I am on vacation for all of July. But I've invited Mistress Matisse to handle the Savage Love letters of the day. Mistress Matisse is a writer, a dominatrix and a sex worker’s rights activist. She has a blog here and twitter here. The archive of her Stranger column, Control Tower, is here. Mistress Matisse will be answering your questions all week.

I'm a 27-year-old gay guy living in a medium-sized city, happily single. Over the last few years, I've had this recurring fantasy more and more: to watch a straight couple having sex. I started watching straight porn, and then I've ended up going to a few swingers clubs, where sometimes I end up being able to watch something hot and sometimes I don't, but I can never be really close up for reasons of etiquette. I've posted a couple of ads on CL, but those have never panned out to anything real, mostly because I'm not looking for a relationship, or to have sex with the woman... and also, perhaps, because there are lots of CL flakes.
I'm going on a business trip to a larger city next month, and it occurs to me that I could fulfill my fantasy in an ethical way by hiring sex workers. I've never paid for any sexual services before, but I have no moral qualm with it. However, no matter how much I Google, I can't figure out how I would find two escorts that would be willing to come together (pun intended). I can't find an individual escort who discusses the issue on his/her site and I can't find a discussion board or forum that mentions it.  What should I do?

Wanna Watch Straight Sex

Mistress Matisse's response after the jump...

You sound like someone I would have enjoyed having as a client when I did straight sex work, and I know lots of female sex workers who would find your request enjoyable to fulfill. “Someone wants to pay me to have sex with a man of my choice? Swee-et!” If you can find the right pair of people, this could be a good experience for everyone involved.
So I applaud your instincts about how to get your fantasy satisfied, and I have suggestions for how to proceed, but I also have a word of caution. Part of our country’s current ridiculous and harmful attitude towards sex is that you can legally buy porn, and you can pay to enter a swing club to observe other patrons getting busy, but - if you offer money directly to people to watch them have sex, you could end up being arrested. The US is in the midst of an intense moral panic and a concurrent legal crackdown on people exchanging sex for money, even if it’s done in private by consenting adults. Mainly it is sex workers themselves who are arrested, but there’s been a sharp increase in stings of would-be clients as well. You need to be careful here.
(It is true that if you were arrested, and you took the case to court and fought it, you might be found Not Guilty on the basis that you did not ask these people to have sex with YOU. But this would be after the press had published your name and your picture as part of their client-shaming “End Demand” campaign. At that point, whether you were ever actually convicted of a crime becomes fairly trivial.)
Generally, I advise people seeking a sex work services provider for the first time to choose an independent sex worker, who has a solid web presence and a good professional reputation that goes back at least a year or two. Such a person is more likely to correctly intuit your wishes and be invested in creating a good outcome. In your case, I’d also suggest someone who has done porn or cam shows in addition to escorting.
Anywhere sex work is criminalized, there are two rules of initial contact with sex workers: you do not talk about sex, and you do not talk about money. This naturally makes it difficult for people who are doing sex work to safely establish their boundaries, or for those hiring sex workers to ask for what they actually want. But that’s how it works – both sides must rely on euphemisms. So when you contact an escort by phone or email, definitely don’t say “I don’t want to have sex with you, I just want to watch you two have sex.” Say something like, “I was looking for a lady who has a boyfriend or husband that she could bring with her, because I’d like to spend time with a couple.” The phrases to employ are “spend time” or “enjoy the company of”. Believe me, an escort knows what this means. By saying “a couple,” you’re indicating that you want them to interact with each other. I can’t think of a good coded way to say, “But I just want to watch”, and I’m not sure it’s crucial to communicate that part before you meet anyway. If you feel really secure in the sex work service provider you’re dealing with, you might say something like, “I’d enjoy watching you give each other sensual massages” or “I’d enjoy watching an erotic performance.” I would not get any more specific than that.
You could also approach a male sex worker - which might lower your odds of getting busted, since adult male sex workers are largely ignored by anti-sex work crusaders, unless they are on the street. But outside of major cities, there are fewer of them. Use the same language, however.
If she/he mentions the per-hour fee, just say something like, “Yes, I understand.” If it’s not mentioned, assume it is double whatever the individual sex worker’s rate is. When they arrive, either give the money to them without comment or just put it down where they can see it, whichever seems indicated. After this point, there will be a little so-let’s-get-acquainted chitchat, and it’s probably okay to say something like “I’d like to just watch you two.”
I hope you get the experience you want, and I also hope that as you go through life, you remain aware of your status as “someone who has hired a sex worker”. Please view anti-sex work news stories with a sharply critical eye, don’t make dead-hooker jokes, and whenever possible, vote for politicians and policies that don’t stigmatize sex workers.