Cross%20dressing Stories

43,513 results
Orientation
Length
Source
Infinite Scroll

Anal Sex with Stranger on a Train 05

by SusanJillParker on Sep 19, 2017
Transsexuals & Crossdressers

Chapter 5 Peter finally meets Roberta again, the love of his life. In just a few minutes, Robert returned to the room dressed as Roberta. Giving him a sexy cross dressing show, by her feminine antics and charms, she obviously enjoyed being watched by Peter. With a shake of her head and with a flourish, as if releasing her sword in Zorro, the gay blade, sh...

Music Lessons

by literoticpalsy on Aug 17, 2017
Fetish

I hit another bad note. My voice cracked under pressure, I guess. This is the first time I'd ever taken up singing lessons. I never was interested, but my parents used to say I had potential. They felt I could do better than all of the students in my chorus classes. I couldn't wrap my head around the idea of singing as a lifelong career though. It just isn't...

Hidden Valley Pt. 04

by RiteofSpring on May 16, 2018
BDSM

As Polly Menard and her girl friends disappeared into the lobby, the mayor of Johnson took Romy's arm and escorted her back to the stage, plunking her again in the seat beside him to watch the next show in the Summer Fuck Festival. Before I had time to reflect on what the next act in this festival of sexual excess might be, the sheriff and two deputies appea...

Our First Experience with BDSM

by captaindave1 on Mar 2, 2020
BDSM

I was at work and went to make a call on my cell phone when a photo memory popped up. It was a picture of my girlfriend, Sasha, from the Halloween party in Key West, called Fantasy Fest. Fantasy Fest is a ten-day party in Key West, usually held during the last week of October. It is a place where adults gather and simply kick back not caring about the folk...

Blood Red Rose

by ooohkitty on Sep 27, 2005
Science Fiction

Three long hours she waited for him here in this dingy little bar. She hated this city and this cesspool just happened to be in the worst part of it. Looking around the room she saw people drinking. Drinking to forget, drinking to feel strong or beautiful or just drinking to be so drunk that they reach that point where nothing but the buzzing in their head i...

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Morning Wake Up

by angeleyes1965 on Sep 17, 2017
BDSM

She slowly awakened, groggily realizing there was a tongue between her ass cheeks, doing a superb job of reaming out her sensitive asshole. She was already near orgasm. She started to moan, only to feel the tongue pull out and to receive a sharp slap to her right butt cheek. "Not a sound, slut, or you'll be punished." And the tongue delved back into her dar...

Remembering Louise

by Classygloves on Sep 16, 2017
Transsexuals & Crossdressers

The only times in my life that I can say that I have ever felt free and happy were those few years between marriages when I was living single and had my own apartment. Those were the days when I felt like a complete person. Although I could not live 24/7 as a woman because of my job requirements, I still managed to live most of my social life and most of my...

Golden Girl Ch. 12

by Case21 on Oct 9, 2018
BDSM

Chapter 12: Martyrdom "Golden Girl. Step forward." It was the Duc's voice, cold and commanding. Though Dorée was victorious in her first competition at the Chateau, she would get no praise from him. He had lost his wager against her, and he was not about to mask his displeasure. But Dorée was too far gone for fear. She stepped forward, curtseyed deeply, a...

Incipiunt Vitae Novae Pt. 02: The Raptors' Nest

by bondanon on Aug 1, 2018
BDSM

Looking for Michela? Her name indeed appears here, but she really only enters the stage in part three. My original part two seemed a bit unwieldy so I split it into two more easily digestible halves, making a newly-introduced bottom entirely dependent on you to determine how long he languishes in the predicament he finds himself in at the end of this part....

The Cross-Country Calendar

by Baxter72 on Sep 14, 2017
Exhibitionist & Voyeur

Until I retired a few years ago, I had worked as an English professor at a small New England girls college. Since the college was small, all the professors also were required to coach one sport. I hated all sports, so the choice for me was hard. I didn't know or care anything about baseball, basketball, or hockey, so finally I settled on track, or cross coun...