High Times

...uit smoking? Then your boyfriend should find some other mouth to stuff his junk into. I’m sorry if that answer wasn’t very helpful. Or sympathetic. But smoking? Ick. Stop already. Yuck. Gross. Blech. Moving on, I was all set to do a really kick-ass column this week on cuckolding—wherein a straight man watches, or is told about, another man having sex with his wife or girlfriend—when one of my coworkers walked in with a pan of pumpkin pot cake. She told us that the cake was a complete failure as a drug; she had eaten two pieces the night before and didn’t get high at all. It was, however, pretty tasty cake, so she brought it in to work to share with everybody. Well, it seems that my coworker’s tolerance for THC is lots higher than mine. I had one little sliver of cake—maybe two—and now I’m so fucking baked I can hardly see my laptop. I shouldn’t be writing a column in this condition—goodness, what if someone were to actually take my advice?—but deadlines are deadlines and no editor will accept performance de-hancing drugs as an excuse for missing one. So I set aside the contentious cuckolding issue until next week and scrounged up a few questions that, even stoned, I can’t screw up. Or can I? As an 18-year-old Canadian gal, I feel compelled to tell you that you rock. On to business: Forgive me if this is an asinine question (how often do you hear that?), but how do I put it tactfully to my boyfriend of 1.5 years (and going alarmingly strong!) that I think I want to do him with a strap-on, in part because I’m pretty sure from things he’s said that he’d enjoy it? Is there even a way to put it non-bluntly? I would rather suggest it subtly if I can. Any information regarding obtaining said object, such as prices, sizes, etc., would also be much appreciated. Timid In Toronto You think you want to do him in the butt with a strap-on? Well, TIT, I think I speak for all straight boys everywhere when I say this: No straight boy is going to offer up his butt cherry to a girl who isn’t completely certain that pegging his ass is something she absolutely, positively wants to do. Not something she’s contemplating, TIT, not something she’s mulled over. Because the last thing a straight boy wants to hear once he’s face down, lubed up, and white knuckling the sides of the mattress is… “Naaaaaah, I guess not…” Actually, that’s the second-to-last thing he wants to hear. The very last thing he wants to hear is, “I didn’t know there would be so much blood.” So before you broach the subject, TIT, you’re going to need to commit. You need to present this idea to him with so much passion and fire that he understands that you wanna, that you gotta, fuck that beautiful little ass of his. Can you accomplish this while being tactful, non-blunt, and subtle? No, no, and no. There simply isn’t a tactful, non-blunt, subtle way to tell a man—any man, porn star or virgin, gay or straight—that you want to fuck his ass. There is no comforting euphemism, no way to soften the blow. It would be easier to drop “I’m pregnant” or “You have leukemia” or “That was my dad who got arrested for fucking a dead deer by the side of the road” into a casual conversation. You’re just going to have to let him have it, TIT, if you ever want to let him have it. As for pegging supplies and equipment, check out the goods at these fine websites: www.babeland.com, www.goodvibes.com, www.grandopening.com, www.comeasyouare.com, www.venusenvy.ca, and www.womynsware.com. I am a huge fan and never thought that I would be writing you a letter like this. But how can you denounce the actions of the Craigslist asshole who exposed all of those kinky fellas a few months back, then turn around and praise the actions of the male prostitute who outed Ted Haggard? Don’t get me wrong, I think Haggard is a hypocritical douchebag. But isn’t what the prostitute did worse than what the Craigslist asshole did, since sex workers are paid as much for privacy as they are for sex? Don’t Be A Hypocrite, Dan The crucial difference between the Craigslist asshole and Mike Jones, the escort who outed Haggard, is this: CLA outed men who were just minding their own kinky business and looking for people who shared their kinks. They were not powerful political or religious figures who were indulging in kinky sex while at the same time pushing laws that stripped other kinky folks of their right to wed, adopt, be free from harassment, etc. The men the CLA outed were not towering hypocrites—and Jones outed Haggard for his hypocrisy, not his homosexuality. I’m an average guy, not a big stud. My relationships with women have usually been long ones, never quick affairs or one-night stands. But there is this woman at work who, little by little, I have become attracted to. I have been having dreams, real-hot fantasies, about her. I found out she is going to leave her job and pretty much move away. I probably won’t see her again. Any suggestions on how I can approach this without sounding like an asshole? Clueless On The Job Nope. All unwelcome advances are made by assholes, COTJ, while all welcome advances are made by non-assholes. But since it is the reaction of the advanced-upon that determines asshole status (i.e., if she wants to fuck you then you’re not an asshole), and since you can’t know if an advance is unwelcome until after you’ve made it, you have to risk sounding like an asshole or you’ll never get laid. No one ever gets laid without sounding like an asshole every once in a while. So are you an asshole? There’s only one way to find out: Hit on her. Be respectful and upbeat about it, and do it at an appropriate moment (after-work drinks?), and wait until she’s no longer employed at the place where you work, particularly if she works under you. But risk sounding like an asshole, COTJ, or you’ll never get laid. A new Savage Love podcast is available for download every Tuesday at www.thestranger.com/savage. [email protected]