Dating Rules and Pretty Fools

Chapter Eighteen -- No Regrets

A small gasp falling from Otis's lips made reality fade even farther away. Life could be so simple if he only let it happen, like right now. The tension keeping him so strung day after day slowly unfurled and drifted away as he let his hands roam all over his lover's curved back until they reach their intended destination.

Otis gasped louder and, this time, pushed him slightly away. Both his eyes, pretty and startled, set on him. "Is this the night when you..." He swallowed and then averted his gaze.

Hudson chuckled. "Ask me anything, Otis. The answer will be 'yes'. Unless, of course," he teased gently, "you want me to go back to my place and sleep on that horrible sofa only to get up tomorrow with pain in my neck."

"No, absolutely not," came the honest reply. "Then I want you... I want you..."

"Yes," Hudson encouraged him and smiled. He brushed Otis's hair out of his eyes completely and kissed the now exposed forehead. "Here's another quick lesson for you, since I know you're such an avid learner. You can be as bold and naughty as you like. So, go ahead, sweetie, say it the way you want to say it."

"Can you put it... in?" Otis's voice dropped to a whisper now.

It only made him want to tease his beautiful neighbor some more. "In... where?"

"In my butt," Otis said in the same low whisper and then giggled.

"I don't see why not," Hudson said, more brusquely than intended. His cock twitched painfully at the offer. Men like Jackie were waiting on the sidelines. Why let his precious Otis wait for him to make the right move -- because it had to be right, his entire body was urging him to believe it -- and maybe leave him ripe for others to have him?

Even if he ever came to regret this, it felt too right to be wrong. Hudson pushed Otis onto the bed and climbed on top of him. "Do you know what you're asking for? Is this something you need crossed off some list?"

He moved his crotch against Otis, happy to find that the gorgeous man underneath him was suffering the same affliction as he was.

"I do have a list," Otis admitted and made himself sound so guilty that Hudson couldn't help himself.

He captured the soft lips between his and dove into the kiss, slowly, without any predictions or planned strategies in mind. Nothing would stand in the way of crossing everything off Otis's list; he was there for that and more.

"You don't mind?" Otis asked as soon as Hudson allowed him to breathe. "That I have a list?"

"If it were anyone else but you, I'd be a little annoyed. But it's you, Otis," Hudson said and caressed his hair, "and don't mind my words right now, but I wouldn't let anyone else have you, not if it cost me everything."

Otis nodded slowly and blinked. There was a high chance that he didn't quite understand what Hudson was going on about, but it didn't matter. Who knew where life would take them in the future? It was something he preferred not to think about right now, no, not now when he wanted Otis so much and it felt as if there was nothing else in the world worth wanting.

"Then have me," Otis offered himself with the same candor that made him who he was.

Hudson moved only so that he could undress himself, aware of the awe in the pretty blue eyes fixed on him, without blinking. Maybe it would be unnerving for some people, but not him. No, without one shadow of a doubt, he wanted to have those eyes staring at him like that forever.

***

Who was he to deserve a man like this? A creeping little thought, thin as a spider's web, began wrapping itself, cutting like a razor's edge, around his mind. Hudson was the kind of man anyone would want, unless they had very peculiar tastes, such as not liking muscles, or perfect proportions, or manly body hair, or...

His thoughts were brought to a halt by Hudson climbing on the bed again to kiss him. Otis loved those kisses. They were beyond pleasant; they sent tiny eddies of warmth across his body down to the tips of his fingers and even his toes. But more than anything, Otis sensed something akin to an unknown feeling growing inside him while Hudson kissed him so completely. He no longer belonged to himself. Give and take were perfect words for such a surrender, because he knew that he could never be the same once he gave himself to his boyfriend right now.

"We should get you undressed, too. What do you say?" Hudson asked and teased his lips again, only biting them gently.

"I should, of course," Otis replied right away.

His hands were uncoordinated and his moves clumsy as he removed his shirt and undershirt. Hudson helped him with the rest, and soon he was naked. Although he had been like this before in his neighbor's company, now he felt even more naked than he had been before. How could it be possible, to feel yourself more than something you already were?

His hands moved to cover his front, but Hudson chuckled and pushed them away.

