Good Guys Don't Date Bad Boys - 17. A Story Of Firsts

Chapter Seventeen – A Story Of Firsts

Totally, a part of him liked to torture Jonathan even if it meant that he put himself through the wringer in the process. His cock was at the point of bursting, and the earlier session on the sofa, as hot as it had been, was totally gone from his mind. Definitely, that hard throbbing part of his anatomy couldn’t remember a thing and now wanted to sneak into a certain enticing hole.

“I’m not going to show you my asshole,” Jonathan protested. “This is getting ridiculous.”

“Oh, yeah? Then please turn and face me so I can see just how ridiculous you think this is.”

Jonathan moved but kept his hands linked in front of his midsection.

“Nah-ah, no cheating. Take your hands away.”

An unintelligible mumble accompanied obeying his order, making Maddox’s grin stretch wider. Jonathan was totally pitching a tent and, frankly, Maddox was glad that the sexy briefs hadn’t come off yet, because there was something he wanted to do very much. “Come here,” he ordered.

There were no protests as Jonathan climbed on the bed, but his whole body was tense, and uncertainty lurked in the amber eyes. Maddox reached for him and cupped his cheek. “Don’t worry so much. Right now, I just want to kiss you.”

A small exhalation followed, and Jonathan aligned his body with his so that they could kiss. However, he didn’t sit there passively but moved one hand and wrapped it around Maddox’s erection and rubbed it slowly.

Maddox surely didn’t want to be left behind, so he snuck one hand around to grab Jonathan’s ass. His fingers reached under the briefs and went for the prize. Gosh, he wanted this so much, even if it killed him to think that it could be over once they were finished.

Nah, he wasn’t afraid anymore. Jonathan’s mouth was freaking addictive, if only for those mad kisses, and he wouldn’t get over it so easily. The guy kissed with everything he had, and he was the kind of kissing fiend Maddox loved the most. Their breathing was growing increasingly difficult as they devoured each other’s mouths, tongues wrestling.

He broke it off only in order to look at Jonathan and get the confirmation he wanted. The amber eyes were hazy, and they were so much more beautiful from up close. Maddox brushed his nose against Jonathan’s playfully and earned a small giggle in return. “I have no idea about you, but my cock is threatening to detach itself so that it can sneak behind you and bury itself in your ass.”

Jonathan caressed his jawline and gave him a small kiss. “We can’t have that, right?”

He surely tried to play it cool, but his cheeks were on fire, and his lips were adorably swollen from their kisses.

“I suppose I should get into position,” Jonathan said and bit his bottom lip.

“Yeah. On your back,” Maddox said.

“Um, you sure? I think I should--”

“We’ll do it doggy style later,” Maddox said promptly.

Jonathan didn’t seem too convinced but lay on his back. Maddox grinned and pulled down his briefs, his cock prancing happily once out of its confines. Remembering his promise, he dunked his tongue directly into Jonathan’s belly button, earning an instant gasp of surprise. Too bad he couldn’t be bothered with too much teasing at this point, so he just gave it a small lick before going lower and brushing his lips against a glistening mushroom head in passing.

He smirked as he stood at the edge of the bed and began undressing. Since no buttons of any kind stood in the way, his striptease show was short-lived.

***

Now he understood what Maddox meant by wanting to take a good look at him. Just watching the other undress was the sweetest type of torture. He liked Maddox’s body in the extreme, all that manly hair in all the right places. It was true that he preferred his own body smooth, but just now he realized that it might have been his secret plan to keep it that way so he could experience rubbing his skin against a body like that.

And that amazing cock, so hard for him right now, was designed to render him speechless. Jonathan let out a long breath, trying to release the tension he felt building inside him. Maddox didn’t allow him much time to admire the sight in front of him and climbed on the bed again with a naughty glint in his eyes.

Jonathan released a small confused whimper as Maddox pushed his legs up and stared directly under his balls.

“Hold them,” Maddox said, and Jonathan grabbed his legs.

