After the meeting with Jim and Laura described in Chapter 3 I continued to meet with them on a regular basis. A process evolved where I would email Laura and ask if I could visit, and she would set the time. Eventually we settled in to a rhythm of meeting every couple of weeks. The deal stayed the same as what Laura laid out, I paid $50 plus the two packs of cigarettes each time. They always required me to wear a condom, and other than a brief hello I had to strip immediately when I arrived. As time went on things did relax a little and they weren't as harsh with me, we did become more fr... Continue»
My meetings with Jim had been going on for about 5 years. In hindsight, it is amazing to me how much he had changed over that time. Five years ago he was an average looking guy with a bit of a belly who was bi-curious, and had no idea he was seriously hung. Chalk it up to being a grower not a shower, but his full 8 inches were really only the beginning of an incredible package, it was the nearly thick as my wrist shaft and huge incredibly well shaped cock head that made him world class in the cock department. And he had no idea. Our first meeting was supposed to be two guys meeting up to swap blowjobs.
Now five years later Jim is very different. His transformation really began when he and I met, and was driven by his cleverly malicious girlfriend at the time, Laura. She fully supported his exploring his bi interests, but immediately saw an opportunity when she saw my less than 4" cock, and the effect Jim's monster cock had on me. Laura told me months later that her number one turn on is using men's desperation for sex to humiliate them. Laura quickly set up a structure for my relationship with Jim that remains the basis of how he and I interact to this day. She instinctively knew that I would be willing to pay a very dear price for access to Jim's cock, and dictated the terms. She structured a total one way deal and total submission, knowing full well small cocked guys don't get the time of day from guys who are much younger and real well hung. So it was her idea that not only wouldn't Jim reciprocate, but I was not allowed to cum during a session. It was her idea that I strip naked at the door, and arrive fully erect. It was her idea that I wear a condom to avoid leaking strands of pre-cum. But most of all it was her idea that I pay Jim a fee, set initially at $50 and never really varying from that, to be allowed to get Jim off.
Ironically, all of this evil intention on Laura's part worked too well. While I am sure she smiles to this day knowing Jim has taken thousands of dollars from me over the years for the right to give him hundreds of orgasms, every time ending with me leaving his place with an achingly hard cock that badly needs relief, it ultimately backfired on her. At some point early on, a switch flipped in Jim. Somewhere deep inside his dominant nature was unleashed, to the point that Jim now freely admits he can only get hard with someone who will do anything for him out of desperation for his cock. Laura and Jim split up about a year after I met the two of them, but within six months Laura couldn't deny how much she missed his huge cock, his ability to cum over and over, and never ending stamina. She tried luring him back to a 'friends with benefits' arrangement of regular fucking, only to find a cold disinterest that could only be broken down with begging and total submission. Her DDD's that could enslave lesser men failed her for the first time, and now Jim has her groveling for his cock the same as me and many others.
So here we are, almost 5 years later. Regular meetings, at least monthly and often twice per month. On a couple of occasions I tried to quit, usually because I would get disgusted and burned out on paying him. The reasons are complex, it isn't just that it is humiliating to have to pay another guy to get him off however he chooses, but Jim also regularly reminds me that the other guys he meets with don't pay him. So more than once I have become disgusted and tried to give it up.
Jim had long ago set an expectation that I would visit at least monthly, making it clear that he wanted to be able to count on the money. In fact on a couple of occasions he subtly made it clear that he expected to be paid on months where schedules didn't allow us to get together. Nothing too obvious, but when I was anxious to get together after more than a month without his schedule suddenly got problematic, problematic until I had no choice but to offer the previous months fee with the normal fee I had to pay to get his zipper to come down. So a couple of times I did try to quit. I told him each time I needed to find a way to stop; I was respectful and didn't just disappear. Each time he was amused and condescending, immediately laying out what his expectations would be when I broke down and came back. The terms were pretty simple, I would have to pay the fee for each month I missed and should expect to be wearing panties for a long time in future sessions. Each time I would start out determined and convinced I could do it; eventually I would find myself masturbating regularly thinking about his huge hard cock, inevitably sending him an apologetic email asking to be allowed to visit him again. Once I made it 4 months. Jim thoroughly enjoyed watching me kneeling in front of him naked, my small cock hard as steel, as I counted out $200 for the months I had missed, then counted out $50 more for that day and began begging to be allowed to service him. Only later would I come to understand how seriously he took the money aspect of our business.
