Five Dares Read online

  Good question. Andy was a bright guy. It had probably taken him five seconds to figure out what had taken me months to wrap my head around. In California, I’d be starting fresh, and in a liberal environment. I’d already decided I’d be open about my sexuality, and Sierra had confirmed it was no big deal at Neverware. “I’ll come out, yeah. I like girls. I do. And maybe I’ll meet the perfect girl, and that will be it. But if I end up with a guy, that’s okay too.”

  But first I have to get over you. Which is going to be so damn hard. I didn’t say it. What was the point?

  “You don’t actually have a preference?” Andy’s voice was stiff.

  I searched for the words to explain. “With a guy it’s more relaxed. Less trying to figure out what the other person wants. Then again, being with a girl is easier in a lot of ways—being out in public, family expectations . . . I don’t know, bro. We’ll see who I meet.”

  “Yeah.” Andy’s voice was quiet, and his eyes dropped to the floor. His forehead was furrowed in thought. But then he looked up at me, his eyes burning again. “So did you do it with Kevin? Anal sex?”

  I sighed. Nope. Andy wasn’t going to let it go. “Yeah. Yes. Yes, I did. We did that.”

  “Which way? I mean, did you . . .”

  “Kevin. He, uh, thought of himself as a top. So we only did it . . .” Christ. “I bottomed. Once. It was fine.” I nodded stupidly.

  Andy’s gaze grew darker. “Just ‘fine’? That’s the descriptive word you choose for being fucked up the ass?”

  I wanted to growl at him. Though, granted, fine was a lousy descriptive word in any circumstances, much less to illuminate the experience of having a large dick rammed up my backside. “Sorry if I’m being subtle. How about ‘I don’t really want to get into the hairy details with you’?”

  “Screw that. Did you like it?” Andy insisted, taking another step closer.

  I had, in fact, liked it. It was probably my favorite thing Kevin and I had done together. Kevin had used plenty of lube and done the whole fingers thing and there hadn’t been any pain, just lots of new sensations. Extremely good new sensations. But afterward, I hadn’t liked the disconnect between the intense vulnerability of being taken like that and how I’d felt about Kevin at the time. It happened toward the end of our relationship, when I was starting to find him annoying. Also, he’d been way too smug about the whole thing, the whole “I Have A Big Dick” ’tude. We hadn’t done it again.

  “Well?” Andy demanded.

  “Jesus. Yes, I liked it. All right? It was . . . pretty hot and it felt amazing.”

  “I wanna try it,” Andy said at once, his voice hitching. “I want to fuck you. You can do me too if you want. But I have to do you. I want to know what it’s like. Don’t you want to see if it’d be different with us? You must, Jake. You’re just as curious as I am.”

  His words—talking about us fucking, the way his voice already trembled with lust—caused flames to lick up my spine, set my balls to boiling, and my swelling dick steered toward my stomach. My resolve crumpled to my feet, softly, like loose PJ bottoms when the elastic broke.

  “Jesus, Andy.”

  “I dare you,” Andy husked out, his pale-blue eyes lit with the fires of hell and burning into mine. “Jake Masterson. I. Dare. You.”

  Andy

  I knew I was pushing Jake. I knew I shouldn’t, not about this. But I couldn’t stop myself. There was that maddening, itchy feeling inside me, urging me on. At times like this, it felt like the inside of my head was going a thousand miles per hour, and if I didn’t make my body move, accelerate, drive forward to match pace, my psyche would break away from my corporeal being, and I’d become completely unglued.

  I was an explosion primed to go off, and I had to relieve the pressure.

  It didn’t take a Freudian analyst to detect the reason for my current anxiety—it was down to my dad’s call. I was utterly torn at the idea of leaving the cottage in two weeks. Speaking to him had been like a dash of ice water in the face—his no-nonsense voice, his iteration of all the practical details, everything that needed to get done before I started Harvard. He’d been so black-and-white about how it was time to get on with my life, like he grudged me this summer at the cottage, like he’d done me a huge favor by agreeing to it. Like there had been any other option.

