Surprise Shemale Stories

136,276 results
Orientation
Length
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Infinite Scroll

Halloween Party Surprise

by m_storyman_x on Sep 25, 2017
Group Sex

I have always loved parties, even though I never seem to get invited to too many. I also love holidays, and one of my favorites has become Halloween. When I was a bit younger and raising a family it was always fun to dress up and take the kids out trick-or-treating. We usually made interesting costumes for them and tried to be innovative in ours as well. One...

Three Square Meals Ch. 73

by Tefler on Sep 25, 2017
Sci-Fi & Fantasy

Matriarch Tsarra Perfaren nibbled apprehensively on her thumbnail as she stared at the holo-map projection of House Perfaren territory. Biting her nails was an unfortunate new nervous habit she'd acquired, but considering the stress she was under, such weakness was understandable. She had bags under her eyes from lack of sleep, and her exhausted dark green o...

Mom's Punishment

by embarrassedboi29 on Dec 2, 2020
Exhibitionist & Voyeur

**Public** Here I am again, sitting in the principals office for the 3rd time this month. My mom is going to kill me but I don't really care. What's the worst she can do? Yell at me? My teacher was being a bitch and so I told her so. "Hello, Mrs. Michael? Yes this is the school principal. I am calling because we have your son, Jared, in our office again...

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Patti Cake Ch. 11

by betamale08 on Jul 31, 2019
Transgender & Crossdressers

Patti drove us up the main house in one of the golf carts and I was so nervous, I was shaking –and Patti noticed... Without looking as she steered the car up the winding paved walk-way, she put her hand on my bare knee, in a silent way of trying to reassure me that everything would be okay –but of course, I wasn't convinced as I wondered then for the first t...

A Day in Gotham - Batgirl Begins 03

by duke1951 on Sep 19, 2017
Celebrities & Fan Fiction

((Authors Note -- here's the third and final episode of my Batgirl Begins trilogy. I hope you enjoy reading it as much as I've enjoyed writing about my favourite super-heroine. As with all such series, it's probably best to read episodes one and two first, but if you can't wait here's a very, very brief summary of events so far. Batgirl (Barbara Gordon) has...

Visual Pleasures

by Many Feathers on Sep 1, 2017
Group Sex

Authors note: There is a very brief bit of bi-sexuality between two of the male characters in this story, towards the end. I've included this at the request of several individuals (mostly women in fact) who've asked that the next time I did a story similar to this, I would do so. It is for them that I have. I would ask that if this isn't your cup of tea, bri...

Miss Ellen

by icedragonmo3 on Dec 2, 2019
Transgender & Crossdressers

Disclaimer: All persons depicted engaging in fornication of any kind are over the age of consent. This story contains an overly tall, hermaphrodite BBW, lactation, feminization, and strong themes of servitude and devotion... If any of that isn't your thing, that's why I wrote a disclaimer. ****** I grinned as Ellen explained what exactly I didn't understan...

Peppermint Pussy-Fire in the Hole Pt. 02

by ditto79 on Sep 14, 2017
Text With Audio

As was posted earlier . . . Sir gave a shopping list to his slave to purchase items for that evening's training session. One of the items on the list was pure peppermint oil extract. She had never heard of peppermint oil, only those white and red candy disks and she never really cared for the hot taste. As for a liquid peppermint, she imagined it was going t...

"Castaways"

by kwill81 on Dec 6, 2008
Swinging

Kelly stood on the bow of the ship. She worshiped the sun letting it warm her tanned skin. She ran her hand through her long dark brown hair and opened her eyes. She blushed when she saw Kevin the stud staring at her and she hoped she didn't look silly. She turned her athletic body away and almost ran away. She heard him laugh behind her. Whew, way to go Kel...

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This Fucking Economy

by fiestyfeast on Aug 7, 2019
Cheating Spouses

My wife Kayla and I came from meager backgrounds. We met in college, each of us the first from our families to attend. We graduated with degrees in our respective fields, and soon each managed to obtain employment in them. We spent most of our savings on the wedding since our families were unable to help much with the expense, and we signed a rent-to-own con...

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