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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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A Journey of Self-Discovery and New Encounters
Once upon a time I went to that community store and bought $200 worth of female clothing. And then went home and shaved my body and transitioned into a sissy bimbo cocksucking slut. I posted an ad

Posted by a TS / CD

By Deleted User

A Mysterious Encounter in a Hotel Room
Hotel Slut Part 2 How did my brothers friend know it was me. The only person I told what I was doing was my best friend whom I had never done anything with. I decided to message him. He responded

Posted by a TS / CD

By Deleted User

A Curious Encounter Through the Window
I always loved dressing up alone. Never showed or told anyone about my hobby.lol In my early 30s, I lived in an apartment complex and my bedroom window faced the adjacent apartment building. I

Posted by a TS / CD

By Anonymous

A Night of Unexpected Encounters in a Hotel
Hotel Slut Part 1 I was so horny but living in small town there wasn’t much chance for cock as all the guys I knew were straight or so I thought. I secretly loved cross dressing and being

Posted by a gay man

By Deleted User

A Mysterious Encounter in the Dark Room
I have been secretly dressing alone for a long while and j/o while wearing a dress, panties, sexy thigh high hose and a bra, fantasizing I’m a woman. I have for a long time been extremely

Posted by a straight man

By emod1

An Unexpected Connection at the Motel
I made a connection here to meet at a motel and we’ll have a lot of fun❣️ I was excited as this man shared his cock pic and I was so ready to be his slut. I arrived dressed a tad slutty

Posted by a TS / CD

By Deleted User

An Unexpected Dinner Party Experience
I met a couple of cross dressers on double list and decided I would meet them. I decided to offer my service to cook for them and serve them drinks. After dinner was over I was cleaning up and

Posted by a straight man

By deinbismark

A Night of Transformation and Connection
So many times I went to a motel room and change in to a sexy travesti sexy all shave nylon stocking garter belt hi heels short dress makeup and invited top Male to come and fuck me like a woman

Posted by a TS / CD

By carolyne

A Night Out at the Drag Show
A Night At A Drag Show So one night I went to a local gay friendly bar in my city. It was a night that they had a drag show, but I might add I didn't know about it as it was a random night out

Posted by a TS / CD

By Theresa

An Unexpected Connection at the Clinic
Hook Up In A Clinic. So a few years back I was out of town. I figured I would go to a local clinic to get tested as I do quite often. I made an appointment and went the next day. They usually run

Posted by a TS / CD

By Theresa

Exploring New Relationship Dynamics Together
Hello well I thought I would share my story. I have always found the naughtier stuff of sex to be very arousing but this story is starts later in life when I was in my early 30s and dating a girl

Posted by a TS / CD

By Deleted User

A Surprising Meeting on a Late Night Drive
It's been awhile since I wore crossdressing clothes. But one late night I drove around some back rds here at home I came up to this car that was in a ditch. I pulled up didn't want him or

Posted by a TS / CD

By Deleted User

A Surprising New Year's Encounter in a Public Toilet
It was New Years 2023 it was getting closer to 12pm I was getting so horny so I left the bar I was at and found a public toilet quiet hidden away in circular quay no one around well that’s what

Posted by a TS / CD

By laymedaddy

Exploring the Unique Bond Between Best Friends
Oh my bbc is the best…. Gawd!!

Posted by a TS / CD

By tscassy

A Secret Encounter Next Door
My name is Steve and I’ve been cross dressing and servicing guys since I was 12 years old. I married a beautiful woman named Julie about a year ago and thought I was over it but those old

Posted by a TS / CD

By OspreyGrove7318

A Night of Secrets and Surprises Over Whiskey
Instead of coffee he got out a bottle of whiskey and two glasses and poured us each one and I started telling my story. First of all I told him that I really did love his daughter. Then how I

Posted by a TS / CD

By OspreyGrove7318

An Unexpected Family Visit During a Date
I am a bottom sissy who loves pleasing men sexually. I thought I had done it all but last night was a 1st. So last night I had a date with a daddy I have been spreading my ass for for a few months.

Posted by a TS / CD

By Deleted User

Unveiling Secrets in a Marriage Journey
I didn't start out being a CD but ended up becoming one for my wife which than turned into me being full out TS. Amber and I married two years out of high school. She'd never mentioned her

Posted by a TS / CD

By Deleted User

Unexpected Encounter at the Park and Ride
This is back when a certain list named Craig had the hook up page, I put up an ad cd looking for fun ext. Got this one response that peaked my interest 2 guys said they have an SUV with blacked out

Posted by a TS / CD

By Kellieskirt

A Surprising Day Off with Unexpected Guests
I have secretly been bi for years now. I'm 29 and married, but at some point while I was dating my now wife I got curious. At one point I decided to secretly try on one of her thongs and I loved

Posted by a TS / CD

By khead1994

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 82.5k 1.0k 4.7k
#2
Tiffanyheels
Couple Straight Trans
Excited wife self-pleasure 183.2k 2.5k 4.5k
#3
kimorafoxxsexycd
Couple Trans Gay
Gf watched me and her gay friend 167.1k 1.7k 4.0k
#4
KestrelElbow9092
Straight Gay Couple
Innocent flirting continue 85.8k 734 3.7k
#5
butchmax
Couple Gay Straight
It started at home and spread ha 131.5k 856 2.3k
#6
Dedavis
Straight for Gay Straight
Massage studio part three 115.0k 770 2.1k
#7
wally4u
Gay Couple Trans
Drunk Abs Experience I'll Never 4Get! 75.1k 331 2.0k
#8
sissyjamie4daddys
Trans Couple Straight
I love water 88.0k 498 2.0k
#9
Steve
Straight Straight for Gay Gay
Vacation with my Aunt part 1 59.9k 693 1.8k
#10
powers8
Gay Straight Straight for Gay
A fantasy come true 88.7k 678 1.7k
Page 1 of 50 · Showing 1–10 of 500 authors

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