Hey man, I’m in the same position. It’s been a long term play, going on years now. Covid ruined my plan as I haven’t seen her since 2020, but was making good progress.

My friend doesn’t live with her anymore (we’re 32, she’s 50). But she has other younger kids in their teens that live there. I’ve been flirting with her for years, but most recently the last time I saw her (start of 2020) I was round at her house one night to help her with her phone (I used to fix iPhones as a job), and I had pre-prepared some dick pics on my phone. I was looking at places to move to at the time, so I saved a bunch of pics of apartments, and then added some strategic dick pics before them in my photo reel (the ones where my dick looked biggest), and let her flick through the apartment pics while I was working on her phone. I couldn’t see my own phones screen as she was flicking through it behind me, but I knew the moment she hit the dick pics, as she stopped what she was saying mid sentence and lost her train of thought. As it happened, I excused myself to the bathroom and left her alone with my phone for a few minutes, to let her get a good look. And also I needed a minute alone to compose myself as my adrenaline was pumping. I was freaking out a bit wondering if this was all going to go wrong.

When I came back, her phone was on the table and when she went to pick it up I swear she bent right over the table and stuck her ass right up at me as though she wanted me to rip her leggings open and fuck her then and there. I was a little taken aback that this worked so well. I couldn’t do anything because her other kids were running round the house. I went home a few minutes later (and got a hug on the way out). But I could tell I left a lasting impression.

I haven’t been able to do much outside of text her sporadically due to lockdown etc. but she’s still very receptive with my flirting in texts. Some other logistics have stopped me meeting up with her again yet but I’m trying to figure out how to make my next move.