Savage Love

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September 1, 2010

Here’s my problem: I love women. I love the way they look, I love the way they move, I love the way they sound. I like to see them naked. But the idea of actually interacting with women—trying to engage them in intelligent conversation without coming off as absolutely leotarded—absolutely fucking terrifies me. I’m a virgin at 30. I’ve never had a girlfriend. I’ve never been on a date. I’ve never even had a conversation with a woman that lasted longer than a couple of minutes and wasn’t completely superficial and forced.

I cannot even imagine myself doing something assertive like approaching a woman and asking her out on a date. And no woman has ever approached me or even shown interest, from what I could tell. Sex workers are out of the question because I don’t want to risk some asshole cop busting me. Webcam sites are pretty much the only way I interact with women. Sad, no? I’m not at all afraid of vaginas—I’m afraid of women who have clothes on.

Got a piece of advice for me?
Awkward And Alone

I’ve actually got two ...

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August 25, 2010

I lost my virginity last night.

I’m a straight male in my early 30s, so it was about time. It wasn’t awkward, and we had a good time. However, I didn’t climax during sex, which is a result of years of death-grip masturbation. (Thanks for the warning, Dan, I’m sorry I didn’t heed it.) She took it personally, but seemed satisfied when I said it was only nerves.

I am left this morning with more confusion and trepidation about my relationship with my new girlfriend than I had going in. I suppose this is normal, but I don’t see last night as some victory or a “bonding moment,” and I am afraid that is a bad sign. I also find myself being extra-critical of my partner’s performance, which, as a virgin, I am not in a good position to judge. She has never been a particularly good kisser, and her blowjob technique was less than spectacular. Although it was a pleasant experience, I feel like it lacked passion or a spark, which is probably just normal for a first time, but I am concerned.

I feel like an asshole for even having these ...

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August 18, 2010

My boyfriend and I are straight college students, and he’s always wanting to try new things. Recently, he asked to put a finger in my ass while we were having sex. Someone did that to me before, but it felt uncomfortable and it kinda hurt. I told my boyfriend that he could do it once, and then I would decide whether to let it continue. So we tried it. It still felt uncomfortable and still kinda hurt. But I never came so hard in my life!

Now the question: If it’s uncomfortable, but it made me feel amazing and come really hard, what should I do? Continue with it? Or tell him to find some other way of getting me to that point again?
Presently Obsessing Over Totally Extreme Reaction

You could ask the boyfriend to stick a finger in one of your armpits—or in an eye, a nostril, your toaster—but unless your pit/eye/nostril/toaster is wired the way your butt appears to be, POOTER, no amount of pit/eye/nostril/toaster fingering is gonna jack up your orgasms quite the way that finger in your butt did.

So here’s what you’re ...

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August 11, 2010

Longtime reader, first-time mailer.

A long while ago, you wrote an incredible piece of general advice for teenage boys. The advice was so excellent that I clipped it out to keep in case I ever had a son. Well, years later, I have a son. But I have since moved a gazillion times and across several continents, and I no longer have that precious piece of paper.

My son is only 9 months old, but I am worried that by the time he is a teenager, you will have retired to some fancy ranch where you will spend your days raising organic cattle, being nasty to the local genetically-modified-wheat farmers, and passing the afternoons on the porch sipping gin from a teacup while terrorizing the local boys with a Super Soaker.

I digress: Any chance you could reprint your advice for teenage boys? I know that I, my partner, and my son will all appreciate it.
GGG Lady Lover And Mama

Congrats on the birth of your son, GGGLLAM, and here, at your request, is my advice for the hard-up teenage boy:

You’re having a hard time getting girls. That sucks. I remember what it was like when I ...

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August 4, 2010

My boyfriend and I have “history.” We dated casually and weren’t ready to stop seeing other people, so we had an open relationship. This phase was awful: lots of fights, a couple minor breakups, and eventually I called it quits for good, cutting off all contact. A month later, we started talking again and decided to commit for reals. No fucking around this time. This is his first monogamous relationship, and while he claims to miss the variety, he says he wouldn’t trade having me for having it.

Here’s my question: I’d like to have a three-way. Will it open up the vault? While I trust him, I don’t want to make it seem like it’s okay for him to fuck around again. Is this too dangerous a proposition?
One More Time

Full disclosure: I’m on an airplane, under the influence, and in coach (which means I’m typing with my computer resting on my chest). So this week’s advice is sure to be extra-sucky.

Okay, OMT, if you make the mistake of having a three-way, you could wind up fighting, breaking up, and calling it quits all over again. But all ...

