Role Play

by Alison Hendricks

  I felt his thighs start to tremble, and I knew he was close.

  "Fuck, I can't--"

  I clamped my lips around his shaft, using my tongue to urge him on. When I felt him tense beneath me, I relaxed my throat and let out a muffled moan as his jizz splattered against the back of my throat, shot after shot of it hitting. I swallowed it all down, giving his softening cock a little lick to clean away any stray cum before I drew my head back. After a moment, I remembered to pull my mask back down.

  He lay back against the bed, panting. Still technically in all of his clothes, though his shirt was pulled up to his chest, his fly was down, and his boxers were open. I couldn't help the smirk that tugged at my lips.

  "That the kind of thing you had in mind?" I asked, feeling damn pleased with myself.

  His eyes rolled back into position and he looked up at me with an intensity that sent a searing shot of lust straight to my own cock. I was painfully hard now, my dick straining against my jeans. I went for the buttons to give myself some relief just as he spoke.

  "Come up here and fuck my mouth."

  A shiver raced up my spine. I'd been with a lot of guys who tried dirty talk, but mostly they just repeated what they heard in porn. This guy was direct, telling me what he wanted to do to me and what he wanted me to do to him. I couldn't help but appreciate that quality.

  Not to mention it was hot as hell.

  Shucking off my shoes and jeans, then tugging down my boxer briefs, I climbed onto the surprisingly springy mattress. I had to get my balance, grabbing for the headboard. It might have just been a way to keep myself from falling at first, but I quickly saw the benefit as I climbed over him while he sat up so my dick was positioned right in front of his mouth.

  Gripping the headboard, I rolled my hips so my cock slid over his face. I could feel his lips part, heard his needy, whimpered moan.

  But, when nothing more happened, I realized he was waiting on me. Glancing down, I gripped the base of my cock and directed myself to his mouth, pressing the head between them. My legs shook a little as I felt him slide over the crown before pressing down to the shaft, and I returned both hands to the headboard.

  Then I did exactly what he'd told me to do.

  I started with strokes that were slow but getting deeper each time. Sliding into his hot, wet mouth, then pushing into his throat. He started to gag, and I pulled back, but his lips clamped around me and I caught the slightest hint of teeth. An accident, it seemed like, since his lips moved to cover them soon after. But the message he was sending was loud and clear: He didn't want me to stop.

  I pushed deeper, until I felt the head of my dick bump the back of his throat.

  "Fuck," I said with a groan, picking up speed.

  Before long I was fucking his throat in earnest, my cock bulging it. I used the headboard for leverage and kept on, feeling him adjust on the fly, his tongue curling around and under my shaft, one of his hands reaching up to fondle my balls at the same time.

  That was what broke me, in the end. I was making shallow thrusts into his mouth, faster and harder while he traced the seam of my sac, then rubbed his finger over my taint. My balls drawing up were the only warning I had before I shot, wave after wave of my cum flooding his mouth.

  He coughed, clearly not expecting it, but composed himself and swallowed, wiping up the cum that had dribbled over his lips even as I continued thrusting, spending myself completely.

  My thighs quaked, every limb feeling as heavy as lead. I drew out of his mouth and moved to sit down on the bed just to catch my breath. My heart was racing and, when I looked over at DorianGay, he was watching me with pure lust in his eyes. It was all I could see of his face, his mouth covered up again by the bandana, but it was more than enough.

  I needed time to recover before I could fuck him -- no matter how much I wanted to. It wasn't going to stop me from getting him ready, though.

  "Roll onto your stomach," I told him.

  When he did, I pulled off his sneakers and then his pants, following those with his boxers. Everything was tossed aside haphazardly, my only goal just climbing over top of him, my hands smoothing over his thighs.

  He wasn't out of shape. Judging from the tension in his calf and thigh muscles, he spent a lot of time on his feet. But there was an authentic softness to him. He definitely had a "dad bod," as my sister would have said. And God, I was crazy for it. So many of the guys I'd fucked were focused on making their bodies rock hard so they could really sell those ab pics. And sure, I liked to feel a guy's muscles as much as the next, but I also liked to get a solid grip. To feel a little give; a little cushioning softness. To hear the smack of flesh as my thighs snapped against his plump ass.

