by Skyler Snow
“Is this your surprise, baby? A little plug in your ass, hm?” I pressed against the plug again and Tom made an absolutely sinful noise that was halfway between a moan and a yelp. He gave up on holding his legs up straight and they dropped to the bed before he rolled onto his stomach. Slowly, he lifted his ass and shook it for me.
“Do you like it?” His voice was silken, but I knew he was still trying to keep up his teasing act and slowly losing. I grabbed the gemstone and slowly pulled it out, fascinated by the way that his tight little hole stretched around it until I pulled it out completely. Tom had buried his face in a pillow and his hands were grabbing at the sheets.
He was right. Wearing the plug all day had stretched him out enough that his hole was just barely gaping. He’d taken care of the prep work all on his own today. It usually took half an hour’s worth of fingering to stretch him until he was comfortable. I gently placed the plug on our nightstand and grabbed the bottle of lube from the drawer.
“I love it, baby.” I popped the bottle open and poured the lube into my palm. I couldn’t help but get excited at the thought of pushing into that tight fucking hole and pounding away until he was screaming my name. Tom was a flirt usually but he was absolutely filthy in bed. I stroked myself off, carefully adding more lube just to be safe. There could never be enough lube.
“Can you hurry?” His words were muffled from the pillow and his legs were already starting to shake. I wiped my hand on the bedsheets to get rid of the rest of the lube. Fuck it, he was stretched out and we would need to wash the sheets anyways. I lubed him up instead, making sure things would be easier for him.
“Jack,” he groaned. “Please.”
“Be patient.” I slapped his ass sharply. “Or I’m going to take longer on purpose.”
Tom groaned, but he stopped rushing me. I reached into the nightstand and pulled out a condom. Ripping it open with my teeth I quickly pushed it against my cock and rolled it on. As soon as it was snug and in place, I moved to my knees and positioned myself right behind his ass. I laid another open hand slap across his right cheek and watched as he tried to suppress the urge to jump away.
“Don’t have an attitude with me, baby. You know I’ll pound your hole until you’re dripping with cum, just be patient.” I grabbed his ass, right where a bright red handprint was starting to appear on his pale skin. It got an immediate reaction out of him, the stinging pain and my words. It wasn’t a surprise that he was a sucker for dirty talk, but what did surprise me was that he was an absolute slut for pain.
I gripped the base of my cock and lined myself up with his hole, gently teasing him for a minute. His muffled moans and noises of frustration quickly wore away at my patience. It wasn’t long until I was pressing into his hole, gasping at the feeling.
He was so fucking tight and hot and wet and perfect. Every time we fucked I was left shaking with the effort not to immediately start pounding into him. I was gasping for air as I slowly, slowly slid into him, making sure that every inch fit inside that perfect little fucking hole of his.
“Oh, Jack.” He whined when I was finally fully inside of him. I felt ready to cum already. My grip on his hips was going to leave bruises, but I couldn’t think of that right now. Instead I focused on the way his back arched deep, his ass high as I stood still letting my pulsing cock drown in heat and tight pressure.
“Please, Jack,” he whispered, shaking his ass back and forth. “Please, I need it.”
“Give me a second.” I growled, making Tom whimper and finally sit still.
It took a few seconds for me to get used to how tight and hot he was, but the waves of pleasure lessened and I slowly began to thrust. Tom was shaking under me. I could feel from my grip on his hips and I knew that he was just as desperate as I was to cum. Probably more, since he spent the entire day with that plug in his ass.
“Shit.” I hissed.
The thought of him sitting around, eyeing me with that toy inside of him all day was starting to make me slip and I started to move faster. I always liked to try and take my time, both to make sure that he was safe and to make sure he felt loved, but today felt a little different. The sound of his wet hole stretching around my cock, skin slapping on skin and Tom’s absolutely delicious moans started to fill the room.
