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Transgender Sex Stories – Real Encounters & Passionate Experiences

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A Week of Secret Visits and New Beginnings
I have been staying with one of my daddy mens 2-4 times a week. Daddy mans wifey-pooh lives n works out of town, bout 225 miles away. So I am with my daddy mans Sunday evening til Friday morn when

Posted by a TS / CD

By sissyjamie4daddys

A Busy Day with Daddy Dates and Connections
Dayumm, I have been a very bizzy lil prissy sissy slut today. I have had 13 phone calls from daddy mens that want or need to see my sissy ass! Some are local n some are out of town daddy mens that

Posted by a TS / CD

By sissyjamie4daddys

Exploring New Dynamics with Friends
Angie told me to suck his balls n lick her lovers cock as she rode him. My wife told me to keep backing my lil sissy ass on my daddy's cock, as daddy slammed me. Angie sucked on my whore

Posted by a TS / CD

By sissyjamie4daddys

Cozy Winter Bonding in St. Louis
It's snuggle n cuddle weather here in St Louis MO. You know the type of weather where you stay inside in bed with a daddy or 2, nakey, full bod contact keeping each other warm. Lay in tween 2

Posted by a TS / CD

By sissyjamie4daddys

Exploring New Dynamics in a Swinging Relationship
I am a crossdresser and my girlfriend loves it! We are both bi and swingers. She loves to have people watch while she is having sex. She craves pussy and licks pussy for a long time before stopping

Posted by a TS / CD

By Tiffanyheels

An Unexpected Visit to Daddy Billy's House
His ad was straight to the point. "MWM not getting any at home. I will host." I replied that I could def help him if he was interested in a crossdressing bottom prissy sissy. He told me he

Posted by a TS / CD

By sissyjamie4daddys

Unexpected Meetings in a Heated Garage
Every night, from 6 at night til 1-2 in the morning. I entertain men in my heated garage. Married men, single, divorced, older or younger, makes no difference to me. My garage is heated, n I have

Posted by a TS / CD

By sissyjamie4daddys

Exploring New Adventures in an Adult Theater
josie here and i tried something new always wondered about going to a adult theater dressed and lubed so last weekend i wore a very nice dress short but not slut type just pretty and very nice. i

Posted by a TS / CD

By greatime00

A Friendly Competition Among Friends
Me n my lil twinky friend decided to have a lil contest on who could suck the most cock. We posted on DL n on AFF n invited as many daddys over as we could. The rules were simple: whoever sucked n

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Dinner with Cowboys in Houston
There's an old saying that everything is bigger in Texas. I'm here to tell you that that saying IS TRUE!! One of my daddy mens had some bizness meetings in Houston TX area last week, n he

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Adventure During a Drive
Queen of road head is a nickname I picked up from my daddy mens. I simply LOVE sucking cock while daddy mens drive down the street or highway. It is a major adrenaline rush for me!! I can't

Posted by a TS / CD

By sissyjamie4daddys

Unexpected Encounters at the Gay Bar
I was dressed up looking sexy as fuck and I met my homegirl and her baby daddy and the gay bar right well I ordered a drink and my homegirl walks up kisses me says hey baby I kiss her back while

Posted by a TS / CD

By kimorafoxxsexycd

Exploring Unique Relationships and Connections
The joy of being daddy mens personal cock sucker is one of the greatest passions in life. My lil prissy sissy mouth LOVES having a cock or 2 cocks in my mouth, sucking, licking, kissing, nibbling, n

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Meeting with My New Boss
I started a new job after new years as a personal assistant for a very wealthy, very successful older bizness man.y first day was running errands for him, picking up his mail, and his clothes. I got

Posted by a TS / CD

By sissyjamie4daddys

Exciting Moments at the Super Bowl Party
i wrote about a very true incident that occured involving me, and around 5 or so guys during a super bowl party that a regular horny friend which I get the awesome pleasure of getting down on my

Posted by a TS / CD

By gary

Exploring Unique Relationship Dynamics Over Eight Years
I'm my girlfriends lil cucky clean up prissy sissy. My place is tween her legs licking up any n all cum messes that her lovers make, either in her pussy or in her ass. I'm also responsible

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Visit from a Young Date
I had a date with this 20 something young stud Saturday evening. Young stud stopped by my house, his cock all a bulging thru his pants by the time he got here. I invited him in, n he gave me a kiss n

Posted by a TS / CD

By sissyjamie4daddys

A Chance Meeting During a Business Trip
I recently stayed at a nice hotel while on business trip in Denver. I enjoy business trips because its the only time I get to dress en femme. I was in my room, sipping some wine and doing my makeup

Posted by a TS / CD

By Guitarpicker.mb61

A Relaxing Night at the Motel Hot Tub
I have dressed as a woman for many years and love it! I am shaven smooth all over and have silicone breast forms as well as nails done, full dress, wigs, sexy clothes, sexy bra and panties, jewelry

Posted by a TS / CD

By Tiffanyheels

A Romantic Evening at Steve's House
I have to admit that driving with high heels on took a bit of getting used to, but it felt so sexy having my dress ride up my hose covered legs. When I arrived at Steve’s house he was

Posted by a TS / CD

By classybiguyaz

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 34.1k 626 4.1k
#2
Tiffanyheels
Trans Couple Straight
Crossdressing intimacy in office 76.7k 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 46.6k 523 2.9k
#5
kimorafoxxsexycd
Gay Couple Trans
Very kinky self care 72.5k 1.0k 2.7k
#6
sissyjamie4daddys
Trans Couple Straight
Sucking appendage in the club 44.0k 456 1.9k
#7
wally4u
Gay Trans Straight for Gay
My Birthday Suprise! 50.4k 272 1.8k
#8
Steve
Straight for Gay Straight Gay
Gym kiss pt.2 48.5k 604 1.7k
#9
curiousladyd
Straight Couple Straight for Gay
First really big appendage 10.0k 357 1.2k
#10
Dedavis
Straight for Gay Straight
House hunting pt 1 38.0k 276 1.1k
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