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Bad Deal? Gay

 
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Bad Deal? GayThe story started off innocently enough, or maybe not so innocently. My story is not complicated, I am a guy who craves servicing really well hung guys. Long, thick cocks...ones that hang and sway when flaccid and draw admiration when hard and proud. A local internet bulletin board makes it very easy to seek this kind of talent, posting an ad for mutual blowjobs generally will get a fair number of like minded guys to respond. However, there is one small catch...while I am very discriminating in what I want, very well endowed only need apply, I am not nearly so blessed. I fall way at the other end of the curve, a rather thin 4.5 inches. I am a tall, fit good looking guy...early 40's, but really short changed in the shorts so to speak. So, while I could post ad after ad and generally could hook up with the 6 inch and under crowd, the 8 plus inches I craved was not interested in little dicked guys.My most recent ad drew a fair number of replies, and a few interested me with their claims of 7-8 inches. Of course I was a bit skeptical, my own ad claimed 6 inches. But one response was a real attention grabber..., 30 year old guy in gym shape with 10 inches looking for some mutual fun. I didn't believe the 10 inch claim, but even exaggeration left him with 8 inches, right? His reply did have an edge, he bluntly said he wasn't really in to little dicked guys, but a recent dry spell had him horny enough to lower his standards. He enclosed a pic, I double clicked...and OH MY GOD! The pic opened to a rock hard cock, a full fist wrapped around it and still more than half of his shaft bursting forward, crowned by an impossibly large magnificent cockhead. I was instantly uncomfortably constricted in my shorts, and literally short of breath. I took a moment to compose myself, staring helplessly at this huge tool, not even realizing I was rubbing the outside of my tented slacks. I fired off a reply, openly admiring his monster organ, anxious to set something up for that evening. Josh replied about 30 minutes later. He was free later, could use a blowjob. He couldn't promise he would reciprocate, if the chemistry was right he might, but offered a handjob at a minimum. He was willing to play safe. But there was a catch. Josh went off on a rant about guys who lie, how tired he is of guys who claim to have 7 inches that turn out to be five and half. He offered to meet, but told me to 'come clean now' if I wasn't every inch I claimed because 'if there is any doubt, I do measure, I really do. And guys who are even a quarter inch short get thrown out.' I gulped. His second email included another pic, his massive organ propped up by two fingers. Resting on top of his rigid shaft was a foot long ruler with only a shade over an inch extending beyond the bulbous head. I had to have this nearly eleven inch cock, but now would have to confess my bogus claims of average dick size. I sweated and stirred, terribly uncomfortable with my unrelenting hard on and wet spot on the front of my trousers, trying desperately to find a way to minimize my deception and get some of that huge cock. 'Josh-Hey, great, 7:00 works for me, looking forward to it. Great pic you sent. Oh, and about that measurement thing, ok, you busted me. Maybe I'm more like a little under 5 inches, about 4.5 or so. See you about 7.'I hit send, hoping my light hearted approach would still get me in.I checked my email constantly for the next two hours, and dejectedly concluded I had blown it and wasn't going to get a shot at this guy. Finally I heard a ding from my laptop in the next room, I raced to the screen and was overjoyed to see Josh's screen name. 'skip-Normally I wouldn't consider you, but I am out of options this late in the game. If you had been honest up front, I wouldn't have to settle for a guy with a little boy dick. Here are my terms, take them or leave them. I will wait 10 minutes, then I am going out. This is a completely one way deal, you blow me twice. I don't reciprocate, and you don't get yourself off. Period, you are not going to cum, and don't ask or whine about it. If you so much as touch your dick I will throw you out. You will strip at the door, I will be dressed other than pulling out my dick.Be here at 7, directions when I get your answer.'What were my options, I had to get some of this cock, and under the circumstances I couldn't argue with his terms. I emailed back thanking him profusely, praying I didn't miss him. He made me sweat for 30 minutes before the directions came back. Josh's place was a humble apartment building, a long stretch from the affluent sub division I lived in. My Beemer fit in to the space he directed me to, a space adjacent to his older Honda Civic. I found the door and knocked. I knocked a second time, could hear a distant television. Finally, as I was about to leave, the door opened. Josh was a tall, good looking guy, with a cold hard look to him. He gestured for me to come in, the door closed behind me. He pointed to the floor inside the door. 