Shemale Fuck Male Stories

256,422 results
Orientation
Length
Source
Infinite Scroll

Somali Femdom: New Convert

by Samuelx on Sep 14, 2017
Transsexuals & Crossdressers

Mistress Fatuma Suleiman, Supreme Matriarch of the world-fastest growing religion, the Fatumanism Faith, looked down at her latest supplicant, Ahmed Dawit. The six-foot-tall, burly and broad-shouldered, bronze-skinned and brown-eyed, hairy Egyptian male grimaced as Fatuma's cohort, Lady Karma, thrust her cock into his asshole. Mistress Fatuma Suleiman smiled...

Shemale Devil in Disguise Pt. 01

by Chomedey on Jan 20, 2020
Transgender & Crossdressers

This story talks about how a charming shemale I thought was completely harmless practically stole the love of my life and my honor. It's May 2018. I just finished my third year of University. One more year of school and I graduate with a degree allowing me to enter the job market. This summer after passing my exams, I was planning on staying at my parents...

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...

Father-In-Law Shemale Adventure

by greyhound_guy30 on Sep 16, 2017
Transsexuals & Crossdressers

My wife's parents were visiting LA from back east. We live in a small one-bedroom apartment in the valley. She wanted them to stay with us but we didn't have room. They got a room in West Hollywood. My wife and her mom had gone shopping for the day. I was supposed to be at work but at the last moment I decided to take the day off. Since the girls were out, I...

The Making of a TLB Pt. 03

by TheMarlboroMan on Sep 23, 2019
Transgender & Crossdressers

I suggest you read parts one and two to pick up a man's journey to womanhood caused by the woman he loves, his wife. Some of the items used may not be available in the market today. Rest assured they will be. The key to any conversion is the manipulation of one's mind. What the wife fails to remember is that each one of us has freedom of thought. I got up e...

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',...

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

Shemale Shock Continues

by standingstones on Sep 12, 2017
Transsexuals & Crossdressers

I met Cheryl at a party thrown by my sister. I asked Cheryl to come to my place afterwards and she agreed. That was where I discovered Cheryl was a shemale. I did something I had never done before. I sucked on Cheryl's cock and I took her load down my throat. After that I ended up fucking Cheryl's tight ass and giving her my own load of cum. We had now been...

Romina Ch. 01

by Lubba on Sep 13, 2017
Transsexuals & Crossdressers

I was round at some male friends flat having a few beers after a night out. When none of us got lucky on a night out it became the norm for us to watch one of the many porn videos they had collected over the years. One of the guys had returned recently from Amsterdam and bought a few budget films which had trailers at the beginning of some fetish films. We...