Bossman's List

by Ashlee Price

  "Look at me, Hailey."

  I looked up at Josh with my mouth still open.

  "Swallow."

  I did and after wards I opened my mouth wide so he could see I really did leave nothing to waste. The rest, however, was still all over my tits and face.

  "Good job," he told me. For an odd reason, it made me feel so proud.

  "Please, Josh," I softly, weakly said. "Please let me cum."

  Josh smiled and he cupped my cum-splattered face, "You will, honey, but now from my hands."

  Huh? I felt a sudden whirl of confusion.

  Josh saw the puzzlement shot across my face and said, "Someone else is going to make you cum today." With that said he looked over towards my bedroom door and so did I.There was Brad, standing completely naked with his cock in his hand.

  "Oh fuck," was all I could say.

  Chapter Three

  How long had he been standing there? Was he there the whole time me and Josh were on the bed or was he there since the very beginning? Something from the back of my head told me that they probably planned this. Heck, they probably agreed to “baby-sit” me for my father because they knew that an opportunity like this might come.

  Dirty pervs... but somehow I liked it. No - I loved it!

  “Come here, man, I got her all set and ready,” Josh told Brad.

  I knew it; they had this all set up!

  Brad walked over as Josh got out of the way. Josh continued to gently stroke his cock and I watched as he kept his gaze on my naked body. I loved the way he raped me with his stare - it made me want to pleasure him one more time.

  But there was Brad and I knew I had to give him a chance too. After all, this was going to be a long weekend with my Daddy’s best friends so I had to make them both happy if I wanted them to make me happy too.

  Yet there was something even more enticing about Brad. He was built like a football jock, huge and muscular, in a way that made even my slightly heavy build look like a petite little frame against his. The muscles on his arms looked as thick as my neck and when I stared at his cock it throbbed in his hands like a raging beast just waiting to unleash itself onto me.

  “Oh my...” was all I could whisper when he brought that monstrous cock up to my face.

  “You like cum, don’t you Hailey?”

  “And you want to cum?”

  “Please, I really do!” I answered as I squirmed on the bed, trying to rub my pussy’s lips against each other. It was getting hard to control myself. If only I would be allowed to play with myself I could find relief and let myself just cum as I desired.

  Brad’s face broke with a wide smile, “I’ll let you cum, but first you got to know what it’s like to be sandwiched.”

  “Huh?” the blank expression on my face said it all.

  “Turn over, honey,” Brad told me and I did without question. I wondered if he was just going to pound me doggy style. After all, most men found that pleasurable. But then he finally told me what he wanted and the “sandwich” part sank into my head.

  As I got on all fours Brad gave my ass a good slap as he told me, “Open your mouth, you’re not done with Josh just yet.”

  I did and I looked at Josh with a curious face. He walked up to me, got to the bed, and knelt in front of me as he positioned himself to insert his cock back into my mouth. I didn’t try to stop him. I just opened wide and reveled in the joy of letting his meat fill me up one more time.

  This time however, Josh grabbed my head with both hands, indicating that he wasn’t going to let me stop sucking his cock until he was done. I pondered what I had gotten myself into this time.

  “F-fuck,” I tried to yell out as Brad pounded his cock straight into my pussy with no warning but Josh’s cock had muffled my cries as he began to thrust it in deeper into my mouth. He rammed it deep enough to hit the back of my throat, almost gagging me in the process.

  In an instant I felt all control just slip through my fingers. Brad’s large, heavy hands grabbed me by the waist and he continued to pump his cock in and out of me with a raging fury that made me feel like he was intentionally tearing my body apart while Josh was in front, slamming his own flesh into my mouth to silence any form of protest I could utter.

  In truth, however, I had nothing to complain. This was exactly how I imagined things would go when I was taking my shower just about thirty minutes or so ago. This was exactly the kind of kinky taboo fun I wanted the moment I walked down the stairs, my nipples showing against my clothes, when my dad first told me they were going to spend the whole weekend with me.

