I’d just finished my first ever round of finals in college and I couldn’t really pretend that I was all that proud of my grades. I’d squeaked out a 2.9 GPA at the elite private university in Southern Virginia that I’d dreamt of joining my whole life.
Coming here was supposed to set me up for a long career of climbing the power ladder of corporate america, consulting, or government, but it’d been kicking my ass instead, threatening to make me look like the dumbest smart person in the room. What pissed me off the most was that I was competing against a rigged system/
It felt like every single person around me, which in the case of my school, was 80% male, had connections that were feeding them exam answers or helping with a professor for extra credit. Just getting in here had been nearly impossible for me with my average, middle class background, and now I was seeing that the legacy connections weren’t just of use to get in the door; they were helping my fellow students to cruise their way through freshman year. Everything was graded on a curve, so if half the guys had a built-in A, it meant I had to be at the very top of everyone else to stand a chance.
The other reason I’d come here was for the chance to join an influential centuries-old men’s club, called Aristos. The group was exactly as the Ancient Greek meaning would infer: a guaranteed pathway to power and success through its nearly limitless legacy network.
It had exactly fifty male members at any given time, which meant there were usually between ten and fifteen new slots each year. Three criteria determined those who got in: Intellect (grades), Influence (which usually meant a combination of family wealth and power), and ‘Value’. I was fucked on the influence piece, but I’d hoped grades would be a wash on intellect with other applicants. That had turned out to be a dud for me too.
On value, where the group was looking for people who could bring something unique to expand the network’s reach, I thought I had a leg up.
There’d never been a gay member, or at least an out one. While that wouldn’t have been surprising two hundred years ago, today it was a missed opportunity for business and influence that I hoped to help them bridge. It was a stretch, but it was the one thing I could bring to the table that no one else could.
Just before Winter Break, I’d gotten my interview. I was sitting down in a waiting area of their off-campus house, with another guy who I recognized from some of my classes.
“Hey man, how are you?” I asked.
He looked at me with the same judgmental eyes I was used to on campus, the ones that made clear that he came from money and could see right through me and my secondhand clothes. “Yo. What’s your name? You interviewing?”
“I am, yeah.” I expressed calmly. I was confident in myself, even if I was sometimes soft-spoken. “My name is Riggs, but you can call me Sawyer.”
“Riggs?” He made an ugly face.
I felt the same way he did, cursing my parents constantly for giving me a unique, southern sounding name that stood out so much. Thankfully, they’d given me a middle name that I could embrace and use in higher places of society. I usually didn’t even bother explaining that Sawyer was my middle name. “Long story. Just call me Sawyer.”
“Sure buddy…I’ll call you that.” He said, chuckling. I could tell his assumption was that he wouldn’t be seeing me around this house longterm, anyway.
“What’s your name?” It felt like pulling teeth to keep the conversation going.
“I’m Jeremiah.” He held out his hand and I took it. I knew his look from a mile away. The kind of guy that older adults thought was a sweetheart and respectful, but who was actually a shithead, privileged womanizer; someone who’d sell their friends out in a second to get ahead.
Jeremiah went in first and I was soon called into another room, just a few minutes later.
“Sawyer, huh? You’re from Louisiana?” A red-headed senior asked me.
“I am, sir.” I responded. He was barely older than me, but being respectful of authority was how I was raised. That submissive attitude carried into other things too.
I explained my journey. “Well, as of lately, Louisiana. I moved around a bunch as a kid, though. Louisiana, Texas, Florida, California. Military family. My older brother, Jake, is serving.” I’d hoped that would be another wild card positive.
“Is he an officer?” The guy asked, with a raised eyebrow.
I shook my head. He jotted something down and chuckled. Well, that had been a wild card, but maybe it was a negative one.
“Sawyer, your grades suck. You’d get kicked out if you have less than a 3.0 at the end of the year. And nobody here knows your last name.” The guy was blunt. “Why are you even here?”
I nodded, watching my dreams fade away. “I understand. But I’ve worked my ass off to get here, way more than the other guys you’re talking to.”
“What makes you so sure of that?” The guy asked. “You think you’re better than them because you come from nothing? Around here, that’s not a positive, kid.”
My heart was racing, but I knew I had to keep my composure. “I’ll get my grades up. That won’t be an issue.” I chose my next words carefully. “And I think I could do a lot to open up new lines of business and support with the gay community for our graduates.”
