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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 Memorable Hotel Visit with Daddy
It's Cocktober, the month to get as much cock in 31 days as possible. It's the month that daddy's rock out with their cock out. Yummy! I am a nut slut who simply LOVES pleasing top

Posted by a TS / CD

By sissyjamie4daddys

Finding Connection After a Work Injury
I'm a non passable crossdresser. I don't do the wig thingy, or makeup. I do wear slutty clothes under my manly clothes I am a total bottom sissy when I am in my fem clothes. I am bisexual

Posted by a TS / CD

By sissyjamie4daddys

A Surprising Meeting at the Adult Store
Hi it's me again here to tell my story of loving the adult store again I go there of course for cock there today was a black guy with this huge cock at least 9" and very thick I

Posted by a TS / CD

By Deleted User

A Night of Hypnosis at the Gay Bar
So I met a guy here on dl we chatted for weeks he said he was a Doctor and hypnotist and a very kinky dominant man sexually I told him I was a bi submissive bottom guy I told him my darkest fantasies

Posted by a TS / CD

By bslave101

A Night of Surprises at the Gay Bar
So I met a guy here on dl we chatted for weeks he said he was a Doctor and hypnotist and a very kinky dominant man sexually I told him I was a bi submissive bottom guy I told him my darkest fantasies

Posted by a TS / CD

By bslave101

Exploring Public Encounters and Addictions
I am addicted to men. When I am out in public, I don't look at faces. I look to see if they have a nice bulge, a growing tent, any cock movements. I am a cock n cum addicted whore. Plain n

Posted by a TS / CD

By sissyjamie4daddys

A Nervous Encounter: First Time at Home
I was looking at ads on DL a a few days ago n 1 of em caught my attention. It was from a young black stud who was looking for a TS or passable crossdresser to fuck for his 1st time. I replied to his

Posted by a TS / CD

By sissyjamie4daddys

Embracing My True Self: A Journey of Transformation
After 2 failed marriages to woman I transitioned to the female side. I have been trans now for 6 months and I am loving my new life. Most of my fam and circle of friends are open minded, and have

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Hotel Meeting with a Couple
I am strictly dickly. I am 100% gay, a sissy, a crossdressing bottom gurl. I haven't had sex with a woman in years. So I was caught off guard a lil when I got a reply from a m/f couple asking if

Posted by a TS / CD

By sissyjamie4daddys

A Chance Encounter at the Casino
So how was everyone's weekend? I had a fab weekend once again. A sugar daddy who loves bout 6 hours away called me n told me he was going to be in town n wanted to spend some time with me. Daddy

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Evening with Friends and Family
One of my daddy's stopped by Saturday evening with a friend of his. Daddy is a sexy silver haired fuck machine in his early 70s n with the help of a lil blue pill, can fuck for hours. His friend

Posted by a TS / CD

By sissyjamie4daddys

A Surprising Connection Found Through Online Ads
I was looking thru ads on DL n AFF. Saw an ad from a young black stud who was looking for a sissy gurl, so of course I replied. Holy fuck! He sent me a pic of his BBBC, n it was huge!! At least

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Visit from Daddy on a Thursday
I was sitting at home on a lazy Thursday morning, just doing some housework. Bout 1030, there was a knock at my front door. I wasn't expecting any visitors. I opened the door n there stood 1 of

Posted by a TS / CD

By sissyjamie4daddys

A Night Out: Seeking Attention and Connection
I love n enjoy being the center of attention. I am an attention seeking whore. I love the attention I get from men while out at a bar, restaurant, store, the mall, anyplace I am in public or private

Posted by a TS / CD

By sissyjamie4daddys

A Day of Pampering with My Sugar Daddy
I am a very lucky gurl. A sugar daddy took me $hopping n $pending Friday, n sugar daddy pampered me like the lil prissy sissy I am. My sugar daddy surprised me by texting me Wednesday morn to tell me

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Visit to a Local Shop
I got dressed n decided to visit a local porn shop this morning. I had on my tight blue/black dress that hugs my body, stockings n a pair of black 4" cfm heels. I had my dark wig n makeup on. I

Posted by a TS / CD

By sissyjamie4daddys

An Intriguing Home Visit Adventure
The second time i went for a date with a BLACK DOM DADDY it was a home visit at his house. I arrived on time at 800 pm and as instructed prior I walked to the door put on the blindfold then knocked

Posted by a TS / CD

By Deleted User

An Unexpected Connection at the Bar
Bout 8 years a go I met an older man from Craigslist. He is 31 years older than me. He was looking for a sissy to suck his dick a few times a week. He told me he could do everything else, cook,

Posted by a TS / CD

By sissyjamie4daddys

Living with My Supportive Partner: A Unique Journey
A few years ago I moved in with my older daddy who took care of me financially n I took care of him sexually. I became his live in sex toy. Whenever daddy needed me to suck his cock or bend over for

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Visit to Daddy's House
I replied to an ad posted on DL from a daddy who had a 5 day load saved up. After a few exchanges daddy invited me to his house. I knocked n he told me to come in. He was sitting in a recliner porn

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
Gay Straight for Gay Straight
Parking lot kiss 35.2k 634 4.1k
#2
Tiffanyheels
Trans Couple Straight
Crossdressing intimacy in office 78.1k 1.4k 3.2k
#3
KestrelElbow9092
Straight for Gay Gay Straight
Beautiful and Black 24.1k 355 3.1k
#4
cnysub
Gay Trans Straight
Ads on DoubleList 47.9k 530 2.9k
#5
kimorafoxxsexycd
Gay Couple Trans
Very kinky self care 74.7k 1.1k 2.7k
#6
sissyjamie4daddys
Trans Couple Straight
I love water 45.9k 461 1.9k
#7
wally4u
Trans Gay Straight for Gay
Pre-Halloween CD Dress Up! Part 1 52.7k 275 1.8k
#8
Steve
Straight for Gay Straight Gay
Gym kiss pt.2 49.2k 612 1.7k
#9
curiousladyd
Straight Couple Straight for Gay
First really big appendage 10.3k 360 1.2k
#10
powers8
Straight Gay Straight for Gay
Back with Michelle and Lisa 34.5k 351 1.1k
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