Shemale On Guy Stories

357,756 results
Orientation
Length
Source
Infinite Scroll

Mistress' Shemale Cock Gift

by MasterHornedGod on Jul 4, 2018
Transsexuals & Crossdressers

Mistress strides into the playroom in her usual seductive way, her curvy hips swinging side to side, very large full breasts jiggling ever so slightly even though squeezed together to form a captivating cleavage by her black latex skin-tight leotard. A see-through chartreuse skirt accentuates her luscious hip curves, revealing the french-cut leotard plunging...

The Sex Star Ch. 08

by pinata on Sep 12, 2017
Sci-Fi & Fantasy

When Kayla woke up, it wasn't in the department store fitting room she had fallen asleep in. She was in a white room filled with bright flourescent light, almost like a hospital or something. She tried to get up, and realized she had been immobilized... leather restraints bound her wrists and ankles, and another, larger strap encircled her torso just beneat...

Adventures of Shemale Sandra Ch. 01

by Elyquent on Sep 14, 2017
Transsexuals & Crossdressers

His name was Phillip. Or at least it had been. Honestly, he wasn't sure who he was; all he knew was that what he had done two years ago was what he thought was right. This was the lifestyle he wanted. It should be said that Phillip has always had strong female influences throughout his life. He and his three sisters were raised in a single parent home by th...

All the Way

by NearMiss on Sep 18, 2017
Transsexuals & Crossdressers

A different spin on the typical 'I got caught dressing up' story. I've always been fond of large women, not obese necessarily but you know, big. Like Amazonian big. Tall, big curvy hips and a chest to match with broad shoulders, but not in a masculine way mind you, but kind of proportionate for a girl. Let me tell you they aren't really that easy to come...

Attack of the Chakra Witches Ch. 02

by Nocturnal_Ferret on Sep 16, 2017
Transsexuals & Crossdressers

########## Chapter Two I witness others broken to the chakra ########## I awoke not to the sound of fighting, but fucking. And not the high-pitched squeals and cries of women, but the throatier entreaties of men who were either pleading and begging or moaning out their pleasures nearby. And around me there appeared to be several Altan men, some still...

Jenna & Stephen Ch. 01

by Naf_Noparts on Sep 12, 2017
Fetish

(Author's Note: This is a true story, one that tells of my hot experience with a friend who fucked me with a strapon. If you are bothered by the idea of women ass-fucking men with toys, then this story will not be to your liking. Thanks in advance for all constructive feedback!) * Jenna and I have been friends for nearly 15 years. We dated ever so briefly...

Somewhere else.

by latexdoll on May 23, 2010
Fantasy

Waking up this morning I bet you didn’t know it would be the last day you spent here on earth. Climbing out of bed you hit the alarm clock for the third time, you can’t quite place what is wrong, you just can’t seem to get out of bed. Getting ready for work is more of a chore than usual. For whatever reason nothing seems to want to cooperate. Your shower hea...

Open in Reader

Swallowing My First Shemale

by Nitromethane on Oct 14, 2017
Transsexuals & Crossdressers

It's been a couple of years now that I've been intrigued by shemales, and though I've met up with a few I've met online, I've still not gone any further than some stroking or letting them blow me. I'm not sure what my hangup is, since I can't seem to stop watching these gorgeous girls on all the websites, but I'm still so nervous about taking that big first...

Just Another Story

by neoview on Oct 15, 2017
Transsexuals & Crossdressers

Once upon a time... "Wait, wait, wait! We're not actually starting the story like this, are we?" Said the short fat kid in his mid-twenties. "I'm neither short nor fat." He said while swallowing his stomach and lifting himself on his toes. "I'm not doing any of that. STOP GIVING THE READERS FALSE INFORMATION!!" The angry non-short, non-fat kid yelled. "H...

Pam's Shemale Experience Ch. 07

by majicman21 on Aug 20, 2018
Transsexuals & Crossdressers

Author's Note: While this is quite obviously a continuation of Pam's Shemale Experience, it also follows 'Pam's Gangbang Experience' from the Group Sex category, 'Pam's Lesbian Experience' from the Lesbian Sex category, and 'Pam's Threesome Experience' from the Loving Wives category. Reading those three stories might not be necessary to enjoy this one, but i...