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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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Category: TS / CD

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An Unexpected Connection at the Gay Bar
I'm 25, very passable. I'm petite and stay smooth all over. I dressed up one Friday night to go out. A nice sexy short dress. Wig, make up. Sexy bra and bra and breast forms. Crotchless

Posted by a TS / CD

By oldarmy

A Discreet Encounter on the Couch
I'm bisexual, I never believed it until now. I've been for passed year desiring a man to top me. I'm bottom only. I would cross dress because I enjoy panties and I have thin smooth

Posted by a TS / CD

By Justme

Unexpected Meeting at the Park Restroom
Hello I am Debbie a semi passable crossdresser I put an ad on ad on DL the other night. Letting everyone know that I was going to Bicenntenial Park after I finished my paper route. I would be dressed

Posted by a TS / CD

By akadebbie

A Lingerie Adventure in an Adult Bookstore
I am 67 years old and have been wearing lingerie for about 27 years. About eight years ago I wore thigh highs, garter, panties under mens clothes and went to an adult bookstore with glory holes. I

Posted by a TS / CD

By pantiedguy

A Journey of Self-Discovery and Attraction
So I'm a straight Male. But for some reason I get turned on by trans porn. And it seem to be the lady boy / super feminine. I havent actually had encounter. I'm leaning very hard towards it

Posted by a straight man

By forevernasty

A Surprising Meeting at the Adult Store
This happened a long time ago but I think of it often. I got off work around 2 a.m. one day and on the way home decided to stop at a porn shop to watch some straight videos. I got some coins and went

Posted by a TS / CD

By likes big ones

An Unexpected Movie Night Reunion with Friends
Part 5 of 5. We had all kinds of fun that weekend then my best friend went back to school, but before he did his dad told us he didn't care if we fucked each other even when he isn't there.

Posted by a TS / CD

By khead1994

An Unexpected Birthday Surprise at Home
Part 4 of 5. So I ended up moving in with my best friends dad. As we would fuck he began dressing me up more and more he bought me wigs and make up and had me start hormone therapy. I began to dress

Posted by a TS / CD

By khead1994

An Unexpected Invitation After School
Part 3 of 5. Right as my friend and I finished getting him packed up and all his stuff in his car his dad got back home. We both said goodbye and my best friend left to go back to school. His dad

Posted by a TS / CD

By khead1994

An Unexpected Visit to a Best Friend's House
Part 2 of 5. So the next morning after my 21st and after getting fucked for the first time from my best friend's dad, I got up and went home to my apartment and showered then rested the rest of

Posted by a TS / CD

By khead1994

An Unexpected Meeting at the Super 8
Posted as a 21 m looking for a bottom. A CD hit me up really fast and told me to come to a super 8 right next to my house. I’m there within 15 min. She’s wearing a black bra, with a lacy

Posted by a straight man

By Deleted User

An Unexpected Surprise Visit from a Friend
Well back to the story so with my stepdaughter out of town for the weekend I have my TS lover spending the weekend with me we are having a great time together playing with each others body and

Posted by a straight man

By flalicker

A Surprising Reunion with a Family Member
I have multiple ads here n presently live now I posted as a total bottom n discreet Latino crossdresser I have been here for about a 2 years .Well one nite I was dress fully putting together another

Posted by a TS / CD

By nykmaleforu

An Unexpected Connection at the Store
Where to start. I am a 54 yr old sissy bottom who is a non-passable crossdresser. I have been crossdressing for the last 3 years. I wear mini skirts, dresses, stockings, daisy duke shorts, stockings,

Posted by a TS / CD

By Deleted User

A Unique Journey in Massage Therapy and Self-Expression
I have been a crossdresser since I was a teenager. I enjoy dressing when I can. I enjoy dressing sexy and a bit slurry. I am a massage therapist witb my own home based business. When business started

Posted by a TS / CD

By doubletrouble56

A Mysterious Late Night Encounter with Mistress
I am a submissive white male, I have played in the past many times with female Dommes and couples, TS, some time last year I saw an ad for a sub straight male in the Gay for straight section, I

Posted by a straight man

By Deleted User

An Unexpected Night at the Hotel Theater
I put an add out , stating mature crossdresser, simi passable. I get several responses and one decides to meet up at a hotel. After hours of sitting in the room waiting I realized it was a no show.

Posted by a TS / CD

By browneyeboi

An Unexpected Connection at the Motel
I first realized I love trans and CD threw porn and wanted a experience and found one on IG we got talking and the same week we met a motel she was a bbw huge dick and everything and she was a

Posted by a straight man

By bloodshot22

A Journey of Self-Discovery Through Fashion
First I want to say thanks for building this site, it's awesome. I'm in the closet and actually straight acting in public. I drive an 18 wheeler and have that type of demeanor. But at home

Posted by a TS / CD

By jstlooking2012

Exploring Bondage in a Long-Term Relationship
My wife is the most beautiful blonde with blue eyes, small tits with amazingly long nipples that drive me crazy, I love when she decides to go braless, it has to drive guys nuts when they see her.

Posted by a TS / CD

By britni

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 59.5k 840 4.4k
#2
Tiffanyheels
Couple Straight Trans
Girlfriend turned bi and craves females 131.6k 2.0k 3.9k
#3
kimorafoxxsexycd
Gay Trans Couple
Swallowed my bfs meal at lunch 127.0k 1.4k 3.5k
#4
KestrelElbow9092
Straight Gay Couple
Picnic Fun 48.4k 517 3.3k
#5
cnysub
Gay Trans Straight
Part 1 Nude Performer 74.7k 694 3.2k
#6
sissyjamie4daddys
Trans Couple Straight
I love water 71.3k 487 2.0k
#7
wally4u
Couple Trans Gay
Got Wife Off Flying To Cabo! 67.0k 308 1.9k
#8
Steve
Straight for Gay Straight Gay
Gym kiss pt.2 53.6k 644 1.7k
#9
powers8
Gay Straight Straight for Gay
A fantasy come true 82.6k 668 1.7k
#10
butchmax
Couple Gay Straight
I Guess We Asked for it 82.2k 615 1.7k
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