Role Play

by Alison Hendricks

  DorianGay: God, I bet you'd fill me up so good.

  HelpingHands: Show me what I'll be looking at when I'm behind you, getting ready to stretch your ass open with my fingers.

  He'd asked for a pic. Why shouldn't I? Plus, I really wanted a visual to go with the thoughts I was having, because holy fuck did I want this guy.

  He sent a pic not long after, and it was everything I could've hoped for. A round, plump ass, just a little fuzz around the puckered hole, one of his cheeks spread for me to see. I caught sight of his sac, too, hanging low between his hairy legs. Biting down on a groan, I stroked myself ever faster.

  Now, not only was I imagining railing this beautiful man until he begged for mercy, but also moving between tonguing his hole and sucking his balls, or even feeling those balls slap against my ass as he fucked me.

  It was the last thought that made me come. My cock pulsed as I shot my load, splats of cum landing on my clothed stomach. I'd stupidly forgotten to strip out of my shirt first, so that was definitely going to need to be stain-treated immediately. I hadn't made a gaffe like that since I was in high school.

  Even still, the first thing I did as I caught my breath was message DorianGay back.

  HelpingHands: I wanna meet up. Tomorrow night?

  There was such a long pause that I had time to clean up, put my dick away, and get my shirt in the washer before he replied.

  DorianGay: 9? The Holiday Inn by Walgreens? I'll send you the room number.

  HelpingHands: Sounds perfect. Can't wait to see you.

  And God, I really couldn't. Something about this guy was drawing me in. I knew it was only going to be a one-time thing, but I was looking forward to making the most of that night.

  5

  Elliot

  Oh God.

  I had a date.

  I had a date with the hottest guy I'd ever seen. Or... the hottest abs and dick I'd ever seen. Only, it wasn't a date. I needed to remind myself of that until it stuck. We weren't going to get dinner and talk about our hopes and dreams. We weren't going to go play mini golf and maybe catch a movie.

  We were going to meet at a 3-star hotel (at best) and fuck.

  My stomach twisted as I realized just what I'd gotten myself into. He was expecting somebody smooth. Or at least, somebody who knew what the hell they were doing. I'd never touched a cock that wasn't my own and, while I'd had plenty of experience taking a strap, I was positive taking a real dick would be different.

  As I sat on my couch, my own cock soft now, cum cooling on my stomach from when I'd jacked it to his picture just a few moments ago, I couldn't help but think I was out of my depth. Panic filled me to the brim, threatening to spill over. I itched to tap out a quick response telling him I was... I don't know. Otherwise booked up tomorrow. Then I could just ghost him and pretend this never happened.

  Instead, I opened my email and found the thread with Formerly Lonely Guy.

  The last message he'd sent me had been advice about conforming to a role in conversation. Since I had a pretty strong interest in bottoming, he'd suggested I be the cock-hungry bottom who knew his ass was worth a hard fuck. The kind of guy who could make his partner come just be working his ass muscles the right way, squeezing him as he stroked in and out.

  I wanted to be that guy, but I didn't think I was. In fact, I knew I wasn't.

  It doesn't matter, he'd said. Keep it up for half an hour, maybe an hour at the most in person, and no one will be the wiser. Then you can go your separate ways and you never have to think about the guy again.

  He'd written it so plainly, like it was common sense. Maybe it was for gay guys. Maybe this was just how Grindr worked. I'd seen porn that was supposedly taken with a phone during a random hookup. Pump and dumps, most of them. I could do something like that. I wouldn't even have to talk, and I could get behind the idea of maintaining anonymity that much more.

  Then again, with how I'd talked to him on the app, he might expect me to engage in dirty talk. I... didn't know if I could do that. I decided to write back to Formerly Lonely Guy, sending a long, rambling email.