"It's all right to be nervous."

That was good to know. It meant he wasn't strange or abnormal. All these new things, would they help him become who he wished to be? He hoped so, and the part that made him feel all warm inside about it all was that he knew he had someone to rely on, someone who liked him, despite all his weirdness.

Hudson made him part his legs and brought his head down. Otis let out small puffs of breath as he felt the warm mouth he knew now descend over his cock and engulf it fully. He was only slightly aware, as if he was a faraway witness to it all while still being inside his body, of the short cries of pleasure he let out while his cock was squeezed and wrapped in that perfect heat.

"Would it be bad if I came?" he asked through his strangled moans.

"Come, baby," Hudson cooed and returned to devouring his cock in the same manner that was destined to blow his mind.

That was all he needed, and his entire body shook with the intensity of his release. He knew Hudson was drinking him, that part of him, and the thought made him so happy he couldn't express it. The best part was that he didn't have to express it at all, save through moans, shouts, and groans that all melted into the same expression of gratitude.

He gasped in surprise as Hudson turned him and placed him on all fours. A look over his shoulder assured him that something equally amazing was bound to happen and soon. His entire skin caught fire as he saw Hudson opening his mouth and letting the semen on his tongue pour down.

His crack was slowly getting wet, as Hudson moved his tongue along it, while his eyelids drooped like a lazy cat's. Otis wanted to tell him that he was embarrassed, that he couldn't take it, but it wasn't what he wanted to say and, for a change, he said nothing and waited for good things to happen to him.

Something inside him throbbed with new want as Hudson proceeded to lick his butthole at leisure, shooting a glance at him from time to time.

"Now, this is something that needs proper consideration," Hudson explained as he pushed himself up to his feet. "We will take it slowly."

Otis put one hand back and felt his opening. It was quivering with desire, just like the rest of him. "You're talking about having it lubed, right? I bought something online," he admitted as his cheeks caught fire again.

"You did? You're a man with a plan, baby, I have to give it to you."

Hudson laughed and moved, making his amazing erection bob up and down as he did so. He followed the instructions and retrieved the needed lube and condoms from the indicated drawer.

"Wow, you even bought different sizes."

"I had no idea what sort of size would be the proper one," Otis explained. "You look like XXL," he said, his eyes unable to move away from Hudson's impressive cock and the glistening piercing for more than a few seconds at a time. "Those are also larger in girth not only in length," he explained, eager to point his boyfriend in the right direction so that they could get back to the job at hand.

"These are the brand I use, and I did have one on me," Hudson said. "But this is really helpful, Otis, because I don't think I'm going to limit myself to just one time with you tonight."

Could they do it more than once? Otis felt his heart fluttering in his chest. His stomach was also doing some things he couldn't quite describe.

"Then could you please hurry? What if tonight is not enough?" he voiced out loud some thoughts that crossed his mind.

Hudson laughed, throwing his head back, his hands full with the things they needed to make that particular thing happen. His throat captured Otis's imagination the most. He liked it. He could see himself licking that Adam's apple and smelling Hudson's natural body scent.

He must have let out a short strange sound, because those dark eyes that unnerved and pleased him at the same time set on him.

"I should get to work, then. Since you're such a busy man and probably worrying about being in shape to go to work tomorrow."

That wasn't what he had meant, but he didn't have it in him to explain it all to Hudson in minute detail, because rough yet gentle fingers were at his backside and now they were slowly getting in. Otis had read serious literature on the subject; if asked, he knew how to explain what was going on, but his mind was empty now. There was nothing in his brain except for that sensation of increasing pleasure. The aforementioned literature, he remembered vaguely, explained a lot of things about avoiding pain, and it looked like Hudson must have read it, too, because all he did caused pleasure and nothing else.

"How do you feel?"

"Good." Otis grabbed a pillow and hugged it tightly. He felt a sudden need to wiggle his butt only so that he could show his gratitude and most of all, his satisfaction at how things were progressing. Just like a doggy. The thought made him snicker.

"What? Am I tickling you?" Hudson drawled. "I'm glad that you're entertained, but I feel the need to tell you that being so close to your delectable naked ass is making my dick and balls hurt."

"Oh, no," Otis expressed his concern right away. "What can we do for them to stop the hurting?"

