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 head was swimming during the drive home from Jim's, now for the second time I remember very little of it. Jim's big cock, Laura's relentless and very effective humiliating control, Dee's trashy but very hot look. Laura's huge breasts and sensual smoking style. Jim's new distant, directive tone. The image of Laura putting the ruler on my cock, and my falling short of 4 inches. My pathetic, ridiculous really, failure. I re-erected very quickly in the car.
Once home I once again deteriorated in to hours of repeated masturbation which yielded powerful orgasms. All driven by the images of Jim, of Laura, of Dee floating through my relentless fantasy bank. Once again it led to a collapse in to a sound sl**p with a wasted raw cock, only to wake to a hard as steel drooling erection in the morning. I tried to resist the need to stroke off, hoping to organize my thoughts about the complicated experience from the day before, but was powerless to stop my hand from relieving it.
I made coffee, and sat staring at out a window at the forest behind my home. At first I couldn't help but focus on the image of Jim's thick hanging shaft and the enormous bulbous head of his cock. A sight I could only enjoy for a moment before he put it back in his briefs, clearly a gesture of punishment by depriving me. A larger image was becoming clearer to me though...yesterday I was completely naked, fully erect and drooling precum, and on my knees at his direction. He was mostly dressed, totally flaccid. In that moment his power was crystal clear, a power he exercised when he pushed me back and put away what he knew I wanted so badly.
I couldn't help but compare that image to what I saw as I was leaving. Jim in a pair of old jeans, with a t-shirt hanging over a bit of a belly. His at best average looks in his sloppy one room place. But I also saw the look of indifferent arrogance, that he knew I would be begging for a chance to return. And Laura's final words to me. In the midst of that mess, his home that would not compare well to many undergraduate dorm rooms with a bathroom across the hall, were two very average looking people. Two very average people who were blessed with an endowment that I desperately crave. And they know it.
As humiliating as it is, Laura was right, I am out of my league.
That day I opened an email addressed to Jim. I really had no idea what to say at this point, it had all ended so badly. Their last image of me was my scurrying around naked, cleaning up the mess my premature ejaculation had made and obeying their demand that I repeatedly go to the back door completely exposed. What recovery is there from that? Somehow saying 'Had a great time, let's do it again sometime soon' wasn't going to work.
Sorry about yesterday, I really am embarrassed, nothing like that has ever happened before. I hope you weren't late for your dinner. After the last two times I'm sure you aren't thinking you want to see me again, but I really hope we can try this one more time. Same as last time, total one way deal, will do it how ever you want and I promise I will do much better than last time. Please consider it, willing to work hard to make it work for you.
Clearly I was openly begging at this point, but I hit send. I really had no other options. I considered including an apology to Laura as well, but really couldn't figure out what I was apologizing to her for...this whole situation is a mass of confusion, but I only know I need to get back there.
To my surprise, I received a response from Jim within a couple of hours. Even stranger, I found two responses from Jim in my inbox, sent about 15 minutes apart. I opened the one he sent first.
Skip- At this point I can't really see much point in meeting again. I appreciate your willingness to do whatever I want, but I think you know there are plenty of guys out there who will give no reciprocation blowjobs to guys with big ones. I'm sure you understand. Jim.
His response didn't surprise me of course, I appreciated that he did respond rather than just delete my email. But I couldn't imagine what was in the second email, though I suspected it might be a copy of the first email that he accidentally double sent. I clicked the second email.
Skip- Laura asked that you email her. Her email is xxxxxxxxxxx. Jim.
I stared at the email for several minutes. I really had no idea what to make of it, but suspected Laura wanted to ridicule me further, what else could it be. Oddly, I felt my cock stiffening as I clicked her email address and opened a new window.
This is Skip, I was at Jim's place yesterday. Jim told me that you asked that I email you.
I hope you weren't late for your dinner yesterday.
