The Equipment Manager S01E06 – Part 1

It was time.

The process had gone slowly, gradually moving up to larger and larger plugs, and I was starting to wonder if I’d ever finally graduate to that last, largest one. Days went by, a couple weeks, and I knew the guys were growing impatient.

After Sammy, there were no more texts, no calls to come over, no encounters in the locker room, and I was starting to think that maybe, just maybe, this was all over. I’ll admit, I was more than a little disappointed. I was starting to get used to this new life and new identity of mine, but maybe it was just not meant to be.

When I finally got the last plug in, I felt a quick little twinge of excitement at the base of my stomach; a little spark of hope that this might work. As soon as it was in and my ass had settled around it, I texted Avery.

*Hey. Just put the last one in… you know… if you’re still interested.*

He replied almost right away.

*How long?*

It couldn’t be that day; I still wasn’t quite ready yet.

*Soon. A few days at most*, I texted back. He didn’t say anything for a few minutes, and I started to worry, until my phone vibrated.

*Friday.*

*****

The week dragged on. Oddly, looking back at the time, it suddenly seemed like the entire process had gone by rather quickly, and that now the anticipation of the first time was what dragged. All I could think about was Friday evening, of Avery, of the first time. Would he feel like the plug did? If not, better or worse? What was he like in bed? How did he like it? Hard, gentle? Was he as excited for this as I was?

I’ll spare you the agony that was the next few days. There’s no point in re-living the tension and the nerves. Besides, nothing really happened during that time. Practice was normal. All four guys I had been with so far; Thomas, Avery, Nathan, and Sammy, said nothing, acted no differently. I had expected… something, at least, and not necessarily from them, but maybe someone wanting a blowjob or a quick handy. Nothing, though. Not until Friday.

Practice let out more or less on time, but Avery was nowhere to be seen. We had worked out a plan earlier that week where I would say that there was a party (no, of course no alcohol, Mom) and I had been invited, which… wasn’t exactly, entirely a lie. Then, after practice, he and I would meet up, go to his house, and… do our thing. The only problem was that I couldn’t find him.

I checked the locker room, the showers, equipment room, nothing. I was beginning to think I’d been ditched, Avery had changed his mind. Maybe it had just taken me too long, maybe all of them had given up.

I was halfway to my car when I heard tires crunching on the pavement behind me. “Hey, you comin’ or what?” I stopped in my tracks and spun, the grin already forming on my lips.

“I was starting to think you had changed your mind,” I admitted, taking a couple steps toward the car.

“Nah, had to talk to Coach about some strategy stuff, nothing important.” Avery sucked in a breath, clearly buying himself some time. Was he nervous? I sure as hell was. “So, you want to go then?” I only nodded, then came closer to the car when I heard the doors unlock.

I had expected the ride to Avery’s house to be fairly quiet, even silent, and entirely awkward. The last time I’d sat in this seat, I had turned down a handjob, asking for time to get used to the idea of this new adventure. Now, there was no awkwardness, and also not handjobs. Instead we talked, about the team, about life, about whatever came to mind. I learned about Avery’s girlfriend, Cassie. With a quick pang of guilt, I asked if she knew about me, and about the fact that Avery had been with others. He sort of chuckled, then said that she not only knew, and didn’t really care, but that occasionally she had watched. Well then… We only stopped talking when we pulled into his driveway, when I think the nerves kicked in again, for both of us.

Avery’s house was large, but not exactly showy. There were three floors: two above ground plus a finished basement. “My parents are home, but they go to bed early. They’re upstairs, and my bedroom is in the basement, so we’re good.”

“No way they can hear, or might just come down for whatever reason?” I asked, not really wanting to get caught.

“Nah. They never go in the basement. It’s almost like my own apartment, really. It’s pretty nice.” And it was pretty nice. The setup was similar to Nathan’s in several ways: couch, TV, his own bathroom. The space was larger, and arranged differently, but close enough. I took a seat on the couch and Avery turned on the TV, sitting next to me, but not too close.

The nerves started again, now louder than ever. I turned to him. “Look I uh…” Avery cut me off.

“We don’t need to talk about it, OK? Just relax, it’ll happen, just not out here.” I glanced over his shoulder toward his bedroom door. “Yeah, in there, on a bed, like normal people.” I nodded. Somehow, doing it on his bed felt less… dirty. I settled back into my seat and tried to watch TV.

