A tough confession to help your friend
Pretty-Kelly said:
maybe your friend is just saving his self for marriage. I think that it is nice to see a male a virgin at this age.
Sweet thought, but not practical. In real life, few women want to date a sexual Forrest Gump, much less mary one.
Tonyandretti, you can't try to arrange this behind your friends back. Assuming he actually
wishes to lose his virginity - with a woman - I presume you are sure of this - he's probably so psyched out and intimidated by his own inexperience that he will sabotage and back out of something that appears spontaneous.
You must be frank and tell him that he needs to get this done. Remember learning to drive, or learning to use a computer? It was nothing "special" , but a matter of learning a life skill. Just as he had a driving instructor, a copmuter teacher or a math tutor, he should also have a
sex facilitator / deflowerer.
I am speaking from personal experience. I was in such a situation - and if it was tough for me at 23, it'l be tougher for your friend at 28. I waited for the "right time / right girl" instead of being practical.
Big mistake. She was hot, and experienced. I beat out guys who were better looking and more successful. First couple of times I scored big with the oral - intuition & natural talent I suppose - but after that, when I couldn't keep up, it was a major letdown for her, and a crushing humiliation for me. She had shown her slutty, needy side to a guy who didn't know what to do with it and left her frustrated - she felt foolish and grew to resent me for it.
These days, a woman in demand of his own age will be experienced, and not shy about insisting on her own needs being met. I know many such women couldn't fathom the thought of their bodies being used as a "practice dummy" for a novice. Your frind risks getting a bloody nose from which he won't easily recover - and he's running out of time.
Get a pro who's done this a few times and tell him to approach it like a doctors appointment or a personal training session. Let him get acustomed to it without a relationship on the line, without the preassure to please or to keep face. No, it wont get him caught up overnight or teach him to handle the excitement level of being with someone he cares about - but it's better than nothing, believe me.