Transvestite Stories

1,024 results
Orientation
Length
Source
Infinite Scroll

When Sara Met Bob Ch. 02

by yellowfrog on Sep 14, 2017
Fetish

PART II: Bob learns to sip Sara's pee and Sara explores his prostate. * Our first night together was one of unblemished bliss. Spooning Bob all night, I felt his breathing and his heartbeat. With the first rays of morning I knew we both had to rise and shine for the day ahead of us. Neither wanted to get up, especially not me. On the other hand, my bladder...

La Contessa Ch. 01

by SlaveNano on Sep 25, 2018
BDSM

La Contessa The most decadent city... The most perverted of mistresses... Renowned for her cruelty and the bizarre sexual tasks her household servants perform for her, La Contessa's reputation is well established. And Venice of the eighteenth century has degenerated into a decadent and lascivious city, the perfect backdrop for her perverted games. This i...

Kinky Bride Confessions Ch. 11

by yano on Sep 16, 2017
Interracial Love

So my girlfriend Emma had just been married in her first porno wedding for the Kinky Brides Group and now ends her story with a shocking honeymoon. "Returning to the altar we found the bed covered in a white satin sheet and climbed on to it. We were to begin in the traditional position, my legs wide apart as I watched Jay straddle me and then point ten inc...

Adventures in Nemesisland Ch. 15

by SlaveNano on Nov 15, 2017
BDSM

Kim was left with her own thoughts for a while as the pagan priestess and her maid left the dungeon with her slave, Nano or the black cat as Kim thought of him. Kim's head was a whirlwind of thoughts and emotions. She still hadn't really had time to absorb fully the significance of the second part of the black cat's tale. It wasn't that she didn't believe it...

Desiree's Cock Quest

by desireethtttv on Sep 16, 2017
Transsexuals & Crossdressers

It had only been a month or so since Suzie discovered my secret stash of letters between my alter ego Desiree and another transvestite. In them she read how we both love to suck big black cocks and our bragging on the longest cock we'd ever sucked. Needless to say, it put quite the strain on our marriage. With the fact my love for long hard cocks was all o...

A Transvestite Odyssey

by lynntg0444 on Mar 18, 2020
Transgender & Crossdressers

I like playing a girl, but it's complicated. I have always been more attracted to women than men, and had many relationships with women including two marriages. As a young man I had several sexual experiences where I played a feminine role. Wearing girly things was a real turn-on for me, and it seemed to make it less queer for us both. I would later learn th...

Lady In The House Ch. 13

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

I awoke in my cell the next morning unaware of the terrible fate that had befallen my sister Angie. I knew that Steve had sent his henchman Danny to do something to her in retribution for my recalcitrance but I didn't know exactly what that evil bastard Steve was capable of. I lay there shivering with dread hoping that Danny had just given Angie a warning,...

The Devil You Know Ch. 02

by MicheleNylons on Sep 12, 2017
Transsexuals & Crossdressers

Brian Davies sat at his desk struggling with his conscience as he remembered what had occurred the previous evening at Mike Harris' house. He didn't think of Mike as a man in drag; he thought of Mike as the uber-sexy transvestite Michele Nylons. But the outcome of his visit to Michele's had not turned out as he planned it; he had taken liberties with Michele...

Halloween Transvestite Stripper

by kristycross on Dec 2, 2019
Transgender & Crossdressers

It was Halloween Night 2018 and of course Kristy was going out to party! A local LGBT Club was having its party and I had the hottest outfit to wear dressed as a Stripper! From the Red Basque, Thong, Garter and Hose to the Black lace-up over the knee Boots and Sheer white Mini-skirt, I was looking as Hot as I felt! The 30 minute drive was un-eventful and t...

Lady In The House Ch. 14

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

After the warden left my cell my mind was racing. Why were they bringing my sister here to visit? How was I going to remove my makeup and nailpolish? What was I going to do about my semen-stained clothing? I heard the keys rattle in the lock of my cell door and Steve strolled in. "Well Michele it look's like you are starting to behave. The warden seemed ha...