Chapter 37

Penguin lay on his stomach on his bed, that Tuesday, looking at the items that he had sprawled out on his pillow. As his eyes ran over the lube, condoms, and butt plugs, he forced himself to think about it.

Sex. But real sex. All-the-way sex. Sure, he counted the things he'd already done with Killer as sex too, but it was still different. Penguin had assumed they would go all the way at some point, he had hoped they would, but he never really thought about it. Let alone that they'd talked about it. But he had to think about it at some point. Was he ready to go all the way? And… who would be taking on which position?

Penguin felt his face heat up thinking about it, even if he was alone in his room. How did one know what they'd like? He was unfortunate enough to know his father was a bottom vers, but did that mean Penguin was as well? Was that something that would run in the family?

Penguin shook his head. That was ridiculous. That couldn't be, right? It probably had nothing to do with genetics. But how would he know then? He glared at the butt plugs. Maybe he would just have to try it out to find out? Or maybe Killer already knew what he liked?

A sudden fear came over Penguin. What if what they both liked didn't match? What if they both wanted to bottom, or they both wanted to top? What if that meant they couldn't have sex, and that meant Killer wanted to break up with him? No, Penguin, don't start thinking in doom scenarios before you've even tried anything, he berated himself.

He tried to imagine different scenarios. What would it be like to top Killer? Penguin pictured it in his head. He… wasn't opposed to that idea. Yeah, he could probably do that… It was quite a sexy view in his head.

Then he tried to imagine what it would be like to be topped by Killer. Penguin bit his lip. He was definitely not opposed to that idea. Shit, that idea actually really turned him on. He involuntarily grinded his hips on the mattress.

So… did that mean he was a bottom? Penguin shook his head. It was too soon to say that. They would probably really have to experiment before they could know for sure. He eyed the butt plugs again. He could experiment a little by himself…

He quickly shove all the items underneath the covers of his bed, and jumped up. He went to the bathroom to brush his teeth and to make sure everything down there was as clean as possible, without actually having to use the douching bulb his father gave him. That seemed to go a bit too far for just trying some things out on himself.

When he was done, he walked halfway down the stairs, until he saw his father. "I'm going to sleep," he announced. It was around his normal bedtime anyway, so it wasn't that suspicious.

Law looked up. "Did you brush your teeth?"

"Yeah," Penguin said with a roll of his eyes. He wasn't five anymore.

"Okay, good night."

"Good night," Penguin replied. For a moment he hesitated. He could ask his father how he could know if he was a bottom, top, or vers… No, not a chance he would ask his father that. He'd find out by himself.

He went up stairs and into his bedroom. Making sure the door was firmly closed behind him, he let out a sigh. Okay, let's do this.

He stripped down completely and got into bed again. He returned the items he had hidden earlier to the pillow and quickly decided that he wouldn't need the biggest of the three butt plugs right now. He would have to build up slowly. First try out the smaller ones, and if he liked it, he could always try the bigger one. He put the biggest one away in his nightstand where the douching bulb was hidden from sight as well. Then he looked at the box with condoms. He wouldn't need one if he was by himself, but his father had said he should try one on to see if it fitted, so maybe this was a good time for that. It would also mean less cleaning up afterwards, so that wasn't bad either. He opened the box, took one package out, and put the rest of the box into his nightstand as well. Lube… he was definitely going to need.

Okay… how to start? Penguin rolled his eyes at his own uncertainty. It wasn't like this was the first time he would touch himself. He would just touch himself in different places. That didn't mean he couldn't start off as usual… it seemed like a good idea to get into the right mood first.

He lay down on his back and let his hand travel between his legs. He let his mind wander to Killer, while he slowly started stroking his cock to life. He thought back to the amazing blowjobs Killer had been giving. That had been so hot. He wondered when that would happen again. Killer had really seemed to enjoy himself giving him head, and that made the whole thing even hotter. That also made him think it would definitely happen again. Penguin bit his lip as he remembered what it had felt like, and what it had looked like. Shit, he didn't need a lot to get hard.

He was about to spit in his hand to make the stroking of his dick a bit smoother, when he eyed the lube. Well… that could work for jerking off as well, couldn't it? He opened the bottle and squeezed a little of the liquid in his hand. It was colder than he had expected. Putting the bottle aside again, he spread the lube over his hand, and then brought it towards his erection, continuing his slow strokes. Damn, that felt pretty good. He should have tried that sooner. He picked up speed a little, applying a little more pressure here and there. Fuck, yeah.

