The Philosopher

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I put this in the “first time” category, even though I don’t really have a first time that I can remember, because the true story given here is about someone I covered enough firsts with that it felt a little afterwards like I imagine being deflowered might have.


I’d just turned eighteen, had caramel skin, amber eyes, and a heart-shaped face, 5’5”, B-cup, maybe 130 lbs. I had some skin flaws I was majorly insecure about, the remains of a failed experiment with black hair dye on my head, and I wished I weighed a little less, but I felt overall attractive. I didn’t want a boyfriend but I wanted somewhere predictable to go for certain needs while I was in college. I thought it would be simpler that way, but I didn’t really know why and I under-estimated my reliable access to contraceptive, so things got dicey toward the end.

In my ad I asked for a partner who would wear a button-up shirt because I wanted to pretend I was the muse-woman of a famous philosopher. It was such an entertaining idea for me. Socrates himself attributed his wild success to having a shitty wife, and I knew I was capable of being rough around the edges enough to qualify. It felt a little more fun not to say that was the intended role or why it was so endlessly alluring, so I never did.

So many of my respondents were so much more attractive than I’d bargained for that I immediately felt like I was swimming. They were all good enough but I didn’t have all the time in the world to fuck all of them! I needed some way to filter everyone and find the best one, but I didn’t have any, so I just responded to whoever provoked my intrigue late into the night.

One guy in his late twenties sent a short reply without asking for a picture, sending one of himself, or describing his penis, but said he had a nice house and stable job. While others were sending me impressive photos of their erections stacked up against coke bottles and rulers and requested more graphic details of my own dimensions, something about his blatant not-sexiness fascinated me.

The possibility of him being some human trafficker with greater intentions than simply pleasuring himself or me was impossible not to consider. I wanted a challenge that I didn’t mind dying if I failed at it. It was around the time when the serial killer was going around the country meeting girls on craigslist, so I guess it was at least accurate to think that. I was an over-confident teenager and I’m glad I didn’t get myself into any real danger.

Another reply came in from someone a little older than I’d asked for, but he seemed so easy to talk to and I got a little excited at the naughtiness of sleeping with more than one person at once, something I’d never done before. He said he was divorcing his wife and couldn’t meet at his house, a pretense I was almost too innocent still to see though. I decided that whatever was really going on between the two of them was between the two of them.

He wouldn’t stop complaining about her and I thought it was funny to hear him make such a spectacle out of it. He sounded as insufferable as me when I felt annoyed by my parents about the fact I felt like a sexually starved animal. I didn’t care that he was a little overweight for my tastes or said that his penis was small because he wanted to meet a couple times and not have sex first, messaged me a lot, and reiterated that there was no way we would ever have any serious future. Opposite to the first person, it felt like I knew exactly what I would be getting into and that was comforting.

The next day I woke up to see that responses had continued to flood in after I went to be, and I had to get some school work done. I committed to reading my emails that night and hoping there wouldn’t be another batch just as numerous to read the next day. I hated the feeling that someone perfect might just barely miss me.

That night I was still high on the rush of seeing where the game would take me. I finished messaging all the gentleman from the night and began opening new emails. Knowing any one of my respondents would potentially having me feeling like I had to continue messaging them for days to come if I replied once, I bated my excitement until I’d opened all of their replies. My anticipation was tamped a little when I’d come across one here and there that said ‘hey’ or something like that. I wondered what kind of person I’d have to be to consider that enough information to hold onto in the deluge.

A little while into things, my cursor moved toward the email of one with an innocuous subject. I was already wondering if with two guys I already thought I’d be happy with that maybe I should be done trying to entertain the possibility of someone else. I might even be in over my head about either of the first two. Thrill already wearing off, I clicked on it and scrolled down to glance over all of it before starting to read. I saw that he had included a picture. Maybe a quarter or so of them did.

As soon as my eyes landed on it, I immediately knew I would be not-so-gracefully nixing mecidiyeköy escort plans with the first two guys and wouldn’t be wasting time answering emails from anyone new. My eyes poured over every pixel of that image of him in a swimsuit on a boat for maybe thirty minutes without reading his reply.

