Perfectly Pegged
A new story for a brand new prompt! This week's prompt being "If you want it done right..."
New story out, finally, featuring my two characters Damian and Serena, from previous stories. If you want, you can check them out in my gallery!
For this one, Damian has accepted a challenge from his kinky girlfriend, one that has left him less than perfectly rational in his thinking. Desperate for some relief, the jackal goes through some of his girlfriend's things in an attempt for some relief. What he finds isn't exactly what he's hoping for, but he decides it'll do. However, in the midst of some sought after pleasure, the canine gets caught red-handed by Serena, who decides it's time for her to demonstrate some of her skills on her ever horny boyfriend...
That's all I have to say for now, so please, leave a like or a comment, and enjoy the story!
When Damian had agreed to what his girlfriend had suggested to him, he didn’t think it would make him feel this… off-kilter. Namely, that he would be feeling so incredibly horny when he’d never felt like such before, that he could remember at least.
The reason for his current situation?
Serena had gotten him to wear a chastity cage, and challenged him to go a month with it on, on top of not being able to cum. He hadn’t thought much of it at the time, and honestly, he had felt a bit curious about the experience it could provide, as well as how it might spice up their relationship. Now, he had his answer, and he wasn’t sure if it was really the best sort.
Currently, the jackal was in Serena’s apartment (part of an agreement they had where they’d visit and stay at each other’s over the weekend), and he was trying to find where his dom of a girlfriend had possibly stashed the keys to his cage. Nearly 2 straight weeks of chastity, after years of having the freedom to get off whenever he wanted, had made him desperate, enough that he was now sneaking around his girlfriend’s bedside drawers, never mind he might have possibly been invading Serena’s privacy; he simply wanted to get off, and he wanted it now.
Unfortunately for Damian, he hadn’t found any keys that looked like they fit in his cage’s lock. However, he did find something just as embarrassing.
He found a collection of sex toys in one of the snow leopard’s drawers. Initially, the jackal had slammed the drawer shut, his face blushing furiously, before quickly moving on to something else. However, after all that time spent fruitlessly searching for the cage keys, Damian was now incredibly frustrated, which wasn’t helping his desperation and horniness.
In the midst of his hormonally clouded mind, the jackal happened to glance back at the drawer of sex toys… and began to seriously consider using them. He shook his head at that. No way was he going to use his girlfriend’s sex toys to try and get off, even with the cage on. It just didn’t feel right.
Several more minutes later, with nothing turning up, however, and Damian was rapidly changing his mind on the initial stance he’d had.
Checking around the place to make sure he was the only one around, the jackal quickly stripped off all of his clothes, before opening the drawer again. Grabbing a dildo he felt was the best to use, as well as a bottle of lube (strange, he didn’t think Serena would need to use lube with these toys, but he wasn’t complaining).
Climbing into the bed, he made sure to pour a generous amount of lube onto the dildo he was about to literally shove up his ass. He’d never tried anything anal before, not even fingering himself, but he supposed now was as good a time as any to experiment, as well as see whether the small amount of internet knowledge he’d gained about the subject would be useful now that he was about to do it for real.
Lying on his back, his legs raised high, Damian slowly eased the well-lubed toy into his virgin asshole. It was understandably tight, the toy stalling soon after the tip began entering, and it stung a little. However, Damian, horny as he was, ignored it, and began to push it in with slightly more force, before his hole finally began to slowly give way.
Gradually, eventually, Damian had gotten the toy all the way in. For several minutes, the jackal laid there, adjusting to the feel of having a phallic-shaped piece of silicone all the way in his rectum. It… felt a bit weird, but it wasn’t unpleasant, especially after giving it some time to settle in.
Finally, when Damian had determined it was as good as it was going to get, he began to pull and push the toy in and out, slowly at first, before speeding up as his asshole began to get used to the sensation of the toy moving in and out.
Over time, he started to actually enjoy the sensation of thrusting in and out of himself, the way the toy hit a certain part within him, he began to speed up his pace even more in a bid to gain more pleasure out of it, his locked nub twitching up and down in arousal. Somehow, though, it didn’t feel like it was as good as it was supposed, and Damian endeavoured to fish that, trying to achieve that little bit more pleasure, trying to get the most of the toy, to get past the chastity cage that kept his cock so confined.
In fact, it was this haze that kept him from hearing the sound of the door to the apartment opening and closing, and by the time the door to the bedroom swung open, it was far too late for Damian to hide what he was doing from the snow leopard that had entered.
“S-Serena!” Damian yelped when he saw his girlfriend in the doorway. “I- I can explain-”
“My, my,” Serena purred, “someone’s been looking through my stuff.”
Damian sputtered, thinking he was about to face a mad feline, but Serena went on, “I didn’t think you were into that sort of thing, babe…”
Damian blushed and tried to stutter out a response, but the snow leopard didn’t let him finish as she continued, “And look at your positioning there; that’s not how you do that and feel really good.”