“You’re such a slut for me, sitting around on that plug waiting for me to fill you up.” I groaned and brought my hand down on his ass again. He yelped and I felt him clench down around my cock for a second, sending a white hot flash of pleasure over me. “Huh? Am I right? Are you a slut for me?”
“Fuck yes, I’m slut for you Sir!” He shouted, his voice trembling and breathless. His arms had given out on him and his face was buried in the pillow, his ass still in the air like he couldn’t help but want to be fucked. “I’ll be such a good slut for you, Sir. I want to you cum inside of me, pump me full of your—”
His rambling was cut off by another slap and his entire body seemed to spasm for a moment before I heard his muffled screaming just a second before his hole tightened around my cock. He wasn’t capable of words anymore as I pounded into him, desperate to chase my own orgasm.
“God, baby, I’m so fucking close. So close to filling you up like a good little slut.” I wasn’t thinking anymore, just thrusting into him just seconds away from my own release. Tom was making the most perfect strangled noises as I pounded into him and we were both soaked with sweat.
And I still couldn’t get enough. I pulled out, shoving him over until he was on his back. Tom panted, his face flushed.
“I want to hear and see you, baby.” I shoved my cock back inside of him making Tom open his mouth wide, but no sound came out. “That’s it, just like that.”
“You’re gonna make me cum,” he panted. “I’m too close.”
“Be quiet,” I growled against his ear making him shudder. His hands landed on my back, nails digging into my skin. “The only thing I want to hear is you screaming for me.”
“Y-yes, Sir. Yes!” Tom bounced underneath me trying to chase his own orgasm now. “Oh, god.”
The way he moaned always sent me over the edge. I fleetingly thought about the day when we could ditch the condom altogether, but that wasn’t going to be anytime soon. We weren’t even in a committed relationship, not really. Dating, yes. Together? Well, that was a discussion to have at a later time.
All of my thoughts were snatched away as I lifted up to look down at Tom. His pale cheeks were pink now, sweat on his brow and his lips parted as he gazed up at me. This was so much more than sex. When I was with Tom, it was everything I wanted and craved with another person. I wanted him. I was pretty fucking sure I loved him.
Tom reached up a hand, touching my cheek. “Harder,” he moaned, his eyes half closed. “Fuck me as hard as you want, Jack. I want it.”
I leaned down, capturing his lips. My tongue met his as he arched up pressing against my body more. I sucked his bottom lip between my teeth, nipping him as he squirmed.
I fucking loved Tom.
“Fuck!” I doubled over and grinded into him. Tom clung to me, his words snatched as he moaned my name and begged in nonsensical sentences, simply rambling through his pleasure. I knew that he could feel my cock twitching inside of him by the way that he was gasping in that special way that meant that I had brushed against his prostate.
“Oh,” he whined, shaking his head. “Right there!”
Tom’s back arched. He clenched around me so tightly it was almost painful, but I loved it. I felt the wave of pleasure hit me. It seemed to last forever. The wave of lightheaded bliss where I was completely weightless and there was nothing but the rolling waves of pleasure.
Slowly, my vision returned and then the rest of my senses. Tom was panting, his body trembling underneath me. I was careful pulling out, knowing that I had been rougher than I had ever been before and it showed.
I gently touched his red hole and he whimpered. For once I really had lost myself completely in him.
“Do
n’t worry, I’m not gonna hurt you. How was that, baby?” I was still staring at him making sure he was okay. We were both coming down from our highs and Tom usually couldn’t form words until a few minutes afterward.
“Good.” He groaned, a small smile on his lips. There was cum on our bellies from him, but I didn’t care about that right now. What mattered was that I took care of him.
“I’ll bring you some water and a towel, babe. Stay right here.” I patted his leg before hurrying off to the bathroom. From the bedroom, I heard his tired voice.
“You say that like I’m going to be able to walk.”
I laughed. Once I’d gathered up the towel and disposed of the condom I padded back into the bedroom. Carefully, I cleaned him up from the cum and lube. The entire time he simply laid there, staring up at me with those captivating blue eyes.
“What?” I asked softly.
