Bet Gone Bad

This is my first story so I'm looking for lots of feedback but please be nice because I'm a big baby. Be advised that the story contains misogynistic language and of course non-consent/reluctance. Hope you enjoy!

Nate entered the room looking as smug as I'd anticipated. He wore dark jeans and a white, "wife beater" style tank-top over a gold chain. He'd taken out his earrings, too - it almost seemed like he wanted to look "tougher" than usual, which worried me a little. He'd probably been watching more of those "alpha-male" self-help videos again.

I was wearing a hoodie and sweatpants, and a rather unflattering pair at that. I think there might have even been a coffee stain or two. I remember wanting to make it as clear as possible that I do not give a fuck if he finds me attractive or not. That said... Nate was looking really good these days. His shoulders had filled out considerably, and it was hard not to thirst over how hot that was gonna be if he ended up on top. I held his gaze for a moment at the door until he crossed the room and sat beside me on the bed.

"Sorry to keep you waiting," his tone was sickly-sweet. "So... how does this work exactly?"

"I dunno." I shrugged, "I guess just tell me what to do." I did my best to sound unimpressed but diplomatic, "60 minutes starts now."

His smirk stretched into a nearly ear-to-ear grin, "Alright... on your knees then." He gestured in front of him.

We briefly locked eyes again before I quickly looked away, suddenly feeling rather self-conscious. I was determined, however, not to let him get in my head. The more insecure and uncomfortable I appear, the more he's gonna feel superior to me and I am far too proud to let that happen. I took a deep breath and got up to kneel in front of him, resting lightly on my heels with my hands clasped in my lap. He looked down at me like a kid in a candy shop: "So I can do whatever I want?"

"Within reason," was my response.

He didn't hesitate to stand and unfasten his belt. He struggled with the zipper for a moment but it wasn't long before he managed to bare himself in front of me. He was already decently hard and I was starting to get wet too, so I didn't resist as he parted my lips with the tip of his cock.

"Hands behind your back" he instructed me as he began to rock back and forth in my direction.

I followed instructions, and decided to close my eyes while I was at it. Somehow the embarrassment of sucking dick is a lot more tolerable when you can't see anything. Thankfully, he started off pretty tame: guiding his semi into my mouth with one hand while resting the other on the back of my head. He wasn't pulling on me though, instead thrusting forward and using his hand to ensure I couldn't recoil. I could feel him growing in my mouth as he steadily picked up the pace and it wasn't long before he had become quite the mouthful. No longer needing the extra support, his right hand joined the other at the back of my head - I was really starting to feel the bulk of him in the back of my throat now. He was getting dangerously close to gagging me...but maybe that was the goal. With his fingers laced around the back of my skull he continued to pull me closer with every thrust. Pushing himself farther and farther down my throat with each motion, I noticed the tingling of my own arousal.

In an attempt to slow things down again I resisted his movement so that I could pull my head back and slowly, very deliberately roll my tongue around the tip. That seemed to get his attention. I continued licking the head of his cock and then gradually moved farther up the shaft, secretly savouring the taste of his sweat as I did so. His hands fell down to my shoulders as I approached his balls and he lifted his pelvis slightly to give me a better angle. I licked and then sucked on the loose skin while ensuring my hands still remained obediently behind my back. I was starting to wish he had rope or handcuffs or something. I really, really wanted to touch myself but knew that would be game-over for my dignity.

This was a conflicting moment for me. I vehemently refused to give Nate the satisfaction of knowing he can get me off but... at the same time... oh my god I was just so fucking horny. He had started to buck his hips at me and I worried he was trying to speed up again so I refocused on the task at hand. (or at mouth, I suppose) I ran my lips up and down the length of him before taking it back into my mouth again, now thick enough that it's difficult to manoeuvre my tongue. Bobbing my head rhythmically, I could taste the faint hint of precum and this urged me to continue enthusiastically - hopefully he's the type who needs to rest a while after finishing. I'm sure I've visited every inch of his delicious cock by the time I reach up to cradle his balls and -

"I said hands behind your back." He growled, taking my head back between his palms. It was immediately clear I wouldn't be the one setting the pace anymore.

With his hands returned to their previous positions he was now grabbing handfuls of my hair while he's at it. Ramming his cock, his nice... warm... fat cock into the back of my throat over and over until I could feel myself starting to tear up. By this point my cheeks were on fire and I'm sure he could see that - which of course only encouraged him more. In and out, again and again, I'm sure my mascara had run all over my rosy cheeks.

Eventually he slowed for a bit, allowing me to regain some composure. Although I didn't know it at the time, the lull wasn't an act of charity but instead an opportunity for him to record me while I continued to suck diligently away. Now that we'd slowed I could feel the saliva dribbling down my chin - I must have looked like a hot, slobbery mess. Apparently satisfied with the footage, he resumed his near frenzied pace almost immediately after tossing the phone to the floor. It had become difficult to think clearly by this point, so I was caught off guard when he pulled my face down with him and sat back down on his bed. Happy to be in control again, Nate pressed my face into his lap until I could do nothing but sputter and gag. Barely allowing me to catch my breath, Nate alternated between vigorous throat-fucking and holding me down forcefully enough that my vision blurred. I could hear his breathing accelerate, and with each exhale he seemed to care even less about my comfort. Just as I was debating asking him to stop he finally broke past the gagging point and we were officially deep-throating. I was only able to hold the position for a few seconds before ripping my face away from him and choking violently.