He felt so vulnerable, exposed like that, and it appeared that Maddox was comfortable down there, spreading his ass cheeks and tuning in his entire attention to a single point.

“You and I, we’re going to be great friends,” Maddox said.

“Um, okay, but how about looking at me when you say that?” Jonathan asked, his breathing uneven, growing more ragged by the second. Suddenly, he had weird thoughts about that certain part of his anatomy. Was it enough to convince an experienced guy like Maddox to fuck it?

“Hush, I wasn’t talking to you. I was talking to this little hole.”

“Really? I think it’s part of my body.”

Maddox hummed under his breath and used his fingers to tease Jonathan’s asshole. “It’s so smooth. Unlike you.”

“What do you mean?”

“You’re cactus-level prickly,” Maddox replied promptly. “But not this thing. Oh, fuck, I’m going to lick it.”

“Maddox, no!”

“Too late.”

Jonathan moaned instantly the moment he felt something wet and naughty pressing against his backdoor. He had no idea it would feel like this. Fantasies notwithstanding, reality didn’t come close to this, for the simple fact that it belonged somewhere up, up, outside the known universe. Pressing the back of his hand over his mouth to prevent other shameless sounds from escaping, he found himself dizzy with too much pleasure.

Maddox moved his tongue slowly. It could be that he had had plenty of practice, but Jonathan didn’t want to let his mind wander there. Thinking of Maddox in the arms of nameless faceless girls made him feel possessive, and this game was not about ownership. He was simply being granted the realization of a fantasy of the best kind, so enjoying it and letting worries pass were the only course of action he should take.

Who knew nerve endings would be only skin-deep there? He had touched himself, surely, teased around, but nothing, absolutely nothing compared to the feeling of being probed so gently with that softer-than-velvet tongue. He could die. Much to his relief, Maddox didn’t insist on continuing his rimming for long, eager, most probably just like he was, to get to more practical things.

“Thanks,” he mumbled weakly.

Maddox’s playful chuckle did nothing for his nerves. “You’re welcome. I definitely like eating you out.”

Another hitched breath followed as Maddox teased his balls, this time with a long swipe of the tongue.

“You’re bent on making me come before you even put your cock inside me,” Jonathan accused.

“So damned sensitive. I like it,” Maddox declared. He straightened up and pushed his fingers against Jonathan’s hole, exploring slowly.

Jonathan risked a look. Maddox loomed above him, looking as ridiculously sexy as always. His hair had gotten a bit in his eyes, and he had a satisfied grin on his face. He was so close he could touch him, so Jonathan did and ran one hand over Maddox’s cheek and then brushed the hair back. There, now he could look at his face and take in every line of that handsome masculine face. Something to remember later.

“Are you having second thoughts?” Maddox asked, a bit alarmed by the look in his eyes.

“With your dick poised to enter my ass? I wouldn’t do that,” Jonathan said, shaking off the worrisome thoughts that never left him alone.

“Ah, so you don’t want to be cruel to me, right?”

“And myself,” Jonathan replied and pulled Maddox in for a kiss.

His tongue was so sweet that one could live off it forever, yet still crave more.

Maddox broke the kiss. “I’m doing you raw, right?”

The question, loaded with hope and desire, brought him back to reality. He nodded, not daring to speak a word. Maddox, naked on top of him, his bare cock in his ass – that was the stuff fantasies were made of.

“So, this is the part where we get the lube,” Maddox said.

Jonathan stared at him, dazed and beyond help. Maddox’s kisses always left him a bit daft. He watched the other moving about, his bobbing cock drawing his gaze more than anything right now. “Wait, I did bring some,” he said as he finally remembered.

“No worries,” Maddox said and showed him a tube filled with clear liquid while climbing on the bed. “The least I could do was be ready for this.”

Oh, he was ready if the leaking head of his cock was any indication. Jonathan felt overpowered by a desire to stick his tongue in the little eye and lick every last drop. So he reached for it and brought it close to his mouth, ignoring Maddox’s slight protests as he was being forced to straddle Jonathan’s chest.

“Why are you so good at this?” Maddox moaned.

