Loss of V card, is it really that much of a deal?

Im 20 soon to be 21 never did me and my boyfriend entirely had sex, i guess i was too afraid of whether it would hurt or not plus he was a virgin too and had much less of a clue than i did, now a guy I've liked for like a year is good friend of mine and asked how I'd feel about a free, he knows im still a virgin, and I'd be up for it if I weren't although im now afraid that i want it because i might have that silly crish on him yet again. On the other hand i know i can lose it to a great old friend who im sure will keep it quiet and all... But I'm really torned, what should I do?