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Transgender Sex Stories – Real Encounters & Passionate Experiences

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An Unexpected Encounter at the Frat Party
Went to a party last night at a frat house. Now I love me some young stud cock just as much as the next gurl, but I still prefer getting hammered by my older daddys. Young studs love to fuck, love to

Posted by a TS / CD

By sissyjamie4daddys

A Couple's Playful Encounter at the Local Shop
Daddy texted me earlier in the day. He told me to meet him at the local porn shop, that he wanted to watch me work my magic mouth skillz. I got all dressed up, complete with makeup a red wig, n

Posted by a TS / CD

By sissyjamie4daddys

Adventures in a Hotel Room: Unexpected Encounters
I was out of town visiting fam n staying at a hotel. I hopped on here to find some local cuisine, local cocks that needed to dump a nice load of cum. I got several replies to my ad, n chose 4 top men

Posted by a TS / CD

By sissyjamie4daddys

A Night of Unexpected Help in the Country
I was suppose to meet a guy out in the middle of no where Tx for my first bi exp and I was really uncomfortable driving all dressed up but I did only to be stood up and was on my way home when my car

Posted by a TS / CD

By Deleted User

Adventures in Parks and Parking Lots
Parks n parking lots can be a lot of fun to meet up with men. I like going to a park n climbing into a real mans car, van or truck n suck his dick while we drive around with me sucking that delish

Posted by a TS / CD

By sissyjamie4daddys

A Night Out at the Crowded Bar
I am a passable crossdresser who loves my life as a prissy sissy. I identify as a fem. I am 100% bottom, strictly dickly. I am always bending over for tops, or on my knees sucking cocks. I wear fem

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Encounter at the Truck Stop
I am a crossdresser and I meet this really nice trucker online we got to talking and we both decided to meet up with each other on night at a truckstop. On the night we meet I was dressed a little

Posted by a TS / CD

By Deleted User

A Chance Meeting at a Bay Area Hotel
I am a mature CD and love dressing up sometime I go out and have a few drinks so I guess I am some what passable or no just don't say anytime but I get so turned on dressing up once I was in the

Posted by a TS / CD

By Deleted User

Exploring Connections During a Nashville Getaway
A few months back I took a lil vacay to Nashville TN for 10 days. I posted on DL n AFF that I would be in town, n was def looking for some Tennessee studs to get with while I was in town. Now, I was

Posted by a TS / CD

By sissyjamie4daddys

An Evening of Fun and Games with Friends
A local regular daddy called me a few nights ago n invited me over to his place for game night. He told me that there would be a few of his friends just hanging around, drinking, smoking, n paying

Posted by a TS / CD

By sissyjamie4daddys

Unexpected Meeting in a Dallas Hotel Room
Dressing feminine is wonderful and excites me to no end. I simply love wearing panties, bra, thigh hi hose, short dresses or skirts/blouse to show off my legs and ass and ad a blond wig and heels

Posted by a TS / CD

By charleyandsnickers

Cozy Days with Friends and Good Company
What a beautiful last few days of weather we have had. It's rained the last 4 days here, perfect weather to stay in bed n curl up with a good book, or snuggle up with a few good men. I chose the

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Visitor on Moving Night
I’m ftm and love being dominated and used. A few years ago, I was moving into a new place with friends. The first night I was alone. No one else had moved in yet. Laying in my half unpacked

Posted by a TS / CD

By fuckboy1312

A Weekend of Pampering and New Connections
I took a lil vacay with 1 of my sugar daddys last week to a nice resort in Florida. Daddy pampered my lil prissy sissy ass. I got treated like a princess. Massages, spas, spending money on new

Posted by a TS / CD

By sissyjamie4daddys

A Summer Lunch and Poolside Gathering
I had just graduated from college and was waiting at home for orders to report for basic military training, about age 21 at the time. During that down time, I agreed to house- and dog-sit for nearby

Posted by a TS / CD

By Vsecrets

A Surprising Hotel Encounter Leads to Confidence
I'm a latina sissy 5"7 140lbs with a small waist and big ass, I've always been smooth & minimal hair on my body and I use to love sucking cum out of my girlfriend's pussy, but

Posted by a TS / CD

By portlandpartier

An Unexpected Meeting in the Bathroom
I'm a crossdresser 46 but not passable. I wish I could so I could dress in public, so I wear thigh high stockings, garter belt, panties and bra under my male cloths. I'm in MegloMart

Posted by a TS / CD

By cnysub

Old Friends Reconnect on a Cold February Night
My first BBC........ Finally got the chance to tell my story iit was a cold night in February and i got a message one night from an old friend that i hadnt heard from in years we used to hang out

Posted by a TS / CD

By sissiesdream

Unexpected Visits and a Pink Skirt Adventure
I have been a busy busy lil prissy sissy since Friday night. Here it is Sunday late afternoon, n I still have a daddy or 2 coming over later for some sucky fucky time. Friday I had me some good old

Posted by a TS / CD

By sissyjamie4daddys

A Surprising Night with Daddy
Part 2 Daddy was passed out in my bed. I saw his cock was standing straight up in his pants. What a shame! I am buzzed real good n hornier than a mother fucker. It took every ounce of my being not to

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 35.4k 634 4.1k
#2
Tiffanyheels
Trans Couple Straight
Crossdressing intimacy in office 78.3k 1.4k 3.2k
#3
KestrelElbow9092
Straight for Gay Gay Straight
Beautiful and Black 24.3k 355 3.1k
#4
cnysub
Gay Trans Straight
Ads on DoubleList 48.2k 531 2.9k
#5
kimorafoxxsexycd
Gay Couple Trans
Very kinky self care 75.1k 1.1k 2.8k
#6
sissyjamie4daddys
Trans Couple Straight
I love water 46.4k 461 1.9k
#7
wally4u
Trans Gay Straight for Gay
Pre-Halloween CD Dress Up! Part 1 53.1k 276 1.8k
#8
Steve
Straight for Gay Straight Gay
Gym kiss pt.2 49.3k 613 1.7k
#9
curiousladyd
Straight Couple Straight for Gay
First really big appendage 10.3k 360 1.2k
#10
powers8
Straight Gay Straight for Gay
Back with Michelle and Lisa 34.7k 353 1.1k
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