Determined not to be at the werewolf’s mercy anymore, Carlos decided to take the lead. He didn’t know what Wilson had in mind but he stripped his clothes and even used the enema bottle without needing to be told while he showered.

Needless to say, Wilson was pleasantly surprised by the initiative. He thought that he had to go easier on Carlos because of the scare, but the cheetah looked like he was fired up about something. The man even borrowed his enema bottle to prepare himself, even if he didn’t know what Wilson was going to do today.

“Seeing that you’re very eager, shall we begin right away?” he asked.

Carlos smirked. Exactly what he wanted. “Bring it on. What are we doing today?”

A set of bright red ropes appeared, and Carlos suddenly didn’t know if he should continue the tough act. Having his hands unrestrained last night was great. However, when he looked at Wilson’s bandaged hand, he was reminded why Wilson would want to tie him up. 

“You won’t make it hurt too much, right?” the cheetah asked cautiously.

Wilson ran the rope over Carlos’ wrist and looked at him. “How does it feel? Any scratches? Is it too rough?”

Surprisingly, the rope didn’t feel that way, and Carlos shook his head. It looked terrifying, but when Wilson let him touch it, the cheetah realised that it was just irrational fear. So far, the werewolf hadn’t done anything to really harm him. Yes, his bottom might still be throbbing a little from yesterday’s stretching, but it wasn’t unbearable. It wasn’t anything like the beating Carlos received from his own family either. Compared to the treatment he had from ‘home’, Wilson was much kinder.

“Alright,” Carlos agreed. “Don’t cover my mouth.”

Wilson readily agreed. He had no intention to. “If you need me to stop, you know what to do.”

Since Carlos was already naked, there wasn’t much else he had to do. Carlos crawled onto his bed, and Wilson started working on tying his arms to his side together with his knees to keep them apart. It was such an awkward position, and Carlos hated how open everything was to Wilson’s eyes. The inability to move except to squirm like a bug on its back made Carlos slightly nervous, but Wilson kept reassuring him that today’s session wouldn’t be painful.

“If anything, it’s a frustrating and pleasureful kind of pain. We’re going to push your limits tonight, so don’t expect it to be anything as simple as the last two nights. I’m going to work your balls empty by the end of this week. I hope you’re prepared.”

Carlos laughed at that despite his position. “Oh? Is that a challenge?”

Wilson laughed. “No, it’s a promise.”

Carlos didn’t know what to think when Wilson turned on that confidence. It was hella hot, and he felt his lower half react to that. Recalling the first time he challenged Wilson to a stamina competition, Carlos’ entire body heated up at the thought of the overwhelming pleasure. If tonight was going to be anything similar to that mind-blowing experience, Carlos didn’t know how much he could take. Embarrassingly enough, he remembered fainting right after the thing Wilson did after his climax.

Wilson was surprised at just how turned on Carlos already was. He hadn’t started touching Carlos, but already, there was precum at the tip. This was going to be too easy.

With a generous amount of lube in both hands, Wilson started work directly, easing two fingers into Carlos’ rear. The cheetah stiffened at the sudden intrusion but remembered to relax before he got hurt. Strangely, it was easier today compared to last night, even if he was still slightly sore. He didn’t know what Wilson was going to do today, but with his limbs bound so tightly, he was completely at the wolf’s mercy.

Wilson liked how pliant Carlos’ body had become under his touch. Even though Carlos didn’t say it and was quite the opposite in his opinions that came out of his mouth, his body spoke differently.

Carlos groaned when Wilson bit down on his reddened nipple. Even though he continued to apply salve to the sensitive perky tips, it felt as if they were never going to recover with how much Wilson insisted on bullying them.

The werewolf scissored Carlos and spread him as wide as two fingers would go, making Carlos shiver at the feeling of air going into his tight passage. Feeling happy that he took the initiative of cleaning his ass out before Wilson decided to do it himself, Carlos bit back a moan. Wilson’s other hand didn’t lay idle. Instead, it was teasing Carlos’ sensitive tip and tracing the vein on his throbbing underside.

