Five Dares

by Eli Easton

  Jake’s negativity was seriously harshing my buzz. I thought he’d be down with this, excited even.

  “I’m sorry, is it too late for you?” I said mockingly. “What, were you wanting to get back to the dorm so you could go over to Kevin’s?”

  Jake physically took a step back, looking at me like I was crazy. “What are you talking about? I’m not . . . Why would I go over to Kevin’s at this time of night?”

  I shut my mouth. Damn it, why did I say that? It had nothing to do with anything.

  Instead of arguing with him further, I stood there and made myself breathe, made myself think through the stunt, try to see it from his perspective. I didn’t feel drunk or tired. I was fine, more than jacked up enough for a challenge. And it wasn’t as spur of the moment as he thought.

  I didn’t want to explain my thoughts about the stunt to Jake. I wanted him to be impressed, as impressed as everyone else would be, and maybe a little scared for me too. But that wasn’t going to work. Jake wasn’t going to go along with it if I didn’t give him some reassurances. And while he couldn’t physically stop me, it would fall flat if he didn’t play along. And I wasn’t sure I was ready to piss him off that badly.

  I sighed. “Okay. I have thought it through. I’ve been following reports of subway surfing pretty much since we got here. I figured I might want to try it one day. You know me, bro. I’ve always got a dozen ideas for stunts up my sleeve.”

  He looked at me warily. “Go on.”

  “I found a forum where people talk about doing it. This stretch here, from Spring Street to Washington Square, is a safe zone. Lots of people have done it. It’s a straight shot, not a lot of curves and no obstacles. I even saw a video of a guy doing it. It’s not really that dangerous.”

  He made a frustrated face and ruffled his hair with one hand. “But things change. What if they’re doing construction or something, and there are new obstacles? Or you could fall.”

  “Dude, how inept do you think I am? I won’t fall. Come on! This is way less dangerous than other stuff we’ve done.”

  “Maybe,” he conceded. “But I’m not as stupid as I used to be.”

  “Well I am,” I said firmly.

  I knew it would make him laugh, and it did. He chuckled and still looked at me like I was crazy, but I could see he’d softened. He was going to give in.

  “Come on,” I urged. “I’m not drunk at all. Swear to God. And this is perfect timing. It’s late enough that there’ll be few witnesses and both platforms will be empty. And we have some people with us to see it and freak out. What do you say? Please?” I pouted out my lip and gave him puppy-dog eyes.

  With a show of reluctance, he sighed. “Fine. I still don’t like it.”

  “Great! I need my wingman. Let’s scare the crap out of them. You in?”

  “Yeah. You get hurt, and I’ll kill you.”

  “Understood, bro. Understood.”

  We did scare the crap out of them. Jake played up the danger, talking about warning notices from the New York City Transit Authority and the various ways it could go bad. I acted a little bit drunk—didn’t want to overdo it. Amber and the others got emotionally invested, just as they should. Amber wanted the guys to “stop me” and Daniel said no, we should let Darwin’s Law play out. Asshat. But everyone was wide-awake now.

  At last the next train arrived and Jake got the group onboard. As soon as the doors closed and the train started to move, I jumped onto the outside of a door, gripping the sides the way I’d seen guys do on videos. The train rumbled and shook beneath me, giving me a rush as it went faster and faster. Jake stood on the other side of the door, palms pressed to the glass, his eyes locked on mine.

  Don’t you fucking fall, his eyes said.

  I stuck my tongue out at him.

  Like a roller coaster ride, it was over before I had time to really enjoy it. The train pulled into the Washington Square station, slowing, and I jumped onto the platform. As I thundered up the escalator, taking the steps three at a time, I heard a conductor or driver, some older guy, shouting angrily at me from down below. But he didn’t chase me. I waited for my group outside the station. I received my accolades. Amber refused to speak to me.

  We parted company with the last of our friends at the dorm, and Jake and I entered our room. He shut the door with finality as I turned on the light. Something about the sound of the closing door—not quite a slam, but close—made me turn to look at him. His face was stark and drawn. All the bravado and good humor he’d shown during the stunt was gone. And I realized it had all been a lie—Jake, the perfect wingman, had faked it.