  DorianGay definitely had all of that going for him, and as I made my way up to his hole, I could see the little bit of fuzz that was in his pic. My hands rounded his ass, squeezing the generous swell of his cheeks. I gave a soft smack, more than satisfied with the wanton moan that escaped him as he pressed his cheek to the mattress. Another smack followed before I soothed the sting of red I'd left behind.

  Drawing my hand back, I brought two fingers to my mouth and sucked on them, then used my hands to spread his cheeks. His muscles trembled, so I only just skimmed the tip of one finger around his hole. When I started to press it in, I could feel him holding his breath. I could also feel how damn tight he was.

  Pulling back, I went to go search for the lube which was still in my pocket.

  "W-wait, I can relax some more--" he pleaded.

  It took me a moment to realize what he meant. "Just getting some lube. Don't you worry. I'm getting my fingers in that tight ass."

  I set the condoms on the bedside table and squirted some lube into my hand, coating my fingers in it, then rubbing it over his hole. Moving behind him, I tried again, pressing one digit in. With the aid of the lube it slid easily at first, meeting some resistance. Slowly, I pressed deeper and, as he breathed, his body relaxed. He was way tighter than I'd expected, considering how eager he seemed for this encounter. I could see him gripping the sheets, could feel the way his ass clenched around my finger.

  Part of me wanted to ask him if he was okay, but he'd already protested my getting up to get the lube.

  I took my time, though, and waited until he was relaxed enough before I started moving my finger in and out of him, searching for just the right angle to hit--

  "Ah!" he cried out in a gasp, arching back toward me.

  That was it. Right there. I massaged him slowly -- more slowly than he wanted, apparently, since he pushed back against me -- and reveled in the way he writhed beneath my attentions. By the time I inserted a second digit, he was moaning shamelessly, fucking himself on my fingers, definitely not too tight to enjoy it anymore.

  And fuck if I wasn't already getting hard again.

  Reaching down, I stroked myself while moving my fingers in and out of him. Finger-fucking him wasn't all I wanted, though. Not by a long shot. Lowering myself onto the bed behind him, I twisted my body so I could still stroke my own dick. My fingers withdrew from him -- something he responded to with a whimper -- but I was quick to make my intentions clear as my tongue replaced them.

  That earned the loudest moan yet, and I wondered if he'd ever been rimmed before, or if he just really liked it. Either way, I used my hand to hold back one of his cheeks and shoved my face in there, my tongue tracing around his hole, dipping inside and back out before I tongue-fucked him with enthusiasm, matching the thrusts to my strokes.

  I felt him shake all over, but his orgasm still caught me by surprise. His ass clenched around my tongue and the moan he let out was almost animalistic, his fingers clawing at the bedspread, his ass pushed back against me, drawing me in deeper.

  There was a sheen of sweat on his back where his shirt was still rucked up, and I had to resist the urge to lick it off in a long stripe. Being out of my mind with lust made me a little crazy, and holy fuck was this guy hot.

  I needed to be inside of him
. I needed to feel him squeeze like that around my dick; needed him to come with me inside of him.

  "I need to fuck you," I said in a growl, pushing myself up to reach for a condom and the bottle of lube. "Right now."

  7

  Elliot

  I'd always assumed my first time with a guy would be a slow, fumbling mess as I tried to figure out what to do with my body. It'd been that way with Barb, when we'd both been horny teenagers who knew what we wanted -- sort of -- but not how to get it.

  It wasn't like that at all with HelpingHands, though.

  Once I got over my initial nerves, I'd fallen right into it. I acted off of instinct, off of feeling, off of some raw, primal need I couldn't explain. I'd never felt this in tune with someone before, like I wanted to do everything in my power just to be as close to them as physically possible.

  And there was no way to be closer than to have him inside of me.

