Crossdressing

sissyslut_trish

Caught dressed like a sissy slut

My girlfriend was away for the weekend so I had the place to myself. I was feeling incredibly horny so I went through her knicker drawer and decided to dress up (which I've enjoyed many times before). I put on a really tight, pink thong, black fishnet stockings and suspenders, and her black mini skirt. I looked at myself in our full-length mirrored wardrobes. God, I looked so sexy and...Read On

Added: 10 Aug 2012 | Category: Crossdressing | Avg Score: 4.65 | Tags: crossdressing anal humiliation   | 5 Comments

kirankaur88

indian crossdresser

hiiiiiiiiii every one here's kiran from india ,punjab first of all its not a fictitous story ,it is  a real part of my life my actual name is rahul and me a guy now of 20 yrs old. so lets start frm my age of 12 yrs............................... me frm starting was very likely to kiddish me always remain at home .not to go any where else than in my street. in mid of june when...Read On

Added: 25 Mar 2009 | Category: Crossdressing | Avg Score: 4.55 | Tags: | 1 Comment

Daddysgurl

Dad Pimps Me Out

I think once dad caught Jack fucking me,he wasn't upset,but more so he thought of a way to use this to his advantage. After that it was nothing for me to walk around the house in womens clothing,for my dad and I had a talk and I told him that it felt right. One night when he brought home a sexy outfit for me,I knew he was up to something. He handed me a bag and said "here,go put this on". ...Read On

Added: 21 Jul 2008 | Category: Crossdressing | Avg Score: 4.71 | Tags: crossdressing   | 8 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: 4.7 | Tags: anal  gay male  interracial  crossdressing   | 1 Comment

purekink

Our Sissy Slave

Will you be our full-time cross-dressing lesbian boislut?

Let me remind you how you came to be in this situation before you refuse. I've been bi-sexual since I was old enough to have noticed how horny women made me. From the moment I noticed, I was unstoppable. My dominant personality seemed to bring me more girlfriends than I could really use. But I always thought the only thing better than a submissive girl is a submissive boy. And what...Read On

Added: 11 Apr 2010 | Category: Crossdressing | Avg Score: 4.7 | Tags: crossdressing  strapon  ffm   | 8 Comments

luvinia

s(he) finds her man

story when i replaced my friend at a wedding

My house was not more than 250 meters away from the bus stop where I got down; but the sudden and heavy downpour caught me totally unprepared. Being one those new housing colonies there were no houses or trees where I could take shelter. By the time I reached our new house I was drenched to my skin. My younger sister Putti who opened the door started laughing at my plight. My elder...Read On

Added: 01 Jan 2008 | Category: Crossdressing | Avg Score: 4.09 | Tags: crossdressing  crossdress     | 5 Comments

ThinkKinkyThoughts

She wears the pants, over her cock

I stepped off the plane after three days travelling and was looking forward to going home after a long few weeks of travelling for work. My work regularly has me travelling and I don’t seem to get home as much as I would like anymore.   But it does make it even more enjoyable when I do get home.   Leaving the gate, I walked down the corridor, past the last security checkpoint, and toward...Read On

Added: 28 Oct 2009 | Category: Crossdressing | Avg Score: 4.81 | Tags: cross dressing  strap on   | 4 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

luvinia

birthday gift

gift given to a cd by his/her boyfreind

hi to all my readers and freinds today i m going to tell u about my meeting with my boyfreind i was sleeping in my baby pink color nghtie it was early morning i felt that someone was at the door. i quickly woke up and somehow managed to change in to my shorts and vest striping my nightie i was wearing pantie inside my shorts and rushed to the door when i opened it i was surprised to...Read On

Added: 31 Aug 2008 | Category: Crossdressing | Avg Score: 3.71 | Tags: crossdressing  skirts  anal and oral sex  love  

cdbottom2

Telling Mom I'm A Crossdresser

A story of me being open with my mom as a crossdressing slut andher becoming my pimp. Plz comment :)

When I was younger, my dad had passed away leaving only my mom and I. She is 45 years old with long brown hair, bright green eyes and stood about 5'10" in height. She is also a fairly busty woman with a 30DD chest with about 35" hips and in pretty good shape for a woman her age. I had been crossdressing for a few years and my mother had caught me a few times wearing her clothes. The first...Read On

Added: 19 Feb 2012 | Category: Crossdressing | Avg Score: 4.83 | Tags: crossdressing  anal  oral  condom  toys  spanking  first time   | 13 Comments

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

hotvicky

Vicky's First Time

My first time having sex as Vicky

I was very open about crossdressing when I met my wife when we were in our 20s. She has been very supportive and helpful. She helps me with my hair, makeup, and picking outfits. We started having sex with me dressed up as Vicky. This soon escalated to her taking me with a strap on. I loved the times she would fuck my ass with her cock. I had never considered myself gay or bisexual but the...Read On

Added: 18 Jan 2012 | Category: Crossdressing | Avg Score: 4.89 | Tags: crossdressing  oral  anal  cum   | 12 Comments

watcherfun

All Dressed Up Part 2

I was dressed as a girl but then what was I meant to do?

*This is a continuation of my first story; 'All Dressed Up Part 1'* With that I took my first steps in the world as a girl, and what wonderful steps they were. At first I had hated the idea of even getting near some of the clothes, let alone shaving my legs and wearing them, but seeing that stunning girl in the mirror had somehow turned me around. I can't say I was particularly enjoying...Read On

Added: 15 Jul 2010 | Category: Crossdressing | Avg Score: 4.72 | Tags: mini  skirt  halter  top  blowjob  bj  first   | 4 Comments

LisaLeeCD

Truck Stop Tranny Sluts

Steamy Tranny encounter at a truck stop

My girlfriend and lover Candi and I were driving back to her place for some steamy tranny sex after a night of partying at a tranny/gay bar in town when we passed a truck stop on the highway. Buzzed and horny as we were, we laughed about stopping in the lot and doing so hookin’ as a means to get us some trucker cock. After a minute or two of silence, Candi said lets do it and before I...Read On

Added: 22 Apr 2009 | Category: Crossdressing | Avg Score: 4.90 | Tags: tranny  truck stop  blow job  tranny sex   | 8 Comments

Aimee_Cd

Halloween Fun

First time Out

My friend talked me into dressing up as a female this Halloween. It wasn't much of talking into; I was a closet cross dresser for sometime. The only person who ever knew was an old girlfriend, Mel, a few years back. It was a good thing she was bisexual because she was really into me wearing her clothes. She even mentioned that I looked better in her clothes than she did. So, I started wearing...Read On

Added: 03 Nov 2010 | Category: Crossdressing | Avg Score: 4.61 | Tags: fetish   | 7 Comments