Shemale Girlfriend Stories

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Kinky Bride Confessions Ch. 11

by yano on Sep 16, 2017
Interracial Love

So my girlfriend Emma had just been married in her first porno wedding for the Kinky Brides Group and now ends her story with a shocking honeymoon. "Returning to the altar we found the bed covered in a white satin sheet and climbed on to it. We were to begin in the traditional position, my legs wide apart as I watched Jay straddle me and then point ten inc...

When Sara Met Bob Ch. 04

by yellowfrog on Sep 14, 2017
Fetish

PART IV: Sara sculpts Bob's lovely penis Days turned to weeks, weeks turned to months and Sara derived ever-growing joys from milking Bob's prostate. The implanted micro-devices gave Sara the ability to massage his prostate remotely, be it from a distance in the same room, to the other end of the bar at the shemales saloon they frequented often, and even ov...

My Girlfriend - A Shemale

by ARandomGuy on Apr 22, 2025

(hello everyone, who is reading this. so first thing, first. I'm not a first-time writer but my other account is gone. so this is my first story from this account. 2nd thing, I'm not the kind of guy who loves to jump on straight to fucking. so yeah, the story is gonna take some build-up but is not that long that you'll feel sleeping is better than this story...

Shemale Surprise.

by ceb35 on Sep 16, 2017
Sci-Fi & Fantasy

As a single woman I do spend quite a bit of time enjoying porn flicks on my Kindle Fire. But I never imagined that anything I watched would ever happen to me. But it did! My girlfriends and I often go out to one of several bars nearby my home. We go as a group just to hand out and talk and occasionally meet new people. Some are nice and some are just compan...

My Girlfriend's Idea

by thinguynew on Jul 10, 2019
Fetish

As the keyboard player I occasionally came into the studio to mix sessions when no real engineers were available. This session had started late but was easy. Tweaking a backing track for a nightclub performance. The client sat on the standard studio couch at the back of the room, her long legs stretched out on the small coffee table. Clarisse was a coffee co...

Shemale Funpark

by patrickstar1212 on Apr 22, 2025

You go to a Funpark in Miami, Florida where you are supposed to meet your Friends. You really like them and drove all the way out here just for them. Right as you enter the Funpark to get to the meeting point, your Friends call you in a groupchat. They tell you that their Car broke down a long time ago but their Phones had no Battery and they were in the mid...

Shemale Adventure Ch. 1

by girlboybootsie on Aug 18, 2017
Fetish

You: early 20's, tall boyish good looks with a lean and muscular body. Dressed in tight leather pants, from behind your tight buns are revealed by the shiny black leather, as are your cock and balls from the front. You are wearing black leather boots and a denim shirt that refuses to hide your strong broad shoulders. Me: early 30's, tall, blue eyed, consid...

Girlfriend's Dream Comes True

by add1cted on Sep 17, 2017
Group Sex

It's been four years since I first met my girlfriend - Annie. I fell in love with her straight away. She was all that I've dreamed about before. She is 175 cm tall, cute face with black hair, big tits which she likes to show off and a nice round ass... and a big pervert also. Her sex imagination is beyond anything I've seen in porn movies or read in stories...

Shemale Tales: The Christmas Party

by silkstockingslover on Sep 2, 2017
Illustrated

Summary: Young woman discovers the perfect man... a woman with a dick. Note 1: This is a Christmas 2016 Contest Story so please vote. Note 2: Thanks to TexBeethoven, Robert, Dave, and Wayne for editing. Shemale Tales: The Christmas Party I'd been working at the firm for only a couple of weeks and originally wasn't planning on attending the staff Christ...

Sally: His Perfect Shemale Partner Ch. 1

by PunkFan on Sep 16, 2017
Fetish

I am in senior year of school and anyone who has been to school at 18 will know it is not a pleasant time to be working when your friends are all out drinking and enjoying themselves but I needed to go back to school to go the university I wanted to go to. I am a tall fairly muscular straight guy who has had a few sexual experiences before this chapter in my...