Role Play

by Alison Hendricks

  He let out a shuddering breath, his eyes so dark they almost couldn't be called green anymore.

  "I want to," he said, voice shaking, "you'll just have to be patient with me."

  I jerked my head toward the hall. "Better to do this on a bed."

  As I led him toward his own bedroom, I shucked off the rest of my clothes and Elliot did the same. My dick was painfully hard and dripping, so much so that I had to give myself a hard squeeze. Otherwise I was going to shoot as soon as he pushed inside of me. I could already feel my body reacting to it, my cheeks clenching, my hole begging to be filled.

  Grabbing the lube from his nightstand, I was generous in spreading it. Elliot reached for the condoms and a shiver raced through me as I heard him tear the package open. I handed him the lube and got onto the bed on my stomach, sticking a pillow underneath to raise my ass up comfortably. The sound of him slicking lube all over his dick made my thighs tremble in anticipation, and I bit my lip to stop the moan that tried to escape.

  "I don't want to hurt you," he said as I felt his weight on the bed behind me, his hand soon resting on my back.

  I wanted to tell him he wouldn't. I was beyond pain right now; in that place where I craved pleasure in the roughest way possible.

  Instead, I said, "Just go slow at first."

  That wasn't what I wanted. I wanted him to just slam into me right now, until his cock was buried deep in my ass and his balls slapped against my skin. That would hurt, and I knew that desire had everything to do with my state of mind. I'd regret it tomorrow when I was trying to do my job around the ache caused by every movement.

  Elliot positioned himself behind me and I held my breath as I felt the tip of the condom brush against my cheeks. He moved closer and this time it wasn't latex but the solid warmth of him that I felt sliding between my cheeks. He rubbed himself along my crack, smearing lube between us. I wiggled my ass and pushed back against him, feeling needier than I'd ever been.

  When I finally felt the head of his dick breach my hole I cried out. Elliot mistook it for pain and stopped, but I pressed my ass toward him, taking him deeper all on my own.

  Even still, he was slow at first just like I'd told him to be. He sank into me by half-inches, every centimeter feeling an eternity away.

  "More," I pleaded, arching my back, positioning myself in a way that was unmistakable. "I'm good. There's enough lube. Just fuck me. Please."

  I couldn't even be bothered to care how I sounded while begging. I needed this too much.

  When Elliot started to move in earnest, I got my wish. Part of it, anyway. He sank the rest of the way into me, drawing a groan from deep in my throat as I felt his body flush with mine. There was little resistance as he drew back, just my body clinging to his, holding tight around his dick, begging him not to withdraw.

  He didn't, thank fuck. He just built momentum, fucking me with more confident strokes. Every drag against my prostate sent a blinding burst of stars behind my eyes, turning my muscles into jelly as I just submitted myself to him, begging even more.

  "Harder. Fuck yes, I need it."

  He was panting, and when he slammed into me there was a sound in the back of his throat that was almost a growl. My balls tightened suddenly and I came close to coming right then and there, but I managed to hold on and savor Elliot leaning over me, fucking me into the mattress, the headboard hitting the wall over and over.

  When he changed his angle, more of his thick cock rubbing against that sweet spot inside of me, I couldn't take it anymore. My hand flew to my own cock and I stroked wildly, my body seizing as I came with a loud cry of pleasure. My ass clenched around his dick, my body begging him to come.

  His hips slammed forward one last time and he let out a moan that shook through me, lighting up every good feeling I could possibly have. I felt his cock jerk and pulse inside of me, felt the warmth of his cum as it pooled inside the condom.

  And I felt the loss when he withdrew to dispose of the condom. That was always the worst part of being fucked. The emptiness afterward. The bed that grew steadily colder. It was why I didn't bottom very often. I needed the connection more than anything, but I didn't want to need it.

  I heard Elliot draw near again, felt the shift of the bed. He leaned over me and pressed a soft kiss to my back, just between my shoulder blades.

