Shemale Suprise Stories

1,639 results
Orientation
Length
Source
Infinite Scroll

A Night with a Sexy Shemale

by MajesticLVR87 on Sep 13, 2017
Transsexuals & Crossdressers

This is a true story which goes deeper into my explorations of my sexuality in my younger years many people may not have the guts to share so much about their past I don't have that problem because I have met the love of my life and plan on sharing the rest of my life with her my adventures with other partners or random partners is over I have settled down s...

The Real Deal Ch. 02

by Rob Conner on Sep 14, 2017
Loving Wives

This is the second part of a tale that features Terrance and Angela (Angie) Bradshaw. After 12 years of marriage Angela is talked into trying sex with a big dicked man. She becomes addicked (pun intended) to it. Terrance catches her in the act. (to really understand read Part I.) The story continues. Terrance watched Angie as she walked to the bathroom. Go...

My Previously Simple Life

by zrob on Sep 16, 2017
Interracial Love

ONE I never saw it coming. I had been married for over 17 years and had never seriously considered cheating on my wife. Sure, I had a couple of heavy flirtations here and there, but nothing even remotely physical had ever occurred. I still found my wife Angie attractive, and our sex life was great; at least twice a week, and she was always willing to expand...

Shortening His Sentence Ch. 02

by SugarandSalt on Sep 11, 2017
Transsexuals & Crossdressers

I knew when writing the first chapter that I'd get around to writing a follow-up chapter. This one definitely requires another installment sometime as well. I mentioned at the start of the last chapter that there wouldn't be tons of sex from the get-go, the same can't be said for this chapter. ;) * Foster's tongue lapped at Miss Julia's cock head. It'd bee...

Three in Bed

by normadel on Sep 16, 2017
Group Sex

From my journal - Ray was out of town. I was horny, so I rented a shemale movie from our favorite adult video shop. When I got home I stripped and laid out my toys and lube for easy access and put in the tape. As I watched shemales having sex, I wondered why some could get hard and why some remained limp. Anyhow, I soon was wet and ready to play. I began on...

Transwood High Pt. 04

by BoobVillian on Sep 12, 2017
Transsexuals & Crossdressers

Christmas is Cumming... Authors note: All the characters in this series are over 18, this is the fourth part of the serious so be nice :-) Sorry for keeping you horny for so long, hopefully this satisfies. The story focuses on our main heroine, and some new/ old faces appear. Enjoy and leave comments! ******************************* 10/12/2016... 'Open u...

Little Liz's Big Suprise

by danny222 on Aug 8, 2020
Fetish

Liz woke up this morning feeling a little horny, which wasn't normal, but this was even different from the rare occasions that she actually did feel horny. It was a little stronger, but with Liz having a medical condition that continued her puberty she was getting used to unfamiliar feelings, so she wasn't too alarmed, just curious. Puberty as it turns out t...

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Spicy Story

by TexanBelgianCutie on Jul 17, 2019
Transsexual

Family Kyle had wildly mixed feelings when he saw his mom walking towards him. He kept his feelings to himself however and forced a big smile to welcome her back from the SpringWood Adult Mental Hospice. He had not seen her since he was child, yet he was glad to see she looked healthy and happy. “Hey Sara”, he grimaced, “How are you? Sara had spent the last...

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Adrius' Noble Adventure Ch. 02

by ScumDumpster69 on Jul 6, 2020
NonHuman

Author's note: This chapter contains horse cock, breastfeeding and cum all the way through. (Make sure you know what that means before reading. Reader discretion is advised!) ***** To the far west of the continent of Korilia, the minotaurs ruled. From the taigas in the north to the equatorial grasslands, these huge, bovine beasts wandered the earth, rarely...

The Surprise Ch. 4

by brgs on Aug 18, 2017
First Time

Turning on the hot water in the tub to soak my knee, I settled into the steaming sauna I had created in my shower stall. Closing the sliding glass doors, I basked in the heat of the water. Pouring a few drops of jasmine scented bubble bath, I turned on the jets to the whirlpool mat. Soon bubbles were all around me and I slipped a little deeper into the wate...