The First Embarrassing Romantic Gesture
In Grade Seven I was, as I continue to be today, woeful in all of my interactions with women. Now, I know to keep my mouth shut—in Grade Seven, the idea genuinely hadn’t occurred to me yet. While my colleagues had been raised on a diet of football and cars, I had an emotional affinity with my mother, a mother who encouraged blind romantic ambitions in me for no good reason. Why else would she have shown me An Affair To Remember, or Casablanca before I was 10?
The girl of my potential affections was lovely—musical, pretty and, against all odds, nice to me, or so I perceived it. Thinking back, the only time I can remember us interacting was when she had asked if my “face was ok” after a bad outbreak of acne. I must have confused that for interest at the time.
But I had no way in. No common interest by which to initiate the cosmetic niceties that eventually give way to a caring relationship. While she was a prolific violinist, I had no sense of rhythm or music (a teacher had once told me to abandon musical ambitions “for everyone’s sake”); while she was nice and gregarious, I was afraid of both crowds and being alone.
I eventually decided the easiest way to get her attention without actually talking to her was also the most unnecessarily complex. My student council was selling “candy-grams”—little pieces of chocolate that would be attached to heart-shaped notes—to raise money. I convinced myself that this would be my vessel for initiating contact, though I was too afraid to make a direct pitch for her affections. Instead, I included what I perceived to be a “code” for my name—instead of actually writing my name out, I would include numbers that corresponded with the letter in the alphabet of my first name and last initial. I could just imagine it—her reading the numbers, puzzled yet oddly excited, and, in a moment of epiphany, realizing that I was the mystery man of her dreams.
So I went ahead with it, assuming my cleverness would be rewarded, and my deep sense of romanticism would immediately sweep my girl off her feet. Little did I appreciate how badly publicized the whole “candy-gram” program would be and that mine would, in fact, be the only candy-gram purchased that year, making its delivery to her classroom an uncomfortably personal affair. Worse yet, I did not realize that my “code” should have been proof read, and that by putting a “04” as my last number instead of a “02”, my friend “Chris D.” would be accused of sending the message (“at least she figured it out,” I would later lament). Feeling guilty, I had to eventually fess up to the girl that I was responsible for the message. It was, and remains, the most uncomfortable conversation of my life.
I’ve never been one for subtlety, and this did little to improve the fine skills of my emotional intelligence. It would be four years before I went on a proper date, but by then I had at least realized that women like directness. Or at least that they dislike creepy heart notes with cryptic numbers attached to Hershey’s kisses sent to them in class.
The First Time I Got Fingered
I was 17 the first time I got fingered, although it wasn’t until months later that I would come to enjoy such a gesture. It was after my Grade 12 semi-formal winter dance (I, uh, grew up in Oakville?), in some kid’s mansion on Lake Ontario. I was determined to kiss this one guy who I’ll henceforth refer to as Ron, who was skinnier than me, shorter than me, listened to a lot of hip-hop and was super enthusiastic about watching sports. It was back in the days when I still thought guys who wore basketball jerseys over t-shirts were acceptable conquests; in my defence, there’s not a ton of selection at prep school (thank God for MySpace).
Things didn’t work out so well with Ron, because he showed up at the party with a girl on each arm (probably a good argument for why upper-class high school boys shouldn’t be allowed to watch Entourage). Enraged, I got a cigarette from this guy I’ll nickname Big Bird, because he’s tall, blonde, and has a massive nose. I had never smoked a cigarette before and this seemed like a good time to start. Big Bird seemed to understand my problems, and did I want to go into the bedroom with him so we could talk about our feelings? I’m not sure what led me to say yes, whether it was my desperation for a man’s touch, or my first dose of nicotine, but off I went. (Here’s where I’ll mention that I’d been drinking warm Goldschlager from a flask all night.) So the next thing I knew we were tangled on some leather loveseat as he mauled my face and struggled to pull my tights off. You’d think a 17-year-old boy would have watched enough porn to be able to locate the clitoris, or that he’d at least trim his nails beforehand. It was like he was trying to play the bongo drums. Who slaps a vagina right away? It was terrible! I remember lying there and thinking, “I must be a lesbian.”