His eyebrow raised, “oh? Why is that?”
I made a suggestive head nod. “I think they’d understand me.”
“I see. Well, thanks Sawyer. We’ll be in touch…” He was dismissing me within five minutes of meeting me. I couldn’t believe he didn’t seem to have have the slightest interest in what I was pitching.
The next week at home was difficult. I’d gotten into the school I needed to, but joining Aristos was the guarantee for an easy life that I desperately wanted. When the call came, on Christmas Eve no less, it wasn’t what I’d expected. Somehow, for some reason, they invited me to join.
The unique deal was easy for me to agree to. It turned out that they liked my pitch and had done their own due diligence on the market that the businesspeople and politicians in their graduate ranks were missing out on. They saw the value in a young, handsome gay guy, especially one from the south with military family connections. When they looked at me, it was with dollar signs in their eyes. I was more than happy to serve that role for them if it was my slingshot to a better life.
But it wasn’t enough. They wanted more. They’d taken a vote and had an offer for me, one that at first made my jaw drop. They wanted me to not only serve the greater good of Aristos, but to quite literally serve the current college students of the group. It was simple; one day a week, all four years, no holds barred…and they’d even waive the academic requirements.
I couldn’t believe my luck. I could get in, have sex with a bunch of elite, straight men, and set myself up for future success? That was supposed to be difficult for me to accept?
Would could possibly go wrong?
----------------------------
THREE YEARS LATER: SPRING OF MY SENIOR YEAR
I was exhausted. It was Monday and all I wanted was to sleep, but instead I was sitting through a physics class that I had zero interest in, working to simply satisfy a general education requirement with a C. That C was also being taken care of by a family friend of my best friend in Aristos, Walker. The rule was that I just had to show up to class…which turned out to be annoying enough.
The weekend parties had been more tiring than usual this week. I should’ve skipped a Sunday fun day too, but the weather was finally above freezing, so I couldn’t possibly say no to all the guys when they were heading out to bars.
Monday also meant that the list would be out by midnight. The list. Both my favorite and least favorite part of the week. For three years, ever since January as a freshman, that list was used for Aristos guys to sign up…for me.
The rules were easy. I could decline anything if I really wanted to and there was a basic expectation of hygiene and testing. Given how poorly some guys did on the former, I really hoped that they took the latter more seriously.
Almost all the time, it was amazing, but every now and then, when a certain name or specific act appeared on that list, it made my skin crawl thinking about doing it Wednesday.
Not because I still couldn’t find pleasure in those moments, but more so because some of these guys were annoying jerks, felt beneath me, or needed to learn how to shower…
Wednesday at 8PM. That’s when my room opened up to run down the list. Guys waited in line, with a general time to arrive that I’d confirm just as the guy before them finished. Every single week since freshman year. As much I might complain sometimes, I was going to miss it badly when I graduated in a few months.
And man…it really made the numbers pile up. At first, guys were hesitant, unwilling to be labeled as gay or bi. But once they started talking, it was almost half the group that wanted to try it out with me at least once. I’d say that about eighty percent of the time, it was heaven. What gay college guy wouldn’t line up to suck and fuck a bunch of horny straight dudes?
And boy, were there a lot. I kept a journal to track it, to be exact. The number was a badge of honor: 36. That was the number of guys who’d fucked me since I’d moved in. Which was less than the 52 who I’d given head to, but a lot more than the 16 who’d been daring enough to ask me for a rimjob. I had some regulars, while others had only come once or twice in their time at school…those were usually some of my favorite guys; the more innocent, inexperienced, or lonely ones whose world I could really rock.
The only truly annoying part of the arrangement was their expectation that I shaved everything between my neck and knees, weekly. I cursed my genes for giving me a naturally furry upper body, groin, and ass, because it meant a constant, itchy, hourlong shaving affair. At first, I aimed to do it Wednesday mornings but, over time, I let them deal with stubble on my chest, above my dick, or in my cheeks. There were only a handful of guys who ever said anything, and it’s not like it stopped them from topping me anyway.
It did make dating pretty fucking hard, though. Like I said, you’d think every horny college gay guy would understand the position I was in. Most even joked, when they found out that I was in Aristos, that they were jealous to be around so many hot straight guys. Some even said they’d have given anything to get to have sex with a bunch of them. And yet, the second I told them that that’s exactly what I was doing, they were gone in a flash.