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July 28, 2010

Ever since hearing you say on your podcast that all men use porn, I have had a burning question: What about us women? If all men get a pass to have this whole other sex life, which is (mostly) external to their partnerships and is sexually satisfying, then I think all women should have a pass as well. Ideally, it would be a pass to enjoy something universally arousing to all women, something that would sexually satisfy us, but it wouldn’t be something that turns most men on; perhaps it might even repulse them.

If there were something that met my criteria, I wonder how it would play out in our relationships? Also, I am not sure what it could be, as women are a little bit more complicated.
Desires Erotic Balance

Something women enjoy but men do not… something erotic… a free pass for just the ladies… something that repulses most men…

Cupcakes?

The now-ubiquitous cupcake isn’t explicitly sexual, I realize, but our culture does encourage people—women in particular—to sublimate their erotic desires by stuffing their faces with food. And most of those squat, round, and pink-frosted things look, to my jaded eyes, like so ...

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July 21, 2010

I was recently told that I am being puritanical and self-righteous because I can’t get over the fact that my partner spends a good deal of time seeking out pictures of very young girls to masturbate to. Nothing illegal, he says, but still…

He admits to having a 20-year-plus addiction to porn, and with that particular addiction, he says, comes the need to continue upping the taboo factor in order to get off. I can understand the natural escalation from traditional porn to something more risqué, and I’m fine with him watching chicks with dicks defecate in each other’s mouths until his eyes bleed, because those she-males are consenting adults.

Eight-year-old girls, however, are innocents preyed upon by pedophiles and people with child-lust disorders, in my opinion, and I think a rational adult, even in the throes of sexual whimsy, should recognize that boundary and not cross it. My question is this: Is it considered typical sexual behavior for a guy who’s really into porn to seek out YouTube videos of 10-year-old ballerinas without having any kind of pathological inclination toward pedophilia?

He Says I’ve Turned Into My Born-Again-Christian Mother

“Whimsy” is not a word ...

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July 14, 2010

My boss/CEO lives and works in a different city, but most of her mail arrives at my office because it is the company’s official address. I routinely open mail and packages addressed to her. Usually they contain documents for me to handle or software for me to install, but today I opened a package with her name on it to find something completely different: a pair of vibrating panties.

Both the billing address and shipping address are the same, so I’m guessing she purchased them on her company card.

I know this is more of a business-etiquette question, but do your amazing sex-advice skills provide you with any ideas on how I should handle this? It will be very obvious that the package has been opened, even if I try to tape it back up and send it to her home address. But if I do nothing, sooner or later she’s going to wonder where her shipment is.

We’re a small, casual company and she’s a pretty confident and outgoing person, but I can’t really predict how she will react to this. Would it be weird for me to just be up-front about ...

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July 7, 2010

My husband of eight years confessed to wanting to watch me with another man. I asked if he meant it. He said yes. I asked if he wanted me to set it up. He said yes. I found a guy, and he agreed to a full STD screening—at my husband’s suggestion and our expense—so that we wouldn’t have to use condoms.

I was worried about how my husband would feel. But he loved every minute of it—he loved it a little too much.

My husband had sex with me after our “guest” left. I still had our guest’s semen inside me. Is my husband gay? Is that what cuckolding is all about? He didn’t touch the other guy, but what the fuck?
Spouse Expressing Concern Over Newly Disclosed Sexuality

“Far from being an indication of homosexuality, your husband’s turn-on goes back to the roots of male heterosexual experience,” says Christopher Ryan, coauthor of Sex At Dawn: The Prehistoric Origins Of Modern Sexuality. “Human beings evolved in very intimate groups where sex often involved multiple partners.”

Before Ryan walks us through what’s so straight about your husband dipping his dick in another ...

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June 30, 2010

I am a married white guy in my 50s. My wife and I do some role-playing where I am “Ted,” her real-life father. In her script, I yell at my “bad daughter” (my wife) over some infraction and send her to her room. Later on, I sneak in and tell her that she could “make Daddy very happy” if we were to do some “secret, special things” together. I usually end up fingering her still-virginal butt while “forcing” her to suck my dick. Then I roll her over and rape the hell out of her.

I’m being GGG, and she absolutely gets off on it. We’ve done this scene a few times, with increasing frequency, following her script every time. I do have some concerns, Dan: 1) It’s creepy, and 2) I’m worried that this might all be “based on a true story.”

What to do? Keep a good thing going, or confront her about her father? I’m going to feel like an idiot if it’s all just a harmless fantasy.
Concerned “Father”

What if it is based on a true story?

