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»
The drive home was a blur, I don't remember any of it but mercifully it was only 15 minutes or so. I say mercifully because my throbbing hard on was unrelenting. The image of Jim's enormous cock, it's overwhelming girth in my mouth had me achingly erect the entire drive. When I finally pulled in to my garage I was in bad shape, and longed for some relief. I would have run to the bathroom if my tented slacks allowed it, so I hobbled as rapidly as I could. I stood at the bathroom sink fumbling with my belt, finally working the clasp successfully and letting the pants drop to the floor. My briefs were soaked with precum to the point of translucence, the angry cock head clearly visible. I thrust my hand under the waist band and gripped my hard cock with my thumb and forefinger and stroked furiously. By the third stroke I knew relief was near, my head was already thrown back, mouth open as I gasped for breath. The fifth stroke unleashed the first powerful blast of cum in to my Jockeys, soaking my hand in the process. Surge after surge of cum followed as I let out a long, primitive moan. As the last waves of orgasm rolled over me I had to grab the sink to keep from falling, finally dropping to my knees wheezing and dizzy. My hand was still firmly buried in my underwear and a long string of cum drooled toward the floor. It was as powerful an orgasm as I could remember.
In the next hour it was followed by two more rounds of needed masturbation, neither approaching the intensity of the first, but very impressive in the powerful orgasm each yielded. I was consumed with the image of Jim's huge member. I was drained and my balls ached from repeatedly being pushed to their limits of propulsion. I sat on my bathroom floor, hand on my tiny, wasted cock, dazed and helpless to the memories of the afternoon.
Finally I was able to regain some control, and took a long hot shower to attempt to clear my head and clean off an afternoons crust of the remnants of repeated loads of precum and cum. While the shower helped a great deal, bringing me back to feeling nearly normal again, the soaping motion created yet another erection, and I soon found myself leaning against the tile as I unleashed the fifth load of the afternoon and evening with a wailing grunt. I collapsed in to my bed after drying off, my cock chafed and raw and my balls throbbing. I was asl**p almost immediately.
The nights sl**p was very sound, my body and my mind wasted by the previous afternoon. But the rest brought some recovery to my exhausted privates, and they woke me in the morning with a boner that cried out for immediate attention that couldn't wait for a bathroom trip. I gingerly gripped my still raw cock with my familiar two finger grip, in very short order sent a new load of cum skyward to splash down on my chest and neck. The volume was moderate, but the distance of the shoot exceeded anything since my teenage years, splashing on my throat.
I knew I needed to see Jim again, desperately needed to see him. I was haunted by his big cock and so badly wanted another chance to service it. But I was also confused by the arousing memory of Laura, sitting to the side pulling all the strings as she kept nudging the action for her amusement. She clearly enjoyed needling and humiliating me, enjoyed the power my obvious desperation for Jim's cock gave her, obviously delighted in using my small cock and premature ejaculation to make it clear she considered me to be much less of a man. And I took it. I had to.
But most searing was the look of delight in her eyes as I left, plainly asking them for a chance to visit again, a request which fell completely flat, no response. My desperation only emphasized by my obvious erection which Laura had not permitted me to relieve.
I had to try. I couldn't ask right away, that would be too pathetic, but it took all of my self control to wait two days before I found myself staring at a blank email addressed to Jim's inbox.
'Jim- Thanks for a great time Tuesday afternoon, I really enjoyed meeting you and Laura. Hope you enjoyed it too. I would love to get together again sometime soon, let me know when you might have some time.
I re-read my message over and over, inserted and deleted a line or two about his big cock, finally just hit send.
And then I waited. And waited some more. A few hours became a day, then two, then three. Finally on day four I found Jim's name in my inbox.
'Hey skip. Enjoyed meeting you too, you seem like a nice guy. Talked about it with Laura and not sure if we are a good match to meet again. I think for next time I am looking for a guy a little more like me and would like to be able to play with him a little too, looking for a guy who can handle that part a little better. Who knows, maybe we will hook up again some time down the road. J.'
