Q This woman has gone down on me (I'm a man) more than half a dozen times in the last three months. Each time seems to be better than the previous! She does not want reciprocation. She has also turned down all my offers for intercourse. As far as I know, she is heterosexual just like me. What's with that? I am getting a bit frustrated. Also, without going all the way, am I considered a friend with benefits? —Just Chilling
A You're benefiting here—think of all those blowjobs—and if she's a friend, you can certainly regard yourself as a friend with benefits. As for why she won't allow you to eat her pussy or put your dick in her pussy, JC, well, a few things spring to mind. She could be one of those women who love to give head and that's all she wants from a casual partner. Or she could have body-image issues. Or she could have a sexually transmitted infection, and she'd rather blow than disclose. Or she might be unwilling to risk pregnancy. Or she could be intersex or trans and not ready to open up. If you enjoy those blowjobs—if you're enjoying the benefits—focus on what you are getting instead of what you're not.
Q My husband and I occasionally go to swingers' clubs. I don't want to inadvertently fuck any Trump supporters, but I hate the idea of bringing up politics and killing everyone's collective boner. Any suggestions are appreciated! —Occasionally Swinging
A At the risk of killing your boner forever, OS, the organized swinging scene "leans right," as pollster Charlie Cook would put it if Charlie Cook polled swingers. Easily half of the couples I met at a big swingers convention I attended in Las Vegas told me they were Republicans. One man—a swinger from Texas—told me he was a "traditional values" type of guy and that's why he opposed same-sex marriage. Fun fact: His wife was off fucking someone else's husband while we were chitchatting in the hotel bar. Good times.
Q I'm a happily married 35-year-old mom. I have a loving and devoted husband. Recently, I started a job to get out of the house more and interact with more people. Well, it turns out my new boss is a real hottie. I have a crush on him and often find myself fantasizing about him. While I know these feelings can be normal, I tend to fixate/obsess. I'm basically looking for advice on how to move past this crush or maybe find a more productive outlet. —Newbie Fantasizing
A Here's a more productive outlet: Turn out the lights, climb on top of your husband, get him hard, then sink your pussy down on his cock and ride him while you fantasize about your boss. Bonus points if you and your husband are both secure enough in your marriage and cognizant enough of reality to regard crushes on others as normal and, so long as they remain crushes, not a threat to your marriage or commitment. Because then you can talk dirty with your husband about your boss—he can even pretend to be your boss—while you ride your husband's cock.
Q The other night while my wife and I were watching porn and masturbating together, I suggested we masturbate in front of DirtyRoulette. She asked me if that's what I do—if I get on DR when I masturbate. I replied yes, sometimes—and she was so taken aback, she ended our masturbation session to process it. We're fine now, but do you think this is "cheating"? —Dirty Rouletting
A I don't think it's cheating, DR, but you aren't married to me. If your wife regards you masturbating with strangers on the internet as cheating, then it's cheating. There are some people out there who regard too many things as cheating—fantasizing, looking at porn, even non-webcam or porn-enhanced masturbation. People who think this way usually regard cheating as unforgivable and their relationships are doomed to failure.
Q I'm deep in the grips of a run-of-the-mill midlife crisis. My marriage is in a slump, and I've been sexless longer than at any time since I was a teenager. My wife has granted me the DADT "hall pass," but I have no idea how to go about using it. My life is work, children, activities related to the children, and a few solo hobbies to keep myself fit and sane. I rarely meet new people, except at work, and I can't start a relationship with anyone there. In fact, my career means I am subject to a fair amount of social scrutiny and discretion is paramount. Any suggestions? —Hall Passing
A Remember Ashley Madison? The hookup site for married people looking for affair partners? The site that got hacked? A hack that outed millions of adulterers and ruined lives? According to The Outline, Ashley Madison is back, baby. "Once the dust had settled and other scandals entered the headlines, many people largely forgot about Ashley Madison," Stephanie Russell-Kraft reports. "This might explain why Ashley Madison's user numbers have shot up in recent years."
Q Any etiquette tips or best practices for introducing my husband to my boyfriend?
A Keep it casual and keep it brief, PP. A quick drink before you and your husband head to a sold-out show you have only two tickets for. If your husband has an unexpectedly emotional reaction to meeting your boyfriend—if it dredges up jealousy—you won't be putting him in a situation where he has to bottle that up for hours or a weekend.
QHey, Dan, you missed an opportunity in your response to Afraid To Bleed. She wrote that she bleeds whenever she has sex, and she was concerned about her partner's aversion to blood. But women should not bleed after vaginal intercourse. There are many reasons why they might. Please encourage ATB to visit a doctor. —Hall Passing
ABig oversight on my part, thank you for writing in!