Crossdressing

libertina

My Girly Fantasy

A night with my friend changes everything between us

I wake up and smile, remembering where I am and who I'm with. I'm warm and comfortable, wrapped in your arms as you sleep. I think back to last night, finally showing you my girly side. We've been best friends for ages but I always had a crush on you. Finally, drunk on wine, I decided to do something about it. I came into the living room we share and straddled you; taking off my robe to...Read On

Added: 07 Feb 2012 | Category: Crossdressing | Avg Score: 4.82 | Tags: gay  crossdressing  panties  anal  boyfriend   | 6 Comments

SluttyTammyCD

Neighbor fun

Slutty fun with neighbors

It was a typical Friday night. I would hurry home from work to complete my ritual. Take all of the necessary steps for a lot of anal sex, shave all over and transition from a male to a female. I put on a typical “uniform” for the trip to his house. A lacy black top with a lacy black bra under (looked more like a teddy than a top), a short pleated black skirt, black stocking, garter, and...Read On

Added: 09 Nov 2011 | Category: Crossdressing | Avg Score: 4.9 | Tags: dressing  cum  slut  cd   | 5 Comments

lildifferent

A Fantasy to Remember

Halloween was rapidly approaching and my girlfriend of 2 years was planning something big. She had been a stripper for 10 years and was as kinky as they come. She and I had done a lot, so only a few of her fantasies were left unfulfilled. She had already had women and men, group sex, bondage, been a submissive and a dominate. We had a no holes barred policy. I could have any hole I...Read On

Added: 20 Aug 2011 | Category: Crossdressing | Avg Score: 4.89 | Tags: crossdressing  anal  group sex  bisexual   | 5 Comments

sweetriyacd

Losing my virginity

Sometimes you just have to give in

I'm a 21 year old attractive crossdresser from Mumbai, India. I am sharing a true story of how my roommate turned into a permanent fuck buddy! I've been crossdressing for 10 yrs now and have my own collection of all kinds of stuff you can think of. I moved into the city 2 years back and rented an apartment with a guy called Vishal who I didn't know at the time.  The first few days...Read On

Added: 03 Mar 2010 | Category: Crossdressing | Avg Score: 4.43 | Tags: crossdressing  virginity   | 6 Comments

ChelseyR

In Wonderland, Pt.1

Costume mandatory...

When I was in high school I was always very camp, which was probably why almost all of my friends were girls. This was definitely why I first ended up crossdressing. I was sixteen and round one of my 'girlfriends' house for a few drinks on Halloween before we went to a house party nearby. I never much cared for Halloween, so just came as myself. When I came in they all sighed since I wasn't in...Read On

Added: 07 Nov 2010 | Category: Crossdressing | Avg Score: 4.8 | Tags: alice  crossdress  party  halloween  teen   | 7 Comments

iltns2569

Friend Becomes My First Part 1

The true story of one my best friends becoming my first

*This is a true story of my first time having sex dressed a girl* It finally happened, and it was a dream come true. I started dressing as a girl when I was 17. For me, it started with a thong I stole from my mom's drawer which eventually went on to lingerie, to normal clothes, and all the way to dressing fully. Im now 24, and all I wanted to do was to show myself to a man and be the little...Read On

Added: 22 Jan 2012 | Category: Crossdressing | Avg Score: 4.28 | Tags: crossdresser  first time  anal  oral   | 7 Comments

cuckoldmalesub

Caught, Used and Loving It!

I was caught dressing up as female and used like a toy

I knew I had time now; my wife had gone out with her friendsand wouldn’t be back until 10pm at the earliest. As it was only 6:30, I knew I could spend time getting ready before playing around on the computer and enjoying a nice relaxing but exciting orgasm. My cock was more than ready as I hadn’t had sex for over a week and no chance to masturbate either due to either the kids being around or...Read On

Added: 05 Mar 2013 | Category: Crossdressing | Avg Score: 4.87 | Tags: crossdressing  caught  reluctant  bisexual   | 16 Comments

LingerieBoy

The Young Crossdresser Part 2

So after my little adventure at mom and dad's bookstore,the next couple of years were uneventful. I did have sex a couple of times with Phylis,the older lady that was part of mom and dad's swinger group. I knew that I was wanting something more,something was still missing and I kept thinking back to how the guy's cock felt as it spewed cum into my panty covered ass. Now I was 15 and...Read On

Added: 10 Jul 2008 | Category: Crossdressing | Avg Score: 4.6 | Tags:

cindytranee

My First Boyfriend - Part One

I learn to cross dress and get a boyfriend

Since my family had moved to our new house, Steve and I had become best friends. He lived next door and had moved in about a month before we did. With both of us being the new kids on the block we bonded quickly. He was two years older than me at eighteen and I had just turned sixteen a few months back. He was also taller and had more muscles than I did. He had tan skin and black hair where I...Read On

Added: 17 Dec 2011 | Category: Crossdressing | Avg Score: 4.92 | Tags: young  bi  oral  anal     | 10 Comments

hardjake

Crossdresser and I at Costco

I went to Costco over the weekend with my friends girlfriend. She went off shopping, and I went off to get a few things. I walked down some random isle, and saw a girl leaning down. I snuck a peek at her butt and saw a little bit of a thong showing over the top of her shorts. She was wearing a blue hoody. I looked up and saw that she had really short brown hair. I tried to see her face, when...Read On

Added: 04 Dec 2009 | Category: Crossdressing | Avg Score: 4.22 | Tags: crossdress handjob thong cum   | 2 Comments

phsusan

Susan is Complete

Love of pantyhose turns me into Susan

Like most of us, my cross dressing started with wearing pantyhose. This is a true story. My older sister (she was 14 and I was 9) would wear them to school (private school with uniforms) everyday. She started to notice that I would stare at her legs when she wore them. To this day I don't know why, but she would tease me trying hard for her not to be obvious about it, letting her skirt hike up...Read On

Added: 10 Feb 2009 | Category: Crossdressing | Avg Score: 4.41 | Tags: pantyhose lover   | 2 Comments

webbyhose

Becoming an Escort

The nights second cock spurted hot sticky cum on my face and I greedily pushed into my mouth faking my enjoyment of that bitter taste. My “lover” dressed and left the room. I lay back on the bed where two men had fucked me that night and pondered how I had got into this position. Despite myself my cock was rock hard in its silk panties stained with my own cum. 3 weeks earlier I had told...Read On

Added: 30 Dec 2010 | Category: Crossdressing | Avg Score: 4.46 | Tags: gay  feminisation  first time  anal   | 7 Comments

GirlyWorld

Uncle Joe

A surprise gift leads to unforseen pleasure

I had just returned from a long solitary afternoon walk in the forest. The house looked really pretty in the snow, with its fairy lights adorning the rafters and windows. In fact, it was quite picture perfect, so I stopped to take a photo. I framed the house against the white valley in the background, making sure that I included the lush green fir tree to the right of the house and avoided...Read On

Added: 31 Jul 2010 | Category: Crossdressing | Avg Score: 5 | Tags: crossdressing   | 9 Comments

PaulineWendy

All by mistake

A chance encounter

It all began by mistake. I had spent the morning at home, relaxing in one of my favourite outfits. I was starting to think that work beckoned, and had begun the transition back to drab. I took off my wig and make up, but decided to keep my panties, tights and bra on, as my clothes would hide what I was wearing. My attention was caught by a news item, and I sat watching the television for...Read On

Added: 23 Dec 2011 | Category: Crossdressing | Avg Score: 4.18 | Tags: crossdressing   | 5 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: 4.71 | Tags: | 13 Comments