I am a trans man and I have no love life. But I did just hook up with a friend two nights ago. It was the first time I’ve had sex in more than a year. My problem is that it was a “one-time thing.” I was hoping to be FWB at least. I’m furious with myself for giving that away for what amounted to a hookup, and thoroughly sorry for myself for it being a “one-time thing,” because it nearly always is. I feel thoroughly unlovable and dejected right now. I was raised a Boston Irish Catholic, and I have PTSD from my parents being difficult.
I’m a 49-year-old gay man. I’ve become friends with a 21-year-old straight guy. He’s really hot. He’s had to drop out of college and return home. I know he needs money, as he hasn’t found a job yet and has resorted to selling off old music equipment. I would love to have some sweaty clothes of his, namely his underwear, but I’d settle for a sweaty tank top. Is it legal to buy someone’s underwear? He’s a sweet guy, and I don’t want to freak him out by asking something so personal. How do I broach the subject?
I am a twentysomething, straight, cis-female expat. How long do I have to wait to ask my German lover, who is übersensitive about the Holocaust, to indulge me in my greatest—and, until now, unrealized—fantasy: Nazi role-play? He is very delicate around me because I am a secular Jew and the descendant of Holocaust survivors. (Even though I’ve instructed him to watch The Believer, starring Ryan Gosling as a Jewish neo-Nazi, to get a better grasp on my relationship with Judaism.
I was honored to speak at JCCSF—Jewish Community Center of San Francisco—last week as a part of their “Uninhibited: About Sex” lecture series. The audience submitted questions on cards, which were ably put to me by Jourdan Abel, who was wearing a wonderful uterus-themed sweater. (Check out my Instagram account—@dansavage—to see Abel’s sweater!) Here are some of the questions submitted by the uninhibited JCCSF audience that Abel and I didn’t manage to get to during our conversation.
I’m a 24-year-old male, married three years, monogamous. My wife and I are religious and were both virgins when we got married. I’m sexually frustrated with two things. (1) How can I get her to give me oral sex? (She has never given and I have never received oral sex. I regularly give her oral sex.) She is afraid to try it, saying she’s not ready yet. About every six months, I bring it up and it leads to a fight. She is a germophobe, but I think she believes fellatio is done only in porn.
I’m a 27-year-old, feminist, conventionally attractive, straightish, GGG woman. Over time, my tastes have changed, and now I find myself more of a kinkster. A few years ago, my desire for kinkier sex and my willingness to take a chance came together in a mutually beneficial, exciting D/s relationship. I’ll be honest: I wasn’t as smart as I could have been. I met this guy on Tinder, and after verifying his identity, I told some friends where I’d be and I met up with him.
I’m your average straight 42-year-old white guy. Married for a little less than a year (second marriage for both). We have an active sex life and are both GGG. My wife wants to be forcibly fucked — held down and raped. Normally I’d be all over this because I do love me some rough sex. My issue: She told me she was traumatically raped by a man she was dating prior to me. All I know is that it involved a hotel room and him not stopping when she said “no.” So for now, I play along, but I know I’m not taking things as far as she’d like.
Are you incapable of concision? Your answers are too long! You blather on, often rehashing the problem (unnecessary!) before giving four words (at most!) of (rarely!) useful advice. I’ve heard you say you have to edit letters down for space. Try this instead: Edit yourself! I want more of the letters—more from the people asking questions—and less of YOU.
Gay, thirtysomething male in DC. My boyfriend of three years has been acting strange—not taking his antidepression meds, says he’s feeling weird. He has withdrawn from me, sleeps 15 hours a day, and has been canceling on commitments to socialize with friends. That I am fine with—he’s blue and I get it. Here’s why I’m writing: He was doing an online crossword, and when he got up, I was going to write a message in it—to be funny and sweet. What I saw messed me up. There was a browser window open about meth and depression.
My new girlfriend blurted out that she had a cuckolding past with her ex-husband. She says her ex badgered her into arranging “dates” with strangers and that he picked the guys. Her ex would then watch her having sex with a guy in a hotel room. The ex only watched and didn’t take part. I am really bothered by her past. She says she did it only because her ex pressured her into it and she wanted to save her marriage, so she agreed. But I suspect she may have enjoyed it and may have been testing me to see if I wanted to be a cuck. What should I do?
Gay male in my late 20s. I recently ended things with a guy. Our relationship started as a strictly sexual one. We’re both involved in the kink scene in our city and have interests that align in a particularly great way. Quickly it became clear there was a real connection. The next two months were great! I had a toothbrush at his place within three weeks. But early on, I noticed that he was a much more extroverted person than I was. He would laugh loudly at movies, work the room at parties, say things about kink in the middle of crowded restaurants. I prefer to blend in.
A large crowd braved a snowstorm to come out to Savage Love Live at Boston’s Wilbur Theatre last week. Questions were submitted on index cards, which allowed questioners to remain anonymous and forced them to be succinct. I got to as many of them as I could over two long, raucous, boozy hours. Here are some of the questions I didn’t have time for in Boston…
What do you think of poop play?
I think of it rarely.
How long should I keep my partner locked in male chastity?
