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Transgender Sex Stories – Real Encounters & Passionate Experiences

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Category: TS / CD

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An Unexpected Encounter in the Office

I'm a crossdressing lil sissy who wears her clothes under her man clothes n I HATE it! God I would love to be able to wear my fem clothes but the world ain't ready for that. I am very Very

Posted by a TS / CD

By sissyjamie4daddys

11

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A Surprising Morning Encounter with a Familiar Face

Best part of waking up is a soldier in your sissy cunt is exactly how I like to start my mornings. N that's how my morning started. Ok, so daddy is ex military, but once a marine always a

Posted by a TS / CD

By sissyjamie4daddys

4

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A Unique Dynamic in a Relationship

My wife wanted to see me get fucked from behind. First with toys, then her while wearing a strap on, now she wants to see a man cum in my ass while she watches. She even hopes to get to take his

Posted by a TS / CD

By samanthaandi

7

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An Unexpected Night Out with Friends

This is part 2 with a couple.We were in a room that was full of sexy clothes, lingerie, sexy high heels and other stuff.She handed me a red garter belt with red fishnet stockings and red thong and

Posted by a TS / CD

6

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An Evening at the Local Adult Store

One evening I stopped by the local adult book and theater store in my city.The evenings it's always busy with guys in the booth area, theater and in the back parking lot.You can find prostitutes

Posted by a TS / CD

8

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Exploring New Orleans' Unique Bookstore Scene

I like to go to the adult book store arcade with gloryholes. I would find me a booth with a good size gloryhole, in some cases there would be a hole in both walls. I would strip down to just my

Posted by a TS / CD

By Anonymous

5

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An Unexpected Encounter at the Gas Station

Earlier today I walked to my local gas station for some cigs. It's bout a 10 minute walk. It's nice out today. The calm before the big storm. I was wearing a pair of leggings, a blouse, n a

Posted by a TS / CD

By sissyjamie4daddys

13

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An Unexpected Late Night Email Encounter

So after a fuck date with one of my local regular daddy mens last night, I was chillin at my house looking thru my emails n texts. I had an email from an older gentleman who was interested in setting

Posted by a TS / CD

By sissyjamie4daddys

7

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Neighbors Gather for a Cozy Evening

Another cold night here in the Lou, but nice n warm in my garage. A few neighbors stopped by to get their cocks all nice n warm. I have them my mouth n my prissy sissy cunt to use. This time, I bent

Posted by a TS / CD

By sissyjamie4daddys

6

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A Unique Encounter Between Crossdressers

I have been a prissy sissy crossdressing bottom since I was broke in by my daddy 8 years ago. I have sucked n been fucked by 1000s of daddy mens n young studs. I have played with other gurls n a few

Posted by a TS / CD

By sissyjamie4daddys

7

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An Unexpected Visit Turns Into Something More

I was chatting online hard and horny and needing a release. A guy messaged me and offered to take care of me but I was only looking for women. After an hour he messaged back. He was like, look I can

Posted by a TS / CD

18

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A Cozy Gathering in the Heated Garage

Sitting in my heated garage with 3 daddy mens having a great fucking time. I'm sitting on a daddy mans lap, bouncing up n down on his tasty rock hard cock, his balls slapping my sissy ass as

Posted by a TS / CD

By sissyjamie4daddys

5

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Exploring Fantasies and New Connections

Freaky trans woman seeking exciting encounters tonight. Explore your fantasies, and lets make them a reality together. I'm versatile and can both top and bottom. can host or come to you and am

Posted by a TS / CD

11

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A Surprising Encounter at the Bookstore Theater

My whore wife n I stopped at our local adult bookstore this afternoon. We went to the theater n was soon followed by several men. My whore wife sat a few seats away from me. She unzipped her dress in

Posted by a TS / CD

By sissyjamie4daddys

7

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A Journey of Acceptance in a Unique Relationship

I love watching my wife getting gangbanged and gang fucked. So many cocks and so much cum dumped in her cunt ass and throat. And I get the joy of licking and eating all of that cum out of her

Posted by a TS / CD

By sissyjamie4daddys

5

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A Night of Surprises at the Party

This is part 2 at the party.I see the glass filling up but it was going to be a while.Guys switching off when I said let me go change into something sexy.I went to the room and I have some shorts

Posted by a TS / CD

7

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A Surprising Outfit Change at the Ranch Party

The other day I got invited to a party at a ranch where rich people.This ranch was up in a hill and it was the only house around.The gentleman that invited me know a real good friend of mine and he

Posted by a TS / CD

5

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A Journey of Self-Discovery and Transformation

How did I become the prissy sissy slut I am today? That's easy. I was married to a whore. My now ex whore wife groomed me. While we were dating, n after we married, I was her lil cuck slut. She

Posted by a TS / CD

By sissyjamie4daddys

4

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Unexpected Messages from Local Daddies

It's been a few weeks since I stopped in my local sex shop to get something to suck on or ride. When I walked in, the guy behind the counter told me he was gonna put my picture on a milk carton

Posted by a TS / CD

By sissyjamie4daddys

0

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A Chance Meeting at the Bar Leads to Surprises

So last night at the bar I ran into my friends fine ass hell baby daddy I walked up to him said hey kavonte it's Kimora your baby mama trans friend hey jumped up said hey girl what you doing I

Posted by a TS / CD

By kimorafoxxsexycd

2

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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

R roosterrogers “Young eager for hours” J jabby69 “It took 20 years.....” S submit2one “Too Many Tops Think Anal and Intimate Technique is One in the Same” S sissyemilymatt “Night walk”

Rank	Author · Category	Latest Story	Views	Listens	Upvotes	Trend
#1	derake14 Gay Straight for Gay Couple	The fast and furious	59.8k	840	4.4k	↗
#2	Tiffanyheels Couple Straight Trans	Wife turns bi after toy party	132.8k	2.0k	3.9k	↗
#3	kimorafoxxsexycd Gay Trans Couple	Swallowed my bfs meal at lunch	127.6k	1.4k	3.5k	↗
#4	KestrelElbow9092 Straight Gay Couple	Picnic Fun	48.5k	517	3.3k	↗
#5	cnysub Gay Trans Straight	Part 1 Nude Performer	75.1k	694	3.3k	↗
#6	sissyjamie4daddys Trans Couple Straight	I love water	71.4k	487	2.0k	↗
#7	wally4u Couple Trans Gay	Got Wife Off Flying To Cabo!	67.0k	309	1.9k	↗
#8	Steve Straight for Gay Straight Gay	Gym kiss pt.2	53.6k	644	1.7k	↗
#9	butchmax Couple Gay Straight	I Guess We Asked for it	83.3k	616	1.7k	↘
#10	powers8 Gay Straight Straight for Gay	A fantasy come true	82.7k	668	1.7k	↘

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