This story is purely fiction, although some elements are based on personal experience.
I really enjoy comments so please feel free to send feedback to Jim.boski@yahoo.com and remember to support this site to keep stories like these coming by donating to http://donate.nifty.org Chester's little BIG brother Terrance had just finished throat fucking me with his huge meatstick and I still had the taste of his cum in my mouth.
I sat up on the massage table and watched as Terrance and Leyna walked towards the door, his big hand grabbing her ass under her short skirt.She glanced over her shoulder to make sure I was watching and then turned back to look up at the big black cocky teen. She spoke in low, rapid Portuguese, darting her eyes back at me and then to Terrance. I could only make out a few of the words.... whore, slut and cunt... but it was obvious she was talking about me. " I know, I know baby.... but if you can't please your man the way surfer boy over there just did... I'm gonna have to let you go.... how about Senior Reggie? He got a dick just the right size for you baby.... in fact... I think your dick is just a little bit bigger haha." The petite Brazilian shemale punched and kicked and cursed at Terrance in English and Portuguese.... calling Reggie a fucking pig and me a fucking faggot cunt. She spun around glared at me with fire in her eyes and spit in my direction....." Fuck you, you stupid gringo whore! I cut you then fuck you in your sleep.... then nobody pay even one dollar to fuck you.... they all fuck you for free in the bushes like the other gringo bitch Erik!"
" Whoa whoa there.... Terrance you need to take her outside NOW! Maybe toss her in the pool till she cools off. In the meantime.... Chester tossed me a gym towel......YOU... wipe your face off and go stand in front of the House Rules sign. I'm going to decide the consequences of your failure to follow a few simple rules." I wiped the cum and spit off my face and tried to get as much out of my hair with the little white towel. I jumped off the table and stood obediently in front of the House Rules sign, naked and nervously awaiting my sentence. " Standel!! How in the fuck did you manage to break all the rules in your first night??" " Well, it was dark and I didn't have a watch and..." " Never mind....you're going to be able to tell time without a watch or clock or mother fucking sundial by the time I'm finished with you! Now lay back down on the table face down with your head in that little hole. Now spread your legs out on either side of the table while I make some adjustments." I stared at the floor through the head hole while Chester adjusted the legs until my feet reached the floor and I was now almost straight up and down. " Put your hands here Standel and grab hold." I gripped the legs of the table while Chester wrapped wide nylon straps around my wrists and secured them to the table. " Is that too tight?" " Yeah Coach, just a little." " Good! I don't want you wriggling free. Now, move your feet over here." He kicked my feet till they were adjacent to the bottom legs of the table and secured them with nylon straps. "There, now you're properly positioned to receive your punishment. I'm going to step out for about an hour for a telephone conference with Mr Stihl from Budapest.... we're hoping he has good news about the bidding war for your virgin pussy. While I'm gone, I want you to think long and hard about what you've done wrong and what you expect in the way of discipline to correct it. Am I understood Standel?" " Yes Coach, I deserve everything that's coming my way and I won't do it again." Chester moved in close to whisper in my ear.... so close I could feel the bulge in his shorts pressing against my bare ass. " Good pussyboy" he whispered, his lips and tongue brushing my ear as he ground his hot package between my butt cheeks. " Here's a little something to make sure you don't forget while I'm gone." He reached around and firmly grabbed both my nipples, twisting hard as he dry humped my exposed buttocks. "Owwww fuck that hurts!!!" He laughed, slapped my ass hard with his open palm. " Be good little surfer boy... I'll be back before you know it." I heard Chester walk away and then slam the door shut. What the fuck am I gonna do for the next hour or so? I stared ahead through the head hole of the table at a blank wall. I tried to move my head to either side but I was strapped too tight to do it. Great, I have an hour to stew over how Chester is going to punish me.... but more pressing... who is going to pay for the rights to be the first penis to penetrate my virgin pussy? I can't imagine what kind of man would have the kind of resources to just blow millions of dollars just to say he was the first to fuck a little teenage surfer boy. Then I flashed back to Achara and the rich Tokyo businessman and the horrific Samurai mural in Rick's elevator.... and what about Reggie and the Russian tycoon? What did he do to Reggie to scar him for life? Suddenly the lights went out and I was in pitch darkness again. Just wonderful! I was so exhausted, that even though I had all these fears in my head and I was standing up, the darkness enveloped me and I fell fast asleep. The lights came back on and I was jolted awake. I heard the door open and slam shut and the sound of heavy footsteps heading towards me. " Are you ready to receive your punishment??" " Uhhh yes Sir.... how did the meeting with Mr Stihl go?" " Never mind about the meeting... that's none of your business." What the fuck I thought to myself... none of my business???? We're talking about MY virginity afterall!! Oh my gawd... the bidders probably all pulled out of the deal and now I'm worthless and Chester's going to take it out on my ASS!! And what about his little brother Terrance? He's gonna want to slit my throat once he finds out he's not going to get a new house!