I think we sat next to each other for about a half hour, although it seemed longer. Neither of us said anything the whole time, until Avery spoke up. “Why don’t you go lie down now?” he suggested. “Take everything off, get under the covers if you want. I’ll be in in a minute.” My stomach dropped, but I nodded. As I stood, he grabbed my hand. “It’ll be alright, OK?”

*****

Once in Avery’s room, I shut the door behind me, taking it all in. The room was dark, shadowy, lit only by a small lamp in a corner, giving a sense of closeness and intimacy. The head of the bed was against the right wall, with a dresser just to my right. It was clean, tidy, comfortable. All in all, not a bad place for my first time.

I took in a breath, deep, long, then slowly let it out. I knew Avery was going to give me time, but eventually he’d want to come in, and I didn’t really want to be standing just inside the door, half-dressed when he did. I undressed. There was no show to it, no tease, because there was no need. Without an audience, stripping was nothing more than a thing I was doing. I folded my clothes as neatly as I could and set them in a bare spot on top of the dresser, then slipped under the covers.

I only had to wait another minute or so for Avery. He opened the door, stepped in, then shut it, all without a word. His shirt came off first, quickly, in a single motion, baring his shoulders, his chest, his abdomen. I watched the muscles move and flex beneath smooth skin. His pants were next, without ceremony, dropped around his ankles. All that remained was a pair of bikini briefs, cupped around his manhood and just barely giving a hint at the shapes it concealed. I could make out the lines of his cock, the curve of the head, and I felt my mouth watering. I hadn’t taken Avery yet, not in any way other than in my hand. Tonight I would feel him inside me.

The briefs came off finally, again without any real show, then he came to the bed, cock and balls wobbling back and forth in the dim light. I moved to the side, giving him room, then listened to the rustle of the sheets as he lay next to me. My heart was pounding, my breath shallow. “You OK?” Avery asked, and I nodded slowly. “Touch me,” he instructed softly. “Just… here…” He took my hand and placed it on his hip. “Don’t move it, just get used to the idea of touching me.” I nodded.

His skin was smooth, warm, soft. I liked the way he felt against my fingertips, and without thinking, I gently squeezed. That made him smile. “I’m um… kind of nervous,” I admitted quietly.

“I know, but there’s no reason to be, alright? We’ll go slow, and if you’re not ready, it’s not a problem.” God he was so good to me that first time.

“No… no I’m ready, I want to. Just, slow, alright? It’s my first time.”

Avery nodded. It wasn’t my first time with another man, but I hadn’t had actual sex with the others, with the exception of Sammy, and even then I was… pitching.

Avery’s hand suddenly appeared on my hip, gently caressing, occasionally squeezing. “Do you want me to lead? I’m fine if you want to,” he offered, and as I thought about it, I realized that I had no clue how and where to begin, what he would want, how he would like it. I finally shook my head.

“No, you do it. Tell me what to do, show me.” My voice was little more than a whisper, but Avery heard. His fingertips danced over my hip for a moment, then moved toward the middle.

“Do you remember what we did the first time? We can start there, if you want.” I nodded. I wanted. “OK, that works then.” His fingers played across my bare skin until they found their target. I wasn’t hard yet, but felt my cock twitch at his touch. His fingers ran up and down my length, on the side, beneath, before he cupped my balls gently.

My own hand took a similar path on his body, my fingertips finding the base of his shaft. I had been wondering if I would remember the feel of his dick, remember the contours and shapes. It turned out that I did, at least some. Over time I would get familiar with his cock, and those of many of the other players, but for now, this was my first sense of recognition when touching one other than mine.

Avery’s member hung to his side, draped over his thigh. I gently stroked up and down the length, taking in the warmth of him, focused on the tiny sensations in my fingertips as they explored. I almost didn’t even feel him touching me, at least not until I felt his hand wrap itself around my shaft and begin stroking. I had apparently become erect without really noticing, but now that I was, Avery took to pleasuring me just as we had before.

“I want more than a handjob from you this time,” I whispered, looking up to his eyes for the first time.

“I know,” he said with a nod, but didn’t stop what he was doing. It wasn’t long before he started to harden as well, and my own hand wrapped around his thicker shaft. We stroked each other like that, slowly, carefully, for several minutes, our hands occasionally exploring elsewhere: cupping balls, caressing butts, stroking thighs. At one point I ran my fingers over his abs, then back down.

