My partner is 31 years older than I am. I know the math: He’ll be 60 when I’m 29. But that isn’t the problem. The issue is he’s been a lifelong bachelor and never been monogamous. He’s fucked hundreds of women and is close friends with a lot of his former fuck buddies. Because of our four-year friendship before we hooked up, I know a lot about his sex life. The problem isn’t jealousy—and it isn’t knowing he’s fucked every woman he’s friends with or that he fucked someone else after declaring his love for me.
I’m an American woman living abroad and have started a relationship with a wonderful man from a Middle Eastern country. We are having a great time exploring what is a foreign country for both of us. The looming issue is sex, of course. He is a moderate Muslim, but he grew up in a strict conservative family and country. He’s 25 and has never even held hands with a woman. He is excited to change this now that he has broken away from his family. I have had many partners, both men and women, and am quite sexually experienced. I am curious about what to do when the time comes.
I consider myself a straight guy—but for the last four years, I’ve been having an affair with “Connie,” a trans girl I met online. It was just casual at first, but over time we developed a deeper personal relationship but kept it hidden. At some point, I figured out she was in love with me. I love her too, but I don’t think I am “in love” with her. Several weeks ago, I went on a couple of dates with a girl I met on Match.com.
I’m a straight male kinkster who used to do live performances as a rope bondage top, but I recently jumped out of the kink community. I just think I’ll have better luck finding a long-term relationship with a girl from the vanilla world. So long as she’s GGG, I can live with it. As much as I loved the sex/kink with people I met in “the scene,” I never found anything/anyone for the “long term.” My question: I’m unsure of how much I should share about my past. Should I tell vanilla girls that I performed at bondage shows?
I think my husband is addicted to porn. I find porn in his browser history almost every single day. He says I’m the only one he wants, but I find that hard to believe knowing he watches nonstop porn before fucking me. He also parties every time he goes on a business trip. Needless to say, I also suspect he cheats. He says he would never cheat on me because he “doesn’t need to.” But what does that mean? I think he is a liar. Every time I even try to bring anything up with him, it is flung back in my face because I cheated on him. He has the ultimate trump card.
I found this in an online sex ad: “Straight guy with an addiction to massive cocks in my ass.” This “straight guy” went on to mention his girlfriend. Can a person really identify as straight while wanting to be fucked by men? I understand that straight guys can like ass play too, but it’s not like he wants to be pegged by his girlfriend or use a dildo on himself. He’s straight-up (heh-heh) looking for hung dudes to fuck his ass.
I’m a straight guy in my 30s dating a woman in her mid-20s. We’ve been together for a year, and I’m crazy about her. In love, even. She’s gorgeous, sweet, kind, loving, and very sexual. She’s perfect. In her late teens and early 20s, she had a wild sex life. She attended sex parties, had loads of NSA hookups, sexted with random guys she met online, etc. She revealed this to me slowly and carefully out of fear that I’d look down on her, but what she didn’t know is that I have an intense cuckold interest.
When I was 15, I had a three-month-long sexual relationship with a 32-year-old woman. She was a friend of the family, and my parents were going through a divorce. I stayed with her for the summer, and she initiated a sexual relationship. Looking back, I can see that she had been grooming me. We used to have conversations online and via e-mail that were very inappropriate considering our age difference. The relationship ended when I went home, but she remained flirty. As a 15-year-old, I had a hard time sorting out my feelings for her, but we remained in contact.
While I typically encourage people to keep their questions brief, it is possible to be too brief, NH. But I’ve gotten so many questions from wannabe cuckolds with wife issues over the years that I’m going to hazard a series of guesses and take a shot at advising you…
I have been reading your column for years, Dan, and now I’m writing you for the first time to ask for a favor. I met this dude online in December and I felt like we had a good connection. He “dumped” me, though, because he was busy and was going through career shit and lived halfway across the country from me. I think a dude telling you he’s too busy for you is bullshit—because boobs—so I encouraged him to tell me the truth. He insisted he wasn’t shining me on: Busyness and career shit and distance were the truth, he said.
My father is 65 years old and has been a devoted husband to my mother who has been battling a medical condition for the past 30 years—a condition that prevents her from engaging in sexual activity of any kind. He has not had sex in all this time and is desperately frustrated. He’s not internet savvy—quite the opposite—and has taken to calling me across the continent from Michigan to ask for my help in getting him laid. At first, I just thought it was gross.