“Practice,” Jonathan said with a smile.

Maddox’s cock was rock hard in his hand, making him tremble in anticipation. How would it feel inside him? He licked the head from all sides, his eyes shooting up at the other from time to time.

“Fuck, you were made to take cock,” Maddox praised him while running a hand through Jonathan’s hair.

The lewd comment made him shudder with new want. He would keep Maddox there, teasing him if it meant that he could hold him forever. But that wasn’t why they were there. “How about we test that theory?” he made an attempt at a joke, but his voice was low and hoarse.

Maddox smiled and moved down on his body. “So, any last words?”

“What?” Jonathan asked.

“You know, as a virgin boy.”

Oh, gawd, this boy and his funny side. “Just fuck me,” he said.

The grey eyes twinkled. “Say ‘please’?”

Jonathan snorted, but Maddox’s fingers, now coated with lube, teasing his entrance, brought the excited shivering back. “Please fuck me, Maddox,” he said in a heated voice that he could barely recognize as his own.

“Happy to,” Maddox teased him, but his voice was low and deep, too.

Why were they in this position? Jonathan had hoped for the mercy of being taken from behind, so that he didn’t have to look at Maddox too much that first time. A part of him wanted it, oh, wanted it so badly, but memories like that were bound to turn into tiny heart scars as time passed.

Even so, he told himself, no regrets for now. He wrapped one hand around the back of Maddox’s neck, and rested his other just above that curvy ass. His fingers inched along the crack while Maddox pressed the head of his cock against his hole.

Jonathan took one deep breath. It was no secret that it would hurt some, but he was ready for it. Still, the first sting took him slightly by surprise.

“I need to go slow,” Maddox mumbled under his breath. “Fuck, you’re so tight.”

“Sorry about that,” Jonathan whispered.

Maddox leaned in and kissed him while pressing him hard against the bed. The weight on him, the nice smell of the other’s skin, were soothing in a way. He could still feel the hard cock, patient but relentless at his backdoor, but he was getting used to the stretch. Maddox moved away, making him whimper at the loss.

“We need more of this,” Maddox explained, grabbing the lube again.

The teasing fingers came back, this time going deeper and moving around. Jonathan gasped and moaned as new sensations filled him. He truly needed to stop staring at Maddox; the mere sight of him was too much, and there was a new feeling pooling inside his groin with each slow thrust of the skillful fingers. “Enough,” he said raggedly, “I need you inside now.”

Maddox didn’t joke around and aligned his cock again. This time, he went a little deeper, but by the strained lines of his face, he was doing his damnest not to go too far too fast. Jonathan pulled him close and pressed on the small of his back. “Now, Maddox,” he whispered.

“You sure? I’m wrecking your ass.”

“Stop flattering yourself. You’re not that big,” Jonathan lied only because he couldn’t bear another moment of not having Maddox buried to the hilt inside him.

He silenced both their moans by kissing Maddox hard, as the other pushed himself in. To stop himself from wanting to get away, he wrapped his legs around Maddox and pushed his heels into his buttocks.

“Fuck, you’re crazy,” Maddox whispered. “Are you sure this is all right?”

“Yes,” Jonathan breathed out. He was so full he felt like choking, but, at the same time, his body craved it. “Give me a second to get used to your girth and then you can move.”

“Glad you have it all figured out,” Maddox said. “Fuck, this feels so nice.”

“It does?” Was he so desperate for validation? Yes, he was, when it came to Maddox. The hard cock throbbing inside his ass provided plenty of that, too.

Maddox caressed his chest and caught a nipple between his thumb and index finger. Jonathan moaned at the new sensation, enjoying how rough that felt. A new wave of arousal hit him, and he barely registered Maddox starting to move, first slowly, then accelerating to a hammering pace.

“Oh, fuck,” he whispered, “you’re big.”

“Glad to see you’re finally acknowledging the might of my cock.”

