Sponsored - Featuring: Demi Lovato

Although, if there was one thing I learned about the sultry and sexy Latina, it's that a big ego can go a long way. With the rest period and lack of real anal training, she might actually be able to outlast me. Nevertheless, I wasn't here for anything less than her best. Ready or not, I was going to destroy her little bumhole nice and good.

Never in my life did I feel more confident than now, with my tongue shamelessly worshipping Demi's asshole. She couldn't help but tremble from my touch, as what seemed to be a brand new stimulation overrode her senses. There wasn't an ounce of pain to be found, not from my slippery little appendage. Only pleasure, as Demi was seemingly forced to fight off the urge to cum from what had to be her first rimjob.

The more I licked and tongued that butthole, the more it seemed to spring to action. What was once a dry, lifeless orifice had become a sticky, irriguous fuckhole, just waiting for something bigger. Throughout, never once could I feel my shaft soften; knowing that I'd be giving the butt of my dreams everything I've got put a smile on my face. That smile turned into a wicked grin as I lined my cock up with said butt and pushed forward.

Much to my surprise, Demi was able to easily swallow up my head, as well as the following few inches. My expression transformed again, and now I was the one wearing their shock on their sleeve. Demi's face, however, once again returned to that droopy, emotionless state. She was back under that powerful, cock-induced trance. But this time, it was her supposedly forbidden hole that was the culprit.

Her stretchy bumhole easily expanded and adapted to my size and shape, without an ounce of legitimate lube to loosen it up. I was impressed, especially since I'd taken Demi for an anal virgin due to her hesitancy. But, as I'd learned throughout the night, she was just as wild a gal as the press had made her out to be. A party girl with a penchant for breaking the rules and, apparently, taking it up the ass, based on the speed at which I managed to stuff her full.

Hardly a minute had passed before Demi had taken every inch of my massive rod up her slutty butt, the pretty pop princess moaning like a shameless buttwhore all the while. I couldn't believe what I was seeing; Miss Lovato could barely hold herself up. The pressure in her ass had to be intense, as I highly doubt she'd ever taken anybody half my size up her butt, regardless of experience. Nevertheless, through heavy breathing and shaky legs, Demi managed to do it with a smile on her face. For the first time since we'd begun, she didn't look determined to beat me.

Instead, Demi's visage appeared to be begging me to move, pleading with maximum effort to begin the sodomization. I took her expression as such, using it as a lure to motivate myself to begin butt-fucking, of all people, my teen dream, Demi Lovato. Just the thought alone brought me close to cumming, myself. Never, not even in my wildest fantasy, would I have deemed this possible. Here I was, less than 24 hours removed from winning my fourth pro fight, fucking a world-renowned popstar's juicy ass. Best of all, Demi was loving it!

Beginning to move my hips a bit faster, I took hers into my grasp, giving myself improved leverage as I planned to kick things up a notch. For the first time tonight, I was in control, and all I needed to do to win our game once and for all was make Demi cum before I did. A tall task, both on paper and in practice, especially with her snug, toasty hole gripping my rod like a vice. The Latin looker was getting me close without even trying. But lucky for me, Miss Lovato seemed to be losing the battle.

My suspicions about Demi being inexperienced with her butt, let alone being an anal virgin, were far and away incorrect. As she unabashedly moaned out from having her asshole ravaged, it became abundantly clear that Demi Lovato was an anal whore. A pathetic buttslut who loves taking it in the ass, far more pitiful than I ever could've imagined.

It occurred to me that the reason she was so hesitant to give her fat butt up was not that she wanted to remain abstinent, but instead because she knew that if it came to having anal sex, she'd lose for sure. That's why she prolonged it for so long, taking me in different positions and using every other tool in her arsenal when this magnificent little fuckhole could've done the trick much earlier. Taking my cock in this fashion was a guaranteed loss for her, and Demi only agreed to give it up when it meant keeping the game alive. When she'd exhausted all of her options and even after she'd already admitted defeat. When she had nothing left to lose.