The jackal swallowed and asked, “What do you mean?”
Serena gave him a sultry smile, replying, “Why don’t I show you?”
Not seeing much of an alternative (and not wanting to potentially get on her bad side after getting caught red handed), Damian nodded.
“First, I think you have to change that toy out for a different one; I know of a perfect one.”
The jackal complied with his girlfriend’s instruction, fully pulling the dildo out of his hole, gasping a little at the emptiness it left behind and the sensation of his tailhole winking after the toy.
“Good boy.”
The canine whimpered hornily at that, his tail wagging on the bed.
“Now, get on all fours.”
Damian turned to flip himself over, making sure to keep his tail raised up toward Serena. His legs felt a little numb from the position they’d held for a while, but it wasn’t anything he couldn’t handle, and he managed to get into position.
“Very good,” the feline said. “Now then…”
After a minute or two of shuffling sounds from behind him, Damian unexpectedly found a piece of cloth being wrapped around his eyes, blindfolding him.
“You just stay right here, sweetie,” Serena purred into his ear, “I’ve got a surprise for you.”
The way she said that made Damian excited, his tail wagging more in response as his girlfriend went to prepare the “surprise” she said she had for him.
He waited there, on the bed, as he heard the sound of drawers being opened, as well as the slight rustle of cloth, the anticipation building up, waiting to find out what his girlfriend had in store for him.
The first thing he felt was the sensation of someone getting onto the bed with him, then of cold lube being poured onto his tailhole. He stiffened up a little, but his girlfriend quickly soothed him with a purr, calming him down from the shock.
Next, he felt the tip of something that did feel vaguely phallic press against his entrance, causing Damian to tilt his head slightly toward where he assumed Serena to be.
“I did say you were doing it wrong,” Serena chuckled. “Now, I’m going to show you how it’s properly done.”
With that statement, the snow leopard promptly grabbed the base of his tail and began to push the new dildo into Damian’s already loosened hole, giving her an easier time of penetrating him than Damian himself had had only several minutes before.
The jackal sucked in a surprised breath, not really expecting his girlfriend to make a move like that, but there wasn’t much he could do with Serena’s grip on him but to stay as still as possible and take it.
And take it he did, even though the toy Serena was using felt noticeably bigger than the one he’d been using before. He stayed as still as he could and let his girlfriend push the new toy into his hole, right up until Damian felt himself get hilted by the dildo, gasping out loud as he bottomed out and shaking at the intense sensation it gave him.
“Good boy,” the snow leopard purred again, “Need a minute or two?”
Breathless from fully taking in the toy, the jackal nodded, and Serena thankfully left him some time to readjust his body around what she’d pegged him with, letting him prepare for the rest of whatever she had in store for him.
A few minutes later, and Serena leaned in close to him, asking, “You ready for the rest, babe?”
“Y-yes.”
“Better hold on, then,” the feline purred, “I’m gonna make very good use out of your sweet boy pussy.”
Without warning, Serena began thrusting in and out, continuously, pistoning the dildo with a pace that was gradually getting faster and that was leaving Damian’s body very shaky from the impacts it made with that sweet spot in him, his caged cock twitching and dripping precum from all the stimulation.
“F-fuck, ohmygod, fuck,” the jackal panted breathlessly.
“Feel good, boy toy?” Serena seductively asked into his ear.
The only response Damian could give was a garbled series of swears and panting, which Serena seemed to take as a positive answer to start speeding up her fucking of him even more.
Meanwhile, the canine’s arms had given out beneath him, leaving him hugging a pillow and biting into it to try and suppress the loud moans and whimpers that were raring to come out of him, while his hips bore the brunt of Serena’s thrusting, the force behind it enough to send slapping sounds throughout the room.
Out of the blue, the feline grabbed Damian by the shoulder and pulled him from the pillow he was muffling himself with, Serena making sure to pull him in extra close, such that he was now kneeling up as she spoke into his ear again, “No need to keep quiet, you know; it’s just the two of us here, after all.
“I want to hear you moan my name, puppy.”
With that, she kept Damian in place by placing her arm across his chest as she pounded his tailhole with more vigour.
Without the pillow to gag himself with, Damian let out his moans, and just like she’d asked, cried out Serena’s name over and over again, especially when she hit his sweet spot, which seemed to satisfy her from the increased purring he felt.
It was… almost overwhelming, how it all felt, and yet, Damian couldn’t help but enjoy it and crave it, cries of “Yes!”, “Right there!” and “Ohhh, fuck!” reverberating throughout the room as they were blurted out by the canine entrapped in the throes of pleasure, his chastity cage always bouncing up and down while ropes of clear fluid leaked out from the end of it onto the sheets below, creating an ever expanding dark spot on the bed, one that didn’t escape the snow leopard’s notice.
