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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 Encounters and Choices

So last night I finally hooked up with this daddy mans that has been chasing my tail for the last couple of weeks. Daddy mans sent me flowers, candy, n even had Uber eats deliver me din din. Daddy

Posted by a TS / CD

By sissyjamie4daddys

1

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An Unexpected Surprise in the Office Meeting

The Meeting That Got Out of Hand I showed up to the office dressed in my “Supervisor” uniform — black polo shirt tucked neatly into black pants, shiny work shoes. On the outside, I

Posted by a TS / CD

1

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Road Trip Adventures from St. Louis

I love taking lil road trips within bout 5 hours from St Louis MO area. I will post on here n a few other sites to let daddy mens know my itinerary n my route. Now I'm a passable crossdresser

Posted by a TS / CD

By sissyjamie4daddys

2

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An Unexpected Encounter with a Young Stud

Young stud pushed my face down in his lap "Let's see what a great lil cock sucker you really are. It's feeding time for the lil whore" he said as he grabbed the back of my neck n

Posted by a TS / CD

By sissyjamie4daddys

2

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A Flirty Encounter During a Shopping Trip

I'm a lil crossdressing bottom sissy slut who simply LOVES me some daddy mens. I'm NOT completely trans. I still have my lil wand, n I also have a pair of 38D tittys that I love having

Posted by a TS / CD

By sissyjamie4daddys

0

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Unexpected Encounters on a Road Trip

so im an out and about type of gurl i love driving around with by false breast plate and little top on love flashing truckers hehe well i went on a little road trip a state over and decided to make a

Posted by a TS / CD

2

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A Chance Meeting at the Local Bar

I'm known as an easy fuck. I'll suck cock til they are nice n hard n my slobber is all over them. Then I'll either climb on top of your cock n ride it, or get on all 4s n let you pump

Posted by a TS / CD

By sissyjamie4daddys

1

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An Unexpected Visit from Daddy Friends

Im sitting on the couch, tittys getting sucked on by 2 daddy mens as I have their cocks out jacking each on. Both tell.me how great it feels. I lean down n take turns kissing n licking each cock.

Posted by a TS / CD

By sissyjamie4daddys

2

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A Surprise Visit from an Old Friend

I am a bisexual cross dressing man with a wife. Well she was out of town for work so I invited this hot sexy man over fun. I got all cute for him wearing my most sexy stuff knowing I'm a bad

Posted by a TS / CD

By sexycdkimfoxx

2

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An Unexpected Connection During a Hotel Massage

HOTEL MASSAGE TURNED HARDCORE Pt 2 (Sissy Kitty) (continued) As I sucked he surprised me by suddenly eating my ass and sucking my smooth sissy balls. This made me want to cream my panties, but I

Posted by a TS / CD

3

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A Young Boy's Secret Meeting with an Older Man

I'm a young boy who loves crossdressing and being a sissy femboy and playing with older daddies and I was finally able to live out one of my biggest fantasies! I love knowing that I'm

Posted by a TS / CD

1

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An Unexpected Encounter at the Bar

Too big for me! We both swiped and met at a bar then quietly stepped out and went back to his place. We walked through the door and it was on. We were kissing, he was grabbing me, then i reached

Posted by a TS / CD

3

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A Surprising Night at the Bar with a Friend

Ooohhhhh the horror! Met this guy that was a friend of a friend at a bar. End of the night we got are friends left and we got wasted. I had the closest plastic so, "lets just go to my place,

Posted by a TS / CD

1

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A Journey of Self-Discovery at the Theater

I'm a Non-passable Black Sissy Fucktoy. Im feeling like a whore and need to be used. So as usual, I head downtown to the local Sex Theater. I always wear a mask when I'm in Sissy Slut mood.

Posted by a TS / CD

By throatgobbler

0

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A Night Out: New Friends and Fun Conversations

Part 2- This is my first experience with a Shemale. Now I'm outside of the club with Michelle and Anna. We were about to smoke a joint when Anna asked me if I wanted to go back to their place

Posted by a TS / CD

0

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An Intriguing Challenge in Fantasy Football League

SIL saga continues. Having now moved in with him and my stepdaughter our relationship has become intriguing and exciting. He formed a fantasy football league and ask me to join. The league has nine

Posted by a TS / CD

0

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A Unique Connection at the Assisted Living Home

I'm Trans Connie and I want to share why I love old black men and I'm looking on here for my daddy when I was 18 I lived with my aunt in Lafayette we lived in a mostly black community and

Posted by a TS / CD

By Deleted User

1

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A Summer Night Encounter at the Club

Part 1-This is about my first experience with a shemale. I was a 29 year old discreet bisexual white man. I had never been with a shemale before. But, I have watched a lot of porn with them. There

Posted by a TS / CD

0

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Unexpected Encounters in a Hotel Room

Older non passable CD (63) that enjoys sex when dressed with men. Some men like it and some just don't and that is fine. This was actually back in the Craig's Days. Then I was a much

Posted by a TS / CD

0

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Rediscovering Identity After Divorce

I’m a sissy older guy that enjoys being with men. It all started with me marrying young with my high school sweetheart. I was away in the military and I’m built small in the men’s

Posted by a TS / CD

1

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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

D Deleted User “It’s late but I’m down to chill and have a little fun!!” C caniuseu “First time shed intimacy”

John Lee Erwin I am He-Man “Chick with appendage picks me to lick her appendage.” F Freshfresh “Available for connection”

Rank	Author · Category	Latest Story	Views	Listens	Upvotes	Trend
#1	derake14 Gay Straight for Gay Straight	Parking lot kiss	34.4k	629	4.1k	↘
#2	Tiffanyheels Trans Couple Straight	Crossdressing intimacy in office	77.1k	1.4k	3.2k	↘
#3	KestrelElbow9092 Straight for Gay Gay Straight	Beautiful and Black	23.5k	353	3.1k	↘
#4	cnysub Gay Trans Straight	Ads on DoubleList	46.9k	523	2.9k	↘
#5	kimorafoxxsexycd Gay Couple Trans	Very kinky self care	73.1k	1.0k	2.7k	↗
#6	sissyjamie4daddys Trans Couple Straight	Sucking appendage in the club	44.4k	456	1.9k	↘
#7	wally4u Gay Trans Straight for Gay	My Birthday Suprise!	51.2k	272	1.8k	↘
#8	Steve Straight for Gay Straight Gay	Gym kiss pt.2	48.8k	605	1.7k	↘
#9	curiousladyd Straight Couple Straight for Gay	First really big appendage	10.0k	357	1.2k	↘
#10	powers8 Straight Gay Straight for Gay	An absolutely amazing 3 friends	32.5k	318	1.1k	↘

Page 1 of 50 · Showing 1–10 of 500 authors

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