But before he really began to lose himself in the pleasure of it, he realized what he was trying to do. He wasn't just trying to jerk off. He had a mission. Penguin picked up the condom first. His cock being fully erect now, he was ready to try it on. He opened the packaging carefully, and applied the condom like it had been shown in class, by a very awkward teacher; pinching the tip and rolling the condom down as far as possible. The rolling down part didn't go as smoothly as Penguin had expected, but eventually he managed.

He looked at his condom-covered dick. It looked kinda weird; too smooth and a little too confined. But it did seem to fit. He let his hand, still somewhat slick from the lube, stroke it again. It felt slightly different, but not necessarily bad.

He kept stroking, and felt the pleasure build up again. Yeah, this was nice. A condom really wasn't that bad. He looked aside to the lube and the butt plugs again, thinking he was ready for the next step. He let go of his dick, and opened the bottle for a second time, this time coating the fingers of his left hand with the slick substance. He went to sit on his knees, and brought his digits towards his back entrance. He took a deep breath and slowly pushed his index finger in.

He winced. That felt… weird. Not bad, but not really good either. Penguin pushed his finger in as far as possible, and then slowly started moving it in and out through the tight ring of muscles. Oh… oh, that felt a little better already. He let out a breath he hadn't realized he'd been holding, and tried to relax some more. Oh, yes, that definitely felt a little better.

Penguin kept moving his finger in and out, starting to enjoy the sensation more and more. Still, it wasn't as good as touching his dick. He brought his right hand up to his cock and resumed his earlier stroking in time with the movements of his left hand.

Penguin's eyes widened in surprise. Holy shit! That felt good! "Fuck," he moaned softly, and he sped up the movements of both hands. Oh, this felt really, really good! The combination of being penetrated while he was stroking his dick was like nothing he had imagined. He kept doing this for a while, slowly losing himself in pleasure.

After a little while, he noticed it became easier for his finger to move in and out of his entrance, and Penguin tried to add a second finger. Ah, no, that was harder than he had expected. He tried to relax, but his hole was too tight to enter a second digit comfortably.

He looked calculating at the butt plugs next to him, and then stopped all movement, pulling his hands away from his body. He picked up the smallest plug and held it next to his fingers. It had to be slightly smaller than two fingers together, around the thickest part of it. And at the top it was way smaller, so… it might be easier to enter that than two of his fingers.

Deciding it was worth a try, Penguin coated the toy with another few thick drops of lubricant. After making sure every bit of it was slick, he brought it towards his entrance. He remembered in time to start stroking his cock again, so his body would relax more. He slowly pushed the plug in.

Oh, fuck, yes! Penguin's eyes rolled back in pleasure as the pressure on his hole build up more and more the further he pushed the toy in. And then, suddenly, the plug was sucked in completely except for the flat base. "Ahh!" he moaned breathily. Shit, that was nice! And it had gone in easier than he had expected. Penguin clenched his butt around the toy, as if to try and suck it in farther, while he kept slowly stroking his dick. Fuck, this was good.

He got a hold of the base of the plug with his left hand, and tried to pull it out. He felt some resistance at first, but when the thickest part was past the ring of muscles, the rest of it followed easily. Penguin chuckled at the sensation. Why did that feel so good?

As he pushed back in, he tried to imagine it was Killer, pushing into him. Obviously, Killer's dick was a lot bigger than this plug, but the image combined with the feeling of something being pushed inside him, was so incredibly hot! He tried this out a few times, the image of Killer never leaving his mind. Penguin's right hand sped up, and he threw his head back in pleasure. Shit, so good! He felt he was getting close to his orgasm.

There was a loud 'pling' from his phone, and Penguin's head snapped up. He slowed down his hand and hesitated for a moment whether he should check what kind of message he had gotten or try to finish first. He kinda wanted to finish, but at the same time he wanted to enjoy this a little longer. And what if the message was from Killer? He didn't want to miss a chance to chat with him, not even in the state he was in right now. Especially not in the state he was in right now.

He removed both his hands from his body, the plug being buried completely inside him again, and looked at them. Both his hands were kinda messy from the lube, so he decided to wipe his left hand as well as possible with a tissue, before grabbing his phone. He sat back against the wall, with his butt on the mattress. He felt the plug being pushed inside even a little further, and he moaned softly.