My email felt really lame, but I had nothing to say or maybe I just imagined her reading it with the same look of disdain she has always given me. I hit send. To my shock a response came back within minutes. I took a deep breath and opened it.
skip I won't waste a lot of time here I will get to the point. I know how badly you would like to give Jim head. Based on what I have seen I'm pretty sure you haven't had a cock as big as his before and as you would know, SIZE MATTERS. HA-HA. I am offering you a simple deal. Just like before you strip, you get on your knees and you do as you are told and just like Jim said you don't touch your dick. If you cum this time you can't come back, and you will wear a rubber so you aren't dripping everywhere. When you get here you strip, then you give me $50 and two packs of marlboro lights hard pack. That's right, you are going to pay me so you can suck jim's cock. Don't waste my time asking questions we both know you will pay.
I re-read the email over and over. At first I was stunned, shocked...I couldn't tell if I was angry or insulted or...I really have no idea how I felt. But very quickly I got over it. Very quickly I understood the door was open again. I read the email again, then again. My situation started to fully sink in. I was going to pay for sex. But unlike the way just about everyone else does it (I guess), I was going to pay for the right to give another guy sex. How did this get so convoluted...I offered to give another guy a total one way blowjob, what guy doesn't say yes to that? But very clearly that is where we are...if I want to suck Jim's cock I will be paying for the privilege. And I suspect I will need to be grateful...
Thank you for your offer. I will admit I was a little stunned, I had no idea Jim played for pay. But it's all in good fun so why not. Of course I've never paid for sex before, but why not I guess. When is Jim available?
I guess I tried to save some shred of dignity by making this sound like it was all a fun game, and after I hit send I realized how dumb the whole thing read. I felt pathetic, but was also fully hard and knew I had to do this. Had to.
Minutes later I got a response from Laura, and if I had hoped to preserve some kind of dignity she had no intention of letting that happen.
skip jim doesn't play for pay as you put it and you aren't paying for sex because you aren't going to get any sex. You are going to pay to suck jim's big prick because you have to because you have a tiny one. You are going to buy me cigarettes because I can make you do it and you are going to leave here with your tiny dicklet hard out 50 bucks having swallowed jim's cum. And the whole time you are going to work your ass off hoping we let you come back. It must suck to have a 3 ½ inch dick. Thursday at 5 don't forget your rubber.
I could try to describe how I felt when I read Laura's email, but there really is no point.
Thank you, I will be there Thursday at 5 and will bring the fee, cigarettes and condom.
I wish I could say I felt degraded or humiliated, but any of those kinds of reactions were overwhelmed by the unexpected chance to return to Jim's place and get another chance with his cock. I guess my e-mail's brevity was an attempt to diffuse Laura's enthusiasm for slamming me, and I was admittedly surprised by her vitriol. While my attempts at being polite and professional while being f***ed to agree to pay to suck Jim's cock seem ludicrous in retrospect, at the time it made sense. Again my inbox dinged. It was from Laura.
skip put the rubber on before you arrive I don't want to deal with wrappers after you leave. Oh and since I know you were wondering yes Dee did know why you were here. That's pretty funny if you think about it that you were checking out her hot ass and great tits and she knew you were a little dicked cocksucker. Yeah I did tell her about your little dick.
The two days of waiting were torturous. The cycle of three times per day masturbation wasn't optional, but only reinf***ed to me the hold that the whole situation at Jim's place had on me. What was becoming clearer was it truly was the whole situation, not just the power of Jim's big cock. The elaborate requirements and fee reinf***ed that I was reaching beyond my station, Laura's abuse wasn't the rub, it was that she knew I had to take it. And yes she was right, Jim was the biggest I had ever seen live, let alone touched. What I am sure she suspected was that she also possessed that same kind of power if she ever chose to exercise it...her enormous breasts (I would later find out they were DDD's) were many sizes larger than the biggest I had ever seen or touched. All of my life experience had been with small breasted women despite an obsession with larger cup sizes. While I crave D cups, only once had I experienced a B cup, all of my other experience had been with A or AA cups. All of the hoops I now had to jump through, and knowing any visit included desperation to be invited to return, led to a total collapse of my dignity.