  "You wanna talk about it?" he asked in a low, soothing voice.

  The kind of voice I wanted to comfort me as I talked about all this helplessness I'd kept buried deep inside.

  "Not really."

  It wasn't a lie. I didn't want to talk about it. I wanted to just... get over it. I'd hoped a quick and dirty fuck would help, but it hadn't. No matter how good it'd felt, no matter how much it scratched that itch, it ultimately didn't change things.

  Turning over, I lay on my back, my breathing slowly returning to normal. Elliot sat beside me, a sort of half-tension in his body. He wanted to ask me more; wanted to pry it out of me. I was glad he'd so far managed to keep those wants under control. Things wouldn't go well for us if he couldn't.

  "Hey, uh. This is probably a weird time to ask, but do you wanna get something to eat?"

  I turned to look at him and blinked. "How is it weird? I'm fucking starving."

  A renewed energy coursed through me as I pushed myself off the bed. I padded out into the hall, snatched my boxer briefs from the floor, and tugged them on.

  "What do you want?" I asked, rummaging through the drawer in the hall where I knew he kept takeout menus. "I could go for some barbecue. Fuck, a slab of ribs sounds amazing right now."

  I heard him walk up behind me and out of the corner of my eye I saw he'd pulled on his boxers and his pants, the zipper definitely broken on them. He'd done up the button, at least, but the fly was perpetually open.

  "Actually, I was hoping we could go out to eat."

  "Even better. All you can eat ribs," I said with a grin. "Let me just get a shower and--"

  "Date!" he exclaimed, blurting out that single word. It was followed by him stammering out several others. "I'm... I want... date. I want to go on a date. With you."

  For a long time, I just stared at him. My heart was hammering in my chest, my ears were ringing, and I couldn't remember how to form words.

  Way more worrisome was the fact that all of that wasn't because what he said scared me. It should. I didn't want anything serious, and dating crossed that line. Dating meant there was a chance for more. Dating was the attempt of both parties to see if there was a viable future.

  I didn't want that. Except... some part of me found the idea of going out with Elliot, of being seen with him really damn appealing. All the dumb, romantic boyfriend shit I told myself I'd never do again.

  The fact that I wanted it scared me a hell of a lot more than him asking. There was an urge in me to just cut my losses and run, but that urge was met with one just as strong telling me to stay and tie myself to this man even further.

  "I'm... not looking for anything like that, Elliot," I finally managed, turning to look at him fully. "I thought you knew."

  "Yeah, no. Of course." He looked everywhere but at me, hand moving to the side of his neck. "Temporary insanity on my part. It would be a terrible idea either way. I'm... well, I'm not teaching your nephew, but something close enough that it would probably raise questions."

  He was doing that thing where he rambled until he was out of breath. I wanted to reassure him. I wanted to take him into my arms and kiss him until he felt safe and cared for.

  Instead I pulled out the menu for a local barbecue place, then dug my phone out of my pants. "Why don't we just order some food, find something to watch, and enjoy the rest of our night?"

  He nodded and I passed over the menu so he could choose what he wanted. An hour later we were eating messy food atop barely adequate TV trays, a Netflix show playing that neither of us were really paying attention to.

  The underlying awkwardness didn't go away, but neither of us brought it up. At the end of th
e night, I thanked him for being there, then I got into my van and drove away, ignoring the urge to turn back around.

  17

  Elliot

  I was never one to put too much stock into "mixed messages." Usually it just meant a lack of communication skills on the part of everyone involved, and probably a willful ignorance for the one who was trying to sort through what they considered to be an ambiguous message.

  But what I got from Reuben over the next couple weeks definitely counted as mixed messages.

  I knew better than to push the dating thing. He'd been clear and I wanted to respect that, no matter how much I would have enjoyed having more. It wasn't like I was going to turn down his requests to come over, even outside of me teaching him. I craved Reuben in a way I'd never craved anything, and the instant his hands were on me again I felt like I was finally alive.

