The Elusive MILF

Stacy’s Mom surfed the internet for high school boys.

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Jeanine_Reunion_01It was less than a month after I turned eighteen. I started looking to do something like this when I was somewhere around 16, the Fountains of Wayne song, ‘Stacy’s Mom’ playing in my head. The day I turned eighteen, maybe the day after, I made myself a dating profile on an “adult” dating website advertising casual hook ups.

I put a great deal of thought into the profile. I decided what I was looking for in an older woman, and I took some rather risqué pictures of myself, to put on the site. They are probably still there, props if you can find them. It was quite the endeavor. In fact, I did not even have a debit card at the time to pay for the profile so I actually had to take a trip down to the 7 Eleven in town to buy a prepaid debit card to sign up for the site with. After making the profile I sat down to find what I was in search of. The elusive MILF.

After about a week of scavenging through local profiles, I found what I was searching for. A woman located just about an hour from me, 38 years old, in a messy divorce, with a 7 year old son. She was a good-looking woman, kind of like Kristen Stewart if she was in her late thirties. I sent her a message.
“Hey I’m Tony, I would love to fuck your brains out.” Her response:
“Ha ha how about we settle for some good sex instead. I kind of use my brains.”
Emails were exchanged, followed quickly by cell phone numbers, pictures, and sexts. A plan to meet was established. The only problem was on my end. I had to somehow establish a story to tell my parents in regards to where I was going to be that night and when I was going to be home. Especially when you take into account my whereabouts on the previous Halloween. I decided I would take the trip up to the Massachusetts border to spend a torrid night with this older woman, let’s call her Lisa, on the night of a high school function. Afterwards, I would be ‘spending the night playing guitar hero at my friend TJ’s house.’ He graciously went along with the plan, should anything happen to me and I not respond to his texts he would be giving the police Lisa’s address.

The fateful night came along and I was ready for the fourth sexual encounter of my life to begin. First I had to make an appearance at my high school’s Mr. High School mock pageant. It was a yearly tradition at my school. Some of the more outgoing and popular guys in the senior class would participate in a beauty pageant. It was actually one of the more interesting events that happened at my school. Obviously I had other things on my mind. I sat down in the audience, my parents knew not to expect me home and TJ knew I was going to be leaving to meet a woman. After half an hour of boys lip-syncing pop songs and giving silly speeches, I was out the door and on my way to meet Lisa at her place.

I pulled into Lisa’s dirt driveway and gave her a call.
“Hey I’m here,” I growled into the phone, trying to sound older.
“Hi, um, I’m gonna need you to climb in the window, my roommate is home.” She whispered into the phone.
“Well ok, sure.” I walked slowly up to the one story house, snow up to my knees, trying to find the right window. I peeked in and saw a very large, very ugly woman lying in bed. I stood there trying to decide if I was going to knock or turn around and run, I mean hey, I had already driven the hour up there and this woman definitely looked like she could have given birth to a child. As I leaned forward to knock, a window to my right opened and Lisa stuck her head out.
“Hey! Over here.” I let out a deep breath. Thank god. I crunched through the snow to Lisa’s window, and climbed in.

I took off my faux fur coat I had been wearing, because yes, I was ‘that’ guy in high school, and sat awkwardly on the edge of her bed.
“Do you want to smoke?” She pulled a bag that must have had at least an ounce of weed out of her dresser.
“Sure.” She rolled a loose joint as we spoke in whisper.
“So how was the ride up here?”
“Not too bad at all.”
“I like your coat.”
“Thanks … So your roommate is in the room next door?” She laughed, raspy and beautiful.
“Yes, I’m glad you didn’t knock on her window.” ‘I’m glad you weren’t her,’ I thought to myself.
“Me too.”

We smoked the joint, and she put a hand on my leg. I leaned in and kissed her. She took my shirt off. She was in pajamas with no bra on. I took off her shirt and kissed down her neck. We continued to undress and kiss. She held me in her hands, gently and with the experience that I had been hoping to find. My hands were shaky. She guided me and showed me what I should do. I kissed down to between her legs and started licking. As she guided me through my first time providing oral I must have been doing something right. She moaned and pulled my head in towards her. Then suddenly I felt a gush of something hit me in the face. I jumped halfway off the bed. She started laughing.
“Sorry, I probably should have mentioned that I squirt.”
“You what?”
“I squirt when I cum.”
“Oh, well that’s ok, it just kind of startled me.” I was definitely going to Google whatever the fuck that was when I got home.

From here the sexual activities proceeded in a usual, if slightly wetter, manner. Until one point about an hour in when she stopped me.
“I want you to fist me.”
“Um, you are gonna have to show me how that works.”
“Of course honey, oh and put on your coat.” So there I was, barely eighteen years old, fisting a woman I had met an hour before, in a fake fur coat while she squirted all over the bed and all I could think was, I am going to need to come up with a really good explanation for how we met for when I tell all my friends about this.

The sex continued for about another hour, during which anal beads were introduced and I was taught a great many things about the male erogenous zones. Eventually I left her, naked and exhausted on her bed as I climbed out the window, in the fur coat with my shirt tucked under my arm. I slipped into my car and made my way home. As I pulled onto the highway I got a text.
“You were amazing, we have to do that again, next time I have another guy who can join.”

On Monday sitting at lunch at school I told my friends the story I had concocted to gloss over the fact that I had met Lisa, ‘The MILF’ as my friends would come to call her, on the internet.

The story went as follows. I would go over to my mom’s tennis partner’s house to split logs out of the trees she had cut down in her back yard. She was going through a divorce. I gave her my number so she could let me know when she had more trees to cut down. At some point she drunkenly texted me asking if I thought she was attractive. I said yes and after a bit of talking she invited me over to have sex.

I stuck with that story for years and I’m sure to this day some of my friends from high school still think that’s how it happened. I think I kind of like the real way better, but maybe that’s because it really happened. So to all the high school boys out there, who want to fuck a MILF, do it. She’ll teach you some things that you will want to know in College. For instance what it feels like when someone squirts on your face, and how exactly to fit your fist inside a woman.

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