We had each found a rhythm to keep the other hard, without taking it too far, just keeping the other erect and feeling good, but that wasn’t going to be enough, for either of us. I stopped stroking, holding his dick at the base. “Avery, let me go down on you this time?” His hand stopped, but he didn’t move, like he was considering. He nodded though, and I release his member, allowing him to roll onto his back, still under the blanket. This, at least, I was a little more familiar with, knew how to get going. I slipped under the covers, turning to him, touching his leg to find what I wanted in the pitch blackness.

Suddenly the covers were thrown back. I could see, and could be seen. For the first time that night we were each fully exposed to the other, and I felt his eyes on me. “I like to watch,” came a soft voice. I grinned at him and nodded, then leaned in to plant a gentle kiss just next to his hard cock.

“So I should give you a show then? Something to look at?” This time he nodded, and I knew it was time to get to work.

I gave another kiss in the same spot, my lips gently touching smooth skin. Whatever he used to shave or wax or whatever, it left him perfectly, immaculately hairless, without even a hint of stubble. I had to ask what it was at some point. For now, I slid my tongue around the base, tasting him, feeling him. I moved lower, kissing and licking his ball sack, feeling his large testicles just beneath the surface. I pulled one into my mouth and gently sucked. I heard Avery sigh, and damn if I wasn’t just a little proud of myself. After a minute I moved to the other one, gently sucking and licking, caressing it with my mouth. All the while I could feel his cock next to me, occasionally touching me but always looming over, waiting.

I didn’t hesitate when it came time to take Avery’s cock in my mouth. I had had enough of them that I wasn’t intimidated anymore, but certainly not enough to be a master. I struggled to fit as much of him as I could, and while he wasn’t as large as Nathan, Avery was still sizeable. I got less than half way, and had to grip the rest with my hand.

My tongue traced every line, every ridge of Avery’s cock. I poked at the little hole in the tip, then slathered my tongue over and around the head. I took him as far down as I could, then slipped my tongue out to get just that little bit more. This was the cock that I had wanted since I first saw it, first felt it, and now it was mine. I wasn’t going to waste the opportunity.

I quite literally fucked Avery with my mouth, bobbing up and down, sucking hard, swirling my tongue. All the while, moans escaped from him, and even more as I cupped his balls. This was the part I knew, the part I was good at, and I let it show.

Occasionally I’d let his dick out of my mouth, so that I could kiss and lick and suck down either side. Sometimes I’d tease, nibbling around the base or licking up his abs, then back down. I always wound up with his cock back in my mouth though, sucking and slobbering down the shaft. I realized that, while Nathan was bigger, Avery’s dick was, so far at least, my favorite. Something about the shape, the size, it was just perfect, and I was becoming more and more determined that I would be able to deepthroat him by the end of the season.

My thoughts of sucking him all the way down were interrupted by a gentle touch to my head. I looked up, mouth still full. Avery was watching, as he said. “I think it’s time,” he said. I bobbed down and back up once, then let his cock go with a little kiss to the tip. “Are you ready?” he asked in a way that suggested that “no” would be alright. I just nodded again. “Stay like that.” I had been on my hands and knees already, ass in the air, perfectly positioned to be taken from behind. I kind of appreciated that he wasn’t making me move.

I watched as Avery crawled across the bed, and as he lubed his cock. When he approached me, I hung my head, tried to control my breathing, and reminded myself to relax.

“It might still hurt,” Avery warned, “but I think you probably stretched as much as you could for now. Are you ready?” I nodded. “Alright.” His hands went to my hips and held me firmly. I didn’t intend to move, to pull back or anything, but it was probably better that he held on just in case. Then I felt him. I felt it. Avery was just barely pushing the head of his cock against my ass, pressing it between my cheeks. I sucked in a breath of excitement, but made no other noise, not until he found my opening. As he pressed against my asshole, I groaned. He didn’t warn me, probably worried that I would tense up. Instead, his hips simply rocked forward a little, and the head of his cock pushed into me.