He was still capable of joking, but his eyes were hazy and displayed nothing but the soaring desire between them. By now, reality should have caught up with Maddox and, as a straight boy, maybe he should have realized that he didn’t really want to fuck a guy’s ass. None of that appeared to be happening. If anything, Maddox was growing more and more relentless as he pushed inside him fast while moaning and biting his lips. From time to time, he reached for Jonathan and pulled him in for a kiss.

“Does it feel good at all?” Maddox asked breathily. “Cause on this side, it feels freaking amazing. Fuck, you take me so well.”

“Yes,” Jonathan keened softly as the other’s cock slamming inside him made him experience everything the books and songs talked about, a sensation like no other that had everything to do with his body but not only. He stared down at his cock, slapping against his belly. Maddox surprised him by curling one hand around it and starting to rub it. “Damn, just look at how hard you are,” he said with unhidden admiration.

“It’s because of you,” Jonathan whispered. “Maddox, your cock, inside me, it feels so good.” He didn’t have any better words to describe it.

“You must be a total bottom boy,” Maddox teased him while he matched the movement of his hips with that of his hand on Jonathan’s hard-on.

The sensation grew in intensity. While before it had felt sort of out of reach, now the climax was very much in sight. Maddox buried himself to the hilt, making Jonathan feel his balls against his ass, and squeezed his cock hard, making him squirm helplessly. His pleasure was literally out of his hands, and that thought of complete abandonment should have scared him.

But it was impossible to feel afraid. Maybe he was too aroused, too far gone, to feel anything else.

“Are you?” Maddox teased him more. “Are you a bottom boy?”

There was an unveiled challenge in those words. Jonathan moved the hand he held Maddox’s ass with and teased his crack again. That simple gesture was enough to make Maddox move more desperately and moan louder.

“Maybe you are one, too,” Jonathan teased back. “You can’t tell until you have a huge rod like yours in your ass.”

All the while, his fingers got more daring, earning multiple tiny pleas from Maddox in the form of grunts and under-the-breath curses.

“I can’t fuck myself,” Maddox breathed out, “so I wouldn’t know.”

Jonathan pressed on the hot hole under his fingertips. He couldn’t go too deep from that position, but he could tell Maddox appreciated the teasing. Even if it was probably the kind of thing quickly discarded and forgotten once they finished, it looked like a certain top dog didn’t mind having his backdoor played with.

Maddox kissed him hard and moved his hips amply. Jonathan felt everything, especially the hard cock in his ass, hammering away, and bringing them closer to the point of no return. He shivered and moaned as Maddox jerked him off faster and faster.

The cum erupted so hard from his cock that it hit his chin.

“Fuck, yeah,” Maddox groaned.

Jonathan felt like he was coming forever. His entire body was coming, and he sealed his first time and goodbye to anal virginity by kissing Maddox deeply. Then his cock was let go and his hips grabbed hard. Maddox must have held back until now because he slammed hard inside him and it took him only a few thrusts to announce his victory.

***

Maddox lay on his back, completely spent. “Your ass is it,” he let out, first thing.

“Glad you enjoyed it,” came the ragged reply.

Somehow, in the course of it, they had both lost their voices. He pushed himself up on his elbows to look at Jonathan. His smooth chest was covered by a sheen of sweat, and he looked good enough to eat, with all that cum spread all over him. His was inside Jonathan’s ass, and he was so damned curious to see it. If he thought about it now, he had never done it with anyone without a rubber. No relationship before had been serious enough for that to happen. But Jonathan was a virgin - no, correction, he had been - and Maddox had proven his cum was not radioactive.

Beyond the practicalities, however, only a single truth stood: that Maddox had wanted to pump Jonathan’s ass full of cum. He hadn’t thought of that till this dude. Sex was sex; it was good, and it didn’t matter that he always came inside a piece of rubber. But now, he was satisfied in new ways. The moment he had felt his cum flowing freely inside Jonathan, his mind almost shut down on itself like an absolute moron.

“So, how is it? You’re not a virgin anymore.”

“My ass knows that, believe me.”

“Could you turn?”

“Um, why?” Jonathan asked. “How?”

“Just on your side. Back to me. A little.”

