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Transgender Sex Stories – Real Encounters & Passionate Experiences

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Category: TS / CD

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An Unexpected Encounter with the Delivery Guy

I'm a 28 yr. old passable submissive cd with an older daddy 62 yrs. old. He is helping me with my transformation into a female but I have to keep my male parts, which I want to do anyway.

Posted by a TS / CD

14

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A Playful Encounter in the Bathroom

Pt 2 He moves my hand to his now fully erect cock. I’m trembling with excitement I’ve never felt anyone’s but mine. It’s so much bigger and veiny and so hard. I want to suck

Posted by a TS / CD

14

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A Rainy Day Ride Leads to Unexpected Connection

Being unemployed without a car was lame. I was walking or taking the bus everywhere. One day when I was walking around in the rain turning in job applications a car pulled up next to me. I figured

Posted by a TS / CD

10

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A Unique Bond: Exploring New Dynamics Together

My wife loves watching me sucking cock and getting my boi pussy fucked. Shell sit there n watch, direct my daddy how to fuck me, n encourage him to fuck me like I'm a cheap whore n tell me to

Posted by a TS / CD

By sissyjamie4daddys

7

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A Surprising Night at the Gay Bar

Last night I got dolled up and decided to go out to the gay bar. Soon as I got there I had several men tell me I'm sexy and cute . Well I ran into my ex friend boyfriend and I said I did not

Posted by a TS / CD

By kimorafoxxsexycd

7

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Unexpected Assistance During a Late Night Drive

I was going to meet up with a rugged good looking top man when I got a flat tire. It was bout 1130 at night in the middle of bum fuck Egypt (ok, it was Illinois). I texted daddy that I had a flat

Posted by a TS / CD

By sissyjamie4daddys

15

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An Unconventional Date Night at the Theater

I am a crossdresser and love to suck cock. I crave cum in my mouth. And I have a girlfriend that likes to watch me suck guys off. It gets her off watching. We go to adult theaters with me dressed

Posted by a TS / CD

By Tiffanyheels

13

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A Night of Fantasy in a Hotel Room

Hi Jenny, I fantasize about your pussy. I close my eyes and I see it nestled between to perfectly shaped spheres of meat, slightly darker in tone then the surrounding skin, puckered and subtly

Posted by a TS / CD

3

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Unexpected Connections at Game Night

I got invited to game night at a daddy mans house. There were 6 plus me. N what a variety of daddy mens: young bucks, older daddy mens, white n black daddy mens. The menu was quite apatizing to say

Posted by a TS / CD

By sissyjamie4daddys

4

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Adventurous Encounters with Unique Treats

I swear I must be the dirtiest slut round here. I get ALL the kinky daddy mens. I have daddy mens that like to jerk off in my coffee n I drink it. Yummy goodness to the very last drop I may add. I

Posted by a TS / CD

By sissyjamie4daddys

3

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An Unexpected Visit from a Neighbor

What an absolute gorgeous day out today. Shorts n a lil top wearing weather. I decided to open my windows n let the nice breeze in as I cleaned my house. A few minutes later there was a knock at my

Posted by a TS / CD

By sissyjamie4daddys

6

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Unexpected Meeting at Starbucks with Daddy

I met daddy off here at a Starbucks near his house. Daddy told me he was married and he was just looking for some company. His wifey pooh worked and lived in Washington DC. She was some big shit with

Posted by a TS / CD

By sissyjamie4daddys

3

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Exploring Power Dynamics in Relationships

I love stroking off men. Is there a better power struggle than holding a mans cock in your hands n jacking that cock til he explodes all over you? Getting a firm hold on those cum filled balls, as

Posted by a TS / CD

By sissyjamie4daddys

6

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A Memorable Dinner Date and Hotel Encounter

I was on Yahoo Messenger. One morning made a hookup successfully. Dinner date. So I shaved my legs and genital area. Date at seven. At six put on my black Bali panties and white bra. My Little Color

Posted by a TS / CD

14

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A Mysterious Ride to Daddy's Place

So like yesterday I was just chilling at home when one of my daddy mens texted me. "Be ready at 2. I will have someone pick you up. She's gone til tomorrow afternoon" is all the text

Posted by a TS / CD

By sissyjamie4daddys

3

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A Unique Coffee Date with an Older Gentleman

I had a date with a very kinky older daddy mans last night. Daddy mans is in his mid to late 60s, n enjoys the kinky side of life. I stopped by his house to get my freak on. Daddy mans was drinking

Posted by a TS / CD

By sissyjamie4daddys

3

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An Unexpected Encounter at the Doctor's Office

I always thought that the encounter me and my wife of eighteen years had about seventeen years ago. Was made up on the internet. My wife had an appointment to see her gynecologist. The same guy she

Posted by a TS / CD

15

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A Serendipitous Meeting by the Lake

My first encounter happened while camping. I had a friend who couldn't get there until the next day so I started getting the campsite ready. There was this young guy sitting on some rocks near

Posted by a TS / CD

18

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An Unexpected Encounter with a Friend

Part 2 He is using my mouth like a pocket pussy. Knowing full well I can’t do anything but comply because of the situation with wife. In and out, in and out slobbering and eyes watering I just

Posted by a TS / CD

11

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Finding Freedom During Her Business Trips

My ex wife was a big mistake. I rushed into the marriage just because all my other friends were getting married. She was gorgeous don’t get me wrong and she actually made really good money but

Posted by a TS / CD

8

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Top Authors

Discover the most engaging creators on Doublelist — ranked by views, listens, and upvotes, with fresh voices breaking in every week.

RISING AUTHORS ON DOUBLELIST See all

L LucyV “I'm a romantic trans woman” U uhostshysub “what do you have for homework?” I itshugetwink “🔒🍑 Asian Billionaire Bus And He Begged Me To Stay — Asian Daddy Part 1”

Daze “Just a real woman looking for love ❤️”

Rank	Author · Category	Latest Story	Views	Listens	Upvotes	Trend
#1	derake14 Gay Couple Straight for Gay	He wanted intimacy twice a day	77.0k	1.0k	4.6k	↘
#2	Tiffanyheels Straight Couple Trans	Parlors in Japan	172.0k	2.4k	4.3k	↗
#3	kimorafoxxsexycd Trans Gay Couple	I did some very mischievous things.	156.7k	1.6k	3.9k	↗
#4	cnysub Gay Couple Trans	The observer from DoubleList	104.7k	812	3.7k	↘
#5	KestrelElbow9092 Gay Couple Straight	Her Boyfriend.	77.0k	661	3.6k	↗
#6	butchmax Straight Gay Couple	My Husbands Best Friend	118.4k	805	2.1k	↗
#7	sissyjamie4daddys Trans Couple Straight	I love water	84.3k	496	2.0k	↘
#8	Dedavis Straight for Gay Straight	Super Bowl group event part six	102.0k	704	2.0k	↘
#9	wally4u Gay Couple Trans	Missed The Fine Print! BIG TIME!	73.0k	330	2.0k	↘
#10	Steve Straight for Gay Straight Gay	Doublelist fan	57.5k	677	1.8k	↘

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