I was ready for pain, expecting it, but it never came. There was pressure, stretching, but it didn’t hurt. “You good?” Avery asked, now holding perfectly still. I had no words and just nodded. “OK, I’m going to give you some more then.” His grip firmed up and I gasped as a few inches of his hard cock slipped into me. “Alright, let’s stop there for a mi…”

“More,” I demanded. “All of it.” Avery hesitated.

“I don’t want to hurt you,” he argued.

“It doesn’t hurt goddamn it. Put it all in me, Avery.” I wasn’t lying. There was no pain, not really. I had taken the time to prepare for this, for him, so that when the moment came it would be a good one. It worked.

I could feel him hesitantly pressing forward, apparently not fully believing me when I said that it didn’t hurt. Still, I felt every inch of him as it entered my body, until his hips pressed against my ass and our balls touched. Avery groaned a little once he was all the way in.

“You can start,” I told him, “just not too fast.” There was no verbal reply, but his hand gripped me tighter for a moment, before he started to move.

The strokes were slow and careful, but each time he pulled almost all the way out, then slid his whole length back in. I had never experienced such a feeling of fullness. The sensations sent tingling little sparks up my spine and down my legs, and I knew that this, this act of sex between two men, was my thing, or one of my things at least. I knew that I would always want this, and that I would always have men as lovers.

Again my thoughts were interrupted by Avery as he, apparently now satisfied that I could hold myself in place, slid around my hip to the base of my shaft. He started stroking me at the same pace he was fucking me. When he pulled out, his hand slid to the tip. When he pushed back in, it moved to the base, so that after a little bit, the sensations kind of muddled and it almost felt like my own cock in my own ass. I know that I groaned his name several times as he did that.

Eventually the pace picked up and I could tell that neither of us was going to last very long. I felt the tension in my balls, and heard the quickening of Avery’s breath. I wanted to cum with him, together.

“Avery… “ I said, panting a little, “I’m going to cum… I want you to cum in me, alright?” There was no answer, not directly, but he did grip me a little tighter for a second, maybe an acknowledging squeeze. That set me off. I moaned loudly and immediately began covering his sheet in cum. At the same time, I felt his cock throbbing in my ass, and knew that he was unloading into me. My ass gripped him, held him tightly, even milked him for more, all while I was lost in a drug-like high of orgasm. Avery stopped moving, fully inside me, while we finished pumping hot cum.

We stayed like that for a little bit, until Avery softened enough that my ass could squeeze him out. His dick flopped limply, making a smacking sound as it slapped against his thigh. I grinned at the noise, before carefully lowering myself to the bed.

“You OK?” Avery asked before he moved. I nodded, still not really wanting to speak yet. He seemed to get that, taking my nod for his answer, then lying next to me, both on our backs, bodies touching here and there.

After a while, I turned toward him, lying on my side, my hand resting on his abs, fingers gently exploring. “I’m glad it was you,” I admitted. They were the first words I had said in a while. “I just, like I don’t want it to get weird or anything, just, you know, you’ve been really nice to me and everything. Honestly, this whole experience hasn’t been anything like I thought it would be.”

“How is that,” Avery asked. “And it’s not weird.”

I grinned at the second part, then gently kissed his chest. “Just… you guys have all been really like… cool about this. I mean, it didn’t start well exactly. Like, I was kind of blackmailed into starting this, but then you were all… good to me?”

Avery turned to me, his hand resting on my hip. “We like you. I like you. I think this is a good arrangement for all of us.” He kissed me then, on the lips, softly, then with a little more energy. I let him, I welcomed his tongue when he offered it, and let my hand slide around to his butt, squeezing the firm muscle tightly.

“So do I ever get a piece of this ass?” I asked playfully, squeezing again.

“Oh, I’m sure you will,” Avery said with a grin, before we both fell silent for several more minutes.

“This is nice,” I said, breaking off the most recent kiss. We had been silent for a while, but that didn’t mean our mouths weren’t busy. “I really don’t want to leave.”

“So don’t,” Avery replied with a verbal shrug.

“I can’t. I told my mom I’d be home.”

Avery nodded, understanding. “When do you have to be back?”

“No… specific time just… before midnight I guess?”

Avery grinned broadly. “That’s plenty of time.”

“For what?” I asked with a teasing grin.

“For this.” He moved toward me, pushing me onto my back, his lips on mine, his hand moving to my cock.

To be continued…

Source: reddit.com/r/Erotica/comments/qgesn6/the_equipment_manager_s01e06_part_1