Jonathan obeyed and turned his back. Maddox didn’t waste a moment and grabbed a round buttock so that he could stare properly.

“What are you doing?” Jonathan asked over his shoulder.

“I came in your ass,” Maddox said and grinned.

The amber eyes twinkled at him. “Without a doubt. I very much feel it.”

Maddox played around the hole, spreading the cum. Jonathan whimpered softly. “What else do you feel?”

“Like your cock molded the inside of my ass into something else,” Jonathan said.

And that was also most satisfying. “Good.” Maddox slapped Jonathan’s ass once quickly, earning a small offended gasp from the other. “I can barely wait to do you from behind.”

“Are you sure? You came an entire gallon inside my ass already,” Jonathan complained.

“Trust me, baby,” Maddox said playfully, “there’s more where that came from.”

“Really? How much? I need to prepare mentally for it.”

He could joke. That pleased Maddox because hey, he doubted anyone else could brag that Jonathan liked to joke around with them. He leaned in and kissed a sweaty shoulder. “Fuck, I think I want you again.”

“You think?” Jonathan didn’t turn to face him but searched for Maddox’s cock with one hand. “Oh, you are indeed hard again.”

“All it took was playing with my cum in your ass. You wouldn’t believe the sight. I should take a picture.”

“No, you shouldn’t.” Jonathan’s voice was brusque and his hand moved away from Maddox’s cock.

“All right,” Maddox agreed. Whatever that was, Jonathan didn’t like having his pictures taken or something. It wasn’t like he would show such things around, but right now, he didn’t have time to dwell on his reasons. Or to spoil the mood by saying the wrong stuff. “I mean it,” he insisted as he felt the other tensing. “It was just a manner of speaking, nothing more.”

He took Jonathan by the shoulder and turned him. “Would it help if I said ‘cross my heart and hope to die’?”

To his relief, Jonathan smiled and kissed him. “Yeah, it would help,” he teased.

But he didn’t allow him to say another word as he kissed him more, deep and demanding. Maddox didn’t mind having Jonathan on top, but he was too keen on his promise to take the guy from behind.

So he grabbed Jonathan’s ass cheeks and squeezed them hard. “Doggy style, babe, right now.”

“Babe,” Jonathan repeated and snickered like a kid. “Oh, I’m such a babe,” he said in a false coquettish voice.

“Okay, hunk, should I call you that?”

Jonathan shrugged. “Call me whatever you like.” He let go of Maddox so he could place himself on all fours.

“Yeah, babe,” Maddox teased him, “let me see you wiggle that ass.”

To his surprise, Jonathan threw him a sultry look and began moving his ass in what looked pretty much like twerking.

“What the hell did you learn at your all-boys school? How come you know how to twerk?”

Jonathan laughed and hid his face in the crook of his elbow. Maddox wasted no more time and placed himself behind him, hands on the naughty buttocks challenging his cock to do something already.

“I didn’t learn it there, obviously,” Jonathan replied in a whisper. “Just on my own.”

Maddox snickered. “Your choice of hobbies is something, Hamilton. No wonder you can drive me crazy with one look.”

Okay, so that sounded pretty lame, but it was true. It had been enough for Jonathan to look at him, that first time, and Maddox had felt like he needed to know what the dude’s deal was all about. And that had quickly turned into an overwhelming attraction that he didn’t even struggle to fight anymore. He had gotten the boy where he wanted him, on all fours, presenting his ass, ready to surrender.

The first time had been mind-blowing, but right now, Maddox wanted to make it count and pay attention to everything because Jonathan deserved all of it.

“Are you going to put it in already?” Jonathan stopped his train of thought. His voice was a tiny bit strained, and only then Maddox realized that he had been pressing his thumb inside the pretty hole, teasing it for a while now. He had come so much that there was still plenty of his cum in there.

That was a most satisfying thought. “Just look at your ass swallowing my meat,” he said with unhindered wonder in his voice as he began to push inside.