  I'd learned what he liked and he'd learned what I liked, so whenever we came together it was an explosion of force and pleasure, racing toward that mutual edge. It was scorching hot, every time, and in a way I thought someone like me would never achieve.

  I hadn't exactly been adventurous in sex before. Pegging was as far as I'd gone, and even that was low intensity. Reuben opened my eyes to a whole other side of myself. One that could whimper and beg to be stretched and filled and fucked, and one that could be the one rutting like a wild animal, spurred on by the needy cries of the man beneath me.

  All of that made sense. That was what Reuben wanted, and I wanted it, too. What happened after that always threw me off balance. Sometimes we'd go back to D&D. Other times we'd get dinner and stay up late talking. Or we'd curl up on the couch with the TV on and I'd fall asleep, finding my head resting against Reuben's shoulder and his arm around me when I woke.

  It was... boyfriend stuff. At least that's what it felt like when he was spending more time at my place after work than he was at his own. Especially on those days when I could tell he was upset. It felt like he really wanted someone to just be with him, and that someone was me.

  I knew I couldn't talk to Keith about it. He'd tell me I was reading too much into the situation and I needed to just be happy with what I had. Tina was a romantic, so she'd probably assume Reuben wanted more but just didn't know how to ask. Neither of those answers really fit, and I found myself scrolling through my phone late at night, not even sure what I was searching for.

  Reuben had left about an hour earlier, after lying in bed with me, very much conscious this time as his leg and arm draped over me.

  As I tried to think of a question to even type in, I remembered the last time I'd been in this predicament. Different circumstances then, but the advice had given me the confidence I needed to be with someone like Reuben.

  Maybe Formerly Lonely Guy would have some advice for me. Not a blueprint for me to follow that turned me into someone I wasn't -- I wasn't interested in deceiving Reuben. At all. I just wanted to better understand the situation.

  So I opened up the email, and after about an hour of fussing with it, I finally came up with something that would serve its purpose decently enough.

  Formerly Lonely Guy,

  I wanted to thank you for your advice before. It was helpful, though I ultimately decided "pretending" wasn't for me. It did help me with some confidence issues, though, so I definitely appreciate it.

  I need advice with something a little more... delicate now. Your ad says you deal with all types of relationships, not just sexual ones. So... this is probably going to be weird to see, but the guy I met through Grindr turned out to be great. We get along really well, sex is amazing, and he's a good guy I'd like to know better.

  He says he just wants to do the casual thing. Friends with benefits, or something close to it. I want more, but I'm not going to push him. Or I wasn't. Lately he's been doing things that seem a lot more significant than "friends with benefits" and I don't know what to think.

  We spend a lot of time together. I've been helping him with something he's doing for his nephew, but we're also eating meals together, watching movies, falling asleep on the couch... just general things that seem to suggest he might want more but is afraid to have it.

  Am I crazy? Maybe I'm just seeing what I want to see. Like I said before, I'm not experienced with anything, really. The last time I dated anyone was in college, and that person became my wife. I'd also say I've never had a really close male friendship, so maybe this is just the way things are.

  Any advice you can give would be immensely helpful.

  Signed,

  Confused, But Hopeful

  It didn't take him long to respond. I was just about to finally give sleep a chance when he messaged me back.

  Dear Confused, But Hopeful,

  Without more context, it's hard for me to know if this behavior is that of a friend, or someone who wants to be more. I want to continue giving you hope, but it's possible your guy just has really close friendships. Can you tell me anything more about the situation?

  You can't force him into something more than what he wants. He needs to be willing, and he needs to want you as more than just a friend. He also needs to have the desire to let go of whatever fear he's holding on to, if it is fear stopping him.

  That said, you can make yourself more appealing as a partner. You've spent enough time with him to know what he likes. Do more of that and less of anything that gets under his skin. Do nice, considerate things for him -- don't let anyone tell you guys don't like it when they're made to feel special.

