Suzie

This is my fantasy.

The coach was lubing up his cock. It actually was getting bigger. The veins along the shaft were thick and gorged. I could not take my eyes off it. Then he started humping the crack of my ass. I knew he was letting me feel how huge he was against my ass. I was so turned on that I started to wiggle my ass and grind his cock. He enjoyed that so much, he stopped humping me and let me do all...Read On

Added: 02 Jul 2011 | Category: Crossdressing | Avg Score: 4.81 | Tags: oral  anal  crossdressing  blacmail  surrender   | 4 Comments

15
vote
ssuzie

the day i became Suzie chapter 4

this is my fantasy

I went back the next day dressed sexier than ever, but Jack and Harry did not show up. I waited for hours. Then cried all the way home. I cried myself to sleep three nights in a row. Now I knew how a women feel after being fucked then forgotten. But then on the fourth day Harry called. I instantly went into my sweetest voice and asked, "Where have you been?" "Guy stuff Suzie.You...Read On

Added: 29 Jun 2011 | Category: Crossdressing | Avg Score: 4.87 | Tags: oral  anal  crossdressing  blackmail  gay bar   | 3 Comments

28
vote
cdbottom2

The Slut Within

This is my first story. If you like it please comment and I will write chapter two :)

I was 22 years old at the time, and I had been crossdressing for a few years. For some reason I could never control my desire to put on women's clothes and prance around my apartment looking all sexy and slutty. Normally I can never decide what specifically to wear as I like to change it up all the time, from wearing latex lingerie to sexy roleplay outfits and beyond. I am 5'9 with a...Read On

Added: 29 Jun 2011 | Category: Crossdressing | Avg Score: 4.81 | Tags: group sex  fetish  bdsm  spanking  toys  first time  interracial   | 11 Comments

18
vote
anotherfeeling

Teenage CD Awakening Part II

A teenage boy widens his crossdressing horizons by starting to wear his mother's clothes

I had crossed the Rubicon. I had tried on my sister's panties for the first time. Now I felt guilty. Incredibly guilty, and dirty. I went to school as normal the next day, but despite the guilt I couldn't get the amazing thrill of trying on that little pair of blue and white striped cotton panties out of my head. As 3.30pm and with it the school bell neared, the overwhelming urge to do...Read On

Added: 27 Jun 2011 | Category: Crossdressing | Avg Score: 4.78 | Tags: crossdressing  sister  mother  panties  tights  skirts  dresses   | 4 Comments

13
vote
germanwulf40

Becoming Vanessa, Part I

After catching her boyfriend cheating on her, Amelia decides to use her evidence as leverage.

It had been a long day for Amelia and her live-in boyfriend, Victor. They had just moved into a new town, and finally had all their boxes in their new house. Nothing was unpacked yet, save for their home computer, which Amelia insisted on getting hooked up straight away. "I don't see what the big rush is," said Victor, as he turned on the computer. He sat comfortably in their...Read On

Added: 26 Jun 2011 | Category: Crossdressing | Avg Score: 4.92 | Tags: crossdressing  feminization   | 5 Comments

12
vote
ssuzie

the summer I became Suzie chapter 3

this is my fantasy

I woke up early, hell I could not sleep any way! I had so many wet dreams about what happened yesterday, I had to change my sheets. After throwing the sheets and yesterday's outfit in the wash, I went back to my bedroom to take a shower. As I soaped up, all I could think about was Harry and Jack's huge cocks. I lubed up my pussy. And after drying off, painted my toe nails whore red. I...Read On

Added: 25 Jun 2011 | Category: Crossdressing | Avg Score: 4.83 | Tags: oral  anal  crossdressing  blackmail   | 1 Comment

19
vote
ssuzie

the summer I became Suzie chapter 2

this is my fantasy

CHAPTER 2 My eyes follow a trail of goosebumps to where Jack's gentle tongue teased my sensitive nipples to life, driving me crazy. He reached into a pocket of his discarded shorts and pulled out a tube then demanded I turn around so I could see my pussy. "Wiggle that ass and tell me how you loved sucking Harry's cock"! Jack grated. "Oh yes, I loved sucking his cock." "Can you still taste...Read On

Added: 24 Jun 2011 | Category: Crossdressing | Avg Score: 4.68 | Tags: oral  anal  crosdresing  blackmail   | 3 Comments

15
vote
ssuzie

the summer I became Suzie

this is my fantasy

I was 18 years old and taking estrogen for about two years. As my ass and tittles started to grow my desire to dress up became all consuming. I wore sexy panties to school everyday and the excitement about getting caught, grew as well. I was very tiny for my age and picked on by the jocks at school regularly. I'm 5foot 5inches tall, with long brunette hair and blue eyes. I had no body hair and...Read On

Added: 23 Jun 2011 | Category: Crossdressing | Avg Score: 4.8 | Tags: oral  anal  crossdressing    

31
vote
Karin

Old Friend, New Relationship-Part 1

As it turns out, I confided my crossdressing desires in just the right person

Old Friend, New Relationship-Part 1 I met Karen in my divorce support group while I was dealing with my second divorce and she was trying to cope with her first. About the only thing that we had in common was that both our spouses had cheated with good friends of ours. She was a couple years older and very attractive. I remember that she always dressed so well for our group meetings. We...Read On

Added: 11 Jun 2011 | Category: Crossdressing | Avg Score: 4.93 | Tags: crossdressing  feminization  blowjob  beauty salon  first time   | 10 Comments

14
vote
anotherfeeling

Teenage CD Awakening Part I

A tale of a teenage boy’s first overwhelming urge to try on a pair of panties

As a child I lived in a town in the North of England. It was a fairly conservative place, where boys were expected to grow up to be men, and girls to become women. Despite this my mother was a fairly liberal person, and by the time I’d reached the age of 17 the topic of sex had already been raised in our house. Sex between men and women of course, with the aim or perhaps the danger of...Read On

Added: 19 May 2011 | Category: Crossdressing | Avg Score: 4.43 | Tags: crossdressing  sister  panties  first time  masturbation   | 4 Comments

36
vote
anotherfeeling

Put it on!

A not-so-reluctant housemate dresses for his live-in landlord

I was living and working in London, my first job after college. No chance of having a place of my own with these crazy house prices and this being my first job at the age of 23, so I rented a room from a guy older than me, in his mid-30s. His name was Steve and he was a masculine type, split up from his wife but seeing a feisty Spanish woman called Manuela. There were big arguments now and...Read On

Added: 16 May 2011 | Category: Crossdressing | Avg Score: 4.85 | Tags: first time  housemate  crossdresser  anal   | 17 Comments

27
vote
Audio version available
howaboutme51

My first time

First time with a CD. First gay experience.

My first story. And it is the true story of my first encounter with a CD. With a click of the mouse, I had committed… I was going to meet a cross dresser just a few miles from home. Could I go through with it? Is it really what I wanted? Who was I kidding? Of course I wanted it. Now it was time to just suck it up, princess. I took a quick shower and the dressed in my tiniest,...Read On

Added: 09 May 2011 | Category: Crossdressing | Avg Score: 4.92 | Tags: cd  oral  anal   | 6 Comments

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