My answer – No I would not go. Personally I see about a million red flags for a first date being a swingers event. Might want to know someone well before you venture into something like that. Unless you are already a seasoned swinger, then by all means, I guess.
Personally I have no desire to ever go to a swingers event, and slapping a mask on, adding some communication rules, and calling it a masquerade doesn’t really change the fact that your date will be balls deep in another girl while you are getting drilled by a more-than-likely hideous creature.
But, like I said, if you have done this before and you like it, and he has too, then I guess there is no harm in it. Just make sure it’s legit first.
Usually something like this comes when two people have gotten to know each other well – hence my reluctance. If you just want to fuck strangers, then carry on, but if you want to have a future together, I suspect you may be starting off on the wrong foot.
Now if it is one of those non-swinger masquerade parties, where a bunch of morons wear masks and pretend they are sexually enlightened or something…I think I would rather watch paint dry.
A first date should be a guy opening your car door, telling you that you are beautiful, picking up the check at a nice steakhouse, kissing you at your doorstep, you asking him up for coffee, and him yanking your hair as he bends you over after eating your pussy like a champ. The 5th date? Go ahead and fuck the Phantom of the Opera.