  Slam!

  I felt Brad’s whole body pound against my ass as he plowed his manhood into me deeper and deeper. My ass cheeks began to feel a little sore he kept on penetrating and pushing in as deep as he could. His cock was thick and with each thrust I could feel how it was ripping through my inner walls, widening my pussy with each passing second.

  Slam!

  My thoughts jumbled again when Josh rammed his cock deep into my mouth, slamming his balls right up to my face. I wrapped my arms around his waist and both men began a back and forth volley as they fucked both ends of my body. It was nirvana in a weird, sex-filled way and I wanted to drown in every second of it.

  Pop!

  Josh and Brad pulled out simultaneously, as if they could communicate without saying a word to each other. Brad gave my ass one more hard slap, forcing my mouth to gape open wide as I moaned, “Aah!”

  “Look at that pussy,” Brad told Josh. “It’s so wide open you could fit anything in there now. You love cock, don’t you Hailey?”

  I turned around to lie on my back. As I did I answered, “I do, I really do. All day I dream of someone like you guys to just take me without asking and pound a cock into all my holes.”

  “Your daddy would be shocked to hear his little baby talk like that,” Brad told me as he stroked the length of his cock. “Your daddy would think he failed as a father because his daughter is becoming a cock-hungry slut.”

  “Daddy would be proud,” I replied. “He did tell me to be a good girl for you guys. He keeps saying you are his best friends and that I should do everything I can to make sure you guys feel at home here, remember?”

  Josh laughed and he walked over to me and spread my legs wide apart, “We’re going to be here for two whole days, honey. You think you can keep up with us?”

  “I don’t know, what if I can’t?”

  Brad stroked his cock even faster, as if my response ignited something in him, “Oh, if you fail Hailey, we are going to do everything possible to turn you back into a good, obedient Daddy’s girl.”

  That sounded more perverted than it should have been but it brought a wicked smile to my face.

  “Fuck me,” I said proudly. This time I meant it with a whole heart.

  Josh was quick to oblige. He wrapped my legs around his body and pushed his manhood through the moist and sore folds of my flesh. I was slippery wet this time so he had no problem penetrating into the deeper depths of my pussy. As soon as I felt his cock go in deep my whole body shivered as if I had just been activated by a bolt of lightning.

  He pulled out but only halfway and then once again he thrust his cock back into me, this time a little deeper. He pulled back again and then pushed in deep. He started to build a steady, slow rhythm that rocked my body with each inward and outward movement.

  I reached up with both hands and Josh took them both. It was a sweet gesture but when I saw Brad take position beside me I realized Josh was simply holding me to make sure I couldn’t protest.

  I turned to the side just in time to see Brad’s throbbing cock bob right in front of my face. I opened my mouth and licked its head, trying my best to put it into my mouth without using my hands. Brad just knelt there, dangling his cock in front of me as I tried my best but failing to suckle on it.

  Slap!

  Brad held his cock and slapped my cheek with his cock, “Suck on it, Hailey.”

  I tried. But each time Josh po
unded his cock into my pussy my whole body moved and I had to aim my mouth again. It didn’t help that Josh was beginning to penetrate in and out even faster now.

  Slap!

  Brad struck me on the other cheek with his cock.

  I lashed my tongue out and immediately it struck the tip of Brad’s cock.

  “Aah,” I moaned out with my mouth wide open. Finally I managed to push my head forward at the right time and Brad’s cock popped into my mouth. It was a bit jolting at first, because it was so thick I thought it would break my jaw. I worried that my teeth would touch his most sensitive areas but it didn’t seem like he cared. As soon as his cock was in he inched a bit closer and began thrusting in and out of my mouth with his hands on my head.

  The roles were reversed. Now it was Josh plowing into my pussy and Brad was the one making me drool all over my bed as he pounded into my mouth and throat.

