Shemale Surprise Stories

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Vacation Swap

by LotsToShare on Jul 6, 2020
Group Sex

It was the sixth day of a ten day family vacation with our two kids at our favorite resort in Cancun and we were both pretty revved up, sexually. Vacations do that to you. The stress-free nature of being away from all responsibilities, seeing each other in very little clothing, not to mention the bevy of sexy bodies on display, inevitably leads to heightened...

Sissification 101: Ch. 04

by silkstockingslover on Jul 14, 2020
Transgender & Crossdressers

Sissification 101 Ch 04 Summary: Eric sucks his first BBC in a threesome with Joan. Thanks to Eric who requested and helped plot this lengthy story. Recap so far: Sissification 101 tells the story of Eric, a mid-30s Asian, who has been hiding his sissy side curiosity for years until he is caught in pantyhose watching hypno-sissy porn by his...

Highwaymen Ch. 13

by hardtaskmaster on Sep 13, 2017
Novels and Novellas

It was well past sunrise when Terence awoke. He lay with his eyes still closed. Already he could feel the warmth of the sun as it filtered between the leaves and branches overhead, and against his side the warmth of the young woman, his companion. He mused how good it was to wake with her at his side. In such a very few nights it had become a habit he would...

The Hermaphrodite's Curse Ch. 31

by Cleophila on Sep 13, 2017
Novels and Novellas

PART FIVE - MOUNT IDA - 2 - "Wait," Gabe, confused, demanded clarification, "You're saying that Robert White, the eminent academic expert in classical mythology, the author of Love's Children; and the transgender woman shot with an arrow at the National Gallery, the one who left the symbol on the wall, are the same person?!" "Don't sound so surprised," Ge...

A Replacement for Susan Ch. 03

by petertowers on Sep 19, 2017
Erotic Couplings

Just as Mary dropped her bomb shell, I got a text from Diane asking if I could meet her at the café next to the conservatoire where she attends an evening class. I've got to say it was a case of perfect timing as something about the way Mrs Summers had made her magnanimous offer had set alarm bells ringing in my head. I was actually glad for a chance to figu...

Kitty Gets Fucked

by kittenxoxo on Sep 19, 2017
Group Sex

My name is Kitty and I'm an 18 year old student with a killer body and an insatiable lust for sex! I live with three older boys, which some people think is weird but I love it - all the attention excites me! My boys (as I like to call them; their real names are John, James, and Chris) have to put up with a lot living with me because I just love to tease. I...

The Present Situation Ch. 02

by Maturestud2015 on Sep 14, 2017
Loving Wives

The next morning we had to pack and leave St. Louis, work was beckoning tomorrow. After our showers Dawn was packing her new clothes and dropped her robe to get ready. My eyes surveyed the wonderful treat and I marveled at how lucky I was to be married to her. I reached out to playfully rub her tits. Dawn slapped my hand and moved away saying we had to hurry...

The Return

by Goldeniangel on Sep 13, 2017
Erotic Couplings

Author's Note: This is for RedShftAway who wrote to me in January from Iraq, requesting my return. I was touched and I wanted to write something for the soldiers that I now know are reading my work. Since I have never been a soldier, nor the girlfriend of a soldier, this is all purely from my imagination. I'm sure I got some details wrong, and for that I apo...

Bare Back Rider

by Ashson on Sep 26, 2017
Erotic Couplings

I was just out on a random patrol when I got a call for a neighbour's dispute along one of the back roads leading out of town. You know the type of road, wanders out of town and into the bush, not going anywhere in particular. Turned up at the neighbours to find an old guy yelling at the mother of a teenager, threatening mayhem and murder, with the mother ye...

Just a Couple of Licks

by WadeWilson88 on Sep 12, 2017
Mature

Being bored at work sucks. But at least I have my co-worker here to keep me company. We work at a portrait studio, a big name portrait studio. So far I had a few customers today, but that's about it. I really don't mind when it's slow, because I get paid by the hour. Since there was nothing else on the books I just kicked back in the office with Lizzy. Lizz...