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Or — “How to get dumped, find a new man, and also ruin a perfectly good pair of white shorts.”
Awkwardness and sex go hand in hand. It’s like popcorn and movies, you can’t really have one without the other. Your first time is certainly no exception, either. How many people’s first times included having your hair pulled (on accident), your head bumped, or clinked teeth with your equally awkward partner? None of us knew what we were doing, so awkward situations simply couldn’t be avoided.
Losing your virginity in reality is a far stretch from that Hollywood trope where the super romantic music cues, the candles are lit, and the two actors are lying on a bed of roses while trying to devour each other’s faces. Well, the devouring of each other’s faces part is actually pretty accurate seeing as how kissing was still a foreign concept to many of us then (and some adults currently), but it’s never really quite that romantic. Except for my first time, but I think I am the exception. Let me explain:
I’ll start at the beginning. When I was 16 I was pulled out of school the second semester of sophomore year due to a family crisis. I had just started feeling good about school and getting a nice group of creative friends. I even started getting close to my crush. It was a shock when I was forced to move to a new city and had to start over midway through the year. I mostly kept to myself that first couple weeks, sitting alone at lunch reading The Da Vinci Code or some other mystery book. That is, until I met my first boyfriend.
He was tall, tan, was in a band, and he basically looked like Johnny Depp-as-Edward Scissorhands meets Gael Garcia Bernal in “Y Tu Mama Tambien.” My little goth heart was totally smitten so much that I had nearly forgotten about my old life and my old friends in school. Nearly.
“He was tall, tan, was in a band, and he basically looked like Johnny Depp-as-Edward Scissorhands meets Gael Garcia Bernal in “Y Tu Mama Tambien.”
My boyfriend and I, his name isn’t important, would pass letters to each other in between classes and we would hold hands after school. So cute and innocent that to think about it now makes me cringe so much my face actually hurts, but back then in my 16 year old world, having never been in a queer romance before, meant everything to me. It was the first time I ever felt like I could fully be myself with someone, let alone another boy, and at such a vulnerable age it felt good to know that the feeling was reciprocated.
That is, until we broke up.
We only dated for two weeks (high school moves so fast, doesn’t it?) but that two weeks was just enough time for me to start thinking that he was “the one” and to start dreaming of moving to New York and buying our first brownstone together. (I’m fully aware of the grossly inflated home prices in New York now but hey, a kid can dream, right?!) I was incredibly heartbroken and distraught after the breakup and I vividly remember hiding in my room listening to “Everytime” by Britney Spears and “Don’t Speak” by No Doubt on a loop for weeks, just sobbing. Those first loves always hit the hardest, don’t they?
Not only that, but I was planning on losing my virginity to him, which added a whole new level of melodrama to the situation. Who actually breaks up with someone BEFORE they hook up? It felt weird and I was left feeling dumbfounded with my ego totally shot. I had no idea how I was supposed to face him at school ever again.
Good news is, I didn’t have to. We never really spoke after that. He practically avoided me the rest of our High School days, and I really never got closure. That is until we hooked up at a house party not long after we graduated. He had gotten so drunk that he threw up tequila while we walked to my house and proceeded to have really bad, awkward, drunk sex in my bedroom while two other friends hooked up on the floor next to us… but that’s a story for another time. Needless to say, we didn’t talk much after that.
“He had gotten so drunk that he threw up tequila while we walked to my house and proceeded to have really bad, awkward, drunk sex in my bedroom while two other friends hooked up on the floor next to us...”
After being dumped, I had resigned my dreams of brownstone shopping in New York City and instead decided on becoming a monk, because it was seemingly my destiny to be celibate and to die an old virgin. That is, until I was approached by a classmate who asked me if I wanted to meet one of her friends. I originally had said no as I was too busy looking up monasteries to move to when she showed me a picture of him. He was handsome, athletic build, captain of the drill team, had a driver’s license, a job, and had his own car. Heartbroken yet intrigued, more so about what exactly a drill team was, but meeting this mystery man seemed like a better idea than a life of celibacy and monkship on a secluded Tibetan mountaintop. The distraction was definitely welcomed.
The next day I was taken by my classmate to a place on campus I had truly never been inside before — the band room. When we walked in there were a few girls standing around and right in the middle of them was the really good-looking guy from my friend’s picture. He was dark complected with a great smile and a closely cropped haircut, lightly acne’d, and was wearing white cargo pants and a light blue tight shirt that showed off just a hint of his lean muscles. I was feeling more like a troll compared to him while wearing my Jack Skellington sweater when he came up and introduced himself.
“Hey, I’m Marshall,” he said.
“Uh, hey, I’m Demi,” I replied.
How romantic.
We chatted for a little while but I was of course super awkward and had no idea what to say in this situation, so I assume there were a lot of “uh-huh” and “mm-hmm’s” going around. He eventually gave me his number and we both went about our days. My heart was racing, I didn’t feel like it was even possible to be attracted to another person after what happened before. Life was moving so fast.
Over the next few weeks we started talking on the phone fairly regularly. Although we seemed like polar opposites we actually had a lot in common. We both had a love of movies like “Clueless” and “The Texas Chainsaw Massacre,” and he actually lived near my grandmother’s house.
One day we were talking on the phone, he told me he had a birthday coming up and was planning a sleepover/beach day the following weekend. He asked if I’d like to come. I understood the context of what this meant and I said hell yes. I was a living, breathing Snape GIF, and my body was ready!