I was crestfallen and disappointed, but I couldn't give up. I had been jacking off at least twice a day to the memory of the afternoon with Jim, and have to admit that increasingly I had found myself fantasizing about Laura. About Laura and her enormous breasts, directing my humiliation from behind a smoky haze of bitchy confidence. For gods sake, she was maybe 23 and I am nearly twice her age. What she would give for my BMW...but she also holds the cards in this deal, she knows I have to kiss her ass.
I had to get back in the door, had to convince Jim to let me visit again. Somehow, some way.
'Jim- Thanks for the reply. Hey, I understand what you are saying, and I wasn't at my best that day. Would love to get another shot to show you that wasn't really me. Would be more than happy to do a no reciprocation deal if you like, what guy doesn't like just lying back and getting a blowjob? Give me another chance, trust me, you won't regret it! Can arrange my schedule for what works for you...let me know...
The arrange my schedule part sounded so desperate when I re-read it, but I had already hit send, and I was desperate, so whatever. Once again I was destined to endure the torment of waiting, not knowing if I would get any response at all. The wait this time was even worse, days went by with no response, I considered resending just in case my email was lost out there. Finally after a full eight days Jim's name appeared in my inbox.
Skip-I guess we could think about doing this again, it would have to be a totally different kind of thing from last time a real quick strip kneel and suck. If we have to talk about condoms forget it. After I get off you can dress and leave, I'm not going to touch yours and I don't want to have to watch you jerk off. If your in to that confirm you can be here at 5:00, you should be done and gone in 20 minutes or so.
I couldn't understand why he was so adamant that I couldn't get off but knew I would agree to almost anything at that point. My email went right back saying 5:00 is fine.
I spent the afternoon with a nagging partial to full erection, so hot for my second chance with Jim's big cock. At 4:00 I started getting ready to leave, by 4:15 I was pacing and watching the clock, troubled by my unrelenting boner. I drove to Jim's place fully hard, leaking copious pre-cum. I parked in front of his house, and made my way through the side gate to the back door. I found the back door open, with only the screen door blocking the hallway to Jim's room. I could hear voices down the hall as I rapped on the screen door. I heard 'C'mon in Skip' from down the hall, so I let myself in.
The back door enters a hallway, it turns a corner to Jim's room. Jim's room opened on to the hallway, the bathroom was across the hall. As I turned the corner in the hall I found the door to his room open but the entrance was blocked by a woman leaning against the doorframe chatting with Jim, and apparently chatting with Laura as well from her laugh and the trace of cigarette smoke in the air. Tall and very thin, kind of a trashy biker look to her, with a rough mid -- 30's look to her. She looked over her shoulder and gave me a puzzled once over, a clear 'What's wrong with this picture look'. Was she wondering what a preppy 40 something guy was doing visiting Jim and Laura? Did she know why I was there, and I didn't fit what she expected? Was I paranoid or did her gaze linger at the almost certainly visible tent in my slacks? Whatever it was, she made no move to step aside and let me pass, but returned her attention to Jim and Laura and continued her interrupted story, leaving me to stand awkwardly and impatiently in the hall. After nearly a full day of semi-erect anticipation I was very anxious to get in the room, but had to admit that her denim covered sculpted ass had my attention. That fact not lost on her.
'Jim, this must be your friend Skip. From the looks of things my ass has him more than ready for you.'
I was snapped out of my daze to find I had clearly been caught with radar lock on her backside, and her own fixed stare on my crotch made it clear she had noticed my condition. In fact, apparently she was taking credit for my obvious arousal. But more startling was her comment, did she know why I was there? Did she have every detail of my last visit, or know the terms that had been dictated to me to earn a return visit?
'I have to run, let's finish this later in the week' the mystery woman said to Jim or Laura. She turned toward me, her straining t-shirt showing an impressive bust, likely a C cup. She still made no move to allow me to pass, instead give a rather purposeful, lingering stare at my crotch. 'Have fun' she said with a smirk and strode by me down the hall.
Finally I had unfettered access to Jim's room, but could only shuffle nervously to the door. I found Jim sprawled comfortably on his bed, Laura in her customary chair, both facing the television with some kind of afternoon television program on. 'Well, you met Dee, my landlady,' said Jim with a smile. 'Real piece of work she is, huh.'
