Crossdressing

summer1979

Work Hard, Play Hard

Expect the unexpected

After a long hard day of work, everyone decided to go to the bar after work. It was a busy day and everyone was stressed out; a beer amongst friends was just what the doctor ordered. The whole gang met at a Gino's, a local bar in a small Illinois town. The bosses were buying round after round, till everyone was all nice and liquored up. There was quite the crowd; about 15 in all. Dirty...Read On

Added: 18 Oct 2009 | Category: Crossdressing | Avg Score: 4.6 | Tags: coworker  crossdressing  drinking   | 5 Comments

Km44

Wife's crossdressing fantasy Part 3

I had to find a way to repay my wife for the wonderful anniversary gift she game me.

This is a work of fiction. Any resemblance to any person, or incident is strictly coincidental. My Wife's Cross dressing Fantasy 3 Then my wife looked at me and said “Happy anniversary darling.” How did she know the effect this experience would have on me. I was changed forever. It was such a wonderful experience. She deserved that I come up with something just as exciting for her,...Read On

Added: 10 Dec 2012 | Category: Crossdressing | Avg Score: 4.85 | Tags: crossdressing  oral  anal  group sex   | 8 Comments

Stephanie008

How I became Stephanie

Before I was Stephanie, I was a bisexual kinky boy named Steve. After I hit puberty I had explored my bisexual desires with some other guys my age. It wasn’t until I met Patti and Bill off an adult sex website that my deep erotic desires were uncovered. Pattie and Bill were an older bisexual couple and the only ones who responded to my ad. They liked that I was young, 18 at the time, open...Read On

Added: 18 Aug 2012 | Category: Crossdressing | Avg Score: 4.90 | Tags: crossdressing  incest  roleplay  anal  bisexual   | 16 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: 4.55 | Tags: | 1 Comment

pantyboy4u2do

GurlsOut

Having been into womens clothing since an early age,as I got older I often wondered about going out dressed up and hitting a local bar as a girl. Well I finally got my chance back in 1984. I was in the Air Force stationed in North Carolina and had already made a connection with a local man down there and we had sex on a pretty regular basis. He knew of my desire and one night we decided...Read On

Added: 13 Oct 2008 | Category: Crossdressing | Avg Score: 4.34 | Tags: | 4 Comments

trinitytowers

A Nanny Femtastic - Chapter 1

A NANNY  FEMTASTIC! Chapter 1 My story starts during a very bleak time in my life where I was unable to find continuous work of any meaningful type. I had, I suppose, looking back now, rather stupidly pursued Child and Nursery Care as a further education route. Much to my parents consternation!  Yes I was the only guy in the college but I thought I would soon move into...Read On

Added: 31 Jan 2010 | Category: Crossdressing | Avg Score: 4.62 | Tags: | 2 Comments

LingerieBoy

In An Alley

It's a lonely fall night,I'm walking down a fairly empty street in town. Not the best part of town,but it's my only way to get home. I am in my grey business suit. Grey jacket,grey knee length skirt,black blouse,black pantyhose,black panties and bra,brunette wig and black heels. As I walk, the people that are out,glance my way,checking me out as I go through their neighborhood. Run...Read On

Added: 14 Jul 2008 | Category: Crossdressing | Avg Score: 4.57 | Tags: | 2 Comments

mredd

Tammy, Lisa, and Karen part 1

This is my first story so please give me some feed back.

It was Friday and the first thing I wanted when I got home was a nice warm bath to clean off the day's hard work. I filled the tub with hot water and added some bubble bath. I shaved my legs and underarms. As I slid under the hot water I looked at my toes peeking through the bubbles, and realized I needed to reapply some polish. After a long soak I got out, dried myself off and went to...Read On

Added: 11 Aug 2012 | Category: Crossdressing | Avg Score: 4.85 | Tags: dressing room  mall  lingerie  panties  oral sex   | 16 Comments

cindytranee away

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

KrissyS

The Adventures of Kristof and Marci Part 3

Krissy's training continues and gets a sexy surprise when Marci receives a special visitor.

The following morning I awoke early and slipped out of bed. Gathering up the clothes I had prepared the night before I left the bedroom and headed downstairs to the study and dressed myself. This morning’s theme was all black, a six strap suspender belt, full fashioned nylons, a little swing skirt, lace thong and high heels, I was naked from the waist up, except for my nipple chain. I knew...Read On

Added: 17 Apr 2010 | Category: Crossdressing | Avg Score: 4.79 | Tags: crossdressing  slut training  watersports  ffm  bi  incest  mother and daughter  

irishfella

The slight mix up

New place New underwear Old girlfriend

Let me introduce myself I'm Jake. I'm a 23 year-old man, who recently got a place of my own. I decided to do a little bit of shopping for new underwear because I left mine in my parents home and I only have the pair I'm wearing and also to get some food and drink, for the next week or so. I started with some specials which were right where I entered the store. Soon after that, I grabbed...Read On

Added: 20 Jun 2012 | Category: Crossdressing | Avg Score: 3.94 | Tags: crossdressing  strap-on  anal   | 2 Comments

jessicahahn

Sissy at the Bookstore

Or how I humiliated myself in drag

I had gone to adult bookstores for many years and had done it in drag many times but never dressed as a sissy and never during the day. On this day I was so involved in humiliating myself that I decided that I need to take that extra step and I did. I had checked into an adult motel the night before and booked for two days so I had a lot of time on my hands. The night before I had pranced...Read On

Added: 29 Jan 2013 | Category: Crossdressing | Avg Score: 4.59 | Tags: crossdressing  sissy  gay  exhibition  fetish.   | 5 Comments

libertina

A Whole New Me - Part 2

Lisa finds out what I've been up to

I had just finished cleaning up in the bathroom. A spontaneous encounter with my best friend whilst wearing my girlfriend’s thong had left me a bit of a mess and as for the thong... well I guess I’d need to find something new. Fully cleaned up, I ran naked into our bedroom and started looking through Lisa’s drawers for a new pair of panties. I wasn’t sure how I’d explain my change to her...Read On

Added: 30 May 2012 | Category: Crossdressing | Avg Score: 4.93 | Tags: strapon  anal  crossdressing  panties  bi  bisexual  role reversal   | 3 Comments

trinitytowers

The Feminisation of Michael. - Chapter 6

The Feminisation of Michael. Chapter 6 The taxi dropped me off at a top hotel in London.  I checked in as Miss Michaela Wilson. My new name! I had credit cards and bank account details sorted out when I was in hospital so had a purse full of plastic! A bit like I now had a bra full as well! After the porter had left me alone in my suite of rooms I just collapsed onto my bed. ...Read On

Added: 16 Mar 2010 | Category: Crossdressing | Avg Score: 4.71 | Tags: | 3 Comments

Teresab

Christmas At The Salon

Fun for everyone at Susans beauty school...

Back in October I introduced my friend Susan to boys that wanted to be girls for her beauty school.They would come in for help with their hair and makeup and her students could practice on them.Everyone had a ball and it worked out very well. Soon the girls realized that this was a dream come true for the boys and became more demanding of them.Keeping the place clean was just one of their...Read On

Added: 29 Dec 2008 | Category: Crossdressing | Avg Score: 4.19 | Tags: crossdressing   | 1 Comment