Shemale Fucks Boy Stories

119,352 results
Orientation
Length
Source
Infinite Scroll

Showing Off For My Wife's Pleasure

by HotJennieh on Sep 19, 2017
Fetish

A first time effort based on real events. * There I was lying on my back, on the floor of a cheap adult bookstore. All I was wearing were 5" heels, black thighhighs, and a nipple chain. In one hand, I was jerking my throbbing shaved shaft while I was using my other hand to fuck my ass with a double headed dong. Cum was glistening on my face and chest and r...

Shemale Seduction - The Surrender

by BigAndy922 on Sep 14, 2017
Transsexuals & Crossdressers

I cannot remember what drove me to it. Cruising bars for sex had become a habit. Success can do that to you, but even steady success make you yearn for something different. I looked at her from across the bar and acknowledged her stare. She definitely looked hot and hungry, with eyes that seemed to size me up as a meal. I was about to approach her, when, sur...

Chemical Flavor

by Miles63 on Sep 13, 2017
Transsexuals & Crossdressers

Introduction: Sorry that it's taken so long to upload a new story. I've been sitting on this one for nearly a year as I loved the beginning but hated the ending. So after a big deletion and a big re-write I now like the ending. I've been just mentally drained for awhile and no story was coming to me, but now finally something to upload. Any errors please be...

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...

Open in Reader

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...

T-Girl Van Sex

by available269 on Sep 12, 2017
Transsexuals & Crossdressers

Pulling up to the curb near the bookstore one recent night, I happened to notice a nice looking custom van drive by very slowly. Looking intently at the driver as it passed by, I noticed that the driver was a very sexy looking woman, and she gazed at me intently as she passed by. The van pulled up to the curb in front of my car and parked. Shortly afterwar...

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...

Agent Mari

by Ssrd33 on May 28, 2019
Transsexual

Ignacio was a very lonely man he just liked to share with his friends. On one occasion, after so much insistence his friends managed to get him out of the house. On that occasion they went to the outside of the city. In the middle of nowhere is the motel where they stayed. Agent Mari was in that place for her clumsiness but great determination and willingnes...

Open in Reader

Sister's Shemale Friend

by silkstockingslover on Sep 12, 2018
Illustrated

Sister's Shemale Friend Summary: Family seduced and dominated by an irresistible shemale. Note 1: This is a Summer 2018 Contest Story so please vote. Note 2: Thanks to DarkBreezly for creating the pictures in this story. Note 3: Thanks to Tex Beethoven, Robert and Wayne for editing this story. I came home from work a couple hours early, as our manager...

The Neighbour Who Had It All

by TheTitLover on Sep 25, 2017
Transsexuals & Crossdressers

Not my usual fare, if I have enough stories to be considered usual. Shemale, transsexual, chick with a dick, whatever you want to call it, it's here, so fair warning. I'd also consider it a bit of a romance story, though not a straightforward one. There's also some master/slave, not very much, it's more a hint of where their relationship will probably go i...