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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 During Home Repairs
Fat Cock Part 1 70 yo white male, married, she's 73 and really not interested in sex anymore, hasn't been for 5+ years now, so I masturbate alot to porn. MY favorite type is MMF and

Posted by a straight man

By jediboner

College Friends Reconnect Over a Summer Bet
This happened today, but begin many years ago. In college I fooled around with other guys but had never bottomed before. Well one of my closest high school friends moved back this summer and we began

Posted by a straight man

By bitigerfan40

A Journey of New Discoveries in a Parking Lot
49 wm recently divorced and had never had any kind of encounter with a man. I had just separated from my wife and posted an ad for someone to teach me. Got a response from an older man with a nice 5

Posted by a straight man

By straightforhead420

Unexpected Reunion at a Craigslist Party
Many years ago I responded to a post on Craigslist, two guys who were mates looking for someone to come over and party with them at their home. So I pop on over and met them. two very nice easy going

Posted by a straight man

By G-BiDude

An Unexpected Connection at the Pub
I’d been living in the Cambridge Arms apartments for several months. I’d often go to this BP gas station for cigarettes around the corner. There was a black guy there who was friendly and

Posted by a straight man

By simplesex4us

An Unexpected Encounter in the Back Room
Part 2 m2m massage As his big 9 inch dick plunged into my throat he leaned down, taking my heart 8 inch cock in his mouth as he started sucking on it I couldn’t believe it. I was in a 69 with

Posted by a straight man

By Dedavis

Unexpected Meeting at the Bookstore Theater
Went to a bookstore a couple days ago. I was horny as hell . before I went in a big black guy was walking out and I looked at him and he said I like. I responded that I would love to find out. So we

Posted by a straight man

By georgeluvscum

An Unexpected Connection at the Bar
So my wife and i were having drinks at a bar one night. Dancing drinking just having a good time. We noticed this one fellow sitting by himself and asked him to join us for a drink. He told us that

Posted by a straight man

By hornedup1965

A Night of Truth or Dare by the Bonfire
Me, my wife (at the time), two other couples friends, and a single man were all hanging out and drinking around a bonfire. Someone suggested truth or dare, and we all kinda laughed. It was all pretty

Posted by a straight man

By u694me2

A Night of Unexpected Encounters
I'm recently single after a number of years, so I decided it was time for me to have fun with no strings but open to regular hook up. I'm white, but I'm only attracted to Black and

Posted by a straight man

By stormyocean871

My First Time at the Gloryhole Booths
(Part 2) of my first ever gloryhole experience at the booths... So i walked out, & not gonna lie I was hoping to see the man who sucked me off so good somewhere in the shop he was already gone,

Posted by a straight man

By dstroke

An Unexpected Visit to a Local Shop
(Part1) 12/24/25, Christmas eve, i went to work a few hours then i stopped at a Walmart to buy some last minute gifts, then I decided to drive by this Sex shop that's close by that Walmart,

Posted by a straight man

By dstroke

A Late Night Encounter in the Park
Back in the chat room days. ( yes it's been that long). I had only played in my adolescent years with other teens. I was late 20s by now. Married. But the idea of sucking again turned me on.

Posted by a straight man

By derake14

An Unexpected Connection in a Public Place
Im in my early 40 bi man. I'm in a relationship with an amazing woman she is fine with me being it actually turns her one seeing me get it like I like. Started talking to a guy off of here and

Posted by a straight man

By Someone

A Journey of Discovery at the Gloryhole
I remember the first time I swallowed. I was 27 at the time and sucked some cock by this age, but never swallowed. I went to a local gloryhole, found an empty booth with a hole, put my money in

Posted by a straight man

By demoman1970

A Mysterious Meeting on a Dark Night
Met a guy on here a couple years ago. We emailed back and forth for a week and a half. He was looking for head only and was wanting someone to come to his house. I only had fantasies and had never

Posted by a straight man

By mark32019

An Unexpected Meeting at the Barn
I'm a straight man that loves getting head from dudes! Does that make me gay or bi? Who cares? I'm searching on DL for a guy who can host. I come across and ad for a farmer, and the guy

Posted by a straight man

By nocqnocq321

A Surprising Meeting at the Park
Hello, this is part 1 I posted a story last week about how when I was younger I never had any interest in playing with men and then I had an experience with a gentleman at a park. Well I was in my

Posted by a straight man

By tazlovescock

An Unexpected Connection in the Mountains
I’m a straight man. I was online looking for a relationship. With a female. A long term relationship. I kept getting messages from an older gentleman than me. He asked if we could meet up. I

Posted by a straight man

By Deleted User

An Unexpected Discovery in the Garage
I am a straight man that loves to make love with a woman.One day I was at my wife's cousin's house and she was getting rid of a bunch of her clothes and shoes and high heels.I was going

Posted by a straight man

By Miniho

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 Straight
Parking lot kiss 36.6k 636 4.1k
#2
Tiffanyheels
Trans Couple Straight
Crossdresser and girlfriend 81.2k 1.4k 3.3k
#3
KestrelElbow9092
Gay Straight for Gay Straight
Careful what you wish for. 27.0k 373 3.1k
#4
cnysub
Gay Trans Straight
Ads on DoubleList 49.8k 557 2.9k
#5
kimorafoxxsexycd
Couple Gay Trans
Watched ex gf 79.4k 1.1k 2.8k
#6
sissyjamie4daddys
Trans Couple Straight
I love water 49.2k 464 1.9k
#7
wally4u
Trans Gay Straight for Gay
Pre-Halloween CD Dress Up! Part 1 53.9k 277 1.8k
#8
Steve
Straight for Gay Straight Gay
Gym kiss pt.2 50.0k 619 1.7k
#9
curiousladyd
Straight Couple Straight for Gay
First really big appendage 10.8k 370 1.2k
#10
powers8
Straight Gay Straight for Gay
Back with Michelle and Lisa 34.8k 353 1.1k
Page 1 of 50 · Showing 110 of 500 authors
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