I was involved with a straight man who enjoys cross-dressing and taking explicit photos. The problem is that the props he uses belong to his three children, all under age 12. For example, he dressed up as a slutty schoolgirl and wore his daughter’s backpack. He dressed up as a slutty cowgirl and posed with his son’s…
Is it even possible for a couple that stopped having sex to start back up again? My girlfriend and I (we’re both women) have been together for four years, and we haven’t had sex for two. I thought the sex was good before it stopped, but apparently she was going through the motions. She’s a sex worker, and it took her…
I’m a 62-year-old woman. I was married for 33 years and left five years ago. We hadn’t gotten along for years, but he never stopped wanting or valuing me for sex—in spite of treating me like a household appliance and cheating on me regularly. Not long after the marriage ended, I met a guy online (my same age) who…
I am newly divorced and have started a relationship with a man I’ve known and deeply cared about for decades. The sex is amazing—from start to finish, I feel better than I ever did even in the best moments with my ex. And in the most intense moments? He makes me see stars. He is a very generous lover—he turns me on…
I am a gay man in my late 50s and have never been in a relationship. I am so lonely, and the painful emptiness I feel is becoming absolutely unbearable. In my early 20s, I hooked up off and on, but it never developed into anything. I have always told myself that’s okay; I’m not a people person or a relationship kind…
I’m a cis woman in my mid-40s, and my significant other has a cuckolding fetish. My first response was “Oh, hell no!” But if I’m willing to have a threesome, how much further of a stretch is it, really? He does have some experience with this varsity-level kink, so he knows what to expect. I’ve asked him some…
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…
I’m in a pickle. All I want is to experience touch, intimacy, and sexual pleasure—but without freaking out. I grew up with a lot of negative messages from men due to developing early, as well as having some other physical/sexual trauma (no rape or abuse), but the combination has me seriously fucked up. Whenever I get…
I’ve been enjoying consensual nonmonogamy for the past two years, in part thanks to your column and podcast. I have a delightful young lover, and our connection has evolved into a kind of Master/slave relationship. I “allow” her to fuck other men and women, and she delights in asking my permission and recounting the…
I’m a 27-year-old woman living on the East Coast. I’ve been sexually active and on birth control since I was 16—almost always on the pill. I recently switched to the NuvaRing, which I had a bad reaction to: I had no libido at all and extreme mood swings/bouts of depression I could not live with. My boyfriend and I…
I’m gay and have been dating a guy for 10 months. He’s great overall, and I would say for the most part we both want it to work out. But I am having a problem with his friends and other lifestyle choices. All of his friends are straight, and almost all of them are women. All of my friends have always been gay men,…
I’ve been faithfully reading your column in the Chicago Reader for years, and now I’m reaching out to you about my own problem. I’ve been dating this guy for almost a year. Everything is great, except one thing: He wants me to kick him in the nuts. It really bothers me, and I’m not sure what to do. He’s very serious…
I’m a 20-year-old submissive woman. I’m currently in a confusing affair with a 50-year-old dominant married man. He lives in Europe and has two kids close to my age. We met online when I was 17 and starting to explore my BDSM desires—out of the reach of my overbearing, sex-shaming, disastrously religious parents—and…
Longtime Savage Love fanboy with a bit of a conundrum—and it’s your fault! I’m a bi man in my 30s. To use Charles M. Blow’s word, my bisexuality is “lopsided.” This means that I fall in love with women exclusively, but I love to have sex with men occasionally. My current girlfriend not only approves, she likes to join…
In a recent column, you said you never hear from married couples whose sex life got better and more frequent over the years. Well, now you have. My wife and I were married 24 years ago, and we are currently having more sex and better sex than we did in the first years of our marriage. There are many reasons why,…
When I started dating my husband, he told me he had a low libido. I said I could deal with that. We waited several months before having sex, and then after we started, it was infrequent and impersonal. There was some slow improvement over the three years we dated. Then we got married, and suddenly he had no libido at…
I am a 24-year-old straight guy who recently broke up with my girlfriend of more than four years. One of the reasons we broke up was a general lack of sexually compatibility. She had a particular aversion to oral sex—both giving and receiving. I didn’t get a blowjob the whole time we were together. Which brings me to…
Without snooping, I came across texts between my wife, “Mary,” and a guy “Jeremy” of a very sexual nature. While I would be okay if she were doing this and I knew about it, this has been going on since before we met. (We’ve been together 10 years.) She says she has never met him in person (despite communicating with…
I’ve been married to my husband for two years. Five months into our relationship (before we got married), he confessed that he was an adult baby. I was so grossed out, I was literally ill. (Why would this great guy want to be like this?) I told him he would have to choose: diapers or me. He chose me. I believed him…
I am a 38-year-old gay man with a serious problem. My boyfriend of five years has developed a strange fascination. We’ve always watched porn together, but now he has been looking at straight porn and even lesbian porn (!!!) more and more often. More than once he has expressed an interest in having a MMF threesome—and…