On two occasions I even tried to find a replacement for Jim.
Each time I found myself hunting for something that described Jim to a tee...about 10 years my junior, hung long and very thick. I described myself as fit and little younger than strictly accurate, added an inch to describe a 5" well shaped cock and was more than willing to do a no reciprocation deal for the right guy. I met up with a couple of guys, each one had supplied picture proof of large, powerful cocks, and each one then insisted on a live meeting to check me out. While the details were a little different each time, the result was always the same. I met this one guy Steve at a local shopping mall. We sat in the back of his very private van to talk, and he quickly directed me to fold all of my clothes neatly and put them on the front passenger seat. Steve, a good looking guy in his mid-30's, was fully dressed and it was obvious he intended to stay that way. He was looking for a 'regular guy', someone who was available at his whim to strip down and provide a very long, slow patient blowjob. His requirements were consistent availability, stamina, and an understanding that he doesn't want any jerking off or stroking of my cock at his place. 'Last thing I need is you getting too excited and having an accident, guys are useless after they cum' was how he put it. I tried to play it cool as we talked, but my cock kept getting progressively harder and I was helpless to stop it. By the time Steve finished describing what he was looking for I was fully and embarrassingly erect.
'So that's 5 inches huh' Steve asked with both clear skepticism and amusement.
I knew I was stretched out as long as it could get, and hoped the missing inch or so wasn't obvious, but it clearly hadn't fooled Steve. 'Almost' I mumbled.
'I guess most guys with little ones lie a little, huh?' he asked with clear disdain. He let the silence hang painfully, making it clear he expected me to admit the obvious.
'It's almost 4 inches' I said in a low voice, desperately trying to find a place to look as I avoided looking at him, but didn't want to just look down at my bobbing cock. However, I couldn't help noticing, to my horror, a large well formed drop of pre-cum had formed at the end of my cock. Steve clearly noticed too as he chuckled.
'Can we get to a real number, or are we going to keep playing games' he said impatiently. By now the whole dynamic in the van had changed. I probably was trying to deny the obvious when I stripped down at his direction, but Steve was clearly in charge now.
'3 ¾"' was all I could say in a low voice. The drop of pre-cum started to string downward off my cock, I was paralyzed by the humiliation of the situation.
'Take care of that, I don't want it on my seats' Steve directed sternly. I scooped it up awkwardly with my fingers, but sat there awkwardly with cum streaked fingers. Steve was losing patience. 'Let's go, put it in your mouth' he snapped. I did as I was told.
While the 'interviews' were all different, one guy actually put a ruler on my cock and had me read my measurement to him, they always wrapped up the same way and Steve was no different.
'Ok, so let's talk about how the money will work.' Up until now there had been no reference to money in any email or discussion, but as one of the guys told me pretty bluntly 'Older guys with little dicks don't get in the game without cash. There are plenty of young guys with six packs who will give no recip blowjobs if you have a big cock, so saying you will do no recip doesn't get you anything.'
Steve proposed that $20 an inch sounded fair, so sucking his 8" cock would cost $160. I tried to counter propose that I pay $20 for each inch of difference between my cock and his, and proposed $80 would be a fair result.
Steve laughed at my math for starters, pointing out I don't have a 4" cock so my proposal is actually $100. 'The only reason I care how big your dickie is because I know guys with 3" cocks don't get guys with 8". I'm not going to let you pay for the difference because I'm never going to touch your dick.' In every interview, sooner or later we got around to an expectation of a fee being paid.
I did pay Steve that day, it wasn't $160, he took the $120 I had with me and when he lowered his jockeys an impressive cock was revealed. Long, medium thickness with a proportionate if only a little undersized head. In other words, he wasn't in Jim's league.
So, inevitably, I would return to Jim every time.
While we had developed a friendly rapport, Jim and I weren't friends, and our roles in the relationship had become very firmly established. He was affable and pleasant, but was very clearly in charge. It was understood that I would treat him with deference and complete respect, and by now it had been several years since I had called him anything but Mr. Smith. I always paid him as the very last thing I would do when I was leaving. I was always dressed and ready to leave, with my slacks clearly tented by my hard dick, but early on he had made it clear he expected very enthusiastic and sincere thanks when I gave him his fee. That might have been the single most difficult requirement in each meeting, all I can think about is how badly I need to cum and ease my aching balls, and I am handing him cash and thanking him knowing his huge cock is hanging limp and satisfied after a couple of quality orgasms.
