Upping the Stakes

Up until college I’d never jacked off with anybody but myself. But Jake made it seem like that made me the weird one.

“Not even in junior high?” he said. I shook my head. “I don’t know man, my buddies and I used to jack off together all the time. My brothers taught me to jack off.”

I tried to act like I wasn’t shocked by that. I was an only child so it was all a little impossible to wrap my head around.

All I knew was that Jake and I were sharing a dorm room, had no privacy, and were horny as fuck. It was a month into the first semester and I was still finding my footing with school and campus life. Getting off was relegated to quick, quiet sessions in the shower, after which I’d ashamedly push my sticky load through the shower drain screen with my foot. I missed porn, and lube, and long edging sessions.

So when Jake started shaking the top bunk early in the mornings, there was a sense of relief mixed in with the surprise of it. Don’t get me wrong, the first time I fully froze up: like, is he doing what I think he’s doing?

“I didn’t wake you up, did I?” he said, after he’d groaned and crawled down the ladder to toss a balled-up sock in the corner and pull on some clothes. I shook my head. “I was jacking off,” he said, with only a trace of shame on his face. “Sorry. This lack of privacy. I can try and be quieter next time.”

By the next morning I was hoping he’d do it again, and when he did I found myself joining in. I wasn’t overly covert about it, and when he realized what I was doing he got louder, too.

“Nice,” was all he said once we’d finished, and we laughed. Then we did it again the next morning, and pretty much every morning after that. I was grateful for the release.

Then one night we were drunk and had just got back to our room and our hormones took over. I can’t remember who suggested it. But he pulled up some porn and we pawed at ourselves over our clothes for a while as we watched it. It felt pretty natural to take our cocks out and start stroking. And though it was weird to see him naked, it wasn’t a bad thing. Jake’s a good-looking guy - dark-haired, handsome, and fit. I was intrigued by his cock, which was as big as mine but I’d never seen another one before, in the flesh. He didn’t seem to care that I was looking and even made a comment about the size of my balls.

We blasted all over ourselves to a bukkake scene and passed out. There was some awkwardness the next day, but it dissipated.

And then it was on. We started jacking off together nearly every day after class. We'd do this thing where we’d compete to see how far we could shoot across our crappy dorm-room carpet. The loser would have to clean it up.

I went home that summer, and as nice as it was to have my privacy again, I missed our sessions. Jake and I got an apartment together the next fall, a two-bedroom with another friend of ours, Adam. We gave him the smaller room and took the larger one for ourselves. It was a lot bigger than our dorm room and we set it up with a TV, ratty couch and coffee table we got from Jake’s grandma. There was no bones about the fact that it was our jack-off spot, a fact we kept secret from Adam.

Pretty much daily we would lock our door, put on some music to hide the sounds of the porn, and get down to business, always to bukkake or gang-bang scenes. We never touched each other, but we looked a lot. It wasn’t a big deal.

The coffee table replaced the dorm-room carpet as the playing field for our competitions - it was pretty large, and if one of us cleared the edge of it we were pretty much guaranteed a win. That said, our luck flip-flopped, but there wasn’t any shame in cleaning up with our requisite cum rag, which a couple months into our lease was as hard and crusty as an old slice of bread.

It was Jake who suggested keeping track.

“We can mark off where we shoot on the table and use that to track our stats,” he said one day when we were in the midst of it, watching a girl on her knees going back and forth amongst multiple cocks. I laughed when he said it but it turned me on some, too. I was the first to blow that day, and nearly hit the edge. Jake stopped short of me by a couple inches.

“Nice, bro,” he said, and I got up to grab a roll of duct tape we had sitting around. He pulled off two pieces and stuck them next to our furthest shots.

“You should mark them with our names so we don’t forget,” I said, and he added our initials on them with a Sharpie. Then Jake cleaned it all up.

We had some laughs over those tape marks, but there was something hot about it too. The next time he won, and we added two more tape pieces to the table, this time with a number to indicate the round.

About a week later Adam was in our room and asked about them. I panicked but Jake was cooler than me.

“Tabletop football,” he said.

“Oh. I wanna play sometime,” Adam said, setting a beer down on the table that Jake and I had splattered with probably close to a hundred loads a piece. Jake shot me a smirk over his shoulder.

Not long after that, Jake brought up an idea.

“It’s kinda crazy…” he said.

“What?” I said. We were in our usual configuration, kicked back on the couch naked, a pump-bottle of hand cream on the coffee table and our greased-up cocks pumping in our fists like pistons.

“Well, we have this competition going, but there’s no real consequences. I’ve cleaned up your cum long enough to know that I don’t really give a shit if I get some on my hands.”

“Yeah…” I said.

“So what if we do a tournament? Track our wins and losses for a week, maybe. Then, at the end, the loser has to do something, you know, even worse than cleaning it up.”

“Like what?” I said, heart pounding. Imagining all sorts of scenarios.

“Like take it in the face. For instance,” Jake said. He looked over at me and kinda raised his eyebrow. “Too crazy?”

“Loser gets bukkake’d?” I said. “Way too crazy.”

“Yeah it’s all good,” Jake said. “Just a thought.” We kept at it, watching bukkake porn, of course. All those big dicks lined up and ready to shoot on some chick’s face. It was obviously one of our main fantasies, coating some beautiful girl’s face with seed.

“I mean, it’s not a terrible idea,” I said after a long silence. “As long as none got in my mouth or anything.”

“Yeah man, no way. Eyes and mouth would stay closed,” Jake said.

