Almost every day when I get home from school, I go upstairs into my room, put some music on and start doing my homework. Unless I’m hanging out with Jon, or recently, hooking up with one of the neighborhood’s sexy middle-aged women, I just put on one of my favorite albums and get work done. One day a few weeks ago, I was hoping that Janet or Emily or one of the women that I had been fucking over the last few months would send me a text while I was at school that they were around for me to come over when I got out of class. I was just really horny that day, more so than usual. Sitting in Mrs. Robinson’s class, I couldn’t stop thinking about how I had bent her over her desk in that very class room. She didn’t seem to be thinking about the same thing though.
Author: ilovemilfs06
A MILF, a Teacher, and a School [mFF, Str8, anal, exh, oral]
As an 18 year old guy, I usually have a hard time concealing boners wherever I go, but the day of my first swim meet of senior year was especially tough. It happened to take place a little over a week after my orgy with my best friend, his mom, my English teacher, and the two MILFs that I have been fucking for quite some time. I hadn’t had the chance to fuck any of those incredibly attractive older women in the days since, so I had nearly a perpetual boner, which was only soothed for brief periods of time after my frequent masturbation sessions. Unfortunately, I couldn’t just slip away in the middle of school to stroke my dick. I’d have to until I got home after the swim meet to get off. Or so I thought. As I was walking out of English class that day, Mrs. Robinson stopped me and brightened up my day.
A Different Kind of MILF Encounter [Str8, mmFF, inc, pee, anal]
I thought things wouldn't get any crazier after I watched Jon fuck his mom. Boy was I wrong. We were hanging out at his house one day, playing games or whatever, when his mom and Aunt Dani walked in. They came right up into Jon's room and shut the door behind them. I recognized Aunt Dani from family parties. I always thought she was sexy, perhaps a bit slutty, but before I fucked Jon's mom, I didn't think much of it. Now anything was a possibility.
"Hi Mikey, remember me?" she said while biting her lip.
"Um yeah, how's it going?" I answered. Jon was already in the process of taking his pants off. Dani was eyeing his boxers under his pants, waiting for his cock to peek out. I looked over and figured I should follow suit.
"That's right boys, we're going to get particularly fucking dirty today," Emily said as I slid my jeans down passed my knees. I love it when women curse, so when I heard her utter the word "fucking," I got slightly hard. Emily walked toward me and pulled my boxers down before grabbing my dick.
Yet Another MILF Party…With a Twist [Str9, mmFFFF, anal, inc, mast, oral]
“So dude, I don’t want to sound weird or anything, but I think you should hook me up with Mrs. Skye or Janet again. I’ve been going through a bit of a dry spell,” Jon said to me on our walk home from school. I knew it would only be a matter of time until this came up, but since then, there had been a bit of a complication. Not only was I fucking Janet and Mrs. Skye, but I’d also started fucking Jon’s mom, and she wouldn’t be happy if she found out that I had arranged something with the other two without including her.
“Yeah man, maybe soon, but I don’t want people to start thinking something is up,” I responded, trying to dodge the topic.
“Don’t fuck me over man. How can you take the two hottest fucking MILFs around and not even give me a shot?”
“Fine!” I almost shouted at him. I just wanted to end the conversation. “Tomorrow night I’m going to Mrs. Skye’s house with Janet. If you just shut the fuck up, I’ll let them know you’re coming too.”
My Best Freind’s Mom is a MILF [Str8, mF, anal, oral]
It had only been a few days since Janet and Mrs. Skye had initiated my experience with Jon’s mom. I had seen him twice since and he didn’t seem to have a clue. It was a little weird chilling with him after what I did with his mom, but it was totally fucking worth it. Sitting in bed that night a few days later, I made the decision to try to get with Emily again. I knew Jon and his dad were going out of town for a few days to see the local baseball team play a couple of road games, so I figured that would be my best opportunity. John knew what I had been doing with Janet and Mrs. Skye, but he’d probably flip a shit if he found out I boned his mom.
The next morning, I went over to Jon’s house, like I did pretty frequently when I wasn’t in school. We started playing videogames and his mom was downstairs doing laundry. We got hungry, so we decided to go into the kitchen for some chips.
Even More MILF Fun [mFFF, anal, oral, mast]
“What the fuck were you doing in there?” My mom was screaming at me.
“Nothing, I swear to God.”
“That's bullshit and you know it. I could smell the pot and I saw John coming out of there. Janet is going to be pissed that you had friends over there. You know how she is,” my mom yelled at me. When she finished her sentence though, I was absolutely relieved. Sure it sucked about her finding out that I was smoking pot, but she didn't find out about our sex-filled afternoon.
“I'm going to call Janet and let her know,” my mom said, now somewhat calm.
“No, you don't have to do that. I'll tell her.” somehow I had convinced her not to call Janet. Aside from being grounded, I had managed to avoid a sure disaster.
“Alright Mikey, but you have to deal with the consequences. You're going to have to do whatever she says,” my mom said.
“That won't be a problem mom,” I answered.
A few days later, Janet came home and my mom forced me to go next door and apologize. Luckily, she was home alone, because even though Janet was cool with what happened, I'm sure her husband wouldn't have been. I knocked on the door and she answered.