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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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A Surprising Meeting in the Alley
I am st8 married happily to a beautiful younger girl. I am 53 and recently have been thinking of man to man sex with me being the bottom. I placed an ad on a site but I had no responses until a day

Posted by a straight man

By Deleted User

An Unexpected Encounter in National City
In 1982 I was in National City, drunk, and was picked by two 60 yo fat white guys. Stan 68 and Rusty 65. They took me to their home, put on some porn, sat down on the couch with me in the middle.

Posted by a straight man

By Deleted User

A Surprising Moment During a Friend's Visit
I went over to help a buddy move some furniture from one apartment to another. We just finished up and we had decided to go to dinner after we got done. He said he was going to the bathroom and then

Posted by a straight man

By Dedavis

An Unexpected Encounter in the Hallway
Part 2 … on my knees, getting my throat fucked by the 65-year-old man’s 12 inch cock, his balls, large and hanging slapping on my chin as he went deep into my throat he smiled looking

Posted by a straight man

By Dedavis

A Surprising Connection in a Public Restroom
Well, it started weird but ended hot… I was standing at the urinal at the mall bathroom. I saw this nice looking older guy mid 60s walk in didn’t look his age for sure he got in the

Posted by a straight man

By Dedavis

Unexpected Encounters with Friends: A Unique Journey
I have sucked a lot of cocks in my time for a man. As a boy I sucked a lot of my friends off. I think it's because I've always been feminine looking and pretty. I sucked off 3 brothers 1

Posted by a straight man

By chillas

A Surprising Meeting at the Bookstore
Who in tarnations puts a bus stop outside of an x-rated bookstore? I made a mad dash for the bus and it was pulling away as I got near. It was hot outside so I took refuge in the bookstore. It was

Posted by a straight man

By leroy59

A Night of Laughter and Connection at the Holiday Party
My friend and lover of late invited me to my 1st Holiday party of the year. A is 70 yo, 5.5" cock. We have wonderful sex and I was excited to attend the party. A introduced me to B, the host, a

Posted by a straight man

By oldandfun

A Surprising Encounter During a Massage
This was my first guy on guy experience it happened after I got seduced during a massage. I never went to college and I never had the opportunity to experiment and never really had any fantasies or

Posted by a straight man

By honeybadger514

A Surprising Meeting at the Local Park
I want to start this story out by saying that when I was younger I had no interest in playing with men at all!! Then one evening I had a fight with my girlfriend, I grabbed some beer from the fridge

Posted by a straight man

By tazlovescock

Exploring New Dynamics in Our Relationship
Always had a great sex life with. My wife always keep it spicey decided to try some bisexual stuff with a guy after we had played with a women for a couple years anyways had a guy respond to our DL

Posted by a straight man

By Rusty shakleford

Exploring New Feelings in a Comfortable Space
Dan meet me at the door and let me in there home Dave greeted me once inside Dan led me to the shower and gave me a towel and told me to go ahead and clean up and put on the robe I was very nervous

Posted by a straight man

By Assround

An Unexpected Encounter in a Hotel Room
I’ve never been with a man nor touched another man’s cock until the night I had to share a hotel room with one of my coworkers, a good looking black guy in his early 40s after having

Posted by a straight man

By Dedavis

A Summer Pool Gathering with Friends
I met a guy on dl , nice guy . Close and had a few hookups … One day he asked if I’d be interested in a group scenario. Of course I said yes It was summer and he had a secluded pool

Posted by a straight man

By eaglesfan3

A Surprising Meeting Outside the Bookstore
On all outward appearances im a regular straight man, but behind closed doors i love being a slutty little cock sucker. It all started when I was about 26 years old. After years of watching porn and

Posted by a straight man

By natelee75

A Mysterious Meeting Behind the Mask
I occasionally want to take on the female role and this was one of those times. I screened the applicants made a choice and told him to come by at a certain time. We both agreed to minimize

Posted by a straight man

By littlerichard96

A Couple Explores New Dimensions of Intimacy
So i have always enjoyed playing with my butt. Since i can remember i liked sticking my finger in it. Now going through life it was my dirty little secret. As a young adult i bought a toy and i

Posted by a straight man

By BisonLodge6610

A Weekend Adventure with Friends in Nature
There is a crew of 8 guys that I hang out with. Sporting events. Golf. Ect. One of the guys I have suspected was probably bi . He was just more fem not overly masculine. Nice guy and all. I have

Posted by a straight man

By derake14

An Unexpected Connection: Meeting Online
Where to start as young Man I always find myself enamored when watching a woman take a hard fuck from a big cock. I have find myself playing with toys up to the size of 7 inches long and 5 inches

Posted by a straight man

By Just ask

Old Friends Reconnect and Share Secrets
I've had a guy that I meet 15 years ago. We became pretty close over the years. He was divorced when we meet. But he was always chasing the girls. My wife said he was gay or at least bi. But in

Posted by a straight man

By derake14

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 36.7k 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 49.9k 557 2.9k
#5
kimorafoxxsexycd
Couple Gay Trans
Watched ex gf 79.5k 1.1k 2.8k
#6
sissyjamie4daddys
Trans Couple Straight
I love water 49.3k 464 1.9k
#7
wally4u
Trans Gay Straight for Gay
Pre-Halloween CD Dress Up! Part 1 54.0k 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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Got a Story? Share Your Hot MILF Experience

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Some Stories Are Meant to Be Heard

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