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Transgender Sex Stories – Real Encounters & Passionate Experiences

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Category: TS / CD

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A Crossdresser's First Encounter at the Motel

I have been a crossdresser ever since I could remember but my first experience with a man came when I was 19. I was looking through personal ads section on Clist for weeks until one ad caught my

Posted by a TS / CD

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A Unique Gathering at the Football Watch Party

I am a very submissive Asian CD and getting gangbanged has been my dream forever so I invited 5 daddy's I've met through the years to a football watch party and have a little fun. I had my

Posted by a TS / CD

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Exploring New Connections and Personal Growth

straight guy all my life, masculine tattoos Harley people . women married years. kids whole box thing. I have had a guy give me bj years ago. . I like pussy. younger . I been single 8 yrs met a

Posted by a TS / CD

By richardintime6969

0

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Exploring New Fantasies: A First Meeting

I am new crossdressing so I hadn’t been able to meet guys and explore my fantasies. Keeping it on the DL big time. Well I had decided one night I was tired of jerking off to porn loving other

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A Journey of Self-Discovery and Connection

I’ve been crossdressing for as long as I can remember but never really thought about being with a man until a couple of years ago. I went on a few site trying to find a man to dress for but all

Posted by a TS / CD

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A Unique Encounter in a Hotel Room

I had always crossdressed but it was always alone at home and I never ventured out but that was about to change. My fantasy was to become a cum-loving slut under the direction of a strict mistress.

Posted by a TS / CD

By stephanie1255

0

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A Mysterious Late Night Visit with a New Friend

I didnt want to brag but my BBC Mommy let me see her 2 night in a row. The first night i talked to her it was after midnight when made a date for her to host me. Now im an older average daddy by day

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By rachelbottomcd

0

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Old Friends Reconnect in a Small Town

old high school friend I live in a small town that would not understand what i do. so for the most part i hide it . with that said i had a old high school friend stop by for a visit. he had just

Posted by a TS / CD

By samantha1965

1

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An Unexpected Revelation at Home Leads to Change

When I was about 40 I met my wife sex was good I went to work one day while she went through my computer she called me at work saying we need to talk I found out you're gay what she was flipping

Posted by a TS / CD

By daviddickson

0

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Unexpected Connection at a Rest Area

I'm a straight acting male in public. I always wear fem clothes under my manly clothes, you know, just in case. So last week I was out of town on business. I stopped at a rest area to tinkle. I

Posted by a TS / CD

By sissyjamie4daddys

0

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An Unexpected Night with New Friends

My first threesome: Back during Craigslist days, I had hooked up w/ this 1 guy a year or 2 prior & we had fun, but he vanished off Craigslist (found out he had moved for a little while out of

Posted by a TS / CD

By WalrusHaven8010

0

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A Surprising Encounter in a Sundress

I started putting on my sister and stepmothers cloths and make up when I was a senior in high school. I had long hair and my girlfriend used to comment on how feminine my lips and eyelashes were.

Posted by a TS / CD

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A Beach Town Encounter with a Younger Man

Well, I just have to tell this true story while it is fresh in my mind. I had placed an ad in DL as a very fem submissive sissy slut looking for tops who like long sessions of using my mouth, lips,

Posted by a TS / CD

0

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Unexpected Connection Between Friends on the Couch

...well as a lay there mouth fucked and pussy fucked I felt I had my fill for the evening. The 2 men left and as they did I noticed another CD on another couch had been watching all of this. I sat

Posted by a TS / CD

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A Winter Encounter at the Adult Arcade

Been CDing on and off for years. There is a great Adult Arcade in CT that I visit when I get the urge. I dress fully. I'm a tall gurl at 6 foot and hwp. The place has GH and also a large

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A Nervous First-Time Encounter with a Dominant Date

I love dressing up in woman's clothes and lingerie. It makes me feel so bad! I slowly got into crossdressing over the years and eventually got into dildo play as well. One night I was feeling

Posted by a TS / CD

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A Bold Encounter with the Neighbors

I love turning out straight men. I am a bi 24yo white TS slim with perky 20k tits and a 6in shecock sholder mid back leingth hair black with blond highlights. I have a thing for turning out straight

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By sub79_whtbottom

0

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Unexpected Meeting at the Repair Shop

I am a CD now. I am a white male never had sex with another man. But I was low on cash and my truck broke down so I took it to a repair shop. The shop was owned by a Black man. He checked it out then

Posted by a TS / CD

0

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An Unexpected Experience at the Doctor's Office

Well I answered an ad for a “doctor” that was looking for new patients. He replied come to my office. So on the day I came to his office. He greeted me and showed my to the room. He told

Posted by a TS / CD

0

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An Unexpected All-Male Baby Shower Gathering

I got invited to an all male baby shower, aka bukkake party, last weekend. I was the center of attention as 7 daddys surrounded me, each with their hard cocks out n jacking their cocks. I begged each

Posted by a TS / CD

By sissyjamie4u

0

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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

S sexysexaddict23 “Made love to my mother in law”

Mouth4You “First time sucking penis” S samwhycantwe “Intentional intimacy” C caniuseu “First time shed intimacy”

Rank	Author · Category	Latest Story	Views	Listens	Upvotes	Trend
#1	derake14 Gay Straight for Gay Straight	Parking lot kiss	35.0k	633	4.1k	↘
#2	Tiffanyheels Trans Couple Straight	Crossdressing intimacy in office	77.9k	1.4k	3.2k	↘
#3	KestrelElbow9092 Straight for Gay Gay Straight	Beautiful and Black	24.0k	355	3.1k	↘
#4	cnysub Gay Trans Straight	Ads on DoubleList	47.7k	529	2.9k	↘
#5	kimorafoxxsexycd Gay Couple Trans	Very kinky self care	74.4k	1.1k	2.7k	↘
#6	sissyjamie4daddys Trans Couple Straight	I love water	45.5k	461	1.9k	↘
#7	wally4u Trans Gay Straight for Gay	Pre-Halloween CD Dress Up! Part 1	52.5k	275	1.8k	↗
#8	Steve Straight for Gay Straight Gay	Gym kiss pt.2	49.2k	612	1.7k	↘
#9	curiousladyd Straight Couple Straight for Gay	First really big appendage	10.2k	359	1.2k	↘
#10	powers8 Straight Gay Straight for Gay	Back with Michelle and Lisa	34.3k	351	1.1k	↘

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