Bum Deal

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Bum Deal

Dear Dan:

I'm a twentysomething professional snowboarder. I have a problem that I don't really have anybody to talk to about. When I jerk it, I have to put a finger in my asshole to finish. Plain and simple, that's the only way I can come. I can't even come in a girl's pussy without sneaking a finger in my back door. I go to great lengths to hide it — push her head in a pillow, etc. — because I don't want them to think I'm gay. (I have no problem with other people being gay, just FYI. It's just that you do not want snowboard groupies thinking you're gay. Girls talk, and then you never get laid again and all of your bros find out you're sticking things up your butt.) How do I learn to come without prostate stimulation?

Butt-Using Manly Man Entirely Distressed

Get a butt plug. It's a butt toy that your sphincter muscles hold in place — picture a small lava lamp that fits in your ass — and once you get it in, BUMMED, it won't slip out. Provided your groupiefriends aren't touching your asshole or looking directly at it, they won't even know it's there. And a butt plug might help you break the strong mental association you've made between finger-in-hole and climaxing. There are lots of straight guys like you out there. Your sexuality isn't the problem; your need for prostate stimulation isn't the problem. The problem is your shame and your desire to hide this aspect of your sexuality from your groupies and your bros. You may not be gay, BUMMED, but you do need to come out.

Dear Dan:

I've been confused about my sexuality for two years. I am a 22-year-old female. I liked guys when I was in school, but then I developed a HUGE crush on Tegan and Sara when I was nearly 20. I like the idea of being with women, but I have never had a major crush on anyone since. So I'm really confused over what my sexual orientation actually is. I know many hetero-identifying people experience same-sex crushes, but can someone's whole sexual orientation just change overnight? My confusion is compounded by the fact that I've never even held someone's hand, been kissed, or done anything else. I really want to experience such things and generally just stop feeling like a complete loser. Any help appreciated! Awfully Nervous Over Newness

"When I was young, I dated boys," said Tegan Quin, one half of the popular indie duo that prompted you to question your sexuality. "I never thought about love or being 'in love.' And I never thought about sexuality. Until I kissed a girl. Then I knew who I really was. I was gay."

Oh, hey, I hope you don't mind that I shared your letter with Tegan and Sara, ANON. I figured you might appreciate getting some advice directly from your potentially life-altering crush.

Like you, ANON, Tegan used to assume she was straight. "I'd gone most of my teens crushing on guys like Jared Leto, thinking that must make me straight," says Tegan. "Even though secretly I was dreaming of make-outs with Claire Danes. I thought my crush on Jared Leto vetoed my secret girl crush on Claire Danes. Maybe that was society weighing down on me. Perhaps it was peer pressure keeping me inside the lines of heterosexuality. Or, likely, I just liked them both."

Based on your letter, ANON, Tegan suspects that you might like both. "Sexuality is not hard lines," says Tegan. "Some people know their whole lives who they are. Some people don't. My advice: Go and kiss a girl, go and hold a boy's hand. Don't worry about who you are until you find out what you like. Maybe you'll like both — and yay if that's the way it turns out, because that means you have twice as many people to fall in love with."

And while Tegan doesn't think a person's sexuality can change overnight, she believes — she knows from personal experience — that a person's awareness of their sexuality can change overnight. "You can have an awakening," says Tegan. "Like I did when I first kissed a girl. A whole new world can absolutely be waiting for you if you end up feeling up to exploring it. Good luck!"

I've been with my boyfriend since I was 15. I'm 20 now. In all the time we've been together, I've never had an orgasm. For a long time, I wanted to get a vibrator, but my boyfriend hated that idea and never wanted me to get one because he says he already feels like crap that he can't get me off. Recently, I thought, "What the hell — I want to see what happens!" So I bought one on my own. The very first time I used it, I got off in two minutes. Now I feel stupid for not buying one sooner. My question is...How do I tell him? Should I tell him? He always wanted to be the first person to give me an orgasm, and as far as he knows, I still haven't had one.

Couldn't Wait Forever

Tell your boyfriend you bought a vibrator, CWF. If the boyfriend has a sad about your purchase — and your ability to climax (congrats!) — tell him that some women require the kind of intense, focused stimulation that only a vibrator can provide in order to get off, and, as it turns out, you're one of those women. And he can still be the first person to give you an orgasm: He can give you one with a vibrator in his hand. And if he acts like an insecure bitch about it, CWF, if he blows up or melts down, well...New vibrator, newly orgasmic—maybe it's time for a new boyfriend, too?

CONFIDENTIAL TO EVERYONE: Make porn! Details on HUMP!—the annual porn festival that I host in Seattle and Portland—are here: www.humpseattle.com. Films are limited to five minutes in length, they don't wind up on the internet, and you don't have to live in the Pacific Northwest to submit to HUMP!. And this year's grand prize is $5,000!

Find the Savage Lovecast (my weekly podcast) every Tuesday at thestranger.com/savage.

