Sponsored - Featuring: Demi Lovato

Sadly though, her efforts were all in vain. Demi was incredible, there was no doubt about that. Her oral skills were top-notch, at least in terms of giving a traditional blowjob. But, it was going to take more than that if she wanted me to blow my load. She was desperate, and no amount of "confidence" in the world was going to be enough to stop me. Not when I knew eventually she'd go even further and allow me to fuck her.

My nerves were beginning to settle, but Miss Lovato did her damnedest to try and maximize my pleasure. As time passed and it became increasingly obvious that I was starting to fight against her, Demi began to accept more and more of my length into her mouth and down her windpipe. Inch after inch disappeared into the dark vacuum below me, with the pleasure I received increasing the farther she went. But as talented as she was, Demi had her limits.

Not that I saw, my eyes were completely closed, but a long, guttural coughing and gagging fit assured me that she'd taken everything she could. I could feel her, hacking around my shaft and I knew Demi had only managed about half of my dick down her throat. Always undeterred, she bobbed back down, wasting no time getting back to her previous high.

This time, Demi managed an extra inch or so, but by now I was fully erect. Miss Lovato was struggling with just over half of my length, with an entire half still to go. Again, she tried her best and held it as long as possible. But eventually, she had no choice but to come up for air.

Tears dripping from her now bloodshot eyes and saliva coating the rim of her mouth, Demi took a deep breath before going back down again, all in the name of victory. For a moment, I was impressed by both her willingness to do anything to finish me off and her inability to realize that she'd never be able to take that much cock down her little throat. But she tried again, nonetheless.

Back down she went, swallowing another six or seven inches of my member, with this attempt ending the same as the others. Cough, cough, gag, cough, gag, spit out. She failed but remained undeterred. I finally worked up the courage to look down at her, to catch a glimpse of the pop star's eager face. But before I could, she'd re-swallowed my cock again, sending me back into the cage. Again she failed, but this process was repeated over and over again until she finally gave up after what surely had to be the tenth time, at least.

Though she may have given up on her deep-throat dreams, Demi hadn't gotten desperate enough to take things a step further, though. She was still certain that her talented little mouth would be enough to finish me off. So, since she couldn't seem to manage my entire length, she merely worked the inches that she could, showing off her skills by using her mouth to entice some and her hands to work on the rest. It wasn't how she had hoped, but Demi was finally working my entire shaft, all at once. And boy, did it feel amazing!

Especially her mouth; she was finally sucking my cock properly, after several minutes of failed deepthroat attempts. Her warm money-maker was sucking me in like a black-hole, with her hands gripping tightly at my base. Every inch of my cock was receiving top-tier pampering and yet, it still wasn't enough to make me cum. I'd gone way too far to turn back now. If Demi was as serious as she claimed to be, then she'd be giving up her pop star pussy any second now.

Well, at least that's what I thought. Miss Lovato remained persistent, if nothing else, even going as far as to ramp up the pressure of her blowjob by using faster, sharper mouth movements. Her teeth dropped just low enough to get involved without getting TOO involved, and her wet, slimy tongue was so infatuated with my dick since it never seemed to stop moving. Her tongue was probably her most dangerous weapon yet. No doubt she was putting one-hundred percent of her energy into

That little devil was perennially servicing, practically worshipping my cock. Where her mouth went, her tongue followed behind, proving to be the key factor in Demi's dick-sucking confidence. The former Disney star knew how to work a cock, that's for sure. Which only made me think about how many Hollywood guys had received the rigorous "Sorry Not Sorry" treatment like I currently was.

For the first real-time since we'd begun, I was forced to enhance my efforts; not blowing my load was becoming increasingly difficult. Taking a deep breath, I closed my eyes, trying my best to block out the intense pleasure. But Demi had long since proven to be far more skilled in this regard than she was at fighting. She may have been average throughout our spar, but Demi had proven herself to be a cock-sucking superstar! Sweat poured down from my forehead; the Woke Warrior had me right where she wanted. But just when it seemed I'd reached my boiling point, Miss Lovato gave in.

Removing her talented little mouth from my shaft, she complimented, "Y-you've hung on surprisingly well, for a rookie anyway. I...can't believe I'm about to do this!" Her face was flushed; she seemed embarrassed, even though she'd just spent the last however many minutes sucking me off. Nevertheless, Demi stood up and took my hand into hers. Then, she dragged me over to the middle of the octagon and threw me down. Damn, she was giving it her all!