His features were unique and his body was muscular, but something about his relaxed, good-natured posture was the most captivating. He had a pleasant smile but was wearing sunglasses that I began to hate because I wanted to know what his eyes looked like. I quickly scanned his written response for something about his eyes but it didn’t seem to be there. I wondered who had taken the photo and where he was. It wasn’t some dimly-lit shot of someone’s muscular torso taken with a bathroom mirror like the others.

I’d already gotten well over a hundred responses by that point, and of everyone, without even reading what he’d said, his already seemed the most completely odd. I walked away from my computer and paced a little, surveyed my heaps of books all over the place.

One had a picture of Kierkegaard and that hair on the cover, another containing the masterfully artful writings of Camus, one about Sartre, whose appearance could only be fairly appraised as abnormal. I was seeking a philosopher. A philosopher would seem the most odd out of everyone else, wouldn’t he? I wondered. Yeah, the most thought-provoking one, that’s what I was looking for.

When I walked back, I deliberated over every letter that he’d written, every comma, one typo. I took in the information quickly and then recited it aloud in my thoughts. It was something about being interested in the role-play, and with how no one else had really said anything about that, the deal was sealed, but then he claimed to be hung too. Aww, I thought, he’s trying to distinguish himself but he’s only a quarter inch above average. I knew if he maintained interest that he’d become the philosopher.

I tried to muffle my excitement as I worded my reply, knowing what I’d wonder- was a nympho like me planning on rotating between like fifteen people or did he legitimately garner the most attention? Immediately following that, I wondered if he only knew what most guys would say and tried to come up with something different because he’d honed his skills on a lot of people.

We emailed a little back and forth for a few days. I tried to spin my words around the silent questions that were building. I would’ve sent him one, but he never asked for a picture and I never offered. I’d previewed how many other young, single, girls of average weight were making solicitations for free sex before I made my post. I wondered if he was feeling a little like he’d bought a lottery ticket.

I was a very average girl, decently pretty but definitely no jackpot, and I kind of laughed to myself in the days leading up to it, asking myself what emotional equivalent I might’ve gone though. I remembered going to the mall with my family a couple years prior and how I’d filled something out to win a new car because I was bored. Knowing my body and who I was, I felt like I could’ve told him upon showing up at his door holding a big poster, “Congratulations, you just won $300!!”

Meanwhile, I kept obsessively asking myself if I was really going to do it. I believed that he was good-looking, so my gamble felt a lot less glamorous. I knew what my parents would say if they found out. Depending on the prevailing weather patterns, I might’ve homeless in two seconds flat. My dad had tried to have me put in jail a couple times, had been successful putting other people there without much more reason than because they put him in a worse mood.

For that reason, I was somewhat appeased by the satisfaction I knew I’d get from doing something totally legal that would flagrantly tiptoe around my parents’ precious sensibilities. But all in all, it was my love for a story that instigated my decision that I wouldn’t mind it if the experience was my worst. He lived close to a community college campus I was attending, and so we agreed we’d regularly meet up after it finished for maybe an hour or so.

I deliberately showered before class that first afternoon and wondered what I’d choose to wear. I didn’t want to dress suggestively in front of my classmates, but if I didn’t feel attractive I wouldn’t desire anyone. I rummaged through my underwear and was reminded that I didn’t own and sexy clothes, and couldn’t. My parents would’ve caught wind and become suspicious. I anticlimactically settled on a t-shirt and jeans with probably too much makeup.

My first and most recent boyfriend had to wait six whole months before I’d let him turn the lights on and see my naked body. That was back when I was a lot skinner with no stretch marks and was experimenting with pretty light brown hair. Oh well, he’s just a stranger, I repeated to myself as I drove to class.

I tried pointlessly to pay attention, before ducking into the bathroom a couple times to make sure I looked alright kağıthane escort in the public mirror. I angrily fixated on a pimple I’d developed from nervously messing with my face a couple days before. I hoped he wouldn’t be the type of person who notices little things. Over that lengthy hour and a half, there were short lapses of attempts at jazz improvisation every now and then. At least the deep breathing soothed my nerves a little.

