If I like him, he’s probably gay.
he question “How did I end up losing my virginity to my gay best friend, dressed as Sandy from Grease, while my maid taped us from inside my closet?” is one that most girls never ask themselves. It all began a long time ago, when I was a little baby Babe, running around the garden in Pampers. Just kidding, my nannies would’ve been fired immediately for even saying the word “Pampers.” My skin is sensitive. I required cloth diapers.
When I was six, my father sent me to a very chic elementary school. At the time, La Maison du Petit Étoiles was the most forward-thinking school in the States. I think they invented the dry-erase board or something. To this day, I believe my education at Maison set the tone for my entire relationship with the world. In other words, it bestowed upon me a high level of taste and a low tolerance for processed kid’s food. We only ate certified organic greens and root vegetables direct from le jardin.
It was at La Maison that I first met Roman Di Fiore. From day one, Roman was a total mo, as well as my partner in crime. I thought he was the coolest kid in our class. He said what he wanted, dressed how he wanted, and did whatever he wanted, and I loved him for it. When we were ten, in honor of Princess Diana’s death, Roman wore a purple three-piece suit for a week and I wore a series of custom purple Versace children’s dresses. Although I didn’t know it at the time, the boy I played house with, the boy who would only let me pretend I was his wife if I let him wear my sequined scrunchie around his ankle, the boy who on the jungle gym politely asked if he could “touch my wee wee,” would eventually take my virginity.
But that was much, much later. Tragically, Roman and I were ripped apart when his family moved to Las Vegas. Roman’s dad, Mauricio, was a movie producer who decided to leave the film business and compulsively invest in commercial real estate/ his gambling addiction. He now owns half of Vegas.
I was devastated when Roman moved away. Who would braid my hair? Who would tell me I looked like Christy Turlington? Who would go to ballet class with me? It wasn’t easy, but I moved on, and resigned myself to hanging out with the girls in my class who were obsessed with me.
Growing up lonely and beautiful in LA without a gay best friend to lean on, I quickly learned that even the homely girls in my seventh grade Social Studies class, whom I thought I could trust, were psychos. Especially at Archer, which is a private, all-girls school in Brentwood, where every girl’s main objective was to out-slut the next. Parading my A cups around in a tube top and hooking up with Mark McGrath at MTV’s Spring Break was not my style, so I stuck to shopping.
By the time I was a B cup (sophomore in high school), I had finally started to entertain the idea of having sex. I knew it was time I took my vagina out for a test drive. She was ready for her maiden voyage. Yeah, I had given a couple blowjobs and done the whole “let’s get drunk and make out and maybe get naked in your parents’ room” thing, but I wasn’t the type of girl who was about to give my virginity away to a guy I barely even knew just because he drove a Range Rover. Even though most of my friends had done it and gossiped about it, sex still seemed sloppy and gross to me. Which is why it came as a total shock when I laid eyes on the new boy at school and instantly wanted to fuck him.
It was the first day of school, and I was about fifteen minutes late to first period Geometry. I mean, who gives a shit about shapes if they’re not part of a Pucci print? Am I right? I settled down in my desk, turned to the left, and there he was: a tall, sinewy, Burberry Prorsum ad. Studded leather jacket, ripped white tee, perfectly skinny black jeans, and filthy black Dior Homme ankle boots. A true fashion punk. His look said “Fuck me, or fuck off. Your decision.” His skin was flawless, his hair was calculatedly disheveled, and I wanted to kiss him. On the dick. I swear he winked at me and I literally melted.
Babe, I thought to myself, Do not fall in love. Do not listen to your stupid body. Your body is a nutcase, you’re puffy from those three beers you drank over the summer, and your skin is an 8 right now, at best. It’s first period of the first day of sophomore year and already you’re eye-fucking this strange boy-man. Sit the fuck down. But you are sitting down! Shut up.
I mentally slapped myself and kept my eyes locked on my teacher’s depressing red clogs, never once looking at the street prince sitting next to me. I was trying so hard to not completely lose my shit and break down in a tsunami of teenage sexual angst, and doing a pretty decent job, until he turned and put his hand on my shoulder.
“Did you have a good summer? I heard Turks and Caicos had one of its most beautiful seasons this year, which would explain your perfect tan.”
I’m sorry, what? Did anyone else just hear that? How did he know my dad and I go to Turks and Caicos every August? My heart was pumping so hard. I swear I could feel my knees sweating. A single tear fell from my eye. Was he confused? Then I said something stupid.
“Do you love me?”
I started full-blown crying. I never thought I’d be the kind of girl who would meet her husband in high school, but apparently I never think a lot of things.
At this point, our geometry teacher kicked us both out because I was literally sobbing and clinging to my desk. I was able to pull myself together by the time we were in the hall.
“Do you have any cigarettes?” I asked my soul mate. “Totally. They’re French, is that okay?”
