CHAPTER 385: LOOSEN UP [M]

"Uh!" Feeling the lube-covered finger slide inside his hole, Lane couldn’t help but let out a muted groan.

Damien immediately paused. "Sorry, does it hurt?"

"No, it’s not that..." Lane muttered in response. "You... can go on."

It truly didn’t hurt. It was just one finger, after all. It just... felt odd. A little bit different kind of odd than when he had tried to prepare himself earlier in the shower. Perhaps because he was all warmed up already, with the foreplay and the blowjob that Damien had just given him, which made him more sensitive, or perhaps because Damien pushed his finger a little bit deeper... Or maybe just because it was Damien’s finger and not his own. Just as masturbating and having someone else rub you off felt different, even though the action was essentially the same, only that done with different hands, preparing yourself and being prepared by someone else were also different. Not having to do anything himself other than lie back and try to enjoy himself, Lane could fully focus on the sensation...

But that also came with some problems.

"...You need to try to relax and loosen up a bit," Damien said after a while. A few minutes had passed, and despite his efforts in massaging Lane’s hole, it was still so tight that Damien couldn’t push the second finger in. Lane’s rectum was clammed around his middle finger, as if he wanted to trap him inside forever.

"Uh... I know..." Lane muttered. He WAS trying, alright? And it’s not like Damien was even doing a bad job... Quite the opposite, in fact, he was surprisingly good. Perhaps because he had had Lane do that to him so many times, he had learned well.

Lane was kind of proud. It was he who had taught Damien everything the man knew, after all!

But feeling proud and being able to loosen up were two different things. Lane was an indisputable top, it was only natural that his ass wasn’t particularly welcoming to any attempts of penetration, no?

"Ah!"

Just then, Damien’s finger stroked against Lane’s prostate, resulting in a loud gasp escaping Lane’s throat... And in his rectum squeezing even tighter than before.

It was pleasurable, but also unfamiliar and odd, different from the sensations that Lane had experienced during any of his previous sexual endeavors! He couldn’t help but tense up, his thighs clamping Damien’s torso from both sides.

It seemed that Damien had a long way ahead of him, before he could get Lane ready for penetration.

Luckily, he was an endlessly patient person. Although Lane wasn’t exactly cooperating (unintentionally, of course. It was hard for most people to control their physiological responses), he didn’t seem to be in pain, and hadn’t told Damien to stop, so Damien carried on, carefully moving his finger in circles, massaging Lane’s entrance. And, eventually, his patience paid off, because he managed to make enough space for the second finger. It took far longer than either of them had expected, but at least there was progress. After a while, Damien had been able to add the third finger, then the fourth...

"Ugh," Lane groaned, grasping onto the sheets, and causing Damien to pause again.

"Everything alright?"

"Uh, yeah..."

Despite Lane’s words, he didn’t quite look as if everything was ’alright’. His fingers were crumpling the sheets so much that it seemed like Damien would have to iron them at least three times to make them smooth and wrinkle-free again, and he was staring at the ceiling with his eyes open so wide that they were almost falling out of their sockets, his expression queasy...

Damien hesitated once again. They were at the four fingers now, which meant that they were almost done prepping. That’s about as much as Lane usually did for Damien, and since they were about the same size, as they had established a few moments ago, it should be enough for Lane as well. Lane’s body was about as ready as it could be...

But was his mind ready as well? Damien was not so sure...

"Ugh... Why did you stop?" Feeling that Damien’s fingers stopped moving inside his hole, Lane lifted his head, trying to fix his expression as he glanced at Damien. It didn’t work all that well, as he still looked uncertain, but at least he no longer looked so terrified.

No matter what facial expression he forced on right now, though, Damien knew what he had seen. Lane was afraid, or at least very anxious, he was sure of it.

"Lane, you..." he started reluctantly, but then paused.

He wasn’t confident. He was uncertain, both about himself, about what he was about to do, and whether he could make Lane enjoy it. He wasn’t sure whether it was truly a good idea, even though he wanted to give it a try.

But at the same time... Lane wasn’t the kind of person who would do something he truly didn’t feel like doing. Although he had gotten a lot better since they had first met, trying to be a bit more considerate of others (at least sometimes), he was still selfish in many aspects, and that was a fact. If he offered himself to Damien, then he must have thought it through, and perhaps he was even curious about it himself. So, if Damien continued to act so indecisive, wouldn’t that be more frustrating to him?

"Hmm? What is it?" Lane lifted his brows, trying to act casual, even though his hands were still tightened on the sheets, his breathing uneven and shallow.

Damien hesitated just for a moment longer, but eventually, he asked, "How do you feel? Ready to... take things further?"

"Y-yeah. I was ready a long time ago!" Lane forced out a chuckle, clearly bluffing. "Just go straight for it, there’s no need for you to be so careful with me! It might be my first time bottoming, but I’m not a virgin! Besides, I’m an SS-rank Esper, I can take it!"

Well, that was true. As a high-ranking Esper, Lane had pain tolerance incomparably higher than a regular person. And his recovery speed was also off the charts, so even if he got hurt in the process, he would be fine by the morning... Not to mention, Damien had prepared him well, so it shouldn’t even hurt too much.

It also seemed like he was being honest, with the ’go straight for it’ part. Perhaps it truly would be easier for him, to just take it in, and then adjust?

Damien took a deep breath...

Then, he pulled his fingers out from Lane’s hole, grabbed his boyfriend by the waist, and with one swift move, he flipped his boyfriend to the other side.

The red ribbon fluttered in the air, tangling Lane and Damien up. Because it hadn’t been fully removed, it still hung loosely around Lane’s legs, so when Damien flipped him onto his stomach, it wrapped both of them together. But it was fine - it was loose anyway, so it didn’t get in the way. It shouldn’t. Damien didn’t pay much attention to it anyway, just brushed it aside, as he grabbed the tube of lube lying on the side, and squirted a generous amount onto his hand, applying it to his cock with a one swift move.

The truth was, he was barely holding on. He had been for a while now. Although he had been massaging Lane’s rectum with seemingly endless patience, deep down, he was growing restless. His cock had been hard and throbbing all this time, demanding to be satisfied, but he didn’t want to rub it off, since if he had climaxed, he would have to wait until he got hard again, and he wanted to be ready whenever Lane was...

But it was hard. With Lane’s naked, flushed body in front of him, and with his gasps and groans reaching his ears, how could he not feel lustful? He might have been prudent, but he was still a man in his prime, with healthy libido!

Kneeling on the bed, he grabbed Lane’s hips, and pulled him up, until Lane was on his all fours. That was one of the positions Lane had used when they had penetrative sex for the first time, back at the summit, so it should be alright to use it now, right?

"H-huh?" It took a moment for Lane to realize what was going on. Doggy style was indeed a great position...

But it was not for the beginners, since it put the top in complete control! It was one thing when Lane had used it during their first time, since Lane had already had plenty of experience as a top, so he had known exactly what he was doing, but for Damien... That might not be the best position to start with! Lane was thinking more along the lines of the cowboy position, or maybe the missionary, which, although also top-dominant, would give him more options to adjust, by for example rolling over...

"W-wait..." he wanted to speak up, but it was already too late. Damien had listened to what he had said a moment ago... And after positioning himself, plunged straight into his ass.