The rules of our meetings had changed very little over the years, and had settled in to a ritual that was understood and comfortable to both of us. While at one time he had forbidden me to email him and ask for a meeting, he had softened on this rule and generally now it was me who initiated setting up time. Usually he permitted me to meet without requiring me to wear panties, only occasionally did he re-establish this rule if I had displeased him by having to cancel a meeting or not visiting him as often as he preferred. But when his email saying we could meet included a color choice for the thong panties I had to wear, the message that he wasn't pleased was loud and clear. But the core ritual remained the same for each meeting.
First stop was a local Walmart where I would buy the panties if required, one box of 12 Trojan Magnums, and a package of 3 Lifestyle snugger fit condoms. All of these purchases needed to appear on one receipt that I had to give to Jim with his box of Magnums to prove I bought both sets of condoms at the same time. And yes, if you are wondering, you do get an occasional odd look when you are buying two sets of different sized condoms at the same time, and I have little doubt that the clerk can guess which box is for me. In the parking lot of Walmart I would wriggle out of my pants and Jockeys, pull on the thong panties and awkwardly pull the pants back on. And yes, embarrassing as it is I do generally get hard putting the panties on.
Stop number two is a Dunkin Donuts near Jim's home. I always go in so I can use the men's room. Jim doesn't allow me to use the bathroom at his house, so I take a nervous leak so my bladder is completely empty. I order Jim's coffee...large iced coffee, light with six Splenda. Summer or winter, doesn't matter, iced coffee it is.
Stop number three is a small shopping strip mall right around the corner from Jim's home. I park in the far corner of the parking lot and carefully watch the clock until it is exactly 10 minutes before our meeting. Jim has always insisted on strict punctuality. At 10 minutes to I unzip my fly and begin rubbing my cock through my underwear, stroking to the full erection that Jim requires when I arrive at his door as a show of respect. Usually this isn't difficult, though sometimes the stress of all of my chores and racing to arrive on time keeps me stubbornly limp, but somehow I always manage to get to my full 3 ¾" in time. Fully fluffed, I drive the quarter mile to Jim's home with one finger tracing my erection to keep it fully hard.
So just like any other month, I had emailed Jim two days ago requesting a meeting. He sent back a time when he was available, and had suggested I wear black panties. I was surprised because I couldn't think of any reason why he would be irritated with me, but I suspected he was just doing it to reinf***e his power. He knows I hate having to slip in to the lingerie department and find panties that match his request, then arrive at a cashier with boxes of condoms and panties. For the same reason he often likes to tell me to pick up some things on the way, mostly because he enjoys reinforcing that I have to do it. Usually they are mundane things like a twelve pack of soda or cigarettes for one of his girlfriends who wears a DD bra. Today's meeting had a new quirk. I had emailed the day before and asked if we could meet the next morning. Jim had instructed me to bring an additional box of 6 Trojans in standard size...so three sizes of condoms all on one receipt. I had followed his instructions, and clearly got an odd look from the Goth like 19 year old chick behind the counter as she scanned box after box of condoms and a black satin thong in size XL. I half expected her to ask if I had no idea how big my dick is. I assumed his request for regular sized condoms was so he could replenish his supply for his hung average friends, Jim has always enjoyed reminding me that I buy his condoms for the women and other guys he sees, hence the requirement of the 12 pack when he only uses one or two with me. So making me buy condoms for other guys I figured was just another way to screw with me.
Our meetings are always first thing in the morning, Jim has several extremely busty women friends who he sees regularly in the early afternoon, so he slots me in to early mornings so he can recharge after having me get him off a couple of times. This can often make the morning errands stressful, especially if he adds a few things to the list, but Walmart opens at 7 so I always get it all done. So like any of many, many meetings with him, I arrive at Jim's precisely on time, finger working the length of my hard cock, parking out in front of his home. I knew from experience that there would be a quite noticeable wet spot in the black satin, and the thong back had worked its way in to my ass in a way that I was now quite used to. Today I had forgotten to check if I had exact change for Jim's $50 fee, arriving with three twenty dollar bills means I will be paying him $60 because the thought he would give me $10 back is laughable. So I shuffle through my bills quickly and am relieved to find a twenty and three ten's. I gather the Walmart bag full of condoms in three sizes, give my cock one last stroke knowing once I get out of the car it will be off-limits, and grab his coffee and make my way to his door. Hands full, I push the bell with my knuckle of my hand holding the condom bag, though more than once I have amused myself by wondering if my hard dick could make the uncommonly low doorbell button depress sufficiently to alert Jim I had arrived. Likely it could.
