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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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A Surprising Encounter on the Couch

part 2 end of my virginity I slid my lips down his beautiful cock and began kissing and sucking his balls. He pushed my back against the end of the couch and stood over me dangling his balls in

Posted by a TS / CD

5

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Exploring New Boundaries at the Bar

My wife was a very sexual person and loved to try different things. We had sex in any position we could think of and then she started liking anal play and sex. After a while she started to want to

Posted by a TS / CD

10

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An Unexpected Encounter in a Dark Alley

I LOVE giving road head n car fucking. The adrenaline rush of getting caught by some random stranger as I'm either sucking a daddy mans cock, or getting my lil sissy cunt rammed n crammed full

Posted by a TS / CD

By sissyjamie4daddys

14

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A Journey of Self-Discovery and Connection

I am long time crossdresser and had had girlfriends that loved it. However, that was years ago. Mow it is hard to find a woman that likes it and wants to have sex with me dressed as a woman or go to

Posted by a TS / CD

By Tiffanyheels

4

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A Unique Encounter on a Hiking Trail

I figured if women treated me like shit others must be in the same boat and figured I'd start crossdressing and offer what we were all missing. I stole a dress from an ex (a aline skater dress

Posted by a TS / CD

By CD Danielle Doggie

6

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Unexpected Encounter by the Train Tracks

I love it when I'm out with one of my daddy mens n he decides he wants to fuck me right then n there. Don't care where we are, he just pops up n decides he's gonna fuck me right then.

Posted by a TS / CD

By sissyjamie4daddys

1

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The Challenges of Apartment Hunting

This happened bout 3 years ago. I was out apartment hunting as I really needed n wanted something a lil bigger. Like a 2/3 bedroom with like 2 bathrooms. For some reason, I kept like getting the

Posted by a TS / CD

By sissyjamie4daddys

5

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A Night of Surprises at the Gay Club

I get dress up just til go and fuck as meny guys as I can go to the gay club pick up guys be sucking dick giving head in my van finish him off go back inside pickup another cock til suck last night

Posted by a TS / CD

6

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Exploring a Unique Dress-Up Fantasy Encounter

I got a bug up my ass to try out a fantasy of mine which is dress up in female clothes and suck off a man. Well I posted on here and I found someone after a few hours and after exchanging a couple

Posted by a TS / CD

By curiosity899

8

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An Unexpected Charity Party Experience

The ad was simple n straight to the point. It was from a 63 yr old daddy mans who had friends over n was looking for a trans, fem boy, or a sissy gurl like me. The entertainment he had arranged

Posted by a TS / CD

By sissyjamie4daddys

5

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An Unexpected Reunion at a Drag Show

After coming out at 19teen as a Trans slut I was going to gay night clubs doing drag shows picking guys up just to fuck even had me a sugar daddy for awhile then one Friday night I was do to do a

Posted by a TS / CD

10

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A Journey Through Orlando's Nightlife

I always knew I wanted to be a slut whore suck some dick in my teens including my friends uncle but as soon as I trun 18 2weeks later i,am dressed and on a gray honda head to flo to become the big

Posted by a TS / CD

10

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An Unexpected Encounter in a Private Basement

BBC answered my ad and I agreed to meet at a private location. I was feeling very nasty and a little anxious. This place was in Aurora and the residents he occupied was a basement with private

Posted by a TS / CD

9

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An Unexpected Visit Turns Into a Surprise

I was apartment setting for a new girlfriend who was outa town but had a lizard that needed feed i was there cleaning be noise when I came across the sexyoutfit drew i,v always love crossdresseing

Posted by a TS / CD

8

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An Unexpected Visit During House Sitting

I was apartment setting for a new girlfriend who was outa town but had a lizard that needed feed i was there cleaning be noise when I came across the sexyoutfit drew i,v always love crossdresseing

Posted by a TS / CD

2

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A Playful Afternoon with New Lingerie

Yesterday the courier delivered my new black bra and panties. The bra was one of those bras that are half bras, they hold up your tits but let your nipples hang out, (very Sexy). The

Posted by a TS / CD

7

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Cuddling After a Fun Night Together

I knew it wouldn't last long, but I didn't care. I was riding a daddys cock as his lil twinky sucked his balls n licked my ass as it wiggled n twerked on his daddys cock. I leaned back, my

Posted by a TS / CD

By sissyjamie4daddys

3

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Exploring Identity and Connection at the Bar

I have been crossdressing since I was about 13 years old. That was with my older sister’s panties and bras. Then I discovered my mother’s things and put those on. Later when I was

Posted by a TS / CD

By Tiffanyheels

9

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Unexpected Meeting in a Movie Theater Bathroom

I am bi and a crossdresser. I crave cock and cum. Even if I am not dressed like a slut, I will take cock anywhere and time. One day I was at a regular movie theater. Went in the rest room to wash

Posted by a TS / CD

By Tiffanyheels

5

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A Surprising Confession About Panties and Secrets

I started crossdressing young. First my sister’s panties and bras, my mother’s girdle and stockings, then any girl I could get panties from. When I got married, after my wife came in her

Posted by a TS / CD

By Tiffanyheels

6

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Rank	Author · Category	Latest Story	Views	Listens	Upvotes	Trend
#1	derake14 Gay Couple Straight for Gay	He wanted intimacy twice a day	77.0k	1.0k	4.6k	↘
#2	Tiffanyheels Straight Couple Trans	Parlors in Japan	172.3k	2.4k	4.3k	↗
#3	kimorafoxxsexycd Trans Gay Couple	I did some very mischievous things.	156.9k	1.6k	3.9k	↗
#4	cnysub Gay Couple Trans	The observer from DoubleList	104.8k	814	3.7k	↘
#5	KestrelElbow9092 Gay Couple Straight	Her Boyfriend.	77.2k	662	3.6k	↗
#6	butchmax Straight Gay Couple	My Husbands Best Friend	118.7k	805	2.1k	↗
#7	sissyjamie4daddys Trans Couple Straight	I love water	84.3k	496	2.0k	↘
#8	Dedavis Straight for Gay Straight	Super Bowl group event part six	102.1k	704	2.0k	↘
#9	wally4u Gay Couple Trans	Missed The Fine Print! BIG TIME!	73.0k	330	2.0k	↘
#10	Steve Straight for Gay Straight Gay	Doublelist fan	57.6k	677	1.8k	↘

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