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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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A Surprising Reunion at the Party
I posted earlier about being at a party n my stepson fucking me after not seeing him for bout 10 years. Well, him n I have hooked up a few more times since then, n he still has NO idea I am his x

Posted by a TS / CD

By sissyjamie4daddys

A Night of Surprising Connections with Daddies
I moved to another state, n started posting in that local area for any daddy that needed a sissy to use. I got a few responses n chose daddy #1. I stopped at his house bout 11pm. I was dressed in a

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Encounter in a Car
When i turned 18 i used to go walking and id post my location so dudes could find me and watch me or whateve and i had a guy walk up to me put his hand on mt back and lead me to his car. When we got

Posted by a TS / CD

By Deleted User

A Crossdresser's First Encounter at the Motel
I have been a crossdresser ever since I could remember but my first experience with a man came when I was 19. I was looking through personal ads section on Clist for weeks until one ad caught my

Posted by a TS / CD

By jennycd77

A Unique Gathering at the Football Watch Party
I am a very submissive Asian CD and getting gangbanged has been my dream forever so I invited 5 daddy's I've met through the years to a football watch party and have a little fun. I had my

Posted by a TS / CD

By jennycd77

Exploring New Connections and Personal Growth
straight guy all my life, masculine tattoos Harley people . women married years. kids whole box thing. I have had a guy give me bj years ago. . I like pussy. younger . I been single 8 yrs met a

Posted by a TS / CD

By richardintime6969

Exploring New Fantasies: A First Meeting
I am new crossdressing so I hadn’t been able to meet guys and explore my fantasies. Keeping it on the DL big time. Well I had decided one night I was tired of jerking off to porn loving other

Posted by a TS / CD

By deserina123

A Journey of Self-Discovery and Connection
I’ve been crossdressing for as long as I can remember but never really thought about being with a man until a couple of years ago. I went on a few site trying to find a man to dress for but all

Posted by a TS / CD

By Tommy

A Unique Encounter in a Hotel Room
I had always crossdressed but it was always alone at home and I never ventured out but that was about to change. My fantasy was to become a cum-loving slut under the direction of a strict mistress.

Posted by a TS / CD

By Deleted User

A Mysterious Late Night Visit with a New Friend
I didnt want to brag but my BBC Mommy let me see her 2 night in a row. The first night i talked to her it was after midnight when made a date for her to host me. Now im an older average daddy by day

Posted by a TS / CD

By rachelbottomcd

Old Friends Reconnect in a Small Town
old high school friend I live in a small town that would not understand what i do. so for the most part i hide it . with that said i had a old high school friend stop by for a visit. he had just

Posted by a TS / CD

By samantha1965

An Unexpected Revelation at Home Leads to Change
When I was about 40 I met my wife sex was good I went to work one day while she went through my computer she called me at work saying we need to talk I found out you're gay what she was flipping

Posted by a TS / CD

By daviddickson

Unexpected Connection at a Rest Area
I'm a straight acting male in public. I always wear fem clothes under my manly clothes, you know, just in case. So last week I was out of town on business. I stopped at a rest area to tinkle. I

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Night with New Friends
My first threesome: Back during Craigslist days, I had hooked up w/ this 1 guy a year or 2 prior & we had fun, but he vanished off Craigslist (found out he had moved for a little while out of

Posted by a TS / CD

By WalrusHaven8010

A Surprising Encounter in a Sundress
I started putting on my sister and stepmothers cloths and make up when I was a senior in high school. I had long hair and my girlfriend used to comment on how feminine my lips and eyelashes were.

Posted by a TS / CD

By Deleted User

A Beach Town Encounter with a Younger Man
Well, I just have to tell this true story while it is fresh in my mind. I had placed an ad in DL as a very fem submissive sissy slut looking for tops who like long sessions of using my mouth, lips,

Posted by a TS / CD

By sissyphun

Unexpected Connection Between Friends on the Couch
...well as a lay there mouth fucked and pussy fucked I felt I had my fill for the evening. The 2 men left and as they did I noticed another CD on another couch had been watching all of this. I sat

Posted by a TS / CD

By spanishblau

A Winter Encounter at the Adult Arcade
Been CDing on and off for years. There is a great Adult Arcade in CT that I visit when I get the urge. I dress fully. I'm a tall gurl at 6 foot and hwp. The place has GH and also a large

Posted by a TS / CD

By spanishblau

A Nervous First-Time Encounter with a Dominant Date
I love dressing up in woman's clothes and lingerie. It makes me feel so bad! I slowly got into crossdressing over the years and eventually got into dildo play as well. One night I was feeling

Posted by a TS / CD

By dildo_boy93

A Bold Encounter with the Neighbors
I love turning out straight men. I am a bi 24yo white TS slim with perky 20k tits and a 6in shecock sholder mid back leingth hair black with blond highlights. I have a thing for turning out straight

Posted by a TS / CD

By sub79_whtbottom

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
Straight for Gay Couple Straight
I couldnt refuse the temptation. 50.0k 738 4.3k
#2
Tiffanyheels
Straight Couple Trans
Finally had intimacy with ex mother in law 101.0k 1.7k 3.4k
#3
KestrelElbow9092
Straight Gay Straight for Gay
A chance meeting. 36.3k 429 3.2k
#4
kimorafoxxsexycd
Gay Straight Couple
Bf was a sweetheart today 102.2k 1.2k 3.1k
#5
cnysub
Trans Gay Straight
My boyfriend/ Master/partner 61.4k 618 3.0k
#6
sissyjamie4daddys
Trans Couple Straight
I love water 61.1k 470 1.9k
#7
wally4u
Gay Trans Straight for Gay
My Night At The Anvil... Part 1 58.1k 279 1.8k
#8
Steve
Straight for Gay Straight Gay
Gym kiss pt.2 52.0k 631 1.7k
#9
powers8
Straight Straight for Gay Gay
My greatest vacation ever 52.3k 487 1.3k
#10
butchmax
Straight for Gay Couple Straight
My Wife Got Sick 60.1k 472 1.3k
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