“Of course. Get out of my brain, pre-cog.” (I have a major sci-fi obsession. You’ll learn this about me.) “Do you think I’d smoke them if they weren’t?” We walked out behind the Math building. Roman handed me a cigarette and lit it.
“How’d you score that bag? It doesn’t show in Paris until next month,” he asked, smiling.
“My dad is an attorney and his firm represents Louis Vuitton, so I’ve known about the collaboration with Steven Sprouse for months. It’s a finished sample. Whatever. You’re ogling.”
He stopped and turned to me, grabbing both my hands. Butterflies.
“You still don’t know who I am, do you?”
As soon as I took a close look into his big dark eyes, I remembered.
“Fuck off! ROMAN?!” We hugged and I died a little on the inside. It was a horrible combination of excitement to see him again mixed with the devastation of remembering that he was totally into dudes. There was no chance in hell that my body, which included breasts and a vagina, would ever be of any interest to this queer beacon of chic.
From that point on, our friendship picked up exactly where it left off. We would do all kinds of fun things, like weekends in Palm Springs, waxing, dieting, making fun of frisbee players, etc. I mean, he totally understood my need to change clothes three times a day and completely supported my blowout habit, and I completely supported his blow habit.
One night, we were making a list of guys at our school who I could potentially have sex with, categorized by hand size. I wanted to be into it, but I kept coming back to the sad truth that Roman was the only one I wanted. I couldn’t let go of my initial attraction to him from that first day in Geometry.
I didn’t say this out loud, obviously, but in a stroke of genius, I realized his gayness was exactly the reason why he should be the guy I lose my virginity to. Roman was an amazing dancer, his skin was softer than mine, he was sweet and attentive, and he was completely gay, so I could eliminate the fear of him bragging to his “homies” and spreading any miserable rumors around school about the true circumference of my thighs or my less-then-perfect vagina scenario (more on that later).
I decided to confront him. “Roman,” I said plainly one day while we were floating on pink rafts in my pool, drinking oxygen water, “on a scale of Pam Anderson to your grandpa, what’s your blowjob style?”
“What do you mean?”
“I mean when you’re giving a guy head, are you, like, aggressive or gentle?”
“I guess I don’t really have a style. I kind of just go with the flow. It’s more about what the guy wants, ya know? I just like making people feel good.”
Roman seemed to know way more about sex than I did, which was superhot.
“Yeah, yeah, totally. Oh my God, I’m the exact same way. Totally. Just, like, pleasing guys is my main thing. So, you’ve never wondered what having sex with a girl is like?” I asked, praying that this would inspire him to jump off of his raft and de-virginize me on the spot.
“Yeah, I’ve thought about it. And it weirds me out. I mean, no offense, Babe, but I just don’t have any interest in vaginas. They seem really soft. Too soft for me. The whole vagina thing is just unclear.”
I had a feeling he was playing games with me, so I said, “But if the moment is right, could you be into it?”
“Yeah,” he said. “Maybe. I guess.”
What I heard was “If I’m drunk enough, I will fuck you. P.S. you look superthin in that bikini.”
I decided then and there that I was going to get Roman drunk. And fuck him. I set up an epic Grease-themed date night for the two of us. He lived for that movie, and I totally understood the fetish. At the time, John Travolta was his personal icon. We met at Mel’s Diner on Sunset. I’d had my hair dyed the most beautiful shade of honeycomb blond (I was born a brunette) and teased and curled to perfection, and I wore a push-up bra, black tank top, vintage Versace leather jeans, and red pumps, obviously.
I should mention that as a very young girl I became obsessed with fashion. At age seven I started drawing sketches of myself in all of the outfits I would wear. Drawing just came naturally to me and I really enjoyed doing it. I realized that the best way to put a look together was to draw it out on paper and see if it the ensemble worked. When you look in a mirror, it’s easy to get distracted by other objects in the room or problem areas on your body, but when you sketch, you really punctuate the important aspects of your look: you and you and your clothing. Sketching can help you discover something completely new about a piece of clothing that you thought you knew inside-out. Highly recommend.
Anyways, back to the Grease date. Roman was a vision in black Fendi leather everything. He looked so fucking sexy that night. He looked like the kind of gay who would have no issue breaking your nose if you called him queer, especially since his hair was slicked back and he was on a fucking motorcycle.
I ordered a side of fries but substituted celery sticks for the fries. They were delish. Roman ordered a burger and a malt, as a joke (he would never eat that in public). We spiked our diet Cokes with Jack Daniel’s under the table and made fun of our lazy-eyed waiter. The date was shaping up perfectly, our conver-sation was supercute, and Roman was starting to get buzzed and flirty. God, we were so happy then.
