Trans Girlfriend Stories

57,006 results
Orientation
Length
Source
Infinite Scroll

The Old Switcheroo

by NLO_Cliff on Sep 13, 2017
BDSM

This love started with a break up. When you're fingering your girlfriend's best friend's sopping wet pussy, and you get drunk and tell your girlfriend, it's pretty much bound to happen. But that's for another time, perhaps a prologue? Anyway, let me tell you about myself, my name is James, I'm 19, 5'4", and weigh roughly 200 lbs. I have short dark hair, bro...

Must Go To Gym More

by Falkenhayn on Aug 18, 2017
Fetish

Why is it everyone gets the urge to get thin and beautiful in the Summer? Is it the heat, the holidays, or just the fact that every girl on the street seems untouchable and out of your league? Every girl that is, unless you're lucky enough to have a girlfriend. But if you wish to keep her, you better damn well get your ass to the gym. So here I am, rolling...

The Hymen Theory Ch. 03

by seriouswriter12 on Aug 18, 2017
First Time

One month. Chris nodded absent-mindedly as he pretended to understand what Imogen was talking about the entire time their having dinner. He tried focusing, really did, but thoughts of a certain brunette with hymen issues kept on insinuating inside his head. And the unanswered question of why in the hell did a whole month pass without Sam ever mentioning the...

Watching

by Ashson on Sep 19, 2017
Exhibitionist & Voyeur

I was with Janice at the beach on the day it happened. Not that it happened to me and Janice. We were just witnesses to what went on. Very inconspicuous witnesses, I assure you. But the whole thing was quite an education for us, and a warning. You have to understand that Janice and I were a little young for our age. We knew theoretically what sex was about,...

Getting to Know Kaylee Ch. 04

by Art Martin on Sep 16, 2017
Loving Wives

Ed Bailey shifted in his chair. "So you moved in with her? When did you discover that she was slut?" "A slut? That was obvious from the start. She loves sex in great quantities as well with quality. The girl is insatiable." "I thought you said she wasn't an insane fucking machine." "I said that? I stand corrected. But to answer your question, I was madly...

Fun with the Babysitter

by scarlettshea86 on Sep 12, 2017
Group Sex

I'm sure the babysitter had some idea about the nature of our relationship. We never outright said that we were a polyamorous triad, but she knew that while all three of our children were Josh's, I had given birth to two of them and Jessica had given birth to the other. I was "mama" and Jessica was "mom" to the kids and the three of us raised them equally. P...

Lake Tahoe Test Drive Ch. 04

by Ear2Ear on Sep 25, 2017
Anal

"Buddhist, my ass," Nick murmured as he slid his cock deep in Sam's asshole, then pulled back, the pleasure on his cock head sending a chill up his spine. She barely whimpered as he fucked her ass today. He pounded her with more intensity, eliciting a polite moan. In return, he swung his hips back and forward even harder, spreading her tanned ass cheeks wide...

Black On Black Pegging: It's Hot!

by Samuelx on Sep 11, 2017
Fetish

The life of a young Black man in North America is seldom easy. However, I'd be lying if I said it wasn't worthwhile. And I owe it all to my special lady. I love my Black goddess. There, I said it. And I don't care if it makes me sound whipped, or weak, or whatever. My name is Steve Jean-Simon and I approve this message. At the time of this story, I was livin...

Matchmaking Trap Ch. 03

by SEVERUSMAX on Sep 18, 2017
Fetish

Chapter Three: Donna Donny rang the doorbell at Deanna's, thinking, well the hell is she? "It's Sunday, for Christ's sake, she is normally home, and she said that Chad fishes on Sunday mornings." Donny could not help himself. He did feel badly for poor Chad, but the lucky guy was getting to marry Deanna! Donny had little experience in sex, due to his sm...

Nurse Dominique

by darhove on Sep 17, 2017
Fetish

I hired Dominique, via Home Help online, at a premium rate since she was a qualified nurse. It was self-indulgent to pay a nurse to act as a housekeeper but I'd always been a bit of a hypochondriac, especially since I'd moved to London. Perhaps I simply missed the country air but I liked the idea of having my own medical practitioner, even if it was for just...