Am I Having an Affair With a Sex Worker?

I think I'm having an affair with my prostitute. For the past two years, I have been seeing a prostitute twice a month. I'm single and really don't date under normal circumstances. During the past month, we have been talking more and seeing each other outside of our business relationship. We are meeting up for coffee, going to dinner and having normal dates. She's really fun to be with; however, I know the realities of her profession. Our one-hour sessions are turning into three hours, and she refuses to accept additional pay. She's going out of her way to prepare a meal for me after our session, so I know she likes me personally.

Should I continue to enjoy her company beyond our usual business arrangement? She is always talking about how she would like to get out of the business, but the best job prospect for her is housekeeping or restaurant work. Despite her active work, I know she is lonely and has few friends. If she wasn't my prostitute, I would otherwise think she would make a fine girlfriend. But I'm not going to fall for her knowing what I know about her. Do I risk trouble if I am friends with her outside our business relationship? I should note that after I take her on a normal date, she gives me a freebie.

To get some perspective on this question, I talked to members of the Sex Workers Outreach Project, a national advocacy organization with a chapter in Chicago and the beginnings of one in Milwaukee. SWOP is run by current and former sex workers and/or people who work closely with them.

Two members of the Chicago chapter and one Milwaukee affiliate gave me feedback on your situation. All three of them emphasized the same key points. First, many sex workers will spend time with good clients outside of regular appointments to help cultivate the business relationship, so that alone does not mean that she necessarily has romantic feelings for you. Second, as with any relationship (business or otherwise), communication is important to make sure that everyone involved understands the terms of the relationship. In short, you won't know the answer to your question without bringing it up with this woman directly.

Serpent from Chicago says, "It seems that the woman you are seeing may like you 'as a friend' and just enjoys your company. There's no harm here, but I think the circumstances under which you met may be a little confusing for you, so I can understand your concern. Since you still have a business relationship going, there is always the possibility that she is treating you to the 'freebies' in hopes to keep you as a regular client. Just like any business owner would, special treatment for good customers is key to keeping them coming back. If you're questioning where the relationship is going, the best thing for you to do is talk to her about it."

Sinthia, also from Chicago, adds, "If this lady has confessed to having some feelings for you that fall outside the realm of a client relationship, then it would be best to have an honest conversation with her and make sure she understands that, while you enjoy your time with her, you are not interested in taking things to the next level. The possibility exists that she is hoping to leave the business and considers you a likely candidate for a more permanent relationship. Everyone has seen Pretty Woman.

"If you are just a good and fun client, her decision to spend time off the clock with you may be a purely selfish one,” Sinthia continues. “She may enjoy your companionship and has come to rely on your weekly donation. As such, by seeing you off the clock and giving you extra time, she is giving you extra attention so that you realize she values your business and she hopes you will want to continue seeing her. Many escorts see special clients off the clock for this reason. In any event, as with any relationship, communication is the key."

And finally, my contact in Milwaukee states, "I think about this from two ways. I've talked with many sex workers who enjoy spending time with clients outside of specific appointments; sometimes it's out of interest in that person, sometimes out of providing a good experience that keeps a client coming back, and sometimes from poor boundaries between work and life that can come from being lonely. It's unclear to me if, in fact, she's expressing real interest in a relationship that would mean consistently free sex.

"He asks if he risks trouble being friends with her outside the business relationship. I'd say at least one of the risks is that she may already or start to have feelings for him and believe his willingness to spend extra time with her is evidence of his interest in a nonbusiness relationship. So she could be very hurt when it becomes more obvious he's not willing because of what he 'know(s) about her.' Or maybe she'll laugh and wonder why he thought it would turn into anything entirely noncommercial. Sounds like time for a serious conversation."

So, there you have it. I'll add a final thought about why it is that you categorically dismiss having a relationship with your sex worker solely because of her line of work. If you think she would make a fine girlfriend otherwise, are you letting stereotypes and assumptions about sex workers get in the way of a mutual attraction? Many people view sex workers as "damaged goods" or unstable people who are not capable of sustaining strong romantic and family relationships, but this is not the case for the vast majority of people involved in the sex industrythey live and love like anyone else. There's a new book on this topic, Off the Set: Porn Stars and Their Partners, that will be released in early April.

Want Laura to answer your questions in SEXpress? Send them to laura@shepex.com. Not all questions received will be answered in the column, and Laura cannot provide personal answers to questions that do not appear here. Questions sent to this address may be reproduced in this column, both in print and online, and may be edited for clarity and content.

Laura Anne Stuart has a master’s degree in public health and has worked as a sexuality educator for more than a decade. She owns the Tool Shed, an erotic boutique on Milwaukee’s East Side.