Five Dares

by Eli Easton

  “Nope, I’m doing it. I’ll show you.” Andy put down his red Solo cup, supposedly filled with the concoction of orange juice, grapefruit juice, and rum he’d been mixing up out of his trunk. He moved around to the passenger seat of his 2009 Beamer, weaving left and right, and opened the back door.

  “He’s so trashed!” Nate laughed.

  “Guys, don’t let him do something stupid,” a girl named Jayden said worriedly.

  Andy dragged his skateboard out of his car, staggering slightly.

  Don’t overdo it, I thought.

  Andy clutched the skateboard under one arm and waved his hand. He spoke loudly, motioning to other people hanging out in the parking lot to come over. “I, Andy Tyler, am going to skateboard from the roof of this building.” He waved a hand at the school. “From that point right there, near the stovepipe, or whatever that black thing is, back to here.”

  People began coming over. Even a few people at the football field began walking toward us.

  Andy waved at me. “Jake, my man, dare me to do it. Come on!”

  I pulled away from Denise and walked over to Andy. “All right. If you want to make a spectacle of yourself, I dare you. Skateboard down here from the roof, Andy. Let’s see you do it!”

  “He’s drunk, Jake!” Denise sounded appalled.

  “He won’t do it!” I said dismissively. I pushed Andy a bit on his shoulder, and he did a little wobble but stayed upright. “Anyway, he’s not that drunk.”

  “’M not that drunk!” he agreed unconvincingly. “And I’m boss on a skateboard. Been skating for, like, months!”

  I bit back a laugh. Andy had been skateboarding pretty much since he could walk. Our close friends knew that, of course, but most of the gathering crowd didn’t. He made some half-assed moves on the board in the parking lot, purposefully making himself look bad. The tension was building.

  Nate was taking bets and people were getting upset and worried. Some were hooting at Andy to go for it, but most of the audience was trying to talk him out of it, a few getting emotional.

  Gotcha.

  Finally, Andy bowed and announced that he was ready to start. “Jake, if you’ll be master of ceremonies.”

  “Sure.” I pushed off the car and away from Denise. I turned to address the crowd. “Ladies and gentlemen, do not try this at home, please! They say God protects fools and drunkards, so please send up a Hail Mary for our own Andy Tyler!” I raised my hands and clapped, encouraging everyone to applaud, but most people were too freaked-out to put their hands together.

  “This way, sir.” I turned to Andy and swept my hand toward the building.

  He started walking over there with me at his side.

  “Jesus Christ, you better not really be drunk,” I muttered to him when we were far enough away from the spectators.

  “Nope. My cup just had juice. I’m good.”

  “Be careful on that drop down to the second story.”

  “I’ve got this.”

  “Yeah, but you’ve never done it in the dark.” I really was worried, and it came out in my voice. “You don’t have to go through with this, you know. I can pretend that I decided to call it off.”

  “It’s fine, bro. Chill.” He snuck a glance back at the crowd and chuckled. “Fuck, they are shitting their pants.”

  “Do not screw this up. If we have to call an ambulance, I’m never speaking to you again,” I said darkly.

  Despite the practice runs he’d made, I was still paranoid. The sprawling school consisted of a main building that was old and brick with a peaked roof over a flatter, tar-papered section. Around the main rectangle were lower additions of one and two stories. There were lots of sloped concrete struts between the levels that Andy used to drop from roof to roof. There were a few sections that were tricky, and lots of ledges had deadly drops. It could all go wrong in a heartbeat. No matter how much you planned or practiced, some things were just inherently dangerous. But Andy was an adrenaline junkie, and when he got in a certain mood, there was no talking him out of things.

  Plus, I had to admit, he was really good on that damned skateboard.

  We reached the double doors that led into the back hall and the locker rooms. It was unlocked thanks to the football game. Andy would go inside and make his way up various stairwells to the topmost roof, and I’d stay out here and man the video camera—and the crowd. That was the plan. But when we got to the doors, he stopped and turned to me.

  “Jake.”

  “Yeah?”