Even in her foulest, most depraved hour, Demi brought about a certain swagger. She was well-aware of what would happen and she was smart to do so. Demi wanted so badly to avoid her current reality, to avoid a life-changing anal experience that would spell the end of her chances in our wager. But, even still, her desire to win prevailed over everything. Despite the reality of the situation, despite her obvious anal fixation, Demi Lovato had been "confident" enough to make one last challenge. To go all-in, per se, something I couldn't help but admire as I continued to brutally pummel her hole, my cock gliding throughout at will as I fucked her closer and closer towards a blissful buttsex orgasm.

Every inch of my dick barreled in and out of her hole, yet no matter how strong or how fast my thrusts got, she stayed relatively tight. Not too much or too little, but just enough to grip my cock whilst also giving me free rein over her backdoor. By now, there wasn't an inch of that chute that was yet to be pleasured. I'd tantalized every spot, from Demi's shallow entrance down into her deepest, darkest depths, slamming into her with so much force that her ass cheeks quaked with each thrust.

Each moment seemed to linger for hours, and I could feel my cock beginning to pulsate. For as cool as I'd managed to play, I was just as close to cumming as she was. Well, maybe not quite as close as by now, Miss Lovato, through all of her brashness, was no longer even capable of standing. The dangerously curvy and delectably delightful diva was reduced to nothing more than a pile of mush, sprawled along the bottom of the mat, her pretty, sweat-stained face matted against the mesh just above it. Demi's voluptuous body wore the same glisten that her mug did. But, just when it seemed like she was spent, the successful songstress, yet again, managed to surprise me.

After upwards of twenty euphoric minutes of getting fucked lifeless, Demi finally began to throw that fat booty back against my thrusts. And yet another surprise came when she looked back and delivered a hazy, cock-drunken message alongside it. "Ohmigod! OH! My! Fucking GOD! I'm gonna- holy fuck!" I knew exactly where she was going since I'd heard it once before. Naturally, my nerves, something that'd plagued me my entire life, were non-existent. Fucking Demi Lovato was an emotional roller-coaster, and if so, then sending her hurtling towards an orgasm was the loop-de-loop. She was moments away, and without anything to stop me, I mustered my courage back up.

"You're what, Miss Lovato?" I barked, slapping her jiggly ass hard. "You're gonna cum?! Fucking do it then! Cum! Show the 'rook' how you cum like a good girl! Do it, bitch! Cum!"

With my victory all but secured, I took my conviction a step further, grabbing the world-renowned woke warrior by her raven-colored tresses and pressing her face against the canvas. Instinctively, Demi raised her big butt as much as possible. Face down, ass up; there was nothing in my way now. I gave that used-up rectum every ounce of strength and energy I had left, hitting every spot available throughout my conquest of her ass. All the while, Demi proceeded to emit a guttural screech as an even stronger pleasure began to wash over her.

First, her hips went numb, with her legs following closely behind. Then, that numbness spread to the rest of her body, making it nearly impossible for Demi to hold herself up. She did though because a world where she didn't continue to impale herself was far more terrifying. So, as she approached the edge, Miss Lovato bellowed out, hammering her ass back at full force. Our connections echoed throughout the room, but even still were nearly drowned out by her screams. Then suddenly, she stopped.

Demi pulled herself up and gripped the mesh before releasing one last ear-splitting roar. Upon hearing her, I knew it was time. Just as I'd suspected, I felt her asshole tighten around me hard. Then harder, and then a bit harder than that, until it felt as though her ass was literally about to break my cock in half. Demi shook violently, and that was all she wrote.

Demi crumpled onto the floor, seizing up as she was finally able to cum. The relief was evident in her face as the immense pleasure rushed through her. She didn't look upset about her loss in the slightest, only happy to have experienced such a joyous moment, that being an anal orgasm brought upon by the biggest cock she'd ever taken before. But, while she lay there, still overwhelmed with bliss, there was one thing still left to do.

Now that I had won, it was high time that I, myself, get to cum. After everything the sultry songstress had put me through, the demeaning, using every part of her body to work my load up and the like. I'd put it off to win our little game, but with that all said and done, and my confidence higher than it's ever been, now was the time to act.

"Get up and get in the middle!" I demanded, with my new celebrity sponsor sluggishly adhering to my demand. She had gotten what she wanted; I allowed her to cum already, so Demi could've easily decided not to listen to me. But apparently, she was a woman of her word. She'd lost and was more than willing to allow me to reap my rewards.

