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Transgender Sex Stories – Real Encounters & Passionate Experiences

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Navigating Secrets in a Married Life
Ive been married for 15 yrs and my wife has no idea I love to dress up in sexy panties and lingerie and fantasize about all kinds of dirty things..!! I started when I was teen I would go into my

Posted by a TS / CD

By bisexpantyboy

A Chance Encounter at the Grocery Store
Daddy mans cock was just what the doctor ordered. Beautiful, tasty, delish 8" piece of meat hanging tween daddy mans legs n my lips soon to be wrapped around it n feeling it grow in my mouth. I

Posted by a TS / CD

By sissyjamie4daddys

A Playful Role-Playing Adventure at Home
I have a daddy that I have been dating for the past few months. When I say dating, he comes over to my house for sucky fucky time, or I go to his place for sucky fucky time. Anywho daddy text me to

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Encounter with a Neighbor
I got all dolled up i looked totally passable and took a few pics and posted them looking for large cock i got up and made myself a coffee and came back thinking i would be sitting on my dildo but i

Posted by a TS / CD

By daviddickson

A Unique Shopping Experience at a Motel
I have been dressing for about 4 yrs. I am semi passable, 52 and have always wanted to go out in public. I decided to get a motel room in a nearby city 60 miles away where its's a good chance no

Posted by a TS / CD

By cnysub

An Evening at Daddy's Group Social Gathering
I got invited to a lil group social yesterday. It was held at a daddy mans house who fucks me on occasions. Daddy mans told me there would be a few other daddy mens at the group social. Daddy mans

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Visitor and a Surprising Encounter
I replied to an ad posted by a straight top daddy mans earlier today. Daddy mans was looking for a female to get with. I always tell daddy mens, especially the so called "straight" daddy

Posted by a TS / CD

By sissyjamie4daddys

Exploring the Dynamics of Sugar Daddy Relationships
I love a good throat fucking. A daddy mans who knows what he wants n takes it. I love massaging daddy mens cocks with my mouth n throat. Daddy mens sliding their cocks tween my tits, feeding me their

Posted by a TS / CD

By sissyjamie4daddys

A Surprising Reunion at a Kentucky Party
OMG! I have turned another into a sissy! So a few years ago, I met this young stud at a party in Louisville KY. One of my sugar daddy mens was having an end of the year bang n got to have the balls

Posted by a TS / CD

By sissyjamie4daddys

Exploring Weekend Adventures with New Friends
I am NOT a 1 man woman. I prefer quantity over quality. The more the merrier. I don't have a flavor of the month. Mine is more like flavor of the hour, or day. Yes, I have a very hi body count, n it

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Visit to an Older Gentleman
A few weeks ago I met an older daddy mans. Daddy mans is in his early 80s, n not in great shape or health. But he can still get n maintain a nice erection. I went to daddy mans apartment. When I got

Posted by a TS / CD

By sissyjamie4daddys

How a Cleaning Job Turned into a Business
Part 2 cleaning daddy's place Daddy handed me $100 n told me his place looked great. I wasn't sure what the $100 was for. Daddy told me I did such a great job cleaning n organizing his

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Visit Leads to Surprises
Just like the gurl scouts of america motto, I am always prepared. I am always dressed in my fem clothes. Either a pair of tight booty shorts n a blouse that shows off plenty of cleavage, a lil mini

Posted by a TS / CD

By sissyjamie4daddys

Exploring Kinks Through Playful Wrestling
I am a very passionate gurl. I love kissing, snuggles n cuddles, bod contact, exploring daddy mens bod with my lips, mouth n tongue. I love to be passion fucked. Kissing while getting my asscunt

Posted by a TS / CD

By sissyjamie4daddys

Adventures on a Road Trip Through Kentucky
A few years ago I was driving my lil prissy sissy ass from Lexington Kentucky to St Louis MO. I had posted a few ads on DL in towns I was driving thru in hopes of meeting up with a daddy or 2 or more

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Visit from a Close Friend
I was all snuggled up in bed last night when I got a text from one of my daddy mens. Seems daddy mans was in the area n wanted to stop by for some fun. I texted daddy mans back n told him to come in

Posted by a TS / CD

By sissyjamie4daddys

A Thrilling Secret Encounter in the Park
I had been dressing secretly for some time, going out in the evenings to quiet parks and areas where I might be discovered feeling the thrill but very unlikely to. I started reading craigslist posts

Posted by a TS / CD

By yorkscd

A Chance Encounter at the Bookstore
I have had my share of all types of daddy mens: black, white, older, younger, married, single, straight, bi, gay, thugs, bikers, nerds, n good ol country boys. Last night was a 1st for me. So last

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Hotel Encounter with Daddy
I was invited to a hotel room by an older daddy who needed his love muscle rubbed. Daddy told me he was sore n needed a real good rub down. He asked me to dress slutty. Is there any other way to

Posted by a TS / CD

By sissyjamie4daddys

A Cozy Winter Snuggle Date with Daddy
I saw n replied to an ad from an older daddy mans who was looking for a snuggle bunny to keep each other warm on cold days. The daddy mans also said some extra curricular activity would be expected.

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
Gay Straight for Gay Straight
Parking lot kiss 35.0k 633 4.1k
#2
Tiffanyheels
Trans Couple Straight
Crossdressing intimacy in office 77.9k 1.4k 3.2k
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KestrelElbow9092
Straight for Gay Gay Straight
Beautiful and Black 23.9k 355 3.1k
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cnysub
Gay Trans Straight
Ads on DoubleList 47.7k 529 2.9k
#5
kimorafoxxsexycd
Gay Couple Trans
Very kinky self care 74.3k 1.1k 2.7k
#6
sissyjamie4daddys
Trans Couple Straight
I love water 45.5k 461 1.9k
#7
wally4u
Trans Gay Straight for Gay
Pre-Halloween CD Dress Up! Part 1 52.4k 275 1.8k
#8
Steve
Straight for Gay Straight Gay
Gym kiss pt.2 49.1k 612 1.7k
#9
curiousladyd
Straight Couple Straight for Gay
First really big appendage 10.2k 359 1.2k
#10
powers8
Straight Gay Straight for Gay
Back with Michelle and Lisa 34.3k 348 1.1k
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