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Transgender Sex Stories – Real Encounters & Passionate Experiences

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Category: TS / CD

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Discovering Identity and Friendship at MegloMart
Part 2 of my trip to MegloMart, I met two older gay men, one a guy the other a crossdreser. They really helped me become Marcia a sexy slut crossdresser so much so I'm becoming a transsexual, my

Posted by a TS / CD

By cnysub

A Weekend Escape to a Secluded Cabin
A local sugar daddy invited me to his cabin in the woods by a lake. He has about 50 acres that is private and secluded in the middle of nowhere MO. He told me it would just be the 2 of us, fishing,

Posted by a TS / CD

By sissyjamie4daddys

Unexpected Encounters on the Couch
Sitting on the couch with a fuckbuddy stroking his cock, as my daughter in law rubs her cunt and watches. My fuckbuddy asked me if he could fuck her. "Of course you can" I tell him.

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Shopping Trip with New Friends
I went to MegloMart early this morning, I'm a crossdresser 28,5 ft. 6 inches tall, 152 lbs. I need some thigh high stockings and panties. As I was looking at the panties 2 older guys walked by,

Posted by a TS / CD

By cnysub

Embracing My Journey as a Submissive Woman
I am a complete bottom sissy bitch for all top.men. I am a guaranteed piece of ass. I have been fucked by thousands of men over the past 10-12 years. I can be submissive at times. I love pleasing top

Posted by a TS / CD

By sissyjamie4daddys

A Surprise Visit from Daddy Tim
Part 3 Tim and Bill The next day daddy Tim, as I was told to call him, texted me and told me he was stopping by after work. He told me to make sure I was fully dressed and ready for him. I showered,

Posted by a TS / CD

By sissyjamie4daddys

Unexpected Connections Among Prison Friends
Im a 50 yo non passable masculine cd now but before last year ive always been a total masculine bottom since my first cock at 16 yo.. Alpha in public, work, family and friends. No one would ever

Posted by a TS / CD

By Longterm

Exploring the Unique Landlord-Tenant Connection
It's been a while since I posted any stories or encounters. I am a sissy bottom who is a very passable crossdresser. I wear fem clothes, wigs, makeup, and have 38 DD titties 24/7/365. I love my

Posted by a TS / CD

By sissyjamie4daddys

A Surprise Encounter with the Delivery Guy
Just another typical morning for this lil sissy gurl. I woke up horny as fuck!! I was watching some tranny porn on my big screen TV, rubbing my lil ppclit, with my toys out. I got on DL to find me

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Delivery Leads to a Surprise Meeting
Just another typical morning for this lil sissy gurl. I woke up horny as fuck!! I was watching some tranny porn on my big screen TV, rubbing my lil ppclit, with my toys out. I got on DL to find me

Posted by a TS / CD

By sissyjamie4daddys

A Surprising Morning with a Flower Delivery
Just another typical morning for this lil sissy gurl. I woke up horny as fuck!! I was watching some tranny porn on my big screen TV, rubbing my lil ppclit, with my toys out. I got on DL to find me

Posted by a TS / CD

By sissyjamie4daddys

A Journey of Self-Discovery After Divorce
I crave cock 24/7. It's been this way every since I divorced my wife 8 years ago. See, she was a slut who was always fucking other men. I was not jelly of the men she fucked. On the contrary. I

Posted by a TS / CD

By sissyjamie4daddys

Finding Confidence in a Parking Lot Adventure
I go by Erica. I’m a native CD. I’m moved to Albuquerque recently. I started cross dressing a few years ago. At first I was scared to go out in public dressed. So I would dress in my

Posted by a TS / CD

By Erica

An Unexpected Night with Friends
Part II Tim n Bill After a few minutes of me sucking Bill's cock while Tim rubbed his cock on my ass the 3 of us went into my bedroom. I got on all 4s as I continued sucking Bill's cock.

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Encounter in the Bathroom
I have always been attracted to women, not men, and have enjoyed a voluminous sex life since my teen years. When i could not be with a woman i would find an Xrated video booth and jerk off to

Posted by a TS / CD

By geewiz2023

A Night of Surprises on Date Night Part 2
"Last night was date night part 2" of 2 She takes a dab of lube i didnt see it and wipes her finger off on my butt hole, no fingering me or no rubbing it in or anything like that to get it

Posted by a TS / CD

By rachelbottomcd

An Unexpected Encounter in the Park
I love public sex. I love sucking cock and getting my lil ass fucked in public. It's such a major turn on for me. Yesterday, I went for a walk at a small local park. I was wearing a tight lil

Posted by a TS / CD

By sissyjamie4daddys

A Night of Surprises at the Theater
Hello ,I post here regularly but lately I've been quite.Any way let me share this with you...Was getting very horny so I decided to dress fully n head to the Fairmount theater in New Haven .I

Posted by a TS / CD

By nykmaleforu

Exploring New Dynamics on Date Night
"Last night was date night again part 1" For this 55 yo chubby bottom daddy and his BBC FwB Trans MtF top. I am Sub and a pain slut and Mommy is dom and luv to spank me. We always chat for

Posted by a TS / CD

By rachelbottomcd

A Surprising Meeting at the Bookstore
I stopped at my local adult bookstore yesterday. I was looking at buying a new dilly or vibrator. As I was looking an older man started talking with me. "What you looking for sweetie" he

Posted by a TS / CD

By sissyjamie4daddys

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
Couple Gay Straight for Gay
In our early days of playing. 69.5k 916 4.6k ↗
#2
Tiffanyheels
Couple Straight Gay
Multiple pleasures while swinging 159.7k 2.3k 4.2k ↘
#3
kimorafoxxsexycd
Trans Gay Couple
My first adult bookstore fun 139.8k 1.5k 3.7k ↘
#4
cnysub
Trans Couple Straight
mY new submissive transgender 86.3k 727 3.4k ↘
#5
KestrelElbow9092
Straight Gay Couple
A brief encounter 59.9k 590 3.4k ↗
#6
sissyjamie4daddys
Trans Couple Straight
I love water 77.9k 491 2.0k ↗
#7
wally4u
Gay Couple Trans
Missed The Fine Print! BIG TIME! 71.0k 317 2.0k ↘
#8
butchmax
Couple Straight Straight for Gay
I guess I told her while I was drunk 99.2k 662 1.9k ↘
#9
Dedavis
Straight for Gay Straight
Caught my neighbor part one 90.8k 663 1.8k ↗
#10
Steve
Straight for Gay Straight Gay
Gym kiss pt.2 54.8k 659 1.7k ↗
Page 1 of 50 · Showing 1–10 of 500 authors

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