Roman wanted us to go back to his house after dinner, but I was not about to lose my virginity at his family’s Holmby Hills mansion which, not coincidentally, was built to resemble an ancient Roman palace, but smaller and less ancient. Not chic. Besides, I had planned on bringing him back to my guesthouse, where Mabinty (my maid/bff/personal documentarian) was hiding in the closet with a camcorder. Like all momentous occasions, I figured this night should be videotaped. How could I have every birthday taped, edited, and organized on a shelf in our library and not have any record of one of the most important events of my life? Plus I’d stocked the bar in the guesthouse with a ton of liquor to ensure that Roman would definitely be wasted.
By the time we sashayed through the door, all the pieces of my quest to lose my virginity were falling into place. I could see the finish line in the distance. I could hear the cheers of my loved ones on the sidelines; they were handing me cups of water that I was pouring on my head. They were throwing me PowerBars, and I was slapping them, because everyone knows PowerBars are nothing but carbs and sugar, with barely less regret than a Snickers bar. P.S. I would never run a fucking marathon.
Roman insisted on having a few margaritas. Perfect. I could tell he was nearing a blackout when I turned on the Grease soundtrack and he legit screamed with excitement, lifted me up, and threw me on the bed. We danced on the bed for a little bit, and when the moment seemed right, I went in for a kiss and simultaneously grabbed his dick. I wasn’t expecting him to kiss me back, but when he did, I went with it.
“Romie. Let’s make love.”
“Babe that’s gross. Stop. Wait—is there somebody in your closet?”
“Huh? No! What? Of course not. You’re shitfaced!”
I lifted Roman’s shirt over his head, lay down on the bed, and peeled off my leather pants. A note: vintage Versace leather jeans are really sticky once you’ve let yourself sweat in them, so if you think you’re going to be in a heated situation, you should preempt by dusting your legs with baby powder before you put them on. It will save you twenty minutes when you go to take them off. Trust me.
By the time I had my pants off, Roman was lying next to me wearing nothing except his Calvin Kleins.
“You look really thin. Are you okay, Babe? Sometimes I worry about you. I mean, you ate celery sticks for dinner.”
Obviously my adherence to the Atkins Diet had been paying off. I smiled.
“Roman, I’m fine. I want to have sex. With you. Right now.” “Babe, I—”
“I don’t care what you say. You are going to have sex with me.
Look. I’m naked. And you’re not turning away or anything. You’re staring at my boobs.”
This was true. I’d wiggled out of my underwear while Roman was going on about my weight. Nothing makes me want to get naked more than someone telling me how thin I look. I was starting to feel really free with my body. Isn’t sex amazing?
“Take your pants off. We’re fucking,” I demanded.
“Babe, I’m not into you like that. What are you doing?” “This is going to be fun! Trust me. You’ll like it.”
“No I won’t. Vagina scares me. I don’t even know what to do with it.”
“Well, let’s make a safe word that we can say if things get too intense. If either of us says it, we’ll stop. But honestly, Roman, just man up and don’t say the safe word.”
He agreed. And we decided that the safe word would be “Tom Ford.” Roman took his pants off and lay next to me. His dick was huge. Honestly, I felt kind of scared, but we’d gotten this far, and there was no way I was going to back out now.
“Okay, get on top of me,” I said.
“I hate you, Babe.”
“No, you don’t.”
“Now, when we start doing it, I want you to really go for it. It’s probably going to hurt me a little bit, and I might scream, but you need to just keep going.”
“Okay. But Babe—”
“I’m not sure—”
“Just fuck me, Roman!!”
He thrust his hips forward, and all of a sudden it felt like a fire had been lit inside my vagina.
“TOM FORD!” I screamed, slapping him across the face. “Oh my God! I’m so sorry!” He looked terrified. “It’s okay. Sorry for slapping you. Just kidding with the safe word, keep going.”
He started thrusting again. At first it felt sharp, then the pain eventually went away, then it felt rhythmic and good-ish. By this point I think I was in such shock that I was actually having sex, that I kind of allowed myself to bliss out and go with it. It became apparent that Roman had gotten really into it too, when all of a sudden he flipped me on my stomach and started fucking me from behind, moaning, “Danny! Danny!” I was moaning too, and kind of laughing. And kind of screaming “Sandy!!!” I figured that I had gotten mine and it was only fair that he got his, for what it was worth.
All in all, having sex for the first time with a gay guy was, like, totally weird and totally hot. It didn’t feel anything like I had expected, but I guess sex is one of those things that you need to try firsthand to understand. Like a facial. After it was over, we both hung out naked and watched Clueless until we fell asleep. The next morning, I woke up to a note from Roman on my bed-side table. It said:
I will never do that with you again, but just so you know, I fucking loved it. Pedicures at 3?
We don’t talk about that night very often, but sometimes, when we’re drinking whiskey at my place, Roman and I watch the tape. Despite the Led Zeppelin tattoo situation that was going on on my ankle at that point (removed last year), and Mabinty laughing so hard that the camera is shaking uncontrollably, you can clearly tell that we both looked amazing, young, free, and in some sort of love. Even if it wasn’t traditional. Or natural.