My romantic history with women is surprisingly vast. In my younger days, I was what my dad called a major “pussy magnet.” But, when you think about it, my gift to attract the ladies is one of nature’s cruelest jokes. Why give someone like me that power? That’s like giving a butterfly a hammer. Sure, hammers are cool, but what in the hell is a butterfly supposed to do with it?
Still, I tried. Why? Because even though, deep down, I always knew I liked boys, dating girls was just what I thought was expected of me. I felt the same way about having to take algebra, even though I was certain I’d never use the Pythagorean Theorem when I grew up. But, sometimes the most important part of learning who you are is discovering who you aren’t.
My first girlfriend was in fifth grade. Her name was Becky and she was one of the popular girls, which I assumed would immediately increase my social status by leaps and bounds on the playground. Plus, I liked her mom a lot because she had the same hairstyle as the mom on Picket Fences. I’ve always trusted a woman with a sensible bob.
Becky and I started going out the same day my friend Tara began dating this boy named Caleb. Just two preteen couples, trying to make a go of it in this crazy world…
In elementary school, “going out” meant that you spent recess together, stood next to each other in line for lunch, and shared a seat on the bus, so it was just about the right level of commitment for a ten-year-old me.
Becky asked me to be her boyfriend as we boarded the bus for a field trip to Wild Waves Water Park, an annual event at my elementary school and the one day every year that I dreaded the most. As an adult, I’m still not comfortable enough with my body to take my shirt off in front of strangers, but when you’re ten years old and have man boobs that could fill a bikini top better than most of your prepubescent female classmates, water parks are your absolute worst nightmare. I usually spent the entire field trip making excuses to not remove my shirt. “Naw, I’m cool. You guys go ahead,” I’d tell my friends while walking toward a pay phone. “I’ve gotta make a quick call.”
Then I’d listen to the dial tone for twenty minutes or so while nervously planning my next move. I know what you must be thinking: if I didn’t want to take my shirt off, why didn’t I just go on the water slides with a T-shirt on? Because the only thing more lame than being the guy with man boobs is being that guy who wears a T-shirt in a swimming pool. It’s like trying to cover a blemish with a neon green Band-Aid. I might as well have used an entire decade’s allowance to hire a skywriter to scribble Ross Mathews has man boobs! high above the water park for all my normal-chested classmates to see.
But Becky, for some reason, didn’t seem to mind my physical deformities, probably because she had one of her own: her hair was an absolute mess. It had always bugged me, even before we were boyfriend and girlfriend. For some reason I’ll never understand, her mother—the same mother whose own hairstyle gave me such joy—gave Becky a perm and put in waaaay too much gel, so she always looked like she had a ball of uncooked Top Ramen noodles on her head.
Despite our flagrant flaws, I agreed to commit to Becky as my one and only true love. I was thrilled. I was in a full-fledged, real relationship! Just like the people on TV—very Uncle Jesse and Aunt Becky on Full House.
Of course, I understood that being in a mature relationship wouldn’t be easy. Going forward, compromise would be essential. I knew that if she wanted the red crayon, she could have it… just as soon as I was done with it. And if there was only one empty swing left on the playground, she could push me until the end of recess. That’s how compromise works.
Unfortunately, Becky and I never made it to that stage of our relationship. On the very same day our romance began, it came to a sudden and screeching halt. During the bus ride home, her swimsuit still damp from Wild Waves fun, things got…complicated. After huddling with her friends in the seat next to ours, my main squeeze Becky turned to me and declared, “I’m breaking up with you. You’re going out with Tara now.”
Her declaration hit me like a ton of Legos. “What?” I stammered. “I am? But I thought Tara just started going out with Caleb.”
“They were going out, but I just traded you for him. Go sit next to your new girlfriend.”
What a nasty bitch, right? She traded me?!? What am I, a lousy homemade bologna sandwich you try to swap for a store-bought Jell-O chocolate puddin’ snack?