But now I stood at my bathroom sink knowing what I had to do. My car keys, five $10 bills and two packs of Marlboro Lights were sitting by the front door. On the bathroom vanity sat a single Lifestyle snugger fit condom, the foil torn open. I knew that another unintended orgasm at Jim's place would end my chances of visiting again. My only hope was that by jerking off just before I left I would have some hope of adequate control. My hand went to my limp cock, I closed my eyes and found myself thinking of Laura's vast cleavage as she leaned forward to place the ruler over my hard cock. I found myself imaging her taking a deep, cheek hollowing inhale of her cigarette before announcing my sub-4" erect length. And I heard my guttural moan as I splashed a small load on the back sink wall. I wheezed, and puzzled at the growing hold her sensual smoking had on me. I cleaned up and rolled on the small condom, and pulled up my jockeys. While it was still too early I couldn't wait any longer, and climbed in to my car...cigarettes and fee on the seat beside me.
I purposely took a longer scenic route to Jim's house, during the drive I felt my cock come back to life and extend to a semi erect state, loosely filling the condom. The feeling of the condom ring on my shaft wasn't helping my attempts to keep control. When I arrived a few minutes early I was fully hard again. I tried to slouch a little and hide my tent, and made my way to through the gate to the back yard.
To my horror I found Dee in the backyard watering some flowers, once again dressed in biker chic...boots, very snug and flattering jeans and super snug top accenting her bust. She held the garden hose in one hand and a cigarette in the other. She looked at me as I closed the gate and a knowing smile spread across her face. She brought her cigarette to her mouth and took a long drag, then gazed at my slacks as she let a long slow plume of smoke drift my direction. "Back so soon Skip?" Such a simple phrase, but her smirk and her tone said so much more... I stood dumbly, after all it was her house. "You better get going, you don't want to keep them waiting." She paused, then her gaze shifted. "Did you bring presents?"
To my horror I realized I had Laura's cigarettes and the money for the fee in my hand. I felt myself blush a deep red, and watched her gaze shift from my now obvious erection then back to my hand. I had no idea what to do, I think I mumbled something about needing to go inside and felt her stare as I hurried to the back door. Fortunately Jim must have seen me arrive because he called out from his room that I should come in as I arrived at the back door.
I opened the door and made my way past the now familiar washer and dryer and turned the corner toward the open door to Jim's room. I could see Laura in her chair as I neared the door, now very conscious of my erection. Laura was flipping through some womans magazine and barely glanced up as I entered. She started in on me right away. 'Heard you ran in to Dee. Bet she loved your little boner.'
Jim was once again sprawled on his bed idly watching a topless blonde with enormous breasts bouncing on a guy. Like Laura he didn't look my way. 'Hey Skip' was all he offered. Neither of them said anything, just leaving me standing there as she continued to read and Jim watched the blonde.
Finally I tried to get some kind of interaction going, I turned to Laura and held out my hand with the money and cigarettes. 'Should I give this to you?'
She didn't even look up. 'What were your instructions?', she asked with disinterested disdain.
I couldn't figure out what that meant until I thought I remembered the instructions said strip first, but didn't want to start undressing and get rebuked again. 'Should I get undressed first?'
Now Jim got involved. 'Skip, put your clothes on the chair before Laura throws you out,' he said sternly.
'If you aren't wearing a rubber don't bother stripping. Just leave the money and the smokes and go jerk off.' Laura added, still refusing to break eye contact with her magazine.
I undid my belt and unclasped my pants at the same time I kicked off my shoes. I stepped out of the pants and loosely folded them on the chair. I tried to remove my socks, nearly losing my balance and falling before tossing them on the pile. My polo shirt went over my head and on the pile, leaving only my jockeys. I had such an intense hard on that my waistband was pulled away from my abdomen, I wondered if my last minute jerking off session was going to help at all or if I was doomed to another premature ejaculation. I slid down my briefs and once again had to turn back to Jim and Laura fully erect. Neither looked up at my stiff condom covered cock.
