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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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Category: TS / CD

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Unexpected Meeting at the Mall Food Court
I met a younger Black Man at the.mall last Thursday. He had posted on here that he wanted to hook up with an older white crossdresser, who was feminine. Thats me😁. I crossdress 24/7, and live as a

Posted by a TS / CD

By Deleted User

A Surprising Meeting at the Alternative Bar
My boss is a handsome Black man in his mid 50s. I am a closeted crossdresser who has only dressed at home and for hookups. My boss was telling me about his recent vacay to Dallas and the bar he

Posted by a TS / CD

By Deleted User

An Unexpected Anonymous Encounter at Home
I am a chubby trans man and back when I was still very new to the site I made an ad that I wanted someone to pound my ass. I waited and finally got a reply from a man with a big thick dick. I told

Posted by a TS / CD

By icantakeit123

Unexpected Encounter in the Parking Lot
I got a text from a number I did not recognize. It read: can you meet me in the parking lot at Lowes. I asked who this is. He said a friend of Dra, a young Black Man that slings a mean cock. I told

Posted by a TS / CD

By Deleted User

Unexpected Meeting in the Walmart Parking Lot
I put an add up. I havent had any cock for weeks. A few minutes later a gent gave me who he was and wanted. He wanted to meet bi the bi at ramp just a few minutes from me. I told him what I would be

Posted by a TS / CD

By guysjustwannahavefun

Unexpected Connections During a Business Trip
I am a very open, bi mwm with a nice 7" cut cock and a fat mushroom cockhead. I only dress when i go on business trips as my wife is not fond of my kink although she is well aware of it...with

Posted by a TS / CD

By desertshooter

A Cozy Evening with a Gay Couple
Last week, I met up with a young gay couple at their place for some hot group sex. I am a prissy sissy crossdresser, who is ALL bottom. I had hooked up with this couple a few times in the past. This

Posted by a TS / CD

By Deleted User

A Nervous First Encounter at His Place
I created a posting looking for a top. Oh how I found what I wanted. It was my first time virgin experience with a guy. I was so nervous, but I went ahead with the plan, met him at his place. He let

Posted by a TS / CD

By Deleted User

Exploring a Unique Marriage Arrangement
I made a deal with my older hubby while we were dating: I will fuck and suck any man I want, in exchange I will give him some head or pussy 1 time a month. He agreed to it. My hubby is 72 years old.

Posted by a TS / CD

By Deleted User

Navigating Love in an Open Marriage
So I met this young Black Man on here about 9 months ago. He has an amazing body, and cock for me. He is 26, muscular body, nice 9 inches of BBBC and knows how sling that cock, loves to fuck, has

Posted by a TS / CD

By Deleted User

An Unexpected Visitor and a Secret Encounter
I will never forget my 1st bisexual sexperience. It was 27 years ago. I was 21, and just recently married to a woman. She worked 3rd shift, so I was home alone. I was sitting in the living room,

Posted by a TS / CD

By Deleted User

A Crossdresser's Journey to Find Connection
You can't be first, but you can and will be next, is what I have told top daddies since I have been in the lifestyle. I am a 48 year old crossdresser who is married to a much older man. He is 72

Posted by a TS / CD

By Deleted User

A Chance Meeting at the Park Path
I love and enjoy public play. The risk of getting caught sucking cock, or riding a cock is such a fucking adrenaline rush. Its a natural high for me. I met a man at a park the other day. He was

Posted by a TS / CD

By Deleted User

Unexpected Encounter in a Parking Lot
I am strictly dickly. I am 100% all bottom. I am as feminine as a natural born female. But the ad intrigued me to the point I had to respond. Turns out, it was not a fake, but a real ad that read:

Posted by a TS / CD

By Deleted User

An Unexpected Visit to a Friend's House
So i started wearimg my moms panties and bras as a pre teen. As i got oto my teens id take my friends moms or sisters panties especially if they were in the dirty pile. I loved that smell. I got

Posted by a TS / CD

By kaylacd35

A Sunday Morning Surprise with New Friends
There is no better way to wake up on a lazy Sunday morning than having a sausage breakfast, man sausage that is. Saturday night, my hubby took me to the club. I met 2 younger hot studs, and after the

Posted by a TS / CD

By Deleted User

An Unexpected Surprise Visit from My Boyfriend
I got a text from 1 of my boyfriends who said he would stop by after work the next morning, and that he had a nice lil surprise for me. I couldn't wait to see him. He is a younger Black Man with

Posted by a TS / CD

By Deleted User

Unexpected Reunion at the Hotel
FTM/cis guy daddy/son roleplaying He told his wife he was going to Costco. I told mine I was going to Target. Neither of us were interested in shopping. I got to the hotel first, a chain brand

Posted by a TS / CD

By Deleted User

A Special Evening of Transformation and Connection
I have been bi many years. I also dress as a woman alot. I can pass as a woman and dress very sexy too. I can that sexy woman on a street corner or be that executive secretary (which is my favorite)

Posted by a TS / CD

By OlderMaleguy

Searching for the Perfect Match: An Unexpected Meeting
I have this list of men I've been creating on DL. I'm in search of perfect guy for me. One my height 6'4" and not much heavier. No more than 240lbs. Sorry guys. Oh and someone

Posted by a TS / CD

By Justme

Top Authors

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

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