Author: luckyfriendsexymom

Reminiscing about holiday visits with my friend’s mom [MF]

(I have several older posts if you’d like a more thorough backstory on everything, but to sum it up: I had a many-years long sexual relationship with my friend’s mom that started over a decade ago and has sporadically continued until fairly recently, including a couple of meetups with my now wife and Mia (the friend’s mom, and how I’ll refer to her from now on). We haven’t seen each other in a while now, but chat once in a while and usually end up reminiscing a bit about past encounters we’ve shared, which inspired this post!)

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Wife and I spent the night in a hotel with a longtime MILF friend of mine [FFM]

I’ve posted several stories on here before, but I’ll try to give a quick breakdown of what led to our experience this past Saturday.

My MILF friend (54), let’s call her Mia from now on, and I (33) started a regular sexual relationship about 15 years ago. I went to school with her son and we would hang out occasionally but eventually just drifted apart. To my surprise, his mom was always willing to chat and text with me. We were both clearly attracted to the other, and before long we were pushing the limits of where our conversations led. I hadn’t even really wrapped my mind around where this was all heading by the time we met up after class for the first time. Our little fling built into a pretty intense thing, but had its ebbs and flows as we both moved around and our lives took us different directions. Until Saturday we hadn’t been together in about 4 years, shortly before I met my wife. Read more »

A night at the hotel with my friend’s mom. (M/F)

It’s been a while since I posted one of our stories, and since I had some time today, I thought I’d write out another one for you guys. Hope you enjoy it.

We’d been having sex pretty much as often as possible for almost a year, but almost always under circumstances where we couldn’t really let loose on each other and try new things (or really make much noise, when it came to us sneaking around while everyone else slept). What we’d been doing was fun and exciting, but we wanted time alone to really enjoy each other without distractions.

We decided on a day, picked a place in a nearby town, and it was a date. We talked all week about what we planned on doing to each other, positions we wanted to try, places we wanted to fuck, where she wanted me to cum, where I wanted to cum. All that resulted in us both being too horny to hardly function in the days and hours leading up to the rendezvous. We messaged back and forth all day, the day of, and I couldn’t get to my car fast enough after my last class of the afternoon. She messaged me on the way that she was already there and gave me the room number, which immediately made me hard. Read more »

Late night encounters with my friend’s mom. (M/F)

I’ve mentioned before that, even though we were only 18/19, she was ok with us drinking at the house as long as no one drove away drunk. They had a basement that we could pretty much go ham in on the weekends. Naturally, we did that often, leading to numerous occasions where we’d manage to sneak off while everyone else was preoccupied partying downstairs or late at night after everyone had passed out.

One particular night, a friend had picked me up from u/miamya1’s house so we could take a little road trip (smoke a bowl). Everyone else had been talking about going to another party that night, and somewhere in the time I was gone had found a ride and moved en mass to the other side of town. When I got back I was good and stoned, as well as pretty drunk, and wondering where the hell the party went. Miamya explained they’d all left, and that she would take me to the party if I wanted to meet up with them there. But we both had slightly different plans for the rest of the evening. Read more »

Working for my friend’s mom (M/F)

u/miamya and I really enjoyed the pm’s and comments from last time, and thought we’d share more for you guys to enjoy. There are plenty of other after school stories at her house to tell, but I thought I’d shift into the next kinda phase of our time together: Working together, sometimes alone and for long periods of time.

For a few years after her divorce, she jumped around several jobs before finally deciding to open up her own business selling boutique furniture from a small shop in the city’s then shitty and desolate downtown. Unlike many of my close friends, her son included, I stuck around town to do the local community college thing after high school, which I wasn’t particularly thrilled about at first, but it turned into a quite the job opportunity for a 19 year old taking 12 hours in community college while living at home.

After calling me numerous times over the course of a weeks or two to come help her move furniture around the store, she decided to hire me at the shop (to my delight). We had been fucking off and on since that first time after school at her house (and yes, once when she’d called me to move stuff around the shop), but this was to become something different. Read more »

After school with my friend’s mom: The first time. (M/F)

I’ve told some of these stories on here before, but it was years ago. it was a dream come true type of situation, which could make it hard to believe for some. But this is my stamp of truth that the following events did occur, for what it’s worth. And if it helps, u/miamya herself will be joining the comments to answer any questions.

If you’re not interested in the events that led up to our first time together, just skip down to the ***** for the nitty gritty.

MY friend’s mom and dad had been going through some rough times. He was out of town constantly, and always being shady about how long he’d be gone, what he was going to do, and so on. She was just plain unhappy, and he was too. The summer before my senior year she filed for divorce and that was that.

Somewhere in the year or so before that, she and I had started talking on yahoo/msn messenger (Yeah, it’s been a while now). It started off simple enough. She was always the cool mom who would let us drink at the house, since we’d go out and do it somewhere else anyway, and make sure no one drove. And she was easy to talk to, drunkenly late at night, or sober the next morning over breakfast. Read more »