  Dear Formerly Lonely Guy,

  I have something set up for tomorrow night. What's the hookup etiquette? Do I bring condoms and lube? Does he? I should probably bring some just in case. If I'm bottoming, I don't want to be without them in case he isn't considerate enough to bring them. Though I guess there's a Walgreens right next door if I need. Not that I want to leave a hookup to go into Walgreens. That would be weird.

  God, sorry. I've never done anything like this. Can you tell? That was rhetorical. I'm sure you can. I guess I'm just worried I can't... I don't know. Act out what I wrote. I have some experience acting. Sort of. But this is so far outside of the norm for me.

  Can you help? Maybe give me a lesson in dirty talk or something?

  Signed,

  Lonely Guy

  It didn't take him long to respond, but I'd still paced across my house in several full laps before he did. When my phone dinged, I knocked it out of my own hands and had to scramble to catch it before it fell to the ground.

  Dear Lonely Guy,

  Breathe. It's going to be okay. Great job getting a hookup so soon. What you're doing is obviously working. You've got the attention of a hot guy who wants to have a little fun. That's what you want, right? You need to remember that. Sex is supposed to be fun. The minute you get inside your own head, it stops being that.

  Do whatever you can to relax beforehand. Take a hot bath -- I'd recommend that anyway, you want to make sure you're incredibly clean. Grindr guys can be picky about that. Listen to some music. Smoke a bowl. Whatever you have to do to feel like you're on an even keel.

  When you get there, don't think. Just do. Dirty talk will come naturally if you just let yourself describe what you want and what you're feeling without inhibition. If you want him to fuck you a certain way, tell him so. If what he's doing makes you feel good, tell him that, too. Don't worry about being filthy. Most guys love it, and it'll probably make your hookup cum like a freight train.

  If it's anonymity you're worried about, make some more rules. Decide what will make you feel like you can be someone else for a night and communicate it.

  Good luck and enjoy yourself.

  - Formerly Lonely Guy

  I reread the email several times, wondering if I was crazy or if it was a lot of vague, general advice that mostly amounted to "don't think too hard," something I was historically bad at. Maybe it was. That didn't make him wrong. I did need to get out of my own head.

  His idea of setting more boundaries held merit. I could say the lights had to be off, even though I wanted to see his body. I could make a rule that neither of us were to talk, but I didn't really want that, either. What I did want was him not to look at my face and wonder if he'd seen me somewhere. He could have a kid at my school, or maybe a sibling depending on his age. God, I hadn't even asked his age. Did it matter? I didn't know.

  What I did know was that I couldn't afford to have my identity compromised. I tried to think of how best to do that and decided right from the start that we weren't going to exchange names or numbers. No personal information at all. I felt a little bad about it, but this wasn't the sort of thing where you exchanged pleasantries. He just wanted to fuck, and so did I.

  The other idea was a little more outlandish, and at first I dismissed it. But, as I searched through my sock drawer for an old bandana and fit it around my lower face, I started to warm to the idea. My partner would really only be able to see my eyes. It meant no kissing, but kissing was what guys who were dating did, right?

  Opening up Grindr again, I selected the message I had with HelpingHands and sent my terms. It was possible he'd shut me down immediately. Some part of me was honestly hoping for that, just so I didn't have to feel this anxiety any longer.

  DorianGay: I've got some terms. I need you to agree before we go through with this.

  He responded almost immediately.

  HelpingHands: What are
the terms?

  DorianGay: No names, numbers, or personal information exchanged.

  HelpingHands: That's pretty standard stuff. I can handle that.

  DorianGay: Also, I want you to wear something to cover your face.

  HelpingHands: ...

  There it was. I'd done it. I'd managed to alienate him already. He was going to ghost me now, and--

  HelpingHands: Like a mask?

  DorianGay: I'll be using a bandana. If you have an old shirt you don't care about, or a shop towel or something. Any of those will work.

  Another long pause. I held my breath as I saw those three dots appear.

  HelpingHands: Alright. No personal info, covered face. Got it.

