Dear Ibby, My boyfriend and I are really into being watched. We've been talking about having someone watch us have sex, direct us on what they'd like us to do, and possibly participate if the energy is right. We zeroed in on one of our mutual friends who seems like he'd be pretty open to that kind of thing, but we're hesitant to ask him because we don't want to make things awkward if he says no (or afterwards if he says yes.) Even if he says no, we still want it to be someone we know and trust. Is there a right way to go about doing this?
My general method is just to bluntly ask and deal with the social awkwardness later, but if you're of the more refined and demure type, follow this 12-step program I developed six seconds ago.
1. Find out if he's even into that kind of thing.
Next time you see him, very casually slip threesomes, or the fantasy of watching people have sex, into the conversation. See how he reacts. Ask him if he's ever done that, and, if he hasn't, whether he'd be down (not with you, just in general).
If he acts repulsed, shy or seems uncomfortable, definitely fuck right off. He's a piece of vanilla on a stick and that's okay.
However, if he expresses interest, has past experience, or gives you the general sense he'd be receptive to some sort of kinky group-thing, well cha-ching. Proceed to step two.
2. Gauge your chemistry.
Alright, so now you know he's down for generalized freakdom. Great. Now you have to ascertain whether you've actually got chemistry, or if you're just feeling him because he shares your perversions.
Hang out with him, all three of you, and have a relaxed, fun night. See how your chemistry is. Do some mild flirting and try to notice if he's picking up what you're putting down. See if you can tell whether he's attracted to you (and/or your boyfriend). Usually, successful friend threesomes are borne out of some sort of mutual attraction between the couple and the other person, so if you're noticing some heat or tension between you when you present yourself more flirtatiously, then gosh darn it, Sally, bless your little achin' soul.
If not, fuck right off. He's not vanilla, but he's not right for you and that's just fine.
If the chemistry is there, proceed to step three.
3. Send him a text.
Okay. Now. after he leaves to go home, muster up some nerve and shoot him a text that says something like, "This sounds crazy, but Ricardo Diego Montoya Lopez Perez (or whatever the fuck your boyfriend's name is) and I were wondering if you'd be interested in watching us fuck … and maybe more. Totally no pressure! No is a perfectly acceptable answer. We won't take it personally, we promise." Don't you dare throw an eggplant emoji in there unless you're referring to the amazing ratatouille you had earlier — keep it classy; it'll make you seem like you thought this out.
Giving him the clear message that there is zero pressure, you won't take it personally and that it won't affect your friendship is the most important thing here. You want to present the question respectfully, casually and in a way that makes him feel totally comfortable saying no. It's also important that you address his needs in all this — while this is your fantasy, he's more than just a prop. You'll need to consider his comforts, boundaries and desires as well, so make a conversational place to do that.
Something like "We're totally open to discussing how this could work for you too" would work just dandily.
Now, the reason why I'd suggest texting as opposed in-person asking is that it gives the person a moment to collect their thoughts and think about it. Sometimes when people are affronted with a surprising question face-to-face, they give a canned answer, or they panic-respond with what they think the other person wants to hear. You don't want that.
You want him to be enthusiastic and intrigued, and texting gives him enough time and space to get to that place … or to craft a respectful rejection. It also creates some hot sexual tension. If he's down, you'll likely have a conversation about what that night (or 2:13 p.m. sex date) would look like, which can build up the anticipation in crazy ways.
Speaking of which, see step four.
4. Brace for rejection.
Say he says no. Obviously, you and your boyfriend went into it knowing that could happen, so come up with a plan of how you and he can communicate about and process this as a couple. It's normal to feel rejection, and it's normal to wonder if there's something "wrong" with either of you that would explain why your friend wouldn't want to watch you lackadaisically hump your boyfriend's face.
Of course, there is absolutely nothing wrong with you. In fact, there is something very right with you, which is that you're exploring your sexuality as a couple, and that you trust each other enough to be adventurous and honest with your desires. Rejection is every bit as big a part of the open-minded couple's life as it is a single person's, and no matter who you are and who you're dating/fucking, not everyone will be right for you. The important thing is that you shrug it off, keep trying and move on without taking it personally, because as I hope you've learned from reading my bullshit writing, taking it personally is a waste of your time that does nothing for you.
About your friend. Things may be awkward, or they may not be. Act normal, be friendly, and show him that your relationship is not contingent on whether or not he'd play Steven Spielberg to your Avatar, but on the fact that he's a good friend and that's that.
So, there. Try that method.
Another option here is to find someone you're not already friends with, and then become friends with them on the pretext that it's for some sort of future sex adventure-ing. I know you said you want it to be someone you know and trust, but that someone could easily be a cool stranger you find online whose trustworthiness as a human gets demonstrated across multiple non-sexual interactions. This could be a person you're very up-front about your intentions with, which are to get to know someone well enough to let them watch you have sex. That way, they know you'll be asking about it at some point; you just want to get to know them first.
Often, it's easier for us to express something like that to a stranger, because there's no fear of the relationship souring afterwards. We don't really give a shit what they think of us, so we feel comfortable saying things like, "My boyfriend and I are looking for someone to watch us fuck, do you want to hang out with us a few times and see where it goes?"
Online dating and fucking platforms exist so that you can lead with your desires as opposed to having to reveal them after you know the person, which really helps you tailor the right kind of relationship with the right kind of person right off the bat. Just something to consider.
Other than that, you could always put a large cardboard cutout of John Elway smiling in your room. Same thing, right?