"Now let's get rid of this.." He roughly yanked the butt plug out of my ass " it's just gonna get in the way of your punishment." So this is it then.... I'm going to lose my cherry to a black man while strapped to a massage table and I can't even look him in the eye as he takes it from me. " Open up bitch!" He shoved something hard and rough into my mouth. " Bite down! It's rawhide... it'll help with the pain and keep you from screaming." I bit down and braced for the worst. So losing my virginity is obviously not going to be some warm glowing experience... it's literally going to be hell on earth! " Get ready boy... here it comes!" Oh my gawd... no lube or prep! I bit down harder on the rawhide and braced for pain. Whaaack!! Whaaack!! The impact of hard leather on my bare buttocks shocked me to my core. The sting was excruciating and I could feel tears start to well up in my eyes. Chester came around to the underside of the massage table, took the rawhide out of my mouth and looked me in the eye... " You ready for more boy??" I sobbed heavily " Yyyyess Sir" " Good boy! Open!" I dutifully accepted the rawhide between my teeth and waited for what seemed like a minute for Chester to administer more blows with the leather crop. Whaaack! Whaaack! Whaaack! Whaaack! Chester made sure both my ass cheeks tasted the crop equally. Whaaack! Whaaack! Whaaack! Whaaack! With my hands and feet hogtied to the table, I vainly tried to move my ass out of the way and Chester laughed " Go ahead, grind that ass for me baby.... how's this feel huh?" Whaaack! Whaaack! Whaaack! Whaaack! My fucking ass was on FIRE and my body was wracked with sobs and I was choking on my tears as I let the rawhide chew drop to the floor. Chester came around to my side of the table and wiped the tears from my face, placing his thick fingers wet with my salty tears into my open mouth. I instinctively sucked on each one and gazed into his eyes which had softened a bit. " I think you've received enough punishment for now boy." He came around to the other side of the table where I couldn't see him and gently stroked my inflamed ass, running his thick fingers inside my ass crack, pressing against my unyielding rosebud. " Here... I'm gonna put this back where it belongs." I heard him spit and then he replaced his fingers with something wet and hard and thick. I fucking swooned!! He's going to fucking take my cherry after all! Finally, I will feel a real man's cock deep inside of me. I pushed my ass out against the thickness and POP! just like that my ass was filled. I pushed my ass out to feel Chester more deeply inside me but but met with no resistance. What the fuck??? Chester grabbed one ass cheek in his big hand and gave it a hard twist. " Ok pussyboy, we're done with punishment for now... now it's time for training. Let's get you out of these straps and into the locker room." Damn! It was just the cold butt plug... not Chester's throbbing meatstick . He undid my leg and wrist straps and led me to the locker room, where he sat me down on the same bench Rick Stihl had spanked me on some months ago. The smell of sweat and leather and the stinging of my ass jarred me back to the memory of that stud spanking and plugging my ass for the first time. " Hey hey earth to Bobby...Chester snapped his fingers .... here's a water." " Oh oh sorry, thanks... my throat is raw." " I'm not surprised .. the way my little bro was bangin it" " So why am I training? I thought the deal fell through." " What? I never said that! I said it was none of your business." " None of my business?? Coach, this is my ass on the line we're talking about!" " I know Bobby, and I know how eager you are to lose your virginity and move forward. But remember the contract you signed... you're a Company asset now. I can tell you that the Client drove a hard bargain but Rick and Jake hung tough with a counter offer. Our usual deal is two weeks with the asset but the Client wanted more... he really wants you bad! We settled on three more weeks with you for twice the asking price! That means I gotta tell my little brother he's gotta find a fancier neighborhood and damn is he gonna want to thank you personally!" " So what's this client like? What's his name? I'd like to at least know who's gonna be the first to fuck me." " Sorry Bobby, this is all sensitive information and there's too much at stake to risk it. You'll find out soon enough. Part of the deal is he wants you this weekend, and that doesn't give us much time to get you prepped." I thought about Reggie and his traumatic experience at the hands of the Russian tycoon. " Can you at least tell me what country he's from?" "Sorry Bobby, no can do. Now open your locker and get dressed for workout." Dejected, I slowly opened the locker and expected to see all those glossy's of me sucking the euros' cocks at Black's Beach. It seemed soooo long ago... I stood in shock... the photos had been replaced by newer ones.........
To be continued Stay hard my friends!