Trans Girlfriend Stories

57,006 results
Orientation
Length
Source
Infinite Scroll

Auburn Mistress Ch. 01

by ukmaleslave on Sep 18, 2017
BDSM

Where do I start, well I guess with me, I’m 26 in a normal job with a girlfriend. Seems as my job involves me spending a bit of time on the net it was no wonder that my mind began to look toward other things, one of those things was bondage, holy shit not the serious stuff just playing. Anyway my other job is customer facing and you see all sorts, and to ge...

CBT Files Ep. 01

by rick_oh on Sep 13, 2017
BDSM

Suzie smiled brightly in anticipation. She always enjoyed donning a naughty nurse uniform and performing her version of cock and ball domination. This time the guy who was to receive her attentions was her new boyfriend, Bradley. Suzie was in the process of "taming" him, as she called it. As soon as Bradley was in her apartment, she commanded him to strip....

Laura's Couch

by AndreaJordan on Sep 26, 2017
BDSM

Laura stretched out her long slim legs until her stripy woolly socks pushed up against Jack's legs. At first Jack slid further up the sofa, but Laura's feet caught up with him and once again playfully kicked him. With no room left to move, he paused the movie and looked over at his giggling girlfriend. "Am I in your way?" he asked, as he used his cuffed han...

Bethany's Secret Ch. 1

by Wannabe Chick on Sep 18, 2017
Transsexuals & Crossdressers

-1- By the time my senior year of high school rolled around, I was 18 years old and I’d never had a girlfriend. This fact always bugged me because I knew I was good-looking, funny, and popular, but I still couldn’t get girls. The reason was simple shyness. I was terrible at talking to girls who I was interested in dating. I would open my mouth and sputter o...

Discovering a Domme

by Moxon4 on Sep 12, 2017
BDSM

He drove home from a hard day at work, he had worked 12 hours, and was wanting nothing more than to go home, take a shower, and then go to sleep. He got home, dropping his keys on the kitchen counter, took off his sport coat and put it on a chair and continued to drop his clothes in a path to the bathroom, with his shoes sitting neatly outside the door. He g...

Taking What I Can't Give Back

by EuropeJenn on Sep 12, 2017
First Time

This is a true story; in classic form names are changed, except mine. I also glossed over some of the more mundane details. I had always wanted to take someone's virginity but I didn't think that I would ever get the chance. Actually that isn't quite true, when I was 15 I lost my own virginity to my then boyfriend who was a virgin himself. It was a disappo...

Father Uses Huge Asset Ch. 16

by acdd123 on Sep 26, 2017
Mature

He smiled, Richard had his hands in Sally's long shiny hair as they sat in his office kissing. Sally had a business suit on which included the shortest tightest micro mini skirt Richard had ever seen as part of a "business suit." Her long tanned legs were crossed and she smiled innocently at him: "How good a fuck was your son's new girlfriend" she asked. "...

Mrs. Anderson Plans a Vacation

by Magna12 on Sep 12, 2017
Exhibitionist & Voyeur

My sister's brother-in-law is in Mrs. Anderson's English language class for foreign students. He is the brother of my sister's husband. Dorian recently moved to America from his home in Greece, and he's now enrolled in English classes at the local university. His teacher is Mrs. Anderson, who is in her late forties. Mrs. Anderson has a very appealing look...

Timmy Gets a Girl

by Bakeboss on Sep 14, 2017
Transsexuals & Crossdressers

The day my life changed was a day of infamy and one I shall never forget. Although it happened years ago, every detail was fresh in my memory as though it happened yesterday. Almost daily, it replayed in my head as if my mind enjoyed torturing me. Freshman year of high school and although I'd discovered girls I was far too shy to do anything about it but dr...

Under Surveillance Ch. 01

by denva on Sep 17, 2017
Loving Wives

I got home late from work that Friday and I ran upstairs to see what my wife, Lyn was up to. She was in the shower getting ready to go out with friends. It's a once a month thing they do. As I walked pass the bathroom I yelled out, " Hun, I am home." "Hi baby, I will be out in few minutes." She replied. The telephone rang and it was Mum. She usually phones...