Jim arrived at the door in his usual attire for one of our meetings...a baggy pair of sweat pants and a faded old t shirt in stark contrast to my being dressed for work.
He is always friendly enough in a superior sort of way, offering an indifferent 'Hey Skip' at the door in a ritual that begins our now standard opening conversation.
'Hello Mr. Smith, thank you for letting me visit.' Is my stock answer. I always, even after all these times, feel a little awkward and stressed at this point, much of it probably a result of being incredibly horny and having a full erection. I hand Jim his coffee with a mumbled 'I hope it's the way you like it'. He would never thank me for it or show any kind of gratitude.
There is a chair to the immediate right of Jim's entrance door, and it is well understood that I will immediately strip down, neatly folding my clothes and putting them on the chair in a precise pile, with my shoes on top of the pile. I hand Jim the bag full of condoms and hurriedly start to get undressed. Jim gets impatient if I take too long, and is very critical if I don't fold and stack my clothes neatly enough. But today he is quite pre-occupied studying the receipt and the boxes of condoms. As usual I can hear a television in the background, Jim usually has porn on the television when I arrive, I often wonder if porn just plays 24/7 here.
Jim is still studying the receipt for the condoms. 'These things are expensive,' he exclaims with a low whistle. 'Glad I don't have to buy them.' By now I was finishing folding my pants and putting the shoes on top of the pile, and chose to ignore the unsubtle little zinger, but he kept going. 'You know, I have always been surprised that your size condoms and mine cost about the same amount. Wouldn't you think mine would cost a lot more?' Jim was only getting warmed up. 'It does make sense the standard size costs less, there is more demand. I guess there are very few guys who are magnum size, and even fewer who need these fitted things. Look, you can tell, the box for the fitted ones is even a little dusty.'
Jim seemed to be consumed with the thought, but then snapped out it and looked down toward my pre-cum soaked panties. 'Pull the waistband down under your balls, let's head back.'
Head back meant toward the back bedroom, which is down the hall and through his f****y room. The waistband command was new, usually I just wear the panties back to the bedroom, then he has me take them off right away. But it became habit a long time ago to just do what Jim tells me to do, so I slipped the waistband under my balls as instructed and started to follow Jim to the back of the house. There is some odd and embarrassing about walking when you have a full hard on. It juts out and bounces, and makes it clear that you are aroused. It gives the other person power because there is no hiding that you want it. I couldn't help glancing down, and to my horror saw a string of pre-cum starting downward from the end of my cock. I was in a panic. Jim gets very angry if I drip pre-cum, generally when we get to the bedroom he has me put on my condom so I don't get pre-cum on anything, I do tend to flow pre-cum heavily. But his strictest rule is that I cannot touch my cock when I am at his place, so I didn't dare reach down to stop the string. The only exception to the 'no touching your cock' rule is when I put my condom on, and Jim always watches carefully to ensure there is no excessive handling involved. So the string kept extending toward the floor and we kept walking toward the sounds of a woman delivering a blowjob emanating from the television in the next room.
I was very distracted by my leaking cock which explains why I almost ran in to Jim's back when he unexpectedly stopped in the f****y room, though the near collision did solve one problem when my jutting cockhead wiped on the back of his sweatpants. Jim had no idea that he helped me out, but was quick with a snappy line....'Yeah right Skip, with that tiny cock you will always be on the receiving end of that kind of action...'
The f****y room in Jim's place is, like the rest of the house, untidy and poorly furnished. Laundry and dirty dishes are part of the decoration in every corner, and piles of stuff are everywhere. The f****y room is dominated by one large recliner that I have always thought of as Jim's throne, and have spent a great deal of time in front of it on my knees. A plaid sofa sits next to the recliner, and both face an old style 50 inch or so projection television. It really is appalling how bad the picture quality is once you have become accustomed to today's high definition flat screens, or maybe it is the poor quality of the DVD that is playing, but the balloon titted blond bobbing on a huge prick still grabs your attention even with the cheesy soundtrack. So, as my head involuntarily swiveled toward the screen I was stunned by what I saw.