'Looks like she was right about what her ass did to Skippy' chuckled Laura with a gesture toward my trouser tent. 'Or did you come through the door with the little guy hard?'
'C'mon Laura, be nice to Skip this time.' Jim said, though his amused grin made clear he found my state to be as funny as the women had. 'I don't mean to rush you Skip, but we have to be somewhere so why don't you get started putting your clothes on the chair in the corner.'
I guess I hadn't really thought it through, but only now did it dawn on me I was going to be naked, and apparently fully erect, for this process. That detail really hadn't registered in a scene where Jim made it clear I wasn't getting off, but now the reality of it was upon me, and my embaressment was almost paralyzing. I froze, my mind scrambling for an out, a way to maintain some dignity in this process. But I also found my gaze drifting to the pronounced bulge in Jim's jeans, and that bulge was clearly winning the battle. I started to reach for my belt.
'C'mon Skip, if you don't get going we're going to be out of time here...and I'm sure you don't want that to happen.' Jim's tone had an edge to it, it was different from the nice guy tone I knew. The tone was effective though, I raced to get my shirt unbuttoned as I kicked off my shoes and socks. The shirt dropped to the chair, but now there was no delaying the inevitable. As I unclasped my slacks I knew my cock was as hard as it had been all day, but I had no options as this stage. I turned to the chair as I slid down the pants and underwear, stacking them neatly on the chair. I was now out of time and couldn't will myself limp, so I slowly turned to face Jim and Laura.
Laura let out a rather loud guffaw. 'It's even smaller than I remember it,' she gushed. She crooked a finger at me. 'Come here' she demanded, pointing to a spot immediately in front of her. I glanced at Jim, but he offered no assistance, so I shuffled over. In her low upholstered chair Laura was roughly level to my hard on, but from my raised vantage point I was looking down at a canyon of cleavage. My erection jerked and leaked. Laura glanced down at her v-necked window. 'Not a chance' was all she said with an amused sneer. Laura slid her hand in to the side slot of the chairs cushions and produced a 6 inch ruler. 'Push it down so it's level to the floor Skip' Laura directed.
My humiliation was almost unbearable. I felt so naked, so embaressed by my erect state. But all three of us knew I would do it, and I did. With my index finger I pushed my shaft down to pointing straight forward, the touch and movement causing an involuntary sharp hiss from the pleasure.
'Geez, don't cum on me!' Laura blurted out.
Finally speaking for he first time since I arrived I gasped out,'I won't, I won't, just don't touch it!' I blushed crimson as I realized I had admitted to all three of us I was dangerously close to orgasm, and we hadn't even done anything.
'Trust me, there is no risk I will be tempted to touch that thing.' Laura choked out as she laughed loudly. She continued to chuckle but finally brought the ruler forward and rested the end against my groin area above my throbbing shaft. She leaned forward and squinted, and a broad smile spread across her face. 'Almost 4 inches.' she announced in an odd tone of triumph.
Jim finally took some control of the situation. 'Ok, ok Laura, you had your fun...leave poor Skip alone. We really need to get going. Skip, get on your knees at the end of the bed here.' His use of the phrase 'get on your knees' again had that new tone, and the choice of words made it clear this was an act of submission. But it was a step closer to getting some of his monster cock, so I dropped to the hardwood floor. 'I'm going across the hall for a minute, why don't you wait here.' Jim climbed off the bed and sauntered out the door.
Laura clicked her lighter and inhaled deeply on a Marlboro Light. Her long purposeful exhale, followed by a second cheek hollowing inhale did little to ease the awkwardness. Finally she leaned forward and talked through her second exhale, her intentional posture drawing my eyes to down the front of her loose hanging shrit. 'Almost 4 inches,' was all she said.
Jim ambled back to the room, stopping in front of Laura as he slowly undid his belt. They chatted about their imminent dinner plans. His jeans slid down, and he stepped out of them revealing a pair of blue briefs. Laura got a look of mischief, and reached out to caress his hose through his briefs. 'We could send Skippy home and I could take care of this?' she offered. 'You know I can do things he can't do.'
