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

Ginna_CD

Becoming Ginna

First time sucking cock, first time fucked, first time girl !

We were just over 16 years old when I and my childhood best friend Tim, discovered masturbation. And once we did, we couldn't have enough of it. More often than not we would be at secluded places jerking off over porn magazines. From then onwards I realised I was getting more excited watching Tim masturbating rather than the porn, and soon I started wondering rather intensively how would his...Read On

Added: 03 Feb 2012 | Category: Crossdressing | Avg Score: 4.86 | Tags: passive  cd  fucked   | 12 Comments

cindytranee

My First Boyfriend Part Four

I suck off a bunch of guys at a party and take two home to have a foursome

The drive home from the party was quiet because I had sucked off ten guys at the party and my mouth was sore and we were pretty drunk too. Two of his friends were following us home I assumed to have sex and party. I lay on the seat with my head in Steve's lap and rested while we listened to the radio. I asked Steve how were going to keep those two from finding out I wasn’t a real girl and...Read On

Added: 02 Feb 2012 | Category: Crossdressing | Avg Score: 4.81 | Tags: oral  anal  gang bang  kinky     | 3 Comments

cindytranee

My First Boyfriend Part Three

My boyfriend pimps me out to his friends

Steve and I had spent our first night together as a realcouple and in a real bed and it was wonderful. I had intended to wake him up with a blow job but he was already gone when I woke up so I had the whole day to wait for him to return from work. I spent the day just like a housewife would. I wore a house coat and some fuzzy slippers and after cleaning up the place sat down and watched...Read On

Added: 24 Jan 2012 | Category: Crossdressing | Avg Score: 4.53 | Tags: party  blowjob  pimp  whore   | 4 Comments

SluttyTammyCD

Gang banged at a private club

This is what happened when a friend took me to a private members only gay, bi, and transgender party

After yet another hot weekend at my friend Heberto’s house, I was packing up and getting ready to go home when he told me he had something “special" in mind for us next weekend. I begged him to tell me what he had in mind but he refused. So I left. My curiosity was peaked. The week dragged on thinking about all of the possibilities. The anticipation was killing me. Finally Friday...Read On

Added: 23 Jan 2012 | Category: Crossdressing | Avg Score: 4.76 | Tags: cum  blow job  fucking  snowballing   | 5 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

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

cindytranee

My First Boyfriend Part Two

My boyfriend and I get closer

NOTE- this story will make more sense if you read part one,it can be accessed through my profile page. The week leading up to today had been one of the longest of my life. I was very excited that today had finally arrived. My boyfriend Steve’s parents left early that morning and would not be back for three days. My parents had agreed to let me stay over while they were gone. Steve and I...Read On

Added: 17 Jan 2012 | Category: Crossdressing | Avg Score: 4.93 | Tags: bride  anal  oral passion   | 2 Comments

subguy

Wonderful crossdressing shopping experience

A wonderful Christmas eve to remember

Following is a true account of my recent experience of shopping for clothes (crossdresser, no sex). I just wanted to share a couple of very pleasant experiences I had shopping at the Natick Mall near Boston. It was the first time ever that I managed to shop with confidence and without any stress. I really want to give compliments to lovely women who made this possible (in case any one of...Read On

Added: 26 Dec 2011 | Category: Crossdressing | Avg Score: 4.74 | Tags: true  cd  crossdressing  nosex   | 13 Comments

Nicole94127

Crossdressing Fun From A Woman's Point of View

I have enjoyed reading the stories written by men to get a better understanding of what it is like to crossdress. As a woman, I find that I really enjoy and am very aroused with a feminized man. I guess I have always been a bit of a tomboy and enjoy doing athletic things, so being with a man that is the opposite seems natural to me. I used to play gender swap cross dress role play with my...Read On

Added: 26 Dec 2011 | Category: Crossdressing | Avg Score: 4.72 | Tags: crossdressing  gender role swap     | 21 Comments

LilPandaKisses

Surprise

Aubrey greets his boyfriend home from work in a new way. Slight BDSM ahead.

Aubrey swallowed the lump in his throat as his wrists grew sore from his restraints-being handcuffed to the headboard of the bed, naturally he grew stiff. Speaking of stiff... he peered down, under the frilly black miniskirt of his maid outfit was a visible bump, straining against the panties that constricted it, said lingerie was clinging to his soft pale skin. He bit a plump bottom lip...Read On

Added: 24 Dec 2011 | Category: Crossdressing | Avg Score: 4.69 | Tags: anal  oral  crossdressing  bdsm  femboy  gay  lingerie   | 7 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

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

jennaryder13

Prom Date- Part 1

Jody is forced to dress as a girl for prom.

Jody was pretty much a typical 18 year old boy. He liked sports, hanging out with his friends, and playing video games. However, Jody had one deep, dark secret. He was addicted to wearing his sister's clothes. Every time the house was empty and he had the chance, he would sneak into her room and try on something pretty. Jody was always mortified of getting caught so he was very careful....Read On

Added: 01 Dec 2011 | Category: Crossdressing | Avg Score: 4.48 | Tags: prom   | 3 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