Shemale Girlfriend Stories

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Girlfriend's Shemale Surprise

by Artvan1 on Sep 24, 2020
Transsexual

As Carter finished unpacking after dinner, he couldn't help but smile. His last summer before having responsibilities would be spent in the beautiful home belonging to his girlfriend's parents. Carter and Chloe had only been dating for a few months but were both entirely consumed in the early parts of their relationship. From hand holding to mini-golf the yo...

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The Making of an Angel Pt. 01

by AngelLawrence on Jul 29, 2019
Transgender & Crossdressers

This is part biography and part reminiscing. I've changed names to protect people's identities and skewed some of the locations to make it difficult for people to be identified. All persons are over the age of 18 at the time of what happened. I wish I was still 18... I would have had my surgery much earlier! ***** My name is Angel Lawrence and I'm a 48 ye...

I Meet a Well Endowed Shemale Milf Online

by Jamesw324 on Sep 13, 2018
Transsexual

I let out a long sigh as my computer began to boot up, "Well I guess I will check my messages again." Hello there my name is Alex and I am a high school graduate living at my moms house to take a break year. This year I need to find work and hopefully a girlfriend. It was at the start of this break when I stumbled upon this sight called: Shemale me...

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Blossoming Shemale Ch. 02

by TheTitLover on Sep 25, 2017
Transsexuals & Crossdressers

This is inspired by:http://www.literotica.com/s/reluctant-shemale tawnysuede's Reluctant Shemale if you enjoyed it, I hope you'll enjoy this series. * * * My name was James. It was, before everything that happened, anyway. I'd come from pretty good stock, as the snooty, upper class would likely say. I guess I still did, although it would take a DNA test to...

Backside Foremost

by pikapache on Sep 29, 2019
Transsexual

In a single moment, overnight, the world changed, men are now cuntboys and women are now dickgirls. Within an instant, gender roles have been completely revamped and it is difficult to see just how the world will adjust. In the morning everyone will wake up confused and in a panic. The whole world has been turned inside-out, topsy-turvy, inverse to how it on...

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The Sexiest Shemales Ch. 02

by cleanly_shaven on Sep 13, 2017
Transsexuals & Crossdressers

Holly and I didn't want to waste our day so got up and got ourselves in the shower. We stripped off our g-strings that we were still wearing from our sex fest and turned on the hot water. We always shower together. Sometimes we will fuck each other in there or suck each other off but we just had sex so we just soaped up each other's bodies and cleaned the cu...

Amanda and Me Ch. 01

by Tallnhard1 on Sep 25, 2017
Transsexuals & Crossdressers

I walked in the door of my one bedroom apartment and headed straight for the computer. Lately it seemed like I had the same boring routine everyday: get up early, work all day at my stressful IT job, go straight to the computer when I get home to look at porn and masterbate, then eat dinner and go to bed early. Unfortunately tonight was no exception. As I w...

Reason? Nah.

by curdles on Nov 8, 2020
Bisexual

"Oh, fuck!" she gasped as soon as my cock had slid out of her throat. She had held it there for almost a full minute, massaging my balls with her tongue all the while. We hadn't seen each other for almost a week, so our appetites rivaled those of Erysichthon of Thessaly. "I'm almost there," I said, stroking my shaft. "Open up,"...

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Alpha Gamma's Secret Ch. 2

by Wannabe Chick on Sep 11, 2017
Transsexuals & Crossdressers

-4- Molly awoke to the annoying sound of her alarm beeping. Groggily, she reached over to her night table and turned it off. It was 7:00 AM, way too early for a 19-year-old college girl to be awake, in her opinion. As she stirred, her girlfriend wiggled up against her, eager for body heat. Molly smiled and looked over at Gina – her girlfriend, lesbian lover...

The Society

by Barno on Sep 19, 2017
Transsexuals & Crossdressers

I met her during the summer. I was only nineteen and working to save some money for college. I had been raised by my grandparents who had both passed away over the past year. After the burial costs I was far from wealthy. My parents weren't around so I was on my own at a young age. I had moved a couple of towns over from where I had grown up and was living i...