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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 Connection with a Neighbor
I had a few experiences with a guy in the early 2000s and then hung it up for a while to concentrate on life and work. I'm married and happy and not attracted to men in particular but always

Posted by a straight man

By vbfordiscreet

Unexpected Bonding at Bob's Party
Straight for gay. MNF at Bob's part 3. After I swallow Bob's load he looks down at me and smiles. He says now I have 2 bitches and you guys will do whatever I tell you. I feel guilty with

Posted by a straight man

By Chris

Unexpected Meeting at Home Depot
Part One - Shopping for Cock at Home Depot. I'm a tall, masculine man who got introduced to soft cross dressing by an ex a few years ago. She liked me to wear panties while I fucked her and

Posted by a straight man

By lightsleeper

An Unexpected Visit at Bob's House
Straight to gay. MNF at Bob's part 2. They I hgo over to Bob's house not really knowing what to expect. But I was definitely curious and had jerked off a lot thinking about Tim sucking

Posted by a straight man

By Chris

A Surprising Encounter at the Neighborhood Barbecue
Straight to gay. My neighbor Bob. As a young teen I had a friend I had jo with a few times. Never went further but left me curious. Grew up, got married, suburbs, kid and another on the way. I was

Posted by a straight man

By Chris

Unexpected Encounters at the Neighborhood Barbecue
Straight to gay. My neighbor Bob. As a young teen I had a friend I had jo with a few times. Never went further but left me curious. Grew up, got married, suburbs, kid and another on the way. I was

Posted by a straight man

By Chris

Discovering New Connections in Unexpected Places
For many years, I thought of myself as totally straight Then the wife lost interest and I went online looking for women. Some great escorts, but not much in the hookup department. So I was online

Posted by a straight man

By hoog7515

A Surprising Encounter in the Park
I just had a guy email me at bikerart2343 That he had saved my email address and wanted to know why. I ans. back because he liked my cock. He then ans. and wanted to hook up and what I wanted him to

Posted by a straight man

By Guilly

An Unexpected Connection at the Theater
I’ve always had guys sucking my cock and watching them swallow. It started on a beach when I was 20 and after a few years with the same sucker he moved away. Then I found the arcades with

Posted by a straight man

By kenhenderson1959

An Unexpected Encounter at Lowe's
Never happened to me before. At Lowe’s this morning to pick some things up. Had to use the head, too much coffee. I go to use the urinal and there is this younger (mid 20’s) worker

Posted by a straight man

By janderhead

A Night of Regret in a Hotel Room
Story about the time I chickened out and always regretted it. So I just graduated college, I was still 22 (im 28 now) at the time and was staying downtown for a new job training. I would have a glass

Posted by a straight man

By yakkity_yak01

An Unexpected Connection in DFW
I am an older black top guy and I met a bottom gay Hispanic guy who gives the best head to the point of me being multi orgasmic. One day I wanted to try a little more so I was on top kissing him and

Posted by a straight man

By jushiden

An Unexpected Visit from the Delivery Guy
I am a Bi 65 year old MWM, who has enjoying playing with other guys for most of my life. I started with a couple of close friends at a very young age. As I got older and the girls started paying

Posted by a straight man

By handsome14u

An Unexpected Connection at Home
I was a straight male, 5’7”, 150lb, 25 years old He was a top, 6”, early 40s, and 7 or 8” My first doublelist hookup was a man who had been divorced recently, neither of us

Posted by a straight man

By Evan

An Unexpected Visit to a Divorced Guy
Have been super horny and tired of jacking off. Have been trying to connect on here and finally got a good reply. Another guy that is recently divorced wants to take on my hard cock. He is hosting so

Posted by a straight man

By downwith

An Unexpected Twist During a Massage Session
I am a straight male, well I can probably say bi. I enjoy playing with guys every now and then. I have a regular that I enjoy seeing. When I go to his place he has me lay face down on his massage

Posted by a straight man

By bballs1

Unexpected Connections on a Business Trip
This was about a year ago, I was on a business trip for work. I’m a normal married white straight guy. Never had any contact with men but to be honest I have checked out a cock of two online

Posted by a straight man

By Anonymous

Unexpected Encounters During a Florida Getaway
Just a few things to get out of the way first… I’m 65 years old. Married and have been dicking around with guys on the side for a very long time. And no. She does not know. Flash

Posted by a straight man

By daddyfurfun

An Unexpected Evening with a New Friend
I was bored one day and wanted to get with a CD, something iv always wanted to do so I found one in the area we chatted a bit and I was invited over that night. I was nervous but when I got there he

Posted by a straight man

By nsahookup90

Finding Freedom and Self-Discovery After Divorce
I had been married and in a sexless marriage for 15 years. I had met a few guy over the years. But it was far inbetween and that was just to get sucked off. My wife asked me for a divorce on a

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 81.3k 1.4k 3.3k
#3
KestrelElbow9092
Gay Straight for Gay Straight
Careful what you wish for. 27.1k 373 3.1k
#4
cnysub
Gay Trans Straight
Gay Bar Show 49.9k 557 2.9k
#5
kimorafoxxsexycd
Couple Gay Trans
My gf got adventurous 79.6k 1.1k 2.8k
#6
sissyjamie4daddys
Trans Couple Straight
I love water 49.4k 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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