“St-stop!” Carlos gasped when Wilson pumped him furiously and thrust those fingers on that magical place. It was almost too much, and Carlos felt his body convulsing against his will. The rope strained against his sides but didn’t break skin no matter how hard Carlos struggled. Wilson noted how close Carlos was and smirked.

Instead of letting Carlos come, Wilson quickly removed his hands and reached for something, snapping it at the base of Carlos’ manhood. 

Startled by the sudden loss of physical contact, Carlos wondered what was going on until he spotted a black band at the base of his stiff manhood.

“What’s that?” he asked breathlessly, but there was caution in his eyes. It didn’t hurt, but he had a feeling he wasn’t going to like it.

Wilson’s smirk only confirmed his fears. That wasn’t a good look, and Carlos suddenly wanted out of these restraints. It was all a ploy, a ploy that Carlos fell or. Wilson’s niceness was just on the surface. It had to be! The werecat suddenly felt foolish for trusting his watcher. Of course, he wouldn’t truly care for Carlos! Everything was an act just to get him bound and tortured for his sadistic pleasure! Carlos should have seen this coming before he agreed, but it might be too late to turn back.

He could use the safe word, but Carlos wanted to reserve it. Wilson did say he wouldn’t count the times it was used, but Carlos felt that if he abused it carelessly, Wilson would revoke that right. Trust was a two-way street, and it was Carlos’ time to earn Wilson’s trust if he wanted a more harmonious relationship with his watcher in the future. Just because he lost the bet didn’t mean he couldn’t get something out of it.

“It’s a cock ring,” Wilson said simply. “With this on, it’s difficult for you to come. I didn’t choose one that’s too tight, so you won’t get bruised. Told you I would milk you dry tonight. Edging play goes very well with prostate orgasm development. You’re only allowed to come with your ass tonight. If you do it well, I’ll give you a reward as promised until you pass out from pleasure.”

That promise made Carlos’ tail curl in anticipation. His heart never raced faster, and he swallowed hard. A pleasure to take him to that heaven? Carlos didn’t know how much of a wreck his body would be by the end of it, but the nymphomaniac in him couldn’t help but want to find out.

Carlos waited and relaxed when Wilson walked over to his desk to bring something out from inside the drawer. Carlos craned his neck, but it was too far to see, so he gave up. Instead, the werecat closed his eyes and tried to calm down. He could feel the numb throbbing and enthusiasm of his erected lower half even if nobody was stimulating it. The cock ring worked wonders, but Carlos couldn’t help but feel dissatisfied about something - mostly his twitching hole after it was spread so widely apart.

When Wilson returned, Carlos couldn’t see what he was holding, but the werewolf raised those hips and pressed something against his entrance.

It was huge! Carlos wanted to scream, but he remembered Wilson’s advice from yesterday and took deep breaths to relax his muscles. He didn’t want anything to tar, and honestly, he didn’t want to deal with a bleeding behind the next day.

“You’re doing well,” Wilson said to encourage Carlos to continue remaining calm. Even with three fingers, this toy was still slightly too big for Carlos’ virgin ass.

When the toy was almost fully in, Wilson paused. He looked up and noticed that Carlos was covered in sweat, trembling lightly with his fists clenched. The erection was still there, but his nipples were no longer standing erect.

With a gentleness that Carlos never saw out of the bedroom, Wilson wiped the sweat away and distracted the werecat from the toy with kisses. Carlos took every kiss that Wilson gave greedily and slowly. The burning pain in his rear numbed to a dull throb. He didn’t know how much pain he could endure, but he started to get used to it.

When Carlos was relaxed enough, Wilson slowly flicked the switch at the base of the toy. Even at the lowest setting, it still moved a lot, and Carlos almost screamed at the sensation of something vibrating in his ass. Wilson silenced the noisy werecat with a deep kiss while rubbing circles at the tip of Carlos’ erection.

Carlos didn’t know what to do when the huge toy inside kept rubbing against the spot that made him crazy. This was worse than catnip, and Carlos couldn’t control the high pitched mewls. He felt like a kitten all over again, but for a different reason. He’d never felt so dependent on another person, but Wilson had a talent in making him feel like this with his expert control over Carlos’ body. Sometimes, the werecat thought that his watcher might actually know his body better than he did.

