I think there are plenty of opportunities for this - including most of the larger downtown hotel bars whenever a big conference is in town. There are a host of hotels around the the new DC Convention Center (Metro Center subway stop) that might provide this sort of opportunity. You might also find a few places near the Bay in the Annapolis area.

That said, I would consider going to one of the lifestyle clubs (like EN or Tabu) with the aim of talking to couples/wives to see where they go locally.....

I'm not sure if this is the right place to post this. I'm wondering if anyone has suggestions on bars (including hotel bars) or nightclubs in the DC area where one can find hotwives and cougars. I think it would be really hot to join my young stud and watch him pick up a hotwife or cougar and either watch or join them later. I'm pretty familiar with the DC scene, but not familiar enough to find these locales. Right now, I'm not looking for "lifestyle" clubs, but I might sometime down the road.