I couldn't help myself, it came out in a tone that was far too desperate. 'No, No, Please' I begged. Laura's explosion of laughter made it clear that my pathetic begging was her goal all along.
Even Jim chuckled as he slid over on the end of the bed in front of me. 'Stop tormenting Skip, he has suffered enough and we really need to get this over with.'
Now I was eye level to the front of Jim's briefs, and for the first time the clear outline of his cock in severely tested blue cotton was about a foot away. I reached for his waistband, or maybe to touch the outline of his cock, I really don't remember which. My own cock was now essentially vertical and painfully hard. But my reach was interrupted. 'Now Skip, show some manners. When you met Dee a few minutes ago did you just grab her ass? We all know you wanted to, but did you d o it?' I was confused, and wanted so desperately to get ahold of his cock. Jim continued. 'Oh wait, Skip, one more thing. I don't want you touching your cock while you are in my place. If we catch you touching or stroking I will shut this down in a minute. Do you understand? I don't mean to be evil, but you shoot so fast we just can't take the risk, so that's the way it has to be.' I didn't know what else to do and my knees were starting to ache, but my ragged breathing made it quite obvious what kind of condition I was in. I just nodded dumbly.
But still I was stuck in the manners dilemma, and really didn't know what I was supposed to do. I finally lowered my head and asked. 'Can I please touch your cock Jim'.
'Much better, see, you do have manners.' Jim's insincere praise was degrading, but I was long past caring. 'Now, lower my briefs, but no touching. Any accidental contact and we call it a day.'
At this point I was completely off balance. What I thought this session would be was a total one way blowjob. He uses me as his whore, I get access to a huge cock. I couldn't figure out what this was turning in to, but knew I had to keep pushing forward . I reached for his waistband, pulling it out with all the delicacy and caution of an electrician handling high voltage wire. Pulled well away from his body, I slowly lowered the waistband, gradually exposing the root of his shaft and progressing cautious inch by inch down his toward the head. Jim waited to the last second to finally lift his butt and allow me to slip the briefs down his thigh, completely uncomvering his thick, heavy hose and plum sized head.
'Oh my god' I rasped out in wanton admiration.
Unfortunately, the reveal of his cock was more than I could handle. To my horror I felt a surge of arousal that blew right past my ability to control it, and completely untouched I shot a blast of cum straight up in the air, landing on the bed next to Jim. The first spasm was quickly followed by a second healthy shot, then a third. At first I reached for my erupting cock in some kind of ridiculous attempt to stop my orgasm, but quickly remembered I wasn't allowed to touch myself there and managed to stop my hands an inch from contact. I stared helplessly as my cum blasted forth.
For what seemed like eternity there was only silence, and I could only look down at my cock as it softened slightly and drooled some more cum. The silence was broken by the click of Laura's lighter, out of the corner of my eye I could see her send a long plume of smoke toward the ceiling. 'Skip, you are out of your league here.' Laura said with no emotion, just a plain statement of fact. She took a long second drag and left me to suffer in the silence. Finally Jim shifted, bringing my attention back to him. He reached forward with his right hand and gently pushed me back by my forehead, back so I was sitting on my heels. My now nearly limp cock just hung, still dribbling cum. It looked smaller than I have ever seen it.
Jim stood, his cock hanging and swaying in front of my face. He reached down and pulled up his blue briefs, taking time to tuck his shaft to the left. Again the outline of the straining briefs was powerful. I groaned as it was now obvious I wasn't going to get what I had come there for. Jim finally spoke. 'Skip, get a towel from the pile in the corner and clean up the mess you made. Then take the towel and sheet from the bed and put them on the washing machine in the hall.' I started to get up and reach for my underwear, but Jim clarified. 'I said clean up this mess, you can get dressed after you are done.'
My panicked glance toward the door and hallway made it obvious what I was thinking. Laura saw her opportunity. 'Yes Skip, he does mean go down the hallway naked. And yes, there is a chance Dee will be out there, it is her washer and dryer. Don't worry, she has seen her share of dicks, more than her share actually. Probably never one that small...'
