I only ever came close to this once. Back from 2005-2007 when I was in college, I was perusing the swinger's personals for my area. I happened to find an account from a couple advertising what they were looking for. They didn't want an ugly 30yo guy w/ a b!tch for a gf (that soon turned into a b!tch of an ex-wife years later), so I didn't bother responding.
But they included a couple pics, and the first was a shot of the two of them sitting next to each other on a bed cuddling for the camera, showing their faces w/ no obstructions.
The girl was in one of my drama classes. Cute Asian girl.
Again, I never responded to the ad so nothing ever came of it. And since I wasn't particularly friendly w/ her in class (she pretty much kept to a small group of friends & I'm just an antisocial fuck to start with), I didn't bother approaching her in class either.
Still, I read all the time about drama classes in college where the instructor pretty much makes nudity part of the assignment, and I was a little jealous because none of my classes were like that. But I still got to see one of my classmates in the buff thanks to my "extracurricular" interests.