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Transgender Sex Stories – Real Encounters & Passionate Experiences

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Category: TS / CD

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A Married Man's Secret Encounters

I'm a married bi guy, 26, I love wearing my wife's panties, bra, and dresses when she isn't home. I met my FWB on here, he comes over and I answer the door dressed up. He always grabs me and makes

Posted by a TS / CD

2

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An Adventurous Night at His House

I had received emails from a guy saying he had a 11 inch cock..we sent messages back and fourth for a little bit until I got the nerve to sneak out and be adventurous...I got to his house and went to

Posted by a straight man

By sexylingerie

2

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A Discreet Encounter with a Mysterious Stranger

I'm a married and discreet Male Latino. Most of the time when I'm home alone I love to dress. It's like having a feminine side and it's been a long time since I had sex with a man. The last man was a

Posted by a TS / CD

0

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An Unexpected Connection Leads to New Discoveries

Got home from a bar one night really horny. I looked on CL for a woman with no luck. Decided to answer an ad for a local guy who wanted to blow me while he wore panties. I had him come over and was I

Posted by a TS / CD

By likes big ones

1

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An Unexpected Encounter with the Delivery Driver

I ordered uber eats one time. I went downstairs in a short skirt with no panties ..my shmeat was hanging out. The driver kept looking at my phat ass as I tried to hind my print when answering the

Posted by a TS / CD

By jupiterstaraj

1

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Memorable Nights with Friends and Fun

I've always loved to be penetrated like a woman. I would put on my sexy satin and lace teddy with my white thigh-high lace top stockings and wait on the bed with my ass in the air and my head in the

Posted by a TS / CD

By Deleted User

0

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A Journey into Crossdressing and Confidence

New to crossdressing, feel very feminine while dressing. Have purchased more items over the past year and finally got up the nerve to meet a guy. Never realized how many guys like CD's! My GF

Posted by a TS / CD

2

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An Unexpected Adventure on the Wild Side

So I post for a woman for some fun with an acceptable pic of my body. I get a hit from a TS that says he/she liked my body and would I like to take a ride on the Wild Side! I figure, What the Hell,

Posted by a TS / CD

2

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An Unexpected Visit Leads to Intimacy

After a few months of chatting with str8 guy I finally had him over . I answered the door dressed sexy bra panties thigh highs wig makeup . We started out in my bathroom him sitting back against the

Posted by a TS / CD

By Deleted User

3

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An Unexpected Connection at Home

Responded to an ad from a TS looking to hook up. Got a phone number and made arrangements. Drove over to the house and she met at the door in lingerie, got naked and started getting my cock sucked.

Posted by a straight man

4

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An Unexpected Visit to the Local Shop

I'm 45 bi bottom CD I was feeling horny the other day so I picked out my favorite panties and skirt put my boobs on an went to the local sex shop when I went in I picked a booth an left my door

Posted by a TS / CD

By Deleted User

2

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An Unexpected Reunion and New Relationship Dynamics

I had a male we meet years ago. At first it was just me sucking him off. Over time I started letting him fuck me. I had started crisscrossing. I never told him. One day I sent him a picture of me

Posted by a TS / CD

By OlderMaleguy

3

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An Unexpected Motel Meeting with a Mystery

I messaged a smoking hot cd on here in c***** said she was looking for tops and in a motel in s******** so we decided to meet up I go there knock on door she answers looking like a super hot milf

Posted by a straight man

0

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An Unexpected Visit from a Mysterious Stranger

Put an ad on double list ,a CD looking for TS. About an hour later I get two pics, face and cock she’s beautiful African American. Has to be a catch. No just likes chubby cross dressers. She

Posted by a gay man

By submissivebottom

1

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Unexpected Shower Encounter in Long Beach

I am a slim smooth crossdreser in the long beach area. I'm vers but When i bottom, I love to reach my max. So I look for hung. Lately, I've been into fisting. So I posted on DL. I straight

Posted by a TS / CD

By rileylewis38

0

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A Day of Unexpected Encounters with New Friends

I’m a married Bi guy, last week I met two different FTM’s just hours apart. I luckily get to see each of them occasionally but last Thursday I met the 1st one at their house and we fucked

Posted by a straight man

0

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Unexpected Connection at the Dog Park

So I’m a bi married guy and try to hook up with a guy at least once a month. I’m a top, but normally just into swapping head. I’d fantasize about t-girls, and have hooked up with a

Posted by a straight man

1

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A Surprise Visit in the City

I was traveling through the city with a big arch and was looking to play with a CD. I posted a pic of my wife's g-string and invited a CD to come wear it for me while I sucked off her ladystick. I

Posted by a straight man

By GibbonHedge8008

1

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A Nervous First Meeting in Austin

Been looking on here for a bit. Finally found a ad for GH by sexy TS in North austin area. Exchanged few emails and pics. Great body and nice firm ass. greed to meet up. Got to her place. Nice dark

Posted by a straight woman

0

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A Yogi's Unexpected Meeting with a Couple

I've talked to lots of different lovies on here, I'm from the south do yoga and arts, I have a girly figure I always dress. I do gardening so it's no problem weeding the garden to find

Posted by a TS / CD

0

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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

D dorishannah “Teasing my neighbor.” S stumptroy “had no idea” P pleasure_town “How I found a new taste” L luciecar “Don’t want it to be a boring night”

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	64.0k	882	4.5k	↗
#2	Tiffanyheels Couple Straight Gay	Most women have licked vagina	148.6k	2.1k	4.1k	↘
#3	kimorafoxxsexycd Gay Trans Couple	Had a group experience	135.5k	1.5k	3.6k	↗
#4	cnysub Straight Gay Trans	Alternative Position with Lesbians	82.3k	715	3.4k	↗
#5	KestrelElbow9092 Straight Gay Couple	Immediate Fantasy Fulfillment	51.9k	527	3.3k	↗
#6	sissyjamie4daddys Trans Couple Straight	I love water	74.8k	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	95.7k	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	84.8k	674	1.7k	↘

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

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