Three Is the Magic Number
You don't specifically say whether you're looking for a partner who will have a sexual encounter with both of you at the same time, aka a threesome, but for the sake of this column, I'll assume that's what you're interested in. There are two separate issues here: first, finding a woman who's interested in a threesome, and second, finding someone who's interested in anal sex.
Threesomes are a mythical beast, fantasized about by many. There are several ways to meet potential partners for a threesome: at social settings like bars, at formal sex-oriented events like swingers' parties, online, or even among your pool of friends. Before you start looking, though, it's important for you and your wife to talk through what it will mean to open up your sexual relationship. What are you each hoping to get out of this encounter? Is this a one-time fling or something you'd like to experience on a regular basis? How will you handle jealousy? What are your boundaries, and how will you negotiate them with a third person? It's important to make sure you're on the same page about all these issues before adding another woman to the mix.
Meeting someone in person (at a bar or other event where flirting is socially acceptable) is a good way to know immediately whether potential attraction to another woman exists for both you and your wife. The same is true for friends and acquaintances. You can discuss whether that hottie that you have your eye on also gets your wife excited before approaching her. Whether a friend or a stranger seems like a good prospect to you, it's usually best to let your wife make the first contact. You can get much more information in The Threesome Handbook: A Practical Guide to Sleeping With Three by Vicki Vantoch, but some short and sweet suggestions are: bring your best flirting game, take rejection in stride and don't be pushy or desperate. Be prepared to go home alone if the chemistry or the vibe isn't right, and watch out for signs of drama from people you're trying to pick up-better to be safe with no action than have someone stalking you later.
Meeting people at a sex-oriented event or online can be easier in some respects, because everyone's intentions are out in the open. The problem with sex-oriented events is finding out about them and getting invited, since they are usually private. The problem with online sites is the creep factor-you can never be sure that people are who they say they are, and everyone's heard about unfortunate Craigslist encounters. Some places to begin looking for sex-oriented events are Lifestyle Lounge (www.lifestylelounge.com) or Swing Clubs USA (www.swingclubs.us/). Besides the ubiquitous Craigslist, places to post personal ads include Nerve (www.nerve.com) and www.alt.com.
Looking for someone who's interested in anal play adds another layer of complexity. Again, sex-oriented events and Web sites allow you to be more upfront and specific about your desires right from the beginning. Tristan Taormino, anal sex guru, hosts her own personals at www.puckerup.com, so there may be a greater likelihood of finding fellow anal aficionados there. She also has a new DVD, Tristan Taormino's Expert Guide to Threesomes, that might give you some inspiration.
Finally, remember to keep yourself physically and emotionally safe. Be clear about what you do and don't want to do sexually, use latex barriers and lubricant, always meet people in public before you meet them in private, and be absolutely explicit about your intentions to avoid misunderstandings and hurt feelings.
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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.