Down to business: Christmas came and went, and every present I bought for my extraordinary husband could be opened in front of our children. He deserves better, and I have a particular gift in mind for Valentine’s Day. My husband has expressed an interest in sounding, something we’ve attempted only with my little finger. He seemed to enjoy it! But the last thing I want to do is damage his big beautiful dick. So is sounding a fun thing? Is sounding a safe thing? Recommendations for a beginner’s sounding kit?
I am no longer sexually active, but I have a significant collection of sex toys from earlier years. I’m thinking of getting rid of most of them, and it seems such a waste for them to end up in the landfill. What’s an environmentally responsible way to dispose of dildos? I wish there was a place I could donate the dildos where they could be used again. Many of them are quality silicone types, they’ve never been used on a person without a condom, and they’ve been thoroughly cleaned.
As a queer man of color—I’m Asian—I feel wounded whenever I am exposed to gay men in New York City, Toronto, or any city where white gay men dominate. Gay men, mostly whites and Asians, reject me because of my race and no one admits to their sexual racism. I understand that sexual attraction is subconscious for many people. But it is unfair for a gay Asian like myself to be constantly marginalized and rejected. I fight for gay rights, too. I believe in equality, too. I had the same pain of being gay in high school and the same fears when coming out.
I’m a 45-year-old straight male. Politically and socially, I consider myself an ardent feminist. There is nothing I enjoy more than giving a woman an orgasm or two. I’m very GGG and will cheerfully do whatever it takes. Fingers, tongue, cock, vibrator—I’m in. If it takes a long time, so much the better. I’m okay with all of that. Now and again, though, I really like a quickie, a good old-fashioned “Wham, bam, thank you, ma’am!” The only ladies I’ve found willing to engage in those cock-centric acts are sex workers.
I am a 30-year-old straight man and I’ve been with a 28-year-old bisexual woman for a year. Early in our relationship, after much discussion, we established that it would be open. I would have the liberty to see other women and so would she. We just had to be safe and always keep each other informed. The key was that she agreed to see only other women. I was uncomfortable with the idea of her being with another man, and she went along with it. Fast-forward a few months, and she told me that she had drunkenly kissed a male coworker. Hearing her say that hurt me.
After spending some years in the doldrums after having kids, my husband and I are now enjoying hot kinky sex and the occasional free pass to fuck other people. We couldn’t be happier. I have a friend who was extremely keen for me to cage his cock with the same kind of locking male chastity device I got for my husband—a fixed-ring stainless-steel type. I have two questions: (1) It took some maneuvering to get my husband’s balls through one by one, followed by his cock, but he managed.
I’m a straight 26-year-old man who wants advice on helping my fiancée realize a particular fantasy. We have been dating for three years and are in a happy monogamous relationship. I was always vanilla, but she enjoys rougher sex and light bondage. We’ve incorporated some of this into our sex lives, and we are both happy with how fun it is. She has expressed interest in a rape fantasy. Both of us want to be safe when we do this, and we trust each other completely.
I’m a 24-year-old gay male with few resources and no “marketable” skills. I have made a lot of bad choices and now I struggle to make ends meet in a crappy dead-end job, living paycheck to paycheck in an expensive East Coast city. Recently, someone on Grindr offered me $3,000 to have sex with him. He is homely and nearly three times my age, but he seems kind and respectful. I could really use that money. I have no moral opposition to prostitution, but the few friends I’ve spoken to were horrified.
I’m a straight female in my mid 20s. I’ve been dating a wonderful guy for two years—but I recently found something that has put me on edge. Before we met, he was in a relationship with a terrible, alcoholic, and mentally unstable woman. They got pregnant early in the relationship and stayed together for about five years. We met a year after they broke up. I felt like I’d come to terms with the ugliness of his past, with his trying to stay in a bad relationship for the sake of his child and the rest of it.
A couple of months ago, I got candida (a fungal infection) under my foreskin. I went to the doctor, picked up some cream, and used the cream as directed. The infection went away for about a week and then returned. I got this idea that maybe the cream didn’t work the first time because it’s so naturally moist under the foreskin. So I used the cream a second time—but this time, after each application I would “air out” my penis, i.e., pull back the foreskin and leave the head exposed to the open air for a little while.
I’ve always been a big believer in the common-sense obviousness that monogamy is hard. Additionally, I like the idea of my wife getting fucked. I don’t have any desire to be denigrated or emasculated; I just get off on the idea of her being satisfied and a little transgressive. Early in our relationship, we talked about monogomish guidelines: I’d like to be informed and consulted, and she would rather I kept mine to myself. Last weekend we were having sex, and she asked me if I “wanted to hear a story,” code for treating me to a tale of a sexual contact.
I’m a hetero guy in need of advice. Back in college, I met this girl. Suffice it to say she was into me but I had some shit to work through. So we ended up being a missed connection, romantically. Despite that, we still became fast friends. I’m less awkward now, in large part because our friendship changed my life. We each married other people, and everything worked out great. Except I still love her. I think about her often, want to share things about my life with her, find myself wanting to rely on her when things are tough. I don’t know what to do with it.
DEAR READERS: Two weeks ago, I announced I would be taking a nice long break from questions about miserable sexless marriages. (I don’t get questions about happily sexless marriages.) I tossed out my standard line of advice to those who’ve exhausted medical, psychological, and situational fixes (“Do what you need to do to stay married and stay sane”), and I moved on to other relationship problems. Readers impacted by sexless marriages—men and women on “both sides of the bed”—wrote in to share their experiences and insights.