  There was a massive disconnect between all of that and the way I felt anchored here, in this cottage on the sound with Jake. The thought of being torn away from it ached like I had stinging ants crawling inside me. It was inevitable, as unstoppable as time itself.

  “Come on, Jake,” I urged. “Let’s fuck. Right now. You can do me or I can do you, I don’t really care, but I want it.” I need it. Jake’s back was against the door, his hands flat on the wood, like he was a cornered rabbit. His face was conflicted. It would have been funny at another time, but now I just needed him so badly to agree, to want this too. I didn’t understand why he was resisting. He said he’d liked it with Kevin, and I knew damned well Jake and I had great sexual chemistry. These past few weeks had been ridiculous trying to pretend we didn’t want to go to bed together. He had to feel that too.

  I closed the last bit of space between us, leaning my chest into his, and then my hips. He turned his jaw away from me, being a stubborn ass, but I reached up and turned it gently back. I kissed him, soft for a second, then dirty, wiping the flat of my tongue against his lips, pulling back when he tried to chase it. I did it again, tempting him.

  He groaned. “God, I hate you.” He hooked his arm around my neck so he could hold me still. He kissed me hard, almost brutally, not letting me tease.

  I grabbed his hips and ground against him. I was already hard, thrumming with desperation-fueled desire and, if Jake was conflicted, his body was not. His hips arched against me, his prick like a stone. He spread his thighs, letting me sink deeper between them.

  I broke away from his mouth long enough to say, “You want me to fuck you? Or—”

  “Yeah.” Jake went after my neck with his hot, greedy mouth. One hand stroked down to my ass to pull me harder against him in case I had any misconception about what he meant.

  But I wanted more. “Say it. Tell me, Jake.”

  He tensed and grabbed my face in both of his hands. His brown eyes bored into mine. “I want you to fuck me, Andy.”

  “Because you’re turned on?” I demanded, still pushing for the brass ring. Goddamn it.

  “No, because I fucking want you,” he grit out, almost angrily. “I always—” He stopped himself, swallowed. “I want to do this with you.”

  I felt a surge of elation. “Okay. Great. So let’s do it.”

  I stepped back, grabbed one of his wrists, and pulled him along behind me. In my bedroom I had some lube I used for wanking, and there were two condoms in my wallet. I always carried a couple, but right now I wished I had a whole box. If I had my way, we wouldn’t be coming up for air until August eighteenth.

  We both stripped fast, sweaty T-shirts and shorts flying. It had been a hot day, and we were both grungy from the run. We could shower, but no way was I waiting for that. In fact, an extra twist of desire coiled in my gut as I looked at him. I wanted him like this—smelling strongly of sun and of Jake. Christ. I’d had no idea I had a sweat kink.

  I grabbed my wallet from the dresser and tossed the two condom packets on the bed. Jake had the bottle of lube from the bedside table. We looked at each other, standing next to the bed, both naked and crazy hard.

  “How do you want it?” Jake asked, his voice rough. He was trembling just a little. I’d never wanted anyone more in my life.

  Fast and hard. That was how I wanted it. At least this first time.

  “Get on all fours on the bed,” I said, my tone more demanding than I’d intended.

  Jake hesitated. “You have to prep me first.”

  I rolled my eyes. “No shit. I do know how to Google.”

  Jake’s intensity faded as he grinned. “I would have loved to hear Siri’
s response to that question.”

  “Christ, Jake, get on your knees!” I grabbed the bottle of lube out of his hand. My hands were shaking too, like some pathetic virgin. And as much as I loved smart-ass Jake, I didn’t want to see him right now. I wanted sexy Jake, panting and spread out in front of me like a buffet.

  He got on his hands and knees on the bed and then went further, lowering onto his elbows and putting his head in his hands as if in surrender. I had to stop after popping the cap on the lube and just stare for a second. Damn, what a picture he made with his ass up high, his thighs spread. His shoulders looked so broad like that, his back muscled and his ass round and tight. I could see his balls hanging down and the brown furl of his hole. It was pornographic. And hot.

  And, God, how much trust was he showing to open himself up for me like that?

  “Move,” Jake muttered, breaking me out of my stare.