“I can’t really look, so stop torturing me,” Jonathan complained in a breathless voice. “I thought it would feel smaller the second time,” he added. “Or that my ass wouldn’t be so tight anymore.”

Slipping inside was easier, but otherwise, Jonathan was right. His ass was still deliciously tight, massaging Maddox’s cock along its length, and it was pure pleasure just to go in and out and enjoy the friction. With this guy, everything felt like conquering new territories, and Maddox didn’t mind being the victor at all. He moved his hands, pressing against the firm ass cheeks, pulling them slightly apart so that he could enjoy that sight more. With satisfaction, he touched the rim of Jonathan’s hole, now tenderer and slightly puffy. No wonder there, Jonathan was right that his ass was feeling it and would feel it later, too.

There was no better reward than that. He had put his mark on this person, something that they wouldn’t forget forever. And in a way, it was a story of firsts for the both of them. For Jonathan, things were clear. No matter what the Asshole had meant to him, Maddox was his first man, his first proper fuck, and there was no way around it. As for Maddox, it was his first time with a boy, and again, the first time doing it raw, and it felt like it meant more than just the kinkiness of it should have.

Between them, there now existed a sort of intimacy that neither had shared with anyone else before in their lives. No way could this be just a hookup, Maddox decided. He was bent on getting Jonathan on his back, all fours, sides, or whatever, plenty of more times. With low grunts, he pushed himself inside the welcoming hole, making Jonathan gasp and moan with each thrust.

With girls, he had been considerate, not ever going full in, their slim bodies too fragile in his mind to be as hard as he wanted. But Jonathan’s muscles were supple under his fingers and hard, and a new sense of satisfaction grew inside him as he realized that, just as Rusty had said, this dude could take it.

“Fuck, fuck, fuck,” he groaned as his body slammed hard against the other’s. “Jonathan, can you feel me?”

“To the back of my throat,” Jonathan said back in a strained voice.

Fuck. He was too rough. He needed to slow down.

“Harder,” Jonathan pleaded with him.

He could tell that the other was rubbing his cock, supporting his weight on just one arm. Sweat was pooling at the small of his back, and Maddox was in love with the sight.

“Faster,” Jonathan ordered, his voice more urgent.

Maddox dug his fingers into the sturdy hips and began moving with complete abandon. His cock was in fucking anal heaven, enjoying going so deep and fast and hard. He heard Jonathan grunting and moaning and felt the walls of muscles around his cock pulling close, a sign that the other was surely coming from all that hammering.

He couldn’t keep from coming now if it killed him. It was the best fuck of his life, without a doubt. He held Jonathan’s ass impaled on his cock as he came and came, filling that freaking awesome opening with more of him until he felt like he couldn’t go any higher.

His cum came gushing out of Jonathan’s ass the moment he let go. “Fuck me,” he whispered and laughed.

“Maybe another time,” Jonathan teased him and collapsed on his belly.

“Nice try, bottom boy,” Maddox teased back and slapped the gorgeous ass in front of him playfully.

Jonathan was breathing hard and said nothing, probably too tired to get into any argument, no matter how superficial. Maddox stretched out by his side and threw a possessive arm over his body.

“Jonathan,” he said in a much more serious voice, “that was amazing, for real.”

The amber eyes searched his face. “I’m glad you liked it,” came the whispered reply.

“What about you?” Maddox asked.

“Do you really need to ask?”

“Yeah, I do.”

Jonathan examined him again for any signs of teasing. “I’m at a loss for words. I was expecting to hurt more, to be more uncomfortable, you know? But I guess you know your thing.”

His thing. Like in being an experienced fuckboy. Maddox hadn’t any idea why that bothered him.

“It’s not like I’ve fucked other dudes before you.”

Jonathan scooted closer and kissed him sweetly. “And I’m so happy you haven’t.”

No matter how clumsy both of them were, that was simply the truth. That they were both happy to be each other’s first.

TBC

Well, that was their first time... not over yet, and there will be other times, I promise! I hope you enjoyed the chapter, and that it lived up to expectations! More to follow, so stay tuned
Until next time,
Hugs,
Laura.