F(40) Talking to an older (59)M, Unsure of His Intentions

I am 40 and I met this 59-year old man in my pickleball group (we play three days a week, for about two months.) He's been flirting with me on the courts but we hadn't had an actual date. I was at a Halloween brewery event and he offered to join me for a drink, so we chatted at the brewery, and it came out in the conversation that I'm a virgin. He said that kind of innocence is cute.

Now, we only started texting right before Halloween and he doesn't like texting, so he's called me a few times, and he is always saying or implying how he could be a teacher for me, talking about how not many men know about "women having pleasure 30min while men only seconds". He's telling me how he's this experienced lover and puts it like he's doing me a service teaching me those things. I've told him multiple times that I don't do casual relationships or anything like that, that I want to get to know someone before getting intimate, etc. The other day, he texted me a photo of himself, he said to test my modesty. It was a naked photo with his genitalia covered with a yellow highlighter box, as to censor, but it was somewhat transparent and didn't cover fully either.

I wondered if he was attracted to me, but he hasn't asked me on an actual date. I'm confused and it seems a bit creepy. The other day, we were talking on the phone and he told me how I wore spandex on the pickleball court and he noticed my legs and butt, and he said like he was giving me lessons that I should be dressing a certain way if I want to attract men. Like, not wear a baggy tshirt, etc. He doesn't even know me. It was upsetting to hear, messed with my self esteem.

And, today, after play, he drove me in his car toward the parking where my car was parked, cause he said it was safer than me walking through some bushes in the dark. And, as we sat there he went on about if I had ideas on what I/we should do to "pay" him for his "service in teaching me" (not actual money payment), do I want to go home alone or shower with a man instead. Not suggesting the actual intercourse but still talking intimate. Anyway, I said good night and left the car.

I'm really confused on his intentions and it's just weird. Any help? Thanks!

TL/DR: Female (40) talking to male (59), met playing a sport, he's always making intimate remarks and offering to teach her in intimate ways, and she is confused on his intentions. Any help?

Submitted November 11, 2022 at 06:17PM by serenlyn https://ift.tt/JnavZ57