The sun had just gone down so the dry air was crisp when I finally pulled up to his house and got out of my car. My heart was vibrating when I walked up to his door. I knew I wasn’t going to turn around, I was too eager to see what crazy adventure there was in store. I heard the door opening and for a split second I wondered what I’d do if he looked nothing like the person in the picture I’d memorized, or if he’d be standing there pointing a firearm at me, but he was the same person and his hands were clear of any objects. Good start, I thought optimistically as I wondered what it felt like to bleed to death.

I stifled the urge to laugh out loud when I moved my gaze to take in the sight of him standing there. He looked silly in a button-up shirt, considering I wasn’t wearing a nice gown and we weren’t going anywhere. Then I remembered I’d been the one to request it. Ah, it’s the philosopher! I playfully reminded myself. Let’s see what he has to teach today. If I’d given the real Ph.D. I was ostensibly following the guidance of right then so much of my attention maybe I wouldn’t have gotten a C.

His returned smile was friendly, and I couldn’t believe my recklessness as I agreed to step inside his house. It was almost normal-looking to the point of exaggeration. I was extremely nervous walking back to his bedroom. I imagined the sadistic contraptions he had waiting there for me, but one of the first things he said when we arrived in a room with an adjacent bathroom but no knives or guns was that I was really calm.

I was too terrified to more than slightly smile, much less assure him that has never been true, and was especially not the case right then. My parents had no clue that I was over thirty minutes from home, somewhere different than where I’d said I’d be, and no one in our family owned a cell phone. His offhand comment set off an avalanche of internal chatter as I considered that I’d moved around a lot as a kid so I probably did seem casual and at ease while tried to memorize where the windows and doors were.

I was so not-calm that I had a surreal moment as I wondered if he was knowingly being blatantly untruthful to try to tranquilize me for the kill, but then I reassured myself that I had acted light-hearted so his accusation was plausible. I tried to channel the spirit of Duke Ellington and imagined how impressed my music professor would be if I theatrically belted out Take Five the next time I saw him so that I could think about something other than how nervous I was and at least convince myself that I was calm.

It felt like we both noticed at the same time that there was no place to sit down and become acquainted aside from his bed, given that he had roommates so the living room wasn’t ideal, and I settled onto it as politely as I could. His sheets were so nice that I was immediately suspicious. I wondered if he had a girlfriend who had selected them and I wasn’t the only pretender sitting there. I absentmindedly ran my fingers over the seams in the thick fabric wondering if it would be weird to ask where such quality could be purchased, because it still didn’t quite seem like we had an arrangement for a tryst.

I think he grasped it all felt a bit absurd for me, and I enjoyed the light small talk that he kindly offered in turn. He asked me what course I was enrolled in, and it felt a little like my cover was blown when he said he’d taken the same class the semester prior, but with the fresh smell of soap in the air, I discarded the idea that he was about to present on attempted murder for the eager pupil. He seemed to pick up on my silent conclusion and our conversation quickly warmed with lots of smiles and little laughs.

He was very observant to my body language. I felt like I couldn’t hide anything from him, and I’d worried a lot about that. But sitting there in some strange place with some strange person who I knew would soon be inside me, I felt so much like I was free-falling from an airplane that I didn’t care if I betrayed some honesty or if he didn’t like it.

I chuckled a little at how he quizzed me about my birth control, wanted to know if I’d met anyone else in the same way before him, told me that if I got pregnant it was my own choice whatever I wanted to do, and chided me for not caring that he smoked, saying it was stupid. He was such an adult, but he was only four years past my age and never finished college. He grew up in a small, poor town just outside city limits, his parents were still together. I wondered how he found himself responding to my sex ad when so much as looking at something like beşiktaş escort that was something that there was absolutely no question that the predominate men I was surrounded by would never do the same.

