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An Unexpected Visit from My Girlfriend's Mom
When I was 18 I joined the Navy and after boot camp my training took place on the West coast, after my training I was stationed to a ship. During my training I was dating a girl that loved to fuck

Posted by a straight man

By triedasateen

A Surprising Nighttime Encounter in the Alley
My friends and i would drive around at night. It was 5 of us. 2 females 3 males. We play a strip game. Who ever touched the top of the car last would have go remove an item. One night i was just

Posted by a straight woman

By Deleted User

An Unexpected First Date Revelation
Not sure where to put this. I am intersex. It’s rare to be intersex and it’s even more rare to have both a penis and a vagina. I look like a female. I am very good looking. I have many

Posted by a TS / CD

By Deleted User

Exploring New Boundaries at the Swingers Club
I was with one girl for several years and it was amazing. She loved sex. She loved toys. She masturbated daily. She lived to be watched having sex. She would cum many times and be loud when she

Posted by a couple

By Tiffanyheels

A Night of Surprises in Palm Springs
Where do I begin so one night I was meeting with a date and we actually ended up going to a buddies house after we went to Palm Springs and we met up with another couple that were swingers. Long

Posted by a straight man

By peteana

Exploring Intimacy with My Girlfriend
Today while me and my ebony gf were getting kinky she was like since your bisexual have you ever recorded you and a man having sex I said yes. She was like put it on baby please I wanna fuck my dildo

Posted by a couple

By kimorafoxxsexycd

A Bi Couple's Adventure in Finding a Third
My gf is kinky as hell today she and I wanted to have threesome with anyone cause we're both bisexual well this trans man answered our ad of bi couple looking for 3rd. Well we invited him over

Posted by a couple

By kimorafoxxsexycd

Unexpected Encounters on a Friday Night
These sites are easy for women, we can get anything we want, even a chubby chick like me. Can't wait for Friday to end, have 3 cock already lined up, two at same time and another taboo guy

Posted by a straight woman

By KestrelElbow9092

Unexpected Encounter in the Grocery Store Lot
I remember messaging him for a while and was nervous about meeting up with him but I knew I eventually would and to this day I’ll never forget it and I’m glad I did see him even though he

Posted by a gay man

By teezeee

A Surprising Encounter in the Parking Lot
I remember messaging him for a while and was nervous about meeting up with him but I knew I eventually would and to this day I’ll never forget it and I’m glad I did see him even though he

Posted by a straight man

By teezeee

A Surprising Night from Craigslist Personals
The absolute hottest orgasm I ever had was when I was about 25. I was down and out because I kept getting cheated on. I got on Craigslist personals and mind you I had kinda thought about guys before

Posted by a straight man

By discretebottom01

A Day at the Local Nudist Resort
Warm day. Decided to go to a local nudist resort to lay in the sun. Great weather here in Tampa. Only stayed at the resort for 30 minutes. Feeling horny I went to nearby ABS. I have a few I enjoy.

Posted by a straight man

By barefootlover

An Unexpected Invitation to a Party
I was always feminine, you could say, very gay 5'4" 120 lbs. Started dressing after high school after I moved into my own place. my landlord's are a gay couple and they told me they

Posted by a TS / CD

By cnysub

Unexpected Meeting in an Adult Bookstore
I have to tell you, I’ve missed your mouth. And you of course. I was so horny the other day, I went to an adult bookstore. I saw an open booth, just across from an occupied booth. I went into

Posted by a straight man

By edgemegood

A Surprising Morning Encounter Before Christmas
Before Christmas started chatting with a woman from DL and she liked meeting before work in the morning We decided to meet at her place She meets me at the door in a sexy robe and takes me upstairs

Posted by a straight man

By rockb0073

An Unexpected Meeting in the Ravine
I used to walk down through the ravine as a short cut. One day I notice an older man coming out of some bushes with another younger man. They parted ways which I thought was unusual. Them realized

Posted by a gay man

By bjondjon

An Unexpected Connection During Therapy
Been into orgy 😁/therapy session for two years and I must say I had the best experience last week from trans woman it was the best have ever had she had me cum three times and she did as well what

Posted by a straight woman

By Patricia

A Chance Encounter in the Grocery Store
Almost 60, retired for a year and go to the grocery store almost every other day. Have the time and saves me from wasting food. Yea I began getting friendly with everyone who worked there and started

Posted by a straight man

By KestrelElbow9092

A Night Out at the Gay Bar Adventure
Me and my ebony wife got sexy she did my wig makeup nails and dressed me and helped me with my breast forms. Then we took a Uber to the gay bar me and her were having a drink talking about us both

Posted by a couple

By kimorafoxxsexycd

A Secret Meeting at Home: Unexpected Connections
We corresponded for about 3 days…often describing what we would do to each other when we met., our wives don’t put out anymore, and haven’t in a while. We’re always horny

Posted by a gay man

By Scott

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
Straight Gay Straight for Gay
35 years later 39.5k 655 4.2k
#2
Tiffanyheels
Trans Couple Straight
Crossdresser house party 83.9k 1.5k 3.3k
#3
KestrelElbow9092
Gay Straight for Gay Straight
Careful what you wish for. 28.5k 381 3.2k
#4
cnysub
Gay Trans Straight
Cruising in the Woods at the Gay Nature Campgrounds 53.3k 571 3.0k
#5
kimorafoxxsexycd
Couple Gay Trans
Gf knows I’m bi 82.8k 1.1k 2.8k
#6
sissyjamie4daddys
Trans Couple Straight
I love water 51.5k 464 1.9k
#7
wally4u
Trans Gay Straight for Gay
Pre-Halloween CD Dress Up! Part 1 54.7k 277 1.8k
#8
Steve
Straight for Gay Straight Gay
Gym kiss pt.2 50.4k 623 1.7k
#9
curiousladyd
Straight Couple Straight for Gay
First really big appendage 11.2k 374 1.2k
#10
butchmax
Couple Straight for Gay Straight
She didn't know till we where married 44.6k 384 1.1k
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