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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.

Category: TS / CD

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Unexpected Romance with My Office Assistant

Met this transgender woman here went over to her place and damn she was hot puerto rican number. She had the firmest tiny tits when I took her bra off I ran my hand down to her red silk and lace

Posted by a straight man

By stormyhunter141_e6dabe

1

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A Night of Unexpected Wardrobe Experimentation

I had never dressed in women's clothing before but one night my girlfriend was gone for the night and for some reason I had the urge to try on a pair of her sexy panties. To my surprise it

Posted by a TS / CD

By availablenow49009

0

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An Unexpected Encounter in the Library

Im a straight 38 year old man who who is new to all this but im turned on by a Tranny, but this one time a college male feminine student responded to my add. After a few emails back and forth we

Posted by a straight man

By Deleted User

0

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A New Experience at the Hotel

First of all I been on this site for awhile with a handful of encounters. Nothing major. But just having moved to a city due a job change it has been a dry spell. I answered an ad lookingfor a cd

Posted by a TS / CD

By Deleted User

0

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A Memorable First Meeting in Public

I love being with Cds and trans, I find them to be extremely erotic! I had been emailing and chatting on Kik with one for awhile before we decided to meet. (We were in no rush.) We met in public

Posted by a straight man

By Deleted User

0

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A Memorable Motel Room Encounter in Livermore

Back when CL encounters were still up and going i posted an Add(M4T) about having a motel room to myself out Livermore due to work.. The add headline read "Handsome Easy Going Guy looking to

Posted by a straight man

By browndoesitbest69

0

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An Unexpected Visit from a Charming Gentleman

I am a 49 yo CD gurl I have met many a dominant top man on here but a few have risen above and beyond well one night a gentleman came over and as I was dressed in thigh high purple fishnet stockings

Posted by a TS / CD

0

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Exploring Femininity and New Experiences

Nothing is hotter than getting fucked cowgirl style while you're doing your favorite drug at the time. I learned a long time ago if i were going to do a load then I wanted to be in as much

Posted by a TS / CD

1

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An Unexpected Encounter at the Gym

THE BIRTH OF THERAN JAMES PART 2 So, he throws this leotard at me. I dont know if it was a lucky guess on his part or his sister had told him this information too. It was

Posted by a TS / CD

By Anonymous

2

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An Unexpected Encounter with Older Men

I am a non passable crossdresser. I love wearing mini skirts, a blouse, stockings, cfm heels, and a lil lipstick. I do not wear a wig. I am all bottom, and love pleasing top men with my mouth, hands,

Posted by a TS / CD

By Deleted User

0

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A Relaxing Evening of Self-Care and Anticipation

(B) That’s why I’m here. I’m going to train you to be the best little cock-sucking sissy slut you can be. You crave the feeling of a big, hard cock in your mouth, don’t you?

Posted by a TS / CD

By wildermann1950

0

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Exploring Feminine Style and Self-Discovery

(A) I’m going to give you a special set of instructions to make you feel like a soft, sensuous girl. You love feeling like a girl, don’t you? There’s no other feeling like getting

Posted by a TS / CD

By wildermann1950

0

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A Journey of High School Friendship and Discovery

THE BIRTH OF THERAN. This is the true story of how I found out that I am a sissy slut! I have all ways known I had a fetish for girls wearing shiny clothes! I never knew why or even when it

Posted by a TS / CD

1

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An Unexpected Meeting at the Door

I've always been attracted to CDs but have never been with one. I decided to check out the CD section and saw a post about a CD wanting a man to fuck her Rubber tits. I checked it out and

Posted by a straight man

By smithblue485

0

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A Nervous First Visit to His Home

Asian CD here. I have always loved to dress up and pretend I’m a girl. It started off pretty simple - buying women’s clothes and shoes here and there. Eventually, I started to become more

Posted by a TS / CD

By de_kaleidoscope2

5

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A Weekend Getaway with an Older Companion

I always find older men attractive. So posted an ad for 50+ hot daddies. There was this older man whom i started to talk with. Im 22. 5'6. Cd. He was 62. 6'5. With an amazing body. He

Posted by a TS / CD

By Deleted User

1

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A Night of Unexpected Encounters

I was feeling quite naughty one night when my gf was working a nightshift, so I hopped on here and started scrolling through the ads. saw one for a straight man wanting to experiment. he was in his

Posted by a TS / CD

By Anonymous

3

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My First Time Dressed at the Bookstore

A true story of my first time.. The first time i went out dressed. I went to a bookstore in east Portland. As I got out of my car feeling the breeze up under my very short silky skirt, trying to

Posted by a TS / CD

1

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An Unexpected Visit and a Surprising Reveal

I responded to an ad from a married asian woman looking to give oral. We chatted via email for a few hours, then she invited me over. I was rock hard all the way to her house. When I arrived, I

Posted by a straight man

By sirjakeelliott

3

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A Curious First-Time Encounter with a New Friend

My 1st time ever with a TS girl was amazing! I had always been curious and had wanted to experience hooking up with a TS girl. One night i was drunk and a bit high and had the nerve to respond to an

Posted by a straight man

1

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Top Authors

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

RISING AUTHORS ON DOUBLELIST See all

C caniuseu “First time shed intimacy”

John Lee Erwin I am He-Man “Chick with appendage picks me to lick her appendage.” F Freshfresh “Available for connection” A almitaaa “Give it to me buddy”

Rank	Author · Category	Latest Story	Views	Listens	Upvotes	Trend
#1	derake14 Gay Straight for Gay Straight	Parking lot kiss	33.8k	625	4.1k	↗
#2	Tiffanyheels Trans Couple Straight	Crossdressing intimacy in office	76.1k	1.4k	3.2k	↘
#3	KestrelElbow9092 Straight for Gay Gay Straight	Beautiful and Black	23.0k	352	3.1k	↘
#4	cnysub Gay Trans Straight	Ads on DoubleList	45.4k	519	2.9k	↗
#5	kimorafoxxsexycd Gay Couple Trans	Very kinky self care	69.6k	1.0k	2.7k	↗
#6	sissyjamie4daddys Trans Couple Straight	Sucking appendage in the club	43.5k	456	1.9k	↘
#7	wally4u Gay Trans Straight for Gay	From Zorbas To His Hotel Room	50.0k	272	1.8k	↘
#8	Steve Straight for Gay Straight Gay	Gym kiss pt.2	47.4k	593	1.7k	↗
#9	curiousladyd Straight Couple Straight for Gay	First really big appendage	9.8k	356	1.2k	↘
#10	Dedavis Straight for Gay Straight	House hunting pt 1	37.8k	276	1.1k	↗

Page 1 of 50 · Showing 1–10 of 500 authors

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