I've been hooking up with my friend for 2 months now. 'friends with benefits"-if you will. He's a virgin but he's difficult to figure out. We do pretty much everything but sex, I'm pretty sure he wants to. I know he's shy but he's very good at hiding it. How do I do it? Do I ask? Do I just go for it? What would a guy want to remember?
Defining virginity depends on your definition of sex. To me passionate kissing is sex and can be more intimate than intercourse.
Communication between the sexes is one of the largest missing aspects of sex and relationships for us. We can't get into conversations about it because we have been taught that it is wrong to do so and we get all weird when we do or we turn into 12 year olds about it.
My suggesting is to be very mature about it and simply ask him. He may have his reasons for not wanting to have intercourse. He may be scared and unable to admit it. Just ask and find out what he is looking for.
Also, as part of a pre-sex discussion find out what having intercourse will mean for your relationship. We all have different ideas of what a post-sex relationship will mean.
You ended that question with an unusual question.. "what would a guy want to remember?" To your main question, probably just go for it since you've been doing everything else. He may think you don't wanna do it and is too shy to ask. Just go for it as if everything was ok and see how it goes. If he gives any resistance, then that'll open the door to talking about it as long as you don't go for broke. Just make moves on him in that direction and see what happens.
Sometimes shyness is not so much about doing what with who as it is where. There could be fear of being discovered in the act by authority figures. Some things people don't realize they can get arrested for depending on the state where you live. If he's working toward a certificate to teach middle school and imagines his name in the news for indecency, that can be scary. Try to create a very relaxed situation and maybe he'll loosen up.
Just do it. Blow him to get him on his back, hard and lubed, then hop on board, cowgirl-style. If you want him on top of you (providing he holds out for more than a few seconds the first time), you can initiate the roll.