Sucking My First Shemale Cock Reddit Stories

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My Teacher is Blackmailing Me

by Yelawolf on Apr 29, 2025

(Everyone is 18 year old or older) I stare at myself, my body mask in a sexy schoolgirl skirt. The plaid coloring is the typical kind, a regular red and black. The white blouse matches exceptionally well. I fasten the cute small black tie around my neck. I'm John, kicking off my senior year of high school. I recently turned eighteen years old as fall began t...

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A New York Tale Pt. 05

by neuromancerzero on Aug 26, 2019
Fetish

I woke up early the next day, despite us staying up late. The warmth of all five of us on a queen bed was too much for me. I was thoroughly entangled by limbs and I had to carefully extricate myself as so note to wake them. After five minutes of untangling notes, I was able to discretely slide into the shower and rinse myself off of the potpourri of bodily f...

Pam's Shemale Experience Ch. 11

by majicman21 on Jun 1, 2020
Transgender & Crossdressers

Content warning: one scene with a golden shower. "Ah, what a way to start the day," Tanya sighed, letting her cock slip from Alex's pussy. The shemale had just filled it with a load of cum, dribbles of that gift already leaking out. Pam smiled from next to them, at the possessive yet affectionate way Tanya slapped her cock onto one of Alex's thighs and...

The Sexiest Shemales Ch. 03

by cleanly_shaven on Sep 13, 2017
Transsexuals & Crossdressers

I woke up laying on Daisy's inner thigh. Her cock was lying right in front of my face. It smelled so good. It smelled like sweet perfume and cum from our previous romp. I smelled it and began rubbing the tip of my nose on it and then slowly I began kissing it. Daisy began to slowly wake up and did her cock. It grew more and more as I continued to kiss it and...

Peace In Our Time

by ladyapollo3583 on Jan 22, 2020
Text With Audio

There are many in my court who are calling for your execution as a show of force against those who would do us harm, while others feel that such violence would only result in retaliation from your people. They would simply have you ransomed off back to your people as a show of good faith, as well as our own superiority. The script is by u/rottenpines from...

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...

City Getaway

by muaddib75 on Nov 21, 2019
Erotic Couplings

Meet the characters: * Jake - 185 cm tall, lean build, reasonably fit, short dark hair and green eyes, trimmed beard. * Michelle - 170 cm tall, reasonably fit, shoulder-length brown hair, hazel eyes, average sized breasts and round ass. Michelle opened the door using her key card and turned on the lights. She quickly inspected the hotel room with a few glan...

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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...

Jabba's Shemale Slave Pt. 02

by mkh78 on Oct 8, 2019
Celebrities & Fan Fiction

This story is from the imagination of the writer and inspired by Return of the Jedi. I have used Huttese words in some parts. These are not of my own. *** 1:30 am. Tarno and the Twi'lek shemale prostitute he found and subsequently bought from the brothel's owner, were now quickly speeding across the Tatooine desert. He considered spending the night at a...

Pam's Shemale Experience Ch. 10

by majicman21 on Dec 2, 2019
Transgender & Crossdressers

Pam woke up, and as she remembered what day it was, a smile crept across her lips. Earlier in the week, her owner had decreed that she would not fuck Pam until Wednesday. That had been Sunday night, and now, with Monday and Tuesday past, today would be the first time in a long time she would feel that magnificent cock opening her up. It's been too long.....