  I slobbered all over Brad’s cock. I found it hard to breathe but I also wanted to keep his meat in my mouth for as long as I could. It just tasted so damn good! And when would be the next time two hunks would walk into my bedroom to take me without warning?

  I drooled all over my chin, his cock, down my neck and to my bed. Brad didn’t care. He only cared about fucking my throat like it was the cheapest sex doll he could buy. His grip on my hair tightened and I wanted to yell but the only sound I could muster was a weak muffle between thrusts of his cock.

  Splash!

  My eyes shot wide open the moment I felt Brad spill his cum deep inside my mouth. I tried to pull my head away but instead he pushed my head in deeper, shoving his cock deeper inside my mouth as he could. My mouth and throat filled with warm cum. It was starting to fill me up too quickly and I felt myself gagging. My chest heaved as I began to choke. I opened the very edge of my mouth and foamed cum frothed out and dripped down my cheeks and chin.

  Finally Brad let go and pulled his cock out at the very moment I thought I was going to pass out. He threw my body down on the bed. My eyes just stared blankly at nothing and I felt Brad’s semen just drip out of my mouth. I was full and I was broken.

  Josh pulled out of my pussy and as I lay there, seemingly lifeless save for the weak movement of my chest as I breathed ever so softly, he stroked his cock until he spilled his seed a second time today. He spilled his cum all over my pussy and tummy.

  “Look at her,” Brad said.

  “Now she looks like a work of art.”

  Josh gave my pussy a sudden but gentle slap. I would have yelped but I was too exhausted to care this time. I just remained in bed like a lifeless doll broken by two boys who played too roughly with me. It was only after a while did I realize I was squirting my juices between my legs.

  The warmth of my orgasm made my body shudder. My mouth gaped wide open as I felt a sudden rush of ecstasy rush through every inch of me and though I tried to scream the only sound I heard actually come out my mouth was a soft, low moan of pleasure.

  When I was done, soaking wet with cum and sweat, I slowly turned my head and stared at the two men who had ravaged me with no mercy.

  “I told you that you’d have to work for it,” Brad told me when he caught my gaze.

  “I fulfilled my promise and we let you cum but it was a fun job working for it too, wasn’t it?”

  I weakly smiled and gave a quick nod. Slow drips of my cum still flowed out of my pussy as I shut my eyes and drifted off to sleep.

  Chapter Four

  When I came to, I found myself in the living room sofa. I realized I had been bathed and was wrapped in one of my favorite blankets. Underneath, however, I was still naked.

  “Hey, someone’s awake!”

  I turned to the side and saw Brad sitting on the recliner, dressed in his pants and shirt and held a bottle of beer in his hand.

  “Hey,” I greeted with a smile. “How long was I out?”

  He shrugged back, “About six hours. You slept good. We had enough time to give you a warm bath in the tub.”

  My cheeks flushed and I meekly replied, “Thank you. That’s actually pretty sweet.”

  “It’s the best we could do after fucking our friend’s daughter like a whore.”

  There was that word. “I’m not a whore or a slut.”

  Brad chucked at my response, “I said like a whore but I didn’t necessarily call you one, honey. Guys just love it when their girls let them do anything they want. Most of the time the only girls that are that open are sluts.”

  “So if I let you do anything you want, no matter how rough or degrading or taboo, you still wouldn’t call me a slut?”

  “No, because you’re only doing it with me and Josh,” he explained.

  “You promised your daddy to be a good girl, to make us feel like this is our home too, and so far you’ve accomplished that right after your daddy left with Jessica.”

  That was when I realized Josh was nowhere to be seen, “Hey, where’s Josh?”

  “Oh, he had to go out to make a beer run,” Brad answered. “We’re planning on binge-watching ‘Falling Skies’ tonight so we’re going to need some drinks to get through a few seasons.”

  Hmm, that was a good show. At least Brad and Josh weren’t mindless jocks. They had brains and they made good use of their wits too.

  “I’ve already seen everything up to season 4,” I told him. “Doesn’t season 5 come out next month or something?”

