Don't get me wrong she's somewhat attractive, she's got some sex appeal going on. But not someone I'd ever consider dating.

RustledJimmies, funny you ask. I do/did masturbate fairly often. Probably once a day. Is that what you're saying is giving me some sex anxiety you think?

I've had quite a few tail come along and I know if I tried and could keep it up I wouldn't be writing this, but I think I'm too picky for my own good at times and then when I find a girl I like my game is worse because I feel like a loser who hasn't / doesn't really know how to have sex.

Haha, hell yea, that should put things into perspective. I honestly don't get why virginity is a big deal. For me, I lost it to someone I met on the internet but was interested in her before she knew and she wound up my fiancee about a few months after.

Haha that's awesome!

I'd say you need to ask yourself two things:
1. Is virginity really THE thing that's fucking up your game? If it is, then sure a less attractive woman or even a prostitute might help you get the giggles out of the way so you don't blow it with someone you're really into.
2. How bad is she that you need to come to a forum to justify it? Is she a stereotypical talk show single mother with everything that entails? Or is she just not quite your dream girl?

If you can get numbers and have a good time with a chick you're into and the only thing missing is the f-close, and if she's not gonna get you shot or have her kid walk in on you guys, sure go for the like a bandaid approach, one motion and done.