'Put your clothes in a pile there, all of them. Go to the back room and watch the television.' He walked away. I stripped as quickly as I could, I sensed that displeasing him was not a good idea. I hopped as I peeled off my socks, I was very embarrassed by nakedness, but scurried to the back room. On the television was some kind of straight porn, a hugely hung guy was getting an impressive blowjob from an equally endowed blonde bombshell type. I was captivated by the scene, and left alone standing in front of the huge screen had little else to do but watch. I had no idea where Josh went. As the blondes head bobbed and her balloon like tits bounced the guy with the gigantic dick moaned, but seemingly could last forever. I wouldn't give myself a chance of lasting past 30 seconds under similar circumstances. To my horror, I realized that my cock was also taking notice of the scene, and I was now standing naked and fully hard. So hard I desperately wanted to give myself a few strokes, and it took all of my self control to keep my hands off my throbbing erection. Just as I was about to give in and grab my aching cock, Josh came in and sat down on the leather couch. He continued to ignore me, leaving me standing in the middle of the room embarrassingly erect. Josh's jeans and t-shirt left me feeling exposed and humiliated, his insistence on ignoring me had me frustrated and puzzled. Finally he spoke, but still refused to look away from the television. 'Here's your deal, no negotiation. You will do what I say, when I say it. You will not touch your tiny dick under any circumstances. Now, kneel on the floor here in front of me.'I scrambled to my knees in front of Josh. He took my hand and placed it on his jeans, the outline of his huge hose was clear, when my hand my came in contact with it through his jeans I gasped, and my tiny cock jerked and leaked.'You are going to do this bareback...you lost your condom privileges when you lied to me.'I could feel his huge cock swelling through his jeans as he held my hand against it. He pulled my hand away, I audibly moaned with frustration. Josh unfastened his jeans and unzipped. He lifted the waistband of his briefs and glanced inside, he knew how desperately I wanted to see what the briefs contained. His right hand disappeared in to his briefs, and he tugged his floppy tool so it almost peaked out of his briefs, clearly outlining all of it under the white cotton. 'My god' I gasped, it was much larger than I imagined. My cock was nearly vertical, purple, and leaking steady pre cum. I desperately needed to stroke it, to touch it, anything at this point. Once Josh told me I was sucking him bareback I should have left, but he knew I was too far gone to say no. Little did I know our negotiation, if you can call it that, was not over.'Are you in agreement with everything so far skip?''Yes Josh' I gasped, my voice husky with desperation.Josh smiled slyly as my answer told him what he already knew, he could demand much more.'Finally, this is not a one time deal. You are going to sign up for six sessions, same deal each time. I call you, you come here and strip, you suck me off, then you leave with no relief. As insurance on your agreement we are going to take a few pictures now that I might delete when you complete your contract.'I looked horrified, but Josh pushed on.'You have a choice right now, you can get up and get my camera off that table over there, or you can get up and dress and leave.'I opened my mouth to protest, but Josh shot me a look, and began to zip up his pants. It was clear that speaking would end my chances of getting that 11 inch cock in my mouth. Josh knew what choice I would make, and enjoyed every moment of the collapse of my dignity as I walked to the other side of the room and retrieved the camera. As I walked back Josh stared at my hard as iron cock. 'That looks really uncomfortable. Bet you wish you could do something about it, huh little buddy. It must suck to have a little dick, huh?' I blushed crimson, and handed him the camera. 'Oh, can you get the ruler that's on the table too.' It didn't take a genius to know what the ruler was for...Josh started out tamely enough...full frontal with no pretense of avoiding my face, side angle, back. He disappeared in to the next room for a few minutes, I didn't dare sneak a few strokes while he was out. 'Ok, those are downloaded, now for the fun shots.' Josh had me hold the ruler next to my dick, documenting my 4.25 inches with pic after pic as he laughed. Next he bent me over for close ups of my hanging balls and ass. I had no choice but to comply as he made me spread my ass cheeks, and look back between my legs at the camera. Now thoroughly degraded, Josh again disappeared to download. His now rigid shaft shown clearly through his jeans, tipping his hand of his intense enjoyment of this humiliation ritual. From the next room, presumably at his pc, he shouted 'Wow, these are great, you're really my bitch now.'The reality of my situation put me in a fog, Josh's non-stop chatter about my completely compromised status drained all pleasure from what I arrived there to do. Josh laughed when he finally pulled out his semi rigid dick and taunted me through the first blowjob. I gagged at barely the halfway point, but fairly quickly coaxed a huge load out of him that I knew I had to swallow. 'You better practice at home skip, none of these blowjobs count toward your debt until you can take all of me down your throat.' I couldn't imagine being able to quell a gag reflex well enough to take all of that monster. 'Hey, chicks do it, and they aren't as motivated as you are.'I blew Josh one more time that night, and at his insistence begged for permission to jerk off, knowing it wouldn't be granted. He continued to laugh as I had to dress around my rigid erection. 'You know that guys with average sized dicks don't have to take this kind of shit don't you...' As a final goodbye he reached between my legs and gave my balls a hard squeeze, then pushed me gasping out the door, knowing I would have to drive home with throbbing balls.As I type this I continue to practice trying to deep throat a cucumber, after five sessions at Josh's apt I have yet to successfully deep throat him..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 he is even slower and harder the second time.Worst of all, I have not paid down my debt. Well maybe it's the bad deal, or it could be my best deal ever made.
04-15-2021, at 01:12 PM
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