In hindsight, I wish I would’ve told her to take her crunchy hair and get bent, but I didn’t. I just went along with it, which was totally unfair because my new girlfriend Tara wore tan corduroys and smelled like Thousand Island dressing. Luckily for me, though, my new relationship with Tara was even shorter than my previous one with Becky. Not two minutes after I sat down next to her, both of us glaring at our exes-turned-happy-couple, Tara added insult to injury when she huffed, “This isn’t working. I think we should see other people.”
Women—am I right?
I was left emotionally scarred and for years refused to get close to any woman other than Little Debbie or Debbie Gibson. It wasn’t until I entered the seventh grade and turned thirteen that I met the girl of my dreams, a fabulous young lady so full of verve and panache that one couldn’t help but compare her to a young Liza Minnelli. She simply had to be mine!
Maria was a spicy senorita whose last name, ironically enough, was the same as my favorite brand of salsa. She had silky-smooth dark hair, big brown eyes, and ruby red lips. She was dainty and delicate, resembling one of Marie Osmond’s signature collectible porcelain dolls from QVC. That is, until your eyes strayed from her angelic face and down to her prematurely large breasts. Seriously, this fourteen-year-old girl had the jugs of a middle-aged cocktail waitress.
Despite her Double D-lightful endowments, we started dating immediately. This consisted mainly of talking on the telephone for hours each and every night, about anything and everything—from drama in our middle school to drama in the Middle East. On the weekends, we would go to the movies together, holding hands in the dark and reaching various make-out milestones while watching classics like Aladdin (our first kiss), The Bodyguard (our first under-the-sweater action) and the Elizabeth Perkins existential gem, Indian Summer (during which we engaged in something I would later learn from my older brother was affectionately referred to as “finger banging”).
No, your eyes are not deceiving you. I did indeed take a “hands-on” approach with precious Maria. You may be surprised to learn that I was particularly adept at manual stimulation. I was so talented, in fact, that Maria and I were kicked out of Indian Summer because of her audible pleasure. Yeah, I’m that good! I wish I knew how to share my technique with you all, but I just can’t put my finger on it.
It’s a well-known fact that girls mature faster than boys. And when you consider that Maria was a full year older than me, you essentially have the equivalent of Samantha from Sex and the City dating Doogie Howser. Yep, Maria was a fourteen-year-old cougar and, like her feline namesake, she was hungry for raw meat. My raw meat. And by “raw meat,” I mean my wiener.
She was downright insatiable, and I was on 24/7 crotch watch, constantly swatting her hand away from my private area and finding increasingly creative excuses not to go any further. “Oh Maria, I so very much wish I could do that with you,” I’d try to cover, as my panicked voice built in both speed and pitch. “But I simply must leave right this very moment, because it’s Thursday and Thursday is the day I read the latest issue of Reader’s Digest to the lonely old senior citizens at the retirement center and I have to grab some hot tea with honey because they love it when I do the voices, but I’ve had this tickle in my throat all day and I really don’t want to let them down because they’re so very old and frail and I’m all they have in this horrible world and they could die at any moment. So, as flattered as I am, Maria, by your incessant clawing at that area, I’ve really got to get the fuck outta here!!! ”
Apart from lying to her sexually frustrated face to avoid any physical contact beyond my fancy fingerwork, I was an absolute perfect boyfriend. I was so attentive to my number one gal, in fact, that every single night I called KBRC, Mount Vernon’s local AM radio station, and requested our song.
I’d turn up the volume and hug my radio when I finally heard the DJ croon, “There’s nothing sweeter than puppy love, is there? This one goes out from Rossy-Wossy to his little burrito of love, Maria. Here’s Whitney Houston with ‘I Will Always Love You’…”
Maria was cruelly ripped from my life when her family decided to leave our small town for the bright lights of Las Vegas. Suddenly our song went from “I Will Always Love You” to Roxette’s “It Must Have Been Love.” God, teen love can be painful.