  HelpingHands: See you tomorrow. I'll be the one who looks like he's about to rob a stagecoach.

  I burst out laughing at that, clapping a hand over my mouth as if anyone would hear me. And, as quickly as that, I had a hookup scheduled with every measure of anonymity I could manage.

  I still felt like I was going to throw up.

  6

  Reuben

  I didn't usually get nervous about hookups, but for some reason, I sure as hell was nervous about this one.

  I did everything in my power not to even think about it until my sister came to pick up David. I wished him a fun time, told him to kill a hundred goblins for me -- something he spent ten minutes patiently explaining was probably capped at about six goblins, considering his character's low level -- then gave my sister a hug and told her to text me if there were any issues.

  I was worried about David. For as much as he loved D&D, this was still a public event with people around, most of whom weren't going to see the game the same way he did. It was almost enough to make me reconsider my hookup altogether and just head down there with them, but I knew me hovering wasn't going to help anything. And, since sitting here with my thumb up my ass wouldn't help my nerves, having my dick up someone else's ass was definitely a good alternative.

  Catching a shower, I tidied up my beard and rubbed aftershave into my cheeks where I'd shorn away the stubble. A couple quick dabs of cologne, then I got dressed in clothing that was casual, but nice enough that I wouldn't look like some random guy coming in off the street. A pearl-snap button down in Gator blue and a pair of blue jeans that were broken in, but not too weathered just yet.

  Grabbing my keys, wallet, and phone, I hopped in my car and headed over to the Holiday Inn DorianGay told me to meet him at.

  I'd stayed at this place once before, when I was doing a conference for work. It was... passable. Not the best hotel in town, by a long shot. Even the big one across the street was worlds better. But it got the job done, and it was definitely enough for a quick hookup. I was even able to stop in at Walgreens beforehand and pick up condoms and lube, just in case.

  He'd sent me the room number about an hour before, and I idly wondered if he'd just waited there the whole time. Images kept running through my mind of all the amateur porn uploads where a guy lays down on a hotel bed completely naked, ass in the air. Another guy comes in, unzips, shoves it in with no lube, ruts like a goddamn animal for a few minutes, dumps his load, then leaves.

  There was some part of my lizard brain that found that a little hot, but the rest of me needed more than that. Even if I knew we were going to be anonymous, even if the connection was only physical one, I needed to have something to grab on to. So I stood outside the room in question, wrapped a Gator bandana around my lower face, and knocked, hoping he wouldn't answer in the nude.

  I heard him padding around on the carpet. I even thought I heard him bump into something on the way over. After a few moments, the latch was pulled back, the door was opened, and I was looking into the eyes of the man who'd asked me here to fuck him senseless.

  Green eyes; a light, mossy color, with speckles of darker greens throughout. His glasses were pristine, sitting high atop the narrow bridge of his nose. His face was soft and round, and I saw an underlying kindness to him I wouldn't necessarily have expected from talking to him on the app. This was the kind of face that, even covered by a god-awful purple zig-zag pattern bandana, was meant to be comforting.

  Giving him a once-over, I took in the slate gray button-down he wore, the straight-leg slacks, the clean tennis shoes that were a little worn through the soles.

  "Thanks for coming," he said, his voice so painfully earnest I couldn't help but smile. He cleared his throat and added, "Though with any luck I'll be thanking you for making me come."

  Okay, that line was awful, but there was something about the way he said it that was endearing enough to keep me from groaning.

  "That's why I'm here," I said, moving past him as he stepped aside to let me in.

  The room beyond consisted of just one bed, a little table, two chairs, and an end stand. I could tell from the rumpled bedspread he'd been sitting on the edge of it for a while. Maybe he had been here for an hour.

  "You want anything to drink? I snuck in some water."

  I chewed at the corner of my cheek, trying not to let my mirth show in my eyes. He was nervous. That much was obvious.

  "I'm good."

