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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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An Intense Night with Daddy Mans
"Come on daddy mans, pound my sissy cunt. Yeah that's it, long stroke my ass" I told daddy mans over n over again. "That's it fuck me. Pump my faggot ass n dump that creamy

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Encounter with the Repairman
Last week I was having an issue with my washing machine. I had to call a service guy to come out n take a look at it. He got to my house bout 930 last Wednesday. Fine looking, beefy stud bout my age

Posted by a TS / CD

By sissyjamie4daddys

A Bi Guy's Journey with a Dominant Couple
I was a bi guy but met this Dominate couple at a BD/SM party and got to play with them, tied up, spanked, flogged nipple clamps and more. I'm a smaller guy not hairy, no beard, the male Dom

Posted by a TS / CD

By Deleted User

Unexpected Holiday Weekend Roommate Encounter
hope everyone is having an amazing holiday weekend i been of my boyfriends house all weekend and having a blast i feel like i should be pregnant on how many times he has filled me up and his roommate

Posted by a TS / CD

By ababycd

An Unexpected Encounter at a Hotel in East Bay
I was cruising home from work in the East Bay when I saw this beautiful woman I could kind of tell she might be a tranny that even turned me on more so I stopped listening to music in my car smoking

Posted by a TS / CD

By ejstorm6981

A Journey of Love and Training
My very first daddy trained me properly on how to properly greet other daddys. On my knees, mouth open to show respect to the alpha man. Daddy also trained my sissy cunt. Daddy bought me a vibrating

Posted by a TS / CD

By sissyjamie4daddys

A Surprising Meeting in the Garage
I replied to an ad posted by a top daddy who was looking for a bottom sissy. Hey, here I am! We exchanged a few pics, he gave me his address, and I was on my merry way. Daddy told me to pull into his

Posted by a TS / CD

By sissyjamie4daddys

A New Beginning: Finding Connection After Divorce
I love men. I love their bods, the way they smell, the way they kiss, and of course, their tasty, yummy cock and balls. And I most def love that creamy goodness, that yummy treat, their cum. OMG, I

Posted by a TS / CD

By sissyjamie4daddys

Unexpected Encounter at the Baseball Game
One of my older daddy mens texted me n invited me to watch his grandson play baseball. Daddy mans told me he wanted to fuck me while at the game. Now I love PDA, n fucking in public. It's such

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Office Encounter
Continued part 2 My sugar daddy mans told me he was looking to fill a few positions for his bizness. Then he told me that this would be a oral interview. He made sure his assistant heard that. I

Posted by a TS / CD

By sissyjamie4daddys

A Weekend Adventure at the Cabin with Friends
I call him Daddy but he is younger than me and I enjoy the way he dominates me. Daddy called and said we are going to the cabin this weekend. I will pick you up after work on Thursday. I get all

Posted by a TS / CD

By bjsnakes

A Surprising Business Meeting with a Twist
I'm not much of a role playing kinda gurl. I don't dress conservatively, sure as hell don't act conservatively. I dress slutty. Low cut blouses, tops, shirts, always showing off

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Chocolate Craving Visit
I get a craving for chocolate every few weeks. I love me some BBBCs! Today I had such a craving, n hooked up with a younger stud who had that swinging meat tween his legs. He came over to my house n

Posted by a TS / CD

By sissyjamie4daddys

A Late Night Encounter in Hong Kong
Hong Kong part 2 I was kneeling on the bed and he was driving his hot cock deep inside me. I knew he would have to cum soon and I felt his hand reaching around and fondling my cock and balls

Posted by a TS / CD

By foxy157

A Business Trip Leads to Unexpected Connection
Hong Kong part 1 I was in Hong Kong on business and was looking through the local ads and saw one looking for a caucasian who was uncut. That was me so I answered the ad and after several email

Posted by a TS / CD

By foxy157

Unexpected Encounters at the Adult Theater
Continuing with my visit to the adult video theater. It was only 11:00. I had already been face fucked by the two store clerks and a beautiful large your stud The day looked like it could be a very

Posted by a TS / CD

By mcg00011

A Unique Encounter at the Park and Beyond
This happened the day. I was going to meet up with this guy . I'm a male cross dresser that loves wearing sexy women's clothing, lingerie, costumes and high heels. We were going to meet up

Posted by a TS / CD

By Miniho

A Surprising Meeting at the Local Theater
To follow up on my previous post I had just been face fucked by the two clerks working the counter at the local adult video theater. I had only been at the theater less than 20 mins and already I had

Posted by a TS / CD

By mcg00011

An Unexpected Coffee Meeting at His Dream House
When I was younger I was homophobic. I didn't like gay men. I had no gay friends. To me, bring gay was a sickness. I got married at 20, divorced at 30. I dated a few women but nothing serious.

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Connection at the Gay Bathhouse
I'm not crossdresser but a guy who loves them. I consider myself gay but not attracted to guys just crossdressers and transsexuals only if they still have a penis, I'm wierd I guess. It

Posted by a TS / CD

By Deleted User

Top Authors

Discover the most engaging creators on Doublelist — ranked by views, listens, and upvotes, with fresh voices breaking in every week.

Rank Author · Category Latest Story Views Listens Upvotes Trend
#1
derake14
Couple Gay Straight for Gay
Letting her desires take over 81.7k 1.0k 4.7k
#2
Tiffanyheels
Couple Straight Trans
Excited wife self-pleasure 181.9k 2.5k 4.5k
#3
kimorafoxxsexycd
Trans Gay Couple
Fun at the store and with ex friends baby daddy 165.3k 1.7k 4.0k
#4
KestrelElbow9092
Gay Straight Couple
Need to be feminine. 84.0k 722 3.6k
#5
butchmax
Gay Straight Straight for Gay
I guess I am what I am 128.1k 850 2.2k
#6
Dedavis
Straight for Gay Straight
Hot tub connection, part two 108.5k 735 2.0k
#7
wally4u
Gay Couple Trans
Drunk Abs Experience I'll Never 4Get! 74.9k 331 2.0k
#8
sissyjamie4daddys
Trans Couple Straight
I love water 87.2k 498 2.0k
#9
Steve
Straight Straight for Gay Gay
Vacation with my Aunt part 1 59.6k 689 1.8k
#10
powers8
Gay Straight Straight for Gay
A fantasy come true 88.4k 678 1.7k
Page 1 of 50 · Showing 1–10 of 500 authors

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