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Transgender Sex Stories – Real Encounters & Passionate Experiences

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Category: TS / CD

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A Night of Unexpected Party Dynamics
Part two of this is not an encounter or interaction story. (Must read part 1) time to party, what could he mean by this? Soon it became apparent as I watched every man there quickly get naked and

Posted by a TS / CD

By davidallen

An Unexpected Connection at the Hotel
I have been in an amazing relationship with my hot GF(24) but every chance I get, i’d love to dress up like a slut and make horny men cum for me either online or in person. I don’t feel

Posted by a TS / CD

By sissynicole1647

An Unexpected Encounter in a Hotel Room
well it all started one day wanted to when I visited a craigslist and notice a add about a guy wanting a bottom to play with and I am a bottom so I replied to his add and some chatting we decided to

Posted by a TS / CD

By f2kinky

Navigating Love and Wealth in Unconventional Ways
I married my limp dicked, worthless piece of shit hubs in 2010. I married his lame ass for 1 reason: I was in love with him for what he could give me n provide for me. Wimpy was financially set for

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Threesome Situation Unfolds
PART TWO OF M/F COUPLE As he ate her pussy, I sucked on his man meat til he was hard as a rock. "Want to help me fuck W" he asked. I thought to myself: hell no. I want that cock in my ass

Posted by a TS / CD

By sissyjamie4daddys

A Unique Encounter with a Couple at Home
I haven't fucked, or penetrated a woman in a very VERY long time. I am strictly dickly. However there are rare occasions that I will share a woman with a man. RARE occasions. I am a passable

Posted by a TS / CD

By sissyjamie4daddys

A Neighborly Gift and Secret Encounters
I've been in love with panties and lingerie since I was a young boy I used to wear my older sister pantys and would cum in them and put them back into her drawer sometimes I would leave them in

Posted by a TS / CD

By Deleted User

An Intimate Bedtime Connection Between Lovers
Laying in bed with a daddy dick in my ass. God daddy's dick feels so good. Daddy pumping away, burying that dick of his, hitting the right spots. Then daddy pulls out n straddles my face, his

Posted by a TS / CD

By Deleted User

A Supportive Couple's Adventure with Their Lover
My wife and I both enjoy cock. I am a very bisexual crossdressing bottom sissy. I have been crossdressing for 8 years now and my wife is very supportive of my feminine ways. I still have sex with my

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Hotel Room Adventure
Responded to a post from a top daddy looking for a gurl to stop by his hotel room for some fun n gaymes. He gave me his room number. He let me in. He was dressed in dark red lingerie. On the bed was

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Journey to a New Life
this is not an encounter or interaction story but more of a dream. From a young age, I can recall laying in bed, closing my eyes and imagining in vivid picture what life I wish to lead. I would

Posted by a TS / CD

By davidallen

Finding Love and Support with Daddy Les
My daddy Les part 1 I came out several years ago to a few family members n friends. They were not surprised as a few of them knew I was a lil flamboyant. I had met an older man who treated me like

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Connection with a Workout Partner
I read a post from a young stud who was looking for a "queer feminine guy to work out with". I responded to his ad n he invited me over to his place. He was very muscular. OMG n sexy! He

Posted by a TS / CD

By sissyjamie4daddys

A Night of Intimacy and Connection
Laying in bed with a daddy dick in my ass. God daddy's dick feels so good. Daddy pumping away, burying that dick of his, hitting the right spots. Then daddy pulls out n straddles my face, his

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Connection at the Bar
Met a nice young stud last night at a bar. He is early 20s with a nice curved cock. He walked up to the table I was sitting at with 1 of my older daddys. The young stud asked if me n daddy were

Posted by a TS / CD

By sissyjamie4daddys

A Morning Coffee Meeting with a New Sugar Daddy
I'm a happy lil bitch this morning I met a new sugar daddy yesterday. His name is Sam, an older married local businessman who is very 🤑💰 wealthy. I met him thru a diff site. We spent most

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Visit from an Old Friend
The ad was simple n straightforward: 'married male not getting any at home. Need a feminine guy to take care of my pipe weekly'. I responded, we exchanged pics, he was at my house 2 hours

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Visit from Young Friends
Oh my fucking ass pussy just got double stuffed again n it felt fucking amazing!! I was in bed sucking a sugar daddys cock just sugar daddy n me this morning after a long night of fucky sucky time. I

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Night Out with New Friends
I'm a size queeny sissy gurl always looking for the next big cock to suck or fuck my lil ass pussy to stretch me the fuck out. I have had the honor of sucking on some of the biggest thickest

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Encounter at the Club
Monday evening I decided to go on a cock hunting expedition to a local HEY club. I was a lil buzzed so I called an Uber to take me to the club. I got to the club bout 7ish. There were prolly bout

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 Couple
The fast and furious 60.9k 862 4.4k ↘
#2
Tiffanyheels
Straight Couple Gay
Girlfriend and her attractive daughter 139.7k 2.1k 4.0k ↘
#3
kimorafoxxsexycd
Gay Trans Couple
Swallowed my bfs meal at lunch 129.8k 1.4k 3.5k ↘
#4
cnysub
Gay Trans Straight
Part 1 Nude Performer 76.7k 705 3.3k ↗
#5
KestrelElbow9092
Straight Gay Couple
Picnic Fun 49.0k 520 3.3k ↘
#6
sissyjamie4daddys
Trans Couple Straight
I love water 72.2k 488 2.0k ↘
#7
wally4u
Gay Couple Trans
I Guess He Did Have To Go! 67.7k 310 1.9k ↘
#8
butchmax
Straight Gay Couple
I was FED UP 88.3k 629 1.7k ↗
#9
Steve
Straight for Gay Straight Gay
Gym kiss pt.2 53.8k 644 1.7k ↗
#10
powers8
Gay Straight Straight for Gay
A fantasy come true 83.5k 670 1.7k ↘
Page 1 of 50 · Showing 1–10 of 500 authors

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