Crossdresser First Time Stories

351,031 results
Orientation
Length
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Infinite Scroll

Letters to Cassie: Pam and John

by luvz2x on Sep 16, 2017
Interracial Love

About a week after I published my story about Kathy, Pat and John e-mailed me about their fantasy. There's a whole other story coming out of this little adventure... you'll read about it in the future... but here's their adventure. It's a Duzzie! Letters to Cassie: Part 1- Pat Begins... My name is Pat. I'm a 45 year old middle school mentor teacher in Orc...

Celebrity Summer School Ch. 02

by DarkSwordsmanReturns on Mar 10, 2020
Celebrities & Fan Fiction

Monday, June 1st, 2020 Loud, orgasmic cries carried through the halls of Sofia Vergara Summer School for Girls' student dormitories; the impassioned coos, as they did every term-time evening, providing campus security with enough jerk off material to spank themselves into a coma. The student dorms at SVSSG were much like those at any other academic institu...

A Very Public Perversion Pt. 01

by Herbertson on Jan 21, 2020
First Time

Sheena was classed by society as a dirty little tart. She had ideas about life that deviated from what was deemed to be normal in polite society. She had been brought up in a loving, caring and wealthy middle class family. But she had rejected their morals and expectations. Now she lived alone in a squat in the centre of town. Sheena had water, electrici...

The Poker Party Ch. 04

by tv46 on Sep 26, 2017
Group Sex

Lucy stepped out onto the glassed-in lanai of the guest suite. It overlooked the 18th green, and she could see David and his buddies approaching the green. They looked to be in good spirits, but Lucy could not discern if they knew what was waiting for them. She wondered if David had completed his mission. She tried waving to the guys as they walked onto the...

Suzette's Secret Love Life

by walterio on Sep 12, 2017
Anal

PRELUDE Suzette Mica Du Bois was lying on her back on a massage table. Her lovely shapely body was barely covered with a towel. The towel was long enough to modestly cover her breasts and her pubes. This was her third trip to the Paris spa this week and she anxiously awaited her masseur. Her excitement grew as she anticipated the day's activities. The nippl...

Patricia

by Victor Field on Sep 12, 2017
Transsexuals & Crossdressers

This is inspired by, and sort of about, the incredibly beautiful Brazilian transsexual porn actress Patricia Araujo - Machado is her real last name (though in this story she doesn't do porn these days a la Elisha Cuthbert in the underrated "The Girl Next Door," the only actual similarity - no proms or award robberies here!). Apart from her, none of the chara...

Getting Down at Brown

by ReedRichards on Sep 11, 2017
Romance

I had just gotten my pants back up when Jeff and his girlfriend, MaryEllen, walked into the dorm room Jeff and I shared. Jeff went straight in to the bathroom, when MaryEllen smirked at me and said, "If you're going to jack off in this room, maybe you at least ought to do it in the bathroom." I was busted. I didn't realize it for a second, but a deep breath...

Amber's Enslavement Ch. 06

by dweaver999 on Sep 16, 2017
Sci-Fi & Fantasy

Chapter 6 First Lessons "Master, it's time to wake up, Master." Justilia gently shook Inclon as he sat face down at his desk, scrolls unrolled beneath his head. Inclon's eyes opened. He was suddenly aware of hunger pains and a dry mouth. He pushed himself up in his chair and rubbed his face. Sometime during the night someone, most likely Justilia, had ca...

Back on My Feet Again

by holliday1960 on Sep 16, 2017
Romance

Author's warning: This story explores a dark subject; mental disorders. It briefly suggests the exploitation of people with mental challenges by the medical profession, and society. It's a relatively short exploration into the mind of someone with Post-Traumatic Stress Disorder. I've taken every precaution in avoiding obvious triggers, but with this disorde...

Marriage Shuffle

by imhapless on Sep 13, 2017
Loving Wives

Rachel and I had been married for four years before we moved from Illinois to Virginia. We were college sweethearts for two years, seemed compatible in every way – including sexually – and got married several months after we graduated. We're fairly normal looking people, although both in much better physical shape than the average American, even the average...