What did all of that lead to? Zero boyfriends and only four guys I’d actually had sex with under ‘normal’ circumstances all of college.
Was it worth it? You bet it was. I was on the road to unlimited freedom, success, and influence. If it meant sucking a few dirtier than I’d have preferred dicks along the way, then so be it.
3 Years Later: I rolled over in my bed to the morning light barely peeking in between the blackout curtains I’d put up last year. Tuesday already, huh? Time flies when you're counting down to hump day…which in my case, was quite literally ‘hump’ day.
The cutoff for the Wednesday list, which scheduled my ‘appointments’, was midnight going into Tuesday, so these mornings usually dictated what I’d need to do to prepare.
I honestly loved the arrangement at least 90% of the time. What gay college kid wouldn’t sign up for this? The other 10% wasn’t even bad, as much as it was just plain annoying. Even the ‘bad’ ones were still attractive and felt good, it was more just that I hated some of them for who they were, or for their lack of hygiene. It was a fine trade off, so I always checked that list first thing in the morning.
I propped myself up on one elbow, the sheet slipping down to my bare waist, exposing the little stubble under my belly button, which I’d recently shaved for my club mates. They liked it that way; it made it easier for them to have a smooth toy to play with, who was less of a threat to their straight identities.
I opened up the shared doc on my phone. Time to see who was lining up for pleasure tomorrow.
First name: Jeremiah. Of course. That asshole senior with the boy next door grin that fooled everyone but me. Fill you up. He had such a way with words. I’m sure his girlfriend thought he was such a sweet talker.
Might want a rimjob too if I'm in the mood.
Ugh. My stomach twisted a bit at that. Jeremiah was the biggest stereotype of a disgusting straight guy; he single handedly gave them their gross reputation. Sometimes, I wondered what he actually did in the shower, because he certainly wasn’t scrubbing anywhere that was hard to reach…
Last time he asked me to eat him out, it was like diving into a rainforest; musky, sweaty, hairy, and tasting like he’d just finished a twenty mile hike.
He's got a girlfriend that he's been stringing along for two years, who has no clue that every Wednesday, he's pounding me like I'm his personal stress ball. He could be fun in a rough way sometimes, but the personality? Terrible. I felt bad for the poor girl.
I scrolled down. Second up, as always, was Roman. I couldn’t even remember the last Wednesday that didn’t start with Jeremiah and Roman fucking me.
He was a charming, Indian stud with a thick, uncut seven inch (18) cock. The usual.
The usual was his weekly chance to change up the vanilla routine with his girlfriend of six years. He wasn’t as big of a douche bag as Jeremiah, but we didn’t really interact at all outside of these meet ups. I didn’t think we had anything in common, besides our shared love for a good pounding.
He was also a real man, unlike Jeremiah, and his hairy chest and beard always helped scratch a literal and figurative itch I had to get railed sometimes.
And then...third: Henry. The baby of the bunch; eighteen and fresh to Aristos.
Only three names this week? Weird. Usually it's four or five, leaving me a dripping, gaping mess by the end, cum leaking from both ends; throat raw, ass throbbing. But three? That's easy. I’d still have great energy when Henry arrived. Henry's request: Blowjob.
Same as always, since he joined a few weeks ago. He was such a sweet kid with messy brown hair and a goofy smile. His body was a little soft around the edges. The other guys gave him shit that he needed to hit the gym but I found him adorable. He had the perfect boyfriend dick, about five and a half inches (13cm) and cut. He'd blown his load in my mouth every week since he’d joined, and every single time, his eyes had gone wide like he couldn’t believe it was actually happening. And the way he moans when I swallow? Yeah, he was hooked.
I paused on his name, biting my lip. Henry's got this fat, jiggly boy ass that I’d been eyeing since day one. I’d offered on more than one occasion to eat him out, but he’d always been too nervous. I'd been dying to bury my face between those cheeks and feel them jiggle against my face as I tongue his hole. Clean him out, and make him squirm and beg. Hell, I didn’t even care if his hygiene level was at a Jeremiah level (if that were even possible).
The list was short, but my mind was already racing ahead to tomorrow night. 8PM.
