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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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Living Out a Fantasy at the Theater
sorry for any typos as i am not re-reading but just going to offer a stream of thoughts......I am such a slut. I finally got a chance to live out a fantasy last night. My large cock dom met me at an

Posted by a TS / CD

By agr8guy38

A Night Out at the Casino with Daddy
I went on a public date with a daddy. We went to a local casino as daddy was in the mood to gamble. Daddy had bought me a brand new outfit to wear for our date n a pair of earrings. When he picked me

Posted by a TS / CD

By sissyjamie4daddys

A Night at the Bel Air Hotel
I'm a single closeted gay white guy from Orange County, CA. For over a year, all I've done is meet men privately and sucked their cock. And I love everything about giving great head.

Posted by a TS / CD

By johnb

An Unexpected Connection in Bonaparte, IA
i seen a add on here a few years back for a guy looking for bottoms in Bonaparte ia. so i dropped him a note not thinking it would pan out . but i heard back from him and we seem to click. told me

Posted by a TS / CD

By samantha1965

Unexpected Connections at the Dallas Car Lot
Hello there Freakies! Im a Dallas CD, worked in a few car lots around the DFW. I am very effeminate, friendly, and customers loved it! What I've enjoyed the most; is with customers, ex and new

Posted by a TS / CD

By shawty2141

A Newport Daddy's Weekly Visit and Surprise
So I am a TS, I have implants and now 36C nice body and still have shaved 7.5 dick. I live in S OC in Newport and all hot Zaddys are around me. So I place ads on here all the time and there is

Posted by a TS / CD

By occock

Unexpected Encounters at a Group Gathering
OMG!! I just had the wildest kinkiest fuck you could ever imagine!! I love to suck cocks, get my sissy pussy fucked n I love eating ass. Well, I was at a group sexssion n I got my ultimate dream. So

Posted by a TS / CD

By sissyjamie4daddys

Unexpected Visitors During Daddy's Errands
So I have this one older daddy mens who I spend nights with providing him with my mouth n my sissy cunt to fuck. He calls me his special sissy gurlfriend. He is aware that I'm a slut, a VERY

Posted by a TS / CD

By sissyjamie4daddys

A Young Woman's Search for Older Companions
I ALWAYS reply to older daddy mens post. I LOVE me some older daddy mens, I'm such a HUGE sucker for them. But it's mostly a crap shoot, n there are times I get really lucky hooking up with

Posted by a TS / CD

By sissyjamie4daddys

A Mysterious Encounter at a Halloween Party
I am a male I went to a Halloween party, dressed up, like a girl wearing a miniskirt thighs, heels, a wig, and make up I went into this party not knowing anybody I had a couple of drinks was dancing

Posted by a TS / CD

By Deleted User

A Cold Night Encounter in the Garage
It's been rather cold here with the temps staying bout 20 degrees during the day time. I got a text from a local daddy mans who I have sucky fucky time a few times a month. Daddy mans told me

Posted by a TS / CD

By sissyjamie4daddys

A Night Out: Discovering New Desires Together
I remember when I told my girlfriend that I was a crossdresser. She wanted to know everything about it. I told her I had been since young when I took my sisters panties. Now, I have everything

Posted by a TS / CD

By Tiffanyheels

A Night Out at the Club with New Friends
I love being shared n passed round to very horny older daddy mens. The more the merrier, the hornier the better. I'm your typical 55 year old sissy slut who gets all dressed up n dolled up for

Posted by a TS / CD

By sissyjamie4daddys

A Breakfast Date with Unexpected Connections
I was invited out to an all you can eat sausage fest breakfast this morning by 1 of my daddy mens. I met him at a local restaurant for some coffee, breakfast, n to get to know each other a lil bit.

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Visit to Daddy Man's Castle
Daddy mans told me I was exactly what he was looking for. He gave me his addy n a few hours later I was knocking on his front door anticipating that soon daddy mans would be pounding on my back door.

Posted by a TS / CD

By sissyjamie4daddys

A Journey of Self-Discovery Through Dog Sitting
Dog and House Sitter (Part1 – Stephen) Background about myself, Stephen. I had a high heel fetish for a long time; looking at sexy heels and boots in pictures and on women. I finally got the

Posted by a TS / CD

By pickleballed

Exploring Local Adventures in Public Spaces
I love n enjoy sucking strangers off at parks, clubs, grocery stores, you name it. I love it. I love getting that sweet tasty load of cum, coating my throat as I swallow every drop draining those cum

Posted by a TS / CD

By sissyjamie4daddys

A Mysterious Encounter at the Restaurant
I responded to an ad posted by an older daddy who was looking for a young lil sissy slut. Daddy agreed to meet me at a local restaurant at 10 pm. I got all dolled up, wig, makeup, lil.mini skirt,

Posted by a TS / CD

By sissyjamie4daddys

Unexpected Meeting in a Chicago Hotel
I dress completely from head to toes. I’m very feminine and I absolutely love to take a nice thick big cock in my ass I prefer BBC but this one time I had an encounter with this white man he

Posted by a TS / CD

By jadafir3

Exploring New Boundaries Together in a Theater
I am a passable crossdresser. Shaved all over, silicone breasts and the works. Jewelry and perfume to top it all off. My girlfriend loves it when I am dressed. In fact, she gets off watching me suck

Posted by a TS / CD

By Tiffanyheels

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 Gay Straight for Gay
35 years later 43.3k 678 4.2k
#2
Tiffanyheels
Trans Couple Straight
Girlfriend and crossdresser 92.1k 1.6k 3.3k
#3
KestrelElbow9092
Gay Straight for Gay Straight
Rare Saturday 32.7k 409 3.2k
#4
kimorafoxxsexycd
Gay Couple Trans
Gay entertainment is hot 93.5k 1.2k 3.0k
#5
cnysub
Gay Trans Straight
Cruising in the Woods at the Gay Nature Campgrounds 57.1k 587 3.0k
#6
sissyjamie4daddys
Trans Couple Straight
I love water 56.3k 466 1.9k
#7
wally4u
Gay Trans Straight for Gay
From A Gay Bar To A Spa! 56.0k 278 1.8k
#8
Steve
Straight for Gay Straight Gay
Gym kiss pt.2 51.3k 624 1.7k
#9
butchmax
Gay Couple Straight
She figured it out and changed my life 52.5k 437 1.2k
#10
powers8
Straight Gay Straight for Gay
A task I'll never forget 41.4k 397 1.2k
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