Trans Girlfriend Stories

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Infinite Scroll

Sissy Pills Pt. 02

by Sissyhalo1 on Jul 6, 2020
Transgender & Crossdressers

There's nothing like waking up like this. This being after being fucked. Not fucked but riding a dildo until you have a sissygasm. And yet that's not the first thing in my brain waking up. It's the cum. It's that eating my own cum. And really feeling this need sort of burned in my brain from the semen and the pills. I really, really want to suck a co...

Story Tags and Searches

by wishfulthinking on Sep 18, 2017
How To

I read this really great story a couple of months ago, but I can't find it now. I'm sure it had black/blue and/or orchid in the user name, and it was about a girl and her boyfriend at her boyfriend's place for a party, and she ends up sleeping with his cute dad. (If any one knows the story I'm talking about, please PM me! Seriously) I've searched: boyfriend...

In Sheep's Clothing

by Cyberweasel89 on Oct 24, 2020
BDSM

Clarabelle "Clara" Bullock was 24 years old and a professor of art at Florida University. Living in an apartment in the suburban college town, she'd only had a few lovers, never had sex, and had few friends outside of some of her fellow faculty at the college. She had one secret, though... Clara had always dreamed of BDSM. She'd read novels, done r...

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Mom's in Town Ch. 27

by 1sfshermale on Aug 7, 2018
Transsexuals & Crossdressers

Jennifer thought... less than 24 hours ago she would have never guessed that she would have fucked her roommate in the ass, been sucked off a couple of times, fucked her roommate's mother and finally cum all over her roommates mother's face. Christine, her MTF daughter Brianna, and Brianna's trans university roommate Jennifer had their showers, shared make-...

Tranny Night Out and One Kinky Session

by BmthAdmirer on Sep 16, 2017
Transsexuals & Crossdressers

Guess I should start by explaining myself, as a young guy I always knew I was not the same as a lot of my friends and enemies for that matter, girls had no interest in me at all apart from ones who were long term friends. I knew something was wrong but never worked out what it was till one evening whilst dating a girl named Becky I had met on an online dati...

Trans-itioning to a New World

by penbeatsword on Sep 16, 2017
Transsexuals & Crossdressers

I always thought I was a fairly typical guy. I'm a fireman, in a relationship with Melinda, my high school sweetheart. A short curvy blond with chin-length hair and brown eyes. Went to the local community college. Had a chance to study abroad in my junior year, so after struggling through a Spanish immersion class, I spent a semester in Argentina. While in...

Genital Obsession

by AlinaX on Jul 31, 2019
Humor & Satire

"Hi!" I said cheerfully. "I'm Ali, a gorgeous blonde with 42DD breasts and legs that won't quit." Fiona gave me a baleful glare. "What are you - the narrator?" "As it happens, yes," I agreed, unfazed. "What gave it away?" "The fact that we're suddenly in some weird fantasy world where your hair is no longer Mediterranean-dark and your breasts are twice th...

My Life Pt. 05: Paul

by ShyTammy on Sep 26, 2017
Transsexuals & Crossdressers

My Mom and Paul Those of you who have been reading my stories know that I have a fascination with my Mom and her sexuality. My Mom is a gorgeous Italian woman. She is very voluptuous with big breasts and nice hips. She has long curly dark hair like mine and hazel eyes. Her skin is the loveliest olive shade I have ever seen on a human being, though I may be...

Transgirl SPH by Friend

by Hyperdebut on Aug 13, 2019
Fetish

All characters in this story are over the age of 18 and consenting. *~* I was sat home, alone in bed watching porn on my tablet computer. It was around 2pm on a lazy Saturday afternoon in July. My curtains were drawn shut but the window was open, allowing a light breeze into the otherwise stuffy room. My pink flowery curtains lightly blew as I scrolled thr...

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...