Nope, but I've been to a family birthday party of a friend of mine's and he had a fleshlight, some condoms, and lube given to him by his older brother. Poor guy was embarrassed as hell (which was why his brother did it), so were his parents and grandparents though...
not in front of family but its ok with friends as long as they are laid back one time my friends and I did a x-rated Christmas gift exchange with a group of close friends. is was a fun time. for dinner we had penis mac and cheese. good times
Of course not! I would be terribly embarrassed if a "friend" did that to me, so I'd never do that to them, either.
Furthermore, they'd never expect to receive a sex toy from me to begin with. It'd be strange all around.
That would depend. Is it going to be funny for the family too? I would do that with some of my friends, because their parents would find it hysterical and so would the friends. But then there are others, who I would NEVER do that to because it would be hurtful and humiliating and not fun at all for them. Do something like this with discretion. If you know the family well enough to know that your friend won't be embarrassed and the family won't look down on them OR you, go for it. If you are even the tiniest bit unsure, DO NOT DO IT!