Jim interrupted. 'C'mon Skip, we need to get going. Get this mess cleaned up now.'
I scrambled to my feet, my aching knees slowing me. There were three or four towels, cheap ugly greyed towels, in the corner. I took one off the top of the pile and returned to the bed. There were five or six major wet spots on the top and down the side of the sheet. Jim was now busying himself getting clothes to wear out that evening, but Laura was clearly watching everything I did. Again I was struck by my situation. I am a quite successful forty something executive. Completely naked I am being supervised by this early twenties girl, being supervised with utter disdain. And we both know I have to take it.
I wiped down all the wet spots with the towel, then pulled up the corners of the sheet and removed it from the bed. It reavealed an aging, cheap mattress. Balling up the sheet with the towel, I now faced the door. Laura arched one eyebrow, and with a subtle head nod directed me out the door. In a pathetic attempt at modesty I covered myself with the sheet and opened the door. The hallway was silent, it seemed the coast was clear. I walked down the hall and around the corner, seeing the appliances I had not noticed on my way in, right next to the open door to the backyard. I crept up as close as I could to see outside, the backyard was empty. I tossed the laundry on the washer and scampered back to Jim's room.
As I slipped back in to Jim's room I saw the evil look on Laura's face I had now come to recognize. Jim was now oblivious to me as he continued to search his closet, back to me. I headed for my clothes, but Laura's voice stopped me. 'Skip, you missed all the cum you leaked on the floor.' I glanced over, and sure enough there was a small puddle on the floor beneath where I had been kneeling. Knowing what I had to do, I reached for another towel to clean it up. Again, Laura spoke...'Uh, uh. We aren't here to do endless laundry for you. Go get the towel you used.' Her tone was very stern, but it was my mess and there was nothing I could say. I opened the door again and turned down the hall.
I made my way down the hall, glanced out the backdoor, again finding the coast was clear. I pulled the soiled sheet apart searching for my towel, after an eternity of naked vulnerability I found it and raced back to the room. Laura chuckled at my naked sprint in to the room. I bent over and wiped down the puddled floor, making a couple extra swipes for good measure. When I finished I reached for my underwear.
'What are you doing?' Laura barked. 'Can't you follow simple directions! Take the towel down to the wash, then you can get dressed...and wipe the drool off the end of your dicklet too! And hurry, we are so late!'
I looked down and saw what Laura was referring to, still stinging from her demeaning tone and the dicklet comment. A long string of cum was hanging from my cock, I wiped it with the towel, beyond being self conscious. I all but sprinted out the door, rounded the corner of the hall and tossed the towel on the washer from the corner. I wheeled and made it back in to the room undetected.
By now Jim was dressed for dinner, and was slipping on his shoes. I was struck by how ordinary looking he was, kind of out of shape with a poorly grown, thin mustache. It all seemed so unfair that because he won the genetic lottery and was so blessed with that marvelous cock he could get what he wanted. But finally I was allowed to reach for my clothes with no rebuke from Laura. My briefs and pants slipped on quickly, I felt slow and clumsy buttoning my shirt. Still Laura just watched, now even Jim looked on with impatience. I slipped on my shoes, and now stood awkwardly fully dressed. Not knowing what else to do, I extended my hand to Jim and thanked him for allowing me to visit. A disinterested 'Take care' was his reply as he loosely shook my hand.
Laura spoke up. 'Time for you to go Skip. Sorry you didn't get what you came here for, but I think you probably learned something today.' Her meaning was obvious, as obvious as her meaning as she gestured toward the door. I stepped out and down the very familiar hallway, past my laundry pile and out the door. It was only then, as I walked around the house toward my car that I fully realized Laura's meaning, that in all of the happenings of the last 45 minutes or so I never did get any part of what I came there for. Jim had shown me his huge tool, but my pathetic ejaculation had eliminated my chances of even touching it.
I got in my car and drove off, knowing I desperately craved another chance with Jim's big cock, much more than I had before our meeting today. Also knowing my chances were practically zero, maybe less than that.
Laura's words rung in my ears. I was out of my league. But I had to try.