Dating Rules And Pretty Fools Ch. 18

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.

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