  Hell, yeah. I squeezed lube onto my fingers and moved close to him. I held him by the hip with one hand and with two fingers of the other, spread the lube up and down his entire crack, squeezing his balls and making them slippery, rubbing my thumb over his hole.

  He made a noise, and his shoulders sank further into the bed.

  Despite my earlier claim, I was nervous. I knew what to do technically, but I’d never done anal with a girl, and I didn’t want to blow it and have to stop. I worked my thumb around, adding another shot of lube, until it could sink into him easily. He gasped and wiggled his hips, but it didn’t appear to hurt. I pumped my thumb in and out of him for a while till it moved easily. Then I went to two fingers.

  “Is this okay?” I asked him as he began to work himself back onto my hand, getting greedy.

  “Yeah. Just do it now. I want your dick.”

  Those words coming out of his mouth were so wrong and so unexpected. They sent a thrill through my body. “You sure?” He still felt tight.

  “Yeah. Come on, Andy. Don’t be shy now.”

  It might have been a joke, except his voice was too wrecked. I ripped open the condom packet. My fingers felt weirdly numb, probably because all the blood in my body was in my penis.

  I put more lube on the condom, then lined up, holding Jake’s hip with one hand. “Wish I could kiss you right now,” I said, then cringed at the words. I should be talking dirty like Jake, not all sentimental.

  But Jake just looked over his shoulder at me, his eyes wild. “Me too. Later. Just—”

  I sank in. The warm heat pulled me deeper like I was sinking into butter. He was soft and tight at the same time, sheathing me in perfect friction. I had to withdraw twice before I was able to thrust all the way inside him, as deep as I could go. He spread his legs more and tilted his hips. The next time I thrust into him, my sac slapped against his, a sensation so new and so shiver-inducing that I gasped a little. I did it again and again. Yet another new kink discovered. That felt amazingly filthy.

  Jake moaned, his head buried in his arms. “Christ, don’t stop,” he said, his words muffled. “Don’t stop, Andy. Don’t stop. Don’t—”

  I leaned forward, grabbed his shoulders, and began to pound into him, knocking the words right out of his mouth. God, I’d missed this, the sensation of fucking someone, the act of penetration, of sinking into a channel that had no obstacles and no end. Fucking Jake was perfect—seeing my cock vanish between those small, tight cheeks, feeling the muscles of his thighs and the slap of my balls on his, hearing his steady stream of moans, knowing I could ride him hard and he would beg for more, that it would never be too much for him to handle.

  He rose up on one arm so he could turn his head and watch. His face was flushed, his lips wet, his eyes dark chocolate. His other hand went to his dick, and he began jerking it in time with my thrusts.

  I wondered for a second if I was supposed to do that for him, but he looked so sexy doing it himself, and I was too busy fucking him hard to be bothered to slow down or change position so I could touch him. I was riding a cresting wave that was bound to drop, bound to thrust me up and spill me out like flotsam on the shore. His thighs shook. His eyes lifted and met mine, a dare in them. Now.

  We shipwrecked together, shuddering. His channel tightened spasmodically, almost painfully, around me. I felt every one of his pulses and lost track of where mine ended and his began.

  When I could move again, I collapsed onto the bed, pulled off the condom, and dropped it carefully next to the bed. Jake flopped to his stomach beside me. It felt like my heart was going to pound out of my chest. I couldn’t stop touching him, even now. The hand closest to him reached out, stroking his skin. He had really soft, supple skin with tiny freckles. It tasted salty-sweet, I knew, and I might be a little bit addicted. He shifted on his belly a few inches so his body was next to mine, touching all the way down. But his face was still turned away and it wasn’t good enough. I rolled onto my side and tugged at him until he was facing me. The look in his eyes was too much, and maybe what was in mine was too much too. He lowered his eyelids as if to avoid the intimacy. I kissed him.

  We kissed and kissed, softly, with no urgency except the desire to connect. We pressed together. I felt Jake’s stomach meet mine on each breath. His soft dick lay on my thigh, and I liked it. His fingers traced patterns on my back. My heart hurt.

  And, still, I held him.