Demi made a real show out of her approach, going ever so slowly as to allow me to take in her excellent body. Her big natural breasts and perfect, well-rounded Latin booty were to die for, and she knew it. "So, rook, tell me something. Before we go all out, I need to know, what do you think of my body? Huh? Don't just sit there, answer me!"

Stumbling over my words as she drew closer, I struggled to answer the feisty goddess coming towards me. "Cat got your tongue? Not so badass now, huh?" Demi joked while slowly removing her top, allowing her ridiculously gorgeous tits to flop out. Two wonderful handfuls of caramel deliciousness, only enhanced by the sweaty glazing that coated them. If she was deliberately trying to choke me up, it was working.

"Aww, still giving Miss Lovato the silent treatment? C'mon big guy, tell me! What makes you tick.... oh, I know!" As she crept closer and closer, Demi decided to take her erotic arrival in a different direction. She turned around, her backside facing front. As she slowly bent over, she took the sides of her tight-fitting workout shorts into her hands and asked, "You like big, round butts don't you, Shane?" I gulped, she knew my weakness.

That juicy booty of hers had always been the apple of my eye. Nothing could ever compare. The shape, the size, the color, everything about it was perfect. If there was anything that could make me cum for sure, it was probably Demi Lovato's delicious bum.

"Yeah, you guys are all the same. Always fawning over my booty, it's shameful! But, I can tell it's working," she assured, delivering a few smacks to those round mounds on the way up. "Oooh yeah, go ahead, rook, tell me how much my big, fat ass turns you on! I wanna hear it before it makes you cum!" I wasn't entirely sure what she was suggesting. Was she going to let me fuck her ass? Or, did she just plan on riding me, giving me the perfect view to stare at that work of art?

"Hello? Shane? I wasn't joking around! Tell me! Tell Miss Lovato how much you love her ass!" I'd been too shocked to speak with her throughout this whole thing. But I didn't have much of a choice now. She wanted to hear my opinion, so I told her the truth.

"I-I...love it. It's beautiful," I shyly responded as she grinned slyly.

"Mmm- I thought so," Demi purred as she began to mount me. Foolishly I tried to raise my upper body, but Demi quickly pushed me back down, reminding me that she was in control. If and when I came, she wanted my involvement to be as minimal as possible, to ensure that she'd received the bulk of the glory for having made it happen. To ensure that she was declared the winner.

Still unsure of why Demi was so persistent in her attempts, I stayed relatively still, only slightly peering up to see that famously thick behind of hers hovering over my cock. That booty jiggled like Jell-O from even the slightest movement, including when she reached down to position my python, lining it up with her pop star pussy. One swift entry later, and I'd officially become one with the worldwide sensation.

My future sponsor couldn't help but moan and even wince from the intensity. Never before had she forced something so massive inside of her surprisingly tiny chute, a fact I could tell by her tightness alone. Demi struggled to manage my length and girth, taking her sweet time slamming her ass down as proof. Much like her throat, her snatch could use some more practice.

As an outsider looking in, I would've assumed that someone as sexy as Demi would've been a prime target for most Hollywood guys, and even some Hollywood girls too. But apparently, her bad-girl reputation didn't live up here; she felt just as tight as a virgin. Obviously, she wasn't, but it remained to be seen just how sexually active she's been in the past.

Nevertheless, after several minutes of agonizingly slow sliding down, Demi's meaty ass cheeks finally brushed against my muscular thighs, meaning she'd impressively managed to fit all of my shaft inside her taut hole. She dug her sharp claws into the skin of her thighs, overwhelmed by a combination of sheer pleasure and intense pressure. Even still, the sassy superstar had the gall to run her mouth.

"Mmm- ya...ooooh! Ya gonna cum, rook? Yeah, I knew you couldn't handle me!" Demi struggled to ask. Honestly, she felt fantastic! Her pussy was so warm and inviting once she'd settled down. But, it was obvious to anyone with a pulse that she was enjoying me, more than vice versa.

