I was 18 when it happened. After high school I had scored a great summer job at my dad's big office on an internship program they had for employees' children. At least it was supposed to be great. Actually I found life under florescent lights as boring as would any 18-year-old.
I had been a shy kid all through school and, in consequence, I was still a virgin. I thought I should be out trying to "get girls" (even though I still didn't really know how) rather than being cooped up in this stupid office.
Another minor detail about my virginity: I had a secret. It was a secret I had never revealed to anyone for fear of shame, humiliation, disgust. This was back before the internet--if I'd had the web back then I quickly would have found that I was not alone. But as it was, I to this day think I have some inkling what it might be like to grow up gay and in the closet, so great was my sexual desire, trumped only by my need to keep my preference secret. My deep dark secret? I liked fat chicks.
There was a woman in my dad's office that summer in whom I took a strong prurient interest. Her name (not her real name) was Linda Concepcion. Hispanic, maybe 35 years old--not more than 40--with long black hair that was something between curly and wavy, she was about 5'5" and could not have weighed a gram less than 200 pounds. And what pounds they were! I would guess, looking back, that she had a 44" bust and something above an F-cup. Her waist was probably 38 -- 40", a big, bountiful belly and generous love handles. And she was 50'' at the hips if she was an inch, with a ponderous teardrop shaped bottom. In short, she was a triple threat: A generally pear shaped woman with acres of ass and a bulging belly, but still managing to stack a well proportioned bust on that oh-so-lovely pedestal.
When she would sit down at my desk next to me to give me instructions in the spreadsheet software it would make me absolutely insane. Her trace of Spanish accent was musical and her perfume intoxicating, and periodically, when she really had to explain a particular entry, she had a habit of physically tapping that line-item on the screen, though this meant reaching past me to the monitor. Her shoulder would graze mine and she would be close enough that I could often feel errant strands of her hair graze against my face.
"You're listening, right?" she would sometimes ask, and even that couldn't snap me out of it because all I could think of was her enchanting accent. She had the faintest hint of that dialect of Spanish--what is it? Dominican? Puerto Rican?--that seems to turn 'y' into 'j': "Jou sure jou're getting all this?" I grew up in the southwest and was no stranger to Mexican accents, but this was different; this felt foreign, faraway, exotic.
When she would leave my desk I would be faced with an awful paradox. The boner she would leave me with was mystical, full, rock hard, tingling and itching to come. It was a boner I could never seem to reproduce at home at night in my bed, eyes closed trying to recreate the moment so I could jerk off. At home I almost always got a different boner: respectable, but lacking in the painful urgency that I so desperately wanted to relieve when Linda would depart from my presence at the office. The paradox? Before I could get up and go to the restroom I would have to let enough of the moment pass that I could at least get down to half-mast. I even thought about trying to stroke one off in my pants at my desk once but got cold feet. I wasn't sure how big of a mess it would make but it didn't seem worth the risk that it might seep visibly through my pants.
Then something strange started to happen. Linda started making extremely bold sexual advances at me. Or so it seemed. I recall clearly the first time it happened. It was a spreadsheet day, therefore also a boner day, and when she had finished showing me what was wrong with my entries she didn't stand up but instead remained seated beside me making small talk, asking about school, future plans, etc. But then we got to the subject of girls.
"You mean you've never had a girlfriend?" (Jou mean jou've never had a girlfrien?)
"Not really."
"Not really, what is that 'not really'? You've been on dates." (Jou've been on daiss.)
I shook my head.
"So you've never ...?"
She let the question hang there while my mind applied Occam's Razor. It didn't seem possible that this 35-ish female full-time employee was really inquiring about a male summer intern's virginity. But then there just didn't seem to be anything else the question could mean. What little ambiguity lay in her silent trailing off did not leave me with much wiggle room. If she was talking about what I thought she was talking about and I lied, claimed to be fully fledged as it were, she might need a story, a background, a who-what-where-when-why. (Well, okay, not 'why'.) I wasn't prepared to make up a story on the spot so I shook my head no and felt my face redden.
What she said next floored me, and still does to this day when I think about it. I was half-expecting some advice on how to be confident with girls but, instead, all she said was: "Too bad. One of these days me and you should go make whoopee in the ladies room." I'm sure my eyes widened in shock as I gaped across at her, stunned speechless. There was a twinkle in her eyes and a wry, knowing smile as she enjoyed my surprised confusion. She let the overture hang in the air exactly two beats before, back to business, "Here let me show you one last thing," pointing again at the screen. In her tone it was as though she'd said "just kidding."
But, as I was thinking about it later, I realized she never actually said "just kidding." That's what was bothering me. Was she serious? Or was it so obviously a joke that she didn't even feel the need to say "just kidding" because it was implied. Over time I (sadly) became more and more convinced it was the latter. Even the word she used, "whoopee," helped confirm it was a joke. If you're reading this 100 years from now, keep in mind that no one in the early 1990s called it "whoopee." Not seriously anyway. It was a way of sanitizing it; she made a dirty joke without using a dirty word. That was all.
But then it happened again. Maybe a week or two had passed and she checked on my status. "Still nothing?"
"Still nothing," I confirmed exasperatedly.