Yeah, the situation couldn’t have gotten much worse, but it did. Big Bird forgot to lock the door to the bedroom, and about 30 seconds later, five dudes burst into the room. My vagina, never before exposed to a male, was now on display to six of them. Quickly closing my legs and screaming “GET THE FUCK OUT!” I managed to regain poise, quickly getting the fuck out of there myself. The following Monday, a rumour was spread that they had walked in on me losing my virginity. So yeah, I’m pretty happy to be out of high school.
The First Kiss
He didn’t remember our first time.
I don’t blame him entirely. After that fateful night, I didn’t see Michael again for years. During that period, I mostly shied away from other guys. Occasionally, I’d go dancing with Johnny, who sent me love notes with my name spelled wrong, or Aaron, whose punk-rock spikes freaked out my parents satisfactorily. I never felt much for these boys: somewhat precociously taking a page from Vonnegut, I was loving whoever was around to be loved. Michael, though, was the real thing.
We’d been riding a motorcycle borrowed for the evening from an acquaintance. Steppenwolf was blasting in the background, and we lip-synced every word. (Fire all of your guns at once, and explode into space!) Michael was the most beautiful boy I’d ever seen, with steely blue eyes and a perfect left dimple. I quietly admired him all summer long, while all the other girls chased him more resolutely. In the end, he told me, that’s why he chose me—he liked that I was quiet. I blushed, unable to come up with a sufficiently mysterious response. Luckily, he wasn’t expecting one, and he planted his lips right on mine.
Now, when you’re eight years old, this kind of thing is a big deal. But the fact that the whole scene (motorcycle, Steppenwolf, and all) had occurred during a skit at summer camp made the whole episode more incredible. My first kiss had been watched by a crowd! As the summer faded away, so did my attachment to Michael, but I held strong to the mythology of the kiss.
I ran into him at a party in Grade 10, the type of suburban shindig that almost always requires cream soda and Green Day playlists. Michael was as cute as ever, though he hadn’t grown —I still towered over him at five-foot-three. In my 15-year-old mind, fate had reunited us for a reason, and we were soon Frenching behind a staircase. I thought I was being tremendously coy when I whispered, “You’re even hotter than when we met!” But Michael replied confusedly, “10 minutes ago?”
Maybe he didn’t make the connection that I was the same girl he’d kissed on a motorcycle when we were eight. Or maybe he’d stolen smooches from all of my grade school pals in 1996, and I was nothing special. So I tried to forget the Michael of my first kiss. There was a pressing matter at hand, and his name was Michael, too.
The First Time Doing What They Don’t Describe In Health Class
Every high school student feels a mounting pressure to lose their virginity by the end of senior year (I am, admittedly, of the American Pie generation). The latter part of my high school experience consisted of so many of my “bro”-friends regaling me and our smoker’s group with tales of their first time having sex, I began to feel left out. I met my high school boyfriend on Myspace (yes, I’m also of the MySpace generation). He went to the high school across the street from mine. Like any good homosexual high school relationship, mine consisted of hanging out in this dude’s basement on weeknights, watching our favourite MTV series The Hills, cuddling, making out, and the occasional and abrupt session of oral sex on his couch. But my stories during the post-first period smoke break the next morning never seemed to stand up to my heterosexual buds.
Finally, after dating this dude for four months, I felt like it was time, you know, to consummate our adolescent romance. That day happened to be Victoria Day, 2007. On paper, it was actually really romantic. We started off the evening with our usual channel 50-something viewing and cuddling, where we feigned interest, passion, and moved, tongues locked, into his bedroom. He lit some candles, dimmed his fluorescent bedroom light, and put on his pre-made playlist of Death Cab for Cutie. Outside his basement-bedroom window, his younger siblings were in the backyard lighting off fireworks in celebration of the holiday. On my back, I was prepared for something monumental, something romantic, something that would validate my sexuality, and effort towards this young man. What I was not prepared for was the pain. Not understanding the dynamics of anal sex, or the sacrifice made by the “bottom,” I realize now that no amount of lube could have made the loss of my virginity any less excruciating. With Ben Gibbard singing softly in the background, my boyfriend tried awkwardly to get his fully erect, nearly foot-long genitalia into my…well I’m sure you understand how that goes. Needless to say, despite Transatlanticism, I basically passed out from the pain and he freaked out. I’ve ripped open my eyelid and undergone gum surgery, and none of these experiences compare to the pain felt in my bowels—not just in the moment, but for two days after. Yeah, I got a story out of it, but my buddies the next day could do nothing but laugh hysterically at my horror story of losing my virginity. My boyfriend and I broke up a week later.
