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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 Confessions in the Garage

Such a gorgeous day out today. I decided to clean n organize my garage. I live out in the country area n there are like 7 houses along my street. My house is known as the whore house where the slut

Posted by a TS / CD

By sissyjamie4daddys

24

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A Surprising Meeting in a Hotel Room

I met a young stud at his hotel room earlier today. All he wanted was a handy. He was a lil chunky, bout 225-250, but with a very nice cut n smooth cock. We kissed n made out, which I love doing. I

Posted by a TS / CD

By sissyjamie4daddys

14

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Unexpected Connections at a Family Reunion

When I came out, I blew the fucking closet door off. Hell, I leveled the house AND the entire neighborhood. My fam is NOT very supportive of my life choices or decisions. Well, except for my old

Posted by a TS / CD

By sissyjamie4daddys

10

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A Night Out: Getting Ready for Fun

So yesterday my gf is like me and the girls are going to the casino and the club which pisses me off a lil bit. So when I saw her and her friends leave I get a text from this man I've been

Posted by a TS / CD

By kimorafoxxsexycd

10

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An Unexpected Visit from Daddy Friends

Hooking up with 2 of my daddy mens last night n I got double stuffed. So I'm sitting at home when both of them stopped by within 5 minutes of each other. I had just started sucking the 1st

Posted by a TS / CD

By sissyjamie4daddys

5

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An Unexpected Reunion at the Store

I ended up riding my ex brother in laws cock a few days ago. N it felt so good!! I ran into him at the store. He did not recognize me, but I knew him immediately. When I told him who I was he freaked

Posted by a TS / CD

By sissyjamie4daddys

9

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Unexpected Meeting at the Mall

I'm a bi- trans 24 yrs. old living as a woman but decided to keep my penis. I'm shopping at the mall and notice an older couple maybe in their late 50's but still pretty good looking

Posted by a TS / CD

41

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A Surprise Visit in Saint Louis

I'm a bisexual cross dresser. Why isn't that one of the choices to pick. I'm john 64 bi. Been cross dressing since 71. Enjoyed many 3 ways.mmw, I call them marital three ways. Here

Posted by a TS / CD

19

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A Surprising Discovery in a Three-Way Encounter

So this is how I found out im a sissy .... I was in a three way with my buddy and his Ole lady and he came twice in her pussy and took a break she rolled over on to my face and I instantly had a

Posted by a TS / CD

By Deleted User

13

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A Journey of Self-Discovery and Connection

I never thought I would turn out to be the cock craving, cum loving sissy slut I am. When I was younger, it was all bout getting pussy. But that all changed 10 years ago when I met him. Him being my

Posted by a TS / CD

By sissyjamie4daddys

10

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A Weekend Escape with Friends and Fun

Bout 2 years ago I moved in with one of my daddy mens. Daddy mans knew I had several daddy mens that I would suck n spread my sissy ass cheeks for. He told me I had to stop because we were a couple

Posted by a TS / CD

By sissyjamie4daddys

3

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The Chemistry That Built Between Us

After weeks of teasing messages and late night conversations the tension between us finally became impossible to ignore; when we met, every glance lingered, every touch felt deliberate and what

Posted by a TS / CD

5

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Exploring New Experiences in Houston

I am no was a straight closet cd who was curious about trying my first bi exp and was looking tbry Houston doublelist guys for guys and i ran across a ad that simply said want it ? And a pic of a big

Posted by a TS / CD

16

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Exploring a Unique Power Exchange in Tucson

My dominant top daddy wants to have me GB'ed and I love that thought. He demands I for a GB weekend perversion group with other Dom tops. He explained that he is being selfish not sharing his

Posted by a TS / CD

By sissyslutjessie

4

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A Journey of Self-Discovery Through Online Content

It started like any other pathetic day—jerking off to trans porn, desperate for release, pretending I still had control. That’s when I stumbled across something called sissymaker1. Just a

Posted by a TS / CD

By sissy jessica

11

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A Summer Night Walk on the Bike Trails

I’ve been hooking up with a neighbor for a while now. I’ve never gone out dressed up. One night i dress up and walk over to his house. He says come on. Grabs me by the hand and we go to

Posted by a TS / CD

By Deleted User

15

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An Unexpected Encounter with the Neighbor

I’ve always crossdressed, always been discrete. I’d get dressed in my bedroom and just feel so sexy. I’d feel so tempted to go out and walk in my heels. Feel that breeze on my

Posted by a TS / CD

By Deleted User

9

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A Young Man's Unexpected Encounter with a Couple

I'm a 21 yr. old gay male , very gay and love to suck cock and get fucked, I have always wanted to be a crossdresser or maybe even trans. I posted here for someone to help out with the cost of

Posted by a TS / CD

9

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A Mysterious Morning Surprise with Breakfast

I woke up this morn to breakfast in bed. That's right. I got me 2 sausage links fed to my lil sissy ass, n I got to enjoy some of that sweet cream of daddy mans in my coffee. I was asleep this

Posted by a TS / CD

By sissyjamie4daddys

2

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A Night of Unexpected Connections in the City

I’m a tall, slender cross-dresser — 6’4”, 175 lbs, long blonde hair, tattoos running down my arms and back. When I’m fully dressed I look like a total slut: tight

Posted by a TS / CD

9

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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	Girlfriend turned bi and craves females	132.6k	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	48.4k	517	3.3k	↗
#5	cnysub Gay Trans Straight	Part 1 Nude Performer	75.0k	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	83.1k	616	1.7k	↘
#10	powers8 Gay Straight Straight for Gay	A fantasy come true	82.7k	668	1.7k	↘

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

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