There, sitting on the ugly plaid sofa watching the big titted bleach blonde, was another guy. I was probably standing three feet from him, directly behind him, with my stiff cock pointing right at him at head height, and my balls presenting nicely forward courtesy of the panties tucked under my balls. In all my meetings with Jim there had never been another guy present. In fact, not since our early meetings when his girlfriend Laura used to watch, there hadn't been anyone else in the house when we met. But there he was. Of what I could see he was an average looking guy, 30's and an ordinary soft body type, wearing the same sweatpants and t-shirt uniform Jim was wearing. Looked like he was accustomed to long hours on plaid sofas. But I could only see so much.
Jim spoke. 'Hey Bill, this is Skip that I told you about.' God only knows what he told him, but since I am meeting this guy Bill in a black thong with a hard on, what is there left to tell? 'Skip, this is Mr. Taylor.'
Bill looked up briefly at my face, but quickly locked on to my thong supported cock, hard and horizontal and beginning to form another pre-cum drop. Bill laughed loudly and spontaneously. 'Hey Skip.' Bill briefly looked away from my drooling cock. 'You weren't k**ding; he really is your bitch isn't he. You weren't k**ding about his dick either, that thing is ridiculous!' I don't know if I have ever felt more awkward, more naked, than I did at that moment. Meeting a fully dressed guy when you naked and erect is horrifying I was learning.
There was an awkward silence, finally Jim spoke. 'Skip, where are your manners, can't you say hello.'
I had no idea where to look; I was mortified by the whole scene, but couldn't just stare at my feet because the 3.5" object of Bill's amusement was in the way. 'Hello Bill.'
Jim quickly snapped the back of his left hand in to my balls, not overly hard, but I never saw it coming and it stung with that low dull ache that only a shot to the balls creates. 'Is that how we treat friends of mine Skip? Is that how I taught you to act in my home?'
The ball strike quickly took the breath from me and doubled me over, but I managed to somehow to keep from grabbing my balls. Breaking Jim's strictest rule against touching my cock and balls was out of the question. I straightened up, and tried again, grimacing through the ache. "I'm sorry Mr. Taylor, hello Mr. Taylor.'
'Much better,' Jim said. He turned to Bill. 'I'm sorry you had to see and hear that, believe me, he will be much more respectful from now on.'
By now the scene on the television had moved on to a two fisted hand job, the blonde's tiny hands travelling up and down an enormous oiled shaft as a long haired guy mumbled his approval, the relentless soundtrack blaring. Bill returned his focus to the screen, ignoring Jim and I.
Jim took over. 'Skip, this is how it's going to work. Bill here, well Mr. Taylor to you, is a buddy of mine visiting from out of town. We got talking last night while we watched some new porn, and he told me he was horny as hell and needed some, that he hasn't had any in weeks. I can't remember the last time I went a few days without...so I guess I understand. So I told him if he sucked me off during the movie and paid me $20 he could use you this morning. It was either that or let him tag Elise this afternoon, and that's not going to happen.'
I audibly groaned at the mention of Elise, Jim heard it and smiled. Elise is in her late twenties, average to bordering on homely looking, at least from the pictures I have seen. But she has an insanely hot body...5'7" or so, shoulder length coal black hair, womanly curves and a set of 36 DD's that could make a man weep. And she can fuck for hours, at least she can and will if you have an 8" long incredibly thick cock. And Jim loves to remind me about the last part; her bra doesn't come off for small to average cocks.
Jim turned to Bill. 'And nothing happens until I get the $20 loser.'
Jim returned to me. 'So you are going to go in to the guest bedroom with Mr. Taylor and do whatever he tells you to do for the next couple of hours. Or you can leave, and never come back.'
Bill handed a $20 bill over the back of the sofa without looking away from the television. Jim took it, and returned to me.
'So your choice. But fair warning, if you go in that bedroom Bill better come out of there saying you were fantastic, that he is completely satisfied, or you never come back here again. Do you understand me?'
I was horrified, and my mind raced, coming up with nothing.
'I want an answer now...Bill's dick is waiting' Jim demanded.
'Ok' I mumbled but quickly caught myself. 'Yes, Mr. Smith.'
Jim smiled an evil smile. 'See I told you he was a slave to my cock' he gloated to Bill. 'But then so are you slut'. Bill gave him the finger without looking up.