"You could start by telling me what made you giggle like a naughty boy."

Honesty was the only way forward, and Otis had read enough to know that it was absolutely necessary for a relationship to function as it should. So, he readily confessed, "I wanted to wiggle my butt and I thought of how I would look with a tail. A doggy's tail."

Hudson surprised him by slapping his ass playfully. "Do you want a tail? I'll get you one. But you will have to wiggle this sexy butt of yours for me properly once I do that."

"You make me feel so good. I will gladly wiggle my tail for you," Otis promised.

Hudson took a deep breath. "Promise me you'll only be this forward with me. Only me, Otis."

Of course. These were intimate matters. "I promise," he said from the bottom of his heart. He didn't have to lie about such things. With Hudson here, he could be just as he wanted to be. The only thing he didn't understand was why things were taking so long. "Does it always last as long as this?" he asked, curious about all of the intricacies of giving his body away to another man.

"You're a virgin," Hudson explained while he put in another finger.

Otis could feel the stretch now. It was still pleasant, but there was some discomfort. Bits and pieces of his self-education came back to him and he willed himself to relax. After all, Hudson was a man who needed XXL condoms, and that meant that his butt had to adjust itself to that sort of girth. According to the same literature, when done correctly, it would give a lot of pleasure to those involved, and that included the penetrated person.

He would be penetrated. By Hudson's fantastic cock. Such thoughts were so naughty and made him shiver. The stretch of his ass didn't matter as much as long as he focused on the important parts. What would his boyfriend think of him once they got there? What could he do to make it better? At this point, he just lay there, butt up, while Hudson did everything?

If he were good enough, would he become a permanent boyfriend to this handsome man? Sex was essential for a healthy relationship. Good sex. But what if he weren't good enough at sex?

"Does it hurt? I can tell you're tense," Hudson interrupted his train of thought.

Otis breathed out. "Will you still like me if I suck at sex?" That was how people put it so that they didn't sound pretentious, and that was exactly what he wanted, too.

"It's impossible to suck at sex," Hudson said, and he sounded like he knew what he was saying.

"Do you mean, in general, or just me? But you can't know," Otis argued.

He yelped when Hudson slapped his ass again. It was still playful, but it felt like a warning, too.

"Let me be the judge of that. Stop thinking about crazy things, and maybe I'll have a chance to put it in tonight," Hudson said and sounded amused by it all.

Since he was a man who had been in such situations before, it was only normal for him to take things lightly. Still, he felt like pouting a little.

"Have you done this with many men?"

"We're burning through this relationship a bit too fast, sweetie. Don't get jealous now. Just relax. That is, in case you still want it. I can always stop. Just remember that."

"No, please, don't stop," Otis begged. He closed his eyes and relaxed as Hudson continued to move his fingers inside him, slowly making him open up.

Tonight was all that counted. He could make his brain shut up for a while so that he could behave as he should. And they didn't matter anyway, all the men Hudson must have done this with before. Tonight, he was his, and that was the only important thing.

"I'm going to start fucking you now, Otis," Hudson said and moved behind him. "It will feel much bigger than it is at first. Talk to me all the time. Don't bother being polite. I want you to feel amazing."

"Okay," Otis said and took a deep breath.

It did feel big. His first impulse was to pull away, but Hudson held him by the hips and steadied him. If he ran, he would made a bad impression. That was the rational part of him. The rest made him push back a little to meet the considerable girth stretching his apparently tiny asshole.

"You are so beautiful," Hudson said softly. He caressed Otis's back with one hand, still holding him with the other. "Believe me when I tell you that it takes everything I have not to push my cock to the hilt inside you. I want to fuck you so damn much."

That was dirty talking, right? But Otis could tell it was also honest, and it mattered. To be wanted so much. It felt good. He didn't have any other words to express it, and the few he had seemed unable to cover the way he experienced it all inside.

"Please, fuck me then," he said in a low murmur.

"Don't tempt me so much," Hudson growled, but it sounded as if he wanted to do just that.

He could do that. He could provoke Hudson, this experienced older man, into wanting him, and a sense of elation grew inside him as he realized that.

"I want... your cock... deep inside me," he whispered.