The First Time I Had Sex With Myself
The first time I had sex with myself was about a year and a half after I had lost my virginity proper. I was 19-years-old. Prior to that wonderful, transcendent afternoon I had had, as relationships will allow, successful intercourse countless times. But ever since high school, non-copulative activities, such as handjobs and blowjobs, had always been miserable failures. Hands, with their hard, clumsy grip, and mouths, with their unwieldy, serpentine tongues, made me go limp faster than I could say “It’s not you, I promise, I’m just tired, please don’t leave me.” My penis wanted vagina, and only vagina. So it was that I had my first real orgasm the first time I had sex, rendering me hopelessly and destructively dependant on the affections of women.
It’s not that I had never tried masturbating. I just, unlike my friends, didn’t persevere. For a period of about six months when I was 13 one of my best friends would call me up every Saturday night. As we ogled the women of Sex and the City in our separate basements he would jerk himself off while I, in the spirit of good sportsmanship, made all the appropriate grunts, sighs, and “Oh yeah, Charlotte, fuck me’s.” It was no foreskin off my nob—you can’t miss what you haven’t had.
In March 2006, I lay bored in bed and decided to give autoeroticism another try. As always I had no trouble getting erect; I was single at the time and my pent-up sexual energy was back to its Herculean adolescent levels. But as usual, I felt nothing but discomfort after that. Suddenly, the (some would say obvious) epiphany came: I should imitate a vagina. So, imagining how my penis felt inside someone, I started experimenting with angle, force, and rhythm until everything clicked at once and, in a moment of pure and true ecstasy, I exploded all over my stomach and chest. “Fuck!” I cried, as much from joy as from the realization that I had stained one of my favourite t-shirts. About five minutes later I tried again, just to make sure it wasn’t a fluke, and again—again! —was able to give myself what previously I had only been able to get from someone else. I thought, free at last, free at last, thank God almighty I am free at last…and I’ve been blissfully independent ever since.
The Last Kind Gesture
Last year, I was sitting on the subway, as were many other people. But unlike everyone else, I was in an army uniform with all my military equipment. There was a general in town so he needed to be acknowledged by members of the Canadian Forces like myself who couldn’t have cared less about him but still needed to respect the rank. I had forgotten my iPod so I started to polish my boots. I knew the civilians were watching me, they always watch me, even if I’m just sitting there looking at the subway ads. All of them seem to think that I don’t notice them outrightly staring at me. Apparently there is something very intriguing about a young woman in uniform.
Not too far from me was a man in a typical business suit holding a single rose on top of his briefcase. That’s when I realized it was Valentine’s Day. Not only was I single, but I was going to a base on a Friday evening and on Valentine’s Day.
My stop was coming up so I got up, heading towards the subway doors just as they opened. All I heard were the fast-paced footsteps behind me. For a split second all I could think of is, “Great, someone wants to mug this soldier.”
I stopped and looked behind me. Standing there was the businessman. He handed me the rose, smiled and said, “Happy Valentine’s Day.” I couldn’t help but smile at him like an idiot. I thanked him. He smiled and walked away.
The Last Time I Felt Bad After Sex
The last time I felt bad after sex was in El Jadida, the coastal town where Welles shot Othello. I saw the cistern, approached fading minarets, took grey photographs of a cloaked man walking his bicycle along a thin ocean wall. Outside a supermarket I met a young man named H—-. “Let’s go to a club,” he said, “let’s get some girls.” “Not tonight,” I said. “Tomorrow.” The next day we met at the beach. I asked if he had any condoms and he pulled one out of the pocket of his jeans. It was dry, unpackaged, and had a bit of sand in it. He turned it inside out and brushed it off as we walked.
