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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 Weekend Retreat in the Woods with Friends
I love playing with groups of men, 3 or more. I adore being the main attraction, the center of attention, the main entertainment for them. I attend at least 3-5 group sexssions a week. The most I

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Visit from Daddy's Friends
I was scrolling thru some postings on DL n AFF earlier today. One post caught my attention. It was from an older daddy mans n 3 of his friends looking for a place to play. After a few exchanges, I

Posted by a TS / CD

By sissyjamie4daddys

A Spooky Halloween Date Night Adventure
so Halloween was a blast finally getting to write this it was a bit cold where i live but went out dressed up in my little pink pleated skirt matching crop top with my false breast on had pink and

Posted by a TS / CD

By ababycd

Exploring Fantasies Through Online Connections
Am 30 I met a sweet man from double list we have been talking for almost two weeks , am a lovely sweet trans girl I made him cum always we had fun and he told me about his fantasy he wants 3 some

Posted by a TS / CD

By tliab

An Unexpected Visit from a Younger Guy
hi its Josey again and i am seen a guy with a 10" cock and i can't get enough of it. he is a little younger than me and black but i love big cock so color blind, but he came to see me here

Posted by a TS / CD

By greatime00

A Surprise Visit from My Neighbor
So today while my gf was at work I got dressed up looking cute for a cross dressing woman such as my self. Well today I decided to text my straight neighbor who likes me well I went to his house soon

Posted by a TS / CD

By kimorafoxxsexycd

An Unexpected Evening with a New Guest
I invited a guy over to my house. I didn't know this guy. It was my first time inviting someone over. I got dressed up in a black mini dress. I was wearing a black lace garter belt with black

Posted by a TS / CD

By Miniho

An Unexpected Invitation to a Country Gathering
I am a young trans in my late 20's, I guess I have daddy issues because I like older guys, with no upper age limit. I post on DoubleList for older guys into young submissive trans gurls. I get a

Posted by a TS / CD

By cnysub

A Hidden Side: Crossdressing and Unexpected Romance
So last weekend I was looking cute had my hair done nails and makeup right with this cute dress and thigh high boots wile my gf was at work she has no clue I love cross dressing as a woman and that

Posted by a TS / CD

By kimorafoxxsexycd

An Unexpected Adventure in the Countryside
Back when craigslist was still a thing, I was posting looking for a meet up. I was very inexperienced. i eventually found a guy who seemed really keen. He lived out in the rural areas of a big city..

Posted by a TS / CD

By yorkscd

Embracing Authenticity: A Journey of Self-Discovery
I came out 8 glorious years ago. I was broke in, turned on, n turned out by a much older top daddy. He showed me what I have been missing for 40+ years. I was 47 when I stopped acting, n pretending I

Posted by a TS / CD

By sissyjamie4daddys

A Nervous First Encounter in a Hotel Room
My first time getting fucked. I had been with men before at my hotel rooms as I traveled for work. Mostly just sucking them off or letting them shoot thier loads all over my sexy panties. Then I

Posted by a TS / CD

By ardee1x1

A Surprise Visit and a New Connection
Gf was at work out town she has no clue I love cross dressing and I'm bisexual so I decided to get cute and be the woman I was born to be. Whole she was out of town I took the opportunity to

Posted by a TS / CD

By sexycdkimfoxx

A Halloween Night Adventure at the Theater
I never went out in public dressed, I can't pass. So I figured the best day to go out dressed is on Halloween night. I did my make-up and my hair, I am lucky I have my own ponytail, put on thigh

Posted by a TS / CD

By cnysub

An Unexpected Visit from My Stepson
I thought my stepson had left work work, as usual. I was laying on my bed masturbating and heard a noise, opened my eyes and saw him standing in the doorway looking at me and rubbing his crotch. I

Posted by a TS / CD

By charleyandsnickers

A Sassy Night Out Adventure
I am NOT gurlfriend material. I am more of a sissy gurl for ALL top men. I love sucking cocks and getting my sissy ass fucked deep and hard. I dress like a slut, ALWAYS prepared for any top daddy

Posted by a TS / CD

By sissyjamie4daddys

A Journey into Cross Dressing and Connection
I was a late bloomer. My entry into the world of cross dressing began when I turned 60 years old. I gleaned underwear from all sorts of places. Most of it was trashy. But at some point I began

Posted by a TS / CD

By Lipgloss

Finding My True Self in Love
I love mens bods. Always have n always will. I tried the "straight lifestyle" but it grossed me out. I dated a woman for bout 2 months but realized that I was made to be with, n made for

Posted by a TS / CD

By sissyjamie4daddys

Unexpected Connections at a Local Motel
i have really tried to stop sucking strange guys cock but i am a complete failure i just cannot help but to want strange men cum i love the stuff i need it so i got my clothes ready and packed and

Posted by a TS / CD

By greatime00

Exploring Unique Connections with Daddy Figures
I love the smell of daddy mens bods. I enjoy using my mouth my lips n my tongue to explore..OMG! It is an incredible feeling giving daddy mens a nice long tongue massage. I always stop n take my time

Posted by a TS / CD

By sissyjamie4daddys

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 44.2k 687 4.2k
#2
Tiffanyheels
Couple Trans Straight
Girlfriend loves movie theaters 94.8k 1.6k 3.4k
#3
KestrelElbow9092
Gay Straight for Gay Straight
Rare Saturday 33.7k 416 3.2k
#4
kimorafoxxsexycd
Gay Couple Trans
Gay entertainment is hot 94.8k 1.2k 3.0k
#5
cnysub
Gay Trans Straight
Cruising in the Woods at the Gay Nature Campgrounds 57.8k 590 3.0k
#6
sissyjamie4daddys
Trans Couple Straight
I love water 58.0k 467 1.9k
#7
wally4u
Gay Trans Straight for Gay
From A Gay Bar To A Spa! 56.5k 278 1.8k
#8
Steve
Straight for Gay Straight Gay
Gym kiss pt.2 51.5k 627 1.7k
#9
powers8
Straight for Gay Straight Gay
A night to remember 44.8k 423 1.2k
#10
butchmax
Straight Gay Couple
I didn't get promoted ha 54.4k 450 1.2k
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