Let’s suppose your wife was raped by her actual father and ...

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June 23, 2010

My friend is a gay-identified FTM. He’s hot, he’s cute, and above the waist, you would never guess what he’s got down below. We love to kiss and cuddle, and from my end, his blowjobs are great. The problem is that I have no idea how to reciprocate. He isn’t into anal (why would he be, without a prostate?), there’s no cock for me to suck, and what he does have down below doesn’t interest either of us.

Do you have any ideas on how I could turn him on and get him off? It’s starting to frustrate me. Getting bottom work done is a long way off with the current finances.
Sent From The Savage Love App For iPhone

“Your FTM partner has to become comfortable with his own body before you can attempt to satisfy him sexually,” says Buck Angel, transsexual FTM porn star, a.k.a. “the man with a pussy.” “Your partner will need to share with you what his needs are. Nobody should be expected to guess at what his partner wants. Communication is important, regardless of gender or sexuality.”

I agree 100 percent with Buck—what he ...

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June 16, 2010

I’m a woman in my 20s, and I’ve been dating the love of my life for two years now. We are incredibly happy except for—guess!—we have different sex drives. When we first started dating, I initiated sex all the time and enjoyed it, but as soon as I started on birth control, my libido evaporated. After a nightmarish year of trying different methods, arguing with doctors, and hurt feelings, I decided that it wasn’t worth it, and we’ve stopped using any hormonal birth control. (We’re using condoms.)

But months later, I still have almost no interest in sex or masturbation. We have sex once or twice a week, but it’s physically boring. I put on my game face and endure it. I enjoy pleasing him, but it does nothing for me. It hurts him that I am not interested in sex and that he can’t arouse or please me. I want us to have a healthy sex life, because I love him and he’s worth it. Could this still be the birth control? Did I somehow flip the OFF switch?

Please help, Dan. My doctors are all sex-negative and don ...

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June 9, 2010

My husband was 28 when I met him, and a virgin. When we started having sex, he opened up about being “different.” He wanted to wear panties, he wanted me to have sex with other men, he wanted me to make fun of his tiny penis. Didn’t love the stuff, but whatever. Now it’s a thousand times worse. He goes to Victoria’s Secret and tells the salesgirls he is being punished by his wife for wearing her panties and that I am “forcing him” to go buy some of his own. He told me he could see our neighbor undressing, so he tried to contact her to see if she wanted to humiliate him while he was dressed as a woman. He thankfully failed to contact her. And I recently found an e-mail in which he “confessed” to a female coworker that he had a deep, dark, embarrassing secret he wanted to tell her. I confronted him, and he said he was going to tell her about me “forcing him” to wear panties and ask if she wanted to see his tiny penis!

He sees nothing wrong with this behavior. I feel like he is a fucking ...

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June 2, 2010

I’m a straight male college student in a relationship, which had been going great. The only incongruity was that, for a religious reason, I don’t want to have penetrative vaginal sex before marriage. I’m up for anything else—I would eat her out, piss on her, whatever else—but not vaginal sex. I made this clear at the beginning. My girlfriend started bringing up how she wanted to have “actual” sex. I told her, “I love you, and if you need to fuck other guys, go for it.” To my relief, she was completely repulsed and offended by the suggestion.

A week later, she confessed that she had gone ahead and slept with someone. I had no idea I would be this hurt. I feel like I can’t trust her now, and I can’t bring myself to sleep in her bed anymore. I feel like a hypocrite, since I brought up the idea of her sleeping with someone else in the first place. But I was unprepared for the reality, since she berated me for making the proposal at all. Still, I feel like I don’t have a leg to stand on here; I ...

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May 26, 2010

Where can a straight guy find a transsexual woman who is NOT a hooker and just wants to be friends (with benefits)? I know of one club where they hang, but they are mostly hookers there. I would like to go someplace where I could meet one and see if we could hit it off and go from there. I know they are out there, but I just can’t find them! Help a brother out! PLEASE! PLEASE! PLEASE!
Lonely Tranny Lover

If what you’re looking for is a transsexual who’ll allow you to fuck her—or who’ll fuck you—but who won’t require you to have an actual relationship with her, LTL, then you’ll have to pay some nice woman for her time and her emotional distress, like all the other straight guys out there into MTFs. Why do they have to pay? Because, LTL, it’s kinda shredding to sexually service someone who’s embarrassed to be seen in public with you. Just ask any openly gay man dating a closet case and/or a Catholic priest, or any BBW sleeping with a man who’s married to a rail-thin trophy wife he ...

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