Sure, getting to fuck, or rather be fucked by, Demi Lovato, of all people, was a once-in-a-lifetime experience. Something I'd never forget for the rest of my days. But, as special as her pussy was, my dick seemed to be life-changing to the Mexican musician. Demi's jaw had dropped the moment I entered her, and it had hardly repositioned since. She was lost in a perpetual state of bliss, unable to process the copious amount of cock she was consistently receiving.

The irony was, the harder she tried to make me cum, the closer she got to making herself cum. Vigorously slamming that fat ass down, her meaty cheeks emitting a thunderous clap that echoed throughout the otherwise empty room. Upwards of twelve inches of pure masculinity barreling throughout her sopping-wet cunt.

Demi knew how to work a shaft well; reverse cowgirl was definitely her position because she rode like a pro. In all honesty, watching her butt quake definitely had me on the brink of orgasm, and who could blame me either? Her tight pussy jerking my shaft, mixed with the stunning visual of her big, round booty shaking around my waist made staying strong nearly impossible. But, I managed powered by the lone thought that maybe, just maybe, that Demi would take things one step further. That, hopefully, Miss Lovato would get desperate enough to let me inside her forbidden hole.

Sure, it was a stretch. But there was no way I could cum now and risk never finding out. I was certain that if she didn't want to promote me, that getting to fuck that fabulous ass wasn't out of the realm of possibility. And the only way to find out was to outlast her.

Still, a daunting task, especially when she started to grind those massive lumps each time she finished a rotation. I was getting closer; surely she could feel my cock pulsating inside of her pussy. I'm certain she could, which was why shortly thereafter, she finally allowed me some involvement, albeit the relatively minor kind.

"God! Oooh- OOOOH! Go ahead, Shane! Smack my ass! C'mon, give your favorite booty a few love taps! Do it NOW!" Demi demanded, simultaneously holding her ass down and swallowing the entirety of my dick with her hungry snatch. Technically, I never told her that her butt was my favorite. But, since her assumption was correct, I decided to adhere to her demand. Raising my hand, I hovered over each of her delicious caramel-colored cheeks before landing on the right one, bringing my open palm down with as much force as possible.

"Oww...Again!" She yelped, finding an abundance of pleasure in an otherwise painful experience. Who was I to deny a lady of Demi's caliber? Doing as told, I brought my hand down again, this time showing some love to the equally beautiful left side, the sexy songstress eliciting the same response.

"Again!" Demi demanded once more, as it became increasingly obvious what was really going on. I spanked her again, but this time, I worked up the courage to send several vicious strikes to her bewitching bum, each one more powerful than the last.

"More, more, more!" She openly declared and I followed suit. Sure, her original intentions for getting me more involved may have been centered around making me cum, but it was blatantly obvious. She was enjoying me, far more than I was enjoying her. I'd gotten over the initial shock of fucking my celebrity crush, and was now coasting to victory. All the while, she was slowly falling deeper and deeper into a cock-induced trance.

Before I knew it, Demi was riding me explosively again. But try as she may, nothing seemed to get me closer to busting. No amount of enthusiasm from her end, no amount of pleasure on mine. I was dead set on fucking her butt; she could either give it up or admit defeat and accept me as her sponsored athlete. Either way, I win.

Unfortunately, Demi Lovato wasn't quite ready to do either option yet. She was far too stubborn to profess her inferiority, nor was she desperate enough to give up her most sacred hole. Not when she still had a few more tricks left up her sleeve.

The "confident" superstar gradually slowed down her movements, eventually grinding to a halt altogether. She allowed herself a brief moment to catch her breath, before rising again, this time pulling herself up and off my cock. I watched on as my throbbing meat slowly slipped out, revealing itself to be drenched in her feminine juices. My heart was pounding, wondering where this competitive match would lead me next. Before long, Demi explained.

Her breathing shotty at best, Miss Lovato informed, "You-you're a quite stubborn challenger, rook. B-but...I can assure you...that you're no match for me and- and I'll prove it!" With that, she rose to her feet before heading towards the mesh and motioning for me to follow. I adhered to the simple instructions.

Demi quickly arrived at the cage, sticking her fat booty out immediately and turning to look back at it. "You're not gonna move a muscle, got it? What you WILL do, is stand still like a good boy and let Miss Lovato work every ounce of cum out of that big cock! Understood?" I shook my head in agreement, but she insisted I do it verbally.

"What's that? I wanna hear you say, 'Yes, Miss Lovato, I understand!' Say it!"

