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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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Unexpected Connections at Nesbitt Park
Early morning at Nesbitt Park There are many regulars there. Mostly older. I sucked many of them. Well I got there early one morning. There was only one truck parked there and again it was an older

Posted by a straight man

By sucker365

An Unexpected Shower Experience with a Friend
When I was younger I would spend the night with a friend! On one of those sleepovers my buddy told me to take a shower with him! He said that we could get through quicker so I jump in the shower with

Posted by a straight man

By jughead22

An Unexpected Connection During a Home Visit
Straight married man here. Was moving me and the family into a new home and by myself had to go let the cox cable guy in. Talk quiet guy, real nice and talked about his wife and kid he has at home. I

Posted by a straight man

By strictly4funsd

Unexpected Connections at the Adult Theater
I've always been a orally bi man since I was a teenager. I used to suck off my bestie since high school. And that continued on through our adult years and our marriages. He went through some

Posted by a straight man

By OysterRidge3767

A Journey to Unexpected Love and Intimacy
I’ve been actively bi for many years since my divorce. Started out with a fascination of just sucking his cock. Then sucking and swallowing…..then….well you get the idea. I

Posted by a straight man

By Frank

Exploring New Experiences at the Adult Theater
It's been about 5 years now where I became obsessed with my ass in cheeky shorts. It started with me sneaking my wife's thongs when I had alone time. Gradually I was full on in lingerie of

Posted by a straight man

By bjc09

An Unexpected Reunion at the Gas Station
A couple of days ago I had the most amazing thing happen to me. I was at a gas station filling up my car when this guy pulled up to the pump right next to me. He looked really familiar to me until

Posted by a straight man

By leroy59

A Surprising Encounter at the Gas Station
A couple of days ago I had the most amazing thing happen to me. I was at a gas station filling up my car when this guy pulled up to the pump right next to me. He looked really familiar to me until

Posted by a straight man

By leroy59

An Unexpected Encounter in a Steam Room
I was in New York recently. Looking for some exercise I asked the concierge for a recommendation. He sent me to an athletic club with an indoor pool. After a good swim I went in the steam room. It

Posted by a straight man

By bobby63

A Policeman's Unexpected Encounter in the Park
Being a policeman led me to get involved with and learn a lot about others. Their behavior as well as their sexual habits. I never imagined I would eventually get involved in sex with other men.

Posted by a straight man

By charleyandsnickers

Summer Days on the Family Ranch
Mimicking what he’s done as best I could. I was thinking to myself, “I sure hope he is enjoying this as much as I am?” He lasted twice as long as the 5 minutes I did. But it

Posted by a straight man

By C*ck S*cker

A Mysterious Meeting in the Shadows
I'm a mid 40s married man. My wife was gone for work tonight and I ended up scrolling thru grindr. I ended up chatting with a 23 yr old female to male trans. I really doubted that this person

Posted by a straight man

By bline420

An Unexpected Visit to a Friend's House
Side job part 2 - So after a couple weeks I got back with my girl friend and wasn't getting any calls from my friend to do any jobs so I decided to message him and asked if he had any work. Even

Posted by a straight man

By Deleted User

Exploring Curiosity in a Forest Setting
In my early 30s I was very intrigued by the world of gay cruising. Most of it was just the curiosity of people watching or the adventure of stumbling upon others having fun doing what they came there

Posted by a straight man

By nrtyrnt

A Summer Gathering at the Beach House
I was house sitting at a friend’s beach house for a few weeks. One morning several friends stopped by for a swim, we drank mimosas and tequila, got stoned and just generally lazed about.

Posted by a straight man

By HoopoeFlame7061

A Biking Adventure and Unexpected Encounter
I spent the morning biking and mid afternoon i saw a trail heading into the woods. I rode in and after a while came into a large clearing with trails splitting off into the clearing. I followed a

Posted by a straight man

By mnoutdoorsman

A Curious Game of Reveals and Surprises
I'm straight. Years ago I read a post from a guy that was "curious" and wanted a chance to see someone's cock up close. Not sneak a peek at the gym and not a pic or porn. I

Posted by a straight man

By LionAnchor5526

Exploring Connection and Intimacy in Bed
I guess I'm bi, I've drempt many times of a thick man's member to satisfy. Laying naked with him in his bed, he's looking at the ceiling, a heavy man with his man nipples just

Posted by a straight man

By lesvt54

An Unexpected Visit to the Garage
After turning into a cocksucker, I was running an add for cock, and not getting any action at my age (old), and I guess I should have asked for stats etc. but I did request a pic., I got an answer

Posted by a straight man

By butchmax

A Camping Trip That Changed Everything
After 25 years of friendship, I couldn’t believe what happened. Me and my black friend had gone on a camping trip. We were staying in a nice cabin, but there was only one room in one bed.

Posted by a straight man

By Dedavis

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. 28.5k 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 51.4k 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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