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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.

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An Unexpected Encounter with a Stranger
The other day I was walking my lil pupperz near my house. I noticed this car would pass by slowly, go around the block then circle back around. I didn't think much of it. Finally after about the

Posted by a TS / CD

By Deleted User

An Unusual Rent Collection Experience
It's that time of the month. Time to pay your rent. But this time I'm collecting 2 months rent. Be ready by 11. Thats the text my landlord sent me. Unlike most renters, I love paying my

Posted by a TS / CD

By Deleted User

A Morning Meal with My Sugar Daddy
I love older daddy types. IMO, older daddys are simple the best lovers, considerate, passionate, and know how to please a gurl like me. I have several sugar daddys that I "date" on a reg

Posted by a TS / CD

By Deleted User

A Married Woman's Journey of Exploration
I get asked a lot of questions about my lifestyle. 1. Are you married? Yes I am married to a much older man. Hubs is a worthless, useless, pathetic, poor excuse of a man. The ONLY reason I married

Posted by a TS / CD

By Deleted User

A Sibling's Unexpected Dress-Up Night
Part 2 as I left off with my brother rushing in n raming his cock in my mouth and I showing him how well I suck cock .....a cpl of weeks have pass n nothing was mention about me getting caught n me

Posted by a TS / CD

By nykmaleforu

Unexpected Encounters on a Myrtle Beach Getaway
Hubs and I took a lil vacay last week to myrtle beach. Hubs can't fly because of medical issues, so we always drive. We stayed over night in Virginia and I got the chance to taste the local

Posted by a TS / CD

By Deleted User

A Surprising Meeting at the Gas Station
Im a 50yo latina closet crossdresser. 6'2" 195lbs leggy and love to dress FULLY...wig, skirts, painted toes, nails, anklets, toe rings etc... Mostly love to do it in the privacy of my

Posted by a TS / CD

By frida13

An Unexpected Night of Drinks in Las Vegas
I live in Las Vegas I’m a white male 46 and this is about the time I had the best sex of my life with a sexy trans women. We would see each other at work functions. I thought she was different

Posted by a TS / CD

By vegasguy11

Exploring Connection in a Reflective Space
part3 I knealt down in front of him and took his hot hard cock into my mouth and ram my lips up and down the ridgid shaft running my tongue arund the head then lidking his balls and sucking them one

Posted by a TS / CD

By foxy157

An Unexpected Encounter in the Bathroom
part 2 He took my hand and led me into the bathroom. We wereboth naked and I could not stop looking at his cock, which I wanted in my mouth and inside me. He looked over and said not yet honey. As

Posted by a TS / CD

By foxy157

A Business Trip Leads to Unexpected Connections
I am a mature (60+) male who has always lived as a male and been with a woman. I had enjoyed sex woith a woman but I felt that there was more I wanted. I looked at crossdressing porn and it excited

Posted by a TS / CD

By foxy157

A Surprising Connection from an Online Ad
My story begins last fall. I like to dress when I can and I decided to post an ad on Doublelist. It was perfect. I chose a picture of my waist down in red bikini string panties and I had my toes

Posted by a TS / CD

By PantherCairn1122

An Unforgettable Stay at the Hospital
I spent the last 2 days in the hospital and let me tell you something: I enjoyed it!! The male doctors, male nurses, male orderlies, the male patients sure do know how to treat a gurl like me. I

Posted by a TS / CD

By Deleted User

A Night Out at the Kink Club
CrossDressing in the Kink Club Dressing in my slutty outfits was generally something I’d really done in private. Then one night, while attending a kink party I got really daring and decided to

Posted by a TS / CD

By emcee7769

A Surprising Mother-Son Fashion Journey
I had been trying on moms panties and dresses. I always put everything back back like they was I thought. But she must have suspected something because one day when I came in she pitched me a package

Posted by a TS / CD

By dickluvnsissy

A Night Out at the Adult Theater
My first gang bang I have been going out to the local Adult video store for an awhile but one night was special. I spent quite a bit of time getting ready . I took a long bath and shaved every Inch

Posted by a TS / CD

By Deleted User

Seeking Connection in Unconventional Ways
I'm a 36 year old white male I'm really into wearing women's clothes and being a sissy cocksucker. I would love to find a boyfriend and see where it goes I've been playing with

Posted by a TS / CD

By Kacie

An Unexpected Night at the Adult Theater
My first gang bang I have been going out to the local Adult video store for an awhile but one night was special. I spent quite a bit of time getting ready . I took a long bath and shaved every Inch

Posted by a TS / CD

By OcelotEmber2744

A Spontaneous Weekend Adventure on the Road
Not From Around Here It was a warm weekend, I had some amazing treats that put me in a very slutty, kinky, horny and explorative mood...yeah, I'm not staying in the house! So, I took a

Posted by a TS / CD

By prettyskynative

A Day in the Woods: An Unexpected Meeting
So made a post CD looking to play, got a few responses but the one that I responded to. Was this guy that had a house out on 10 wooded acres and super private and he loves to play outside during the

Posted by a TS / CD

By Kellieskirt

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
Gay Straight for Gay Couple
The fast and furious 60.2k 847 4.4k
#2
Tiffanyheels
Couple Straight Trans
Enthusiastic bi girlfriend wanted to be restrained at swingers club 134.8k 2.0k 3.9k
#3
kimorafoxxsexycd
Gay Trans Couple
Swallowed my bfs meal at lunch 128.4k 1.4k 3.5k
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KestrelElbow9092
Straight Gay Couple
Picnic Fun 48.6k 519 3.3k
#5
cnysub
Gay Trans Straight
Part 1 Nude Performer 75.7k 694 3.3k
#6
sissyjamie4daddys
Trans Couple Straight
I love water 71.7k 487 2.0k
#7
wally4u
Couple Trans Gay
Got Wife Off Flying To Cabo! 67.2k 309 1.9k
#8
Steve
Straight for Gay Straight Gay
Gym kiss pt.2 53.7k 644 1.7k
#9
butchmax
Couple Gay Straight
I Guess We Asked for it 84.3k 616 1.7k
#10
powers8
Gay Straight Straight for Gay
A fantasy come true 82.9k 668 1.7k
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