Transsexuals & Crossdressers Stories

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Sheila’s Escapade #137

by Sheila_TSSub on Sep 16, 2017
Transsexuals & Crossdressers

My beautiful Mistress is out of town for a long weekend. This is ostensible a semi-annual buying trip for one of the stores she represents, but in this day and time such trips have become arcane. I've always believed her real motive is to spend time with her friend Jan. The very thought of her between Jan's legs and lapping away at Jan's pussy made my clitty...

A Different Kind of Weather

by Adrian Leverkuhn on Sep 16, 2017
Transsexuals & Crossdressers

He's standing at the water cooler, listening to the usual banter. Things like 'which girl in accounting has the best ta-tas?' or 'If you need a date with someone really easy, try Mona over in shipping...Mona will have you moanin' in no time...' He tried to smile, tried to see the humor in his co-workers' backwards banter, but it was difficult. In the first p...

It was Supposed to be a Quickie

by lovers1 on Sep 16, 2017
Transsexuals & Crossdressers

I was in a strange place, around nobody I knew, and feeling the distance. I sat at the outside bar on the beach at a popular club in Key West. My name is Jenny and I was here for a week at least, escaping. It was a beautiful night and even though I was suffering lonely thoughts and feeling like an outsider I could appreciate where I was at and the beauty su...

Sydian Ch. 01-08

by sydian on Sep 16, 2017
Transsexuals & Crossdressers

Sydian/Chapter 1/Unique Unique. The only way to describe her. She had invented herself to be arresting. She liked stopping traffic. She was not quite 5' 5". This meant that in her favorite stilettos—stilettos, only—she was 5-9, maybe 5-10. She weighed a compact 140 lbs—"thick," as the youngsters put it. But this was all muscle—she was cut—sculpted; not over...

Kasey's Confession Ch. 18

by KaseyLegs on Sep 14, 2017
Transsexuals & Crossdressers

I got dressed up in a miniskirt, thong panties, my pink five inch heels with laces that wrapped around my foot and up around my ankle. There was my usual pink t-shirt to go with it, and I also put on some light makeup consisting of mascara, eye-liner and a very subtle shade of lipstick. It was getting better at putting on makeup, and my troubles with being a...

Kasey's Confession Ch. 13

by KaseyLegs on Sep 14, 2017
Transsexuals & Crossdressers

"Oh my goodness," was the first thing Dr. Dietz said when I walked into her office and she first laid eyes on me. "How terrible it must be for you, honey, to be trapped inside a man's body!" "Yes ma'am." "Mr. Smith tells me you are very shy when it comes to talking to people, especially women, but I have his full report on you already. The only thing still...

Sofi, Bottom Boi Ch. 02 - Daddy's Gurl

by DoxyTrainer on Jul 31, 2018
Transsexuals & Crossdressers

Conjunto music filled the apartment from the driveway next door. It stumbled in through the half-open window, notes falling flat on the floor. That's the price you pay in SA for cheap rent inside the city limits. Button accordions lurked everywhere, in closets, on the radio, around people's necks, and sometimes they marched into restaurants and extorted doll...

Sofi, Bottom Boi Ch. 03 - The Truth Hurts

by DoxyTrainer on Jul 31, 2018
Transsexuals & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** Every relationship has a honeymoon period, even a relationship as unquestionably unusual as Sofia and I. I'd always thought of myself as unflinchingly straight, a real ladies man. I can tell when another man is handsome, and it doesn't bother me to acknowledge it. I don't have to...

Pillow Talk Ch. 07

by MicheleNylons on Sep 11, 2018
Transsexuals & Crossdressers

Pillow Talk By Michele Nylons Chapter Seven – CBGB Michelle Clooney met with Linda Gordon in her pokey flat down at Hunts Point but told her nothing what had happened at the Pine Barrens. Far from it; the way Michelle told it, she had met Nicky ‘The Wop’ and Vinnie Boccia at a coffeehouse in Little Italy and they had hatched their scheme there. “So you...

High School Reunion

by phoenixcinders on Sep 18, 2018
Transsexuals & Crossdressers

All characters are over the age of 18. *** Finally walking off the plane from my first class seat on a Thursday evening. It feels good to be home. I'm back in town for my 10-year high school reunion. This time I'm going to be the one everyone's jealous of. I've got the perfect job, making more money than I know what to do with. Well... being an accountant...