But, alas, life goes on, and soon I was ready to love again. I briefly dated a girl named Danni who had perfect eyebrows and lived in the trailer park behind my middle school. Her parents had a Kama Sutra book we secretly flipped through before making out. We found the exotically erotic images arousing, confusing, and intriguing at the same time, much like how I feel now while watching the Food Network. I ran into Danni recently at Wilsons Leather the last time I visited my hometown. She was the proud mother of three great kids and two still-amazing eyebrows.
My most serious relationship with a woman was in high school. We got to know each other in those steamy hotbeds of sordid teen romance known as Drama Class, Jazz Choir, and Debate Club. Carrie was gorgeous: Long strawberry-blonde hair, milky-white skin, adorable freckles, and an ample bosom.
She was assigned the job as my official dresser throughout my award-worthy portrayal of Henry Higgins in the Mount Vernon High School production of My Fair Lady, helping me in and out of my costumes (which is almost as sensual as it sounds). Once Carrie saw me in my polka-dot boxer shorts and top hat during intermission, she was hooked. So was I. After all, much like Barbra Streisand, she was a triple threat: smart, funny, and talented. In a show-biz minute we became the very best of friends, spending nearly every waking moment together. Eventually, we shared the ultimate bonding experience between a man and a woman: a makeover!
Although I adored Carrie’s long flowing hair, it was undeniably dry and suffering from unfortunate split ends. It simply wasn’t an accurate reflection of her bouncy, lustrous personality. Frankly, she deserved better hair, and I was just the man who could help! So, not unlike the My Fair Lady character I so magically portrayed onstage, I convinced my very own real-life Eliza Doolittle to cut that unsightly haystack into a sleek, sophisticated bob.
I offered reassuring looks and approving nods as she sat in the pleather chair of the beauty salon conveniently located in the strip mall between Thrifty Foods and Little Caesar’s Pizza. As I describe this, please imagine the song “Pretty Woman” playing over alternating shots of scissors snipping and long strands of bone-dry, beige hair floating down to the linoleum floor. When the skilled-but-affordable stylist finally swiveled Carrie around to face me and whipped the protective black nylon smock from her alabaster neck, I was in love. Her new ’do looked so healthy and strong! There, staring up at me was the stunningly perfect combination of Posh and Ginger Spice!! I squealed with delight, clapping my hands and enthusiastically jumping up and down while screaming, “So pretty!!!”
Talk about turned on. Her new look knocked me for such a loop that we made out that night. A lot.
In hindsight, and now with some life experience under my belt, making out with a girl is much like making out with a guy—except softer and much less enjoyable. It’s not that I wasn’t into it, per se, but I approached it more like a lab experiment than a hormone-fueled sexcapade. It was as if I were studying rocks instead of getting my rocks off. Lighting a Bunsen burner as opposed to burning with desire. I was merely trying to pass the class, not trying to tap that ass.
(Honesty moment: The previous paragraph contains absolutely everything I know about both women and science.)
My special friendship with Carrie quickly progressed, and before I knew it, we were officially boyfriend and girlfriend. I found committed relationships in high school to be very different than when I had gone out with girls in grade school. Back then, simply sitting on the bus and holding hands was enough to satisfy my partner. But in the eleventh grade, the stakes were much higher. I knew what was coming and I was terrified.
It happened at her house. Allow me to set the scene: it was just the two of us, lying on her bed, watching the ultimate aphrodisiac of animated movies, the film that no doubt has led many innocent teens to carelessly fling themselves into the fiery pit of passion: The Lion King.
