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Transgender Sex Stories – Real Encounters & Passionate Experiences

Welcome to DoubleList’s collection for trans sex stories, where our users share their real, salacious experiences. Your secret encounters are always safe with us because your identity will be 100% anonymous. So, come on in and add your steamy trans erotic stories; we can’t wait to hear them.

Category: TS / CD

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A Surprising Connection During a Quiet Weekend

It was supposed to be a long and quiet holiday weekend in the barracks. A lot of the Marines across the base were spending time with family or friends off base. My roommate was going to

Posted by a TS / CD

0

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An Unexpected Visit Leads to Surprises

My encou ter happened when I was home alone and dressed up very sexy. I was wearing black sheer thigh highs, over the knee boots short black mini skirt, leopard print bra with my EEE breast form and

Posted by a TS / CD

By doubletrouble56

0

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Meeting the Alpha: A Surprising Connection

We met on a dl mfm ad, You were a manly man, over 6 feet tall and built thick, your big hairy arms and chest left no doubt that you were probably very well endowed. I’m no slouch at

Posted by a TS / CD

By sissyshapeshifter

0

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Meeting the Alpha Male: A Surprising Connection

We met on a dl mfm ad, You were a manly man, over 6 feet tall and built thick, your big hairy arms and chest left no doubt that you were probably very well endowed. I’m no slouch at

Posted by a TS / CD

By sissyshapeshifter

0

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A Night of Unexpected Revelations at a Party

Hi my name is TS Jennifer I was a beginning transsexual I had just turned 18 and had been left inheritance I was all alone in the world so I took my money had a boob job and ask job in a facelift so

Posted by a TS / CD

By tsjennifercute

0

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An Unexpected Encounter at the Adult Theater

I just had the most amazing experience with a Trans guy in the adult theater in Austin. I fave just fulfilled my fantasy. I was in the ATA in Austin. I walked into one of the booths and there she was

Posted by a straight man

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An Unexpected Meeting in a Dimly Lit Room

Hi. Im a CD slut. Not passable but act very fem. I met this guy from a post on here. He was hosting in a disclosed location. Dim lit room(it ended up not being so dark). I got there and he was

Posted by a TS / CD

By Deleted User

0

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An Unexpected Encounter on the Couch

I hooked up with a young stud last week. We exchanged pics, and texts. He had what I wanted; a nice thicky thick cock that looked delish. I gave him my addy, and he was at our house in 30 minutes.

Posted by a TS / CD

By sissyjamie4u

0

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Embracing My True Self: A Personal Journey

Where to begin? Hmm let's see. All those years wasted on being a straight white male, marrying a woman, having 2 children, and yet, not happy. Then, becoming the fem I am today. Why did I wait

Posted by a TS / CD

By sissyjamie4u

0

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A Late Night Connection on the Porch

We met on DL and his post was an older local man just looking for m2m. We eventually exchanged numbers and he reminded me he was in his 50s and I assured him that aroused me. I told him how I love to

Posted by a TS / CD

0

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Navigating the Challenges of Online Dating in Canada

I'm a passable cd who advertises here, usually with a face pic. I'm only availble a couple days a month and make it a point to specify the days when I can play. About 80% of replies are

Posted by a TS / CD

By IbisFlint8527

0

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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

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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

0

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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

0

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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

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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

0

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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

1

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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

0

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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

0

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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

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

J janee1 “An Unexpected Meeting That Turned Into Something Special”

Olivia “The message I almost ignored”

cnybottom “I became a gay fan” L LucyV “I'm a romantic trans woman”

Rank	Author · Category	Latest Story	Views	Listens	Upvotes	Trend
#1	derake14 Gay Couple Straight for Gay	First true anonymous intimacy	77.8k	1.0k	4.7k	↘
#2	Tiffanyheels Straight Couple Trans	Intimacy with ex mother in law	174.8k	2.4k	4.3k	↗
#3	kimorafoxxsexycd Trans Gay Couple	Home alone	158.0k	1.6k	3.9k	↗
#4	KestrelElbow9092 Gay Straight Couple	Closet kicked in.	79.2k	679	3.6k	↗
#5	butchmax Straight Gay Couple	My Husbands Best Friend	119.9k	813	2.1k	↘
#6	wally4u Gay Couple Trans	Drunk Abs Experience I'll Never 4Get!	73.7k	330	2.0k	↘
#7	Dedavis Straight for Gay Straight	Super Bowl group event part six	102.6k	706	2.0k	↗
#8	sissyjamie4daddys Trans Couple Straight	I love water	84.7k	496	2.0k	↘
#9	Steve Straight for Gay Straight Gay	Doublelist fan	57.7k	677	1.8k	↘
#10	powers8 Gay Straight Straight for Gay	A fantasy come true	87.6k	678	1.7k	↘

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

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