Bad Deal! (Gay Themes)
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The 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 dick 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 sceptical, 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 dick 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 cock head. 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 realising 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 minimise 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 realised 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 pretence 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 hard-on 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 practising 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 instalment 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 signalled 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 discoloured 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 realises only now realises 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 cum load 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.
Let me start out by saying Skip is not special…he is convinced that he somehow bumbled in to his predicament, but honestly he followed a well designed path that yields the same result every time…a guy naked and on his knees, his dick is hard and drooling, and he is agreeing to everything and anything I tell him to get his mouth on my dick. Nothing about his experience was spontaneous, unintentional, or unique to him from my perspective.
First, about me…I am a regular guy, I am bi, and I do have a huge cock. It is about 10.5″ hard; it reaches well past my navel and is so thick I can’t get my hand around it, not even close. When I am with women I am a normal, very patient and passionate lover. The patient part is mandatory, with a dick like mine you have to take it real slow and easy. My only quirk when I am with a lady is I will admit I love being in a good position to see their reaction when my huge hose flops out of my pants…whether I am standing or they are kneeling, I like to see their look of awe and raw lust when they see it for the first time. But otherwise, what I want is good, straight, vanilla sex.
With guys it is a completely different story. The only thing that makes me hot, the only way I am interested in pulling it out for another guy, is when I can force him to completely, totally humiliate himself in hopes of sucking me off. Call it primitive and evil, but completely emasculating the other guy, forcing him to admit his inferiority and then pushing the envelope as far as I feel like is what makes me hot.
So back to Skip. Skip was an absolute prime target. His emails were completely transparent; he is a class A1 big dick hound. Every guy on the net exaggerates his dick size, and Skip’s claim of six inches had me rounding down to five. When I spun my web, sent him the pictures, I knew by the tone of his emails that the hook was set real good. That’s when the game starts, because I know that a guy sitting at a keyboard with a hard on staring at pictures of my cock is pretty helpless. When he admitted his deceit, as I force all of them to do, and conceded he was closer to four inches than six, something in me clicked and I decided to give him the full treatment.
Skip is a good looking guy. Tall, thin and athletic looking, kind of preppy, fortyish. He is looks like a successful guy. When he arrived at my place I had my game face on. Friendly enough in a cold, detached way. I don’t want them to be afraid, but I want to keep them off balance and establish right away who is the boss. He arrived at the door having already signed away his orgasm. Unless I am feeling generous, I usually operate by a 5″ rule. I tell every guy that he is signed up to suck me off twice, and I don’t reciprocate. What I tell them next varies. If a guy is 5 inches or more I tell him he is free to jerk himself off, usually I insist they go to the bathroom to do it. The little dick guys, guys under 5 inches, I am particularly cruel to…they know up front that the deal is completely one way. They service, they get really hot and desperate to cum, and they leave that way. While they all know that deal coming in the door, every guy thinks I will change my mind and let them jack off in a post orgasmic moment of weakness. So Skip and his 4 inches came in the door having agreed to leave frustrated.
Skip stood awkwardly at the door while I appraised him silently. I let the silence linger uncomfortably; I always catch them sneaking a peak at my crotch. Finally I direct them to strip right there at the door, clothes in a pile on the floor. I always stand and watch, this is the first step in their humiliation. A guy never feels as naked as he does when the other guy is fully dressed. About half of the guys are already semi-erect at this point, they always pretend not to notice. Skip fell in to the other group. As his clothes fell in to a self consciously neat pile it was obvious he wasn’t looking forward to baring his dick. He turned his back as his Jockeys slid down, and finally turned to face me but wouldn’t make eye contact.
Skip has a nicely shaped dick. Nicely proportioned, straight, well formed head. However, it is the smallest dick of any guy I have put through this treatment. Completely flaccid, it appears to be about 2 inches. Part of me was fascinated in an anthropological kind of way, but my more primitive self was deeply affected. I almost felt an indignation, a need to truly punish this guy who so ardently pursues well hung guys, knowing full well that what he is offering in return is a very poor trade. Skip needed to learn a lesson. I directed Skip to the playroom to be fluffed.
Every guy spends about 10 minutes in my playroom waiting for me, mostly to reinforce who has the power. All of them are naked, and all of them are told to stand while they are waiting. I have a 60” television in the playroom, and I always have some very hot straight porn playing. Lots of huge cocks and big tits flopping around, and the result is always the same. After a good wait, I always walk in to the playroom fully dressed and find a guy standing awkwardly in the middle of the room now sporting a full erection. If it is humiliating to be naked in front of a fully dressed guy, standing in front of him with your dick hard is borderline painful for most guys. It really reinforces who holds the power in the situation.
