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Transgender Sex Stories – Real Encounters & Passionate Experiences

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Category: TS / CD

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A Surprising Encounter with My Boss at Home
I'm a CD, one Saturday morning, day off work I was getting dressed up hoping to meet someone later in the day. I heard a knock, at the door, I answered it all dressed up, figured it was probably

Posted by a TS / CD

By Deleted User

An Unexpected Encounter at the Hotel
I am a sissy, bottom crossdresser, who loves worshipping alpha top men. I live my life as a fem 24-7-365. I do what the wife or girlfriend won't do. Last week, I met a small group of men, 4

Posted by a TS / CD

By sissyjamie4u

Exploring Submission and Pleasure in a Unique Encounter
Sub CD part 2: She slapped me hard, a reminder that she expected full cunnilingus regardless of any personal issues I had with being painfully penetrated by a large hard cock. I tried to return to

Posted by a TS / CD

By theonlymoai

Exploring a Submissive Dynamic in Intimacy
Sub CD part 1: At least this part was familiar, so far. I was humbly kneeling as I serviced his hard cock, while she watched intently. My hands were still free, so I was able to use them to caress

Posted by a TS / CD

By theonlymoai

A Surprise Cabin Getaway with Friends
So I get a text from a young stud that I have hooked up with several times. He is 26 years old, nice bod, great cock with lots of stamina, and is a multiple heavy cummer. He has a 4 day lil vacay, as

Posted by a TS / CD

By sissyjamie4u

Exploring New Dimensions in a Unique Relationship
I been seeing a guy that has a nice big cock. We have been seeing each other for about a year and half now. At first it was just me sucking him off and swallow his cum. He had girlfriend that would

Posted by a TS / CD

By OlderMaleguy

An Unexpected Meeting Between Crossdressing Friends
Was just today and man was it fun. Put an ad on here for other guys that like to crossdressing and play. Had another guy answer and he was about the same age (59), he's single and could host and

Posted by a TS / CD

By Deleted User

An Unexpected Encounter with a Married Man
Hello everyone, I am a discreet wanna try being a total bottom yet sub,fem crossdresser: I have met online with a married top,Dom married black mature man at double list. Which I have had only 2

Posted by a TS / CD

By Katie

A Mysterious Late Night Encounter
There was one night where I had the house to my self, so I thought there would be no better time to dress up and make a post looking for a nice dick. I’m a slightly chubby CD with a fat ass, I

Posted by a TS / CD

By psychoween89

A Halloween Party Transformation and Connection
I am a closeted bi man who has been wearing panties full time for years. Recently I went to a Halloween party with friends and felt like going all out more than I ever have. I got a Minne Mouse

Posted by a TS / CD

By gpo52

Nostalgic Nights at the Bookstore
Do u remember house of movies and house of books on brookpark? Long time ago I was young and attractive 5' 9 140 beautiful curly Brown hair I would wear a beret so I would have bangs

Posted by a TS / CD

By Deleted User

Memories of Nights at the Movie House
Do u remember house of movies and house of books on brookpark? Long time ago I was young and attractive 5' 9 140 beautiful curly Brown hair I would wear a beret so I would have bangs it

Posted by a TS / CD

By Deleted User

A Weekend Escape in a Chicago Hotel Suite
Part 1. Asian CD here. Got a proposition from one of my regular hookups. He said he was going to be going out of town for a week but he wanted me to join him (it was a couple hours drive away).

Posted by a TS / CD

By de_kaleidoscope2

A Surprising Encounter in the Shower
PART 3 I tell him to come in the bathroom with his eyes closed. That he must keep his eyes closed and that ill help him in the shower.I undressed him he has nice little cock. I grab a wash cloth and

Posted by a TS / CD

By Deleted User

Unexpected Encounter in a Hotel Room
PART 2 His first too ropes went straight down my throat almost instantly he filled my mouth. His cum spilling everywhere. He let go of my head as I was trying to swallow he said he wasn't done

Posted by a TS / CD

By Deleted User

A Surprising Meeting in the Park
I was looking to meet up with a sissy or cd for a blowjob and ended up getting a response to my post. I drove out to his house and he was dressed up nice and slutty :). He had me sit on the couch and

Posted by a straight man

By PumaCrest3552

Sisters Planning a Fun Party Together
So I thought I knew how to please a man continued: I smiled at my sister and told her that father hung used to make me lick the cum out of moms pussy after he was done fucking her. My sister gasped

Posted by a TS / CD

By OspreyGrove7318

An Unexpected Reunion Leads to Adventure
this is my story up to now.. i have met about 15 guy from this site but learned how to make sure i get what i want to. don't get me wrong i love men and i enjoy getting them off but i still have

Posted by a TS / CD

By greatime00

Embracing My True Self at Pride Week
my story keeps going. now after the adult store trip which i have done a few times now i am still afraid to come out of my closet and face the world as the sissy whore i am. don't know why

Posted by a TS / CD

By greatime00

A Journey to Self-Discovery at the Adult Store
here is the next part of my story. i am the guy that was in the motel when 4 guys walked in and i was wearing my wife panties...now i have got divorce quit my job and became a sissy whore but i was

Posted by a TS / CD

By greatime00

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
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I couldnt refuse the temptation. 48.8k 732 4.3k
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Tiffanyheels
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Finally had intimacy with ex mother in law 99.1k 1.7k 3.4k
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A chance meeting. 35.4k 427 3.2k
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My Birthday Surprise 59.6k 604 3.0k
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sissyjamie4daddys
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I love water 60.0k 468 1.9k
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wally4u
Gay Trans Straight for Gay
My Night At The Anvil... Part 1 57.8k 279 1.8k
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Steve
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Gym kiss pt.2 51.8k 629 1.7k
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powers8
Straight Straight for Gay Gay
My greatest vacation ever 50.5k 472 1.3k
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butchmax
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My Wife Got Sick 58.4k 470 1.3k
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