Jon From High School

by Jeremy Jenkins

  I knew he was a virgin, he was telling the truth. He was a virgin in all the ways that counted.

  It was up to me to show him this world of sensations that he’d been missing out on all this time.

  No. Not missing out on.

  He’d been saving himself.

  Saving himself for me.

  My cock ached as another pang of desire shot through me.

  I rained kisses down his hard body, lingering on each button of his abdominal muscles.

  He moaned and writhed. I could feel his skin tense and shudder under my lips.

  When I got next to his hip bone, I stuck out my tongue and painted a long stripe of saliva from his side to his crotch, but withdrew my tongue right before I touched his cock.

  His body bucked.

  I smirked.

  How does it feel to have something so good and have it yanked from your grasp, motherfucker? I thought menacingly. Then I swept the thought away.

  This wasn’t about revenge.

  But somehow, it was. It was about evening the score.

  At the same time, it wasn’t. It was about reconnecting.

  …it was confusing. I didn’t have time to think about any of that right now—I had Jon Preston spread-eagled on my bed beneath me.

  Revenge. Reconnection. Did it really matter when you were naked?

  I’ve heard it said that love and hate were two sides of the same coin. Sure, I’d never loved Jon Preston, but I certainly had had an obsession with him as a teenager. Thoughts of him were braided into all of my emo music and my dark moments alone.

  Isn’t that what teenage love is all about?

  Wanting something you can’t have?

  There was a cruel beauty in that.

  I rolled off Jon, and my sweaty back collided with the cool sheets.

  He panted next to me. I could feel the question marks coming off of him, along with the sweat.

  “What’s the matter?” he asked.

  I didn’t say anything. Instead, I grabbed him, and tried to guide him so he was straddling me.

  I didn’t know what I was doing. All I knew was that I wanted him on top of me for a bit. I wanted him to press me into this mattress; make me feel small.

  Make me feel like garbage, just like he used to.

  It was no fun if I was the one bossing him around with no fight.

  A smile crossed Jon’s face as he rolled on top of me.

  His weight pressed me into the sheets, then his lips crashed onto mine again.

  I didn’t have to think about anything here, between Jon and the mattress.

  Just like that night by the campfire, when he pressed me against the dirt.

  His lips molded around mine, just like that night.

  I could feel his abs grind against me as he moved. His cock rubbed against mine.

  We were both hard as rocks.

  I loved the sensation of him on top of me. Every kiss was a reminder of how things could have been.

  How things should have been.

  He rained kisses down the side of my neck, leaving electric footprints in his wake.

  My body shuddered uncontrollably and the thick, hot desire pulsed in my lower belly.

  Sure, I’d had other lovers since Jon. This was nothing new.

  But at the same time, there was something about Jon that made it feel…

  Made me feel so right.

  Even if our minds weren’t aligned, our bodies sure as hell were.

  And that… that made me feel something I had not felt since then.

  This realness. This deepness.

  This passion.

  It was passion. Pure and raw.

  I could feel it with every kiss. With every touch. I could see in his eyes that he’d never stopped thinking about me.

  I answered the questions in his eyes with kisses. But these weren’t standard, sloppy hookup kisses. These were slow, sensual. They meant I miss you, and I want you, and most of all, I see you.

  Our bodies gyrated together, perfectly in synch.

  Our hands explored one another, lingering on every crease and shape in our differences.

  But the differences were nothing but the positive and negative space between us.

  We fit perfectly together. That much was undeniable.

  He pulled away from the kiss and gave me a long, loving look. Even in the darkness, I could see the glimmer in his tawny eyes.

  He looked older than he was; much older. Like a man that had lived lifetime after lifetime searching for me.

  We both knew it was time.

  Then the question arose between us: who would be top and who would bottom?

  Thankfully, he spoke first. “I’ve… I’ve never done this before.”

  I knew what he meant, but I needed to know for sure. “Never done what before?”

  “…anything with a guy.”

  “You mean bottoming?”

  “…yeah.”

  His eyes glimmered in the light. I could tell he wanted it, and by telling me that, he was being vulnerable. Maybe it was his first time being vulnerable with someone, too.

  I didn’t want to hurt him. “You don’t have to if you don’t want to—”

  “I want to,” he said, the words slicing through the darkness. “I’ve wanted this for ten years.”

  We interlaced our hands and I bit my lip.

  If he was a virgin, there was no way he could take me without hurting himself. And I didn’t know if he knew the basics of anal sex. There were questions I needed to ask. Safety questions. And there was no way to ask them without killing the mood, so I just went ahead and said, “Did you—”

  “Yes,” he replied.

  My eyebrows came together.

  “I used the bathroom this morning. I know… I know what to do in theory. I’ve looked it up online and all of that.”

  I smiled as relief flooded through me.

  My cock pulsed with glee, excited to press itself into this virgin jock’s tight ass.

  Fuck, that was all it had ever wanted…

  “Are you sure you want this?” I asked, looking deep into his eyes.