My 15-year-old son has been watching sadistic porn—and ONLY sadistic porn—for a couple of years. He also tells us (husband and me) that, though he’s not had sex (which he defines as penetration), he’s had oral sex, handjobs, etc., and that he didn’t “flash on” violent images at those times. But he says he thinks about this type of porn all the time—all day, every day—and fantasizes about doing sadistic things to the girls he dates. This all came out as we started having conversations about respect and dating!
My husband and I are a straight couple in our early 50s, and we’ve been married for more than 30 years. We were raised to wait for sex till we got married—this was back in the early ’80s—and we did. Our wedding night was pretty disappointing since neither of us knew what we were doing. He got off, but I didn’t. We both assumed that there was something wrong with me, because he didn’t have any problem coming, right?
I have a dildo that I loooooove, and I was wondering if it’s safe for me to use it in both my ass and my cunt. I would clean it in between uses/orifices, of course, and it has a flared base, so it’s safe for anal play. Can I do this or do I need to get separate toys for ass and cunt?
I’m a straight 18-year-old girl in my first sexual relationship. Things are a little awkward, and I could chalk it up to inexperience, but here’s what I feel conflicted about: I have a vore fetish. It was a fascination for me as a young child and became a sexual thing around the time I hit puberty. I’m wondering now whether this is something I need to get off. It works well when I’m on my own, but I always thought “regular stuff” would work too once I was actually getting some.
My fiancée is extremely bothered by me looking at porn. It revolves around insecurities that have gotten so bad that even other girls bother her. (We can hardly go to a beach anymore.) I don’t have any weird relationship with porn—no addiction, no violent stuff, and I look pretty infrequently. She acknowledges that it’s a normal thing but is unable to get past it. She has gone through two counselors on her own, and we have gone through two couples counselors.
What is your stance on maintenance sex? I’d never thought about the issue until reading Amy Poehler’s new memoir. I didn’t find anything she said controversial, and was surprised when this quote blew up in the feminist blogosphere: “You have to have sex with your husband occasionally, even though you’re exhausted. Sorry.” I’d never realized many people firmly believe one should have sex with their partner only when they are in the mood! Some articles even made it sound like maintenance sex is a form of nonconsensual sex.
I’m a short guy and I need advice. I don’t want a small paragraph’s worth of advice, like you gave “Below Their League” a few years ago. I need advice beyond “Women like men taller than them, get over it!” I get it. I’m short (five foot two), and most women are taller than me. And women like tall dudes just like I like slender women. Fat women may have it hard, but at least they have their fans and their own sex-object abbreviation: BBW. But where can a short guy go to feel appreciated?
We just did a live taping of the Savage Lovecast at Seattle’s Neptune Theatre. Audience members submitted more questions—anonymously, on index cards—than we could possibly answer during the Q&A segment of the show. So I’m answering some of the questions we didn’t get to in this week’s column. Here we go:
My partner wants me to pee on him. I’m not so into it. Now what? Should I do the “one and done” thing or put it on the big “no way” list?
I have been insecure about the way my vagina looks for as long as I can remember. When I was young, I would fantasize about the day I would grow pubic hair long enough to cover its unsightliness. That day never came, and I was left with an enormous insecurity about it. My labia minora is oversize quite a bit. I know that this is not uncommon, but its unattractiveness holds me back from receiving oral sex. I don’t even let my long-term boyfriend go down on me because I’m afraid he’ll think it’s gross and ugly.
I am a bi male in my early 20s who until recently was in the closet. I have been exploring my sexuality for the past year, and I didn’t want to label myself and open a Pandora’s box of oppression in the American South before I knew who I was for sure. I learned through my exploration that I have a few kinks and I have been acting on those kinks, seeing what I am and am not into. I may have been too trusting, because someone I interacted with decided that he was having none of me.
I am a 30-year-old trans guy, on T since college, happy and comfortable with my sexuality. However, I can’t find any helpful health info on a fetish I’ve developed: I insert needles directly into my clit, maybe an inch and a half in. I’m not talking through it, like a piercing, but into it, going in at the head and moving down into the shaft.
I’m a pretty quiet Midwestern woman currently wracked by a guilty Catholic conscience. My last boyfriend and I were in an open, long-distance relationship. We were together for a year and a half, and things were great fun. We considered each other our primary partners, but I met his other partners and felt fine about most of them, and I got to have some fun playtime back in my own city. Then I finished grad school and wanted to talk about moving to his city. He simply refused to have that conversation, and we broke up.