It was a strange vibe, so much that I wondered if he was going to be the one to back out. I’d asked for a no-strings-attached arrangement partly because I didn’t want to be hemmed into any particular course of action by unspoken obligations and expectations, and partly because I didn’t want to believe that my partner was. Still I answered his questions truthfully, reminding myself that he was such a random, unknown passerby that I didn’t have to pretend. Then he asked me why I’d chosen him. Quick, come up with something nice! I thought, A diversion!

“You’re very handsome.” He listened like he was unconvinced, but he really was handsome so that seemed impossible.

“I like your hair.” A smile was forming. Still he acted like he was waiting, so reminisced about a couple kids I knew in middle school who’d had red hair and talked about that a little, how his seemed familiar. I’d always thought it was so mesmerizing to watch how their hair had captured the light.

It was my first week of school at yet another school district when some rich, popular guy made fun of a girl with red hair by calling her “Snow White”. I called him an asshole, said she was beautiful, and inexplicably the three of us became good friends until I moved again. I thought my story might make him feel insecure so I didn’t mention it as I remembered all the stupid shit we got into together.

The philosopher’s face was still anticipating something, and I was starting to question my own motives. What does this guy want!? I thought. The truth, obviously, I rebuked myself. He’s the philosopher! I couldn’t tell him about his role, that would ruin all the fun. I couldn’t say he seemed completely peculiar, that might too.

In small exasperation I shrugged my shoulders and sighed, “I don’t know, you just seemed nice, likable.” I was lonely, home schooled. I’d always adored it when it felt like someone was performing an inquisition on me by using carefully-placed silence. He really did seem like a masterful philosopher, but I was just looking for a little company from someone who didn’t automatically assume I was wrong about everything. Sex was a fringe benefit.

He read my thoughts and asked me if I wanted just to be friends, and I paused in shock a little as I considered it. He was an obviously attractive male oriented toward females, I never guessed that could be an option. I was starting to decide that actually that would be very nice when he redacted his offer. He’d sounded relieved when he called me “actually cute” a few minutes before, so maybe that had something to do with him opting against it.

My lack of preparation really began to show when I asked him why he’d responded to me, and he just sort of stared back expressionless. Back then it was long before hookup apps, when Facebook was a young-person thing and a morning-after pill was something not covered by insurance or available without a prescription. Okay, okay, I thought, dumb question. I wistfully wondered who his lucky friends were but then my heart skipped a beat considering how those people might not get to hear how he sounded when he sprayed his cum like me.

Eventually he asked if I wanted to do it, and ‘it’ felt like our whole agreement to meet regularly. I’d explained that long-term, predictable sex was what I wanted and he’d been agreeable, but his question seemed almost worded intentionally ambiguously. You never know with those philosophers.

I’d been imagining feasting on a hard dick nonstop all day. That of someone with his physique would be more than adequate. I nodded, smiling again. I expected him to immediately tear his clothes off, but instead he asked a lot of questions about what I liked and insisted that all he wanted was to please me before initiating any physical contact or doing anything even mildly flirtatious. I’d never experienced anything like that before, someone almost mapping everything out before beginning anything, and to this day the degree to which he did it was other-species.

By the end of his planning session I was almost dripping wanting to go through all the information I’d just covered with him- I liked to be affectionate, I could almost come from having my nipples stimulated, I didn’t want him to eat my pussy, I loved to give head, we could start with missionary but doggy and spooning stroked my g-spot so I couldn’t get enough of them, and he was free to manhandle me however he wanted. When he asked if he could forgo a condom, I took a few full seconds to look over him almost zoomed out, but before I could, before my eyes, he masterfully assumed the shape of a tiny, wobbly puppy.

For all those lessons of sex ed indoctrination my parents had rallied against, I hadn’t even thought about it. I’d expected him to just do whatever he wanted and not share trifling concerns like that with me. I’d been fine with just assuming whatever costs he incurred on my own. With my thoughts ignited, I couldn’t help but translate. Would you please consider taking a greater risk at creating a teenage pregnancy with a completely unknown person than any sensible person would reasonably expect you to?

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