  Sure, I was still a little nervous. A dildo didn't compare to a real dick, and HelpingHands had one that wasn't excessively long, but was girthy. Cut and with a head that was going to feel so good pushing into my hole. Better than his fingers and tongue combined, I knew.

  Positioning myself crossways on the bed, I gripped the edge of it, the cool white sheets bunching in my hands. My thighs wanted to tremble from the anticipation of it all as I heard him tear the condom open, followed by the sound of lube squirting into his palm. I gasped at the sudden chill as he rubbed more of it over and into my hole, inserting a digit to get it in as far as he could. I focused on my breathing, knowing I needed to be relaxed for this or it wasn't going to be a good time.

  He could have just gotten himself lubed up, positioned his dick, then shoved it in unceremoniously. That was what they did in porn, especially in random hookup videos. The top just thrust forward and didn't stop until he came. I hoped he wasn't like that, and from how vigorously he sucked my dick and tongued my ass, I guessed he wasn't completely selfish.

  Thankfully, when I felt him position, the head of his cock nestling between my cheeks, it wasn't followed up by a slam forward.

  "You were really fucking tight when I was working you earlier, so I'll go slow," he assured me, his voice like velvet caressing my senses. "Let me know if you're uncomfortable."

  I nodded, unable to manage words. Idly, I wondered if I'd just gotten lucky in the Grindr lottery to find a guy who seemed to know what he was doing and wasn't just interested in using me as a cum dumpster.

  He pressed forward slowly, making it past my hole and toward that first tight ring. It was ridiculous to think it, but it almost felt like his dick got bigger once it was in my ass, expanding to fill me. Like one of those little dinosaur-shaped sponges that enlarges from a capsule when you add water.

  ...Which was the weirdest thought I'd ever had during sex. I chalked it up to a resurgence of nerves, especially when I felt his hand on my back. Just a gentle touch as if to reassure me. He withdrew, lubed us both up some more, then tried again.

  It took a bit of work. Me forcing my conscious mind and body to relax, HelpingHands exercising the patience of a saint. Inch by inch, he buried himself inside of me, and the sensation was like nothing I'd ever experienced before. I was right. There definitely was a difference. A dildo was silicon, and no matter how much warming gel you used as lube, it was never going to feel like a real dick.

  By contrast, HelpingHands' cock throbbed in time with his heartbeat, his flesh searing hot, that mix of velvety smooth skin and hard flesh rubbing against me in the most delicious way. I moaned, arching toward him, feeling his thighs flush with my ass. When he didn't start moving immediately, I wiggled my ass with an impatience I didn't know I could feel, and he chuckled.

  "I'm not going to break," I told him, accessing that inner, demanding brat Formerly Lonely Guy told me to tap into. "Fuck me."

  He drew back, the drag of his dick inside of me making my voice crack on a moan. Then, he drove forward in a stroke that was slow but full, repeating that motion over and over. All I could do was feel, one of my hands clutching at the edge of the bed while the other reached back to grab desperately at him, my nails digging into his thigh.

  He built speed, and before long he was slamming into me, his balls slapping against my ass. I was lurched forward each time, the bed creaking, mattress threatening to slide right off the frame.

  "Fuck yes," I practically sobbed as tension built inside of me.

  Every time he bumped against my prostate, I could see white-hot stars explode behind my vision, darkness rushing in as if I was going to pass out from the sheer pleasure of it.

  "Don't stop," I whimpered, beginning to push back against him until I was meeting every thrust with a slam backwards. "Harder."

  I felt his weight almost atop me and out of the corner of my eye I could see the muscles in his arm tense as he leaned fully over me and gripped the edge of the bed, right by my own hands. I couldn't understand why at first, but when his dick hit a new angle inside of me and his hips snapped more firmly against my ass, I knew. He was using it for leverage, just like he'd used the headboard.

  And God, it felt so fucking good. His large, powerful body covered mine, making me feel... safe and wanted, in a way I hadn't felt in years. He filled me so perfectly that I didn't know if I could be complete without this again. Or at least, I didn't know if I could get off without this again. That was a more reasonable thing to think when a stranger was fucking you senseless. Not that your life wouldn't be complete without him in it. That was insane.