"A bit too much for you to handle, huh?" I was still panting when he tilted my chin upward toward him, "Open your eyes." His voice was impressively commanding and my eyelids shot open. He looked down at me with a devilish expression on his face, "Let's try something else, shall we?"

He gestured to the bed. It was clear he wanted me to lay down but when I began to pull at the covers he grabbed my wrist. "Nuh-uh," he released my arm, "I want you on all fours... bitch." The expletive seemed added as an afterthought.

I crawled onto the bed as un-sexily as I could and he followed behind me. On his knees as well, he rested his hands on my hips for a moment before starting to tug at my waistband. I'll admit that he took off my sweatpants tantalisingly slowly; I desperately wanted him to hurry up because I was only getting wetter by the minute. Instead, he teased me. After pulling my underwear down to my knees, he shifted himself into a doggy-style position so that I could feel his dick pressed up against me from behind. What I couldn't figure out, however, was what on earth he was waiting for. He kept running his hands up and down my sides and then slowing at the hips to pull me in even closer. The bulk of my sweatshirt seemed to be getting in his way.

"Take this off," he ordered me dismissively, almost as if distracted by something else. I removed my hoodie unceremoniously and glanced at the clock only to find there were still 49 minutes to go. He gave me a look that told me to take the rest of it off too, and so I did. It was chilly enough that my nipples were especially sensitive, so I gave 'em a quick lil' massage before returning to position.

"You're very obedient." He cooed in my ear.

"Don't mistake my compliance for enjoyment." I responded as firmly as I could, but my voice wavered and I'm certain he noticed.

Nate laughed, "You sure about that..?" He started to play with my nipples, circling them with his fingers and twisting occasionally, one at a time. As expected, it felt amazing to have his body hulking over mine, completely naked, mere inches away from fucking me. I could feel the sticky warmth of his skin against mine, and he had started to rock me back and forth again.

"Because if I didn't know any better I'd think you were having a pretty good time for a bit there...." Using one hand for support, Nate continued upward with the other until he reached my neck - but he didn't squeeze. I decided not to respond, but that only seemed to rile him up more. I could feel the heat of his breath on my neck, and he tightened his grip on me a little before leaning back and instead prodding at my pussy an inch or so deep. "Ah, I was right..." he tsked at me, "you've given yourself away I'm afraid."

And he was right, I was soaked. "Just fuck me, will you?"

I didn't have to ask twice.

He sunk his hands into me just above the hips, pushing himself the rest of the way inside with ease. The initial poke had been slow, almost tentative, but he slammed every following thrust into me so hard it hurt. I whimpered occasionally from the pain, but he didn't seem to notice. Or maybe he just didn't care. Either way he wasn't letting up, but I was starting to think maybe I was ok with that. I could smell the sweat in the air and it was starting to make me feel lightheaded again. Smashing into me over, and over and over again, a moan or two escape my lips.

"Yeah, you like that..?" He pushed down on me so that my arms folded and my face was pressed sideways against a pillow. "..fuckin' slut."

It had become increasingly difficult not to show how turned on I was. He had me completely bent over with my ass straight up in the air, just pounding my pussy again and again, occasionally shoving my face even farther into the pillow at the same time. He gradually moved so that he was resting on his forearms and stretched to lightly grab hold of my neck while he did so. I couldn't get over how deep he could get. It hurt at first, but I couldn't get enough of him now. One of his hands drifted toward my face and I instinctively started to suck on his fingers.

He immediately recoiled, "What the fuck!?"

"Sorry," I couldn't bring myself to look at him.

"Fuckin' weirdo," he laughed and wiped his hand on the bedcover. I was still avoiding eye-contact but I could still see that he was dramatically examining his fingers. "You know, I've got a better idea - turn back around."

Nate sure was comfortable giving orders.

I positioned myself so that my legs were spread reasonably far apart this time, hoping that might make him a more comfortable fit. He started to tease me with his cock again, sliding it up and down my ass with ease. Occasionally he would pause, as if waiting for something, but it felt like several minutes had passed before he finally broke the silence: "I want you to beg for it."

"Please fuck me." The words spilled out of my mouth without warning.

"What was that?" He sounded equally surprised by my enthusiasm.

I started to squirm. "I want you to fuck me, please, Nate, please fuck me."

"Yeah?" He was inside of me now. Barely, but enough that my motivation to beg him for more had certainly intensified.

"I love your cock," I wasn't sure what particular embarrassing sentiment he was looking for, "Please Nate I want you inside me."

He rewarded me by sliding himself all the way in, groaning softly as he did so, but remaining still afterwards. I was itching for it by this point, so I impatiently began to rock myself back and forth on him. I knew he'd see that as proof I actually want him to fuck me, because it is, but I guess after sucking on his fingers that ship had probably already sailed anyway.