  October 2015 - Junior year at NYU

  Andy

  It was a Saturday night, or more specifically 2 a.m. on a Sunday morning, and a group of us were on the subway returning to NYU after visiting a club in Brooklyn to hear a band called Crimson Folly. Besides Jake and my girlfriend, Amber, there were three others—Jay, who was one of Amber’s girlfriends, and two guy friends from our dorm who had come along. Daniel, with his light-brown skin and dreads, and Seb, a pale and freckled redhead, were sitting on either side of Jay, heavily flirting. They both obviously hoped to get lucky tonight, though whether they were competing or open to getting lucky together with Jay in a threesome wasn’t clear. Not that I cared what they did.

  We’d all been drinking, but the cold air outside the club and the fumes in the subway station had mostly sobered me up. And what the air didn’t do, my body’s chemistry did. I’d been worked up for days with that itchy, restless, rash-dash feeling prowling inside me like a caged beast. That inner turmoil seemed to affect my metabolism, because I’d barely felt the alcohol I’d had. I didn’t want to dance at the club, so Amber had danced with all the others, Jake included. I’d watched them, wondering what was wrong with me, and why I was in such a sour mood.

  It hadn’t improved by the time we were on our way back to NYU on the subway. In fact, with Amber leaning against my shoulder sleepily, and Jake across the aisle staring out the windows as if he wasn’t even part of our group, and Daniel and Seb both fawning over Jay, it got worse. My need to do something became unbearable.

  “We’re getting out at Spring Street,” I announced, just before we arrived at that stop.

  “What for?” asked Daniel.

  “I don’t want to walk,” Jay complained. “It’s too cold.”

  “Me neither,” said Amber. “It’s too late, Andy.”

  “I could go for some breakfast,” said Seb hopefully, because there were several all-night diners near the Spring Street station.

  Jake just stood up and stuffed his hands in his pockets as if ready to go. He gave me a questioning look, but said nothing.

  “We’re not walking,” I told them. “We’ll catch the next train. Come on.”

  The subway pulled into the Spring Street station and, without waiting to see if anyone else was actually going to follow me, I stepped onto the platform.

  There was no one around at this time of night, and the trains ran less frequently, coming every twenty minutes. I paced back and forth, running the idea through my head, making sure of what I intended to do and trying to judge my own sobriety. I didn’t feel drunk, only filled with that awful restless feeling that badly needed an outlet.

  When the train
pulled out, I found all my friends standing on the platform watching me.

  “So what are we doing here?” Daniel asked. He was another pre-law student and not a guy to keep his mouth shut.

  “A dare,” I said abruptly. “I’m going to subway surf to Washington Square. My man Jake here won a bet the other day and told me to come up with a dare. So this is it. This acceptable to you, Jake?”

  Jake was standing a bit apart to my left, so I was able to turn away from the group and give him a look. It was a look that said, Play along, Jake. Let’s get them good. It was a look that, I hoped, promised excitement and thrills. Now that I’d decided what to do, manic energy flooded through me, making me feel amazing, making me feel invincible. There were protests from Amber and Jay, but I wasn’t listening.

  Jake blinked at me, his jaw going firm and stubborn. “Give us a second, guys,” he said lightly. He gripped my elbow and pulled me down the platform and around the corner to the escalators.

  When we were out of sight of our friends, and presumably out of earshot, Jake turned to me, his expression worried. “What do you think you’re doing, Andy? This is way too dangerous.”

  “It isn’t,” I insisted. “Spring Street to Washington Park is only one stop. I’ll be fine.”

  “You can’t know that! People have died subway surfing. It’s not a good stunt, it’s just stupid.” He folded his arms over his chest, looking extremely serious.

  “Come on!” I scoffed. “Since when are you so chicken? Besides, you’re not doing it, I am. I just need you to play it up. You know the script.”

  “No. You’ve been drinking, it’s not safe. And it’s too late. You’re tired, we’re all tired. This isn’t the right time. Plus this isn’t like other stunts we’ve done, where you had it planned out and we practiced. This is just . . . I mean, what the hell, Andy? You want to hang on the outside of a moving subway train? You could hit an obstruction in the tunnels, or lose your grip and fall. No, it’s not cool. Really not cool, man.”