Shemale Surprise Stories

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My Stepmother's Surprise

by sissybr on Sep 12, 2017
Transsexuals & Crossdressers

This is my first story, so I would appreciate some tips and comments. Please enjoy ^^ * My name is Robert, I'm 18, skinny and not too tall. I've never had much luck with girls, in fact I never dated one and I used to spent my days playing games on my computer and watching porn. Shemale porn. Dominant shemales fucking men. I wish i could be one of those men...

A Dream Come True Ch. 01

by severomi on Sep 18, 2017
Transsexuals & Crossdressers

This is a two part story. Part I is reality and true while part II is my Dom's dream. PART I - The truth I'm an American abroad, been in Europe most of my life, now 58 years old and have been married twice with little success. I decided to change what I'm looking for, after having reflected on my previous relationships, where I had also two TG/TS relatio...

Finding My Shemale Goddess Ch. 01

by TheGuyInBlack on Sep 11, 2017
Transsexuals & Crossdressers

Hi, and thanks for reading my first ever submission on this site. I want this to be a multi-part series, so if you have any suggestions I'll be happy to read them. Also, I'd be grateful for any constructive criticism you may have. Thanks again for reading and enjoy! -TheGuyInBlack ********** My hand was trembling as I knocked on her door, I've never been...

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...

Shemale Surprise

by silkstockingslover on Oct 21, 2019
Transgender & Crossdressers

SUMMARY: A married man is seduced and taken by a friend of his wife's. EDITING THANKS: Thanks to Robert, goamz86 and MAB7991. NOTE: This story is dedicated to Robert who requested the fantasy...sorry but the story ended up a lot longer than originally planned. ***** "You can stay with Robert if you wish," Mary said on the phone. I looked up from my lapt...

SheMale Sirens

by WhiskeyIsGood on Sep 25, 2017
Transsexuals & Crossdressers

Of the many mythological creatures invented in the mind of man over time. Some are believable, while others are known to be simple stories created to scare people with weak constitutions or to frighten children at bedtime. Werewolves, vampires, demons... all such creatures are what I am referring to. But the one myth that I had never heard of as a child was...

Amy Finally Lives Out Her Fantasies Ch. 02

by LuvAGoodPegging on Sep 11, 2017
Transsexuals & Crossdressers

(Author's Note: This is a continuation of "Amy Finally Lives Out Her Fantasies -- Shy Amy uses her strapon on Kyle". Thanx to all who provided such great feedback. Hope you like part two. Warning: this story contains male/female strapon sex, cum eating, and as the category suggests, shemale sex. If those aren't your things, you won't enjoy this story. Love t...

Amanda and Me Ch. 03

by Tallnhard1 on Sep 11, 2017
Transsexuals & Crossdressers

The sudden ringing of my alarm clock woke me up at 6:30AM sharp. Rolling over I turned it off and then rubbed at my eyes as I began to wake up. Slowly the events of the night before came back to me and I smiled as I thought about Amanda and how wonderful another night with her was. We had great conversations and another round of mind-blowing sex and I wonder...

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...

Male or Shemale, Still a Slut

by yeaimbored on Sep 11, 2017
Transsexuals & Crossdressers

So this is a 2 part story. Part 2 is strictly shemale and takes place a few years after Part 1. Part 1 is how Brandon became Brenda, although without the "I took bath and did my nails and shaved" stuff because that's not my thing. It's more tranny sex than anything, so if you're only looking for full on shemale skip to Part 2, they're pretty much standalone...