“I love you.” Tom blurted it out so quickly before he threw a hand over his mouth. “Sorry, sorry! We’re not even official yet and I’m doing it again. I’m just shouting out my emotions and my problems and I don’t want to do that to you. Jack, really, you don’t have to answer—”
“I love you too.” I straightened up and pushed the towel aside before I brushed my lips against his. “So much. Tom, let’s make it official. I was thinking about it a lot lately and with you saying this, I think it’s time. What do you think?”
Tom was silent and my stomach started to twist into knots. He sat up and threw his arms around my neck. Tom hugged me tightly before he gasped and plopped back down onto the bed.
“That was a yes, but my ass really hurts,” he frowned. “What’s wrong with you? Why would you be so rough?”
I scoffed before he burst out laughing. “You little smartass. Since it’s like that, let’s go for round two.”
Tom scoffed. “You haven’t got the stuff to go twice old man.”
“Oh? Old man,” I clicked my tongue. “Maybe I’m not ready again just yet, but guess what?” I grinned as he tilted his head at me. “I’ve got plenty of toys just for you.”
Tom squealed and instantly tried to crawl away from me. I grabbed his ankle, tugging him back to me as I laughed. This was my boyfriend. Good thing I loved him.
25
Tom
“This is some good shit, man. Who knew that Scott was such a good looking guy?” I said as I looked through Elliot’s drawings that he’d brought in. They were all digital, which was fine with me. It was easier and probably better practice since all of our work was digital, anyways. Still, I just liked the feel of paper and pencil.
“Don’t say that about my boyfriend. It’s weird.” Elliot said with fake exasperation as I looked through the rest of the folder. It was just random sketches, most of them. Interesting textures and smooth surfaces with light bouncing off of them. All things that we needed to practice for our line of work.
We were staying late in the office. Connie and Issac had taken off a few hours ago now that Isaac had started driving. We were probably the last few in the whole building, except for maybe some late night nerd programmers who did nothing but code and binge energy drinks. Not that I could feel much superior on that note clutching the green and black can in my hand a little tighter. After nights with Jack, I needed the fuel.
The office was quiet, but it wasn’t awkward between us. We had done this already so many times that looking through each other’s drawings was practically second nature at this point. Almost therapeutic. Noting what was good and commenting on what we needed to work on was a cycle. We had learned not to take offense to anything the other said. It was all for each other’s benefit, after all.
From the corner of my eye, I saw Elliot put down a sketchbook and pick up another from the pile. I didn’t think much of it in the moment, but I saw his expression turn puzzled when he opened it up. He leaned forward in his chair to get a better look at whatever was on the pad.
Probably just a picture of a dick.
I turned my attention back to a flower he had drawn. It was evident that he had drawn it in the morning, with the amber glow still lighting up the white petals and the faint veins showing through. It was one of his best drawings yet, and I looked up to tell him when I caught another look at the sketchbook he was holding.
“Is this…Is this my dad?” He asked, holding it up for me to see. Thankfully, it wasn’t anything inappropriate. Just him sitting and drinking coffee with his ankles crossed. Fully clothed. Nothing to suggest anything more than a friendship between the two of us. Still, my heart exploded.
“Give me that!” I lunged at him, dropping the iPad and reaching for the sketchbook in Elliot’s hands. He must have thought I was joking, because he was pushing me away and laughing, holding it up above his head.
“Dude, you drew my dad! You know you could have asked Scott to model you didn’t have to—”
I snatched the sketchbook away from him a little too forcefully and he looked at me, his expression perplexed. My face was burning and anger filled me. Just because I liked to joke didn’t mean I wanted to share this. Not this, not Jack. He was someone I wanted to keep all to myself even if only for a little while longer. I clutched the book to my chest as my friend peered at me carefully.
I’m being irrational.
It wasn’t like he meant anything by his teasing and it wasn’t even like he was invading my privacy. I had handed those sketchbooks over for him to snoop through. I just hadn’t checked them all as thoroughly as I thought I had. He was trying to catch a glimpse of my face but I turned away from him. I shoved the sketchbook into my bag before shoving it under my work desk.