Jim continued. 'Ok, Bill, here are the ground rules. Skippy here wears a condom at all times; I don't want him drooling all over my place. Skippy is never, ever allowed to touch his cock. And he is absolutely not allowed to cum, do not let him tell you it was an accident or some bullshit like that. After that it's up to you, and he can pay me my $50 on the way out. After he leaves you can give me a report to see if he gets to come here again.'
I was astonished to hear that on top of getting sold to Jim's friend as a fuck toy I had to pay him the usual $50 fee, but kept my mouth shut. Jim took a long drink of his iced coffee.
'What will it be Skip?'
I knew, and both of them knew, that I couldn't walk out and lose access to Jim's cock. I suspected he didn't mean it, he would still want the cash and let me come back, but really couldn't take that chance.
'I'll do it' I mumbled. Jim seemed to pretend he didn't hear me, and Bill was still hypnotized by the big titted blonde. I spoke louder. 'I'll go in the guest room with Mr. Taylor.'
Jim refused to give me any kind of positive reinf***ement. He took that box of Trojan magnums out of the bag and tossed the bag at my feet. 'Put a condom on, then lick your pre-cum off the floor you pig.'
Even for Jim this was harsh talk, he is usually very pleasant, but he hates pre-cum. 'Yes Mr. Smith' was the only answer I could offer. I tore open my box of Lifestyle fitted condoms, and tore the foil of the first one, sliding it out of the packet. I knew Jim was watching closely as I fitted it on my cockhead, and rolled it down my shaft. I did it quickly and pulled my hands away quickly so he wouldn't accuse me of giving myself some pleasure, but even at that the sensation of the ring rolling down my cock almost made me cum. My sharp intake of breath gave me away, and Jim laughed softly as I fought to hold my load. Successfully fought to hold my load, but it was a struggle. I looked on the floor and did see several wet spots, I had to assume they were pre-cum. The thought of licking them up was repulsive, Jim's housekeeping standards were non-existent, I'm sure that floor hadn't been washed in years. However, when I looked up to see if Jim was just k**ding about the lick it up command, not only was he watching with obvious amusement, but Bill had stopped watching the television long enough to watch too, and obviously was enjoying this.
I leaned down to the floor, stifled a brief urge to retch, and licked up the first filthy wet spot. I pushed on quickly, thinking if I stopped I wouldn't be able to start again, and licked up three more spots. I thought I was done, but Jim's foot pointed toward one more spot, and I licked that spot too. It was horrible, but I was done, but I also realized that my submission had been well demonstrated for Bill before I went in the room, and it was made clear to him that I would do what I had to do to stay in Jim's good graces. Of course I also knew that Bill had experienced Jim's cock first hand, and knew well the effect it has on a man.
At this point, for the first time, Bill began to take over. He was still quite distracted by the blonde whose breasts were now bouncing cartoonishly as she rode the well hung guy hard, but was able to begin to take control.
'Skip, pick up the condoms bag and hold it in your teeth. Crawl on your hands and knees down the hall, go in the second door on the left. Wait in the middle of the room at the end of the bed in that position until I get there. Go.'
'Yes Mr. Taylor' was all I said, just as I knew that yes, Mr. Smith would be the only response if Jim had given me that direction. I grabbed the bag with my teeth and crawled down the hall, turned in to the unfamiliar guest bedroom with a single twin bed and little else besides piles of stuff, and waited on my hands and knees on the hardwood floor.
The wait was lengthy, about 20 minutes, and the oak floors were making my knees ache. The bag was very uncomfortable in my teeth and I couldn't stop some drooling on the plastic. My erection had fully subsided, and the condom weighted with pre-cum was just barely hanging on to my shrunken penis. I was keenly aware that the view to the hall was my ass with a black thong that had worked its way well in to the crack. In the distance I could hear the television sound track, and could hear Jim and Bill laughing, presumably at least some of the laughter was at my expense. I couldn't help questioning why I was doing this, then cursing Jim for being blessed with such an incredible cock and knowing I had to get through this. Over the years I have known Jim this thought has consistently haunted me. He isn't a particularly brilliant guy, very average looking, isn't in great shape, he works very little, just enough to pay his rent. But he won the genetic lottery and has this monster cock. His taste runs to very large breasted women, and an occasional completely submissive man. It isn't that he likes men per se, but that he enjoys humiliating other men with his cock. And he gets away with it, in fact has difficulty scheduling. And at less than 4" I am on my knees on the floor, as usual.
