Dear Dan: 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
Dear JC: 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.
Dear Dan: 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 would be appreciated!
—Occasionally Swinging
Dear OS: 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.
Dear Dan: 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
Dear NF: 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. (Perhaps this is better described as a more productive inlet?) 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.
Dear Dan: The other night while my wife and I were watching porn and masturbating together, I suggested we masturbate in front of DirtyRoulette. I briefly explained what the site is about. 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
Dear DR: I don’t think it’s cheating, DR, but you aren’t married to me. In other words, if your wife regards you masturbating with strangers on the internet as cheating, then it’s cheating. There are, of course, some people out there who regard too many things as cheating — fantasizing about others, looking at porn, even non-webcam-or-porn-enhanced masturbation. People who think this way usually regard cheating as unforgivable and, consequently, their relationships are doomed to failure.
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