Toronto
4 min

First time for everything

Just because it's right doesn't make it easy

CONFUSED? Lube is the cure for every sexual crisis. Credit: Tatsu

Did your parents ever tell you about the joys of gay fucking when you were a kid? Did they encourage you not to bother with straight sex? Mine didn’t.



At 21, I had intercourse with a woman on her pull-out couch. I survived it by talking non-stop. Nothing fills the gaping void of passion like some witty repartee. The year was 1995 and I was young, closeted and worse, a virgin. I should’ve stayed one.



I refused to touch any part of her body without getting express permission first. As in, “Can I rub your vagina?” followed by some perfunctory heavy petting and a barrage of well-executed icebreakers and indiscriminate non sequiturs. “These percale sheets are stunning. Are they 180 thread-count?”



My attempts at dirty talk were wooden, which is more than I can say for my dick. Pronouncing it “va-GYNE-ah,” it was the only acceptable term for “down there” I could utter to a woman’s face. I had heard men say snatch or pussy – invariably preceded by moist or wet – but for me that was out of the question. I’d have been more at ease asking grandpa to pull out his honkin’ schlong.



The joyless debacle took 20 minutes. I faked orgasm and kissed her goodnight, insisting the condom remain on. For her safety, I emphasized.



“What if I roll over in my sleep and it touches you?” It was the only way I knew how to hide the fact that it was dry as a bone. The only female to ever lay naked with me again was the family cat.



Next year Drew happened in a dark student lounge at York’s Vanier residence. He was my first taste of all-the-way gay sex. He was a year my junior, but it was clear he’d done this kind of thing before. He had me bend over on the couch, which I discovered was to be the full extent of my participation in our little love-fest.



I figured this was how gay sex was supposed to go. What did I know? My single source of gay sex info had been Dr Ruth’s radio show, but her advice vaguely alternated between “masturbation” and “use a condom.” And if you’ve ever jerked off wearing a rubber just to see how it feels, you know it’s about as sexy as a Happy Meal.



Remember your first? I can’t forget, no matter how hard I try. How in God’s name does it feel, I wondered, to have anything other than shit pass through an area of my body that to this point has been off limits?



Drew explained it would hurt only at first, “But thenÂ….” He reached for a condom.



Hold on. What exactly does “But then…,” mean? But then… a Pez would come flying out from my throat? But then… I could tell my friends I knew first-hand what “Sit on this and rotate” feels like?



I never found out that night. I was too uptight, which roughly translates in gayspeak as “too tight.” Pickle so far up, no room left for the cucumber.



Drew tried to fuck me. My entire body froze, clenching every muscle as my sweaty fingers sharply dig into the fabric of the couch. It didn’t go in. I recalled an old cartoon: the Winnie The Pooh episode where Pooh eats too much honey and can’t shove his fat ass through Rabbit’s hole. Push, Pooh, push. Drew fumbled around for the lube bottle, which he was convinced was the problem.



(Lube, incidentally, is the cure to everything that ails a gay sexual crisis. Not going in? Add more lube. Not making you go Ahhh? Add more lube. Cat keeping you up at night? Add more lube.)



Before this fiasco, I’d given as much thought to my sphincter as I had my iliopsoas. Now it was all I could think about, trying to will it to relax. In gay sex, a sphincter’s the fucking gatekeeper. And it wasn’t budging. We’d have had better luck clearing passage by chanting, “open sesame.” Surely there was a rain dance for this kind of thing.



“Try to take your mind off it,” Drew urged. Indeed. How better to enjoy sex than to picture yourself not having it.



His advice duly noted, I brought my mind to a Hawaiian beach. Typical tropical locale: blue sky, warm breeze and a 10-pound stick of dynamite trying to wedge itself firmly up my ass. At this point, the only thing between us and carnal bliss was my sudden antipathy for buggery and a growing suspicion that gay sex was one big sham.



Drew suggested we change position. Yes, that was it. Perhaps if I lay on my side, angle my left leg 90 degrees to the right, and project my other leg toward the ceiling, we’d get it right. Maybe even pick up a Sumo match in Japan. But that failed, too.



By then, our youthful passion was replaced by a stubborn male insistence on unconditional victory. We either penetrate the enemy line or die trying. But we grew bored. A stomach grumbled loudly; neither of us would confess.



As Drew pointlessly poked away, my mind had wandered to my history paper due Monday. Did the prof want 2,000 words or 2,500? Poke. If I increase the font size from 12 point to 13 and, poke, poke, fatten the margins half an inch, would the prof notice? Poke, Poke.



Mission, finally, aborted. If it weren’t for a hastily scribbled journal (“Oooh, I think he’s the one!”), my subconscious would’ve blocked this incident – and the one with the girl – from memory.



If only my parents had warned me.