Love & Sex

Bad Sex: Bigger is Better

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Bad Sex: Bigger is Better

For her, size really did matter.

The date was going well until she told me how big her first had been.

The actual word she used almost made me choke on my pasta primavera. "Gi-noooor-mous," she said, facing her palms towards each other in a gesture usually used by self-aggrandizing fishermen. "It was really painful the first time, but I got used to it after a while. I had to."

As a general rule of thumb, one should never discuss the size of an ex-lover's penis on a first date. Actually, one should never discuss the size of an ex-lover's penis ever, unless it's to say how puny and unsatisfactory one found it. It is a matter of basic decency, for a man's ego is a fragile thing. I thought every woman knew this, the same way all men know not to bring up an ex's giant breasts. I didn't know what to say. How do you defend your penis' dignity without sounding like an insufferable brag? Or worse, an insecure brag?

"I thought that was how big all guys were," she continued, pushing her food around her plate. "I thought that was, like, normal. Plus he was into all this kinky stuff. He had me doing all kinds of crazy things 'cause I didn't know any better. I guess that's why I'm so free sexually. If I like you, I'm open to almost anything."

"Well, if we ever get together I am sure I will not disappoint," I stammered. Sheesh.

I wondered whether I should follow her down this rabbit hole. Was she flirting with me or challenging me? I could not tell. I remembered that thing teenage girls tell teenage boys about women deciding whether they'll sleep with you within ten seconds of your first meeting, and tried to recall if I'd been that impressive in the first ten seconds after we'd met. It was doubtful. Had I written something appealing in the two e-mails we had exchanged before our date? Nope, they were all business: let's meet here, at this time, I am looking forward to it, that sort of thing. As far as I could tell, I'd done very little to warrant this level of candor.

"Well, if we ever get together I am sure I will not disappoint," I stammered. Sheesh.

"Play your cards right and I may give you a chance," she replied.

Now that is how you flirt.

We had met a week earlier at a dinner party. One of those dinner parties that starts off with the best intentions — a group of recently graduated twenty-somethings get together to share a meal, discuss politics and religion and who got voted off what this week — and soon descends into a puerile game of spin-the-bottle once wine-sipping turns into vodka-guzzling.

She spun and got me twice; I got her once.

She called it destiny and told me not to fight it. Our last kiss lingered longer than it should have, and might have gone on indefinitely had there not been catcalls and whistling from the rest of the circle. At the end of the night, as I walked her to her car, she quite matter-of-factly said that since I had already reached first base, the least I could do was buy her dinner.

"Next week, Saturday, I'll be free," she said. "E-mail me."

Before she drove off she leaned out of the window and demanded another kiss.

"Mmmmmm," she said, "You taste like a new day."

A new day. It was like she was reading from a script. All I could manage in reply was an uneasy chuckle. She was as self-assured as I was self-conscious; uninhibited and outgoing. I was intoxicated. And way out of my league.

That was a week ago, a lifetime ago. I had since imagined a number of scenarios for our date, and they were all variations on the same theme: I win her over with my charming personality and/or sense of humour and/or unexpected sensitivity and/or impressive knowledge of wine. These fantasies all ended with a stellar performance in bed, but now, facing the gloomy reality of all the ginormous penises she was used to, my enthusiasm began to wane.

I tried steering the conversation towards areas in which any shortcomings could not be readily proved with hard empirical evidence, but she was relentless. She told me about her second boyfriend, Jan, who had a body to die for and was from Sweden or Denmark; her third, Peter, who was just a rebound and a bad idea; Clayton, with whom she stayed with far too long; Brett, who was so cute but so stupid. Then there was Malone, her most recent boyfriend. They'd broken up only a month before, and she wanted to forget him as soon as possible, which was why she was "putting herself out there."

Even my usually useless radar could detect a strong possibility of sex in the near future. It seemed I had lucked up on that rarest of God's creatures: an attractive, over-sexed date for whom dinner and drinks are merely a precursor to the real stuff. Most men live their entire lives wondering if such a woman exists outside the pages of Penthouse, and here I was with a real live specimen.

I should have been ecstatic, but I wasn't. I know my limits. I was swimming in deep, deep waters. As she rattled on about her sexual history (they were all 'ginormous' and incredible in bed) my natural disposition took hold, and I began to worry.

Even my usually useless radar could detect a strong possibility of sex in the near future.

I worried that my own equipment, which had never let me down and in fact had put in exceptional performances every now and then, would not be up to her usual standards. I worried that my one signature move was too conventional even to qualify as a move.

I worried that I'd disappoint, and she'd tell her friends, who would tell my friends, who would, because they are true friends, ridicule me forever and ever. At this point, I did what all civilized people do when they are faced with such a situation: I smiled my broadest smile, ordered another round and told our waitress to keep them coming.