  Before I could say anything, he stepped up to me and grabbed me in a hug. It was a crushing hug that was nearly violent, his arms going around me, pinning my own arms down. I could hardly breathe—I’d had no idea he was that strong. But I didn’t try to shake him off.

  “Fuck, are you trying to break my ribs?” I gasped.

  “Never again,” he said in a hollow voice. “Not like that. You tell me first. We discuss it well beforehand. And nothing like that, where we have no control and . . .” His words broke off like he didn’t know what he meant to say, all the conditions he meant to list. But I got the point.

  “Yeah. Okay.”

  “Swear?”

  “It’s fine, Jake. I told you it wasn’t really dangerous.”

  He shook his head, but he released me. A few minutes later he was in bed, his back to the room. I turned out the lights, slipped off my jeans and sweater, and got into my own bed in a T-shirt and briefs, not caring enough to brush my teeth or change my clothes.

  I lay there for a while, thoughts churning in my head.

  It hadn’t really been dangerous. Not any more dangerous and probably less so than other stunts I’d done, like the school roof parkour. But I’d decided to do it last minute and sprung it on Jake. And I’d pushed him to go along with it. And I had drunk alcohol at the club, even if I hadn’t felt drunk.

  I was uneasy, a little guilty. I’d been compelled to do it, needed to. Why? What drove me to show off like that? Amber? No. She hated my stunts worse than anything. We always had a huge fight afterward, something I knew I’d be subjected to in the next few days.

  Why, then, did I feel the need to do it?

  I thought of the way Jake had hugged me just now, grateful that I was alive, that I was okay. Was I really so jealous of Kevin that I had to prove Jake was still my best friend? Or was I trying to punish him?

  Whatever. It was way too much introspection for a Saturday night. Everything was fine. It was just a stunt. There was no point in getting hung up about it. I’d just be cool for a few months, and next time, I’d make sure Jake was in on the plans so he wouldn’t freak.

  I smiled to myself in the dark. There was always a next time.

  August 2017

  Jake

  It was our last two weeks together at the cottage, and all bets were off. We weren’t pretending anymore. Well, there were things I still wasn’t saying, couldn’t say. We didn’t discuss our feelings, God forbid. But there was no more pretending we didn’t want each other all the time.

  We feasted on sex like people about to go on a starvation diet. The jet skis languished unused at the dock.

  The next big step came two days after Andy fucked me for the first time. I loved it, loved that it was Andy taking over my body like that, and we did it in every conceivable position. True to his nature, nothing about it put him off or made him hesitate in the least. He was all gung ho. He wanted to know how it felt, from this angle and that. When he figured out the prostate thing, he became merciless in driving me to orgasm, usually with my hand flying over myself as he pounded me hard, though one memorable time he did the honors while taking me from behind.

  After the fifth time, though, I had to beg off for a day or so. I was getting too sore to bottom, as badly as I wanted to.

  That Monday was all blue skies and a heaven-sent breeze that blew away the humidity on the shoreline
. After breakfast, we played football out on the cottage’s back lawn. I was a little worried about hurting the baby-new skin on our palms with hard football passes, but Andy insisted we could throw the ball lightly, and so we did.

  We passed the ball and ran and generally burnt off steam. And then I tackled him onto the grass, facefirst.

  I refused to let him up, wanting to mess with him. Though Andy was a little taller than me, I was at least as strong. I held him down, spreading out over his back, pinning his wrists and trapping his calves under mine.

  “Get off, you ox!” Andy sputtered.

  “Not until you say ‘Jake Masterson is the best-looking, most intelligent human being I know.’”

  Andy laughed, but it was a choked sound with me pressing on his back. “You douche.”

  “Say it. Say—”

  “Jake Masterson is a disgusting human being.”

  “Um, yeah, not really close.” I bounced a little on his back, making his breath huff out like a deranged Santa Claus. Huh, huh, huh. “Say it.”