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Dear Dan:

I'm a gay man and a hunter with a gay boy who's a vegan. But he likes how I look in my camo, holding a rifle, so it works. Last fall, I went to Idaho and shot a black bear and a 13-point buck. A taxidermist mounted the buck's head, which hangs above my bed, and made the bear into a rug. Most people don't know this, but the head on a bearskin rug is entirely fake except for the fur. The skull, teeth, and tongue are plastic, and the eyes are glass. That bear's hardly a bear, if you catch me.

So we got the rug, and he liked it. Even wanted me to screw him spread-eagle on that rug — until he walked in while I was doing it with the bear. I rigged up the mouth with one of those Fleshlight things, pretty much as a joke, but my boy freaked out when he saw the bear giving me a blowjob of sorts. Called me sick and disgusting, and ever since then, he won't let me tie him up or beat him or anything. He says he's afraid I will kill him and then screw him. I keep telling him it was all just a game, but he won't believe it. What can I do?

Bear Grinned Anyway

What can you do? You mean besides send video of you and your bear in action to prove this isn't the most entertaining fake letter I've received since Michelle Obama invited me to dinner at Sarah Jessica Parker's apartment?

You can do this: You can draw a distinction between what was going on in that bear's mouth when your boyfriend walked in and what was going on in your head. When a man beats off, two things are kinda sorta happening simultaneously: what the man is doing with his dick and what the man is imagining he's doing with his dick. Guys who beat off using a clenched fist, for example, generally aren't clenched-fist fetishists; they're just horny and their fists are there and, say, Sarah Jessica Parker isn't. Fists provide necessary friction; imaginations provide sexy scenarios.

So your boyfriend walked in and saw you fucking the face of a dead bear. That's gonna look bad, BGA, even to a boyfriend who isn't vegan. So how do you fix it? By patiently explaining to your vegan boyfriend that while, yes, you were face-fucking a bear when he walked in on you, you weren't thinking about face-fucking a bear. Tell him you were thinking about him, and the bear's mouth was just a convenient place to wedge your vegan-boyfriend-substitute — i.e., your Fleshlight. Tell your boyfriend you don't entertain any murderous fantasies, tell him you only long to fuck living things, and tell him that Homo sapiens are the only animals you find attractive. Tell him all of that, even if not all of that is entirely true.

Dear Dan:

I'm a 17-year-old male, and I'm currently in a relationship with a girl who was sexually active before we got together. Me being a virgin, I think you can understand why I might be nervous when things get heated. I would like to engage in the act with her eventually, but I don't know if she wants a virgin fumbling around in bed with her. And it's not particularly manly to go to someone and basically say, "I'm not going to be good at this for a while." I feel she's ahead of me in experience. What's the best advice you could give me on the subject?

Nerves Entirely Wrecking Boy

If your girlfriend is close to you in age, NEWB, the odds that she's any good at sex are vanishingly slim, her prior sexual activity notwithstanding. Some people have a knack for sex, of course, but almost all teenagers are lousy at sex.

Now here's my advice: Chill the fuck out. Presumably, your girlfriend likes you and knows you're a virgin. Which means she knows you'll be a little nervous the first time you two have sex and that there's probably going to be some fumbling. But you wanna know a secret? Even sexually experienced adults — even adults who are really good at sex and have had tons of it — still get nervous, and there's no such thing as sex without some fumbling.

As for your concerns about seeming less than manly: You're bringin' the dick, NEWB, so you're the man. Your nerves won't render you dickless. If you're worried about displaying a manly confidence, well, you can still do that: Go into your first sexual experience confident that your girlfriend is into you and confident that she wants you, and be honestly and unapologetically who you are. Being yourself is far more manly than pretending to be someone or something you're not.

One last thing to do before you lose your virginity: Watch a weekend marathon of 16 and Pregnant on MTV. That show will inspire you to use condoms religiously and correctly, every single time, no matter what.

Dear Dan:

Following up on the letter about masturbating in the privacy of a public toilet stall: Guys are being banned from Multnomah County libraries in Portland, Oregon, for wanking in the supposed privacy of locked bathroom stalls. Facilities security officers peep through spaces between stall doors and write up reports that go into detail about "shiny liquids" spotted on offenders' hands, and those who are caught are excluded from the libraries for a year. I thought "sexual activity" required a partner and masturbation wasn't a crime if practiced in private — but tell that to the peeping uniformed officers working in the Central Library, aka "Portland's Crown Jewel." You can't go to a locked bathroom stall and rub one out, on pain of landing on the Excluded Patrons List as a masturbator. Victorian prudery lives.

Wanking In Private Environs

The letter writer who got caught wanking in a public toilet had taken pains to find an empty men's restroom on a deserted floor of an office building. He wanted to have his midday wank without disturbing or unnerving others. I don't think the same could be said for the men who are rubbing 'em out in the toilets of Portland's Central Library.

Look, I'm familiar with Portland's Central Library, WIPE; I wrote huge chunks of two of my books there. The toilets are crowded, and there's no way you can beat off in one without disturbing others. I don't have a problem with people rubbing 'em out — hello — but guys who get off in public toilets because they get off on public toilets are forcing other people to serve as props in their masturbatory fantasies. And that ain't cool.

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