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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 on the Front Porch
I have a sugar daddy that lives in the country. The closest house to his is like a few miles away. Daddy loves to fuck me while we sit on the front porch. The other day we were on his front porch as

Posted by a TS / CD

By sissyjamie4daddys

A Surprise Visit from an Old Friend
I hadn't seen my fwb for a while but last weekend all the stars aligned and he was coming over. I spent a couple hours getting ready. I had a small black dress on with sexy stockings , heels,

Posted by a TS / CD

By hardbitheway

A Memorable Night in Victorville
Victorville TS (Coco) It was a nice warm night in Victorville about a year ago. I met this guy on doublelist, very cute. Light skinned black guy, tall, slim build, dressed nice and smelled good as

Posted by a TS / CD

By caliboy

A Memorable Night in Victorville
Victorville TS (Coco) It was a nice warm night in Victorville about a year ago. I met this guy on doublelist, very cute. Light skinned black guy, tall, slim build, dressed nice and smelled good as

Posted by a TS / CD

By caliboy

Exploring Unexpected Connections at Home
I'm a total bottom sissy who simply LOVES pleasing top daddys. I fully dress in fem clothes, and identify as a fem. I have several regular top daddys that I hook up with to suck and fuck. Most

Posted by a TS / CD

By sissyjamie4daddys

A Thrilling Encounter on the Bike Trail
I have a newer fetish. I love sucking cock n getting my lil sissified ass fucked in public areas, such as parks, restrooms, parking lots. Any place where I could get caught with my ass in the air.

Posted by a TS / CD

By sissyjamie4daddys

A Surprising Encounter at the Bookstore
I simply LOVE sucking cock, draining those beautiful fab cum filled balls, swallowing every drop of cum. Nothing in this world is better than getting that yummy cum in my tum tum. Creamy goodness I

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Meeting at the Gay Bar
I love crossdressing and being a submissive feminine slut. I am 26 y/o, 5’6”, 150 lbs, blue eyes and married. My wife and mother-in-law own and operate a business which requires them to

Posted by a TS / CD

By olderbisubcd

An Unexpected Hotel Visit with a Daddy
I responded to an ad from a top daddy that was in town who was looking for a sissy to use. After a few emails he invited me to his hotel. When I got there he met me at his door with just a towel on.

Posted by a TS / CD

By sissyjamie4daddys

Unexpected Connections at the Bookstore
Hello I have been a Crossdresser for many years now and can get ready in a whip. but lately I find myself visiting the local book stores I love it when a guys in the booth and he has it out stroking

Posted by a TS / CD

By Deleted User

A Night of Unexpected Encounters at a Rest Stop
I was working in a small city. I was looking for a porn shop that evening. I didn't find a store in that city. I was just sitting in my motel room. I started getting dressed up. I put on my

Posted by a TS / CD

By Miniho

A Chance Meeting at a Country Diner
Last week I stopped at a lil diner in the middle of nowhere to get a bite to eat. Now, I am a full time crossdresser who goes out in public wearing fem clothes. I identify as a woman, wig, makeup,

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Encounter in the Park
I responded to an ad from a guy that wanted someone to watch him jack off in a public place. I agreed to meet him in a park. He told me where he would be, the car he was driving, everything. I pulled

Posted by a TS / CD

By sissyjamie4daddys

An Unforgettable Night at the Hotel Party
I had the honor of being the center of attention, the entertainment for a group of men at a blow bang party last night. I was invited to a hotel where I was placed in the center of the room,

Posted by a TS / CD

By sissyjamie4daddys

Unexpected Connections at the Nightclub
Last night I stopped at a club to get my suck n fuck on. The club was filled with twinks, daddys n gurls like me. I grabbed a table n ordered a drinky pooh. A few minutes later a few daddys were

Posted by a TS / CD

By sissyjamie4daddys

Discovering New Desires Through Friendship
So I used to be married to a woman, back when I thought I was straight. She had a gay cousin, Jim. Jim used to stop by and hang with us. One night we were partying and my then wife went to sleep.

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Invitation to a Unique Gathering
I got invited to a bukkake party yesterday. When I arrived to the place, there were 5 top men in the living room. On the floor was a mattress where I was to kneel n take care of all 5. I started

Posted by a TS / CD

By sissyjamie4daddys

A Journey of Self-Discovery and Empowerment
After my girlfriend left me for being gay i started packing her things then i grab some of her panties and i got super turned on i ripped my clothes off and put them on i felt really sexy i found a

Posted by a TS / CD

By daviddickson

A Mysterious Meeting in a Hotel Room
I love dressing up in lingerie. Nothing gets me harder than wearing black lacy bra, panties, stockings, and top. I used to occasionally post ads to meet giys while on the road. One such i had just

Posted by a TS / CD

By Builderguy

An Unexpected Evening at Poker Night
I got a text from 1 of my local sugar daddys. Daddy told me he was having a poker night with some buddies, n needed me to be there as the entertainment. Daddy told me to dress accordingly, as in

Posted by a TS / CD

By sissyjamie4daddys

Top Authors

Discover the most engaging creators on Doublelist — ranked by views, listens, and upvotes, with fresh voices breaking in every week.

Rank Author · Category Latest Story Views Listens Upvotes Trend
#1
derake14
Couple Gay Straight for Gay
Making love my neighbor in our pool late at night 67.2k 894 4.5k ↘
#2
Tiffanyheels
Couple Straight Gay
Wife wears revealing dress to party 157.3k 2.2k 4.2k ↘
#3
kimorafoxxsexycd
Gay Trans Couple
Road ride to bf 138.7k 1.5k 3.6k ↘
#4
cnysub
Trans Couple Straight
mY new submissive transgender 85.1k 726 3.4k ↘
#5
KestrelElbow9092
Gay Straight Couple
Another day on the hunt. 56.3k 555 3.4k ↗
#6
sissyjamie4daddys
Trans Couple Straight
I love water 77.1k 491 2.0k ↘
#7
wally4u
Gay Couple Trans
I Guess He Did Have To Go! 70.3k 317 2.0k ↘
#8
butchmax
Couple Straight Straight for Gay
Oh She Knows Dimension Matters Now 98.0k 657 1.9k ↘
#9
Dedavis
Straight for Gay Straight
Adult video store part three 84.3k 603 1.7k ↗
#10
Steve
Straight for Gay Straight Gay
Gym kiss pt.2 54.6k 652 1.7k ↘
Page 1 of 50 · Showing 1–10 of 500 authors

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