“Look at how much you’re leaking,” she said, sultry, as she reached down and began to tease and fondle his trapped cock and balls, running her hand gently over both the metal bars and the skin on his full testicles, making Damian gasp and whimper as his genitals reacted, throbbing and twitching, trying to get more of that stimulation that they so desperately wanted, but couldn’t reach through the impregnable steel bars of the chastity cage.
Serena ran a finger up his leaky head, rubbing it against the slick and highly sensitive hole, making Damian shudder and almost sob with unadulterated need, even causing him to thrust against her hand, with no success as the snow leopard almost immediately pulled her precum-covered hand away, before pressing her slick fingers against his lips.
“Look at how wet you are,” she cooed, coaxing Damian to taste all the precum on her fingers, “moaning and whining, so needy, so horny… all from me pegging you. And since you like it so much…
I’m definitely going to be doing this more often with you,” she giggled.
Damian couldn’t really say anything back, so addled his brain was from the fucking and teasing his girlfriend was putting him through. She only chuckled and kissed him before resuming her thrusting, this time also making sure to use one of her hands to alternate between jiggling his cage around and playing with his nipples, now hardened and sensitive with arousal.
Between the stimulation from Serena fucking him in the ass with a dildo, and fucking him really well with it, and her hand relentlessly teasing his chastity cage and nipples, it wasn’t all that long before Damian felt what seemed to be an orgasm coming on, even with his cage offsetting a lot of the pleasure he was feeling.
“Fuck, Serena,” he said, panting, “I- I’m- I think I’m gonna-”
Damian didn’t even get to finish before Serena had completely pulled out, depriving him of the pleasure he wanted, needed, and he whined and whimpered helplessly as the orgasm that had been building in him receded, leaving him now both empty and frustrated.
“Ooooh, that was fun,” sighed Serena, smirking as she listened to Damian hornily keen. “I did say it was for a month, didn’t I? Can’t have you cumming too early.”
Damian only whimpered some more in response.
“Ah well,” she continued, “I suppose I can give you some reward. Here–”
She let go of him, letting him fall onto the bed, before flipping him onto his back, then reaching over and taking off Damian’s blindfold.
Blinking for a few moments, the jackal couldn’t help but stare at the strap-on dildo Serena was packing; it was definitely bigger than the toy he’d used on himself, and it was dripping with all the lube the snow leopard must have poured on it to get it to slide in as smoothly as possible. Damian was pretty sure his mouth was slightly agape as he took in the beast his girlfriend had fucked him with.
Serena only giggled at his reaction, “Impressed, huh? Been wanting to do that with you for a while, not gonna lie. Thought it’d be just a fantasy of mine… then I walk in on you giving yourself the anal treatment.”
The canine blushed at the way she worded that, but his tail wagged nonetheless.
“We’ll have to try that again sometime, once you’re free to cum, of course. You certainly seemed to enjoy it, didn’t you?”
Damian nodded sheepishly. “Y-yeah, I really did…”
“That’s what I got from how you were howling all the way there,” Serena smirked, seeing Damian’s tail wag even as more embarrassment swept across his features.
“H-how are you that good at that though?” Damian couldn’t help but ask her.
Serena chuckled and said, “Let’s just say… a few of my exes were quite into that sort of thing, so I decided I was going to get as good at it as I could.”
The jackal blinked. “Wow, I… did not think those guys would be into that.”
“Yeah,” Serena agreed, “just goes to show what kind of person can come out in the bedroom, eh?” She smirked down at Damian blushing at the subtle reference she gave him of what she’d seen him get up to.
“Enough talk, though,” the snow leopard thankfully went on, “let’s get you that treat I was telling you about.”
Taking off the strap-on and dropping it off on the side of the bed, Serena moved her hips over Damian’s face, the jackal now seeing how wet her pussy was in very close detail.
“I know how much you love eating me out, babe,” the feline purred, “so, here’s your treat. Have as much as you want.”
She lowered herself onto Damian’s mouth, and the jackal faithfully and enthusiastically began lapping at her folds, fuelled by his denied orgasm and the pent-up lust still coursing through him.
After who knew how many orgasms, Serena finally decided she’d gotten enough and lay down next to Damian, reaching around and cuddling him, the jackal leaning into it as a response, the feline’s purrs reverberating through his body.
“So…” Serena started, “think we should try that more often?”
Damian considered it quietly for a few moments, before saying, “Yeah, I wouldn’t mind that at all…”
“That’s good to hear,” she said to him, “because I still have quite a lot to show you when it comes to that sort of thing.”
Laughing lightly at the canine’s new expression, a mix of anticipation and apprehension, Serena smiled at him, leaned in and lifted his chin with a finger, before purring, “If you want something done right, babe…”
Damian shuddered at her seductive voice, and the promises it held for him in the future. It seemed that Serena certainly had a lot of things to teach him, more than she’d had before… and they were lessons that Damian was very much excited for.
His tail wagging again, he fixed his eyes on hers and said firmly, “I can’t wait to learn from you.”
Serena smiled and purred once more, “Good boy…”