  “No.” He sounded breathless, but not distressed. I bounced on him a little again, hoping to induce him to cooperate.

  “Say ‘Jake Masterson has the biggest dick I’ve ever seen, and he really knows how to use it.’”

  Andy tried to laugh again. He thumped his head on the grass. “You know I could throw you off if I wanted to.”

  “Yeah? Let’s see it,” I dared him, tightening my hold.

  “Don’t want to.” He pressed his ass up seductively into my groin.

  The game went from funny to achingly sexy in a heartbeat. I got hard so fast, the grass spun a little. As if it turned him on to feel me swell against him, Andy groaned and pushed up again. “Do me. I want you to.”

  “Now?” I asked dubiously. It wasn’t that Andy and I had a timetable for sex. We’d pretty much done it any time of the day and everywhere inside the cottage. But for the past few days, Andy had talked about me fucking him but had never seemed that serious about it. And suddenly he was ready at ten in the morning?

  “Yeah, now,” he said, his voice gravelly. “Get off me.”

  “Get off you so we can get off? Seems a little contradictory,” I quipped. But I ground my hardness into his plump ass cheek and licked his neck. When Andy murmured a desperate noise, I pinned him down harder. “Say it.”

  “Jake Masterson has the biggest dick in the world, and if he doesn’t get up right now and fuck me with it, we’ll both be exceedingly sorry!” he declared, loudly.

  I chuckled, got up, and helped him to his feet.

  In his bedroom, Andy didn’t hesitate to strip his clothes or boss me around. “Get on your back. I want to lower myself onto that flagpole of yours.”

  “We need to open you up first,” I argued, nevertheless arranging myself, naked, on the bed, sitting with my back against the headboard where I figured Andy could get a good grip.

  “Then do it.” He crawled onto the bed, lube in hand, and straddled me, staying up on his knees.

  I took the lube and coated my fingers. They felt cold against the intense heat of his body. God, he was so warm. I circled behind his balls and around his hole, teasing, wanting to make this good for him. He didn’t rush me, just braced his hands on my shoulders, on either side of my neck, and let me work. His gaze was locked on mine, intent, and some part of him turned inward too, as if concentrating on the sensation. We only broke eye contact when I had to look down to put more lube on my fingers, and then to put the condom on.

  Like the fearless creature that he was, Andy sank down on me slowly, with widened eyes, black with a thin rim of blue, and with zero hesitation. I bit my lip hard, using pain to back off the pleasure, and wondered how I was supposed to ever move on from this, from having Andy naked and earthy and carnal in my hands, running full tilt at life, at sex, at me.

  I held his hips to support him as he began to move up and down. He had narrow hips, a very long waist, and a tiny mound of a belly, incongruous when the rest of him was still so lean. His thighs were muscled and strong, tensing and flexing as he rose.

  The tightness began to ease, and he began to go faster. I clenched my jaw against the waves of pleasure that wanted to spiral up too soon. I gripped his hips harder, needing to slow him down. He stopped utterly then, resting on my thighs. He leaned forward, wrapping his arms around my neck, and kissed me. And kissed. And kissed.

  It was so sweet, to pause on the knife’s edge of pleasure and just rock there, minutely, keeping the fire stoked. My eyes were closed, and I rubbed my hands over his back, loving that I could touch him this way now. I massaged him low, where only a thin wall of muscle separated my hands from my dick, buried deep inside him. Emotion rose up, and I thought I might lose it. I swallowed down every feeling, hiding them in a locked box inside my heart. This was not the time. Maybe there never would be a time, but right now, I had to make this good. Sexy good.

  He finally broke off kissing me to say, “It doesn’t hurt.”

  “Good.”

  “Definitely feels weird though, being on the receiving end.”

  I raised an eyebrow and held his hips to keep them still as I ground up into him. The slight teasing motion I achieved sent delight echoing through my shaft and balls. I licked my lips and gave him what I hoped was a sexy, half-lidded stare.

  “Lean back,” I told him. “Put your hands by my knees. Let’s see if I can find your prostate.”