Finally, Bill made his way in to the bedroom. He wandered in, and stood for a moment taking in my situation. 'Move forward Skip' he said with a tone of easy authority. I scooted forward, and heard the door close behind me. Bill moved over and sat on the end of the bed facing me, and after a long silence finally spoke. 'Up on your knees facing me, hands behind your back, eyes down unless I tell you otherwise.'
I scrambled to my knees and assumed the position, bag of condoms still in my mouth. Bill made no move to take them, or do anything else. He just let me kneel and wonder.
'Lean over put the condoms on the bed' he said. I leaned and dropped them, feeling the ache in my jaw as I did.
He continued. 'So how long have you known Jim?'
'About 5 years' I replied, eyes still down.
'And how often do you see him over that time?' Bill asked.
'Once, sometimes twice per month.' Still looking at the floor.
Bill continued his interrogation. 'And how much do you pay him for a visit?'
'$50' I mumbled.
Bill was enjoying this. 'So you see him 15-20 times per year, let's call it 15, about right?'. I nodded, he continued. 'You pay him $50 per visit, have you paid him that right from the beginning?'
'Except for the first time, yes.' I answered more loudly now, resigned to telling him what he wanted to know.
'How did you start paying him?' Bill asked.
'It was his girlfriend Laura's idea. She told him that a guy with a cock as small as mine can't get a really well hung guy without paying for it. Well that and he is 10 years younger than me, so she set it up that way'.
Bill laughed. 'That sounds like Laura, manipulative bitch. But she has a talent for working guys over I will tell you. The panties were her idea too, weren't they?'
He was right, but I couldn't figure how he knew that. 'Yes, but how did you know Mr. Taylor.?
Bill laughed. 'She loves to make guys cross dress, you would be amazed how many guys have ended up in a bra and panties hoping to get a shot at those gigantic boobs. None of them have a shot unless they are hung like a donkey. More than one guy has had to buy pictures she took of them back from her. Bitch'
I suspected Bill had been one of her victims.
'So wait, let's figure this out. You see Jim at least 15 times a year, times $50 a visit, that's $750 a year. Times 5 years, that's at least four grand. I'm guessing Jim shoots two loads per meeting...about right? ' He didn't wait for my answer, he knew he was right. 'So you have paid four grand to get Jim off about 150 times. And how many times have you cum during all this?'
I was certain Bill knew the answer, but had no choice. 'Once. I accidentally came once during our first meeting.'
Bill was loving this. 'And you know there are plenty of guys like me who are blowing Jim for free, right?' I nodded, head down, he continued. 'So why are you paying four grand, FOUR GRAND, to suck another guys cock that other guys suck for free? Tell me!'
I was stunned by the math, four thousand dollars, probably more. More than 150 loads of Jim's cum, probably more like 200...but I had to answer. 'Because Jim is a lot younger than me and his cock is more than twice as big as mine. But mostly because he won't let me unless I pay him.'
'And why do the rest of us suck him for free?' Bill asked in the most condescending tone possible.
'Because the rest of you have bigger cocks than I do' I gave him the answer I knew he wanted.
'Eyes up.' Bill commanded. I looked up, Bill was sitting with a look of mission accomplished on his face. He had made his point, that even though he might not be in Jim's league, he was still a superior man to me. He stood up and slid down his sweatpants, stepped out of them and kicked them aside. He stood with his blue briefs inches from my face clearly tented by an erection. Clearly all this conversation had affected him, or maybe it was just a holdover from hours of porn. Embarrassingly enough, my own cock had stiffened again from all the conversation about sucking Jim, and it pointed straight out, condom clad. Bills tent in his briefs was not particularly impressive, I had to admit I was disappointed.
Bill sat down and leaned back supported by his arms. 'There is no getting around the size thing is there? Jim has that huge one, chicks flock to him, friends of those chicks do him behind their friends backs, his friends wives call him for some. His ex's all call him to get fucked, even if they can't stand him anymore. Laura was here two days ago, she didn't think it was funny that Jim didn't tell her I was here, but she still ended up in his bedroom for a couple of hours. It's ridiculous. Guys line up to suck him off, and not only doesn't he suck but he won't let the other guy jack off. Believe me, I was hating that rule here last night after a few hours of drinking beer and watching porn and sucking him off a couple of times.'