Skip was in worse shape than most guys at this point. I walked in to the playroom, and it took all my self control to stifle a laugh. Like most guys, Skip was standing awkwardly in the middle of the room. I had made him wait a little longer than most, and it clearly paid dividends. Skips cock was now stretched to its maximum length and breadth, painfully hard looking and twitching. It pointed well north of horizontal, and had an abundant glistening drop of pre cum. He had a slight flush to his pale skin, and his breathing was noticeably a bit heavy. I flopped on the sofa and asked him if he enjoyed the movie, pretending I hadn’t noticed his rigid cock. His voice was hoarse and thick with need. Even fully engorged, his cock is startling for its small size. Eventually my curiosity couldn’t be contained, he measures about 4.25 inches.
It is at this point that, from my perspective, the fun really begins. I am sitting on the sofa wearing a pair of jeans that snugly highlight my thick cock, knowing that guys like Skip have radar lock on my package. I torment them just a little bit by continuing to ignore them in their uncomfortable state as I watch a little of the movie and allow my dick to plump up just a little. Now is when I go for the jugular…now is when I start reaping the benefits of putting a guy like Skip in such a desperate state that we both know he will do anything I demand to earn access to my cock.
First I need to continue to reinforce how completely one sided this arrangement will be, and my rule that forbids him from touching his own cock is very powerful that way. Every guy reacts the same way as I coolly inform him that if I catch him touching his cock at any time I will shut this whole thing down right away. They all can’t help but to glance down helplessly at their painfully rigid dicks, and in the same way an itch you cannot scratch is so maddening, realize a desperate need for even just a couple of strokes to help with their frustration. Skip was no different, but he actually let out a small but quite audible groan as a drip of precum strung downward and mumbled a commitment at my insistence that his dick was off limits.
This is when I diverged from my usual ritual, and decided to try something I had always fantasised about. Skip was clearly so aroused at this point that he could be abused to a degree that I had longed to try, and immediately decided this was that opportunity. I dropped the bomb on Skip…he was on his knees on my hard floor thinking that this submissive position clearly was the path to my dick. How wrong he was…I lectured him for his dishonesty about his size, forcing him to apologise repeatedly and dramatically described how angry I was that he was my only option for a blowjob when there were lots of hung guys out there. He flushed when I informed him he would be sucking me bareback, that his lack of honesty didn’t deserve ‘condom privileges’. His esteem badly battered, but his erection unrelenting, I went for it. I told Skip he would be signing up to service me not just this evening, but over six sessions, take it or leave it. To ensure his compliance, he was to retrieve my digital camera so we could get some photos of him in his aroused and submissive state.
Skip clearly looked panicked. While he had resigned himself to pretty much take whatever humiliation he had to endure, handing over such powerful control which would endure beyond being used and abused this one evening frightened him. From his knees, his head only a foot from my denim clad crotch, he sputtered but continued to stare at my bulge. His hard-on twitched and bounced helplessly, clearly enslaving his thinking. I slowly unsnapped my jeans and drew my zipper down. Skip’s mouth hung open, he was literally panting and unbeknownst to him his hips were humping in a slow rhythm. I pulled up the waistband of my boxer briefs, reached in and hefted my thick cock up from my pant leg and left it lolling sideways covered in cotton. The outline extended to my hip and the girth stretched the briefs obscenely. Skip knew better than to attempt to touch what he so desperately craved, and let out a brief muted wail of frustration. I knew he was broken.
“Skip, the camera…or get dressed and leave.” Skip climbed to his feet, it was clear that getting dressed was not an option. As he walked to the far side of the room his tiny cock swayed side to side, in his state I am sure even that swaying created debilitating need for relief. I made no attempt to make this easy for him, it was clear my chuckling was delight with the collapse of his dignity. He walked back, head down and handed the camera to me. I forced him to ask me to take the pictures, then made him retrieve a ruler so we could document his puny cock that now drooled steadily.
The photos started out pretty straight forward…full frontal, side view with instructions that made it clear that his face was clearly in the picture. We put a ruler on his dick as I began forcing him to admit that a guy with a 6 inch dick would never have to tolerate this kind of degradation. His ass and hanging balls gave us a nice set to start my collection.
Skip did spend much of the evening on his knees on my hard floors. I didn’t allow him to retain any dignity as performed for me, pleaded for my cock endlessly, and went through several more rounds of photos that are safely filed on my computer. Ultimately, he did get his reward, and did demonstrate very good oral skills as he brought me to two powerful orgasms. I cruelly held off my second orgasm for a very long time, enjoying his sweat soaked exhaustion, aching jaw and knees as he slobbered over my huge tool. Even in his depleted aching state his own cock never showed any mercy, and he begged pitifully for relief from his tiny erection. The collapse of his self esteem was so complete, his begging for the right to masturbate so humiliating, that I was nearly inspired to demand a third session on his knees…