Trans Cuckold Stories

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Orientation
Length
Source
Infinite Scroll

Lost Empire Ch. 06

by Pars001 on Sep 13, 2017
Non-Erotic

Derrick looked at the readings, pausing only a second, he pressed the start button, at first it wasn't too bad. Suddenly it was like the full opening of a huge set of flood gates. Derrick opened his mouth to scream but nothing came out, reaching up he tried to pull the head set off, no dice it only increased the feeling that his head was going to split open....

You Too?!

by dreadknots on Oct 12, 2020
Transgender & Crossdressers

Janice didn't know WHY her roommate had to work out every day, but it aggravated her to no end. The pandemic had shut down all the gyms, meaning the 6'2 goliath had to use their shared living room as a personal workout space. He was usually thoughtful enough to clean up afterward. Usually. But the scent of sweat lingered in the air for hours afterward. "48....

Transvixen Tranny Rock Band Ch. 07

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Seven: Panti Love - Michelle Lust 'So how did Panti and Phil Benson get together?' Michele pondered as she sat in the back of the limo being driven to the Bocca di Lupo restaurant for her date with Tony Carlotta. Well it came about as follows... After the second concert Panti lay on the park bench gratified and sated having had sex with two strang...

The Choice

by MaxwellSpanx on Sep 13, 2017
Loving Wives

Author's note. This is a redraft of an earlier story - Paying her Way. It's largely the same but with some plot modifications. Hope you enjoy. Feel free to comment. * Deena's Story Before I was an escort, I never had anal. Now it's my bread winner. I never had a potty mouth either. I used to be a classy girl from a conservative British Asian family. Th...

Car Talk

by BOSTONFICTIONWRITER on Sep 17, 2017
Non-Erotic

I got married shortly after I bought my New Yorker. I kept it for 7 years before selling it to my brother, who kept it for another 5 years. I bought a brand new '79 Pontiac Grand Am, 4 door sedan. We were talking about kids and even thought I wanted something more befitting my male testosterone, like a Mustang or a Camaro, I settled for the Grand Am. Now,...

First Time Fucking A Trans Man

by silver_midi on Sep 19, 2017
Transsexuals & Crossdressers

I wanted to satiate my curiosity. I am a gay man who has always been with men, but one day I stumbled upon some porn with gay trans men being fucked by gay men (I guess they are called cis guys) and I was surprised to find myself incredibly hard and turned on by this. After an evening foray into this genre I was very interested in meeting such a man. After l...

Lets Say - An Orgy.....

by sexual_indian on Sep 13, 2017
Group Sex

Another of my narrations, you might notice most of my stories are incest, but this one is a little different. I am 28 year old, regular guy. The encounter i want to talk to you about now happened when i was just 18 years old and just joined college to do my degree first year. I was not a virgin by then. But this is much different and unique in my life as I...

Condominium Ch. 11

by SteveWallace on Sep 18, 2017
Group Sex

Chapter 11 Diane came to our apartment at lunch a few days after a party. Penny was in school, and Amber was off working with a client. I escorted her in. She looked succulent, and I wondered if she had a sexual agenda or why she was there. "Jon, I'm here for two things. First, I met a nice man who I think would like our party group. He lives in 1402 - rig...

The Survey

by sraynes on Sep 16, 2017
Transsexuals & Crossdressers

I glared at the green sticky note placed on my dashboard, trying to memorize the new survey pitch. The company changed that damn script five times since I started work last year. I always hated going door to door, asking people about the air quality in their homes, only to do sales pitches after they completed their surveys. But, it paid $17 an hour, plus a...

Palace: The Dark Room

by acmsrk on Sep 17, 2017
BDSM

Thank You for Volunteer editor Ortay Ortay. ***** Riya was a twenty-five year old divorced woman who had adopted one of my younger cousins. She is an Anglo-Indian and after her divorce, she chose to settle in India. As I was very affectionate towards my cousin, I frequently visited her Palace. In one word, Riya was perfect. She was smart, kind and sexy. W...