I usually give a sexy gift (lingerie or toy) for Valentine's Day, Birthday, and Christmas...and occasionally Halloween too. I've lost count of all of the ones I've given, but it's probably around two dozen - 50% toys and 50% lingerie (or cosplay). I can't imagine when I'd stop giving naughty gifts...but I'm sure it'd be a sad holiday
My Man and I give each other sex toys as gifts frequently. But, aside from maybe some JimmyJane candles, I can't see too many people I know being cool with sex toys as gifts. I also don't know what people may have, so the few people I know who would be cool with it, it's just hard to know what people like. Or what they already have.
I gave a couple of toys to a friend last year for Christmas. It was hard to pick things out without asking her about it before hand. I only asked what colors she *didn't* like and I went from there. When we were exchanging gifts, we were in a restaurant so I just told her to open the last box at home. She sent me a very pleased message later that evening ^_^