“Oh man, I don’t know…” I said. But on some level, I did know, and so did he, and we started the competition that day with his win, tearing a paper from my chemistry notebook for an official tally.

I won the next day, and the day after that. Then he won again. On Thursday we had our tiebreaker. It was a pretty charged session. I was honestly ready to cum from the outset but made myself hold off so I could build up a big load. When I finally did shoot and it went past the coffee table, we both knew.

“Fuck!” he said, still stroking his dong.

“That’ll be on your face next time, bro,” I said, shaking off the last drops. The coffee table was covered in ropes of my jizz, and he added his own a little later.

So that was that. The deal was, the next day, he would have his face ready for me to blast on. I was nervous about it and I could tell he was too.

But in another way it felt like Christmas morning. We both got up that day pretending like we weren’t just counting the hours till we got back home to jack off and square up.

“You guys want to go see a movie later?” Adam asked us.

“Nah,” Jake said, “We’re just gonna chill.”

I could see the trepidation on Jake’s face as we cued up a scene and got down to business.

“Just please don’t get any in my eyes,” he said.

“I’ll try man. Remember, this was your idea.”

“I know, bro,” he said, shaking his head.

We put on one of our favorite scenes, this gangbang with this really hot chick on her knees servicing like ten of the hugest cocks until she gets totally glazed.

“That’s gonna be you, dude,” I said.

“Fuck off,” Jake said, but we were both laughing. And even though he was acting like he was dreading it, I knew he was excited about it too. Part of me was even disappointed that I’d lost, that it would be interesting to experience it - only with Jake, of course, and not that I’d ever have admitted it.

The scene was ramping up and both of us were so hard and doing our thing where we get quiet and just focus on the scene, our gasps and moans doing all the talking while we stroke slow and edge. The chick had just taken her first load and there were nine more to go, but I knew I couldn’t hold off much longer.

“Alright dude,” I said, standing up.

“Yeah?” he said, looking up at me, wide-eyed.

“Soon,” I said.

“Okay. Fuck,” he said, and took a deep breath. He came around and knelt down next to me. We locked eyes for a minute and he got this reticent grin. “Do your worst man,” he said.

It wasn’t the first time I’d noticed what a great-looking guy Jake is, with his pouty lips and strong, stubbly jaw. Part of me was pretty excited to use it as a receptacle for my cum.

He closed his eyes but kept his face turned up toward me. As I edged I found myself thinking of blasting on him regularly. Or what if I started letting him blast on me regularly? What if that became our regular thing, alternating taking loads in the face, just cause it was fun, and hot?

Those thoughts sent the cum traveling from my nuts to the base of my cock, my orgasm ramping up until it was unstoppable.

“Alright dude. You ready?” I said

“Mm hm,” Jake said, nodding but keeping his mouth and eyes shut tight. He was hard in his hand, pinching and tweaking his boner as I stepped closer, bringing my rod inches from his face.

The first shot, for me, is a prelude. I aimed it at his forehead but it went a few inches short and landed on his nose, where some dripped onto his top lip.

“Fuck…fuck…” I said, gasping as my next shot came out. The second and third shots are always my main contenders, and these didn’t disappoint. A white-hot jet of jizz went right between his eyes, splattering his eyelids and sending more down the bridge of his nose and onto his lips. The next shot was even more copious, and in the throes of my orgasm, my legs getting weak and my aim getting sloppy, it went smack on his lips, splattering like a burst water balloon. He winced but didn’t turn away.

“Dude, holy fuck, sorry…oh my god…” I said as I kept ejaculating, what truly would have been a champion load had we still been in contest mode. I hit his forehead again, his eyebrows, his left cheek.

Jake whacked furiously at his cock as I coated his face. Then, just as mine was waning, he pushed his hips forward and, with a closed-mouth grunt, shot a wad of his own, the first shot of which landed on my leg. I moved quickly out of the way, laughing. And he reacted to my laughter by smiling as he continued to shoot on the floor. But his smile had the unintended effect of making some of my cum drip into his mouth. He shut it again but there was no way he couldn’t have tasted it.

He shot the rest of his wad and I surveyed the damage. His face was dripping with cum, he looked like he’d just been smashed in the face with a cream pie. He dropped on his back.

“Towel,” he said through mostly-clenched lips, but I was already on it. I dropped the towel on his face and he swiped it across him, exhaling as he cleared off his mouth and eyes.

“Dude. How much fucking cum was that?” he said.

“A lot,” I said, settling back on the couch as he wiped off.

“It sure fucking felt like it,” he said. “Holy fuck.”

“Sorry,” I said.

“Dude don’t apologize…you won the right. You did the damn thing,” he said. He looked at me. “I even got some in my mouth.”

“Oh no,” I said. Jake just shrugged.

“I dunno, it tasted kinda good,” he said with a smirk.

“Fuck off,” I said.

“Whatever dude, you made me your bitch, I might as well and enjoy it right?”

“Did it really taste good?” I said.

“Nah,” he said, tossing the towel to the side and sitting next to me. “But it wasn’t gross either.”

“That’s good,” I said. The porn was still going. Our softening cocks dripped between our legs.

“We really just did that,” he said. I nodded, eyes on the porn but my mind somewhere else entirely.

“I guess my time will come soon enough,” I said.

“Yeah and then I’ll cum all over your fucking face, dude,” he said, sticking out his tongue and slugging me in the shoulder.

I just shook my head, but inside I knew I was ready, no matter how the odds shook out.

Read Pt II here