When I was younger, I had this thing for a girl in our friend group. We spent a bit of time around at her house so the family got to know us as well, as a result we were friendly with her single mum and older sister too.

Years ago, I tried to get her to go out with me but struck out with her. Wasn't to be and things dwindled out. Eventually, the group stopped spending as much time together and broke away, the usual thing when you're a kid and start to get older, different friends, education paths, etc. Still, we were all on each other's friends/following lists on social media. Some of us were even still friends with her mum and sister on there too.

Fast forward to a more recent time, I was out at the bars one night, weather was quite pleasant for Scotland so it put most people in a good mood. Hot and sunny weather always gets me going as well. I'm there with a few friends. As you do, I scanned the room after we got a table and went to the bar. I spotted the girl's mum, gave a wave and made a mental note to check in with her later when passing on the way to the toilets if it looked like there was an opportunity for it.

The mum, we'll call D, was early to mid 50s, still pretty trendy, wore whatever she could get away with at that age and not look too out of place. She was a thick older lady, dyed blonde hair and tried to keep up with the younger generation. Very attractive for her age, could see where her daughter got it from too.

Turns out I didn't need to wait as when I went to get more drinks, she was at the bar and we caught up for a bit, probably longer than would be normal. I took the drinks back to the table for my friends then went back up to the bar to talk to D. Caught up with what's been going on, giving her a brief overview of my journey since the last time I was at her house as a member of her daughter's friend group.

I eventually broached the subject of her daughter and tried to gauge what she'd been up to in the years since we all grew apart. Distance and time had got in the way and neither of us had kept up with each other - social media use of course dwindles as our generation gets older and more private. Turns out she was doing well these days, and I made mention that I used to have a thing for her when we were younger, tried to get her to go out with me but failed, and had made peace with that long ago. A little gentle teasing from D followed and how heartbroken I must have been as a young 'un. Some light banter back and forth and I tell her I'm glad it didn't work out, with all due request, as we'd both been on different paths that wouldn't have happened had I got what I wanted. I left her to it to let her get back to her own friends and said it was good to catch up with her now I was more mature and grown. I returned to my table and enjoyed the evening some more.

An hour or so later, I see D leave, give her a nod and a wave and think nothing more of it. Sure, my friends spent a good five minutes grilling me about the milf at the bar that took my attention for a little bit when I got back but I shrug that off as banter between friends. After waving to her as she left, the grilling started back up again when there was a lull in the conversation. Ribbing me, saying they bet I've wanked off plenty to her when I was younger, probably even more recently than that too since I still had D on Facebook. Especially since I used to fancy her daughter. After several minutes of denials, I eventually want it to stop and admit to it, I've rubbed many a load out to her. A few times in the last year, I've found a good video of a thick blonde milf and pounded my fleshlight imagining it was D. A sense of satisfaction came out of them as they managed to get me to admit it. "A filthy fucker" and "dirty cunt" is what they labelled me. Can't deny it, it is what it is!

A little bit more libations and they've awakened something within me, and I briefly toy with the idea and hitting D up on messenger. Can always blame the drink if it doesn't pay off. Doesn't take much to get me to get my phone out and compose a message to her. I typed out a message saying it was good to see and speak to her again after years and was sad to see her leave early. Enough room to keep a conversation going, slight flirty vibes in there, but still enough space to leave it as it is if need be. A back and forth starts up and I let her know she was looking well and wish that she'd have joined us instead of leaving and she responds by saying she wasn't totally ready to leave yet either. This is where I decide to shoot my shot and tell her I can get a taxi up with some bottles and we can keep on drinking. A nervy few minutes followed before I got the reply saying she'd be up for that. I ran it by my friends to see if they'd be okay with me leaving and unsurprisingly, they had no issue with me taking off.

Turns out she still lives in the same house as years before, I let her know I'm on my way, made a quick stop off to my house to pick up a bottle or two, then straight to her house. I ring the doorbell, she answers still dressed in what she had on earlier and lets me in. The house had had some more recent decorating work done, a lot more modern than years ago. I made comment of how good it looked before sitting down in the arm chair in the living room and she sat on the couch. Asked her which of the bottles she wanted to open first or if she already had something. She chose, I poured, passed her the glass and sat back down.

To be continued...