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A Rainy Day Encounter in New York City
KJ real encounters.. Story 1. Some places and names may be altered for privacy reasons. The first time I was with a man was when I was around 23. I had moved to NYC studying at NYU the year before

Posted by a gay man

By shynewbie

Unexpected Encounters at the Local Mall
Bi guy living on the Seacoast in NH can be a challenge meeting guys when you cannot host. Last week I was near a local mall and decided to open Grindr while walking through the mall. I see a profile

Posted by a gay man

By chillguynh

A Surprising Friendship in a Small Town
I went to school in a small town in Virginia and one day after school I was sitting on the steps looking at two blacks one about my age and one who was a couple years older. Their family had moved to

Posted by a gay man

By gg1548

Unexpected Encounter at the Air Force Base
My dad was an Air Force spider pilot and he was the base commander when we were stationed in Alamogordo, New Mexico. There was a sexy enlisted man who cruise me at the BX every weekend for about

Posted by a gay man

By lovemanmusk

Navigating Identity and Acceptance Through Life's Challenges
At a young age it all started with my neighbors youngest son. It has grown to as many as 75 men sometimes more than once. I’ve come a homosexual and the best ass the most older men love. I

Posted by a gay man

By laymeplease

A Journey of Unexpected Vulnerability and Trust
Part 3 of whenever I'm done telling my experience. As I was saying each spank was painful but somehow I guess my adrenaline kicked in and it felt good. My ass must be burning and before I

Posted by a gay man

By shynewbie

An Unexpected Photography Session with a Young Athlete
This happened a few years ago when I was in my mid 40's. I'm a part time photographer in Chicago & a friend of a friends son wanted some pictures taken of himself. He wanted some

Posted by a gay man

By djr18

A Surprising Encounter in Suburban Istanbul
Part 1 of not sure how many parts So my bath house experience was followed by a visit to the Turk's home and he fucked me again at his place. Here's what happened. As it turns out it

Posted by a gay man

By shynewbie

A Mysterious Encounter on a Dark Road
Earlier story was submitted after I accidently press send before I finish. So I was being fucked in both ends by these 2 Turks, and they took turns fucking me and my struggles were useless but I

Posted by a gay man

By shynewbie

An Unexpected Connection at Work
So I’m 44yo gay. I work construction Part 4. So we snuggled for a couple hours as we slept naked with each other. I think he slept and I just kept rubbing his amazing body. I couldn’t

Posted by a gay man

By Deleted User

A Summer Encounter at the Beach House
Growing up in a small Southern town in north Florida, I never really pursued any 'alternative' sexual lifestyle. I was a surfer punk with long straight blonde hair and Jeff Spicolli (Fast

Posted by a gay man

By comomaturebottom

A Shocking Revelation During a Quiet Afternoon
Caught I was married for about three years when I was caught by my wife and our marriage ended immediately. I worked at night and she worked during normal business hours. I was an undercover total bi

Posted by a gay man

By Anonymous

Exploring Friendship on a Business Trip
I'm 50 BI married guy, who has a FWB when I travel to our companies home office. I don't travel often, so we are only able to get together once or twice for years. He's in his mid

Posted by a gay man

By johnsmith9512

A Surprising Meeting at the Steam Bath
This is short story about one of my encounters at the Steam Bath, I was feeling really horny one morning and really wanted to suck a nice cock. I decided to go to the bath house and see what was

Posted by a gay man

By radioman666

A Relaxing Guys Weekend in the Hot Tub
So I’m 44yo gay. I work construction Part 3. So Friday morning we are chatting and he tells me his gf is going with the girls on a ski weekend up in N Conway. Normally I wouldn’t give a

Posted by a gay man

By Deleted User

Unexpected Encounter in a Bookstore Room
My friend with benefits...after about a year of being his bottom..he said he wants to share me.. I was surprised and turned on..we got a room by bookstore off interstate I got ready in room..he put

Posted by a gay man

By KestrelMoon7752

An Evening of Exploration at a Private Party
I'm a bi submissive male 44 years old with experience being a sub, my Mistress for many yrs. moved away I answered an ad on DoubleList from a Dominate couple in their 50's looking for a bi

Posted by a gay man

By cnysub

From Dorm Friends to Wedding Best Man
This happened when I was in college. I'll change the names of him and I.moved into the dorms my junior year and met several guys from my floor that I became fast friends with, but one day in the

Posted by a gay man

By rhydr

A First-Time Encounter from an Online Connection
The first time I was 35 I had been practicing with a dildo for a couple weeks and felt like I was ready. I got on craigslist and linked up with a 25yr old black guy who had a 7.5 cock. He came to my

Posted by a gay man

By rabbit2021

A Journey of Friendship and Connection
He was my fwb...meet him on Craiglist back in the day . We met at a park by his place.first time..to say hi What a cock..9"+..thick..wanted a bottom to be his What started to be 6yrs of fucking

Posted by a gay man

By KestrelMoon7752

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
Gay Straight for Gay Straight
Parking lot kiss 33.1k 617 4.1k
#2
Tiffanyheels
Trans Couple Straight
Crossdresser girls night out 74.6k 1.3k 3.2k
#3
KestrelElbow9092
Straight for Gay Gay Straight
Beautiful and Black 22.4k 352 3.1k
#4
cnysub
Gay Trans Straight
The Theater 42.2k 501 2.8k
#5
kimorafoxxsexycd
Couple Gay Trans
New love with ex gf 64.8k 1.0k 2.6k
#6
sissyjamie4daddys
Trans Couple Straight
Sucking appendage in the club 42.2k 454 1.9k
#7
wally4u
Gay Trans Straight for Gay
From Zorbas To His Hotel Room 49.6k 270 1.8k
#8
Steve
Straight for Gay Straight Gay
Gym Kiss unexpected 44.7k 569 1.6k
#9
curiousladyd
Straight Couple Straight for Gay
First really big appendage 9.6k 349 1.2k
#10
Dedavis
Straight for Gay Straight
House hunting pt 1 37.5k 271 1.1k
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