TJ First timer, 38yr old virgin

So my buddy from high school has had a rough go in life. Beyond some real tragic childhood shit, things have not gone his way as an adult either. Long story short he’s now a 38 yr old virgin with little income living with his dad. He has a told me now he doesn’t care how, he wants to have sex. Well seeing that I am divorced and have plenty of disposable income, I bought us both plane tickets to San Diego and reserved a room at Cascadas where the plan is for him to finally achieve his goal of having sex with a woman lol.

I have never done such a thing but figured fuck it it seems fun. He is a bit overweight, obviously very low confidence and is sober from alcohol. I am afraid I am not the best guide for him. Any tips on how to make his experience as good as possible for his first time? Should we tell his girl he picks thay shes his first?