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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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Rediscovering Past Desires and Relationships

Met a man on Doublelist and started to exchange turn-ons, fantasies and creative erotic scenarios. I have always been on the down low, very average guy, into guy types of things. In my past I had

Posted by a TS / CD

0

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A Night of Connection in a Hotel Room

I had finally and more importantly decided that I wanted to get fucked. As a long time non passable cross dresser I had progressed into going all the way. For years I would dress as I traveled for

Posted by a TS / CD

27

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A Serendipitous Encounter in the Lounge

The lights in the lounge were low, all warm amber and shadows. When she walked in, every conversation around you faded a little. Her presence wasn’t loud—just confident, silky, the kind

Posted by a TS / CD

By Charlotte555

0

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Seeking Adventurous Connections for Memorable Experiences

seeking adventurous and open-minded individuals for some adult fun! Let's meet up, let loose, and explore our naughty side together. If you're up for a good time and can handle a little

Posted by a TS / CD

7

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A Journey of Self-Discovery at a Hotel

I have been secretly dressing as a woman for years. To keep my anonymity, about once a month I travel 200 miles from home to indulge my fantasies at a hotel in a nearby city. The hotel is right next

Posted by a TS / CD

3

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Unexpected Visitors on a Snowy Day

We got bout 4" of snow here today. Bout 3-330 it stopped. I was just relaxing on the couch when I heard someone knock at the front door. I saw 2 younger studs, bout early 20s, standing there. I

Posted by a TS / CD

By sissyjamie4daddys

9

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An Unexpected Ride Home from the Party

This is the story of how I became a sissy. About ten years ago I was working second shift. On a Saturday when I was working we, my wife and I, were supposed to go to a party. All good, I drove her

Posted by a TS / CD

By sissy_hubby33

12

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A Day of Unexpected Encounters on Black Friday

Another wonderful black Friday has cummed n went, n this sissy gurl is sore n raw, but feels great! My jaws hurt n my sissy cunt is raw from the 13-17 BBBCs I had yesterday! Hell I'm still

Posted by a TS / CD

By sissyjamie4daddys

4

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A Night of Friendship and Unexpected Encounters

One night a female freind on mine knew I was into wearing lingerie decided to dress me you in lace panties nice red bra a dress. And wanted to watch me play so we posted a add didn't take long

Posted by a TS / CD

24

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A Chance Meeting at the Mall

so I was out at the mall the other day and did some shopping got a couple of cute outfits and a pair of heels i had noticed my butt plug and my dildo on my bag i quickly got my wallet out and paid

Posted by a TS / CD

33

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Unexpected Connection at a Rooftop Party

Yes! Spilling one that makes me 😈 just thinking about it a years Was at this dimly lit rooftop party in Brooklyn last summer, wearing a tight black mini dress, thigh-high boots, feeling myself

Posted by a TS / CD

17

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An Unexpected Encounter at the Park

I was answering some ads on doublist when this Daddy Dom contacted me. We met at the park, and I immediately dropped to my knees and pulled up my skirt, exposing my tight shaved boi pussy to him. He

Posted by a TS / CD

By Deleted User

13

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An Unexpected Day at the Park

Im an older married cocksucker with a conversion van I found that I like to wear panties stocking bras etc And when I do i become a slut I go cruising to parks and truckstops and smile and wave

Posted by a TS / CD

8

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An Exciting First Encounter at Her Apartment

I was laying in bed and very horny. I had always thought about how exciting it would be to make love to a TS. I was browsing around and came across the perfect black girl for me. I finally got up the

Posted by a TS / CD

By sambrown196802

8

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A Weekend Outing with Charming Company

Another fantabulous weekend for this lil sissy slut. I had a date with a VERY fine older daddy mans Friday night. Daddy mans treated me like a queen. Daddy mans took me spending(shopping) for new

Posted by a TS / CD

By sissyjamie4daddys

6

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An Unexpected Connection in Des Moines

was feeling in the mood for a little sex so got on here in the desmoines iowa part and was looking thru the adds. came across one that caught my attention. was a older man that had a prostrate

Posted by a TS / CD

By samantha1965

5

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A Playful Evening of Dressing Up and Surprises

You could! So as I put a pair of her panties on I said you can fit in these! He found a pair that fit while I dressed in a little skirt with nylons sexy bra and blouse. When he finally saw me he said

Posted by a TS / CD

By curiosity899

8

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A Surprise Visit from My Neighbor

This black neighbor that knows I cross dress and who I had sex with text me this morning kimora I'm hard as fuck and need you. So I quickly got cute wig and my makeup on wearing a sexy little

Posted by a TS / CD

By kimorafoxxsexycd

4

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Embracing Transformation and Confidence Together

. Trans, gorgeous, well trained transgender girl and friendly and very good at what I love to do and ready to steal the spotlight, Catch me if you can — one look and you’re hooked. Hot

Posted by a TS / CD

4

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An Unexpected Gathering with Friends

Another group sexssion in the books for this lil sissy slut n I feel REALLY good. I had the honor n privilege of providing my 2 fuckholes to 7 daddy mens n let me tell you sweetie, I was stuffed n

Posted by a TS / CD

By sissyjamie4daddys

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

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” A almitaaa “They found my clothes”

Rank	Author · Category	Latest Story	Views	Listens	Upvotes	Trend
#1	derake14 Gay Straight for Gay Straight	Parking lot kiss	34.3k	628	4.1k	↘
#2	Tiffanyheels Trans Couple Straight	Crossdressing intimacy in office	77.0k	1.4k	3.2k	↘
#3	KestrelElbow9092 Straight for Gay Gay Straight	Beautiful and Black	23.4k	353	3.1k	↘
#4	cnysub Gay Trans Straight	Ads on DoubleList	46.8k	523	2.9k	↘
#5	kimorafoxxsexycd Gay Couple Trans	Very kinky self care	72.9k	1.0k	2.7k	↗
#6	sissyjamie4daddys Trans Couple Straight	Sucking appendage in the club	44.3k	456	1.9k	↘
#7	wally4u Gay Trans Straight for Gay	My Birthday Suprise!	50.9k	272	1.8k	↘
#8	Steve Straight for Gay Straight Gay	Gym kiss pt.2	48.7k	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	32.4k	318	1.1k	↘

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

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