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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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An Unexpected Connection with a Workout Partner
I read a post from a young stud who was looking for a "queer feminine guy to work out with". I responded to his ad n he invited me over to his place. He was very muscular. OMG n sexy! He

Posted by a TS / CD

By sissyjamie4daddys

A Night of Intimacy and Connection
Laying in bed with a daddy dick in my ass. God daddy's dick feels so good. Daddy pumping away, burying that dick of his, hitting the right spots. Then daddy pulls out n straddles my face, his

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Connection at the Bar
Met a nice young stud last night at a bar. He is early 20s with a nice curved cock. He walked up to the table I was sitting at with 1 of my older daddys. The young stud asked if me n daddy were

Posted by a TS / CD

By sissyjamie4daddys

A Morning Coffee Meeting with a New Sugar Daddy
I'm a happy lil bitch this morning I met a new sugar daddy yesterday. His name is Sam, an older married local businessman who is very 🤑💰 wealthy. I met him thru a diff site. We spent most

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Visit from an Old Friend
The ad was simple n straightforward: 'married male not getting any at home. Need a feminine guy to take care of my pipe weekly'. I responded, we exchanged pics, he was at my house 2 hours

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Visit from Young Friends
Oh my fucking ass pussy just got double stuffed again n it felt fucking amazing!! I was in bed sucking a sugar daddys cock just sugar daddy n me this morning after a long night of fucky sucky time. I

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Night Out with New Friends
I'm a size queeny sissy gurl always looking for the next big cock to suck or fuck my lil ass pussy to stretch me the fuck out. I have had the honor of sucking on some of the biggest thickest

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Encounter at the Club
Monday evening I decided to go on a cock hunting expedition to a local HEY club. I was a lil buzzed so I called an Uber to take me to the club. I got to the club bout 7ish. There were prolly bout

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Connection at Home
I responded to a post from a 53 year old top. He is in a sexless marriage n he was looking for a gurl to meet with twice a week. We exchanged some small chat, digits n a few pics. He liked what he

Posted by a TS / CD

By sissyjamie4daddys

A Surprise Visit from Daddy After Months Apart
Daddy called me n told me to have my sissy ass ready by 700 that he was in town for a few days n that he needed to get some ass from me. I took a shower, douched, shaved n got dressed in a lil red

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Visitor Changes Everything
How did I become a cock craving, cock sucking, cock riding sissy slut? I didn't start out this way. I was a 'normal' boy growing up. I had girlfriends in high school. I got married

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Meeting at the Bookstore
I stopped by a local adult bookstore yesterday to get something to eat. When I got there there were just a few cars in the lot. I parked n made sure my makeup was on point. I walked in, and was

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Encounter with My Ex-Wife
When I first asked my ex wife about me cross dressing she wasn’t really into it so she said you can but you have to do something for me if you really want to ! I quickly said sure anything and

Posted by a TS / CD

By Deleted User

Exploring a Unique Fantasy Delivery Role Play
So I read lot of the stories post a few post with no luck all are older guys not fens or ts one replied that really got me rock hard looking at her pic nice big round ass in air want me to deliver

Posted by a TS / CD

By bignutjj

An Unexpected Visit from My Sugar Daddy
This happened yesterday n I just had to share. I am a somewhat passable crossdresser. My lil nubby don't work. I dress completely as a fem, act n talk very fem. I wear wigs makeup n a breast

Posted by a TS / CD

By sissyjamie4daddys

A Unique Encounter with Heels and Feet
I love my feet the way they look smell taste and feel been licking and selling them all my life other people done it for me too they always have a different aroma and my feet sweat when I wear close

Posted by a TS / CD

By lovemyfeet

Reflecting on Memorable Bookstore Encounters
Hey. First of all I simply LOVE LOVE reading all these fabulous stories that are posted on here. They bring back some memories of things I have done: sucking cocks in adult bookstores, the sex, back

Posted by a TS / CD

By sissyjamie4daddys

Adventures in a Hotel Room Encounter
I love dressing slutty in a hotel room and advertising on DL for some BBC. I usually start around 10 am. Well, one day, my first guy came in and was instantly hard with a big 10-inch cock. I went

Posted by a TS / CD

By EagleQuartz5354

A Sweet Encounter at the Coffee Shop
I love the company of older top Daddys that are a lil kinky. I had the honor of providing my sucking services to an older daddy yesterday n I hope to serve n service daddy again. I met daddy at a

Posted by a TS / CD

By sissyjamie4daddys

A Greedy Encounter with Daddies
I have become.a greedy lil cock sucker. As soon as I get my lips around a cock, and I feel it growing in my mouth, I don't stop sucking til I get that sweet hot fresh man juice, that hot creamy

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
Tiffanyheels
Trans Couple Straight
Crossdresser and girlfriend 79.3k 1.4k 3.2k
#2
KestrelElbow9092
Gay Straight for Gay Straight
Careful what you wish for. 25.2k 357 3.1k
#3
cnysub
Gay Trans Straight
Ads on DoubleList 48.7k 544 2.9k
#4
kimorafoxxsexycd
Gay Couple Trans
New life as a gay man 76.8k 1.1k 2.8k
#5
sissyjamie4daddys
Trans Couple Straight
I love water 47.4k 461 1.9k
#6
wally4u
Trans Gay Straight for Gay
Pre-Halloween CD Dress Up! Part 1 53.7k 276 1.8k
#7
Steve
Straight for Gay Straight Gay
Gym kiss pt.2 49.5k 616 1.7k
#8
curiousladyd
Straight Couple Straight for Gay
First really big appendage 10.5k 360 1.2k
#9
powers8
Straight Gay Straight for Gay
Back with Michelle and Lisa 35.0k 354 1.1k
#10
Dedavis
Straight for Gay Straight
House hunting pt 1 38.3k 277 1.1k
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