There are a lot of awful stereotypes associated with black people, many that we would happily fight you over if you dared utter. The one involving larger-than-average penises is not one of them. I have yet to meet the man who will put up his fists and demand satisfaction if you inflate his vital statistics. We are happy to live with that slight; although personally, I do not encourage it, not because I am particularly unfairly endowed, but because I'd rather expectations be exceeded rather than merely satisfied when it comes time to unleash the proverbial dragon.

As it was, I decided that if the opportunity presented itself, I would in fact sleep with her because a) I consider it a matter of principle to never turn down sex and b) the alcohol was working its sweet magic and I was becoming defiant. Why couldn't I play with the big boys?

Why not, I say? Why the hell not?

We eventually made our way back to her place. I expected a den of hedonism, whips, chains and all, but there was none of that. It was in fact, quite normal. She had a normal couch and a normal rug; a normal television framed by a normal chest; and a normal kitchen with a normal fridge that thankfully contained a normal bottle of vodka. I kicked my frat-boy seduction technique into high gear.

"We should do a couple of shots," I said.

"Why?" she asked, "Are you nervous?"

"No," I said, a little too readily, "just, you know. . . something to do."

She laughed and led me to the bedroom. "We can skip all that, I have something better to do," she said.

Her room was contained chaos. There were clothes strewn across the floor, her bed was unmade in a well-used sort of way, there was an overflowing walk-in closet and a makeup table filled with stuff. The walls were bare except for one, which had an oversized mirror placed just so as to reflect a full view of the bed. She stuck her tongue down my throat before I could make any comment. There was no mistaking that she was in charge. She knew it and I knew it; my only job was to keep up. I went into autopilot: I caressed the places you are supposed to caress, rubbed the spots that you should always rub and undid her bra without too much fuss. This was Foreplay 101, and I am good at it. So good in fact, I managed to surreptitiously switch off the light without breaking rhythm. Darkness would be my ally.

Before long we were both naked and it was time to get down to business. I had made it through a bout of enthusiastic tugging without her recoiling in revulsion, and I took that as a positive sign. Perhaps my worry was unfounded. Maybe I did stack up. But the proof, as they say, is in the tasting of the pudding. She reached across me and fished a bright gold sachet out of her night stand.

Great. Magnum XXL condoms.

"Hurry," she said.

It is hard enough to maintain any level of romance while fumbling around with a darned condom, harder still when your partner has put you under the gun and you are expected to produce big things. I could have bolted at that moment. I could have grabbed my trousers, and run out of the door, my pride a little dented, my reputation in tatters, but my all important sense of self-delusion intact. To paraphrase Lincoln: better to keep your zipper up and be thought poorly endowed, than to display your wares and remove all doubt. But I did not.

Instead I gave myself a little pep talk, tore the plastic off the condom and rolled it onto my penis. It must have taken me a while because I was barely done when she told me to get on with it already.

She was looking over her shoulder, her ass stuck in the air; nature's position one. There was nothing for it. I crawled above her onto the bed and gave her my best thrust; a top-of-the-line, grade-A, go-on-my-son(!) thrust. And in response I got. . . nothing. Silence.

I panicked. My worst fears were coming true.

She was looking over her shoulder, her ass stuck in the air…

Any moment now she would turn around and ask what the hell I was doing, or worse, say something that would haunt me for life and prevent me from ever having sex again, something like "is it in yet?" or "is that all?" I pushed as deep as I could and sent an impious prayer to the heavens: "Please God, give me an inch. Just for tonight, you can have it back in the morning." I willed all available resources to the regions where they were needed most, and began pumping for all I was worth.

Just when I was losing all confidence, she barked. It was unmistakable. She let out a little yelp, like one of those designer handbag dogs, what Eddie Izzard would call a little-yapper-type dog. It was a small sound at first — I could hardly hear it over the boing-boing of her mattress springs — but it got louder and louder.

Before long her bark was the loudest thing in the room, and far from making me nervous (was it a bark of pleasure or disappointment?) it relaxed me. No, it did more than relax me: it made me laugh. The whole situation suddenly seemed ludicrous to the extreme, here I was (let's face it) drowning in an XXL-size condom trying to impress a barking nympho. I began to giggle, then chuckle. Then I was bent over in fits of belly laughter.

Suffice to say, I could not continue with the task at hand. She of course did not call me. I did nothing to warrant a repeat performance, and beyond representing a (regrettable) rung on her sexual ladder — if she even keeps track of these things — I am pretty sure she rarely has occasion to think of me.

I, on the other hand, am reminded of our short bout between the sheets whenever I am buying my box of regular sized Trojans and whenever I hear the bark of a little-yapper-type dog. As it turns out, my neighborhood is full of them.