Penguin unlocked his phone, and saw to his delight that it was indeed a message on Discord from Killer. 'Are you awake?'

Penguin bit his lip as he slightly moved his hips again to take on a better position, feeling the plug shift as well. 'Yes,' he answered. 'What are you still doing up?' By now, it was already half past eleven, but he realized too late that Killer didn't have to go to school tomorrow.

'😏' Killer answered, and Penguin raised his eyebrows at that. 'Touching myself,' Killer continued. 'Thinking of you.'

A smirk broke through on Penguin's face. Was Killer for real? Was this a prank? No, that couldn't be, there was no way Killer could know what Penguin had just been doing. It had to be a coincidence.

'😳 Really?' he asked, nonetheless.

'Really 😉,' Killer answered.

'Like, right now?' Penguin wanted to know. Had Killer stopped his masturbation session to text him?

'Right now 😉 I need only one hand to type,' was Killer's answer, and Penguin blushed as he started picturing it. He couldn't imagine Killer was actually typing that fast with one hand, though. 'And you? Why are you still awake?' Killer asked him.

Penguin started typing his reply, but then he changed his mind. He could tell him… or he could show him. He opened his camera to take a picture of himself, when he realized he still had the condom on. That looked stupid when he was all by himself, so he quickly pulled it off him and tossed it aside. A little voice inside his head said it was a bad idea to send nudes, but God, he was horny, and Killer was clearly horny too, so he was going to send it anyway. He would just cover his dick with his hand, so there would still be something left to the imagination.

He did so, and bit his lip while trying to look seductive at the camera. He managed to snap a picture that had his face, chest, and crotch area in it, and he was pretty pleased with it. He send the picture to Killer, and added, 'Same.'

'Fuck, that's hot,' Killer replied, and Penguin smirked, pleased with that reaction. He slowly started stroking his dick again with his right hand.

To Penguin's surprise, he saw an incoming video call from Killer only moments later. He quickly grabbed his earbuds from his nightstand, and put them in. With every movement of his body, he felt the butt plug move slightly inside him. He moaned softly at the sensation, before he answered the call. Killer didn't need to know he currently had something up his ass. That felt just a little too embarrassing to share. Besides, it kinda added to Penguin's excitement to hide that little thing.

As soon as the video opened, he saw Killer lying on his side on the bed, naked chest full in view, but the camera cutting off just before the most interesting part. Killer had his finger pressed against his lips. "Ssshhh," he said, before Penguin could even open his mouth. He continued, whispering, "If my father hears us, we're dead."

Penguin chuckled, making sure his camera also cut off above his hips. "But you're willing to take that risk…" he whispered back.

"Fuck, after that photo you sent… How could I not?" Killer answered him, lust evident in his hushed voice.

Penguin smirked. "Well, if you put in earbuds, he at least won't be able to hear me."

"You're right," Killer said, apparently not having thought of that himself. He got up and left the view of the camera completely for a few seconds, before returning and leaning closer to his laptop to plug in his earphones. Penguin thought he must have put his laptop on his nightstand. Killer lay back down on the bed and popped himself on his elbow. "Yes, that's better. Now you can make as much noise as you want."

Penguin hummed and shifted his hips to feel the butt plug again. He saw Killer's right hand disappear from view, towards the lower half of his body, and Killer let out a breathy moan.

"Killer…" Penguin groaned softly. Even though Killer was wearing earphones, he still didn't want his own father to hear him. "That's just mean."

He saw Killer smirk at him. "What is?" he said quietly, but teasingly. It was obvious he didn't stop the slow movements of his hand.

Penguin started rolling his hips slightly, rocking his erection into his hand, and his butt onto the plug. He moaned softly. "You know what. Show me the goods."

"The goods?" Killer feigned ignorance.

Penguin gave him a heated stare. "Your cock, Killer. I want to see the cock in your hand."

Killer moaned quietly, and then adjusted his laptop, so Penguin got to see what he longed for. Fuck, that was such a hot sight. He closely followed the movements of Killer's hand up and down his own shaft, and Penguin bit his lip as his own hand mirrored the movement.

"Peng, I'm glad you're enjoying the view," Killer whispered. "But don't you think I deserve the same?"

Penguin smirked and moved his phone too, so his own erection came into view. He didn't stop stroking himself.

