Ann seemed pretty happy with the party she threw for her birthday. People were mingling in her garden, talking and laughing while they fought summer's heat with beer. I didn't know many of Ann's friends - in fact, the only face I recognized at the party was her own, but I knew she kept company with mostly single people and any of her gatherings resembled mor...
I was now totally dressed, in 4" open toed sandals, with black seamed fully fashioned stockings attached to the garters of a tight fitting waist cincher, wearing an underwire long-line support bra with "Pad inserts" that pushed to give me a cleavage. My makeup was incredible, with blue eye shadow, long eyelashes, and heaps of lipstick, and I was wearing a...
I am a "Closet-Crossdresser" - something my wife would not accept, but a secret I indulge in whenever she is out of the house for a while. This is my story of how a beautiful older lady, who had a "fetish" for lipstick, nylons, high heels, and lingerie, introduced me to the pleasures. It was the late-1980's, we had just moved from a small town in the UK, t...
Chapter Two – Wren Division Ho! The four Leading Recruits were hungover and hungry and in the grey dawn and cold bleak light of day they weren't sure that their prank was really worth it. They entered the cabin and found the four 'Wrens' stood at attention and immediately began to break down in laughter. "Of my fucking god you guys look stupid!" Jean Burge...
After losses to Tommi, Jaimie and Dani, it didn't take a genius to realize that I had become the defacto jobber of the Crossdressing Sexfight League (CXSFL). There wasn't a cock among them that hadn't been in my mouth or ass at some point and if we had kept standings, I would have been in dead last place. Unless I wanted to accept my jobber role within the l...
After my sexcapades in Amsterdam I had such a thrill from playing dressup and just getting fucked silly. Summertime came around and I was on vacation and still in Paris. So I decided to do something similar to my weekend in Amsterdam. But where? I decided to go to Spain. I got a train ticket to Sevilla and decided I would do the same thing I did in Amsterdam...
Martin walked down the walkway his heels clicking loudly as he moved quickly away from the house. He felt almost naked walking in the bikini that Leanne had seen fit for him to wear out today. Wearing 6" spiked heel sandals and his hair in curlers covered with a large white scarf tied under his chin, he walked with his head slightly bowed as he thought about...
My first time with another man was when I was 18 back in the late 80's. My girlfriend was a virgin and the farthest we went was kissing and rubbing together with our clothes on. I would take my dirty magazines out behind where we lived in the woods and take off all my clothes and masturbate. I was out there every day there was nice weather masturbating and...
This is a continuation of my True Stories series, where I tell my readers about my real life adventures as a part time Transvestite. In this instalment I will tell you about my most recent encounter; my first encounter for some time, and also for me a milestone; my first time out and about dressed as a Transvestite. This is the story of my latest encounter,...
Introduction For those of you who only read fiction I suggest that you go directly to my autobiographical sex stories contained later on in this essay; but what I thought I would like to do is to take a break form my usual 'physically forced' and 'caught with consequences' Transvestite sex stories and write some of my musings about Transvestism and share wi...