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An Unexpected Connection with My New Roommate
Searching for a new roommate I luck out and find a shemale, we agree that from time to time we might require some sexual activity. A few weeks later we find ourselves home alone and nothing to do.

Posted by a gay man

By Deleted User

Unexpected Bonding with My New Roommate
I lucked out in my roommate ad, she turned out to be a shemale and I was gay, what a great connection. It was several weeks since she moved in that we found ourselves home alone. Her cut off short

Posted by a gay man

By Deleted User

A Small Town Encounter Over Drinks
Being bi-sexual I had looked for a man to get together with for about 6 months as I live in a smaller town, a bit off the beaten path. When I texted a bi-sexual man and we met for a drink he told m

Posted by a gay man

By EagleNexus5361

An Unexpected Encounter in a Supermarket Lot
I saw a post for a guy wanting to "explore" and we agreed to meet. He got in my car and we talked a little, he had never been with a man before, just saw other guys in locker rooms and

Posted by a gay man

By alaskastoner

Discovering a Hidden Meeting Spot in the Countryside
I'm in my 50's married, not out to her It was always hard finding a place to hook up. Doing it In cars, is a bit of a downer. Too many guys in the same situation. Then I answered an ad

Posted by a gay man

By jlmmm

Exploring New Boundaries in Marriage
Here's how my twenty year marriage ended. I'd always wanted to try a threesome or swap. But my wife, ex-wife now, said no, hell no. We had a good sex life, but, you know how stupid guys are

Posted by a straight man

By reggie_boy

An Unexpected Connection at Home
I met a guy on here the other day. I'm 60 more a bottom. He's 56 more s top. So after a few talks we got together. We got undressed. He had a noncut 5 1/2 dick I thought damn, a bit smaller

Posted by a gay man

By jlmmm

An Unexpected Meeting Leads to Connection
I meet him on here and he set up a time to meet up and I got there and we talk and then we drop off are pants and got on the bed and I started to suckered his nice fat cock for some time and then

Posted by a gay man

By Heavyman60

From Coffee Shop Friends to Something More
We met at a local coffee shop and became friends share coffee and conversation. Then one day he was feeling bold and asked me if I ever thought of exploring man on man sex. Hesitating for a moment

Posted by a gay man

By Deleted User

An Unexpected Meeting at the Steam House
I met this guy once at the steam house he was black man I must’ve sucked his 14 inch cut cock for a hour straight. Then he’s like it’s ur asses turn I look at him I’m like

Posted by a gay man

By Deleted User

An Unexpected Thursday Reunion
The married man that’s been my lover for the past 2 years emailed me about wanting to get together again.  I hadn’t been with him in for a few weeks, and I had been getting tired of

Posted by a gay man

By dlsenior

An Unexpected Connection After Work Hours
I am a life long (or at least since puberty) closeted bi. I am old enough that adult magazines were all I had to masturbate to when I was in puberty. I loved the normal tits, ass and pussy but there

Posted by a gay man

By daadah

An Unexpected Late Night Encounter
I posted looking for a " nsa" top, and only had a couple replys. It was getting late and was going to give up. I looked at post's one last time and saw "top looking for rn"

Posted by a gay man

By TernRidge3971

Unexpected Dinner Invitation After Christmas
THE NIGHT AFTER CHRISTMAS, PART ONE: It's been a very dry pandemic for me. One friend and I had gotten together one time. He's a good guy that is overall very careful both before pandemic

Posted by a gay man

By chicagonormalguy

A Weekend of Unexpected Connections
I was over at my friend's house. Both our husbands had decided to go hunting for the week. We are both mid 30s very good shape. On day three , we had gone to dinner, started drinking a little

Posted by a gay woman

By jlmmm

A Chance Meeting at the Park
I have seen this younger guy at the park. Now it has consumed all my thoughts. I know he plays with men. Just can't get pass the way I feel for him. I dream about sucking each other off. Then I

Posted by a gay man

By jakemo

An Unexpected College Night Encounter
Im a gay 24 college student and wanted to have some one Saturday night - I found this older guy on here he was 42. Messaged back and forth I was horny and had a couple shots I told him i was in my

Posted by a gay man

By Deleted User

An Unexpected Night with a Young Stranger
I picked up a boy named Travis a 20 year smoking smooth native boy he has shoulder length black hair & a wide 14" cut cock I blew him about 5 times during the night & he fuck rd me 2

Posted by a gay man

By funguy6925

An Unexpected Visit Leads to New Experiences
I have had a good number of experiences with men since my first when I was in my 20s. More about that first experience in another story though. I really enjoy passionate play with men but I also like

Posted by a gay man

By Anonymous

Unexpected Meeting in a 55+ Community
I'm a cocksucker, have been most of my life. I have about a dozen guys that I service on a regular basis. Yesterday I was very hungry for some cock and I could only see one of my regulars so I

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 31.5k 608 4.1k
#2
Tiffanyheels
Straight Couple Trans
Female friend turns to hot intimacy 69.5k 1.3k 3.1k
#3
KestrelElbow9092
Gay Straight for Gay Straight
Tricked him to sleep with me. 20.1k 348 3.1k
#4
cnysub
Gay Trans Straight
My Fun Bucket List 35.7k 473 2.7k
#5
kimorafoxxsexycd
Gay Trans Couple
My first big black 58.2k 991 2.5k
#6
sissyjamie4daddys
Trans Couple Straight
Sucking appendage in the club 39.4k 445 1.9k
#7
wally4u
Gay Trans Straight for Gay
From Zorbas To His Hotel Room 49.1k 269 1.8k
#8
Steve
Gay Straight for Gay Couple
Called back my massage therapist 39.7k 541 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 36.8k 267 1.1k
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