Jelena

A couple of days after Megan and I had our first hookup, she invited me to a late night bowling session with her and some of her friends. But there was a slight problem: on that day, she was working on a flight back from Paris which got delayed, and so she couldn't make it back in time for the night. I was thus left alone with a group of people I barely knew. Thankfully, they were all mostly pilots or flight attendants, which meant that I at least managed to strike a conversation with some of them.

One of those was a slightly older, petite woman named Jelena. Unbeknownst to me at the time, she would soon become the first Milf with whom I'd go home that night.

Jelena was a whole decade older than me, putting her in her late 30s. She also had a kid, though her body would have never indicated such, as her slight, 5'4" frame probably didn't break triple digits in weight. Despite those stats, though, her features were amazing, even under her clothes. Her breasts, undoubtedly aided by her previous childbearing, were large and supple for her frame, practically bursting out of her tight, low-cut, pink top that night, and her ass was perfect and round in her blue jeans. Her face was very pretty as well, complete with bright blue eyes and a mouth that I knew would look good around my cock. Her hair was light brown and reached her shoulders, where it curled out, framing her face nicely.

Going into that night, I would have never entertained even fantasizing about a woman much older than I, but once I started to get to know Jelena, I knew I'd be beating off to the thought of her that night - that is, if the stakes hadn't risen like they did. You see, a couple things I learned about Jelena right away were that she was very outgoing and exceptionally sexual. Also, for whatever reason, she took an instant liking to me. All of those things came into play to lead to what would be a night I will never forget.

Jelena and I hung out at the bowling alley for most of the night, telling each other about ourselves, how we knew the friends we were with — or in my case, without — that night and occasionally just goofing around. She was sort of a mentor for Megan when the latter was just starting her career, and they had remained close ever since.

I also found out that this night out was kind of a goodbye for Jelena, who would be leaving the company in a week to return to her hometown in Hungary. She wanted stability and to spend more time with her kid, especially since she was a single parent, two things that working as a flight attendant couldn't offer.

The twist finally came when Jelena asked me if I was single. With nothing of which to be ashamed, in my opinion, I told her I was and confided just a tiny bit to her about my present personal situation. She asked me if I had been spending time meeting other girls, and I confessed about the current state I was in with Megan.

"Well, if you're good enough for Megan, then you're good enough for me! I've seen that girl pick her men, she is much more meticulous than she lets on. I'd definitely be down to confirm this hypothesis if I weren't moving away!", Jelena said instantly.

"Well", I said, without really considering the implications of what I was saying, "that's a whole other week away." For a flickering second, I saw her eyes light up with a burning passion, before a grin started creeping across her face.

"That's true...", she said, trailing off as she got up to bowl next. The moment ended there, and the night continued on as it had been so far, except for the fact that now I couldn't stop debating in my head if I would really have sex with this woman or not if I had the chance. Never had I imagined I'd get the chance to sleep with a woman who had a kid, but she was a dead sexy milf, and any number of guys would be proud to bag her, mom or not. This back-and-forth warred in my mind right up until I was walking Jelena to her car at the end of the night out.

We had all driven separately, so our other friends had already parted ways. Jelena parked just a few spots down from where I was, so we continued in the same direction until I reached my car, at which point, Jelena hugged me goodbye, told me to not be so down on myself and then continued toward her vehicle. I noticed **** in her departing from me, which, along with the hug and her parting line, I figured to be a signal. In that moment, I was convinced that I could have sex tonight if I wanted. Maybe it was the fact that it was 2 in the morning and not the time of day for my best judgement, but I finally made up my mind.

"Jelena!", I called to her, and she turned around immediately, a smile on her face and her blue eyes staring at me attentively. "Maybe I can follow you to your place?"

Her smile grew wider, and she took a few steps toward me. "Yeah", she said. "Yeah, I live right down the street. I have to get up at 7 for work, but what the hell? I'm only there for another weeek. I can stay up a little longer. Who knows when I'll get the chance to enjoy myself like this with my daughter around, you know? See you soon."