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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 Visit Leads to Intimacy
So. I posted for cd/transgender. Shortly after waiting got a reply. Changed pics. She came over. Wow nice make up sexy body. Started making out. Next thing taking her panties off. She pushed my head

Posted by a straight man

By Anonymous

A Quick Connection from a Local Ad
Saw an ad for a CD that was local to me. Hit her up and got a reply about 2 minutes later filled with sexy pics and vids of her in sexy lingerie and with other guys. Went to her place and she told me

Posted by a straight man

By Anonymous

A Surprising Encounter at the Motel
I am a semi passable CD/do Drag. I've met plenty of men on craigslist in the past, some good some not so good. Last week I posted an ad on doubleslist and received several responses. Filtering

Posted by a TS / CD

By Anonymous

A Morning Coffee with Unexpected Guests
I am a older CD, who has had many lovers! Being bisexual is the best of both worlds, I can be all feminine for my man and be a man for my girl! I have very feminine body, with soft smooth model legs!

Posted by a TS / CD

By Anonymous

An Unexpected Encounter at His Home
I am not a full CD, but rather a pantyboy who loves wearing thigh high stockings, thong, hooker-type shoes, nipple clamps and some eyeshadow and lipstick with earrings. I placed and ad and went to

Posted by a TS / CD

By Anonymous

An Unexpected Encounter in a Truck
I'm a 28 yo Sissy gurl who posts on here, one night I had an reply from an older daddy type who wanted to meet up so I could suck him off in his truck. I got dressed and he picked me up drove to

Posted by a TS / CD

By Anonymous

A Unique Encounter Through an Online Ad
I am not a full time or passable crossdresser, but have some things to wear link satin lingerie and breast form tits. It's a big pair of breast form tits that have straps so they can be worn

Posted by a TS / CD

By Anonymous

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

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
I knew I was in for a rough time 63.8k 881 4.5k ↗
#2
Tiffanyheels
Couple Straight Gay
Most women have licked vagina 148.3k 2.1k 4.1k ↘
#3
kimorafoxxsexycd
Gay Trans Couple
Had a group experience 135.3k 1.5k 3.6k ↗
#4
cnysub
Straight Gay Trans
Alternative Position with Lesbians 82.2k 715 3.4k ↗
#5
KestrelElbow9092
Straight Gay Couple
Immediate Fantasy Fulfillment 51.7k 527 3.3k ↗
#6
sissyjamie4daddys
Trans Couple Straight
I love water 74.7k 490 2.0k ↘
#7
wally4u
Gay Couple Trans
I Guess He Did Have To Go! 69.4k 316 2.0k ↘
#8
butchmax
Straight Straight for Gay Gay
You Just Never Know 95.6k 650 1.8k ↘
#9
Steve
Straight for Gay Straight Gay
Gym kiss pt.2 54.3k 647 1.7k ↗
#10
powers8
Gay Straight Straight for Gay
A fantasy come true 84.7k 674 1.7k ↘
Page 1 of 50 · Showing 1–10 of 500 authors

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