I set my phone down for a second, my hand drifting under the sheet to my morning wood. Just thinking about them had me leaking, even Jeremiah. Jeremiah and Roman would leave me sloppy, but Henry...sweet, nervous Henry. I grabbed my phone again, my thumbs typing before I could overthink it.
Hey, bud. Excited to see you tomorrow. Take a good shower, just in case…for what we’ve been talking about trying. Ya never know!!!
I grinned, imagining his face lighting up red in his dorm room.
My phone buzzed a minute later.
Hey Sawyer. Haha okay. Don’t get your hopes up
I laughed out loud, stroking my now hard dick. This kid was adorable.
Trust me, you'll love my tongue in there. I could make you cum without touching your dick
Henry: lol idk we’ll see!
I stopped touching myself, not wanting to blow an orgasm on alone time before tomorrow. That night, I drifted off hard as a rock, like I did every Tuesday. I dreamt of boys and cum: my favorite things on earth. Wednesday was great, but the buildup in my head and the anticipation were half the fun.
The few minutes leading up to 8PM every week were the longest of the week. My dick would start leaking like crazy by 7:45, anticipating what was coming.
That was also about the time that I usually started fingering myself. Tonight was no different. I slid my hand down into my gray sweatpants, lazily reaching around my hairless balls and taint, and fumbling around near my hole with a lubed up finger.
I learned by sophomore year that these straight idiots had no clue about the prep that went into anal sex, so I’d started taking care of loosening up myself, before the night got started. Jeremiah had been starting me off the last two years, so I knew this was the best thing I could do for my own sanity. Luckily, once he got done with me, I was easily loose enough for the entire night…
A knock came at 7:57.
“Come in.” I yelled out.
He opened it up and came in, looking pissed and impatient, which probably explained why he was early. “Pants off.” He grunted, already stripping off his shoes and pants.
That smug grin was incredibly unattractive. He wasn’t a bad looking guy, but he thought he was better than me, simply because of the families we were each born into, as if he thought he owned me. I guess in some ways, he did.
I rolled my eyes but slid my sweats and briefs down in one motion, positioning on the mattress on all fours. I arched my back just enough to make the offer obvious; it had become a habit and not something I did enthusiastically.
“I gotta hurry up tonight.” His voice was blunt. We both knew what this was. “Girlfriend wants me to stay over. Gotta get a nut out in you, so I can last a while with her.” He snorted a laugh, but I thought he was pathetic.
I twisted my head. “How would she feel if she knew you were going from my ass to her pussy once a week?”
His hand slapped across my left butt cheek; it was sharp and it stung, but it was also perfect. “Shut the fuck up.”
“You gonna even shower before you stick it in her?” I kept it going, getting him worked up so he’d at least keep my attention.
Another smack.
I bit back a yelp, to make it sound like a laugh. We’d been through this dance so many times, that we usually got right to it. He lined himself up behind me and I felt the tip of eight, thick inches (21cm) pop inside me. Even three years later, it still made me wince. Of course a guy like this would be lucky enough to have this hammer.
He would never admit it, but I knew the full two minutes he took to bottom all of his gigantic cock inside me was his version of being gentle. We didn’t like each other, but he thankfully wasn’t a monster. We both knew how much he could have ruined me if he shoved it all in at once.
After those two minutes though, I could feel that mess of practically unwashed pubes poking against my cheeks and my insides being stretched out by a massive invader.
“Fuck,” I hissed, my forehead dropping to the mattress. He’s too big, always is, but when he breaches that second ring, deep inside, it makes my toes curl.
“Good to go?” He asked. The only thing he’d probably say that was remotely ‘nice’ for the next fifteen minutes. I nodded back and braced myself.
With that okay, he pulled those eight inches out and began his uneven, unrhythmic hammering. My cock leaked onto the bed, the traitor that it was, while Jeremiah was destroying my insides.
He yanked my hair, forcing my back to arch further. “Take my cock, pretty boy. Be my bitch…” Another spank, harder. I clenched around him on reflex and he groaned.
I pushed backed, meeting him thrust for thrust. “Cmon man, fuck me. You’re not good this week.”
He growled and slammed deeper. My moan was half pain, half filthy gratitude. The headboard thudded against the wall in time with his hips. I could feel every vein, every pulse. He was already close, I knew the signs by now.
