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A Unique Birthday Surprise at the Motel
Part 3 of the trail. . .  I've been cruising the trail and sucking cock and getting fucked as often as I can, my wife now likes to go dogging about once a week. I noticed many of the

Posted by a gay man

By cnysub

An Unexpected Encounter with a Neighbor
I met Scott on a site called Manhunt. He lived just down the road a bit so I walked to his apartment. After a bit of small talk we went to his bedroom, got naked and climbed on his bed. He pulled my

Posted by a gay man

By ParrotHinge5867

An Unexpected Friendship at Work Leads to Surprises
I was in my early 20s and befriended an older guy (in his 50s) at work. I had been to his place a few times for drinks. This time we had drinks as usual and my friend pulled out a trans porn tape

Posted by a gay man

By Deleted User

Unexpected Connection at the Hotel Bar
I was at a hotel bar and saw this sexy ass woman sipping a whiskey. I introduced myself and immediately knew she was a he but I didn't say anything, it turned me on. We talked until the bar

Posted by a gay man

By TaipanBrook6308

Exploring New Experiences at a Bathhouse
My first time in a bathhouse…I had to head up to Canada for an event so I looked up bathhouses and found one called Club Xcess. That night I headed to the place and when I entered I found

Posted by a gay man

By ParrotHinge5867

An Unexpected Reunion Leads to Surprising Connections
The 2nd time I hooked up with a guy who plowed my ass…his name was Nick. We had chatted online before we discovered we knew each other! I headed over to his place and we headed to his bedroom.

Posted by a gay man

By ParrotHinge5867

Unexpected Encounters at the Softball Tournament
My biggest regret my wife and I hadn't been married long we were at a softball tournament and all of us went out for drinks at that time i had no idea how unfaithful my wife was so we had a few

Posted by a gay man

By Deleted User

Exploring Unique Turn-Ons in Relationships
I love it when a guy asses me if he be able to piss in my ass or mouth it is a big turn on to me and I like to have it done more often black or white or both

Posted by a gay man

By tiny

An Unexpected Encounter at the Lake Park
I'm a middle aged biwm who prefers women when it comes to relationships, but I love the naughtiness of secretly loving hard cocks to stroke and suck, and to be pleasured as well, especially with

Posted by a gay man

By Deleted User

An Unexpected Encounter in a Walmart Bathroom
I'm bi but really like cock. My first experience wasn't on a site at all. I was at a Walmart and in the bathroom when I see a foot tapping under my divider. I don't think about it at

Posted by a gay man

By lookingtopleaseamilf

A Surprising Meeting at the Campground Shower
My first experience with a guy was when I was a teenager. Our family would go camping at the beach in the same campground every year. The bathhouse showers was one room with 5 shower heads. Being shy

Posted by a gay man

By look_

A Surprising Connection Through Online Chat
The first time I had a nice big cock take my ass cherry… I had done oral with a guy when I was 19 but still needed to find someone to complete my bi fantasy of getting plowed by a guy. I was

Posted by a gay man

By ParrotHinge5867

An Unexpected Connection on the Way Home
The second guy I ever hooked up with was an older man I met on here. He lived in a city I would drive through to visit my family, and responded to my ad looking for a top that was on the way to my

Posted by a gay man

By Deleted User

A Young Adult's First Encounter After College
My first time happened when I finally moved out of my college dorm. I was 19, with a tall, lean swimmer body, and posted an ad looking for my first top. The guy I picked was a 46 year old with a 7 in

Posted by a gay man

By Deleted User

An Unexpected Encounter at the Sink
Brother part 4 I pulled the panties down he said stop pull your cheeks apart I still have cum in my ass he says oh my God thats so hot beg me to fuck you now I said fuck me please he said you can do

Posted by a gay man

By Deleted User

A Late Night Encounter Through Craigslist
True story. So this was back in 2006. This was when Craigzlist had a personal section. It was very active and popular. I was in my late 20s and was pretty much bi my whole life but never acted on the

Posted by a gay man

By leemike812

An Unexpected Connection at the Adult Store
I was fresh out of the military and was at the local adult store. Young and in shape this older guy, mid 40’s, kept standing next to me as I looked at gay magazines and chicks with dicks. I was

Posted by a gay man

By NewtBirch3996

Unexpected Encounters During a Business Trip
I am a mature business traveler. I arrived in a west coast city on Sunday afternoon and was hornier than usual. I put a post online here, as well as another m4m site. Holy crap. I got so many emails

Posted by a gay man

By biztravelerinurcity

A First Encounter at His Apartment
My first time was with John He was a little older than I and thru our connection he was a dominant top and I was the sub bottom. I went to his apartment and we had small talk but we both knew why I

Posted by a gay man

By dgs755

A Surprising Meeting on the Nature Trail
Being a senior citizen I walk for exercise, I walk on the trails in woods not far from my home. I am married and sometimes my wife walks with me and other times I go by myself, today I'm by

Posted by a gay man

By cnysub

Top Authors

Discover the most engaging creators on Doublelist — ranked by views, listens, and upvotes, with fresh voices breaking in every week.

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derake14
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Tiffanyheels
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Sucking appendage in the club 40.9k 453 1.9k
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From Zorbas To His Hotel Room 49.2k 267 1.8k
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Steve
Straight Straight for Gay Gay
2nd part to gay club experience 43.0k 559 1.6k
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curiousladyd
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