  There was a big spotlight over the doors, and he looked pale, his pupils large and black with barely a sliver of ice blue left in his eyes. “Keep your eyes on me. Okay?”

  “Um . . . where else would they be?”

  “No, I mean it. On me.”

  “Sure.”

  He studied my face for a moment, his expression intent. “You’re with me. Right? It’s you and me.”

  “You know it.” I looked back toward the cars and Denise, feeling uneasy. If only Andy knew how much my eyes were on him—too often and for the wrong reasons. He’d probably hate me if he knew. But I was dating Denise now, and I was finally starting to get my head on straight.

  Andy grabbed my shoulder with his free hand and shook me once. “Say it. Say it’s you and me.”

  I looked at his face, my mouth dry. “It’s you and me, Andy. Christ.” I wished it were true, wished he meant it the way I wanted it to be.

  “Okay.” He sounded a little nervous. He dropped his hand. “Let’s do this. Make sure you get good video, especially that drop by the art class window.”

  “I’m on it.” I pulled out my phone so I could record.

  “And keep talking about how drunk I am.”

  “Yup. I know what to do. Don’t worry.”

  Andy grimaced. “Sorry. I know you’ve got this. You’re the best, Jake.”

  Andy turned to wave in an over-the-top sloppy style to the crowd in the parking lot. Then he winked at me and went inside with his skateboard.

  My stomach was in my throat for the next ten minutes as he swooped and dropped and wove, sometimes on two wheels. But he survived without a scratch. Nate made three hundred dollars that night. And my video, called “Drunken skateboard parkour,” got over a hundred thousand hits on YouTube.

  It would be a long time before Dunsbar High forgot the Andy and Jake Show.

  June 2017

  Jake

  I mentally went over my components class final exam while I took off my clothes to get into the shower. It would be humiliating to be hard in front of Walter.

  As he always did, Walter adjusted the temperature of the water until he was satisfied. Then he turned back to me. I’d managed to get out of my shorts thanks to Andy’s patented “wall wriggle” maneuver. I held up my hands, and Walter put plastic bags over them, sealing them with rubber bands at my wrists. Then he took my elbow and helped me step into the shower. He drew the curtain behind me to allow me time to get wet and relax for a moment under the water.

  So here was one thing I could have lived my whole life without experiencing: letting an older guy like Walter bathe me. It was surprising what you could put up with when you had no choice.

  “You ready?” he asked me through the curtain.

  I looked down. The exam questions on semaphores had done the trick. “Yeah.”

  Walter pulled the curtain aside and picked up the bottle of bodywash. He was good at this—efficient, fast, and thorough. Somehow he managed to make it impersonal, maybe because he never looked me in the face. He put bodywash on his hands, then rubbed briskly over my arms and chest, doing my pits too. When he got to my junk, he was a little too efficient. He only did one loose pass over them and then moved on to my legs.

  Was I clean enough? God, I was about to have Andy’s face down there.

  No. God, no, don’t think about that right now.

  “Can you, um, make sure I’m really clean in the, uh, groin area?” My face burned.

  Walter hesitat
ed for a moment, working over one calf. He grunted an acknowledgment. When he finished my legs, he put more soap in his hands and did another pass of the groin area, getting back between my balls with a brisk, clinical touch, getting everything super soapy.

  “That good?” he asked, standing up.

  “Yeah. Thanks.”

  He drew the curtain back, leaving me alone with my embarrassment to rinse off.

  Jesus, I had agreed to do it. I’d been warring with myself for two days now, and at this point, I was sick of thinking about it. I had battling factions in my brain. One side was like, Hey, this is your only chance to get naked with Andy, to get up close and personal with his dick, to get off together. Of course you should do it! And the other faction was all, You do this and you’ll never get over him! You’ll die of a broken heart at age forty surrounded by Star Trek memorabilia and cats!

  Left to my own devices, I probably would have opted for the safe choice—not to do it. But, as usual when Andy was in the picture, sanity went flying out the window like a teenager’s boyfriend when her parents came home. He hadn’t brought it up again, but I could tell he was unhappy that I’d turned it down—even hurt. For the past few days, he’d been getting more and more grumpy and irritable with horny frustration. Then this morning he’d looked so desperate, I couldn’t hold out.

