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Transgender Sex Stories – Real Encounters & Passionate Experiences

Welcome to DoubleList’s collection for trans sex stories, where our users share their real, salacious experiences. Your secret encounters are always safe with us because your identity will be 100% anonymous. So, come on in and add your steamy trans erotic stories; we can’t wait to hear them.

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An Unexpected Intimacy After the BBQ
Ray n Tom BBQ part II Tom n I locked into a 69, n Ray lined up behind me, guiding his cock into my asscunt. "That's it baby, take that dick" Ray said as he slid his cock in me. I was

Posted by a TS / CD

By sissyjamie4daddys

A Chance Encounter at the Hotel Bar
I recently stayed at a nice hotel while on business. This is usually the only time I get to dress en femme. This particular time I had a few glasses of wine in my room and got up the courage to go to

Posted by a TS / CD

By Guitarpicker.mb61

An Unexpected Encounter in a Parking Garage
My ad was simple n straight to the point: looking to suck cock in public. I got several responses n chose a young stud to meet at a downtown parking garage at 6am. I arrived a lil before 6, n hopped

Posted by a TS / CD

By sissyjamie4daddys

Exploring Connections with Older Partners
I have ALWAYS been attracted to older men, older daddy's if you will. I have a major fetish when it cums to daddys that are 60-90 years of age. I will do anything, n I mean ANYTHING for them.

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Visit from a Charming Daddy
I met a kinky daddy from here a few days ago. I invited him to my house. The minute daddy walked in, he was a horny dog. Daddy kissed me, grabbed my legs pulled me to him n started humping my legs

Posted by a TS / CD

By sissyjamie4daddys

Memorable Connections Over Labor Day Weekend
Labor Day weekend part:2 Saturday night fell asleep with bbc still inside me.. woke up about 4:45am when he fell out of me.. i felt empty and hallow!! He stretch me out to accept his bbc and i

Posted by a TS / CD

By modoc243

A Fun Labor Day Weekend Pool Gathering
Labor day weekend part 1: My name is Sammie.. i am 28yo Asian and black decent.. about 70% Asian and 30% black.. 5’5” and 125-130lbs.. long long black hair that reaches my pussycrack..

Posted by a TS / CD

By modoc243

An Unexpected Visit in Bellingham
Good morning Bellingham I call a add on doublelist.com asexy trans wanted me to cum over so I did walked through the door omg she was hot with a long black cock I dropped to my knees and started

Posted by a TS / CD

By DingoKnot6608

An Unexpected Encounter with Parents at Home
pt2 how my parents found out i was a sissy crossdresser. he started finger fucking me good and then he said open wide i thought he was jerking off and about to cum when all of a sudden he shoved his

Posted by a TS / CD

By ababycd

Unexpected Morning Visits from the Neighbor
Every day for the last 2-2.5 weeks, as soon as my neighbors wife leaves for work, her husband has been coming over to get his dick wet. He will come over for a few hours in the morning, get his dick

Posted by a TS / CD

By sissyjamie4daddys

Adventures at the Local Store
There is an old saying that practice makes perfect. I guess I am now the perfect cock sucking sissy. I have been sucking cocks for 12+ years, and have been a cock sucker on a daily basis. I stop by

Posted by a TS / CD

By sissyjamie4daddys

A Surprising Meeting at the Local Theater
I love getting my ass stretched and gaped open. The thicker the dick the better it feels. I stopped at a local porn shop yesterday. I went into the theater and sat down. Soon a man came over and sat

Posted by a TS / CD

By sissyjamie4daddys

Unexpected Encounters at the Retirement Home
I have met my share of extremely horny n raunchy older men over the years. N I have attempted to please each of them anyway I can. But let me tell you bout my time at an old folks home. So my sister

Posted by a TS / CD

By sissyjamie4daddys

A Night Out at the Dance Club with Daddy
When I finally came out of the closet, I came out in a BIG way. I was dating an older daddy, an had moved in with him, kinda. I was spending like 4-5 nights a week at his place. He lived on a few

Posted by a TS / CD

By sissyjamie4daddys

A Surprising Reunion at the Party
I woke up this morning feeling a bit horny. I jumped in the shower and was thinking about going to the porn shop. I was getting my clothes and lingerie out on my bed. I had just got some red

Posted by a TS / CD

By Miniho

A Chance Encounter at the Shopping Mall
I was out running a few errands today. I was shopping for some new outfits, when I noticed an older, handsome gman. I politely smiled at him n went on my way. I was at a lil strip mall, so I hit a

Posted by a TS / CD

By sissyjamie4daddys

A Journey of Self-Discovery and Connection
So I am 99.999% a sissy bottom bisexual crossdresser. I would much rather have sex with men. The last 20-25 times I have had sex, maybe once with a woman, but only if we shared a cock. I have been

Posted by a TS / CD

By sissyjamie4daddys

A Dreamy Encounter at the Bookstore
I just met the daddy of my dreams. Ok, ok. Daddy flav of the hour. He has prolly the closest thing to the perfect cock I have seen in the last 3 months. Daddy has a smooth cock, shaved smooth balls n

Posted by a TS / CD

By sissyjamie4daddys

A Night of Surprises in Crossdressing
I’ve always thought that lingerie and thigh highs were sexy as hell. I've never crossed dressed or had a desire to but one drunken night I ordered a sexy outfit. In a couple days when it

Posted by a TS / CD

By mball70220

A Sweet Reunion with My Sugar Daddy
One of my sugar daddys was in town earlier this week. I cleared my calendar so I could spend some time with him. Daddy was here on bizness, n for some recreational activity. This sugar daddy is 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
Straight for Gay Couple Straight
I couldnt refuse the temptation. 49.9k 738 4.3k
#2
Tiffanyheels
Straight Couple Trans
Finally had intimacy with ex mother in law 100.9k 1.7k 3.4k
#3
KestrelElbow9092
Straight Gay Straight for Gay
A chance meeting. 36.2k 429 3.2k
#4
kimorafoxxsexycd
Gay Straight Couple
Bf was a sweetheart today 102.2k 1.2k 3.1k
#5
cnysub
Trans Gay Straight
My boyfriend/ Master/partner 61.3k 618 3.0k
#6
sissyjamie4daddys
Trans Couple Straight
I love water 61.0k 470 1.9k
#7
wally4u
Gay Trans Straight for Gay
My Night At The Anvil... Part 1 58.1k 279 1.8k
#8
Steve
Straight for Gay Straight Gay
Gym kiss pt.2 52.0k 630 1.7k
#9
powers8
Straight Straight for Gay Gay
My greatest vacation ever 52.2k 487 1.3k
#10
butchmax
Straight for Gay Couple Straight
My Wife Got Sick 60.0k 472 1.3k
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