I am a 23-year-old bi girl in the Midwest. I was talking with a friend from LA the other day—a sexy lady friend, ten years older than me, and did I mention she's sexy?—and her boyfriend wants to have a threesome and she wants me to be their third. She offered to fly me out, put me up, and show me a good time in exchange for hopping into bed. Great. Super hot. That said, I'm nervous about letting them spend money on me because... what if I don't want to fuck around with them once I'm there? I would feel an obligation to get it on. Is this is prostitution? This is new territory for me. Got any ideas for how to help things go smoothly for a horny girl who wants a free vacation and to get laid?

Wanting Happy Orgasms, Realistic Exchange

My response after the jump...


Have you met or talked with the BF? Are you into him too?—Dan

I met him once in passing last summer. We exchanged a few words of small talk. Everything about him seems okay. Okay looks, okay personality... but underwhelming. I can see myself in a no-penetration threesome with this dude because I'm really into his girlfriend and he seems perfectly tolerable. My lady friend and I are both subs and she says he's a great Dom. So that's enticing, honestly. But I don't know.—WHORE

Unicorns—single, available, and willing bisexual women—are so hard to come by/in/on that I feel almost bad about queering the deal. But I wouldn't get on that plane, WHORE.

I don't think you'll be making a huge mistake if you do decide to get on that plane—and getting on that plane doesn't make you a whore. Assuming your friends are offering to put you up at their place and not get you a hotel room, WHORE, they're only gonna be out the cost of a round-trip airline ticket. In restaurants all over North America on any given Saturday night people are treated to meals that cost as much or more than a coach ticket by folks who wanna fuck 'em. (Yes, yes: young people and their hookup culture and their "sups" and like that. But trust me, kids, lots of people still go out on dates. Sometimes even people in their twenties.) It's perfectly acceptable to let someone who who wants to fuck you spend a little money on you—provided, of course, that someone has a reasonable chance of getting in your pants.

We know your friend stands a chance. And it does seem like your friend's BF stands a reasonable chance. He's okay in the looks and personal departments. But he's also a skilled Dom, at least according to your friend, which means he possesses a skill set that might compensate for whatever he lacks in the looks and personality departments. (And who knows? His looks and personality might grow on you if you spend some more time together.) But it's a lot easier to say "no thanks" and "goodbye" after someone takes you out to dinner—it's easier to extricate yourself—than it will be to say "no thanks" when you're staying with your friend and her BF.
And if you fly out, and he gives you a bad vibe, and he doesn't get your sub senses tingling, and you don't want to go through with it... you might wind up going through with it anyway. Even that won't make you a whore, WHORE, but it will definitely leave you feeling crummy after it's over.

Before you make up your mind, WHORE, have a couple of long Skype chats before a plane ticket is purchased and be absolutely explicit about what you're comfortable agreeing to in advance, i.e. a non-penetration threesome (or a threesome in which you're not the one being penetrated), and emphasize to your friend and her BF that you have a right to back out if you're not feeling it and that they have to cheerfully respect your right to back out.

If they're down with all of that, and if you're all able to regard that plane ticket as an expensive dinner date that may or may not lead to something more, then maybe you should go.—Dan