  It was pretty obvious I was going to have to make the first move here, which was fine. Stepping up to him, close enough to be in his personal space, I slipped my fingers into his belt loop and tugged him to me.

  I heard him gasp, and my hands went to his shoulders, rubbing firmly before I moved down to his arms. "Relax," I said softly. "Any other boundaries I should know about?"

  "Uh..." He swallowed, and I felt him stand a little taller, his shoulders squared up. He met my eyes. "The only boundary is I want you to fuck me until I tell you to stop. Think you can handle that?"

  I arched a brow, a smirk tugging at my lips. Apparently he found his confidence again. That was more of what I expected, given our interactions on Grindr. I was more than happy to play the role of the aggressive top if he was going to play the demanding bottom.

  "Guess we'll find out," I said, before my hands came around to his plump ass and squeezed, pulling him to me.

  He was semi-hard already and so was I, something I took advantage of, grinding my dick against his, the coarse fabric of my jeans rubbing hard against his sleeker slacks. He whimpered and joined in the motion while I kneaded his ass cheeks, my gaze boring into his.

  I wanted to kiss him, but he'd been the one to ask for the face coverings. It'd been one of his only requests, so I didn’t want to just outright dismiss it.

  “I know you wanted the masks, but… can we compromise? Pulled up a little?”

  I gestured to my mouth and pointedly looked at his. He got the picture quickly and scrambled to lift the cloth. A smile curved my lips as I did the same, leaning closer until our faces were nearly touching; until I could feel his hot breath even through the cloth of his mask. Then I kissed him hard, my lips coming down more firmly on his to account for the barrier between us.

  He moaned, practically melting against me. I parted my lips and kissed him as deeply as I could manage, my hands all over him. All the while I moved us backward, pushing him forward until we were close enough to the bed that I could grab his shoulders and throw him onto it.

  I went right for his pants, undoing the buttons and pulling down the zipper. His cock strained against his boxers, and I rubbed it through the cloth with one hand, the other tugging his shirt up. Finding that soft trail of fuzz I was looking for, I pressed my tongue against his skin and marked a path through the fine hair. I was tempted to rub my face all over it like a cat, just the hint of his soft body making me a little crazy, but I had a more immediate goal in mind.

  Undoing the snap on his boxers, I reached in to free his cock, stroking over it firmly. He gasped, bucking up into my hand, giving me the perfect excuse to lower my head and put my mouth on him.

  He was squirming beneath me, his fingers fisting in my hair. At first, he just let me do what I wanted with him. Pressing my tongue against his flesh, I licked from base to tip,
then focused on his slit before opening my lips just enough to get the head of his cock into my mouth as my lips and tongue moved, caressing the sensitive crown.

  After a few moments, though, the glimpses I'd seen of him started to manifest again. His grip tightened in my hair, enough to send a shock of pain through me that was followed up by a shiver of pleasure. He held me in place that way and thrust up into my mouth.

  I felt the velvety skin of his cock slide past my lips, felt the rigid weight of it in my mouth, tasted his salty precum and worked my tongue around his bare flesh.

  He let out a stuttered moan, his hips bucking involuntarily. I took back some control, my hands pressing down into his thighs to hold him in place. With some effort, I took his dick all the way to the back of my throat. Tears stung my eyes and my gag reflex threatened to ruin it, but I suppressed it and gasped when I pulled back, his cock springing free covered in my saliva.

  "Fuck," he hissed, fingers digging into my hair, pressing against my scalp.

  He urged me back down and I obliged. I might have teased him more, maybe even edged him a little to see how much he could take, but I wanted to get him off. I wanted to feel him pulse inside my mouth; to feel his hot cum hit the back of my throat.

  I sucked the ever-loving hell out of him, at one point using my hand to scooch my mask up just a little bit more. Unburdened by it any longer, I took his dick to the back of my throat, held him there, then pulled back and sucked firmly on the head, my tongue pressing to the underside.