"Yes, Miss Lovato. I understand." I played along, not wanting our little contest to end on behalf of my potentially bad behavior. Of course, I didn't have it in me to stand up to her anyway, so letting it slide was the best option here.

Just as I hoped, Demi quickly attacked my cock, her wet hole swallowing up my shaft the moment I got behind her. As promised, I stood motionless, allowing the Latin star to work her magic. The soft moans she let out said very little but meant a lot more in actuality. It was faint, but accompanying her moans was a small, hardly noticeable sound of despair. That little sound got louder as time passed.

Back and forth, back and forth she rocked her thick and tan frame, with her hole never seeming to get its fill. She gripped the cage with every fiber of her being, trying her best to cope with her struggle. She was quickly beginning to realize that every one of her ideas seemed to fall flat. Nothing was working; despite her sultriness and her stature, I was holding my own. With every passing second, I was proving that I was only a rookie by namesake.

Maybe because of my record, I appeared to be inexperienced. Not only am I a rising star inside of the octagon, but I had all of the makings to be the next big pornstar as well! And Demi was beginning to realize it.

Her opening was incredibly loose by this point, which allowed every inch of me to glide smoothly throughout her sex. All the while, she wore a dejected face, reminiscent of the won she wore when I was on top of her after our sparring session. She looked defeated, but unlike earlier, this time she couldn't be happier with the result.

Demi's pretty brown eyes glazed over, and her knees began to wobble. Her jaw dropped down, uninterested in keeping her saliva inside of her mouth. With every passing second, every bucking of her wide hips, she grew closer and closer to orgasm. As she approached the brink, I saw Miss Lovato reach her hand back and, deliriously, tap me on the chest. The game was over. I had won.

"Rook, you win! Oh GOODDDDDD! You win, okay? Now please, fuck me! Slam that big, hard fucking rookie cock in me! C'mon, fuck me! Make Miss Lovato cum!" Demi pleaded, flashing her best puppy dog eyes as the need to cum caused her to crack. I was sure that she could last longer than this; I couldn't believe how desperately she wanted that sweet release. Yet, now that the reins were finally in my hands, I couldn't help but deny her for now. She'd get to cum, but not until I get what I truly desired the most: her precious little butthole. So, I had no other choice but to push my anxiety to the side. Otherwise, I'd never get what I wanted.

Taking a deep breath, I asked, "You wanna cum, Miss Lovato?" Demi shook her head in agreement, which helped calm my nerves a bit. Taking it a step further, I spread her ass cheeks apart. Then, I elaborated.

"If you wanna cum, then...it's gonna have to be from THIS hole." She looked back, evidently shocked. But, since it appeared as though Demi couldn't believe what she was hearing, I reclarified my stance.

"I'm gonna fuck your asshole, Miss Lovato."

"N-no!" Demi struggled to respond. As always, the superstar was bold, if nothing else. But, I was well aware that, no matter how adamant she was, the need to cum would always be much stronger.

Continuing my surprising run of confidence, I explained, "Well...I guess you're not going to cum then." Again, she looked back at me with a stunned expression, then the same puppy dog eyes from when she begged me to let her cum. But this time, she was begging in the opposite direction. It was almost as if she was actively avoiding it; like she was saying, 'anything but my ass'. But unfortunately for her, that's all I wanted.

Demi continued to look back at me, hoping for any sign of mercy. None was found. In a final act of desperation, Demi at least found a way to keep herself alive in this intense battle of wits and stamina.

"Okay...you...can fuck my ass," she hesitantly agreed, spreading her ass by hand and giving me access to her most private domain. "But if you do, then our game is still on. One final round, whoever pops first is the loser, got it?" Something about her words came off incredibly disingenuous. For the first time all day, Demi didn't seem very sure of herself, which was surprising, considering the lower body she's working with.

"Yes ma'am," I assured, taking a head start by promptly removing inch after inch of my cock from her vagina, giving us each a second to breathe. Well, more so giving her some breathing time, I pretty much used my time to prep her likely virgin asshole for the strenuous task ahead. Based on her reluctance, I could only assume that Demi was a naive maiden, whose own natural unabashed confidence would prove to be her downfall in the end. Even if she wasn't an anal virgin, it was highly unlikely she'd ever taken anyone my size, so even thinking she could handle me was almost offensive.