  He did as I asked, spreading his torso back over my thighs. I raised his hips up and thrust into him. I was so hard there was no bend in my dick at all, despite the weird angle. He hissed in a breath when I stuck him deep.

  “That it?” I asked.

  He nodded eagerly. “God damn. What the hell is that? Do it again.”

  I didn’t take his question literally. He knew what a prostate was, it was just his first time feeling it. I supported his hips a few inches above me and began to seriously pound up into him. He threw his head back and groaned, kept groaning in harsh, staccato bursts every time I nailed him. The sounds he made, the sight of him stretched out like that, were almost better, more, than the sensation of his tight, hot channel. Sweat slicked me as I worked, giving him everything I had. I was determined not to stop and not to rest. His dick was stiff as steel as it bounced on his stomach, and a line of clear pre-come stretched with every bounce. He had to be close.

  I was close. I was almost beyond thought.

  “Touch yourself,” I gasped. “Almost there.” I had to see him come before I did.

  But he just raised his head to look at me. “Don’t need to. D-don’t stop. Jake!” His lips trembled and his face was flushed red. His expression was tense, one I’d seen a dozen times—it was the face he had when he came.

  I doubled my efforts in an inspired burst, pounding up into him for one second, two . . .

  “Oh God.” His head dropped back again. His dick began to release come onto his belly in a constant stream, not in pulses like a normal orgasm, but more like cream slowly pouring out of a cup.

  My hands clenched, and I curled forward as my own orgasm ripped through me, hot and sweet and intense as anything I’d ever felt in my life.

  Later, when we were rearranged, the condom had been disposed of, and my heart had come down from Mach 5, I whistled. “That was the first time I’ve ever seen that. Someone coming hands-free.”

  “Yeah. Weird, right?” He was lying on his back, one hand behind his head on the pillow. The other stroked my forearm lightly. “Never happened to me before.”

  “Not unheard of, but pretty rare, yeah.”

  “Once you started hitting my prostate I could feel something building inside me. It wasn’t exactly like a regular orgasm, but it was super intense. Longer and more . . . aching, maybe?”

  “Hmmm. So you liked it, then? Being fucked, I mean?”

  He rolled onto his side and threw his arm over my chest, limp as a noodle. “Yeah. Your magic dick made a bottom out of me.”

  I smirke
d. “Idiot.”

  He closed his eyes and appeared to go to sleep immediately.

  I lay there, my fingertips grazing his arm. I wanted to ask him: So what does that mean for your future? Will you have your girlfriends or wife peg you? Will you someday find another male lover to fuck around with now and then when you’re married? Or could you take or leave it? Would you be fine never repeating the experience again?

  I wanted to ask him those things, but I wouldn’t. Not later, when he was awake. Not ever.

  Andy was the brave one. Not me.

  Jake

  Inevitably, Friday the eighteenth arrived, our last day at the lake. The dawn came, despite me silently begging for it not to. I had maybe slept three hours that night, and I lay in bed in Andy’s room, watching the sky go from black to a dim purple to pink at the horizon. Time wasn’t on our side.

  I became too filled with nervous energy to lie still, so I got up and showered, leaving Andy to sleep.

  As I put on the coffee, Andy appeared. He came dragging into the kitchen in his PJ bottoms, looking about as uneasy as I felt.

  “Morning, Sleeping Beauty,” I said. “Nice hair you got going on there.” A tuft of Andy’s blond hair was sticking straight up in back.

  He gave me a half-hearted glare and poured himself a cup of coffee. We stood at the sink looking out the window at the sound together.

  “Had a text from my dad last night,” he said. “He has a client meeting at three, so he expects to be here after five o’clock.”

  I felt a trace of relief at that. At least we had most of the day. “Okay.”

  He leaned against me, putting his head on my shoulder, which was quite a trick since he was taller than me. I put my arm around his back and squeezed. We stood there for about five minutes, just looking out at the sea. I’d opened the window to get some fresh air, and the sound of the water lapping the shore was loud, mesmerizing.

  I was going to have a thing about the ocean forever now, wasn’t I?

  After a while, Andy gently pulled away and shuffled off to take a shower.