By now my erection was like steel, and Bill clearly noticed as it pointed nearly vertical.
'But then there are guys like you who have to pay to be Jim's bitch. How small is that thing again?'
'Almost 4", about 3 ¾"'. I was hoping the talk would end soon, Bill clearly had accomplished his goal.
'Wow, no wonder he makes you pay for it. You know you are the only guy who pays him don't you?'
There was something odd in the way Bill said I was the only guy that paid him, and before I even thought about it I blurted out 'Do any of the women pay him?'
Bill looked surprised. 'You don't know?'
He hesitated but my look made it clear I had no idea what the answer was. 'Yeah, a lot of them do. Most of the women who started out as friends of a friend pay him, usually because they have small boobs and he isn't in to that. So, like C cup or less pays for it. I think they pay about the same amount as you do. Of course they all get to cum, probably like a dozen times each once he gets going. He has one rich bitch who pays him a lot, like $200, she is a skinny old chick, 50 something with no boobs. That's why he doesn't work, he doesn't have to. And all the ex's pay for it, even Laura. That's why she started seeing you again, didn't you know that? ' I shook my head. 'Yeah, she was in grad school and had no money but Jim told her no pay no play. Jim suggested she get the money from you, so long as she didn't let you see or touch her boobs or get off. So basically you were paying Jim to fuck Laura, and he was making sure you couldn't get any from her.'
I was astonished. I had been paying Jim for years to be allowed to suck his cock, then had been paying Laura for a long time in hopes I would get her bra off but really only got badly cockteased, and all that money had gone to Jim too. I felt like such a fool.
'Ok Skip, enough talk.' Bill was ready for business. He stood up and slid off his still tented blue briefs, now showing a substantial wet spot. Eye level to me his stiff prick sprung free. It was well shaped and cut, but was rather small. It appeared to be about 5" to 5.5" and average thickness. Call me a hypocrite or afflicted with some sort of self loathing, but small cocks do nothing for me and this was no exception. Seeing it, even in my very aroused state, I could feel my erection wilting.
But Bill really didn't care, this wasn't about me. 'Start with the balls, get them good and wet, and I will tell you when you can start on the cock.'
Bill and I had been talking for almost 40 minutes, and he had left me in the bedroom waiting for about 20, so we didn't get started for almost an hour. But once we did start, Bill was determined to get his $20 worth. The next two hours was a bit of a blur, but bottom line is Bill shot four loads in two hours. He made me take two in my mouth before he decided it was time to fuck. But after a long session slamming in to me, which honestly got boring with his small cock, he decided to make me do ass to mouth. I begged him not to make me do it, but he made it clear that if I ever wanted to see Jim's cock again I was going to do it with enthusiasm. Eventually he returned to my ass to unload, then made me clean him again. His fourth and final load he stroked out on to my face, making me leave it there as I when he sent me out to dress and pay Jim.
Jim got more than his share of entertainment as well. He really enjoyed the remnants of the facial, but Bill also sent me out twice to get him cold drinks for him, forcing me to walk right past Jim as he sat at his computer surfing and emailing. I was too ashamed to even look at him, but heard him chuckling and commenting on how long we had been in there.
When I finally was allowed to dress and leave I was exhausted and filthy. My ass and balls ached, but for the first time in years I actually left without a throbbing erection. The length of the session and Bills tiny cock had me limp as I dressed to leave. Jim took my money, obviously pleased with what he had made me do, and suggested I email him later in the day to find out if I got a good report from Bill. Yet another hoop he could make me jump through, which is Jim's number one joy with guys.
He said if the report was bad I wouldn't get an email back, I knew right away that Bill would take his time replying so I could suffer a little. I was reaching for the door when Jim stopped me. 'Aren't you forgetting something?'
I was confused at first, the session had been so long and different from anything before, but fortunately I figured it out. 'Thank you Mr. Smith for allowing me to visit, and thank you for letting me service Mr. Taylor.' I don't know if I was as enthusiastic as usual, but Jim allowed me to get by with my attempt.
I drove home with my head swimming with the new information about Jim's 'business', all the women who pay for his cock. The small breasted (like C cup is small breasted!) friends of friends, the ex's, rich women paying big money. Laura with her DDD's having to pay, and making me give her the money for it.
And somehow, with Jim being this comfortable making people pay for it, being the only guy paying became even worse.
But mostly I thought about how I didn't get any of his big cock, and that I needed to see him soon.