Cuckold Shemale Stories

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Jasmine Fucks My Wife

by cuntenslaver on Sep 12, 2017
Transsexuals & Crossdressers

Hello, my name is Tim. I am a 30 year-old married man. I have been married for five years to my wife Danielle. She is an absolute beauty of a woman. I remember when we were married, I felt like I was the luckiest man in the world. Since I am no hunk myself, standing at just five foot six and extremely lanky, I felt like I didn't deserve such a nice, gorgeous...

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...

Shemale Utopia

by Lewd_Ruby on Jun 15, 2016
Transsexual

*De-De-De-De-Deep* *De-De-De-De-Deep* *Click* I gently pressed the large red button atop my alarm clock to stop the annoying racket of those high pitched beeps. Sitting up I began to take a look around at my surroundings, Beige wallpaper spread across the walls, the odd video game poster stuck on lazily with some blu-tack. Letting out a small sigh I swung my...

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The Society

by Barno on Sep 19, 2017
Transsexuals & Crossdressers

I met her during the summer. I was only nineteen and working to save some money for college. I had been raised by my grandparents who had both passed away over the past year. After the burial costs I was far from wealthy. My parents weren't around so I was on my own at a young age. I had moved a couple of towns over from where I had grown up and was living i...

The Gym Ch. 4

by Kip Carson on Sep 14, 2017
Group Sex

John arrived at Kate's house at 6:50 pm. She answered the door in a very tight fitting short dress. "Damn, you look good" John told her. "Sorry I'm so early, but I was so excited about tonight" he added. "That's fine, I'm always ready early" she said. "And you look pretty damn good, too" she added. She eyed him up and down. He was wearing black dockers, a ni...

Dot Makes Tim a Cuckold Ch. 07

by wantwhitewomen on Sep 19, 2017
Loving Wives

Just incase you forgot, this is a story about a black man who is fucking a white woman. It is also a story about the husband who is now a cuckold. The HUSBAND wanted to be a cuckold!! Please understand, it's not against the husband's will, HE WANTS IT!! Enough said, read it if you like this type of story. Don't read it if you don't like this type of story. I...

Por que

by Ssrd33 on Apr 22, 2019
Transsexual

We're all super, for some reason my mouth felt tired and had a taste, my ass hurt, the other night we were having a great time on a record. It's the only thing I remembered from the other night. Suddenly the teacher said that a new student was going to enter. We were excited by a new student, fresh meat. The teacher said that his name was Melany, for some re...

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Pam's Shemale Experience Ch. 09

by majicman21 on Aug 7, 2019
Transgender & Crossdressers

It was Tuesday morning, the second day of the weeklong teacher's conference, and almost the entire room was paying close attention to the speaker, one Martin Greenman, forty-seven-year veteran of the classroom and expert in educational theory. The only one not paying attention was Pam. She was in the front row, doing her best to listen and sit still. Next...

Pam's Shemale Experience Ch. 12

by majicman21 on Oct 12, 2020
Transgender & Crossdressers

Pam and Alex sat together on the bed, the former watching television, the latter on her phone. It was their last night at the hotel. Some of the teachers at the conference had organized a group outing earlier in the night to a nearby restaurant for dinner and drinks, as a farewell of sorts. Pam had gone along, but Tanya had been unable to. "I have a date,...

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...