  Well, I could. I didn’t want to. Besides, I was in nearly as bad a shape as he was. I hadn’t figured out a way to get off either.

  We were doing this.

  I got out of the shower before my thoughts could lead to another stray erection. Walter rubbed me down quickly with a towel and held out a pair of clean gym shorts. I stepped into them and he pulled them up. He didn’t say a word until I was decent.

  “You expecting company today?” he asked me as he took a comb to my hair.

  “No.”

  “Oh. I thought maybe your girlfriend was coming to visit.” His words were casual. Just something to say. Because I’d asked him for an extra-special wash of the pubes? I said nothing.

  After my hair was more or less in place, he put some toothpaste on my electric toothbrush and held it up for me. I moved around on it to get all my teeth and tried not to think about other things I could impale myself on.

  There was a prickling at the base of my spine and butterflies in my stomach. Were we really going to do this? It felt unreal. It wouldn’t have felt any stranger if I were expecting Santa Claus and the Easter Bunny to show up for lunch. With dildos.

  If Andy and I did this, I had two goals for myself: to enjoy the hell out of it physically, and to not get emotionally involved. Andy only saw it as a way to get off. I could hold on to that. I could hold on to it and not let my emotions get all tangled up in Andy again. Couldn’t I?

  Walter pulled the toothbrush away and filled up a small glass at the sink. He held it up to me, and I took a sip, washed it around my mouth, and spit in the sink. I turned and wiped my mouth on the towel on the rack.

  Next, Walter took the plastic bags off my hands and had me sit on the toilet while he took off the bandages and swabbed my hands. They looked about the same today, red and angry, and Walter’s ministrations hurt, despite his care and the numbing effect of the cream. But the pain was welcome for once. It cut through the dreamy fog in my head and made me focus on something real and mundane.

  “Anything else I can do for you?” Walter asked me when I was all clean and rewrapped.

  “No, I’m good.” I looked at the bathroom door, feeling claustrophobic. Thankfully, Walter got the message and opened it. A blast of cool air struck my face, and I sighed with relief. I could be alone for a few minutes to gather my nerve.

  “I’m ready for you, Andy!” Walter called out.

  I hurried down the hall to the guest room so I didn’t have to meet Andy’s eyes.

  Andy

  I drank my coffee and ate some French toast sticks Emily had left, using the forearm tool from med supply. I felt more nervous with each passing minute, and that had helped my erection vanish, which was a good thing for now.

  Walter called out that it was my turn in the shower, and I caught sight of a very clean Jake wearing only shorts going into his room. I took my shower, making myself think about anything but Jake while Walter was soaping me. Somehow, I got through the whole routine without embarrassing myself.

  Finally, Walter left, and the cabin went into that magic lull of calm it got when the morning rush was over. The silence felt like it weighed a million pounds. I forced myself to watch out the window as Walter drove off in his little Subaru. I didn’t want any chance we’d be interrupted. Once he was really gone, I raced toward the guest bedroom where Jake was staying.

  The door to the room was open. I skidded to a halt in the doorway. Jake was sitting on his bed, elbows on his knees, the Kindle propped up on the nightstand.

  “Hey,” he said, not meeting my eyes.

  He seemed nervous too. Did he seem nervous? I wasn’t sure, didn’t care. “Wanna do it now?” I asked quickly.

  He laughed. “Impatient much?”

  “Hell yeah! I’m about to burst. Aren’t you?”

  His grin faded into seriousness, and his Adam’s apple bobbed up and down. “Pretty much, yeah.”

  “Okay. So is this going to be weird? It’s weird, right? I don’t care. How do you want to do it? Here, or my room, or what?”

  I was being purposefully overeager and wide-eyed, just putting it all out there. It appeared to work. Jake’s tensed body relaxed. It was just us, after all. No matter what we were doing, it was always just us. We could do this.

  He wrinkled his nose. “Your room smells like socks and meatball subs.”

  “It does not,” I lied.