With a smile on her pretty face, Demi crawled over to the center of the mat, kneeling right below my cock. Using my right hand, I slowly dropped her jaw, before stuffing her mouth full with my cock. Much to her surprise, I immediately tried to stuff her throat with the entirety of my dick. As she gargled and choked on inch after inch, I found myself with the same problem that Demi had earlier.

Her windpipe was far too narrow to accommodate my epic length and girth. Demi was nothing if not a trooper and was more than willing to try, but as much as I did, I didn't do much better than she had. That was, until I took her shoulder-length, dark brown hair into my grasp, using it to pull her head in closer. Naturally, my cock was still lodged halfway down her throat.

Gripping her skull, I proceeded to ravage the inside of her mouth with reckless abandon. Much like she had, I'd grown frustrated with my failed attempts at a proper deepthroat. Now, not only did I want to cum, but I also wasn't willing to until I managed to stuff her full. Every. Last. Hole. Her pussy had taken it, as did her ass. So, I was certain that by hook or by crook, Demi's mouth and subsequently, her gullet, could do the same.

I pushed in harder and harder, only showing my teen crush the tiniest slivers of mercy in the form of a few breaths here and there. Demi even slapped my thighs in a desperate attempt to get me to stop. But I couldn't; slowly but surely, as tears began to fall down her face and spit coated the rim of her mouth, Demi began to take more and more. 9 inches, then 10 inches. I allowed a quick breath, before going back in. 11 inches. Then finally, at long last!

All 12 inches of me, stuffing Demi's throat to the brim. But, I was riding an emotional high, so I didn't plan on stopping there. Never really wanting this bliss to end, I began to skull fuck her, which was a rather brutal decision on my part. Honestly, I just couldn't help myself! I'd deviated too far from my usual persona to care. And it wasn't like Miss Lovato wasn't enjoying herself.

After many prior attempts, Demi couldn't have been happier to manage every inch of me. The schoolgirlish giggling that she barely squeaked out was evidence of that. I was fulfilled and now, so was she. All boxes were checked. Every I was dotted, every T crossed. I'd successfully cashed in on my "signing bonus". Now all that remained was the grand finale.

Her head still locked in my grasp, I slowly dislodged my cock from her cramped passage. Inch after inch exited, leaving Demi in both a state of relief and yearning. She was glad to regain the ability to breathe but was happy that she had been pushed to these new heights, even though all of her hard work hadn't paid off in the end.

Despite her best efforts, I'd passed every test Demi threw in front of me. Surviving her in the octagon would have always been a cinch, but maintaining my composure while fucking one of the hottest women in the world was always going to be a far greater challenge than any fight could.

Demi knew she'd been bested; I earned my right for her sponsorship, fair and square. As my cock finally slipped out of her mouth, leaving a long strand of spit attached, Demi Lovato finally realized that her agent had been right all along. I was the right guy for her to sponsor. Sure, I may have been a rookie in practice, but I was nothing if not a rising star. 4-0, and things were only going to get better from here.

My new celebrity sponsor looked up at me, patiently awaiting my sticky white load, the load she'd tried and failed to bring out of hiding, to rain down on her. After a few intense seconds and relaxing breaths, out came ropes, showering her pretty face and glazing her up real nice. It was a huge load, probably the most I'd ever cum before, which was no doubt brought upon by the goddess who'd put in the effort to work it up.

Demi smiled gleefully, licking whatever her tongue could reach, before snatching a big glob of the white stuff from her eyelid and quickly tossing it in her mouth, letting out a soft moan as she did so. "Congrats, rook. I think you've more than proved me wrong," Demi suggested. "We'll have to 'spar' again sometime!" I smiled back at her, knowing that I'd truly impressed the pop sensation, but unable to find a witty response. Instead, I tried my best to casually laugh with her.

My newfound confidence was gone; sadly, I was back to normal. Never in my life have I been a charismatic guy. Struggling to find the right words has always been my biggest flaw, outside of battling my anxiety most of the time. But, for once in my reasonably poor existence, the tiniest sliver of my time on Earth, I had the upper hand against my insecurities. And doing so brought upon the greatest opportunity and experience of my life!