“Tom? Is… everything alright?” He asked. I could hear the concern but mixed in with suspicion. My mind raced. Years of recreational lying had given me an edge and I was quick to answer.
“Yeah, it’s just private. Jack and I have been talking a lot, like you asked, and he lets me draw him from time to time.” I shrugged, “He says maybe drawing him would help me understand him a little bit more.” I said quickly. It wasn’t my best lie and it didn’t really make sense, but it sounded like something he would say and this entire situation was just about weird enough for it to sound reasonable. Elliot was quiet for a moment before picking up another sketchbook and looking through it. The silence only lasted for a few moments, though.
“How is he?” Elliot asked. He didn’t sound convinced, but from what he knew, our relationship was already strange. Jack and I had gone from best friends to lovers to partners. He still didn’t know the extent of our relationship, but he knew that we were close and we spent most of our free time together now. He hadn’t questioned it yet, but I could feel his curiosity starting to get the better of him sometimes.
“Oh, he’s a lot better now that he’s got you and Scott around all the time. You two do him a lot of good.” I tried to steer the conversation away from me and Jack and hopefully onto something a little safer. Elliot glanced up at me from the sketchbook in his hand.
I instinctively looked away, back down to the discarded iPad I had dropped on the ground. Scooping it up I acted as normal as I could. I opened up another file and started to look over a sketch of a little dog covered in hardened mud.
“But what about you? Like, you talk to him more than Scott and I do, and about important stuff. Is he alright?” Elliot asked.
I thought for a moment. Jack spent almost as much time with me as he did with Elliot and Scott combined, but he didn’t know that. Most of our time spent together was sleeping at each other’s homes. But he was right. I was who Jack trusted with his secrets and I could probably gauge his mental health better than Scott could at this point.
“Some days are better than others. But his good days outnumber his bad ones,” I couldn’t help being satisfied by the fact I was part of the reason for that. “I think L.A. was a good move for him. He’s happier now than he was at the beginning.” I was still vague, not knowing how much to share. What would keep my relationship a secret while re
assuring Elliot that everything was fine? I wasn’t ready to tell him or anyone about what we were.
Not yet.
“Are you sure? It kind of seems like he’s maybe been a little distant from us lately. Scott’s been noticing that he doesn’t really ask to visit as much as he did, and we’re just,” Elliot glanced away before he looked back at me. “We’re worried.” I winced at how real the hurt in Elliot’s voice was. Was Jack being distant? I didn’t want that. I almost told him the truth, right then and there, to reassure him that his father wasn’t angry or ignoring the two of them. Or that he wasn’t lonely and still struggling to find his way. He had me and I had him. Jack was loved more than they knew.
“It’s just work, that’s all,” I whispered. “Next time I see him, I’ll tell him to drop by more often.”
Elliot nodded and I felt horrible. He was one of my closest friends. Was I being a completely selfish asshole? I couldn’t look at him anymore as we began to pack up and head home. Something had to change.
Maybe it was time to welcome Elliot and Scott into me and Jack. Fuck I hoped my friend was happy for me, because I didn’t think I could give Jack up.
I ignored the voice that whispered Jack may give me up for Elliot.
26
Jack
“Really, babe, I think we have to tell him. He’s starting to get worried about you. Elliot thinks that us hanging out is just me and you talking about things, like you’re hurt and need a shoulder to cry on or some shit.”
“And?” I asked, knowing that he wasn’t done talking.
Tom collapsed on the couch clearly he was done with his pacing. I could see his agitation still though. He was frustrated at the situation, but he was also worried about something. “And I don’t want him worrying when there’s nothing to worry about.”
“I know.” I took his hand and he easily curled up against my chest after I sat beside him. It was a familiar thing now, something that we did whenever Tom was upset. He would curl up against me and I would hold him until he calmed down. “We can tell him.”