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Transgender Sex Stories – Real Encounters & Passionate Experiences

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A Surprising Discovery During a Sleepover
I didn't know i liked cock untill a school buddy stayed at my house, We slelp in a guess room and a pull out bed, I would lay across the bed and he would be in the floor with covers watching

Posted by a TS / CD

By intowhat

An Unexpected Encounter at the Motel
The mood was set, candles lit, lights low. I Slowly I navigated myself to my motel door. Carefully walking in heels that were a little advanced for me. A subtle knock sounded and I opened door,

Posted by a TS / CD

By Anonymous

Always Ready for Surprise Visits from Daddies
I am ALWAYS in the mood to suck n fuck. 24 hours a day, 7 days a week. Don't matter if it's 9am, 2pm, 7pm, or 2 in the morn, I'm ALWAYS ready for daddy mens cock n cum. Hell, I have

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Game Night with Friends
One of my daddy mens invited me over to his place for gayme night. Daddy mans n his friends usually play poker, which turns out to be pokeme night. Which I simply LOVE. When I got to daddy mans place

Posted by a TS / CD

By sissyjamie4daddys

Navigating an Unconventional Marriage Dynamic
In 2010, I married the local town slut. I knew she was THE slut before we got married. She is 9 years younger than me, and I knew she sucked and fucked others. When I would kiss her, she would tell

Posted by a TS / CD

By sissyjamie4daddys

Exploring Identity in Therapy Sessions
I go to a therapist once a month. I eventually got the courage to tell him about me secretly crossdressing for some time now. I told him I didn’t have the courage to go out dressed up. I

Posted by a TS / CD

By Anonymous

A Unique Shopping Adventure and New Encounters
Part 2. I walked to my car. I was putting my bag of stuff in my car. My dress was riding up so I pulled it down. I was about to start my car and go back home. This was my first time in public dressed

Posted by a TS / CD

By Miniho

An Embarrassing Mishap During a Hospital Visit
OMG. I just have to share this embarrassing story of my trip to the hospital ER. Mind you, this took place a few years back. So I was at this daddy mans place, giving him a lil sucky sucky. Now, when

Posted by a TS / CD

By sissyjamie4daddys

A Journey of Self-Discovery Through Fashion
MY personal experiences over the past 30 yrs! I will give you MY 411 and try to be brief yet brutally honest okay?...I DO believe in honesty and candor whether it helps or hurts....so YOU HAVE BEEN

Posted by a TS / CD

By subsissy4you

An Unexpected Reunion at My Old House
Part 2). De’vone and I had been together for a couple months and he had moved in with me. He had insisted on me getting 40 Ds breast implants even though I knew he was seeing other gurls and

Posted by a TS / CD

By OspreyGrove7318

A Journey of Self-Discovery After Divorce
Part 1). So I got married at a young age. I was only 22 and my wife was a couple years older but that doesn’t really mean much for my story. She was beautiful she had big tits and a great ass

Posted by a TS / CD

By OspreyGrove7318

Exploring the World of Sugar Daddy Relationships
I don't date. I hookup, meet daddy mens for strictly sucky fucky time. I'm a trans gurl navigating thru this journey of life as a female, a woman, a gurl for the past 8.5 years. I have

Posted by a TS / CD

By sissyjamie4daddys

A Night of Unexpected Visitors at Home
I might as well have a revolving door in place of my front door. I love to be used n abused by daddy mens for their pleasure. I am that easy piece of ass, that guaranteed fucktoy. I have daddy mens

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Guest Arrives for a Night In
Well, for 6 years, I've been trying to get a dick in my ass. Tonight, I answered an ad, and the guy actually showed up!!! Holy fuck. So he walked in my door, and I was already ass up bent over

Posted by a TS / CD

By MarmotCloak4660

Exploring Intimacy: A Journey of Connection
first time cd part 3 - After baby cleans madam's hole and sucks on her cock some more, I tell baby to lube up his boy pussy for mamdam and put some lube on mamdam's cock. Then I tell baby to ride

Posted by a TS / CD

By Anonymous

An Unexpected Encounter on the Couch
first time cd part 2 - I get up on my knees but still straddle you. I tell you to lift up my skirt and massage my lace covered ass, work you hands up and down my legs, as you are doing this I press

Posted by a TS / CD

By Anonymous

An Exciting First Meeting at Home
first time cd part 1 - We chat back and forth and decide to meet at my place. You arrive and I greet you at the door wearing a red silky camisole, short pleated red plaid skirt, black thigh highs

Posted by a TS / CD

By Anonymous

A Surprise Visit from My Sugar Daddy
I got a text from one of my sugar daddy mens that lives out of state. He told me to clear my calendar, that he would be in town the 1st week of July n wanted, or as he said, needed to fuck my brains

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Encounter at the Adult Theater
So I love dressing up in women's low cut dresses. I like wearing lace bras and thongs with lace garter belts with thigh high stockings. I like when guys look at my ass. I were on occasion sexy

Posted by a TS / CD

By Miniho

A Unique Experience with Generous Daddies
I scrolled thru the ads posted by daddy mens that are looking for a crossdresser, a trans gurl, or just a gay bottom to stick their cock into. The daddy mens just want a wham bam thank you mam. I am

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
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derake14
Gay Straight for Gay Straight
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Tiffanyheels
Trans Couple Straight
Crossdressing intimacy in office 77.2k 1.4k 3.2k
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KestrelElbow9092
Straight for Gay Gay Straight
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Ads on DoubleList 47.1k 524 2.9k
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kimorafoxxsexycd
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Very kinky self care 73.3k 1.1k 2.7k
#6
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Sucking appendage in the club 44.5k 457 1.9k
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My Birthday Suprise! 51.4k 273 1.8k
#8
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Straight for Gay Straight Gay
Gym kiss pt.2 48.8k 605 1.7k
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curiousladyd
Straight Couple Straight for Gay
First really big appendage 10.1k 358 1.2k
#10
powers8
Straight Gay Straight for Gay
An absolutely amazing 3 friends 32.6k 319 1.1k
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