"Oh, damn, baby," Hudson scolded him but did so with obvious affection. "Don't hate me for this."

The sudden move made him cry out in surprise. And it did hurt a little and Hudson stopped right away. "How can I do this?" he complained. "I want to relax but--"

"Hush, hush, take it easy. Your body is capable of adjusting," Hudson slowly encouraged him. "I won't move for a bit. You will see that you are getting used to the sensation. Now talk to me. What do you feel?"

"Like I'm so full," Otis explained. "I'm full of you," he said with wonder in his voice. "Yours is really big, Hudson."

"I'm afraid so," Hudson replied.

"Don't apologize. Everyone wants a big cock."

"Otis, stop making me laugh. You're going to make me lose my erection. How is it now? Can I move a bit?"

It took courage to do such things, and Otis was aware of that. He encouraged his lover to continue both through words and by reaching back and grabbing Hudson's hip. Even if the sensation was still a source of discomfort, it was a lot less so, and he could deal with it. At the same time, the stretch was giving way to other things. A couple of times, he could tell that the way Hudson did it made him feel something extremely pleasurable, and he used his voice, as advised, to let the other know.

"I think there was something there," he said, his breath hitching. "You... hit me just right."

"Oh, I'll hit it more than just right," Hudson promised.

It happened again. Otis wanted to shout to express his joy at it. There was nothing wrong with his butt and he could feel all the things he wanted and needed to feel while in a man's arms. Hudson seemed to know what he was thinking because he helped him to an upright position. Then, he caressed his face, turned his head and kissed him, while Otis curved his lower body to meet each movement.

"How is it now, baby? How is your first time getting dicked?" Hudson murmured hotly in his ear.

The sensations were overwhelming, rushing over him in waves. He moved his head as Hudson guided it, just as he did his hips. Another move, another thrust, and the pleasure he experienced was so much, too much, that he had to cry out.

"Do you want me to go slower?" Hudson asked.

They were both sweating, and Otis loved the smell. Hudson sounded a lot less like his usual self, but in such an amazing way. He sounded... like he couldn't control himself, and it made Otis feel so proud that he was the one who was able to make a man with so much experience under his belt -- what a fitting expression -- to lose his head over him.

"Is it me?" he asked for confirmation. His ass was so stretched and full now, but he didn't feel like he was the only one giving something or surrendering. No, he had Hudson where he wanted him to be, and the fact that such a desirable man was there, with him, doing these things with him was all that mattered.

"It's you," Hudson confirmed without asking for any other explanation. "I don't want anyone else."

The answer was deeper than the question, but Otis couldn't keep track of its ramifications because the intensity of the sensations coursing through him kept soaring. And Hudson's right hand dropped from his chest where until now it had played with his nipples to his hard cock. He couldn't recall a thing as he went higher and higher, only to drop from those impossible heights down the slope of absolute delight.

He had done it, he thought, as overwhelming joy drowned him. He had lost his virginity to an amazing man, and crossing things off lists notwithstanding, there was nothing more for him to wish for.

Hudson pushed him down and began slamming into him. His ass, another fantastic aspect of the whole thing in itself, could take it.

"Sorry for using you like this, beautiful, but at this point, I might just go crazy if I stopped," Hudson said through loud moans and groans.

"Use me, please," Otis begged him and cupped his own manhood, elated to feel it so wet and satisfied.

"That is all I can stand," Hudson said and pushed inside him hard and stayed there while Otis could tell, from the sensations inside his ass that something else was happening, something new was happening to him.

He had made it happen, he had made Hudson, who knew so much about dating and sex, come undone.

***

No regrets. As the ebb and flow of sexual release was fading away and he lay there on his bed, Otis's bed, with the beautiful young man catching his own breath beside him, he had expected them to come circling him like dogs sniffing easy prey. Nothing like that was happening. Things demanded by impulse were usually a hard sell with his conscience. And yet, it looked like he experienced nothing like that.

Could it be that he was lying to himself? That he had just offered Otis his first experience of the kind with a man who knew how to appreciate him for his beauty and kind heart? That would have been a convenient lie if it hadn't been for that thing he had let slip out of himself, those words that meant more than he had ever said to any other man he had gone to bed with in his life.