I picked up the money and cigarettes and once again shuffled over and offered them to Laura. Finally Laura looked up, setting her magazine on the end table. Rather than take the fee, she first examined my hard latex covered cock which was pointing at her forehead. Both of us noticed that the condom tip was full of precum, a fact that clearly amused her. 'Hand me the money,' she instructed. I shifted the cigarettes to the other hand and gave her the bills. She unfolded them and very deliberately counted them, then equally deliberately refolded them. She crooked a finger and slowly slipped it in to her v-neck and under the edge of one bra cup. Pulling the white satin fabric away from her massive breast, she slid the bills in to the bra and out of view. Her finger slowly ran the length of the fabric down in to her cleavage. She knew exactly what she was doing. My condom covered cock lurched upward and I let out an involuntary moan. From the bed I heard Jim's chuckle, but Laura wasn't done. She now held out her hand and I proffered her cigarettes. She set them next to her magazine and picked up her ashtray and held it toward me without explanation. I took it from here and scurried to a trash can across the room and emptied it, then returned it to it's place on her side table.
Finally Jim took some initiative. 'Skip, get on your knees at the end of the bed,' he said as he gestured to same position as my previous visit. I moved to the end of the bed wordlessly and dropped to my knees on the hardwood floor. Jim stood and slid off the athletic shorts he was wearing, but to my surprise was not wearing underwear so his huge hose just flopped free right next to the side of my face. I gasped in surprise, well out of pure lust as well, but did not move. Jim was now wearing only a dark blue polo shirt as he sat on the end of the bed and slid over in front of me.
I heard a lighter click as Laura lit a cigarette, but didn't divert my attention from Jim's cock. 'Well he didn't blow his load yet, he's doing much better,' Laura mocked. She didn't stop. 'Do you remember your manners this time Skip?'
She was right, I had managed to control my arousal, though I was rock hard and aching to cum. My voice was thick with arousal, so I had to clear my throat, which brought a chuckle again from Jim. 'Jim, may I please touch your cock?'
Jim let my question hang out there for several seconds before answering. 'Not yet. Mouth only, no hands, just work on my thighs and balls. I want both of your hands on the bed so I know you aren't touching your dick.'
It felt very degrading, I don't know why after all I had already put up with, but I put my hands on the bed on each side of Jim. I dove in with incredible energy, licking and sucking his upper thighs, fueled by my throbbing erection and desperate need. Eventually Jim guided my head to his balls. 'Suckle each of them one at a time, go back and forth between them,' he directed. I worked one of his hairy plum sized testes in to my mouth and gently suckled, amazed at the mouth filling size, then switched to the next plum. I switched between them at least a half dozen times, not daring to move to his cock. Finally Jim took my head and guided it downward. 'Now work on the spot right behind the balls.' I did as instructed, working my tongue despite uncomfortable reach, and was grateful that it smelled of lingering soap. My tongue started to ache, my jaw was getting a little sore when Jim finally gripped my head again. I was excited to finally be getting a chance to move to his cock, but Jim again directed me to his balls. He reclined and seemed to be enjoying my work, but his cock was still completely limp.
Finally I got what I wanted to hear. 'ok Skip, still no hands, I don't want you cheating, keep them on the bed where I can see them. You can start on my cock now. I want a lot of attention to the ridge around the head, not just pumping up and down.'
I had to adjust my position, get up off my knees somewhat to get my mouth on his giant cockhead, and sliding it in to my mouth with a heavy but completely limp hose took several tries. I started to reach for it with one hand at one point but Laura snapped me back with a quick 'SKIP, uh-uh'. Finally I got it in and put my tongue to work on the ridge and slit, and heard a long pleasant moan from Jim. The size in my mouth was incredible, and I began alternating sliding down the shaft and working on his head with my tongue. I could feel the head and shaft thickening, growing in my mouth. I worked to a rhythm of pumping and tongue work that finally had Jim fully extended. I desperately wish I could have pulled back for a moment to see its fully erect size, but didn't dare. I detected the first viscous saltiness of precum, but Jim didn't appear to be moving toward any kind of advanced arousal.
'Ok Skip, still no hands but start working on getting further down the shaft and I better not feel any teeth! You need to get down to the base.'