  He nodded. “I’ve never stopped wanting it. I’ve never stopped wanting you.”

  I opened my mouth to reply, but all of my words had gone. There was nothing left to do but consummate this thing between us.

  Slowly, we got into position: Jon was on all fours on the bed in front of me, and I was behind him, staring at his bulbous, muscley ass.

  I already had the lube and condom out on the bed, ready to go.

  I dug my fingers into the sides of his ass, marveling at how round each cheek was.

  And best of all, I could feel his body quivering with anticipation.

  With every fiber of his being, Jon Preston was begging for my cock. I could feel it in the light shudders from his body. I could see his cock dripping pre-come on the sheets in a long, silvery thread.

  And me? I was stiff as a rock.

  I rolled on the condom. I had to special order these XXL ones, and even then, they felt tight.

  It felt like my cock was fighting to get free of them; begging my brain to bury itself in an asshole bareback. Sure I wanted that, but safety was more important.

  My cock sheathed in rubber, I pressed it against Jon’s ass, exploring.

  I knew he could feel the blunt head of my cock against him.

  I could see it in the way his muscles strained as he held still.

  Then, he moved his ass backward, as if his hole was begging for me.

  God, that was so hot…

  I felt another pang of desire pulse through me; that primal hunger that told me I’d die if I didn’t get satisfaction soon.

  And his hole was right there…

  But I’d have to wait. I wanted to milk this longer, and plus, he wasn’t ready yet.

  Honestly, I didn’t even know if he’d be ready if he was the most lubed-up and relaxed he’d ever been. It crossed my mind for us to get stoned and try it,
but then I swept that thought away.

  I squirted a dollop of lube into my hand and rolled it between my fingers, warming it.

  When I touched him, he jumped a little.

  I didn’t know if it was from the lube, or if it was from the fact that someone was finally touching him after all this time.

  I swiped my fingers in between his ass cheeks as he moaned.

  His ass bubbled up to me; a gesture that begged for more.

  Who was I to deny him?

  I spread his ass cheeks and peered at his tight, virgin jock hole.

  Oh my God, it was so small! The thing was just a tiny pucker.

  With a sinking disappointment, I knew that I wouldn’t fit.

  Not tonight, anyway.

  But there were still other things we could do.

  For a fleeting moment, I considered sticking my tongue in there and rimming him, but the lust was already thick in the room.

  From the way he was pushing against me, I could tell he wanted something inside him.

  There was no need to tease anymore.

  So, I leaned back, slipped my lubed-up finger between his cheeks, and started moving it around and around the rim of his hole.

  He moaned and I watched his head buck back.

  I smiled, and a foreign feeling within me danced with delight.

  I loved being on top of him like this; finally having Jon Preston underneath me, all vulnerable and begging for my cock.

  I pressed my finger into him, past the tight band around his entrance.

  He hissed and withdrew.

  “Sorry,” I said, “Does that hurt?”

  “Burns,” he said.

  “We can stop if you want,” I said, trying to keep the disappointment out of my voice.

  “No. Keep… I want to do this.”

  “Alright,” I said, half reluctantly, half gleefully.

  We waited for a few breaths, frozen in the moonlight. Then, “Ready?”

  He nodded.

  This time, I pressed the tip of my pinky finger into his ass.

  He hissed again.

  I was about to pull it out, but he said, “No—leave it.”

  So I did. I was just there, naked in this hotel room with my pinky finger in Jon Preston’s ass like some kind of fucked up finger puppet.

  So many feelings coursed through me:

  Revenge. Power. Trust. Compassion.

  And fuck, that cocktail made my dick so hard, I was sure it could cut diamonds.

  Slowly, I felt the tight band of muscles around my finger relax.

  So I slipped in another digit.

  He arched his back and moaned.

  Then, I began moving it in gentle circles, adding lube, and getting him all loosened up for me.

  I added another finger and repeated the process.

  He moaned and bucked against me.

  I reached around and wrapped my other hand around his cock, jerking him off.

  His moans peppered the air.

  It was like he’d never experienced pleasure like this in his entire life, and fuck, I didn’t think I had, either.

  I didn’t know if I was getting off on the fact that I was finger-fucking a virgin, taking my power back from my high school bully, or the fact that something about this sex felt so real.

  Probably all three.

  But before long, I was close to coming just from doing this.

  Then, suddenly, he whispered, “I want it…”

  “You want what?” I asked, teasing the answer out of him.

  “I want… the dick,” he said breathily.

  Fuck yes.

  I knew I wouldn’t fit. But I had to try.

  So, I stopped jerking him off.

  I knew he was about ready to come anyway. I could feel his body ready to release, treading so close to the edge of that canyon of pure pleasure.

  It was now or never.

  So I withdrew my fingers from his tight little asshole and watched it contract as he moaned.

  Jon had himself propped on his elbows, his massive, muscley ass in the air. In my face.

  Everything I’d ever wanted was right in my face.

  I grabbed my massive shaft and guided it to between his ass cheeks.

