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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.

Category: TS / CD

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Unexpected Encounters at the Adult Theater

I am a bi crossdresser, but today I went to an adult theater without being dressed as a woman. I started watching shemale movies in one theater, which got me very hard. Then I went in the gay

Posted by a TS / CD

By Tiffanyheels

5

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A Unique Holiday Game Night Experience

I was invited to a daddy mans house for a special XXXmas game night. My daddy mans told me to wear something festive for the holly day season. I decided a short lil green skirt, a low cut red top to

Posted by a TS / CD

By sissyjamie4daddys

2

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An Unexpected Evening of Transformation and Surprise

I posted a add for a female to help me dress as a female as I wanted to feel sexy for a Saturday evening. I had a a response from a older lady that said her and best freind had always talked about

Posted by a TS / CD

8

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A Night of Shared Adventures Among Couples

I live to lick a pussy that has been just filled with another man’s cum! Since my wife and I are swingers, I have done this many times. I also love to lick my own cum out of a pussy When we

Posted by a TS / CD

By Tiffanyheels

6

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An Unexpected Encounter in a Boston High-Rise

It started off with this women contacting me saying they needed a no limit sissy who knows her role as a submissive bitch for a 4-6 hour session. which instantly got me excited but she wouldn't

Posted by a TS / CD

By Deleted User

1

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Exploring the Unique Bond of a Sissy Gurl and Her Daddy

I have been crossdressing n living my life as a sissy gurl for the last 8 years. I am NOT trans. But I do have 38DDs tittys that my daddy mans got for me 7 years ago. I still have my lil teeny tiny

Posted by a TS / CD

By sissyjamie4daddys

1

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Unexpected Performance at a Bachelor Party

Soo 2 weeks ago this black man called me and said he looking to hire 2 girls and 1 sissy gurl for a bachelor party of 14 guys all black and they were looking for a complete no limit slut which they

Posted by a TS / CD

By Deleted User

4

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An Unexpected Encounter at the Theater

I had been crossdresser since age 12-13. Love to masturbate wearing my sisters things. Then started going to adult theaters. Then one night I went in a booth without doors. I put on a shemale movie

Posted by a TS / CD

By Tiffanyheels

5

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Adventures on the Open Road with Daddy

So I love giving road head to any daddy mens. I have been giving road head for years n in my opinion there is nothing better. Just get into a car with daddy mens, sit in the front seat n reach over

Posted by a TS / CD

By sissyjamie4daddys

0

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An Unexpected Gathering with New Friends

So I got my lil sissy ass invited to a group sexssion yesterday by one of my local daddy mens. Talk bout a lot of fun!! There were 7 daddy mens plus my man, me n this really cute lil twinky. I have

Posted by a TS / CD

By sissyjamie4daddys

3

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Festive Outfits and Friendly Encounters

Just relaxing after a long day of Christmas shopping. The stares n the compliments I got from people. People are so friendly this time of year. I decided to put on my lil Christmassy outfit: green

Posted by a TS / CD

By sissyjamie4daddys

3

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An Unexpected Meeting at the Hotel Room

So i responded to a young stud who wanted a sissy slut to stop by his hotel room. He had a Sybian n a fuck machine that he wanted to use on my sissy cunt. He told me if I was interested I could also

Posted by a TS / CD

By sissyjamie4daddys

6

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Unexpected Encounters at the Nightclub

There's an old saying: you can't turn a whore into a housewife. N that is so fucking true! No matter what your intentions are, a whore is a whore IS A WHORE! N she will ALWAYS be one. How

Posted by a TS / CD

By sissyjamie4daddys

1

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Flirty Encounters at the Local Club

I always believed that being bisexual just means that you double your chances of getting laid. But I have realized that men are the only ones that want to play n that is fine with me!! Men are better

Posted by a TS / CD

By sissyjamie4daddys

3

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A Journey of Transformation and Love

My very first time sucking a man's cock, I knew I was addicted! OMG what an incredible feeling. He was a family friend of my grandfather's. He was in his mid 60s, I was 21. His cock tasted

Posted by a TS / CD

By sissyjamie4daddys

9

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Unexpected Encounters at the Local Shop

Stopped at a local porn shop earlier tonight. When I pulled onto the parking lot, there was 5-7 cars. Kinda bizzy for a Monday. I got out of my car, n walked into the shop. I noticed 5 daddy mens

Posted by a TS / CD

By sissyjamie4daddys

3

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A Unique Coffee Meeting with My Master

Submissive lil sissy slut here. I love bowing down n servicing strong alpha men. I am collared n lead round my masters house on leash. My master is always naked n waving that big cock in front of me.

Posted by a TS / CD

By sissyjamie4daddys

6

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A Journey of Love and Transformation

Bobbie, PART TWO: It felt beautiful when he started tongue fucking me, he reached between my legs and started stroking my cock. With him stoking me and tongue fucking me I came hard. It felt

Posted by a TS / CD

9

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Exploring a Unique Club Experience Together

When my daddy Les broke me in, n turned me out, there was a club bout 30 minutes from our house that he would take me to to "get seasoned" as he put it. This club used to be a huge

Posted by a TS / CD

By sissyjamie4daddys

4

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An Unexpected Encounter with Daddy

Brought home something really good to eat last night. Daddy mans is bout 6'4", 225 pounds of major muscle, big broad chest n shoulders, n a sweet 10" of pure chocolate cock for this

Posted by a TS / CD

By sissyjamie4daddys

2

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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 lynn999 “Am available for enjoyment” 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”

Rank	Author · Category	Latest Story	Views	Listens	Upvotes	Trend
#1	derake14 Gay Couple Straight for Gay	First true anonymous intimacy	77.4k	1.0k	4.7k	↘
#2	Tiffanyheels Straight Couple Trans	Intimacy with ex mother in law	173.7k	2.4k	4.3k	↗
#3	kimorafoxxsexycd Trans Gay Couple	Intimate Somali man	157.5k	1.6k	3.9k	↗
#4	KestrelElbow9092 Gay Straight Couple	Closet kicked in.	78.3k	676	3.6k	↗
#5	butchmax Straight Gay Couple	My Husbands Best Friend	119.6k	813	2.1k	↗
#6	wally4u Gay Couple Trans	Drunk Abs Experience I'll Never 4Get!	73.3k	330	2.0k	↘
#7	sissyjamie4daddys Trans Couple Straight	I love water	84.6k	496	2.0k	↘
#8	Dedavis Straight for Gay Straight	Super Bowl group event part six	102.5k	706	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	87.5k	678	1.7k	↘

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