"Fuck, Peng, you're so hot," he heard Killer's voice in his ears, sending pleasurable vibes straight down to his dick.

Penguin bucked his hips, and squeezed his ass around the toy in his butt. Shit, this was so good. He had a hard time not letting Killer know exactly what was going on.

"How far were you when I texted?" Killer asked, breathing heavily.

Penguin bit his lip. "So close." He already felt the pleasure build up again.

"And yet you picked up your phone?" Killer asked surprised. "Or were you watching porn on your phone?"

Penguin snorted. "Nope, I wasn't watching anything. Just thinking about you. But I didn't want to miss a chance to say good night if it was you who texted me," he answered, all the while he kept moving his hand.

Killer hummed appreciatively. "Well, this is the best goodnight you could give me." He sped up his hand a bit. "Fuck, this is such a hot sight."

Penguin's hips trembled. Shit, he was already so close again. He forced his own hand to slow down, so he could last a little longer. He moaned softly. "I wish you were here right now. I want you so bad, Killer." Penguin wasn't completely aware of what he said anymore. The pleasure caused by both the friction around his dick, the feeling of the plug in his butt, and the view of Killer jerking off was just too much to think straight anymore.

"Same, Peng, same," Killer whispered breathily. "Let's come together."

Penguin let out a sound somewhere between a laugh and a whimper. "Then you gotta be really quick, 'cause I can't hold much longer." He almost stilled his hand, but he wanted his release so bad, he didn't know if he could wait for Killer.

Killer moaned softly. "Okay, you come first. I love watching you come, it's so hot."

Penguin didn't need more encouragement and sped up his hand again. Fuck, the pleasure, it was so good! It took him only a few more strokes until hot, white liquid spilled over his hand and stomach. "Ahh-ah!" Penguin wasn't able to stifle the moan that escaped his throat. Shit, that was intense.

"Fuck," he heard Killer breathe in his ears. Penguin forced his eyes open again to watch his boyfriend as his hand slowly came to a stop, having given all he had to give.

"Fuck, Peng," Killer moaned softly again. "You have no idea how hot you are," he said, panting heavily. "Especially when you come all over yourself."

Penguin watched mesmerized how Killer worked himself for a few more moments until he too spilled his semen, mouth open, but not a sound louder than a breath coming from him. Penguin bit his lower lip until it hurt. Shit, he got it. If he himself looked anything like that when he came, Penguin got why Killer thought it was so hot.

There was something so intimate about watching his boyfriend masturbate until he came, and realizing Killer had seen him doing it as well. Penguin blushed. And Killer didn't even know about the plug in his butt. He did want to get that out now, though. But he'd had to wait until the call had ended, because he still didn't want to let Killer know about that.

After a minute of getting his breath back, Killer looked at him and smiled. "Thank you for indulging me," he whispered.

Penguin chuckled, slightly embarrassed all of a sudden. "Thank you for calling me."

Killer kept looking and smiling at him in silence for a few seconds, before he sighed. "I wish I could hold you right now."

Penguin felt the butterflies fluttering around in his chest. "I know. Me too."

"Can't wait for this stupid week to be over," Killer complained. "I mean, I really don't see a way to sneak out. You could sneak in, of course… I could let you in through a window, but my father seems to be home at all times, when he's not at work. And he works during school time. So, I can't really see that happening either. He made sure he doesn't have to go anywhere for longer periods of time this week."

"That sucks," Penguin said, but an idea started to form in his mind. He didn't want to let Killer know, though, in case it didn't work, and he would get his hopes up for nothing.

"Yeah," Killer agreed, but then he licked his lips and smirked. "And I'd much rather do the sucking myself."

Penguin snorted, but blushed. "You have a dirty mind."

"Like you're the one to talk," Killer answered teasingly. Then he quickly turned his head away from the camera, the smirk disappearing from his face immediately, and he brought his finger to his lips again in a gesture to stay silent.

Penguin said nothing and watched Killer look anxiously aside, probably looking at his door. After several long seconds, he sighed. "I gotta go," he whispered even quieter than before. Only then he looked back at Penguin. "I hope you'll sleep well."

Penguin smiled. "I don't think that will be a problem now."

Killer chuckled quietly. "I'm glad. Good night."

"Good night," Penguin answered, and he blew a kiss towards the camera before ending the call.

TBC~!