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Transgender Sex Stories – Real Encounters & Passionate Experiences

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Category: TS / CD

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I’m a Crossdresser that was on the prowl

That night changed something in me. I flew from LAX to Spokane, carrying a secret I’d never fully lived out in public before. Even going through airport security, I felt a rush—like I

Posted by a TS / CD

13

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The desire of joy vs the normal urge of denialenial

I'm not sure where to start I always been odd. I'd say I marched to different beet but I tried I tried to deny. The first thing I remember was playing sports when j wAs younger in a swim

Posted by a TS / CD

By fionacdsissy

1

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What do ido

You caught me dressed up Why did you walk in me being so valuable Whould she know how I fit in her nylons Oh how you like me too I enjoy them HiFi closths I bend over and wish I you dint Se the

Posted by a TS / CD

2

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I always like me in nylons

My first time with a man He was my boss Whee where in his office He showed me his All I could was stare at his Hard cock What should I do I was so hard Looking and wanting He asked me if I

Posted by a TS / CD

7

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My first time kissing dressed up female

I was on grindr one night and couldn't take it anymore. I wasn't Todd. I was Natalie and I needed to fucking accept it. So I met a guy. Dressed in a pretty blonde wig, panties, pink dress

Posted by a TS / CD

9

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Gay spa visit

I am a long time crossdresser. Shaven smooth and silicone breast forms. I am bi and love to suck cock and be sucked. And I like to be fucked. One night I went to gay bathhouse dressed as a

Posted by a TS / CD

By Tiffanyheels

18

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My first Sissy Orgasm

I have been off and on crossdresser for many years. As I have gotten older I have found it harder to hookup with young hung studs. I was drunk one night and ordered a fuck machine from the web, When

Posted by a TS / CD

By NumbatCloak8150

17

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Part 2 Orphaned at 11.

I had become Gene's boy and I loved it. I couldn't get enough of him. We began kissing with our mouths open and tongues moving around. I was attracted to his hanging balls and started

Posted by a TS / CD

24

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Naturists Adventure

Mia and I lived for more than 5 Years on the Spanish Island Mallorca. The Winter is very quiet, there is not much tourism and all people are slowing down, relaxing after a hard 8 month Sesion with

Posted by a TS / CD

7

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How I started crossdressing

This is a true story. I’m a 59 year old male. The story I’m about to tell happen when I was in High School years ago. Me and my three friends was planning to build a fort out in the

Posted by a TS / CD

By Alessiawrigh

13

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Telling Girlfriend I am a crossdresser

I had been cross dressing for many years. Then when I was married I would put on my wife’s panties and we had sex with me wearing them normally after she came a few times on the panties. At

Posted by a TS / CD

By Tiffanyheels

7

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I wanted a lot and I got it

So I love my mouth completely flooded with cum, this guy was on doubleĺist and posted he had a 3 week load so of course I immediately messaged him and asked him to edge until I got there to build up

Posted by a TS / CD

5

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I wanted a lot and I got it

So I love my mouth completely flooded with cum, this guy was on doubleĺist and posted he had a 3 week load so of course I immediately messaged him and asked him to edge until I got there to build up

Posted by a TS / CD

2

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Dressed For Fun In San Diego!

I hadn't dressed in years when suddenly I Craved IT! I reserved a hotel in San Diego near The Hillcrest District & did most of my shopping on-line. My blonde hair was 18"s long so I

Posted by a TS / CD

10

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Had a Group Encounter

Many years ago a friend, well playmate asked if I was interested in a gangbang, with like 4 guys and myself. We posted ads and had some good responses. Took a bit to set up with my preferences. I

Posted by a TS / CD

By eagerbottomforhungtop

18

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Almost turned into a girl..

I really want to come over to your place and let loose. I want to get dressed and ready in your bathroom while you’re waiting on your bed.. I want to feel like I’m really a sexy girl for

Posted by a TS / CD

By curiosity899

7

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A Trip to the Adult Theater

I'm an older transsexual male to female, living as a female for almost 20 years. it's a hot summer day and I decide to go to the air conditioned theater and enjoy a movie and hopefully

Posted by a TS / CD

18

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Female Bartender Had A Rooster!

I checked into A Hyatt late one Sat night then hit their lobbies bar. The female Bartender, Sue, told me they were closed but made me a drink. She asked & I told her my travel day Had been a

Posted by a TS / CD

42

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My unique storys with an older man P1.

*THIS IS A TRUE STORY, AND I MET HIM HERE ON DOUBLELIST YEARS AGO* Flashback to when I was 21. My late father passed, I was depressed, sexually confused, and seeking a father figure. I've

Posted by a TS / CD

By Deleted User

25

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My Master uses his submissive

I am a submissive crossdresser, I started dressing because I was always, small and gay with almost no hair, short and thin. We emailed back and forth and he told me what he enjoyed having a sub do

Posted by a TS / CD

20

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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

D Deleted User “It’s late but I’m down to chill and have a little fun!!” 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”

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	76.2k	1.4k	3.2k	↘
#3	KestrelElbow9092 Straight for Gay Gay Straight	Beautiful and Black	23.1k	352	3.1k	↘
#4	cnysub Gay Trans Straight	Ads on DoubleList	45.5k	520	2.9k	↗
#5	kimorafoxxsexycd Gay Couple Trans	Very kinky self care	69.8k	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	47.5k	594	1.7k	↗
#9	curiousladyd Straight Couple Straight for Gay	First really big appendage	9.9k	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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