Sponsored

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.

Category: TS / CD

Sort by

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 Deleted User

21

Listen Read More

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

10

Listen Read More

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

10

Listen Read More

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

3

Listen Read More

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

10

Listen Read More

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

3

Listen Read More

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 Deleted User

16

Listen Read More

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

6

Listen Read More

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

2

Listen Read More

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

4

Listen Read More

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

2

Listen Read More

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

11

Listen Read More

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

1

Listen Read More

An Unexpected Visit Leads to Surprises

This happened to me yesterday. One of my daddy mens was over n we were on the couch as he was slamming his cock into my sissy cunt. I was fucking on it feeling his balls slap against my ass. I was in

Posted by a TS / CD

By sissyjamie4daddys

1

Listen Read More

Complicated Family Dynamics in the 70s

This story is from 1972 my mom married a man that had 2 daughters from Indiana that were lil sluts and wild any way they moved in flirting the oldest Kim had big tits and the young er was Tracy and

Posted by a TS / CD

3

Listen Read More

A Sweet Reunion with Daddy Mans

I have one of my daddy mens visiting me for a few days. His flight got in yesterday n he drove right out to my house. When I saw daddy mans I rushed over n we kissed as his hands grabbed my tittys n

Posted by a TS / CD

By sissyjamie4daddys

1

Listen Read More

A Night at the Bondage Party

I met this Dominate Crossdresser at a bondage and S&M party, I'm a 27 yr old bi male. she is older in her late 40's still sexy and totally passable. We played that night, she really

Posted by a TS / CD

By Deleted User

11

Listen Read More

Summer Gatherings at a Country House

I live bout 20-25 minutes from the city. I live in the country on 5 acres n my closest neighbors are a good 1/2 mile down the road. I have a nice 3 bedroom house, big yard with a 8' privacy

Posted by a TS / CD

By sissyjamie4daddys

4

Listen Read More

A Night of Fashion and Fantasy

Why do we like the things we like. Is it something in our upbringing or are we all just born that way. Who’s to know, but for me my enduring kink is having sex with cross dressers. My

Posted by a TS / CD

12

Listen Read More

A Heartfelt Hospital Visit with Daddy Mans

I got a text the other day from one of my local regular daddy mans. He had fell down some stairs n was in the hospital. He asked me if I would come up to visit him. I told him I would be happy to

Posted by a TS / CD

By sissyjamie4daddys

5

Listen Read More

1..39 40 41...170

Top Authors

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

RISING AUTHORS ON DOUBLELIST See all

L LucyV “I'm a romantic trans woman” U uhostshysub “what do you have for homework?” I itshugetwink “🔒🍑 Asian Billionaire Bus And He Begged Me To Stay — Asian Daddy Part 1”

Daze “Just a real woman looking for love ❤️”

Rank	Author · Category	Latest Story	Views	Listens	Upvotes	Trend
#1	derake14 Gay Couple Straight for Gay	First true anonymous intimacy	77.7k	1.0k	4.7k	↘
#2	Tiffanyheels Straight Couple Trans	Intimacy with ex mother in law	174.6k	2.4k	4.3k	↗
#3	kimorafoxxsexycd Trans Gay Couple	Intimate Somali man	157.8k	1.6k	3.9k	↗
#4	KestrelElbow9092 Gay Straight Couple	Closet kicked in.	79.1k	679	3.6k	↗
#5	butchmax Straight Gay Couple	My Husbands Best Friend	119.9k	813	2.1k	↘
#6	wally4u Gay Couple Trans	Drunk Abs Experience I'll Never 4Get!	73.6k	330	2.0k	↘
#7	Dedavis Straight for Gay Straight	Super Bowl group event part six	102.6k	706	2.0k	↗
#8	sissyjamie4daddys Trans Couple Straight	I love water	84.7k	496	2.0k	↘
#9	Steve Straight for Gay Straight Gay	Doublelist fan	57.7k	677	1.8k	↘
#10	powers8 Gay Straight Straight for Gay	A fantasy come true	87.6k	678	1.7k	↘

Page 1 of 50 · Showing 1–10 of 500 authors

How To Share Your Trans Erotic Story

Here’s how to use DoubleList to post transgender stories:

Discover More Transgender Sex Stories on DoubleList

Are you looking for more shemale sex stories to get the mood going? Or do you also want to be a part of the community and share your experience? Join DoubleList for free, and within minutes, you’ll unlock a world of sexual pleasure

Read more stories or browse through our countless listings to find the casual encounter of your dreams. Join our adventurous community today and see who’s ready to fulfill your desires!