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An Unexpected Meeting at the Pond
My wife was gone so I started looking to see if anyone close by needed drained and wasn't long before I got a reply from a local guy who said he hadn't unloaded in a while. He told me that

Posted by a gay man

By creammouth

Unexpected Meeting with the Trash Collectors
my trash men have another route can u help me,i servced then in my garage on collection day, 2 older and one young black,in my garage as they drank my beer i sucked their cocks i tipped them nicely

Posted by a gay man

By softerlipps

Navigating Love and Openness in Relationships
Ok so I'm bi. Not completely gay. I had been married 3 other times. They always fell apart for one reason or another. But mostly because the sex stopped. And I would play with men and be

Posted by a gay man

By derake14

Unexpected Meeting in the Produce Aisle
I think the hottest sex with another man began in a place that wasn't normally a venue for gays to meet. While some guys cruise a library, sometimes you meet a prospective partner, like a drug

Posted by a gay man

By jamashza

Unexpected Reunion at a Neighbor's Storage Unit
40 years ago I had a neighbor I was friends with. I watched him rise his son. Over time we became close he turned me into his sissy sex slave. A month ago he passed away. I saw his son at the

Posted by a gay man

By plaything5

A Curious Encounter at the Neighborhood Bar
I was at a regular neighborhood bar that primarily catered to the working man's place to go, to have a few beers, shoot pool and throw darts. Nothing gay for the most part. While I was in the

Posted by a gay man

By jamashza

An Unexpected Encounter with a Couple
I responded to a DL ad from a couple who wanted to have a three-way. When I arrived at their house, I was greeted at the door by the female. She was smoking some 420 and handed me a bowl. As I was

Posted by a gay man

By jamashza

An Unexpected Encounter at Her Father's House
I live a very straight life. Not married, I do have a girlfriend. No one in my straight life has any clue about me enjoying a mans touch. Straight act makes it hard to meet a man I can discreetly

Posted by a gay man

By deepinsideme10

A Surprising Encounter at the Arcade on Christmas Eve
27 masc here got throat fucked by big salty daddy cock first time at arcade i was curious about checking out. All happened christmas eve i had some time to kill and passed by a sleazy and seedy

Posted by a gay man

By bubblebuttfuckin

An Unexpected Connection in a Hotel Room
Got text to come play off agay dating site so I went an when I got there he was waiting in her room as I walked in I dropped my pants the dude was very hàiry on body but bald he bent down an

Posted by a gay man

By schaedler

An Unexpected Connection at the Hotel
Got text to come play off agay dating site so I went an when I got there he was waiting in her room as I walked in I dropped my pants the dude was very hàiry on body but bald he bent down an

Posted by a gay man

By schaedler

An Unexpected Encounter at the Home Warehouse
When I'm out in public and come face to face with guys that are together, I like to be extremely cordial and polite. " How are you guys doing?" 99% of the time they respond with a

Posted by a gay man

By KestrelElbow9092

An Unexpected Encounter at a Party
Car week continued As my ass was being pounded I was grunting in pain. My hostess once again patted me on the head and said “ hey you, focus on my pussy” I turned my attention back to

Posted by a gay man

By biinsalinas

An Unexpected Visit Leads to a Memorable Night
I remember the first time I took a guy up my ass that had a large mushroom shaped head. I put some lube in my hand and started applying it to his cock, he got hard quickly and I had this thought in

Posted by a gay man

By meanonymous92

An Unexpected Connection on a Fishing Trip
I'd see him fishing, old guy to me,but probably only 40. Ride my bike to this spot,hide it and walk up to this choice pool. 2 Trout and dinner for me and mom! Of course go home empty handed

Posted by a gay man

By KestrelElbow9092

A Surprising Encounter on the Couch
Part 5.2 How I discovered gay sex with older men and came to enjoy it. Todd sat back on the couch huffing from the orgasm I just gave him. He motioned for me to get back on the couch and with that

Posted by a gay man

By Deleted User

A Weekend Hiking Trip with Todd
Part 5.1 How I discovered gay sex with older men and how I enjoyed it. I spent weeks trying to distract myself. Only to let the images of his thick cock creep into my head at night while I

Posted by a gay man

By Deleted User

Exploring New Connections and Desires
Part 4. How I discovered gay sex with older men and how I enjoyed it. He dropped his pants around his ankles as he took a seat and I quietly imitated him. My cock stood at attention just as I sat

Posted by a gay man

By Deleted User

Exploring New Connections by the Pool
Part 3. How I discovered gay sex with much older men and found I enjoyed it. I wasted no time asking to come over the next weekend. This time Meridith had already left. It was her mothers birthday

Posted by a gay man

By Deleted User

An Unexpected Movie Night with Todd
Part 2. How I discovered gay sex with much older men and found I enjoyed it. By that Thursday I had nagged my grandmother about letting me go back. Meridith picked me up Friday afternoon and the

Posted by a gay man

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
#1
derake14
Gay Straight for Gay Straight
Parking lot kiss 31.3k 608 4.1k
#2
Tiffanyheels
Couple Trans Straight
Girlfriend takes two partners 68.6k 1.3k 3.1k
#3
KestrelElbow9092
Gay Straight for Gay Straight
Tricked him to sleep with me. 19.8k 346 3.1k
#4
cnysub
Gay Trans Straight
My Fun Bucket List 35.1k 471 2.7k
#5
kimorafoxxsexycd
Gay Trans Couple
My first big black 57.4k 987 2.5k
#6
sissyjamie4daddys
Trans Couple Straight
Sucking appendage in the club 39.2k 445 1.9k
#7
wally4u
Gay Trans Straight for Gay
From Zorbas To His Hotel Room 48.9k 268 1.8k
#8
Steve
Gay Straight for Gay Couple
Called back my massage therapist 39.6k 540 1.6k
#9
curiousladyd
Straight Couple Straight for Gay
First really big appendage 9.0k 342 1.2k
#10
Dedavis
Straight for Gay Straight
House hunting pt 1 36.7k 267 1.1k
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