  Trusting him to keep me where he wanted me, I reached back both hands, my fingers curling against the firm flesh of his ass cheeks as they flexed with every thrust. When he was flush with me I held him there, pulling him back whenever he withdrew.

  I could feel my orgasm building, churning like a volcano that had been dormant for too long. Despite the fact that I'd come not long ago, I knew this one was going to be different. As he slammed home over and over, I felt my body start to convulse, pleasure surging into every nerve ending. My dick jerked beneath me, my balls pulling tight. I cried out, halfway between a whimper and a moan as release overtook me, my cum splattering against the sheets beneath me.

  "Fuck, baby," I heard him growl, the endearment sending little sparks of pleasure through my already addled brain. "You're gonna make me come so fucking hard."

  He pounded into me for several more thrusts before burying his dick inside of me. I felt the moment he tensed, heard him suck in a breath. I even felt his cock twitch and pulse inside of me before a sound almost like a roar was pulled from his throat. Like he'd just conquered me; fucked me into submission and wanted the whole world to know about it.

  And I was perfectly fine with that, because the world deserved to know when it felt that amazing.

  I squeezed around him, reveling in his shudders and stuttered moans as I did so. Finally, he all but collapsed atop me, the heat from his body reaching me, the feeling of his weight something still so reassuring somehow.

  We lay like that for what could have been hours or just minutes. I couldn't be sure anymore. It was long enough to catch our breath and a little longer besides while my mind raced. Was this a one-off thing? It probably was, wasn't it? Guys hooked up and moved on all the time.

  Maybe another match on Grindr would be just as good as HelpingHands, but somehow I doubted that.

  He let out a groan and shifted off and out of me, pushing himself up to sit on the edge of the bed. I heard him take the condom off and dispose of it, and I rolled onto my back, my hand over my still-racing heart.

  "That was..."

  I let out a breathless laugh, because I didn't have words either. I wanted to tell him that was my first time with another man, and he'd made it absolutely unforgettable, but I didn't think that would go over well. Before I could say anything, though, his phone started to ring.

  At first, he ignored it. I got firsthand view of his tight ass as he rose from the bed and started to stride toward the bathroom. But when
the caller immediately tried again, he finally looked at the display.

  "Fuck, I have to take this," he said, a sudden panic in his features.

  "Yeah, of course."

  To the hotel's credit, the bathroom door was thick enough that I couldn't hear every word of his conversation. Something about a kid who was having a meltdown? God, was he talking to his wife?

  My stomach churned. It was amazing how quickly the good vibes could be sucked out of a situation just by the thought that I was helping someone cheat. When he came back out, his gaze was distant, his mind obviously not here.

  He finally looked at me and I tried to give a reassuring smile behind the bandana.

  "Go. Whatever it is, it's obviously important."

  "Thanks," he said hurriedly. "I..."

  I had no idea what he wanted to say there, and I was never going to find out. He dressed quickly, then hurried out of the hotel room, leaving me mostly naked, my stomach sticky with my own cooling cum.

  8

  Reuben

  I raced straight from the hotel to Mega Comics, speeding down Newberry Road. Pulling into the parking lot, I could already see Ruth and David, my nephew sitting on the curb, hands over his ears as he rocked back and forth.

  "Fuck," I breathed, barely wheeling my car into a space and throwing it in park before I leapt out. "David, are you okay?"

  He was mumbling something, repeating it over and over. I couldn't hear the words, and what little I caught I didn't understand. I knew I wasn't going to be able to talk to him about this until he calmed down.

  "What happened?" I asked my sister, standing in the parking lot while she stood helplessly beside David on the curb.

  "The owner said there was some kind of disagreement over the rules? I'm not sure. But you know how David gets about those things, and when people kept pushing, he just..."

  I came very close to yelling at my sister that she should have been watching more closely; she should have tried to deescalate the situation. But I knew this wasn't Ruth's fault, and I was finally able to understand what David was repeating.