The small hole clenched down on the toy intermittently, and Wilson took it as a sign to completely ease the toy into Carlos before switching it to a different setting. He didn’t know how much of this Carlos could take, but Wilson wasn’t going to rush it. It was a good thing he received something to help soundproof this room from Ruo Han yesterday after he helped out with the student community. Still, he wanted Carlos to hold his voice back to heighten the pleasure.

Carlos tugged at the ropes and jerked his hip to fight against the sensation inside of him. It was extremely frustrating how close he was to coming but couldn’t with the cock ring. At the same time, the new setting made the toy inside move at a higher speed for a while before stopping completely. The on and off stimulation was driving him crazy, and Carlos wanted to yell but couldn’t.

Wilson looked for reactions, and the most tell-tale sign of Carlos’ pleasure meter was the werecat’s tail. Currently, it was batting the bed with irritation, and Wilson found that little action extremely endearing.

When Wilson kissed the cheetah’s furry tail, Carlos lost all his anger and swallowed all his irritation back. The small action told Carlos more than words ever will, and he surrendered his body to whatever Wilson was going to do by closing his eyes.

Wilson loved the consent and brought out two very familiar cloth pegs that he didn’t manage to put to full use previously.

“May I?” he asked politely, and Carlos cracked open an eye.

For almost fifteen seconds, Carlos stared at them and didn’t say anything. Wilson didn’t pressure Carlos into accepting. He simply waited as this was not part of their initial deal for tonight’s scene.

“Not too rough,” Carlos finally said and looked away to hide the pink creeping onto his cheeks.

Wilson had never felt prouder of any playmate. Carlos was the first to meet his expectations and exceed them. He kissed the werecat’s tail once more before gently teasing those sensitive nipples into full hardness.

This time, Wilson was careful not to suddenly introduce pain to Carlos. He learned that the cheetah didn’t react to sudden pain very well. It acted as a trigger to something bad from his memories, and the blood frenzy was a sign of trauma.

Carlos didn’t know if it was better for Wilson to be so careful to introduce the pegs to his nipples. Initially, the light pressure was alright. However, at a certain point, he could feel the lactic acid build-up in his body as a reaction to the intensity of pain that only slowly increased without pause. It took almost an eternity for one nipple to be clipped, and Carlos tried to hold back tears. If the cock ring wasn’t where it was, his willy would have shrivelled.

Thankfully, the toy in his ass did what it was meant to do, and Carlos’ brain short-circuited. It didn’t know to process the pleasure or the pain first, so it simply did the obvious and processed everything as stimulation.

Carlos didn’t know when the other nipple was also clamped, but it no longer hurt as much as he thought it did. Actually, maybe it was actually very painful, just like how the toy in him was constantly hitting his insides. However, Carlos didn’t know if he wanted it to stop or if he wanted more. Wilson’s hand wasn’t helping either as he flicked the pegs on his chest occasionally. Carlos felt like he was going crazy from so many things happening to his body as his toes curled and buttcheeks squeezed.

Wilson knew the tell-tale signs of a climax and waited for Carlos to go over the edge. Initially, Carlos’ body tensed like a drawn bow., His stomach went taut, and he pulled at the ropes, but nothing much happened. Then, Carlos shuddered and released a shaky breath followed by heavy gasping as he bucked his hips with eyes rolling to the back of his head.

A dry orgasm? Wilson’s mouth went dry. This was the second dry orgasm immediately after the first. Carlos was truly a gem, and Wilson felt lucky to find it in the playboy everyone called a disgrace of an alpha. Such sensitivity was a talent.

Carlos didn’t know what was happening. His body was on fire. His mind was mush. He no longer knew pain from pleasure, right from wrong. All he knew was how this wasn’t enough.

Wilson heard what Carlos couldn’t say through his body and turned the switch to the maximum. By now, mini Carlos was rock hard and ready to erupt at any moment, so Wilson decided to give it a hand by pressing the vibrator against that one good spot.

