Why not just get a beautiful prostitute?
Yeah I was gonna suggest that but it might set his standards too high.
Maybe web dating, there gotta be a virgin section.
Maybe church.
But yeah the first time is weird. I was like ten if we are being honest. I repressed it until a few years ago but it was in the back of my mind and I finallly talked to the woman and she said yeah we did. It fucked my head up and I thought I was a virgin and was embarassed I was a virgine even though I wasn't.
I am being honest and this is not something I am comfortable elaborating.
So yeah my second time which was when I fucked after puberty was like 16 or 17 and it was an older woman who was 40 but really fucking hot. I went their to sell some blow to her son. She invited me for some drinks, we did some lines, she blew me, then we fucked. She was like that was fun, don't come back here again and sell my son drugs, this was wrong on my part.
I dunno, I took a chicks virginity and I hated it cuz she acted like it was the ultimate gift and she sucked at sex and didn't get any better but she was cute and nice so we dated about 4 months.
I really suggest fucking a prossie. Then find a nice shy girl cuz you sound like a shy guy. I never turned down sexual favors from someone I was attracted too until I got over the whole prepubescent sex thing cuz of how it went down and I will not elaborate as to why. So like 13 I started gettting bjs.
I was getting handies in grade school though on the bus with various girls and fingerbanging them so I guess I just had a two year spell of sexually fucked up in the head time. My fucked up shit in my life has nothing to do with your problem.
So yeah after having sex the first time after puberty, within a year I was very promiscuous and it kept going like that till marriage and then my second marriage and after that it got out of hand and I took a break for a few months and then started sleeping with my first wife again. That was recent but I just like always had to be sleeping with someone or I couldn't sleep at night or in a bed. Once again thats my hang up.
Anyways get it out of the way with a prossie. Get a proper escort service and get an all nighter cuz you gonna cum quick. So you want to tell them you want to fuck all night. It will be totally worth it. It is not hard to learn. It isn't hard to get good at it. It is best to do it with someone you won't ever see again at this point.
After that try dating, maybe online or ask out someone who flirts with you. Good God I don't have time to get into all that. I might make a sticky cuz I feel like I am answering the same questions over and over.