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Transgender Sex Stories – Real Encounters & Passionate Experiences

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An Unexpected Encounter During a House Tour
So i was cruising DL one day looking for a top. I really needed some strange cock immediately. I see an ad that caught my eye. 2 tops looking for sissy bottom. Hey, thats me!! Love my top

Posted by a TS / CD

By Deleted User

A Halloween Costume Adventure at the Mall
So today is October 31st, Halloween!! my favorite holiday, why you ask its because I get to parade around in a sexy costume and no one can say a damn thing. So if you don't know how I look im a

Posted by a TS / CD

By ThiccTrapQueen

A Weekend of New Connections and Fun
Part 2 23 year old CD. They took turns fucking her while I watched. Each one cum inside her pussy. When the last one pulled out, Meg said come here Amber. Lick my pussy clean. I got on my knees and

Posted by a TS / CD

By oldarmy

A Unique Coffee Date with a Couple
I'm 23, 5'11 about #150. Have mid length Black hair. Completely smooth all over. Totally passable when I dress. Perhaps to my advantage, I have a micro penis. When I'm completely

Posted by a TS / CD

By oldarmy

An Unexpected Visit Turns Into a Revelation
I want to thank my ex girlfriend for turning me into a cock loving, cum swallowing slut. It all started about 15 years ago. I was a normal straight 27 year old man who loved women. She was 22,

Posted by a TS / CD

By Deleted User

A Night Out at the Bookstore Adventure
I am a mature crossdresser. I dress head to toe and everything in between. I love the feel of lingerie on my ass, legs, thighs. Slipping my stockinged feet into 3 inch heels sends heat through my

Posted by a TS / CD

By donovan777

A Surprise Encounter During a Home Repair
I recently moved to a new city to be closer to my daddy. He paid for my move, set me up in a nice place. Daddy pays fir eveything. I am a passable crossdresser, with wigs, makeup, fake breasts, and

Posted by a TS / CD

By Deleted User

A Chance Meeting at the Hotel Bar
My fantasy. To be seduced by a CD. I’d be setting outside a hotel doing my reports. When a lady sets down next to me. Her legs are so sexy looking. I glance over and she is so hot. Nice

Posted by a straight man

By Deleted User

A Night of Transformation and Self-Discovery
Episode 1 Crossdresser's Night Out I am a mature, bi married male who loves to dress up in women's clothes. Not my wife's clothes though as I like to dress sexier than she ever does. I

Posted by a TS / CD

By donovan777

Adventures of a Crossdresser and His Lover
I am a semi passable crossdresser. Womans clothes: tight shorts, short mini skirts, short dresses, tight blouses, fake tits, 6 inch heels, stockings, wigs, makeup are my specialty. When im dressed i

Posted by a TS / CD

By Deleted User

Rediscovering Crossdressing and Old Connections
Well - now in my upper 40s I am getting back into crossdressing. I started 20 years ago but quit a couple years ago when my long-term boyfriend of 6 years moved out of state. I was crushed - I had

Posted by a TS / CD

By Deleted User

An Unexpected Encounter at a Country Mansion
I have been secretly crossdressing for about 5 years. I have been told i make a good looking gurl. I dont dress in public. But i do wear womans clothes under my pants and shirt. I work for A as a

Posted by a TS / CD

By Deleted User

An Unexpected Encounter on the Way Home
I am a mature petite passable feminine trans woman that lives 90% of the time as just that. I live the way I feel, a highly energized sexy milf. I get offers for dates from guys in their 20's.

Posted by a TS / CD

By Deleted User

An Unexpected Visit from the Neighbor
I'm 26, a BBW TS. I'm 5'7 #220 and have a nice 8 inch thick uncut cock, fully functional. 36C Breasts pierced. Several tattoos. Mid length Black hair. A very cute face. To my knowledge

Posted by a TS / CD

By oldarmy

An Unexpected Late Night Visit with Friends
There was a petite CD I was getting together with about once a month when my wife was working late. S/he like to suck me hard, then ride me for a while until S/he got hard. When I was about to cum

Posted by a straight man

By FerretUmber7968

A Chance Encounter in the Park at Night
So back in CL day I meant a str8 guy and we first started emailing and them decided to meet. First time I put on my maxi dress and heels he came over I pulled out his 10+ bbc deep throated the hell

Posted by a TS / CD

By Deleted User

A Surprising Connection at the Bar
I'm a mature crossdresser was out looking for a masculine older man. Been moving around the bar looking. Was getting late, sat down and had last drink of the night. Then I was surprised to have

Posted by a TS / CD

By danajames

An Adventurous Night While House Sitting
I was house sitting for a relative and felt a little adventurous, so decided to create an ad for myself. I don’t normally have intimate experiences, so this was my chance since I’d be

Posted by a TS / CD

By Deleted User

An Unexpected Connection with a Younger Man
I am a passable crossdresser. I am 100% bottom. I LOVE pleasing top daddys. I prefer older, more sophisticated men. I have a tendency to hook up with top daddys that are 55 yrs and older. (I am 48).

Posted by a TS / CD

By Deleted User

An Evening with Friends and a Sissy Submissive
I'm a 30 year old sissy CD, behind closed doors. I'm 5'11 220 light brown hair and smooth all over. Masculine acting at work. I've been serving a Dominant man for about six months

Posted by a TS / CD

By oldarmy

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 34.0k 625 4.1k
#2
Tiffanyheels
Trans Couple Straight
Crossdressing intimacy in office 76.4k 1.4k 3.2k
#3
KestrelElbow9092
Straight for Gay Gay Straight
Beautiful and Black 23.2k 353 3.1k
#4
cnysub
Gay Trans Straight
Ads on DoubleList 46.0k 521 2.9k
#5
kimorafoxxsexycd
Gay Couple Trans
Very kinky self care 71.2k 1.0k 2.7k
#6
sissyjamie4daddys
Trans Couple Straight
Sucking appendage in the club 43.7k 456 1.9k
#7
wally4u
Gay Trans Straight for Gay
From Zorbas To His Hotel Room 50.1k 272 1.8k
#8
Steve
Straight for Gay Straight Gay
Gym kiss pt.2 48.0k 604 1.7k
#9
curiousladyd
Straight Couple Straight for Gay
First really big appendage 9.9k 357 1.2k
#10
Dedavis
Straight for Gay Straight
House hunting pt 1 37.9k 276 1.1k
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