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.
My brother is 22 years old and mentally ill with social anxiety on the scale of agoraphobia (officially diagnosed). He’s made significant progress in the past few years, but he’s stuck on the fact that he’s a virgin and is convinced that he’s not going to make any real social progress until that’s no longer a fact.
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
I’m an actor in New York City. A lot of people think actors are whores, but last week I almost became one. I responded to a casting call for a film project called Sniff. The ad — on Playbill’s website — called for two male actors to film a short scene. The pay was $100 for a day’s work. I was e-mailed the scene to study. It starts with two male roommates chatting on a couch. The bigger, more muscular roommate confronts the smaller, scrawnier roommate about his obsession with socks.
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.
I am writing about a friend. By all appearances, he is straight. However, on more than one occasion, he has gotten drunk and tried to hook up with a transvestite or a person who could have been one. In one instance, he went to a club and was approached by a really masculine-seeming girl who proceeded to give him head. My friend, in his drunken state, reached into her pants and felt for a pussy only after she started giving him head.
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 37-year-old single father with a 14-year-old son. I’ve raised him on my own basically since birth, with help from some good friends and nearby family. Overall he’s a good kid: gets decent grades, rarely gets in trouble. Our relationship isn’t perfect — I work a lot and he’s a teenager, but no major issues. Over the past year, however, I have become increasingly convinced that he is gay.
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.
I’ve been a fan of your Savage Lovecast for a long time, but I had to write after hearing Marty Klein’s awesome talk about the fallacy of “sex addiction.” I am 27, and for most of my adult life, I have suffered from complete sexual dysfunction with partners. I was ashamed and thought I was too sexually screwed up to be with a partner because I’m kinky.
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”).
My name is Nancy, and I'm 19. My boyfriend's name is Carl, we have been together for almost a year-our anniversary is actually February 14!-and we have great sex frequently! I want to do something sexy for us on our anniversary. I plan on being with Carl for years to come, and I don't want the sex to become monotonous. For a while, I've wanted to go to a sex store to purchase a few things to spice things up. I found a supportive, nonjudgmental friend who wants a few kinky things for her and her boyfriend.
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.
More than a thousand people showed up for a recent Savage Love Live event at the University of Wisconsin-Madison. It goes without saying that the students at UW submitted more questions than I could answer in 90 minutes. As promised, Madison, here are some bonus answers to questions that I didn’t get to during our time together ...
Can an open relationship work if it’s this type: dating two people, separately, both serious, neither relationship is the “primary” one?
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.
This is a touchy and gross subject. I am a 17-year-old girl growing up in an adoptive family in Australia. I was sexually abused by my birth family, and I think it really fucked up my sexuality. The only thing that gets me off is the idea of people absolutely destroying their lives for an orgasm. I started with mild S&M stories and then moved on to grosser stuff like murder (stories and online images), pedo (stories only), and lately I’ve been thinking about my (adoptive) parents. The thing is, it doesn’t have to be a particular category.
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?
Sometimes I kick the proverbial hornet’s nest intentionally — “bullshit in the Bible,” for instance — and sometimes I kick the hornet’s nest accidentally. I honestly didn’t expect the outraged response I got after I wrote that poly wasn’t a sexual identity in the “sexual orientation” sense of the term. Some people identify as poly, of course, just as some people identify as, say, dominant or submissive.
I’m a straight man at that age where the general public still considers me young. Although I’ve attended many weddings, I have no interest in marrying or even being in a relationship. I never have. I’m not asexual. I’ve had and enjoyed sex. I just don’t feel the need to be with anyone. As long as I’ve got music and friends, I’m satisfied. Unfortunately, I seem to be the only one. My parents want grandkids. My friends want to set me up. My television set only ever shows people in or pursuing relationships. My government wants me to father and raise future dead soldiers.
I am a 22-year-old straight female. I used to babysit for a wealthy family, but their children have outgrown babysitters. The dad of this family is very into martial arts/fighting and has invited me over several times for “self-defense training.” I have accepted his invitations a few times, and it has always started off as a normal workout in their home gym — treadmill, weights, swimming laps — but he is always pretty anxious to get to the self-defense part.
Reading you over the years has absolutely changed my mind on gay marriage. I wanted to let you know that. I also live in Maryland, and, as you know, we voted last week to allow same-sex couples to legally marry. I was excited that I got to vote for marriage equality in my home state, Dan — even I agree that it’s fucked up that people get to vote on the civil rights of LGBT people at all. Thanks for all your writing over the years — it’s really made a difference in my love and sex life.
DEAR READERS: I’m writing this week’s column in a drug-induced coma. Well, not quite a coma, but close. I was fighting a cold for two weeks, and the cold won: It morphed into an insanely painful sinus infection—you know it’s bad when your doctor urges you to err on the side of too much Vicodin, not too little. So a warning to everyone whose letter appears in this week’s column: My reliably sucky advice is probably going to be suckier than usual.
So I was innocently browsing the personal ads on Craigslist and saw one from a dude who was looking to try “saline balls” for the first time. Having no idea what this was, I googled it. Even worse, I google-imaged it. I pride myself on being unshockable, but I was completely and utterly mortified at what I saw. With that said, my copious internet searching failed to yield the answers to the basic/most important questions regarding saline balls: (1) What is the procedure/process for salining one’s balls? (2) What about it turns on the saliner/salinee?
What the hell do I say to my straight 14-year-old son about porn? Should I say anything? My sister tells me that all the research shows my son has been looking at porn for three years already. Am I too late?
I’m pro-choice. The anti-choice position — particularly the dumb contention that “personhood” begins when sperm hits egg — is illogical and unappealing. It’s not the most unappealing quality I can think of in a partner, though — that would probably be dishonesty. Your advice last week to the young woman who discovered that her boyfriend is anti-choice was terrible. You advised LIFE to tell her boyfriend that she’s pregnant in order to see if that changes his position.