I was somewhat taken aback when, during the most dramatic scene in the movie, the one in which Simba’s father is (spoiler alert!) brutally killed, Carrie got up and left the room. I thought about hitting Pause on the VCR when I heard the shower go on in the adjacent bathroom. I wasn’t overly concerned. After all, Carrie and I had watched this movie like seven times together before, so it’s not like she was missing anything. Besides, that scene always made me feel dirty, too. She probably couldn’t bear to watch that heart-wrenching moment yet again. I hope she takes her time in there, I thought to myself, you know—loofah, exfoliate, deep-condition…
I was very in tune with Carrie. Yes, we were like one that way, always on the same page. After all, this was the girl who sang Rent in the car with me, never struggling to achieve flawless, Broadway-caliber harmonies. She could always finish my sentences and I would always finish her nachos. Utter synchronicity.
Five minutes and one Elton John ballad sung by African wildlife later, Carrie emerged from the bathroom in a cloud of Pantene-scented steam. She was wearing nothing but a towel and a sultry, vixen-like stare.
(INSERT RECORD-SCRATCH SOUND EFFECT HERE.)
I was certainly no expert in lovemaking, but I’d seen enough soap operas to know what it meant when a girl entered a room wearing simply a towel surrounded by steam. Oh God. It was happening. I tried to stall. “Do you, uh, want to finish the movie?”
She slowly shook her damp head. “No,” she purred, staring at me like a starving jungle cat leering at a succulent pork chop.
Oh. Dear. God. It was happening. It was really happening. Every last instinct told me to just push Play on the remote control and continue watching the movie in one last-ditch effort to extinguish her burning desires. But before I could make my move, she made hers: she dropped the towel.
Oh dear God in heaven! Here I was, The Lion King on Pause and a naked woman—a natural blonde, by the way—standing before me. The law of the jungle is eat or be eaten, so I made a snap judgment and thought to myself, Hakuna Matata!
I committed fully. Gosh darn it, if I was going to do this I was going to do it right! So after making out for a bit, I bravely shimmied “down South” until I was face-to-face…with a vagina. It was a normal-looking vagina, I guess. Like a sideways smile—or a frown—depending on how you looked at it. There was no turning back now.
Three…two…one…I closed my eyes and went at it like a fat kid in a pie-eating contest at the county fair.
It was fascinating. It was kind of like trying to eat a plastic toy ice cream cone—you can lick and lick forever, but it just won’t go away.
Eventually I stopped to take a breather and get another good look at it. It was…unreal. It was bizarre. I had so many questions. I kept trying to figure out how it worked. What part of this thing does the peeing? There was simply so much going on! I mean, this was no Barbie doll crotch—this was the real deal—and I found myself wishing it came with an instruction manual. It was much too confusing. I didn’t like it. I didn’t want to do it anymore.
Eventually, she noticed that I’d stopped and sweetly asked me, “Ross, are you okay?”
I’m not sure how to describe my response. It didn’t consist of words, just a guttural whimper of resigned defeat. “Ehhhhuhhhhhggggghhhhh.”
Needless to say, that kind of killed the mood. I felt horrible, like I had just somehow dissed her vagina. Don’t get me wrong, it was a pretty part of a pretty girl, but I was pretty sure that it wasn’t for me. And it was pretty clear that I wasn’t the boy for her. Yes, I could help give her a hot new hairstyle, but I could never help give her an orgasm. She deserved a guy who would dive right in with wild abandon and passionately ravage her lovely lady parts, not study them like a periodic table. Although we broke up shortly thereafter, Carrie and I still remained good friends.
I don’t regret what we did that night. I think I heard Oprah say once that we should all do something every day that scares us. I believe that, too, and I’m all the better for it. But what I gained in self-respect that day didn’t come without a price. You see, I haven’t been able to watch The Lion King ever since. For some reason, it just leaves a bad taste in my mouth.
God bless all these amazing ladies: Becky, Tara, Maria, Danni, and, most of all, darling Carrie. These wonderful women sacrificed very intimate parts of themselves—some more intimate than others—so that I could one day discover something very intimate about myself: I am a (spoiler alert!) raging homosexual.
Thanks, girlfriends!