Outside the small concrete building where H—- lived stood a large woman in a djellaba with whom we exchanged pleasantries. We went through a door, then ducked under a hanging sheet into a room with some cushions on the floor and an old tape deck. We sat down and a boy of 12 came in with tea. Pictures of girls were produced. Phone calls were made. No one was available. I gave the boy money and he went out and bought red wine, vodka, cigarettes, and condoms. We drank and listened to cassette tapes (gnaoua, Rod Stewart). More phone calls. No girls. H—- stumbled outside and I heard him persuading, pleading in whispered tones with the woman out there. Finally she came in, sullen and shy. H—- went first, while I waited on the other side of the sheet, sipping wine. He came out smiling and perspiring, then it was my turn.
She was fat and middle-aged. I tried to get inside of her but it was awkward. She was too tight, too afraid. I wondered how H—- had managed. I took my condom off and she sucked me for awhile and then I jerked off until I came. Her faced was flushed and she didn’t make eye contact. After she left we drank more and then H—-’s older brother came home. He had a chiselled face and gentle eyes. He showed us a bag of heroin he’d found on the street. We cooked some chicken on a gas burner and a neighborhood girl of about 15 came in and sat on the floor to eat with us. We tried to get her to drink but she wouldn’t. Her eyes were dark and really shiny.
The Last Time I Indulge Someone Else’s Fantasy
A long time ago, I was dating an older guy who liked to discuss the multitude of his previous sexual experiences (being very gullible, I only doubted their accuracy after we broke up, when I realized that his threesome story sounded exactly like every porn flick ever made). When the relationship started falling apart, I thought that maybe I could salvage it by indulging in one of his fantasies that my younger, less experienced mind had previously felt weird about.
Thus, ignoring my dime-store feminist (and intellectual) instincts, I dressed up as a schoolgirl to try to please this guy, who had a bit of a “barely-legal” fetish going on. But when I presented myself, complete with shortened kilt and itchy knee socks, he couldn’t even sustain an erection. That night as I passed out drunk, lonely, and sexually unsatisfied, I could swear I heard Gloria Steinem whisper, “I told you so.”
The Last Time I Watched Porn
When I was a small child, about seven or eight years old, I discovered pornography. My grandparents apparently had a healthy interest in sex —their house is still filled with novelty items like cute modernist statues of two dogs having sex while their masters held them on leashes—and when I was a kid, my relatives really let it all hang out. I guess they figured that no kid would ever understand these things, but once I pulled a porno catalog off the kitchen counter and ran with it up to the guest room. I could feel my mind expanding as I poured over page after page of ludicrously large breast implants and knee-length dicks (this was the early ‘90s so there was a shininess to it all). I thought to myself, “No adults I know have parts like this!” This was still a few years before I understood penetration, so I thought that sexuality was a cartoonish display of the weirdest things adults could imagine. I had no way of understanding any of these images, but somehow they struck a major chord. I suppose it was cable TV that trained me to understand sexuality, and it seemed like I knew what to think from all the Janet Jackson music videos and car ads. From that moment on I knew: sex was awesome. I immediately showed the images to my little brother, who was about four, and began an odyssey for every vestige of porno that my underdeveloped hands could grasp. All the while I knew that if an adult caught me with any porn, my life would immediately end from sheer embarrassment.
But my desire to see and hear the performance of sex was too great. One evening, when the entire family was gathered at my grandparents’ house for some holiday, my brothers, cousins, and I were watching TV in my grandparent’s bedroom, and I had the clicker. While surfing, I found the scrambled porn channel and was immediately enthralled. My brothers and cousins were grossed out (they are all younger than me, so just imagine a room full of kids between the ages of two and eight watching scrambled porn together), and kept trying to steal the clicker to switch the TV back to Nickelodeon. But I asserted my dominance as the eldest grandchild and continued to jump on the bed and watch porn. Pretty soon my younger brother ran into the kitchen where the adults were gathered and yelled, “Daniel won’t stop watching the sex channel!” All of my relatives erupted into a loud and shrill laughter. I was mortified. It wasn’t too long before I decided that pornography was a juvenile activity, and that I would never have anything to do with it ever again.
