Hey Zip. Thanks for all the help.
Ok, so I have a good girlfriend who I've known for like 15 years (we dated in 6th grade

). She told me a while ago she is still a virgin. She is 24. We lost touch for a few years when I left for college, but for the past year or so, we've been hanging out as friends when I make it back home to visit. We chat over the internet back and forth occasionally and I've steered it slightly sexual from time to time, but its always in that "friend" sort of way. Playful or whatever, but then switch to sincere, pretty much cus I DO want the low down!
So... I am the front-runner basically. Shes kinda hints at the type of guy she wants to do it with (my type), but its her first time! I feel bad for her cus she thinks about it ALL the time,. Its becoming obsessive. so in a way, i want to help; she is my friend and I care about her. If it wasnt such a big deal to her, hooking up with her wouldnt be a prob. She needs to get over this.... speedbump(?) tho. But part of me is like "No Way Man! That has Pandora written all over it!" I had a serious relationship with one of her best friends in hs, 2 years. That girl however is engaged to some other dude, the guy she dated after me.
The gossip concerns me way less than the friendship that would take place after the thing. Also, i dont think I can be honest with her about the number of girls I've been with. She wouldn't like that... What do you think??? She definitely needs to get laid. But she has this outrageous criteria, I understand cus its her first time, but the girl needs ass! Should I? She is depriving herself or normal sexual experiences, she is almost 25!
I know I missed this one, and the situation is probably over and done with... but hypothetically and for the future...
Don't kid yourself and justify your desire to sleep with a virgin as "helping her get over this speedbump." Taking someone's virginity should and is a big deal. For everyone involved. And if she's engaged... I'd stay out of it. And you'd HAVE to be straight up with her about the number of girls you've been with (because it's her first time... she has a right to know. Honestly... a high number won't be a bad thing... it will trigger some attraction, fyi.)
If you're worried about the friendship that would take place after... it will get fucked up. We all are somehow attached to our "first," and not in a good way. As a friend, stop justifying it by "doing her a favor," let the girl have sex with her husband when they are married.