  Test the boundaries of these encounters you've described. Act like you would if he was your boyfriend. When you're having sex, let yourself respond as if it's about more than just physical release. If he starts to reciprocate, you'll know there's a chance. If not, you've just saved yourself years of pining, my friend.

  Signed,

  Formerly Lonely Guy

  I considered his words for a good fifteen minutes, reading and re-reading what he'd written. There was wisdom in it. I didn't agree with everything he said, but there were some good points. I could be caring and considerate; make him feel like he matters to me. That wasn't going to be anything different from what I'd normally do, it just might have more purpose behind it.

  As for testing boundaries, I didn't think I could stop myself from doing that. I was catching some kind of feelings for Reuben, whether it was convenient to do so or not. And I'd never been the type of person who could just endlessly bottle those things up. They were going to come out as we spent more and more time together. Especially as we explored new levels of intimacy.

  I didn't want him to feel pressured, but either I denied my own affection for him and played at being something I wasn't again, or I broke things off completely because I just couldn't do casual. Neither of those options were things I wanted to entertain, so maybe Formerly Lonely Guy's advice was a viable alternative.

  Writing back, I explained a little more about Reuben without giving too much away. The world was a small place and there was a chance they knew each other, which meant I needed to be careful about what I said. Otherwise I could put Reuben and his nephew in harm's way, and that was the last thing I wanted to do.

  I just... wanted to know him. The real Reuben, beneath the little smirks and the smoldering looks. I wanted to know what had made him so obviously upset that one day, and I wanted to help him overcome it. I wanted to be the person he turned to, the shoulder he cried on. I wanted him to want me as more than just a casual companion to pal around with.

  It was ridiculous, and some part of me already knew it wasn't going to end up as some fairy tale where we lived happily ever after. Even so, I couldn't stop myself from hoping and, as I drifted off to sleep, I clung to the dream that maybe one day we could be something more.

  18

  Reuben

  Spending more time with Elliot was definitely good for my mental health.

  It didn't erase the fact that guys like Ty were being forced to play at high risk of permanent injury. It didn't help when Da
vid was in the middle of a meltdown and I was tearing my hair out trying to decide what to do. But, I found a sort of calm in between all the stress, and that wasn't something I'd really been able to reach for a while.

  There was a time I might have gotten it from going out for a run. That time was over now, though. My mind always veered into twenty different directions, none of them all that good for me. With Elliot, it was different. Even when we were just hanging out, watching TV or something, I was able to shut all of that out and just enjoy the moment.

  Part of me wanted to make that mean more than it did, but I knew better than to go down that road. The fact that he'd asked for a date already meant I needed to tread carefully. I didn't want him to feel like I was leading him on. I just couldn't get into a relationship with him. There was too much going on, I had too much baggage, it was all just... too much.

  What I could do was show my appreciation by inviting him to a Gator game. We'd talked a little off and on about my job and football in general. He'd gone to a few games as a kid and knew the rules of the sport enough to follow it, but he'd fallen out of the habit of watching NCAA or NFL ball in recent years. His agreement to go with me made me happier than it should have, though, and I reminded myself I needed to calm the fuck down so I didn't give the impression that I wanted this to be anything more than two guys enjoying a football game.

  My tickets were... pretty shit, to be honest. Alumni with deep pockets always snapped up the best tickets, then high-level administration, former players, and finally the rest of us who were even remotely affiliated with the team. As I led Elliot down the beer-stained stairs of The Swamp, he commented on it.

  "I don't know why I thought you wouldn't be stuck up here with the rest of us plebes."

  I laughed at that, lifting my ticket against the blazing Florida sun to double check the row. "Honestly, we made out pretty good." I gestured down to the row at the very bottom of this section. "We're right in front of the bars. Easier to see, and a lot easier to take pictures."