“Gonna…” He didn’t finish. I felt him bury his entire dick in me and, for a second, I thought I might fall over from the pain searing through me. Deep, deep inside, much deeper than anything should’ve been, I could make out the warm feeling of his cum pouring into my guts. He stayed in there for just a second, before pulling out with a wet sound.
It was always the strangest feeling when the air hit my hole after Jeremiah, mostly because he left it completely gaping and wide open for everyone else. I clenched it, trying to remind myself that it still worked, which also pushed a trickle of his semen out to run down my leg.
Jeremiah slapped my ass one last time. “Roll over, bitch.”
I flopped onto my back, my chest heaving. He turned around and shimmied himself backward, straddling my waist. His hairy ass was staring at me, looking disgustingly musky and sweaty. “Clean me up.”
I wrinkled my nose but I’d done worse. I tried to hold my breath while my tongue darted out, tracing the fuzzy rim. There was hair literally everywhere; all over the cheeks, along the crease, on and practically in the hole. He sighed, settling his weight down.
He only did this to humiliate me. “Good boy.” Sixty seconds of lazy rimming and he was, dressing again. “Later, Sawyer, good job.”
The door slammed. I was barely done catching my breath, my hole throbbing and soaked in semen when the next knock came. Roman.
He stepped in, his dark eyes flicking over me sprawled naked and freshly fucked. “Jeremiah, right?” he asked, already shedding his jacket.
“Yeah, the usual. No one in between you two ever signs up.” I wiped my mouth with the back of my hand, tasting God only knows what.
Roman tossed off his shoes and unbuttoned his shirt. His chest hair was thick, curling over dark skin. Six years with the same girl and he still fucked me every week like they’d never had sex.
He circled the bed, his already hard dick in his jeans, bulging. This used to be a much longer, less ‘hot’ process. Roman spent the first year making me clean out again after Jeremiah. In fact, the first time he saw Jeremiah’s cum leaking out of my whole, he almost ran out of the room to throw up. But by year two, he was impatient and finally gave it a go. Then, he realized that Jeremiah’s cum was the perfect lube to give him a smooth, slick ride.
He freed himself, and a thick and uncut dick flung out, before he peeled the foreskin back to reveal a glistening, ripe, never quite fully clean, head. Where Jeremiah was dirty and brutal, Roman was much sexier, so his rawness only added to his allure. His dick was just a little shorter than Jeremiah’s, probably around seven inches (18cm) and just as thick.
He gripped my hips from behind and slid through the mess that Jeremiah had deposited inside me. My moan was long and shaking, my hole straining at being invaded once again.
“Fuck, you’re sloppy tonight. He must’ve been building up a big load.” he muttered. His hand slid up my spine, pressing between my shoulder blades until my chest hit the mattress. My ass was up in the air, taking every thrust.
He’s also usually louder than Jeremiah, grunting with almost ethereal sounds that I could never make out. At this angle, his balls started slapping against my taint. It was a shame that his girlfriend was so vanilla because he really knew how to fuck. I helped him go deeper, reaching back and spreading my cheeks wider, and he moaned to approve of the move. “Goooood boy, Sawyer! Spread em for me!”
“Yeahhhh…” was all I could moan back.
“Girlfriend tried to ride me last night,” he panted. “Lasted thirty seconds before she tapped out. You…” He slammed deep. “You’re a good slut, Sawyer.”
I laughed breathlessly. “Mhmmm. She’s so lucky to be with you…”
I tried to sneak a hand down to stroke myself but he slapped it away. “Stop that!” He didn’t usually want me reminding him what I had down there.
We settled into a nice rhythm for a minute, letting the only sounds be the steady smacking of his bottoming out against my ass. Every thrust inched me closer from pleasure to pain again, but I knew he’d finish before we crossed a threshold I couldn’t take.
Two minutes, maybe three, and he was there, rubbing my back and losing his rhythm. Once again, I felt my insides go warm. “Busting in you.” He kept it blunt and I closed my eyes to embrace the seed flooding through me again. We stayed like that, sweat running down my forehead, until he pulled out with a groan.
He ruffled my hair with surprising affection, and headed for the door. “Thanks, Sawyer. You okay?”
I was still on my knees and this time, even without squeezing my hole, I could feel the cum leaking out of it and spreading down toward my taint. “Always. You were awesome.”
“Thanks, man.” He responded. “Clean up a bit before Henry. Night, dude.”
And he was gone.
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