The Last Time I Faked An Orgasm
If lesbian relationships are supposedly more egalitarian than their heterosexual counterparts, then why is it that I’ve had to fake so many orgasms? Perhaps it would be more efficient to not critique the structure of lesbian couplings, but rather my abysmal taste in women.
My problem is that I never follow my tiny, misshapen heart, or even my hairy crotch—I am drawn to women who are ridiculous by virtue and never amount to anything more than fodder.
There was one girl I briefly courted, only because she quickly designated herself as the token idiot in a friend’s class, and I had to incessantly hear about her antics. Later, trapped within the confines of her miniature childhood bed with her parents a few doors away, she asked me to pretend as if I were eating her breasts. This sentiment both shocked and appalled me, never being one to fetishize food or big tits. Before I could refuse, she sat on top of me, shoving her fleshy mounds into my mouth when she realized I wasn’t going to eagerly begin chomping on my own accord. Her orgasm tally would total three by the end of the night while I was scarcely able to reach arousal.
At my first and last kegger in someone’s dirty basement, I engaged in a threesome with two ladies—one akin to a rabid dog, the other a militant feminist. During this tryst, the aforementioned canine descendent bit on my nipple so ferociously that it actually split open. Minutes later, a head popped into the room to ogle the girl-on-girl cesspool, whipped their dick out, and pissed all over the carpet. From there, I ran with unfastened pants saddling my hips out into the night, sans orgasm.
Most recently, I got out of a quasi long-term relationship. We mostly tackled sex in a very generic, get ‘er done kind of way. One day, while wearing my strap-on, she requested I fuck her doggy style for the first time. As she assumed the position, I noticed remnants of shit in her ass that killed my libido to the point where I swear my silicone dildo went flaccid. I managed to feign fatigue, narrowly escaping an unwanted foray into scat play.
Lately, I have been logging onto XTube to help me get off, and for the first time, have no problems achieving climax.
The Last Time I Felt That Way
I met her on Halloween. My friend had bumped into her on the street outside of the bar and he was apologizing to her. I stumbled outside, drunk, and walked up to the two of them. I assumed that they were friends and I began talking to her as he left. She was going to the same party as us and walked beside me. Neither of us were dressed up as anything and we stood outside the party talking for hours while everyone we knew was inside, dancing, drinking, and being high. At one point she took my hand and led me through the party to find some water and then watched as I drank it. At the end of the night she gave me her number. When I tried to kiss her she backed away and, acting as if I hadn’t, she smiled.
A few days later we hung out. We went to the liquor store near her house and bought a bottle of cheap red wine. We drank it at her apartment, the top two floors of an old house on Dovercourt, where she lived with two roommates. I felt strange. I was 23 years old, freshly graduated, no job. She was 27, immigrated to Toronto when she was 13. She worked in a kitchen, and she had dropped out of art school.
On the third night that we’d hung out she took me to her bedroom and we made out on her bed and began to fool around. I undid her pants and put two fingers inside of her while we kissed, but she stopped me. We lay in her bed and she told me that we couldn’t be lovers, but that she wanted to be my friend, and that she never wanted to be anyone’s friend. I was confused and frustrated but I looked at her face and her big black eyes, told her that I didn’t want to be friends with her and left.
I kept seeing her for a few months after that. We would go out and drink and kiss and hold hands and we would fool around on the couch in her living room, but I never saw her bedroom again. I would fall asleep with her, wake up with my contacts still in, eight missed calls from the cab that I had phoned hours before. I would stumble out of her house on Sunday mornings, still drunk, walking past groups of people going to church. We had sad conversations about life and she constantly depressed me, but I felt comfort when I was with her. I saw her every other day. We made food and jokes and I kissed her neck and she smiled the most beautiful smile that I had ever seen. I tried to explain to her how I felt, but couldn’t really put it into words. I’m sure that she knew what I meant, but she would just look at me and smile and I’d stammer on to something else.
So, it fell apart. She started brushing me off. We hung out less. I went out of town for the Christmas holidays. We stopped talking. I thought about her constantly, but I didn’t call her. Weeks passed. Eventually I just assumed that I would never see her again, and I never did.
I’ve never been able to completely forget her and I’m always wondering if I’ll run into her in this small little town. But I never do.