I was beginning to tire, was sweat soaked and my knees were screaming for relief. I felt very frustrated by the no hands rule, it really required me to work much harder. I began trying to get further down his shaft, but found myself gagging on the monster cockhead less than half way down. I tried again and again, but couldn't even begin to get past the gagging. Finally I had to pull off after one particularly hard try. Laura was clearly enjoying my efforts and my growing exhaustion. 'I don't think he is going to be able to make you cum,' she offered as I coughed .
'Not at this rate he isn't,' Jim said flatly.
'Your cock is so big, can I please use my hands,' I pleaded.
Laura responded without hesitation. 'You can, but it will be your last visit. We allowed you to pay for a blowjob, not a handjob. If you aren't up to it you can finish with a handjob, but that's only because once a man's dick gets hard it needs to be relieved, he shouldn't have to endure the discomfort of an erection without release.'
Her meaning was clear, as clear as my own straining cock. I went back to work, sliding my mouth back on to Jim's pole.
I worked hard for another twenty minutes, the last 10 minutes trying to get past the pain in my jaw, my back and my knees. Finally Jim appeared to focus, and began moving toward a more aroused state. 'Faster' he demanded and I bobbed up and down as fast as I could. The first cum blast surprised me as Jim had not made any kind of sound, but its volume was mouth filling and slammed in to the back of my throat. I involuntarily started to lurch backwards, but Jim held me in place as the second blast unloaded, then a third of nearly equal size. I was gulping and gagging and swallowing, drooling a great deal of it down his still half dry shaft. Finally the sixth or seventh spasm was the last, and he eased his grip. I reeled backwards as Laura laughed, cum drooling down my chin on to my chest. Jim sighed contentedly, but then sent me to the same towel pile to clean him up. I stumbled awkwardly to my knees, they cried out from the pain of kneeling so long on the hard floor.
I took a towel and went to wipe my chin but was again rebuked by Laura. 'Those aren't for you!' I stood foolishly with the towel halfway to my chin dripping cum, but resignedly dropped to my aching knees once again.
I hefted Jim's now flaccid shaft and gently began cleaning around and over it. Finally having it in my hand caused my rigid dick to jump several times, adding to the now very full bulb of precum. When he was cleaned up I just stood, not daring to use even the soiled towel for myself, but not knowing what to do.
Laura set me straight. 'You know where the towels go when you are done,' as she gestured to the door. I realized she was sending me back down the hall wearing only a condom, but was resigned to doing as I was told. I opened the door and made my way down the hall, but even from a distance could clearly see Dee near the door continuing her watering. Before I could even think about turning back, Dee turned and looked directly at me. At me in my fully aroused glory. She made no attempt to look away, but just stared as I stood frozen. Finally I saw no option but to take another step forward and flip the towel on the washer, then wheel and scurry back.
When I came back through the door I found everyone returned to their original positions, Laura once again engrossed in her magazine, Jim once again wearing his shorts and watching television...now some baseball highlights. They both ignored me, and neither objected when I reached for my underwear. I still had Jim's cum on my chest, but had managed to clean my chin adequately. I dressed quickly and silently, though awkwardly around my stiff cock. When I was dressed I turned to them and stood, finally squeaking out a thank you and walked out completely ignored. Mercifully Dee had finished her watering, and was nowhere to be found. I got out the gate to my car with no further incident. I started the car and drove about 1 block down Jim's street before I pulled over in front of a white cape style house. As soon as I rolled to a stop I reached down and furiously rubbed through my pants, quickly unleashing a massive load in to my condom. The cum load overwhelmed the condom and spilled out in to my briefs as I gasped for a breath, a dizzy sense of some relief as a stain spread across my lap and my cock finally deflated.
I successfully serviced Jim's cock, though the path was now clearly a brutal road of deepening humiliation that Laura clearly enjoyed, and Jim was increasingly an enthusiastic participant.. It took time, suffering and significant money. I was now on the side of the road with cum drying on my chin and chest, my body aching. I could feel my shrunken cock slipping out of the condom, spilling it in to my soaked jockeys and pants.
And I knew I would soon be begging for the chance to pay to be allowed to do this again.