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Transgender Sex Stories – Real Encounters & Passionate Experiences

Welcome to DoubleList’s collection for trans sex stories, where our users share their real, salacious experiences. Your secret encounters are always safe with us because your identity will be 100% anonymous. So, come on in and add your steamy trans erotic stories; we can’t wait to hear them.

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Category: TS / CD

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Unexpected Meeting in a Gas Station Bathroom
Sissy style part 5 As the guy pulls out of my butt in the gas station bathroom. Lots of cum streaks down my leg. I am exhausted. 5 men shooting cum into my anal vault. Enough to be a private sperm

Posted by a TS / CD

By roger5438

A Life-Changing First Encounter in a Hotel
I thought I would share the story of my first time with a man. It changed my life forever. I'm 40 now. My first experience was 10 years ago. I had started watching a lot of TS porn, dressing up

Posted by a TS / CD

By recentlysingleandcurious

A Surprising Connection at the Lounge
Sissy style part 2. He was limp inside of my ass He got up dressed up and left. The meet and greet was only up to having anal sex. Daddies would leave. CD’s could stay and meet more guys. If

Posted by a TS / CD

By roger5438

Unexpected Encounter at the Gas Station
I am a sissy submissive passable crossdresser who loves men. Everything about men: their bodies, the way they smell, and of course, their cock and cum. I have given up my body to a lot of men over

Posted by a TS / CD

By Deleted User

An Unexpected Meeting in a Hotel Lobby
I responded to an ad from a daddy who was in town looking for a passable crossdresser for a night of sexual fun. We exchanged a few body pics, daddy liked what he saw,, I liked what daddy had to

Posted by a TS / CD

By Deleted User

Rediscovering Myself After a Life Change
I am a passable crossdresser. I have been crossdressing for the last 10 years thanks to my now ex wife. When we was married she was my cuckoldress. She would invite men back to our place to fuck her.

Posted by a TS / CD

By Deleted User

Flirty Encounter at the Doctor's Office
I had to take hubs to the doctor the other day for a checkup. There was a very handsome daddy sitting in the waiting room. I couldn't help but look his way. He was in his early 60s, salt n

Posted by a TS / CD

By Deleted User

A Memorable Hotel Visit with Daddy
I have several daddys that I love and enjoy servicing. Most live out of state, and visit me whenever they are in town. I am a submissive bottom crossdresser who lives to sexually satisfy top daddys.

Posted by a TS / CD

By Deleted User

An Evening of Fun at a House Party
Hubs and I were invited to a house party a few weeks ago by a male couple I play with on occasions. T is top, mid 50s, nice daddy bod, nice size cock. R is verse, in his early 60s, smaller cock,

Posted by a TS / CD

By Deleted User

A Weekend Adventure at the Casino
I am a long time crossdresser. I been bi for almost 20 years. I love sucking a hard cock and have it cum in my mouth or in my ass. I have been seeing a guy for over a year once a week or more. I

Posted by a TS / CD

By OlderMaleguy

An Unexpected Encounter on Delivery Day
Herman and Nomar series My parents ordered me a new mattress for my bedroom. My parents wanted it delivered when I was home by myself. I was thinking if it would be possible to seduce the delivery

Posted by a TS / CD

By roger5438

A Playful Encounter on Delivery Day
Herman and Nomar series My parents ordered me a new mattress for my bedroom. My parents wanted it delivered when I was home by myself. I was thinking if it would be possible to seduce the delivery

Posted by a TS / CD

By roger5438

A Special 4th of July Reunion
So I get a call from one of my Daddys who lives out of state a few weeks ago. Daddy informed me that he will be in town over the 4th of July weekend, and he had a lil favor he needed from his fav

Posted by a TS / CD

By Deleted User

Unexpected Encounter During a Taxi Ride
Sissy boy Herman and Nomar series: Well I was feeling giddy. My Herman called said he wanted to fuck me. I told him I would need to take a taxi. My car was in the shop. Taxi driver arrives. I get in

Posted by a TS / CD

By roger5438

A Surprising Reunion During a Hospital Visit
I found out that a daddy I used to date several times a week is in the hospital not doing well. He has some form of cancer. He is allowed 1 visitor per day, so he called me up and asked if I would

Posted by a TS / CD

By Deleted User

Unexpected Encounters with the Lawn Crew
I have been sucking and fucking the young stud that cuts our lawn for the past 2.5 months. I suck his beautiful cock while he is supposed to be cutting our lawn. I make my hubs cut the grass while I

Posted by a TS / CD

By Deleted User

An Unexpected Night at the Party
Hubs and I were invited to a party last week. There were 11 daddys and 2 other sissy gurls that were invited. We got to the party about 7-ish. We walked in, and cocks were swinging everywhere. White

Posted by a TS / CD

By Deleted User

A Surprising Meeting in a Public Bathroom
Sissy boy with Herman and Nomar Well I did not here from my boys. So I decided to put another ad on craigslist. Cd looking to service your needs i weird places. I just wanted to see if any guy would

Posted by a TS / CD

By roger5438

A Unique Encounter Between Generations
The ad said: grandpa looking for passable smooth young crossdresser. Me being a passable crossdresser who loves older men, replied to the ad. We exchanged pics, likes/dislikes, and I was on my merry

Posted by a TS / CD

By Deleted User

An Unexpected Visit During Afternoon Fun
I get a text from a daddy last week. His wifey is gone for a few days and he needs me to stop by for a few hours of fun. I show up at his house about 1pm. I am dressed in his fave outfit: short

Posted by a TS / CD

By Deleted User

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Page 1 of 50 · Showing 1–10 of 500 authors

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