Brittney, I understand how confusing it can be for you when male friends get physical in a sexual way, and especially if you find that it somehow is pleasurable. I only want to say one thing: friends and lovers are two very separate categories. Lovers usually begin as friends, but when the relationship changes again, they almost never return to being friends! So, you have to choose your partners on the basis of your attraction to one another, your trust and deciding whether this can be a benefit to your relationship, or if it will be something to regret. If you know that your friend is a good one whose company is important to you, bear in mind that changes to the status quo could perhaps cause you to loose this. Did you ever feel attracted to him before? If so, it might be that your friendship is evolving into a romantic relationship, where different emotions come into play. If he is known to be a 'player' (I am not american, so I don't know what that means, but I am guessing that he does not respect the feelings of his girls and is interested in a strictly sexual thing) and you can not risk the heartbreak of being played with, think more than ten times before you do something that will change things so much for both of you!
Also, speaking as someone who is older than you, (40) I'll give you some motherly advice you don't want! Since you are virgin, don't forget the importance of birth control. It will make things much easier on you if you choose to be very in control on this matter. I don't know if you have access to this, depending upon where you live and what sort of relationship you have with your mother or friends, but please, think about this aspect. When I first started to become interested in the guy who eventually became my first partner, I decided on my own to go on the pill, whether or not the relationship evolved into something sexual. I needed the peace of mind and sense of security.
Sorry if I've bothered you with advice, but you seem like a nice person who is sincerely seeking some advice, and if I have been a help to you, I am happy.