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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 Invitation to a Unique Gathering
The gangs all here. I got invited to a condoms optional gangbang last week. I saw the post on here and it was my 1st time at a gangbang. If others are like this, I will be going to more. I was

Posted by a straight man

By sissyjamie4daddys

An Unexpected Visit While House Sitting
U was house sitting for a family.member and lonely. I placed an ad on DL for any stressed college guys who needed a NSA cock sucking and I would host. I got a reply pretty quick and gave my address

Posted by a straight man

By bigstickhick

A Night Out in Fort Lauderdale: Unexpected Connections
I was in the Air Force. We went to For Lauderdale in Florida for a training exercise. After the exercise, which lasted two weeks, we went out to town to party. I went with some friends to a straight

Posted by a straight man

By Deleted User

Best Friends Exploring New Boundaries Together
I just read the story about being very young your first mm experience.i could hardly believe how close it was to my experience. My best friend and I started playing with our cocks when we were

Posted by a straight man

By bobby63

Exploring Bisexuality with an Understanding Partner
I def mean more to bisexual. Don't get me wrong, I still like pussy, but I LOVE dick. Dayummm do I ever love me some good ole hard dicks. I have a very understanding wife. She allows me to fuck

Posted by a straight man

By sissyjamie4daddys

An Unexpected Encounter in the College Bathroom
When I went to college I spent more time chasing women than studying. When I wasn't having any luck I found a remote mens room and would jack off.one day I was doing just that when I heard

Posted by a straight man

By bobby63

Unexpected Connection at a Doctor's Party
I was in the Marines when this took place. I was invited to a party by a friend who worked for a doctor. This doctor had a really nice home and was extremely drunk when I arrived. As we were

Posted by a straight man

By leroy59

A Journey into New Relationship Dynamics
I'm a mid sixties mwm and closeted bi. I placed an add on double list and got a response. All I was interested in was giving my first blow job. The guy asked if I could get naked on my knees. I

Posted by a straight man

By canthost

An Unexpected Encounter in Bustiers and Robes
I started enjoying cocks later in life. I used to have a guy come over who liked to wear panties when he blew me. Several months into this I returned the favor and have loved cock ever since. It

Posted by a TS / CD

By likes big ones

A Surprising Connection with a New Shower Buddy
His screen name was Silver Daddy. We meet at an online site. Our wives both lost interest. He wanted to be my new shower buddy. I finally invited him over one day when I was home alone. When he

Posted by a straight man

By hoog7515

Unexpected Connections in an Adult Bookstore
I'm a bi bottom sissy who is an easy fuck. I love men and woman the same. If I can't get a piece of ass from a female, I ALWAYS give up my ass to men. I do prefer getting my ass and mouth

Posted by a straight man

By sissyjamie4daddys

An Unexpected Encounter in the Guest Room
Buddies Part one I answered an ad looking for a guy who enjoyed giving oral to other married men. We set up a date when his wife would be out of town for a few days. I knocked on the door and he

Posted by a straight man

By LT_Mike

A Chance Encounter in Orange County
Fuck I love reading this stories about guys hooking up with other guys, they get me so Horny. I would love to meet up with a man who’s between 30 and 60 with at least 7” or more. I gave my ass

Posted by a straight man

By Deleted User

An Unexpected Meeting in the Elevator
Yesterday I got a reply to my ad on DL. I was looking for a feeder to satisfy my urge. After some email back and forth he gave me his address. I showed up it was a high rise condo building he had

Posted by a straight man

By Deleted User

An Unexpected Visit to a Highland Park Home
I used to go to a house near Highland park where a gay couple lived. I'd come in and they'd strip me down. I would be so excited on my way over that I was already hard. They would take

Posted by a straight man

By SwanHedge6783

Unexpected Moments with a Helping Hand
Stayed home to work on the house, wife went to work. A buddy stopped by to help with some broken sprinklers. He was seperated going through a divorce. As we were working in the back yard he said one

Posted by a straight man

By ToucanCairn3613

A Curious Encounter with an Older Man
I am a masculine bisexual hairy bear that loves to orally satisfy both sex’s. Women are so sexy with their curves and a nice cock is great to play with too. So I meet this older gentleman on CL

Posted by a straight man

By thegreatbear

A Birthday Surprise with Friends and Fun
I'm straight but had a few male encounters in the past. My gf wanted to watch me with a guy, so her birthday was yesterday, I told her I would put a show on. Little did she know, I invited over

Posted by a straight man

By wantinit73

An Unforeseen Connection During Lunch Break
Just had my first bi experience I was working on older man's plumbing when I said I was going to take lunch break he said follow me went down Hall to his bedroom he pulled my shorts down with no

Posted by a straight man

By Deleted User

An Unexpected Hotel Meeting with a Crossdresser
I am a bisexual man. My first experience with a crossdresser happened many, many years ago. I was dating this bisexual, married couple, and I would see the crossdressing hubby on the side. His

Posted by a straight man

By lit_writer

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 Couple
The fast and furious 61.3k 867 4.4k ↘
#2
Tiffanyheels
Straight Couple Gay
Girlfriend and her attractive daughter 142.3k 2.1k 4.0k ↘
#3
kimorafoxxsexycd
Trans Gay Couple
I love being on my hands 130.7k 1.4k 3.5k ↘
#4
cnysub
Gay Trans Straight
Adult Theater 77.7k 709 3.3k ↘
#5
KestrelElbow9092
Straight Gay Couple
Light on Dark 49.6k 521 3.3k ↘
#6
sissyjamie4daddys
Trans Couple Straight
I love water 72.6k 488 2.0k ↘
#7
wally4u
Gay Couple Trans
I Guess He Did Have To Go! 68.4k 311 1.9k ↘
#8
butchmax
Straight Gay Couple
I was FED UP 89.9k 633 1.8k ↗
#9
Steve
Straight Straight for Gay Gay
Visiting auntie 54.3k 647 1.7k ↘
#10
powers8
Gay Straight Straight for Gay
A fantasy come true 83.8k 671 1.7k ↘
Page 1 of 50 · Showing 1–10 of 500 authors
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