I knew this guy kind of liked me from the first moment I met him and I was kind of interested in him too but my friend told me she liked him before I could even say anything so I decided to be fair and let her try and ask him out first. She did and he said yes. They have been going out for about a year now and this guy has been flirting with me occasionally ever since they started dating...

At first it wasn't that bad, this is a horrible thing to say but I actually enjoyed his complements and felt flattered by the little attention I got from him but lately, I've gotten a little... too much. She will try and cuddle him (she REALLY loves him, I still think they are a cute couple.) but he will look super annoyed and he will in turn say to her "Why don't you go hug on her instead?" He will call me 'gorgeous' and 'lovely' a lot, often times RIGHT in front to his girl!! She doesn't seem phased at all by what he has been doing!

About a month ago I hung out with him and a few other friends while his girlfriend wasn't around and during conversation I hinted that I may be bisexual (which I am) and the boys took that news and ran with it, him especially. Last week he confessed to me that he had a plan to get his girlfriend to make out with me in front of him!! He said it was like "His ultimate goal, his plan"! I was really weirded out by this and he said "Go and ask her about it! We've been talking about it together for quite some time." This weirded me out EVEN MORE because SHE was apparently in on it!

Just last night him and his girlfriend were with me at a party and he started drinking a bit. He was pestering me most of the night begging me to "PLEASE KISS HER!" and my friend was completely docile as if she were expecting me to ACTUALLY DO IT! I also know for a fact that she is straight! This is just a very awkward situation...

Should I confront my female friend about all of this? Should I ask her what she wants? Should I be concerned for her and the guy she is with?

Some straight couples actually like that kind of stuff but if you get involved don't expect anything other than being a third person for the sex only.

If it bothers you I'd leave them both alone. Tell him you are not for that and to stop flirting with you. There is no twist here, just speak your mind. But as Nohelp4u said, don't expect to be anything but a sex toy.
The guy sounds like a creep the way his treats his girl friend, I don't understand why you have continued to hang around him.

I continue to hang around him because he is my friend's (I dare say 'best' friend's) boyfriend. We are all together part of a group of friends that is kind of small and close knit. I really don't want to break them up or speak ill of him to her because she seems to be VERY in love with him and she is such a hopeless romantic. She has nothing but good things to say about him when it's just her and I talking.

I'm not saying break them up, although he sounds like a creep. You kind of played into this. You enjoyed his flirting at first. If this is really bothering you, put him in his place. Otherwise they think you are open to this. You can remove yourself from their company when he is around, that is if this really bothers you and you want to.

Your best friends boyfriend wants to get the three of you together, has been flirting with you, tells you she is game and you don't think you ought to say something to her? How old are you guys?

You only need to be clear about a couple of things: The guy's fantasy is that his girlfriend makes out/has sex with you because he thinks you're the hot-girlfriend of his honey and he wouldn't mind seeing you two get it on. You are NOT someone he is romantically interested in.

Your friend may be going along with this to make HIM happy (fulfill a fantasy) or she may be into it herself and not had the courage to tell you of her bissexual fantasies.

Talk to your friend. Ask her how she's feeling from a loving place. - Is there anything she wants to admit or talk about? How does she feel when boyfriend talks about that kind of thing? If you gauge that the guy is pressuring her or he's a sex-creep - you can't tell her what to do, you can only encourage her to make loving choices for herself. If she let's you know she has the same fantasy... then be really honest with yourself and HER about what you're comfortable with. There's no shame in saying "no I'm not into that."

HOWEVER if you're harbouring some fantasies about "oh he's so cute and I like him a little too - but I suppress it because he's going out with my "best friend" then get clear with yourself and knock off any romantic nonsense you might be harbouring that could not only hurt your best friend but yourself too when you figure out he doesn't really "like" like you. I'd be very careful here since you have some feelings for him too.

It's a bad idea to junk your friendship over your crush and/or his sex fantasies if you don't have same-sex fantasies you're comfortable sharing with your girlfriend. You're walking a razor's edge.

Excellent answer WisperWill70