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Category: TS / CD

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An Unexpected Reunion with My Ex-Wife

I responded to an ad from a younger stud who was looking for a bottom sissy. He was in his early 40s with a very nice delish looking cock. He invited me over n I immediately went to town sucking his

Posted by a TS / CD

By sissyjamie4daddys

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A Surprising Encounter in the Office Bathroom

So I'm in the closet right. But I wear panties and thongs all the time under my clothes. I don't know how but my coworker knows and came up in the bathroom as I was peeing, standing up and

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By Deleted User

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Unexpected Revelations in a Complicated Relationship

I remember the first time I put my sister's panties on I was young I loved how they felt I was already getting fucked like a girl from my brother with his huge cock I buried that when I met my

Posted by a TS / CD

By daviddickson

0

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Exploring Identity Through Baltimore Ads

I’ve been a sissy panty wearer since I can remember. In 82 or 83 I finally got up the nerve to go to an abs and accept an invitation for car play. Basically uneventful. In 85 I learned about

Posted by a TS / CD

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A Surprising Meeting at the Motel

I posted an ad as usual knowing that no one would be serious. I went to the motel and fucked my ass with the dildo. I received a response from a man who said he had a BBC and was going to abuse me.

Posted by a TS / CD

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A Unique Encounter in a Wrestling Ring

I love me some older kinky top men. I responded to an ad that said he was looking for a CD to wrestle around with in a wrestling ring. I got to his place n he had on wrestling trunks n he had turned

Posted by a TS / CD

By sissyjamie4daddys

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An Unexpected Night at the Group Party

Another weekend has cum n gone, just like the daddys I had the honor of pleasuring. I was invited to a lil group party Friday eve. There were 7 others at this lil party, 6 tops n 1 other gurl like

Posted by a TS / CD

By sissyjamie4daddys

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An Unexpected Encounter in the Bedroom

So I met up with a top n his lil twink bottom. Twink is early 20s, nice juicy bubble booty, n a nice thin cock bout 6 inches. Twinks daddy was a fine ass man! In his mid 50s, 6ft 3, 250 pounds with a

Posted by a TS / CD

By sissyjamie4daddys

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An Unexpected Game Night with Friends

I stopped by a daddys house the other night for game night: poker, pool, chess, ping pong, n other games. When I got to daddys house, there were 7 other men there all sitting around shirtless. I was

Posted by a TS / CD

By sissyjamie4daddys

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A Weekend Gathering at Daddy's Place

One of my suga daddys invited me to his place for a weekend party. Daddy lives in Louisville, which is bout 4 hours from me. Daddy sent me some gas money to cover my trip to n fro. I left my place on

Posted by a TS / CD

By sissyjamie4daddys

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A Journey of Self-Discovery and Connection

I was involved sexually with an older daddy for 7 months back in 2018. Daddy introduced me to daddy's friends, other daddys, doublelist, n other gay hookup sites. When I first met my Daddy I was

Posted by a TS / CD

By sissyjamie4daddys

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A Journey of Discovery and Connection

I had always been a very open minded hetero man very into assplay and I had decided to "branch out" in my sexual journey. After connecting with another man on DL we met at his place and

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An Unexpected Casino Encounter with a New Friend

I'm an older CD. I love dressing as a woman. I made my monthly overnight stay at casino not too far away from me. I usually fully dress as a woman. I posted an ad on Doublelist to see how many

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By OlderMaleguy

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A Stylish Stroll Through Manhattan's Streets

So…first of all l would like to introduce myself. My name is Mikhailla and I’m a dirty little piss whore. I am a slim, tall and sexy little piece of shit and I get so hot for older fat

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By Deleted User

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A Night of Unexpected Connections at a Party

I shared my wife with my boss when we were in our early twenties. He was about 34 and married but his wife wasn’t with him for a few months. We went to a party (He drove his van and picked my

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By Anonymous

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Exploring Freedom After Divorce

My ex wife n I dabbled in the swingers lifestyle for a few months before we got married. We went to a few parties where our rule was I could watch, but not touch. I would watch her with other men.

Posted by a TS / CD

By sissyjamie4daddys

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Unexpected Connections at the Casino Poker Table

Hubs n I went on a mini vacay a few weeks ago to Mississippi to visit a casino. For those that don't know, hubs is in his mid 70s, is completely useless n worthless in bed, but is financially

Posted by a TS / CD

By sissyjamie4daddys

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An Unexpected Encounter in a Motel Room

I have always loved dressing. When I dress I’m very sexy. Growing up I had to hide this. When I came out to my sister and her husband my sister was ok with me being gay but her husband said it

Posted by a TS / CD

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A Shy Encounter with an Older Gentleman

I posted an ad awhile back looking for an older daddy type looking for a gloryhole situation as I'm shy and semi passable. But very hot even dressed. I got ready, got a little buzz and got a few

Posted by a TS / CD

By Anonymous

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Adventures in an Adult Bookstore Setting

I went to an adult bookstore with glory-holes while fully dressed. In the glory-hole area, there were three floors of glory-holes and rooms that were private or semi-private. I walked between

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By Anonymous

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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

L luciecar “Don’t want it to be a boring night” R roosterrogers “Young eager for hours” J jabby69 “It took 20 years.....” S submit2one “Too Many Tops Think Anal and Intimate Technique is One in the Same”

Rank	Author · Category	Latest Story	Views	Listens	Upvotes	Trend
#1	derake14 Gay Straight for Gay Couple	The fast and furious	60.8k	857	4.4k	↘
#2	Tiffanyheels Gay Couple Straight	I guess I am getting to be gay	138.3k	2.0k	4.0k	↘
#3	kimorafoxxsexycd Gay Trans Couple	Swallowed my bfs meal at lunch	129.6k	1.4k	3.5k	↘
#4	cnysub Gay Trans Straight	Part 1 Nude Performer	76.5k	703	3.3k	↗
#5	KestrelElbow9092 Straight Gay Couple	Picnic Fun	49.0k	520	3.3k	↘
#6	sissyjamie4daddys Trans Couple Straight	I love water	72.1k	487	2.0k	↗
#7	wally4u Couple Trans Gay	Got Wife Off Flying To Cabo!	67.4k	309	1.9k	↘
#8	Steve Straight for Gay Straight Gay	Gym kiss pt.2	53.7k	644	1.7k	↗
#9	butchmax Couple Gay Straight	Marriage did it	87.4k	627	1.7k	↘
#10	powers8 Gay Straight Straight for Gay	A fantasy come true	83.4k	670	1.7k	↘

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