Three's Company

Normally I would try to incorporate this into a story, but a funny thing happened last night...

I went out to the bar with some friends, in usual form. But this night was different, because instead of getting belligerently drunk and going home with a stranger, I was approached late in the evening by an old friend from high school.

I'm not in touch with too many people from high school--I moved away for college and have never really gone back. James is not an exception--before this night I don't think we've seen each other since maybe 2001. James is now living in the same city as me working for some investment firm. He's been dating the same girl for a few years and they live together. She seems nice enough.

In the heat of catching up, my friends left the bar without me and I was alone with James and his girlfriend.

And pretty much out of the blue, they asked me to do a 3-way.

Now, as interested as I am in this particular activity, I'm pretty sure that the only way to go about this type of thing is with someone who you've already slept with at least once (familiarity makes everything a bit more... fluid), and to be the guest star.

Thoughts or feelings?