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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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A Night to Remember at the Hotel
I came to O***** for the night. got a hotel room, got dressed im my white garters and red nylons,, 6 in heels..looked pretty sexy with my teddy for 62 yrs old. Put add up and my picture, lot of

Posted by a TS / CD

By Anonymous

A Night Out Leads to Unexpected Connection
So I only like fems and trans. Well I met this sexy transgirl on here one night coming from the bar and she is probably the sexiest trans girl I've ever seen. We exchanged details and I went to

Posted by a straight man

By Anonymous

An Awkward Encounter with a Coworker
Ok so I’m a closet sissy and usually wear panties underneath my normal clothes when I go out. I put an ad on here and someone replied and it was actually my coworker (we work at a grocery

Posted by a gay man

By Anonymous

An Unexpected Encounter with a Brazilian Beauty
I met up with a sexy Brazilian TS. She was feminine and had great boobs. We started making out and after a few minutes she pushed my head downed pulled her dress up and pulled her nice cock out of

Posted by a straight man

By Anonymous

An Unexpected Encounter in a Nightie
I answered an ad for a man who was interested in a more feminine man. He wanted to suck a man for the first time. I figured a CD was more feminine so I answered the ad. He lived close by and was

Posted by a TS / CD

By Anonymous

A Nervous Encounter in a Hotel Room
I had been talking with someone on here after I posted my ad and was really nervous to meet up. I was fully dressed in my super short mini summer dress and was feeling cute! I walked to his hotel

Posted by a TS / CD

By Anonymous

A Midnight Encounter Before Easter
I am 27 year old top who enjoys feminine and passable cd bottoms. I have met a few cds in this lovely site. My last cd, was extremely sexy and feminine. I actually fucked her last night as my

Posted by a straight man

By Anonymous

A Late Night Adventure in a Hotel Room
I put up an ad as a semi passable crosssressed , being in my early 20s , on the petite side and Latina. I didnt want to go all the way and asked for someone with clothes since I live with parents

Posted by a TS / CD

By Anonymous

A Day of Fun with New Friends
About a month ago I met two mature CDs through DL. We finally managed to meet on a Saturday for some fun......we were all a little nervous at first, but after some kissing, our inhibitions melted

Posted by a TS / CD

By Anonymous

An Unexpected Visit from New Friends
I had three cds from doublelist come over and give me some one and done head. One forgot his dress up stuff but I provided him with some of mine. He had naturally long hair down to his shoulders.

Posted by a straight man

By Anonymous

An Unexpected Car Date Adventure
I'm a CD that dresses up when gf and daughter r asleep. Omg, I met this guy, and he made me feel sooooo slutty, and our car date turned out to lead to his apt, and oooooh, omg, he made me want

Posted by a TS / CD

By Anonymous

A Unique Encounter in a Gated Community
I hit up an ad for a TS that was looking for fun. I’m straight and this was my first encounter like this. I went over and was given instructions to come up to their floor in a gated condo

Posted by a straight man

By Anonymous

A Night of Unexpected Hotel Encounters
A few weeks ago I rented a hotel room, dressed up in my best lingerie and pulled a train with guys I met from doublelist, five in all. One was impotent, but the others fucked me hard and

Posted by a gay man

By Anonymous

An Unexpected Encounter at the Bar
I was at the bar getting tipsy when I felt the urge I hit up your gay for straight section wanting to try out a CD got an answer was a bit nervous. Showed up was invited in to a thick cd bbw had porn

Posted by a straight man

By Anonymous

A Mysterious Meeting with a New Friend
I met a very horny Asian cross dresser on here. She was wearing a mask. She asked for a picture of my cock. I sent a clean photo of my 7” dick to her. She said it was very hot and that I

Posted by a straight man

By Anonymous

A Sunny Park Meeting with a New Friend
I am a 50 year old bi male. I had been chatting with a crossdresser, M*****, I met through here, and we finally were able to hook up. It was finally a nice day out, warm, sunny. We made plans to

Posted by a gay man

By Anonymous

Finding Love Through an Online Connection
Well to be honest at the beginning I was afraid ..... But I take the chance and i post 3 pictures of me .... I receive like 3 or 4 response but no intrested....one day i recive a shemale e

Posted by a straight man

By Anonymous

An Unexpected Visit from a Crossdresser
I met this crossdresser from A****. She was unbelievably sexy! She drove down to M***** to my apartment to meet and have some adult playtime! For discretion purposes she arrived dressed normal. But

Posted by a straight man

By Anonymous

A Surprising Encounter with a Neighbor
One night I was feeling lonely having my GF living in another country and started searching online about shemales and cds just being curious, I found this ts and started chating with her, it turned

Posted by a straight man

By Anonymous

Exploring New Connections with a Bisexual Couple
I am bi married white male that loves to crossdress and orally service men in the video booths at the adult store . Where I go has video booths on two sides , about 30 in all , and a dark lounge/play

Posted by a straight man

By Anonymous

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 Straight
Parking lot kiss 33.8k 625 4.1k
#2
Tiffanyheels
Trans Couple Straight
Crossdressing intimacy in office 76.1k 1.4k 3.2k
#3
KestrelElbow9092
Straight for Gay Gay Straight
Beautiful and Black 23.0k 352 3.1k
#4
cnysub
Gay Trans Straight
Ads on DoubleList 45.4k 519 2.9k
#5
kimorafoxxsexycd
Gay Couple Trans
Very kinky self care 69.6k 1.0k 2.7k
#6
sissyjamie4daddys
Trans Couple Straight
Sucking appendage in the club 43.5k 456 1.9k
#7
wally4u
Gay Trans Straight for Gay
From Zorbas To His Hotel Room 50.0k 272 1.8k
#8
Steve
Straight for Gay Straight Gay
Gym kiss pt.2 47.4k 593 1.7k
#9
curiousladyd
Straight Couple Straight for Gay
First really big appendage 9.8k 356 1.2k
#10
Dedavis
Straight for Gay Straight
House hunting pt 1 37.8k 276 1.1k
Page 1 of 50 · Showing 110 of 500 authors

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