  “Here is fine.” He moved over to make room for me, using his elbows to shift his body weight.

  I started to get onto the bed, then changed my mind. I went to the wall and worked my ass against it to pull my gym shorts down. “Get naked,” I told Jake.

  He dropped his eyes, like he didn’t want to see me unwrapped, as it were. I caught a glimpse of red blotchy skin at this throat. But he scooted his butt on the bed to get his waistband down, and worked his shorts off his legs.

  I dove for the mattress, my dick hard and bobbing as I moved. It was weird to be in front of Jake like this, erect and blatantly out there. But the ache was back, itchier, hotter, and more insistent than ever. It was like my body knew I was about to get off and nothing was going to hold it back. And then there was Jake, sitting on the bed naked. His knees were up so I couldn’t see his dick. But his eyes were locked on my erection as I got onto the bed. I’m about to have sex with Jake. The idea was terrifying and also thrilling, the thrill of a really good dare. And, hell, it wasn’t like I’d ever been shy a day in my life.

  I sat down, thought for a second, then swung on my hip so my head was toward the foot of the bed and I was staring at Jake’s drawn-up thigh. “We don’t have to talk about this, do we?” I teased. “Because I could really do without an Oprah moment.”

  Jake huffed a tiny laugh. “No. We don’t have to talk about it.”

  “Good. Then shift over here and let’s do this. Don’t poke my eye out.”

  He huffed again but moved. And then, oh holy hell, then. Jake lay on his side, lowered his legs, and there was his dick. I had been hoping it wouldn’t be entirely soft. That would have been discouraging, like he really wasn’t into this, and also embarrassing given how hard I was. But he had a full-blown hard-on. It looked thick and heavy and bigger than I would have guessed from having seen him flaccid. It was a bit of a shock to be looking at another guy’s tumescent prick, but not exactly a turnoff. In fact, it made that adrenaline junkie pulse twinge in my belly, like I was doing something crazy.

  Then his lips closed around my head—his mouth improbably hot, the suction strong and so good—and I couldn’t stop the whimper that came out of my mouth. I had to do something before I started groaning like a chick in a porno, so I scooted closer and ti
lted my head to get him inside. At first I just wanted to plug up my mouth to stop the noises. But his hips jerked in surprise, and he made a low moaning growl and pushed a little deeper, like he couldn’t help it, and holy shit. Lust hit me hard, that slick, burning rush lighting up my body from the inside out—bam! Then logic hit me from the other side—bam! I was going down on Jake. I’m sucking a guy’s dick. The thought threatened to kill all the good feelings with nerves and uncertainty.

  I shoved the weirdness of it away, though. I was too much in need to stop this now, to let it be ruined. I tentatively moved up and down. He tasted, smelled, the way my hands smelled after I’d jerked off. There was so much of him to take in, it felt like I was choking, and I felt a flash of sympathy for the girls who’d given me head. I closed my eyes and paused, waiting to see if this was going to gross me out. But despite being unsure if I liked the act itself, my heart was pounding. What a rush. It felt so dirty, and so wrong, like I would shock people by doing it. At the very least, I shocked myself.

  I breathed through my nose. It was just a penis, after all, and I’d pulled my own often enough. I stopped moving my head and instead just sucked him like a hard candy, trying to get used to it, rolling him in my mouth as much as space and his rigidity would allow. I could feel the shape of his head against the roof of my mouth. The skin along his shaft was softer than anything I’d ever felt on my tongue, but it covered firm flesh. It was . . . sexy. Base. Raw. I rubbed the flat of my tongue up and down over the rim of his head the way I liked and . . . as if echoing me, Jake stopped what he was doing and did that to me too. He held me in his mouth, sucked lightly, and rubbed my ridge hard with the flat of his tongue.

  Oh gods above. That felt incredible. Lust washed through me again, fast and fierce, and suddenly my nerves vanished. The flesh in my mouth was exactly what I wanted. I liked being filled, gagged. I liked the way Jake trembled, like I was driving him crazy. And it was Jake. I’d thought about this before, but never expected to actually do it. My balls tightened and tingles shot up my spine.