Bad Deal Ch. 02byskip5236©
The essential elements of this story are true, but the names have been changed to protect the not particularly innocent.
I had visited Josh's apartment five times, the pattern changed very little each time. I would arrive at this place; Josh would say nothing when he opened the door, it was understood what I was required to do. I would strip at the door, leaving my clothes in a pile, then walk to the 'playroom' as he called it. Always waiting for me in the playroom was his big screen TV with another selection of his seemingly endless porn collection playing. Josh knew my weakness, and the television always featured huge cocks, huge tits...and always had the desired effect. Josh would leave me back there for ten to fifteen minutes, by the time he finally joined me I would be embarrassingly erect. There is something incredibly humiliating about being naked with a throbbing hardon when the other person is fully dressed. It makes it pretty clear who is in charge.
Josh had not relented on his hard ass stance, he once again told me that I still owed him six sessions and that number would not go down until I could deep throat every inch of him. He still refused my requests that he wear a condom, I didn't ask after the third session when he used the ruler to administer two very painful slaps to my hard dick, raising an ugly bruise the next day. I had no choice but to swallow two loads every visit, even the second one was remarkably large. He clearly enjoyed forcing me to submit to him, every visit included 'picture time' with Josh dreaming up new humiliating poses as I his flash ensured my compliance. And every session ended with a knee buckling squeeze of my balls. I pleaded with Josh to skip this step every time, hoping my performance in the playroom would earn some mercy. It had no effect, as Josh would steadily tighten his squeeze on my nuts he would lecture me about lying to him about my tiny cock as I would clutch his wrist and gasp for air.
Finally my training at home was paying off. I had begun practicing with a carrot, pushing it further in to my throat until my gag reflex forced me to stop. Finally I had managed to get the 11" mark to my lips and held it there, giving me hope that I could finally handle Josh's thicker tool. When Josh's next email arrived mid-day on Wednesday requesting that I be at his place at 7 I hoped I could finally get my first installment credited.
I arrived at Josh's apartment at 7 sharp, and as usual stripped at the door. Uncharacteristically Josh stood and watched. When I tossed the last of my clothes on the pile I stood and looked at Josh, not knowing what to do with him standing there. Josh was staring at my completely limp dick...'Wow, it's really small when it's soft'. I blushed despite myself, it was the first time he had seen me without at least a partial erection. 'Go get the ruler, and keep it limp' he ordered. I scurried off to the playroom, and returned with the ruler with some trepidation as the ruler at best was a humiliation tool, at worst was used for discipline. "Prop it up with one finger, I don't want to touch it' Josh directed, his tone having a thick hint of disdain. I couldn't help glancing at the clear outline of his cock in his jeans, and recalled the many times he had pointed out my 'flat front' to my own slacks. 'Two inches' Josh announced with a chuckle. 'Be honest, how many times has someone looked at that puny thing and said no thanks'. 'A couple of times' I mumbled in shame recalling both the women and men who had subjected me to the ultimate emasculation. Josh spared me further shame by pointing to play room, I walked back briskly.
The television was on as usual, the usual fare. I tried desperately to keep from getting aroused, but it was hopeless. As usual Josh arrived about 10 minutes later and my four an a quarter inches were well north of horizontal with a small drip of precum formed on the tip. Josh pointed to the floor at his feet, and settled in to watch. I knelt and waited, transfixed by his straining crotch as the denim struggled to contain his flaccid hose. After a long wait, Josh unsnapped, zipped, and tugged out his huge cock. Even after all the sessions, I still draw a sharp breath when it first flops out on the front of his jeans. Josh signaled for me to start, and chuckled as my first touch of his shaft was accompanied by a sharp jerk in my own tiny cock, with a strong surge of precum. At this point Josh starts a steady dialog about my desperation for relief, taunting me about how I can only look at my drooling dick, how badly I must need to stroke it, how pathetic I am that I have to give up my own orgasm to suck another guys cock. He loves to make me tell him in detail about the discomfort both in session, and that lingers on well after.
Josh is not only blessed with a freakishly large cock, but incredible stamina. As I used both hands to hoist his heavy, limp shaft he barely reacted. I immediately set to work with my tongue and my hands, caressing, licking, suckling his huge head. Very, very slowly his tool thickens, achingly gradually it straightens, painfully slowly the head fills and plumps to impossible proportions, then gets even larger. By now my knees ache on the hardwood floor. By the time Josh reaches full erection my whole body has a sheen of sweat. Josh loves to taunt me about how hard he makes me work just to get him hard, knowing full well he is still a long, hard working session away from orgasm. He loves to point out the state he puts me in...he is cool and comfortably relaxed, I am soaked in sweat and cramped with aching knees; he is barely turned on, I am panting and puddling precum on the hardwood floor beneath me. This amuses Josh to no end. He loves watching my drooling aching discolored cock, knowing my arousal is steadily breaking me down and tormenting me. He ridicules how hard I have to work to get him barely aroused, while I am in a panting frenzy with a puny cock that has NOT BEEN TOUCHED!
Finally, with Josh fully hard comes the moment of truth, and I realize at that moment I have no chance of success. Staring at his hard shaft, thicker than my practice carrot but maybe manageable, I realize I have not taken in to account the size of the huge head, which approaches the size of a small apple. I have no chance of opening my throat to accommodate that massive bulb that now rests on his stomach well above his navel. With both hands I grasp the base of his shaft, neither hand wraps fully around, and tip the head toward my mouth. I am forced up off of my knees to get up over the top, and stretch my mouth over his head. As I slide about six inches in my fears are confirmed, as his head corks my throat opening, and any attempt to proceed is futile. Josh realizes only now realizes that I had hoped to make the breakthrough today, and laughs at my pathetic attempt and complete failure. Clearly incapable, I sadly resort to what he has come to call a 'half cocked blowjob', referring to the portion of his shaft that stays out of reach. With a now established pattern of mouth, hand and tongue I induce Josh to unload his first cumload at the back of my throat. Aching and sore, I know the process starts over again in about 30 minutes, and is even slower and harder the second time.
Worst of all, I have not paid down my debt.