"Mmm.. good girl." he breathed into my ear, now joining in the motion. That got me thoroughly riled up, encouraging me to gradually increase the tempo. I knew he would never let me live this down but I didn't care anymore because oh my god it felt good to have him fill me up like this. He moved his hands from my waist and slowed a little, but I was more focused on the feeling of his balls slamming into me from behind.

I'm stirred from my stupor when I feel the sharp surprise of something entering my asshole. I guess this was the "better idea" for his fingers.

'Keep going, whore." I hadn't realised I'd stopped.

I attempted to pick up from where I left off but this time with a finger creeping its way up my asshole. Slowly but surely, oop that's a knuckle, until he'd fit his entire finger in there. He started to work a second finger into the picture and I let out a groan of approval. It hurt a little, but I still wanted so much more. "I wanna show you something, can I turn around?"

He didn't take long to consider the question, "Ok."

Removing his fingers from my ass, (as well as his dick from my pussy) I turned around and crawled over so that I was straddled atop him with my knees still on the bed and only his feet reaching the floor. Leaning my head over his shoulder, I reached around to find his dick and lined it up underneath me with little difficulty. After some manoeuvring I was able to sit myself directly on his cock, now fully erect, and gently ride the rest of the way down. The first time all the way in always sends a shiver down my spine, so I rested for a moment to savour the feeling.

It's not long before I'm back at it, but I can't get him very deep yet. He's a decently big boy down there and it still hurts too much. I can, however, cling to his body in a way that makes it significantly easier to maintain the speed we had worked ourselves up to - I could've gone like that for a while I bet. That didn't seem to be what Nate had in mind, however, because he suddenly put his arms on my shoulders and pushed me all the way down again. I cried out in surprise, somewhere between a yelp and a moan... god it felt good though. When I started to ride him again, much deeper this time, I winced not from the pain but instead from the thought of how obnoxiously cocky Nate was sure to be after this. I knew I probably should have at least tried to hide my pleasure but clearly that had become no easy task.

He began to move his hips with mine, and managed to put himself back in control of pace again in doing so. It would seem this boy can never go fast enough. I had my arms wrapped around him for balance but it was no use, I was bouncing around all over the place. I wished to myself that he would tire soon, but he instead lifted me at the knees, ass still stuffed with cock, and placed me on a lounge chair across the room.

"I'll admit that was impressive," I whispered to him - I'm still not sure what possessed me to stroke his ego even further. I briefly opened my eyes to see him smirk before he lifted my legs above my head and began to fuck me in the ass again. My eyes watered, and I questioned how much of this I could take. He seemed insatiable, just pounding me over and over. His breathing had become steadily more laboured and it sounded like he might be close. My asshole was loose and relaxed and I was eager to fill it with as much of his cock as I could. I wanted to feel the warmth of his cum in my ass, so I allowed myself to audibly moan. He leaned over me after that, reaching his hands out to pinch my nipples again. I tried to return the favour by kissing his neck but he immediately responded by leaning back and grabbing my neck with both hands. He hadn't really started squeezing yet but he was still fucking me unrelentingly.

"Open your eyes," he commanded.

I did as instructed and found myself reminded what a beautiful body this boy has. His tanned skin was mostly hairless, and I don't even want to think about how much time he must spend at the gym.

"Tell me you love my cock," Nate slowed a little as he spoke.

I can't help but look away, it's so much harder not to be embarrassed with my eyes open, but I force myself to say it anyway. "I love your cock."

The grip on my neck tightened, "C'mon... you can do better than that."

I forced myself to look into his eyes and praise his cock, but my voice had become raspy from the pressure on my windpipe. That wasn't good enough, apparently, and he continued to fuck me relentlessly. I was starting to see stars and desperately needed a reprieve, so I forced myself to sputter another, "Please, I love your cock so much."

This seemed to please him at least slightly, because he relaxed his grasp. Set on furthering this behaviour, I rambled almost incoherently: "You're so big oh my god, please, I want more. I love it oh my god, thank you, thank you I love it..."

"More." Was his only response.

"Nate you make me so wet..." I moaned intermittently, "...I need it... I'll do whatever you want... and I'll love it... thank you... for fucking me... oh god thank you..."

He released my neck and moved his hands above my shoulders so that he could just absolutely rail me. I tried to move my hand toward my pussy but it was no use - he was fucking me far too violently to do anything useful down there. Instead I focused on the feeling of him inside of me, pushing right to the end, over and over and over but I always wanted more. The room smelled like sweat and I could feel the moisture pooling underneath me.

"I wanna taste your cum." I blurted out, surprising myself again. His breathing had become highly erratic, he must have been close. "Please, I want to taste you. Will you please cum in my mouth?"

In one motion he pulled himself out of me and roughly shoved my face down toward his cock. He gave himself a few last tugs before grunting in ecstasy. I opened my mouth as wide as I could to try and catch as much of his delicious cum as possible but a lot still ended up on my face and some even in my hair. I wiped the excess from my eyes and leaned over to lightly suck the last dribbles off of him.

He scoffed at me. "Hey... you're on birth control, right?"

I stared in disbelief before rolling my eyes. "....because now is a good time to be asking that."