The next weekend I showed up to his house in my new outfit — a polo shirt, white shorts, and flip-flops. (I was dating a preppy guy so I had stopped wearing black and started experimenting with colors.) His house was huge and gorgeous, with marble tile floors and a huge, curved staircase that led upstairs which took up the entire foyer. It was a far cry from the trailer my family lived in at the time. Just as I was feeling self-conscious about it, I was welcomed in by him and the few other friends that were there. It was him, myself, the classmate who introduced us, and two other girls from school. It was a decent group, and we all spent the whole night watching “Mean Girls,” while Marshall and I just cuddled and hung out on the couch.
While the girls were falling asleep, Marshall and I started getting closer. He started kissing my neck and holding me in his arms. It really made me feel like I was being cared for in a way that I hadn’t felt before. I felt seen by him, and present in the moment, while my anxieties dissipated into nothing.
The girls had all finally fallen asleep, and I could tell Marshall was getting ready to go to bed himself. He asked if I wanted to go upstairs with him to sleep in his bed. Of course I said yes, and we both walked into the other room, climbed the huge magnificent staircase, and went into his room.
His room was dimly lit but I could still make out his trophies and pictures with friends on the walls. While I soaked in his room he went to his stereo and put on some music. It was an old Madonna record that I hadn’t heard before, one of her earlier ones with the Minnie Mouse voice. I paused for a moment and thought to myself, “Do all gays have sex to Madonna their first time?”
“I paused for a moment and thought to myself, ‘Do all gays have sex to Madonna their first time?’”
I was just contemplating this gay right of passage when he moved over to where I was standing and started kissing me from behind. He started undressing me. It was very sensual, he was very careful with his touch, taking his time and touching every part of me. I started to let myself go deeper into the moment with him. Nothing else mattered, I was here, this was it.
We both got undressed and looked at each other. It was the first time a boy had seen me fully naked before, I was too scared to even undress for gym class so this was literally the first time a guy has seen me nude at all. He then grabbed my waist and started making out with me in his bed which put me at ease. I straddled him on top and felt his bulge against my backside. It was quite big, way bigger than mine actually, and I thought I had a pretty good size before. I felt comfortable enough so I told him I was ready. He pulled out some lube, applied it to himself and I, and told me to go as slow as I wanted.
I won’t get too graphic here, but it felt like it took nearly two hours, it hurt worse than anything I’d ever thought possible. He was incredibly patient with me, he knew what he was working with and knew it wasn’t easy for anyone their first time. However, I was on a mission. Eventually we got it in and he began pumping away slowly, while I was hurting so bad it felt like the wind had gotten knocked out of me. Was it supposed to hurt this bad? After we finished he pulled out and looked down to check if there was any sort of cleanup required. He wiped off and said nothing. I reached for my white shorts nearby and slid them back on, because even to this day, I don’t like sleeping nude. He had just crawled back in bed and put his arms around me when the next cd skipped over and “Like a Virgin” began playing on the stereo. What timing! We both rolled over laughing hysterically until we fell asleep, cuddling.
The next day it was time for the beach. Marshall and I both dressed and went downstairs to meet the girls. My ass hurt so bad that I thought I would die, but still we all packed up and got in the car. I sat in the back squirming in my seat while Marshall had his arm around me. He kept asking if I was okay but I whispered to him his dick was too big and I was still sore from last night, but I’ll manage. He laughed and just tried to keep me comfortable.
After the 45 minute ride, and what felt like forever, we arrived at the beach. We parked the car and got out, while everyone started walking towards the beach. Everything was going fine, it seemed. Marshall was walking behind me when I felt him grab my arm and pull me back towards his car. I asked him what was wrong and he grabbed me by my waist and started steering me towards the trunk. What was going on? He opened the lid and started fishing around when he pulled out a red sweater from the back and wrapped it around my waist. What the hell was going on?
“Don’t panic,” he said, “but your white shorts have a spot of blood on the back. I think it soaked through last night.”
Horrified, I looked behind me and, sure enough, a tiny, dime-sized spot of red was right there on my new white shorts, right in between my crack. He just smiled at me, finished tying the sweater around my waist, and closed the trunk.
“Horrified, I looked behind me and, sure enough, a tiny, dime-sized spot of red was right there on my new white shorts, right in between my crack.”
“Looks like someone’s cherry really popped last night,” he said with a chuckle.
I quoted Hedwig & the Angry Inch as a futile attempt at a joke to alleviate my horror:
“It’s my first day as a woman, and already it’s that time of the month!” He chuckled at my lame joke while we caught up with the girls. We never spoke a single word to them about what had happened. We just had a nice day at the beach.
To this day I’ve never told that story to anyone, in fact, he’s probably the only other person that knows what actually happened and as far as I know, he never told anyone else either. I was so embarrassed, but looking back I remember how special that was that my first time was with someone who was patient, kind, and kept the fact that I had bled through my white shorts a secret. It really made me feel well taken care of right at a time when I was feeling left out in the cold. He was more of a gentleman than most guys I’ve ever met since.
We broke up a couple weeks after that, and we saw each other around for years after, but have since lost touch. I hope he is happy wherever he is now. Maybe he’s away in New York and married to a rich investment banker living in that brownstone I had in my dreams. As for what happened after I got home that night; I definitely threw away those shorts, but I did keep his sweater for a couple years after. I guess it was my way of remembering that day.
-D.W.