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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 Surprising Meeting at the Local Store
Stopped at the local porn store to pick up some din din. When I went in there was bout 6 others inside. I walked up to the counter n payed my way for a booth. Next thing I heard was this fine as fuck

Posted by a TS / CD

By sissyjamie4daddys

A Discreet Encounter at Home
I answered a DL ad for Dom Daddy wanting a sissy crossdresser cumslut. I answered the door dressed up super sexy, and invited him in. Now I'm married, so have to be discrete but when I saw

Posted by a TS / CD

By Deleted User

Kissing Booth Adventures at a Pride Event
I love me top daddys that love n I mean LOVE to kiss n make out. Passionate daddys that love kissing n cuddling. Id rather do a circle kissing than a circle jerk. So when a local bar had set up a

Posted by a TS / CD

By sissyjamie4daddys

Late Night Texts from Daddy Men
My booty caller goes off all the time with texts from daddy mens that need a lil sumthing, be it a piece of ass. Or some sucky sucky. It don't matter time or day, or time if day. 1pm, 530pm,

Posted by a TS / CD

By sissyjamie4daddys

A Surprise Visit from a Mysterious Friend
Met a Dom Top Daddy last week on DL. He came over to my house when the wife was at work. I met him at the door dressed sexy, fuck me pumps and mini skirt and full makeup. I dropped to my knees

Posted by a TS / CD

By Deleted User

An Unexpected Visit from the Tech Installer
AT&T was sending a tech over to install internet at my house. Married discreet cd. I would dress up when my wife left for work. I woke up one morning jumped out of bed and started picking out

Posted by a TS / CD

By Almabebe

A Journey of Self-Discovery and Connection
I was straight until 60 years old. Took out an add asking for someone to take my V card. I visited a man and let myself into his apartment. He was sort of drunk and waiting for me in his bed naked

Posted by a TS / CD

By Lipgloss

A Goth Girl's Journey to Self-Confidence
It was back in the summer of 2025, I'm a Transgender Female MTF Pre-op aspiring goth gurl. Although I'm 49 year's old I have been told that I look very young for my age. It's the

Posted by a TS / CD

By Deleted User

A Journey of Escape and Discovery
It seems like the only time I have any luck is when I’m running away from a home that feels like I’m always abducted, the first time I ran away I’ll be honest i was on a Mission or

Posted by a TS / CD

By altalias_t

An Unexpected Encounter in a Delivery Van
I started working for this place. One of my coworkers was also one of my ex wifes fuck buddys. So like one day him n I had to delivery some things bout 1.5 hour away. Now I always thought he was a

Posted by a TS / CD

By sissyjamie4daddys

A Night Out at the Dance Club
There I was dressed in a very nice red dress. Short but looked good on me. I was thinner back then and could slide into a size 10 dress. This was a one piece and zipped up the back. I wore white

Posted by a TS / CD

By ardee1x1

A Journey of Longing and Unexpected Encounters
1,2 maybe 3 really large black men come into my path for one thing, to fuck like that couldn't ever fuck again after this there final fuck I mean deep raw fucking, I way h born every day and

Posted by a TS / CD

By Deleted User

Unexpected Hotel Fantasy Encounter
I was just traveling for my job it takes me to different places often. I always have been secretly dressing up like a total sissy completely submissive so I had planned to use my hotel as a perfect

Posted by a TS / CD

By sismissy

An Unexpected Encounter at the Bookstore
I was at my local adult bookstore sucking cocks in a booth. Now I'm an older crossdresser who is strictly dickly, a total n complete bottom prissy sissy. I'm a cock gobbling, cum guzzling,

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Encounter in the Backwoods
I got on sniffies tonight, lots of flakes per the usual . It was getting late and someone sent me a message. They were 27 (I'm 43) 6ft 4in and 400+lbs with a 6.5" cock. We went through the

Posted by a TS / CD

By GannetShard4708

An Unexpected Massage Encounter with a New Friend
Met a Feminine Fat Top on CL. He invited me to massage him. Powerful neck and back kept me busy as he moaned from my aggressive unrelenting servitude. Big ass to rub. Powerful thigs in my hands to

Posted by a TS / CD

By Deleted User

A Late Night Visit Changes Everything
I had always been a straight cross dresser. One night changed that. I was home one night, dressed up and ready for bed. I’m laying on my stomach reading, with my earbuds on. Wearing a teddy,

Posted by a TS / CD

By rylie19

A Journey of Trust and Exploration Together
I have been happily married for many years but, as I have gotten older, I have started enjoying crossdressing when I have the opportunity. Fortunately, I have a very understanding wife who not only

Posted by a TS / CD

By dclark

Exploring Connections with Local and Out-of-Town Daddies
I have been out prancing n wiggling my lil sissy ass off for men for the past 8 years. Before that, I acted n pretended to be straight. I didn't have a gay bone in my body. Now, I have straight

Posted by a TS / CD

By sissyjamie4daddys

Unexpected Encounter in the Grocery Lot
So I got stood up the other night. Had emailed, texted, n exchanged pics n vids with a potential daddy mans for a few days. Daddy mans wanted to meet so bad. Told me he wanted to give me a good

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 34.0k 625 4.1k
#2
Tiffanyheels
Trans Couple Straight
Crossdressing intimacy in office 76.4k 1.4k 3.2k
#3
KestrelElbow9092
Straight for Gay Gay Straight
Beautiful and Black 23.2k 353 3.1k
#4
cnysub
Gay Trans Straight
Ads on DoubleList 46.1k 521 2.9k
#5
kimorafoxxsexycd
Gay Couple Trans
Very kinky self care 71.2k 1.0k 2.7k
#6
sissyjamie4daddys
Trans Couple Straight
Sucking appendage in the club 43.7k 456 1.9k
#7
wally4u
Gay Trans Straight for Gay
From Zorbas To His Hotel Room 50.1k 272 1.8k
#8
Steve
Straight for Gay Straight Gay
Gym kiss pt.2 48.0k 604 1.7k
#9
curiousladyd
Straight Couple Straight for Gay
First really big appendage 9.9k 357 1.2k
#10
Dedavis
Straight for Gay Straight
House hunting pt 1 37.9k 276 1.1k
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