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Transgender Sex Stories – Real Encounters & Passionate Experiences

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Category: TS / CD

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A Unique Journey of Self-Discovery and Connection
I am a passable crossdresser. I love sexually pleasing top daddys n young virile studs. It don't matter to me if they are married or single, white, black, straight, bi or gay, if they are

Posted by a TS / CD

By sissyjamie4daddys

A Blindfolded Encounter with Unexpected Guests
So I've recently got into wearing sexy panties and thigh highs for older men who want a sissy slut bottom. I'm 37, men in their 50s and 60s turn me on. I responded to a post looking for a

Posted by a TS / CD

By mball70220

A Night of Transformation and Connection
BOB TURNS INTO ROBERTA PART 2.....I started working my cock in and out and he told me I was making him feel so feminine, he said he loved to get fucked. I guess I lasted about 15 minutes before I

Posted by a TS / CD

By radioman666

A Memorable Hotel Visit with Daddy
It's Cocktober, the month to get as much cock in 31 days as possible. It's the month that daddy's rock out with their cock out. Yummy! I am a nut slut who simply LOVES pleasing top

Posted by a TS / CD

By sissyjamie4daddys

Finding Connection After a Work Injury
I'm a non passable crossdresser. I don't do the wig thingy, or makeup. I do wear slutty clothes under my manly clothes I am a total bottom sissy when I am in my fem clothes. I am bisexual

Posted by a TS / CD

By sissyjamie4daddys

A Surprising Meeting at the Adult Store
Hi it's me again here to tell my story of loving the adult store again I go there of course for cock there today was a black guy with this huge cock at least 9" and very thick I

Posted by a TS / CD

By Deleted User

A Night of Hypnosis at the Gay Bar
So I met a guy here on dl we chatted for weeks he said he was a Doctor and hypnotist and a very kinky dominant man sexually I told him I was a bi submissive bottom guy I told him my darkest fantasies

Posted by a TS / CD

By bslave101

A Night of Surprises at the Gay Bar
So I met a guy here on dl we chatted for weeks he said he was a Doctor and hypnotist and a very kinky dominant man sexually I told him I was a bi submissive bottom guy I told him my darkest fantasies

Posted by a TS / CD

By bslave101

Exploring Public Encounters and Addictions
I am addicted to men. When I am out in public, I don't look at faces. I look to see if they have a nice bulge, a growing tent, any cock movements. I am a cock n cum addicted whore. Plain n

Posted by a TS / CD

By sissyjamie4daddys

A Nervous Encounter: First Time at Home
I was looking at ads on DL a a few days ago n 1 of em caught my attention. It was from a young black stud who was looking for a TS or passable crossdresser to fuck for his 1st time. I replied to his

Posted by a TS / CD

By sissyjamie4daddys

Embracing My True Self: A Journey of Transformation
After 2 failed marriages to woman I transitioned to the female side. I have been trans now for 6 months and I am loving my new life. Most of my fam and circle of friends are open minded, and have

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Hotel Meeting with a Couple
I am strictly dickly. I am 100% gay, a sissy, a crossdressing bottom gurl. I haven't had sex with a woman in years. So I was caught off guard a lil when I got a reply from a m/f couple asking if

Posted by a TS / CD

By sissyjamie4daddys

A Chance Encounter at the Casino
So how was everyone's weekend? I had a fab weekend once again. A sugar daddy who loves bout 6 hours away called me n told me he was going to be in town n wanted to spend some time with me. Daddy

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Evening with Friends and Family
One of my daddy's stopped by Saturday evening with a friend of his. Daddy is a sexy silver haired fuck machine in his early 70s n with the help of a lil blue pill, can fuck for hours. His friend

Posted by a TS / CD

By sissyjamie4daddys

A Surprising Connection Found Through Online Ads
I was looking thru ads on DL n AFF. Saw an ad from a young black stud who was looking for a sissy gurl, so of course I replied. Holy fuck! He sent me a pic of his BBBC, n it was huge!! At least

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Visit from Daddy on a Thursday
I was sitting at home on a lazy Thursday morning, just doing some housework. Bout 1030, there was a knock at my front door. I wasn't expecting any visitors. I opened the door n there stood 1 of

Posted by a TS / CD

By sissyjamie4daddys

A Night Out: Seeking Attention and Connection
I love n enjoy being the center of attention. I am an attention seeking whore. I love the attention I get from men while out at a bar, restaurant, store, the mall, anyplace I am in public or private

Posted by a TS / CD

By sissyjamie4daddys

A Day of Pampering with My Sugar Daddy
I am a very lucky gurl. A sugar daddy took me $hopping n $pending Friday, n sugar daddy pampered me like the lil prissy sissy I am. My sugar daddy surprised me by texting me Wednesday morn to tell me

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Visit to a Local Shop
I got dressed n decided to visit a local porn shop this morning. I had on my tight blue/black dress that hugs my body, stockings n a pair of black 4" cfm heels. I had my dark wig n makeup on. I

Posted by a TS / CD

By sissyjamie4daddys

An Intriguing Home Visit Adventure
The second time i went for a date with a BLACK DOM DADDY it was a home visit at his house. I arrived on time at 800 pm and as instructed prior I walked to the door put on the blindfold then knocked

Posted by a TS / CD

By Deleted User

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
Straight for Gay Couple Straight
I couldnt refuse the temptation. 49.7k 738 4.3k
#2
Tiffanyheels
Straight Couple Trans
Finally had intimacy with ex mother in law 100.6k 1.7k 3.4k
#3
KestrelElbow9092
Straight Gay Straight for Gay
A chance meeting. 36.1k 429 3.2k
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kimorafoxxsexycd
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Bf was a sweetheart today 102.0k 1.2k 3.1k
#5
cnysub
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My boyfriend/ Master/partner 61.2k 618 3.0k
#6
sissyjamie4daddys
Trans Couple Straight
I love water 60.9k 470 1.9k
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wally4u
Gay Trans Straight for Gay
My Night At The Anvil... Part 1 58.1k 279 1.8k
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Steve
Straight for Gay Straight Gay
Gym kiss pt.2 51.9k 630 1.7k
#9
powers8
Straight Straight for Gay Gay
My greatest vacation ever 52.0k 482 1.3k
#10
butchmax
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My Wife Got Sick 59.8k 472 1.3k
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