"Savage Love"

I am a 23-year-old straight male. My ex-girlfriend and I started dating in high school, when we were both 17, and continued dating until I broke up with her the summer after our freshman year in college because things felt too serious. We continued to have sex, but I blocked out all my feelings for her, while she was open about still wanting to be with me. She started dating someone else sophomore year. I realized then that I still wanted to be with her, and I broke down emotionally and made both our lives difficult while she was dating this new guy.

I am uncircumcised, and the opening at the end of my foreskin is not large enough for the head of my penis to pass through. This means my foreskin doesn’t pull back when I get an erection. The internet says this is a condition called “phimosis,” and a lot of medical websites recommend circumcision. I’m not super-excited by that idea. I don’t have any pain or difficulty with sex or urination, and I’ve never had any health problems related to being uncircumcised. The foreskin isn’t stuck or fused to the glans — the hole is just small.

I am trying to understand some sexual fantasies I have. They involve having sex with a woman who has a penis. Sometimes I fantasize that my wife grew a penis. The fantasies started when we first tried pegging a few years ago. We recently had our first child and can no longer find the time for such kinky sex. These transsexual fantasies have caused a large strain in our relationship, and I don’t understand why I am having them or what I should do about them.

DEAR READERS: I’m off this week. To tide all of your hot and/or kinky and/or sore asses over, here’s a column I wrote 15 years ago. Some newer readers might’ve missed this column when it originally appeared — some of you who were still in grade school, diapers, or amniotic sacs back in 1998 — so I’m rerunning it now because I still get questions about “gerbiling” on a daily basis.  — Dan

My girlfriend and I read your column religiously, and I have you to thank for being comfortable enough with my kinks to tell her about my interest in BDSM. She is very GGG and has indulged all my kinky fantasies and discovered some of her own. Our latest adventure has her locking up my dick in a CB-6000 male chastity device. The play/sex has been super-fun so far, but we want to be aware of any health and safety concerns, specifically damage to my penis. We’ve had the device for almost a week, and I’ve been doing a ton of research.

A PROGRAMMING NOTE: I hosted a live taping of the Savage Lovecast in Seattle on Valentine’s Day, and it went great—thanks to all who came (especially to the five boys who left with butt plugs in their butts)—but I made the mistake of having a drink or five afterward, and I’m so fucking hungover right now that I shouldn’t be sitting upright, much less giving advice. But deadlines are deadlines. So here we go…

I’m a 27-year-old man in a two-year relationship with a 26-year-old woman. My last partner cheated and lied and did some unforgivable things. I wasn’t blameless — I stayed with her long after I realized it wasn’t working — but our relationship did unearth a kink. After I found out about her cheating, I got extremely turned on thinking about it. I never told her.

A friend of mine on the opposite coast is a crossdresser considering transitioning. He came out to a female friend he had known for a long time but hadn’t seen in a while, and she told her that she wanted her to come to her house fully dressed for some hot sex to “explore her bi-curiosity” or some shit. I told her to go for it, saying gender-transgression play is potentially hot. I neglected to mention that she should only go for it if she trusted this girl (hereafter known as “Evil Bitch”).

I’m a straight male, 21 years old. I love women, I’ve always loved women, I’ve always loved having sex with women. However, in the last year, here and there, I’ve jerked off to transsexual porn. One night, after drinking with a friend and smoking some hash, I arranged a date with a trans sex worker. She was totally womanly, nothing manly about her, except for, you know. She licked my butt, gave me head, and fingered me. I’ve been on the receiving end of anal play before from girls, so nothing new. But somewhere during this encounter, I became the receiving partner during anal sex.

I just started an intense relationship with a guy who has a boyfriend. This guy and I love each other. However, he is uncomfortable with me meeting his boyfriend. I’ve asked if it’s okay that we’re fucking, and he said they’re in an open relationship so it’s okay. I asked if it’s okay that we’re in love, and he said yes. So why the secrecy? My lover’s only explanation is that his boyfriend doesn’t want to know about the guys he fucks around with. The whole situation is starting to make me uneasy. I can’t figure out why I want to know more about his boyfriend.

At a dinner party, a straight man put a question to my boyfriend and me. He assumed that we, being gay men, would have an answer for him. We did not, Dan, and so we turn to you. What happens to one if one has to fart while one is wearing a butt plug?

Gays Are Simply Stumped, Yes And Sincerely So