Male On Shemale Stories

358,017 results
Orientation
Length
Source
Infinite Scroll

Neighborhood Good Boy

by Kami107 on Feb 13, 2020
Transsexual

Brian had recently turned eighteen, he was finally a man. Although he didn't quite feel it. He was much smaller than the other boys around his age being only 5'4" and weighing in at a measly 120 lbs. With black hair, pale smooth complexion, skinny but proportionate limbs and wide hips that contoured his firm bubbly butt, his effeminate features didn't q...

Open in Reader

Sexy Black Boots

by latexdoll on Apr 8, 2007
Fantasy

While walking through the local mall you suddenly notice one of your fellow coworkers coming toward you and not wanting to deal with this obnoxious jerk you find yourself quickly ducking into the next store you see to get out of sight. With out even paying attention to the store you find yourself walking all the way to the back of the store to get out of sig...

Open in Reader

I was Scott Tenna

by tre34harr on Sep 19, 2017
Transsexuals & Crossdressers

If shemales aren't your thing don't read on; if they are please read enjoy and have your eyes opened. ***** "I hold my hand up and tell you truthfully that I used to be a guy; just like you or like any other guy you know or have met in your life time; into the normal thing a typical uni male student of his age would be; girls, drink, football and cars. H...

One of the Girls

by Erotictales4u on Sep 26, 2017
Transsexuals & Crossdressers

All characters in this story are over 21 years old. This is a fictional fantasy that contains elements of both femdom and the transsexual/cross-dressers niche. This is my first attempt at a story so go easy. ***** I couldn't believe my situation. I had signed up for porn, but I had not signed up for this. I was standing naked in the dressing room and the c...

Garnet: a Story of Submission Ch. 03

by frillypanty on Sep 16, 2017
Transsexuals & Crossdressers

3. A fashion parade and the appointment of a fourth Mistress The image of my three internet mistresses came up true to time, immediately after I'd logged on at 1.15am on the Sunday morning following my second shopping expedition to extend my feminine wardrobe – as directed by them. Like me all three were clad in lace trimmed and panelled underwear – bra',...

HypnoSissy: Educated to be Pegged

by silkstockingslover on Aug 13, 2019
Fetish

Summary: Cock sucker's training is advanced to hypno videos on anal sex. WARNING PLEASE READ: -This is a hypnosis story with potentially influential subliminal messages within it. -The story also contains hypnosis video scenes. -So if you begin behaving differently after reading this story and all your friends start pointing fingers, don't come crying to...

The Swollen Root Boarding House

by generaljiggler on Oct 29, 2015
Fetish

Cody stepped out of the taxi with a smile on his face. He had finally made the big move out of his parents house and was ready to start the next chapter of his life. At eighteen years old it was time to start college. Cody hadn't been particularly keen on the idea of sharing an already cramped room with a total stranger during the first year of his college l...

Open in Reader

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...

Shemale Shopping Spree

by tawnysuede on Sep 19, 2017
Transsexuals & Crossdressers

She-Male Shopping Spree featuring Chelsea and Victoria, two gorgeous chicks with dicks - and an attitude! by Mistress Tawny Suede "Oh god, I feel so incredibly horny!" said Victoria. "Well, sugar, if we hurry back to the apartment, I've got just the cure," said her best friend and roommate, Chelsea. Victoria looked the stunning black girl in the eye a...

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...