  He let out a slow breath.

  The sound sent a shudder of pleasure through me.

  I touched my tip to his hole.

  Every instinct in my body compelled me to press into him, hard. To shove myself inside of him; make him feel an ounce of the pain he made me feel when I was a kid.

  All the times he bullied me in middle school. Shoved me against lockers. Called me names. Spread rumors. He’d made my life a living hell, and now I had the opportunity for the most primal, satisfying revenge.

  I would have done it, if I was fucking Jon Preston.

  But the man underneath me wasn’t Jon Preston. He was just Jon.

  He was just a confused, closeted guy that I shared this connection with.

  It horrified me that I felt compelled to ram into him like that. That I even had the temptation to do so in the first place surprised me a bit.

  But he pressed his ass against my tip, and all those thoughts ran away.

  I’d have time to deal with them later.

  Right now, I had Jon’s ass gaping and begging for my cock.

  So I did what anyone in that situation would do: I pressed my tip against his hole gently, watching as it struggled to flex around my firm head.

  “Ah…” Jon sighed.

  “Relax…” I whispered, running my fingers along his lower back.

  I felt the tiniest amount of give. He was relaxing for me; it was working.

  Jon was opening his body to me. But he wasn’t just doing that; this act felt like more.

  He was opening his soul to me; baring himself open and giving me the power to hurt him.

  I could have hurt him. I could have made him pay.

  But I promised I wouldn’t. I promised it with the way I touched him; the way I caressed him. The way I moved around him.

  I wanted him to feel good.

  Goddamit, I still wanted him to feel good…

  Hot tears swelled at the corners of my eyes.

  I didn’t know why they were there. Why the hell were they there?

  Jon let out a breath, and his hole gave a little more.

  I pushed a millimeter inside of him.

  The sheet tensed.

  My eye went to his hands—he was grabbing bunches of the sheets, pulling them.

  Desire swelled in my lower belly again. I was going to burst just looking at that…

  But I had to keep it together. He told me what he wanted, and I had to try my best to give it to him.

  I grabbed his hips and pressed a little further, easing my head in millimeter by millimeter, then—

  “Stop, stop!” he cried.

  I pulled out immediately.

  He collapsed on the bed, then rolled over, panting.

  He draped his arm over his eyes, as if to hide them from me.

  I laid down next to him. “Did I hurt you?”

  Jon moved his arm, revealing one amber-colored eye. “It hurt. But you didn’t hurt me, no.”

  I understood what he meant.

  “We don’t have to do it,” I said. I could feel my cock begin to deflate in disappointment.

  “I’m sorry. I want to,” he said. “I’m just… not used to it, I think.”

  A half-smile curled on my face. “It gets better the more you practice.”

  That lit a fire in his eye; I could see it. He didn’t like losing. He wanted to do more.

  “Let’s try again,” he said softly. “If you’re up for it.”

  Delight surged through me. “If you insist.”

  We got into position again, and I squirted another dollop of lube into my hand, rubbing it between my fingers.

  I thought I’d ruined everything. I thought my chance was gone. I thought we were never going to be able to fully consummate the bond betw
een us; all the wind had been taken out of our sexual sails, and this was the only chance we’d ever get. Jon would make an excuse and then escape, trying to erase the awkward moment from memory.

  But here he was, embracing it.

  Wanting to try again.

  So I massaged his tight little hole with the lube, and positioned the head of my cock at his entrance.

  He made a sound with words on his breath.

  “What was that?” I asked.

  “I said I want you to fuck me,” Jon said.

  And just like that, I pushed in.

  12

  Jon

  My ass was screaming, but I kept my lips pressed tightly together.

  Anal sex. This was something I’d always been curious about, since I first started hooking up with Victor all those years ago. I tried to tell myself that I was just curious; interested to explore this area of human sexuality that I’d never been to before.

  I mean, I heard stories about guys getting a finger up their ass all the time and loving it, so how was that any different than a dick? It was just an organ. It was just stimulation.

  But over time, my fascination with Victor’s massive girth grew. The obsession latched into my mind and wound around everything else, tying all of my thoughts to the memory I’d held onto since that day by the campfire.

  When I’d first seen it.

  Honestly, I’d searched and searched my whole life, but never found anything that equaled Victor’s size. It was bigger than anything I’d seen in porn. Bigger than anything I’d seen in any locker room—though honestly, I’d never seen him flaccid.

  That filled me with a foreign sense of satisfaction.

  Was this how women felt when they had sex? Where the power was in the validation that you were turning the guy on? Because, it was impossible to not see how much Victor was turned on.

  And that… that inflated my ego more than anything I’d ever experienced.

  He paused his insertion, and I knew he had only put in the very tip of it.

  I didn’t know if I’d ever be able to take the length.

  But the longer we lingered here, our heartbeats matching in the darkness, the more relaxed I felt. I could feel myself ease around him.

  He pushed in a millimeter more, and I felt a burning pain.

  “Too much?” he asked, his voice all breathy.