I was listening to this podcast on that subject: https://podcasts.apple.com/us/podcast/swinger-university-a-sexy-and-educational/id1466264114?i=1000668337960

So I asked Jon to tell me about his last sexual interactions (I am an easy cummer, so my examples would run contrary to most stats), and tell me if it was worth it or not (ie as good or better than sex with me). The podcast mentioned the better you know someone, the better the sex is). Here are his answers (he only came once):

• Woman A(known her for 10 years): PIV in the hot tub. 10 minutes, 3 orgasms, felt like maintenance sex. Worth it.
• Woman B (met once before): stimulating her clit in the HT. 5 min, 1 O. Fun. Worth it.
• Woman C(first time): jumped on him in the pool. 10 min PIV, 3 Os. A bit rough. Not worth it.
• Me, another guy and me: Jon added himself at the end of a play on his way to get a toothbrush, PIV 10 min, 2 Os. Fun. Very worth it.
• Woman D (8 years): PIV and anal. 30 minutes, 5 Os. Totally worth it.
• Woman E (6 years): only gave her oral. 15 min, 3 Os. A lot of work, but fun and worth it. He loves that woman.
• Woman F (played once before): extraordinary sexual chemistry. PIV. 30 min, 10 Os. Totally worth it. Now in his top 5.
• Woman G (first time): great sexual chemistry. PIV, 20 min, 5 Os. worth it.
• Woman H (played 3 times before): PIV, 20 minutes, 5 Os. Pillow princess. Not worth it but she is sweet so Jon is ok with that.
• Woman I (once before): Failed PIV, switched to oral. 3 Os. Not worth it.
• Woman J (2 years): PIV, 20 min, 4 Os. Pillow princess. Not worth it. Last time it happened.
• Woman K (second time): PIV, 30 min, 10 Os. Very sensual. Only orgasm for Jon. Totally worth it.
• Woman L (first time): PIV, 5 min, 3 Os. Devoured than Jumped on his dick on the patio. Crazy loud. Broke her no-kissing rule with Jon, in front of her husband and 20 other people. In the top 10 most beautiful Job ever had. Totally worth it.
• Woman M (2 years): Very shy. Pillow princess. PIV for 20 min. 5 Os. Jon only plays with her because I like her husband. Not worth it.
• Woman N (first time): PIV, 30 min, 10 Os. Extraordinary overall chemistry. Incredible body. Totally worth it.

Also, for context, Jon always gives the woman oral first for at least 10 minutes unless the encounter happens in water.

So I think the answer is: there is no such rule as knowing people a long time leads to better sex. You are either good at it, or you are not. And you are good at it if you have a lot of experience.

Also, for context, all that was last weekend!