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Transgender Sex Stories – Real Encounters & Passionate Experiences

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Category: TS / CD

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An Unexpected Reunion After Divorce

When my ex wife n I were married, she was the town whore, the city slut, the metro cum dump. I was her lil cuckold clean up bitch. She fucked whoever, whenever, wherever, however she wanted n ingot

Posted by a TS / CD

By sissyjamie4daddys

8

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A Festive Gathering on Christmas Morning

so Christmas morning was so much fun i had 4 or my older single men over to use me all they want i put on my little miss clause outfit and wrapped myself up in wrapping paper had my little clitty

Posted by a TS / CD

10

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From Online Chats to a Hotel Meeting

I am a Transman that is only post op top surgery. I did have a very short sexual experience shortly after high school. But it didn't workout. Fast forward 13 years or so and I'm still

Posted by a TS / CD

7

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A Special Reunion at the Restaurant

I met up with a very special uncle earlier today. Uncle Robbie texted me telling me he needed to see me. Now, Uncle Robbie lives 25 minutes away n he agreed to drive to my area to meet me at a

Posted by a TS / CD

By sissyjamie4daddys

7

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A Birthday Party Turned Unexpected Adventure

My bday part 2 I was loving it as she fucked me hard and deep in every position especially with me on top and i wasnt holding back then she rolled me up in a ball and stood over me fucking me as she

Posted by a TS / CD

5

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A Birthday Surprise and Personal Transformation

The best birthday ever My wife and i had been married about 10 years when i started dressing up and it kept getting wilder each time till it got to the point where she was to shy to get any wilder

Posted by a TS / CD

4

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A Unique Encounter with New Friends

DOUBLE STUFFED: I am a sissy slut bottom. I love cock n cum. I prefer daddy mens n uncles that are older than me. I am a trans, with 38DDs tittys, but I still have my lil teeny tiny wand. It is

Posted by a TS / CD

By sissyjamie4daddys

2

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An Unexpected Introduction to New Neighbors

It was such a beautiful day out today here in St Louis MO, that I decided to take my prissy sissy ass out for a lil walky. I put on a pair of tight lil bike shorts, a lil red blouse that showed

Posted by a TS / CD

By sissyjamie4daddys

7

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A Surprising Meeting at the Adult Store

I was just told I was a dirty cock sucking sissy by some guy I sucked off at the porn shop. Like really? Is that a complaint or a compliment? I'm not sure. I know he wasn't complaining when

Posted by a TS / CD

By sissyjamie4daddys

4

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A Weekend Fishing Adventure on a Houseboat

hello everyone im know as the town slut i am a sissy gurl long natural hair some piercings and slutty tattoos im always in little skirts and dresses wearing heels and my makeup done my tiny clitty

Posted by a TS / CD

2

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A Night Out at the Gay Bar with Friends

Last night I was dressed up looking very cute and sexy this guy I've been seeing picked me up and took me to the gay bar right were having drinks dancing intimately kissing he tells me id like

Posted by a TS / CD

By kimorafoxxsexycd

5

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A Festive Surprise for Special Connections

Tis the season of giving n I LOVE giving up my sissy cunt n my mouth to all those deprived daddy mens that ain't getting shit from their wifey-pooh or girlfriend. I'm a guaranteed lay,

Posted by a TS / CD

By sissyjamie4daddys

4

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A Surprise Visit to Daddy's Place

So last night I met up with one of my regular local daddy mens. Daddy mans invited me over to his house as his wifey-pooh was doing some Christmas shopping. Daddy mand figured we had bout 1-1.5 hours

Posted by a TS / CD

By sissyjamie4daddys

3

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An Unexpected Connection at the Gay Bar

So Friday night I had my wig looking cute my nails done My makeup looking on point wearing a cute sexy outfit I decided to go to the gay bar feeling sexy as a woman. I was there maybe an hour and

Posted by a TS / CD

By kimorafoxxsexycd

17

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Navigating Frustrations with Daddy Men

This isn't much of a story as it is a question for other cds/trans woman. I have had LOTS of hookups with daddy mens from this site, AFF, n other sites. EVERY meet n greet, or hookup has led to

Posted by a TS / CD

By sissyjamie4daddys

1

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My Journey with Daddy Eddie: A Unique Bond

I'm a passable lil crossdressing bottom sissy. I was broke in 8 years ago by my daddy Les. Daddy Les turned me onto man love, n turned me out to his friends, n other daddys. There was one

Posted by a TS / CD

By sissyjamie4daddys

6

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An Unexpected Meeting at the Restaurant

"My ain't you a pretty lil sissy" daddy said as I walked past him. "Care to sit on my lap". I was shocked as we were in a restaurant n sitting a few tables apart. I

Posted by a TS / CD

By sissyjamie4daddys

0

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Unexpected Encounters in a Hotel Room

Sitting here in my hotel room, mouth open sucking on daddy mans cock, my legs spread as daddy mans finger fucks my sissy cunt, I cant help but think what a sissy slut I really am. This is my 4th

Posted by a TS / CD

By sissyjamie4daddys

2

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A Night of Luck and Unexpected Connections

Went on a date night last night with one of my out of town daddy mens. We had din din n then to a local casino, as my daddy mans was feeling lucky n in a gambling mood. After din din, we went to

Posted by a TS / CD

By sissyjamie4daddys

2

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An Unexpected Visit Leads to Connection

It was amazing meeting this guy on here, we talked and I agreed I hosted, he came over, di the needful at the entrance for verification. And it was all lit I stepped out to pick him up, we both

Posted by a TS / CD

By Deleted User

0

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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

S savanahcole “Super cute 🥰 and adorable” 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.”

Rank	Author · Category	Latest Story	Views	Listens	Upvotes	Trend
#1	derake14 Gay Straight for Gay Straight	Parking lot kiss	34.2k	628	4.1k	↘
#2	Tiffanyheels Trans Couple Straight	Crossdressing intimacy in office	76.8k	1.4k	3.2k	↘
#3	KestrelElbow9092 Straight for Gay Gay Straight	Beautiful and Black	23.3k	353	3.1k	↘
#4	cnysub Gay Trans Straight	Ads on DoubleList	46.7k	523	2.9k	↘
#5	kimorafoxxsexycd Gay Couple Trans	Very kinky self care	72.6k	1.0k	2.7k	↗
#6	sissyjamie4daddys Trans Couple Straight	Sucking appendage in the club	44.2k	456	1.9k	↘
#7	wally4u Gay Trans Straight for Gay	My Birthday Suprise!	50.6k	272	1.8k	↘
#8	Steve Straight for Gay Straight Gay	Gym kiss pt.2	48.6k	605	1.7k	↘
#9	curiousladyd Straight Couple Straight for Gay	First really big appendage	10.0k	357	1.2k	↘
#10	powers8 Straight Gay Straight for Gay	An absolutely amazing 3 friends	32.4k	318	1.1k	↘

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

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