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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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A Surprise Encounter with an Unexpected Guest
Posted on double list Dressed ready to play... Got response.. Did some Tina Went and got dressed... Waiting He shows up I'm dressed He comes in and I unzip Him And pull his cock out And

Posted by a TS / CD

By kevannacd

A Surprising Connection with My Roommate
It all started when I moved down south. I was staying with some people and it was fine. One night I was sleeping on the couch and the main man of the house walked through the room from his shower. He

Posted by a TS / CD

By Deleted User

A Thrilling Encounter at the Hotel
I answered an ad on doublelist recently and after a couple emails and a phone call I agreed to meet him at his hotel. I don't travel dressed so I went straight into the bathroom to change and do

Posted by a TS / CD

By brian44

Cuddling Up During Fall Football Weekends
I love fall weather. Nice time to cuddle up with a daddy or 2. Love the weekends when football games are on tv. Love sucking on a daddy cock as he relaxes watching a game. Love it even more when

Posted by a TS / CD

By Deleted User

An Unexpected Encounter in the Bedroom
I undid his pants, and took out his cock. I started sucking his cock. I felt it grow in the back of my throat. His cock felt great. He yelled down to the other guys to take lunch as he started to

Posted by a TS / CD

By Deleted User

An Unexpected Encounter During a House Tour
So i was cruising DL one day looking for a top. I really needed some strange cock immediately. I see an ad that caught my eye. 2 tops looking for sissy bottom. Hey, thats me!! Love my top

Posted by a TS / CD

By Deleted User

A Halloween Costume Adventure at the Mall
So today is October 31st, Halloween!! my favorite holiday, why you ask its because I get to parade around in a sexy costume and no one can say a damn thing. So if you don't know how I look im a

Posted by a TS / CD

By ThiccTrapQueen

A Weekend of New Connections and Fun
Part 2 23 year old CD. They took turns fucking her while I watched. Each one cum inside her pussy. When the last one pulled out, Meg said come here Amber. Lick my pussy clean. I got on my knees and

Posted by a TS / CD

By oldarmy

A Unique Coffee Date with a Couple
I'm 23, 5'11 about #150. Have mid length Black hair. Completely smooth all over. Totally passable when I dress. Perhaps to my advantage, I have a micro penis. When I'm completely

Posted by a TS / CD

By oldarmy

An Unexpected Visit Turns Into a Revelation
I want to thank my ex girlfriend for turning me into a cock loving, cum swallowing slut. It all started about 15 years ago. I was a normal straight 27 year old man who loved women. She was 22,

Posted by a TS / CD

By Deleted User

A Night Out at the Bookstore Adventure
I am a mature crossdresser. I dress head to toe and everything in between. I love the feel of lingerie on my ass, legs, thighs. Slipping my stockinged feet into 3 inch heels sends heat through my

Posted by a TS / CD

By donovan777

A Surprise Encounter During a Home Repair
I recently moved to a new city to be closer to my daddy. He paid for my move, set me up in a nice place. Daddy pays fir eveything. I am a passable crossdresser, with wigs, makeup, fake breasts, and

Posted by a TS / CD

By Deleted User

A Chance Meeting at the Hotel Bar
My fantasy. To be seduced by a CD. I’d be setting outside a hotel doing my reports. When a lady sets down next to me. Her legs are so sexy looking. I glance over and she is so hot. Nice

Posted by a straight man

By Deleted User

A Night of Transformation and Self-Discovery
Episode 1 Crossdresser's Night Out I am a mature, bi married male who loves to dress up in women's clothes. Not my wife's clothes though as I like to dress sexier than she ever does. I

Posted by a TS / CD

By donovan777

Adventures of a Crossdresser and His Lover
I am a semi passable crossdresser. Womans clothes: tight shorts, short mini skirts, short dresses, tight blouses, fake tits, 6 inch heels, stockings, wigs, makeup are my specialty. When im dressed i

Posted by a TS / CD

By Deleted User

Rediscovering Crossdressing and Old Connections
Well - now in my upper 40s I am getting back into crossdressing. I started 20 years ago but quit a couple years ago when my long-term boyfriend of 6 years moved out of state. I was crushed - I had

Posted by a TS / CD

By Deleted User

An Unexpected Encounter at a Country Mansion
I have been secretly crossdressing for about 5 years. I have been told i make a good looking gurl. I dont dress in public. But i do wear womans clothes under my pants and shirt. I work for A as a

Posted by a TS / CD

By Deleted User

An Unexpected Encounter on the Way Home
I am a mature petite passable feminine trans woman that lives 90% of the time as just that. I live the way I feel, a highly energized sexy milf. I get offers for dates from guys in their 20's.

Posted by a TS / CD

By Deleted User

An Unexpected Visit from the Neighbor
I'm 26, a BBW TS. I'm 5'7 #220 and have a nice 8 inch thick uncut cock, fully functional. 36C Breasts pierced. Several tattoos. Mid length Black hair. A very cute face. To my knowledge

Posted by a TS / CD

By oldarmy

An Unexpected Late Night Visit with Friends
There was a petite CD I was getting together with about once a month when my wife was working late. S/he like to suck me hard, then ride me for a while until S/he got hard. When I was about to cum

Posted by a straight man

By FerretUmber7968

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
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I love water 71.4k 487 2.0k
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Got Wife Off Flying To Cabo! 67.0k 308 1.9k
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Straight for Gay Straight Gay
Gym kiss pt.2 53.6k 644 1.7k
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butchmax
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I Guess We Asked for it 82.7k 616 1.7k
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A fantasy come true 82.6k 668 1.7k
Page 1 of 50 · Showing 110 of 500 authors

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