  “Yeah, so we’re going to play catch-up and binge-watch the whole series.”

  I frowned, “That’s boring. What am I going to do? Finger myself until I fall asleep?”

  Brad laughed at the notion, “That would be something fun to see but I got a better idea. Josh and I will watch and you can sit on the floor and suck our cocks. Whoever cums first loses.”

  Okay, that was funny but it also turned me on, “That’s crazy!”

  “But you know you want to give it a try,” he said as he gave me a wicked look paired with an evil grin that just told me he knew I was up for the task.

  “Of course I do,” I admitted. “I want to feel your cocks in me all the time. To be honest, I thought no one would really want to have sex with me because most guys prefer skinny bitches. Back in high school, I never got to date the hottest guy on campus and the only reason I ever got laid was because they couldn’t stop looking at my rack.”

  Brad raised an eyebrow and answered, “Well, you do have humongous tits. I could fuck and suck those all day. But let me tell you a simple truth: those skinny bitches in high school? They won’t get any sex after college. Trust me. When guys get a bit older they realize that a girl needs to have some meat in her. Nothing feels better than being able to just grab onto a girl’s waist while fucking her from behind. When I slap a chick’s ass I better hit meat and not skinny bones. If I wanted to fuck a skeleton I’d go to a morgue, not to a bar.”

  “Or your best friend’s house to fuck his daughter,” I added and Brad chuckled in agreement.

  Slam!

  We both turned our heads towards the kitchen just as Josh walked in with two six-packs of beer. He set them down on the floor and took his boots off before stepping into the living room.

  “Hey, you’re up,” he told me when he saw I was awake.

  “Yeah, and she’s ready for our game,” Brad told Josh as the latter took a seat on the long couch.

  Josh looked back at me with a smile, “I’m not going to blow my load before this dude does.”

  “How are we going to do this though? I can’t suck you both off at the same time,” I said.

  Josh whipped out his smart phone and replied, “We’re going to time how long it will take for each of us to orgasm. If it took me five minutes and Brad three, he loses the bet. We’ll use my phone to make sure no one’s cheating in regards to the time.”

  “Is there another way to cheat?” I had to ask.

  Brad nodded and answered, “If you suck me good but do a lazy job on him, of course I’ll cum faster than he does. The whole thing depends on your consis
tency, Hailey.”

  Ah, fuck. The balance of the universe once again rested on my shoulders. But I was up to the challenge.

  About three hours later we began. They tossed a coin and Brad had to go first. He sat on the couch I was sleeping on and spread his legs just as “Falling Skies” was streaming on the TV. I didn’t pay much attention though and concentrated on doing a good job. I tossed my blanket to the floor and knelt down to slowly pop Brad’s cock in my mouth.

  I decided to go slow first and after a few moments I’d start going faster and focus solely on the head of his manhood. I wanted to make them cum as soon as possible but in order to do so I needed to spend a few moments getting myself ready so a few slow licks were in order.

  Brad actually did a pretty good job. I was bobbing my head up and down, sliding the length of his cock furiously as I began to drool and slobber over his meat. Within minutes I was already lusting for more and I tried to plunge in as deep as I could, allowing his cock to push through to the very depths of my throat. I gagged once but it turned me on even more and as I felt my pussy begin to moisten I sucked him even deeper and faster until finally Brad spilled his cum all over my face.

  Josh didn’t wait a single second. As soon as he had clocked in Brad’s time on the phone he restarted the timer and pulled me to his side of the sofa and thrust my head to his cock. I wasn’t even able to swallow all of Brad’s cum and already I was sucking on Josh’s.

  In the end, however, Brad prevailed. He lasted a good seven minutes and forty-two seconds while Josh exploded his orgasm in under five minutes. I guess I was getting better at this.

  When Josh pulled out of my mouth I had trouble speaking. There was still so much cum in my mouth and they had both spilled their seed over my face, covering my eyes in the process. I couldn’t open them well enough to see.