Carlos screamed as he came hard, jerking his hips violently. The struggling caused the pegs on his nipples to sway violently, contributing to the cycle of constant stimulation to the overly stimulated body. Wilson had to step in and hold Carlos down so that he wouldn’t hurt himself.

The line between pain and pleasure faded so completely that Carlos cried from the sensation. He’d never felt more alive than now, and Wilson made good of his word to milk him dry.

The cock ring came off the moment Carlos built up enough pressure to shoot his load despite the tight pressure on his cock. It looked so angry that Wilson took pity and released it from its confines.

The moment the dreaded rubber ring came off, it was like a floodgate of cum that simply wouldn’t stop, not that Wilson wanted it to. The werewolf pumped Carlos harshly with a speed that would normally hurt, but Carlos was too far off the edge that it only felt good. His balls contracted further and squeezed every last drop of white it could.

Shuddering from the intense high, Carlos thought it would be over. However, Wilson didn’t allow it. There was still more come from where that came from. The night was still young, so he pulled the wooden pegs of Carlos’ sensitive nipples.

Carlos screamed when they came off so suddenly. The pain only added to his sensitive state, and he didn’t know if the new sensation was good or bad when Wilson sucked on the swollen tips.

Wilson never stopped moving his other hand, pressing against Carlos’ slit and even digging a nail into the tortured mushroom head occasionally. Carlos cried and begged, but Wilson didn’t listen. As long as it wasn’t the safe word, he wouldn’t stop.

In the end, Carlos could only lie there and receive what Wilson gave. The toy didn’t stop vibrating, and Carlos could feel the next load coming at the way his balls twitched. There was still come left after that explosive release?

Wilson wasn’t wrong about how Carlos could still come when a second heavy load came. It wasn’t as powerful as the first load, but it was still thick enough to convince Wilson that Carlos still had more.

This time, Wilson used his mouth for something other than sucking on Carlos’ nipples. For a moment, Carlos was glad his tortured tits were finally given time out. However, he threw his back in a silent scream when strong hands locked his hips down. Wilson took him into his mouth in one move without gagging, and Carlos thrashed his head, not knowing why Wilson’s blowjob felt like nothing he was familiar with.

Wilson didn’t just swallow Carlos whole. He teased the tip and sensitive limp underside carefully to work it into semi hardness again within seconds. Carlos cried and begged beautifully, and Wilson felt the front of his underwear becoming damp. Oh, how he wished he was inside of this beautiful person instead of that electronic toy.

Carlos trembled bonelessly after a while. The fight fled him, and his brain refused to understand anymore. It simply started accepting what it was given even if the blowjob was merciless, trying to suck the impossible third load from him. Carlos shivered, and his eyes rolled to the back of his head several times as he tried to remain conscious. Each time he felt like he would faint, Wilson’s talented mouth would pull him back to his body to experience the excruciating pain from overwhelming pleasure.

Wilson wasn’t completely prepared when Carlos released his third load. The cheetah wasn’t even fully hard when that happened, but it was a lot more watery than the first two times. If he was lucky, he might be able to coax the poor thing to a fourth climax tonight.

However, there was a problem. Carlos no longer struggled, and Wilson looked up. The werecat had gone past his limits, and his body decided to shut down after that third time. Seeing that it would be useless to wake Carlos up now, Wilson unbuckled his pants, and his member sprung forth like a beast eager to devour. 

Taking in the debauched sight before him, Wilson bit the edge of his shirt and masturbated quickly to the sight, smell and sound of Carlos’ climax replaying in his head. The image was so powerful that Wilson came undone within minutes, something that usually doesn’t happen.

After coming down from his high, Wilson switched the toy off and removed it gently. He needed to rest before he cleaned up and took care of those rope burns for Carlos. Now that it was finally over, he checked the time.

The play lasted almost an hour, and Wilson could hardly believe that Carlos was a beginner. It took almost an hour to break Carlos down, something that took less than half the time for newbies. His tolerance was very high, and Wilson carefully brushed the stray hair from Carlos’ face, admiring his peaceful expression as he slept.

Without saying another word, he placed butterfly kisses over the sleeping man’s eyelids and smiled. What a beautiful person, he thought and kissed those damp blonde locks.