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MILF Stories – Passion, Desire & Real Hookup Tales

What started as a fantasy of a more experienced woman turned into one of the hottest experiences of your life. Or you were just hanging out, and it turned into a steamy night that you still can’t stop thinking about. Sounds familiar? Well, if you have erotic MILF stories, post them here.

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An Unexpected Encounter with a Roommate
Gay encounter in this story. I played with neighborhood boys in my teens. But moved on to pussy. In my early 20s. Worked at a place. Made friends with a guy and we rented a 2 bedroom apartment.

Posted by a straight man

By derake14

A Night of Surprises at the Bookstore
When I lived in California I was dating this chick. She had no clue how to suck a cock and constantly complained that I fucked her too much. One night after another feeble attempt to suck my cock

Posted by a straight man

By leroy59

A Relaxing Getaway Turns Into a Surprise Connection
I was staying at nice hotel for a couple of days, there was a pool and a huge hot tub, I new it would be a relaxing getaway so I packed my stars and stripes bikini in hopes it would be open late

Posted by a straight man

By marcus874

An Unexpected Reunion at the Hotel
After posting an ad on double list, I finally got a serious reply. I had rented a hotel for the day not much communication between he and I just he had never been with a guy nor had I it was going to

Posted by a straight man

By Dedavis

A Surprising Meeting in the Grocery Store Lot
I’m a Married Guy bisexual have always been attracted to cock. But this is about my true Desire my kink the thing that lead me to my desires Ive always been attracted to older dad types. So i

Posted by a straight man

By Deleted User

An Unexpected Movie Night Encounter
I'd been messing around with this younger chick for a while when I was invited one evening to watch a movie on the couch. TV was on, we weren't alone and someone decided to put on an old

Posted by a straight man

By dmontag

Unexpected Connection at a Scenic Overlook
90 percent straight guy, but I really do enjoy a mouthful of cock or fucking a sweet boy's ass, from time to time! I was vacationing in the Traverse City Michigan area, and got a serious

Posted by a straight man

By richard__long

A Chance Meeting at a Gay-Friendly Beach
I'm not straight anymore, I'm recently divorced and free again, I met a bi curious man on Craigslist years back and we shared oral sex for a short time that's what got me interested

Posted by a straight man

By marcus874

An Unexpected Connection with My Stepson
I have been bi for years and recently placed my wife into a nursing home with Alzheimer's . My step son lives with me now and I know he is gay, just by the fact he never dates and leaves a few

Posted by a straight man

By charleyandsnickers

Unexpected Reunion with a Cruise Ship Bartender
Cruise ship true experience.This was our second cruise in two months on the same ship . On the serenity deck the last cruise I got to know the bartender and we talked . I knew he was gay because he

Posted by a straight man

By Deleted User

A Morning Visit to a Stranger's Home
I agreed to come to a strangers home very early in the morning, dress in lingerie and climb in bed with him. We texted but that was the extent of the communication. I did just that, I get to his

Posted by a straight man

By Kiny

A Bet at the Conference Bar Leads to Surprises
I have always considered myself a straight man. The more porn I watched the more I started to fantasize that I was the woman sucking cock. I found myself at a conference out of town for a week at

Posted by a straight man

By Deleted User

A Night Out: Unexpected Connections at a Concert
Went out of town with some friends to go party and watch a concert. I didnt really like this style of music but went for the party. Before going, I posted on here in that town. I was looking to sneak

Posted by a straight man

By derake14

A Married Man's Journey of Self-Discovery
A few years ago I came across a Bailey Jay video where she was dressed like a schoolgirl with pigtails and came in to give an amazing blowjob to her boyfriend. Then she lifted her skirt and she had a

Posted by a straight man

By Anonymous

A Memorable Reunion with an Old Friend
Abs3... soon as his friend cleaned up he left. He came in we talked, he helped clean me up and sucked me off. A month or so later we got together, he pushed my head down and got me to suck his cock,

Posted by a straight man

By sc4fun

An Unexpected Evening with Friends
Abs2.. after a couple months, he had been working on getting a finger in my ass, wasn't happening. He asked if he could call a friend to come join us. I'm thinking he'll lick my balls

Posted by a straight man

By sc4fun

A Surprising Meeting at the Bookstore
Abs1.. marriage wasn't in a good place. I started going to adult book store, met a few couples. Had a few of the gay guys try hitting on me but I was nope. This one guy would always ask or try

Posted by a straight man

By sc4fun

An Unexpected Night at a Friend's Place
So I was staying over at a buddies house one evening we had a few drinks and it got late and I didn’t feel like driving home so I decided to crash on the couch no big deal a few hours into the

Posted by a straight man

By Dedavis

A Night of Surprises and New Experiences
I can now admit that I am bi, and that I like to wear panties. I was talking to this guy for a while and we exchanged fantasies and body picks. He knew I was into panties and asked for pics of me

Posted by a straight man

By acbi4fun

A Journey of Self-Discovery and New Experiences
It was my first time with another man. I'm straight but fantasized about it for many years before the right opportunity came along. I was really looking forward to it and even bought a nine inch

Posted by a straight man

By rockinguy

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 39.4k 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. 28.4k 381 3.2k
#4
cnysub
Gay Trans Straight
Cruising in the Woods at the Gay Nature Campgrounds 53.2k 571 3.0k
#5
kimorafoxxsexycd
Couple Gay Trans
Gf knows I’m bi 82.7k 1.1k 2.8k
#6
sissyjamie4daddys
Trans Couple Straight
I love water 51.4k 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
Page 1 of 50 · Showing 110 of 500 authors
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