Date: Wed, 30 Nov 2011 00:07:51 +0000 From: william michael Subject: Prep School Memories The usual caveats apply. Comments welcome. Please include title in subject line of email. Charlie Weston sat on the bed in his new dorm room at one of the most prestigious universities in the country. His parents had just left and his roommate had yet to arrive. He looked around the room and thought about the adventure that was ahead of him. Then he thought about the four years of high school that had just recently concluded. And what an adventure that had been. After eight years of parochial school his devoutly Catholic parents had sent him to a boarding school to further his education. Charlie had always been pretty non committal about the whole business of religion but he went through the motions because it would have been too much of a hassle to fight it. So he had arrived at the prep school campus with its elegant field stone structures, dominated by the large church wondering what being so far from home would bring. Knowing more about Charlie would help the reader understand better what would follow. Still fourteen, he was not particularly tall, with a wiry slender build. He was handsome in a boyish way with an easy smile and a somewhat laid back attitude. His exposure to girls had been minimal as the parochial school was boys only. And since the students arrived by bus everyday and were watched over by some rather heavy handed brothers, his exposure to boys was pretty circumscribed as well. His only sexual pleasure was the occasional masturbation session, carefully orchestrated for when his parents would leave him home alone for an evening and he would stroke himself to orgasm in the shower, sending all the evidence down the drain. He didn't consider it a guilty pleasure since he didn't get the whole guilt business anyway. Unlike his new college dorm room, when he arrived at his prep school room it was partially occupied by a smallish boy, quite shy, with a head full of unruly red hair. His name was Max, short for Maximilian and that was about all he could get out of him. Over the following few weeks he found that the high school was quite as strict as he had been used to but there were still plenty of rules, curfews, and a faculty proctor in each residence hall to keep things under control. The one for his hall was an older single man who taught history. Some the others were married with families. As Charlie the college freshman thought back he had to smile when he thought about the first step on the long exciting journey he had taken. Normally he was a very sound sleeper, but he was thinking about some questions that raised in his earth science class and sleep was long in coming. As he thought he became aware of a soft persistent rustling sound coming from Max's side of the room. As he focused his attention he also began picking up the sound of soft but staccato breathing. "Max? Are you okay?" he asked quietly. The only response was a short sharp gasp and the cessation of any sound. He didn't press but remained quiet and let his own breathing slow. After about fifteen minutes, he again heard the soft rhythmic rustling noise and after a while the ragged breathing resumed. Slowly Charlie reached for his reading lamp and flipped the switch on. Looking over in the muted light, he could clearly seeing the bed cover tented over the smaller boy's waist, his face turned toward the light, his eyes wide in panic. Charlie regarded his roommate with raised eyebrows and Max hissed quietly, "It's not what you think, I was just scratching my leg." Charlie gave him that easy smile and said, "You might have been scratching an itch but I doubt it was your leg." "Please, man, don't say anything. It's been weeks since the last time and I'm going nuts. I thought you were asleep," Max pleaded. "Relax, dude. I"m not going to turn you in. I don't think there's anything wrong with it. Be my guest," Charlie said. "What? With you awake?" "You need privacy?" Charlie asked. "Well, not always. I've done it with someone watching before but I knew him a long time," Max replied. Charlie nodded, having heard about some of the guys back home doing it in pairs or groups but he was always solo. "Was he doing it, too?" Charlie asked. "Yeah, we sat at opposite ends of his bed and watched each other. I was sleeping over." Charlie thought about this for a couple of moments. The idea was intriguing to him and he could feel a little swelling of his own begin. With a nod he threw off his blanket and got up and walked over to Max's bed. As he always did, he wore a t-shirt and boxers to sleep in. A bulge was starting to form. Max's eyes stayed wide as Charlie sat down at the foot of the bed facing the smaller boy. "I've never done it with someone else watching. It sounds interesting so I thought I'd try it, okay?" "Well, sure, okay," Max replied, barely above a whisper. With a smile Charlie reached down and fished his semi rigid cock out through the fly of his boxers. Max's eyes got wide again. While Charlie may have been an average sized fourteen year old, his cock wasn't. It was thick and while only partially hard, it was showing significant length. He began to stroke it slowly, letting it grow in his hand. Max slid out from under his covers, pushing himself back until he was sitting up against the headboard of his bed. His pajama bottoms had already been pushed down past his knees, his cock and hairless balls fully exposed. Because of previous attention, not to mention the sight of Charlie's cock, Max was fully hard, somewhere around four and a half inches. He settled himself and then he began to stroke himself. It wasn't long before Charlie was completely hard himself and it looked like he was a full seven inches long and probably five around, a very healthy size for his age. His shorts must have been too confining at this point because after a look at Max, he shrugged a bit and then slid his shorts off. With his cock fully exposed, Max could only say, "Wow." Charlie smiled and gave his cock a little shake in Max's direction. Then he shifted around and opened his legs a git more and this exposed his next surprise, two large egg shaped balls in a loose hairless sack that was resting on the bed covers. "Holy crap," Max hissed, "you're fricken huge." "Am I?" Charlie asked. "Of course, haven't you seen other cocks?" Max whispered. "Not really. We didn't have showers and such at school. We had some sport stuff at the end of the day and just went home after. Yours is the first I've seen this close up." "Well, I'm sort of average for our age but you're way past. You must cum a lot with those big balls." Charlie just shrugged but he was pleased with the idea that he was somewhat out of the ordinary this way. The two boys settled into a nice steady rhythm and Max couldn't take his eyes off of Charlie's fat cock. As Charlie really started to get into it, his cock began to ooze precum and he began to rub it into the head and upper shaft. He looked over and noticed that Max's cock was oozing as well but not nearly as much. Charlie was really enjoying this and he vowed that he would do it more, and more frequently. The two roommates continued stroking themselves, making use of their precum to lubricate the taut skin of their dicks. After seeing Max do it, Charlie began caressing his heavy balls with his free hand. He liked the way that felt, too. It didn't take much longer for things to reach their peak. Max was the first to whisper through clenched teeth that he was going to cum. Charlie's eyes fixed on the head of his roommates cock, which had swelled and gotten much darker. With a low grunt Max shot his load. The first two went several inches high and then dropped back onto his hand while the rest dribbled down over the head and his fingers. Charlie liked what he saw and it pushed him over the edge and he shot his load as well. His cum shots were a bit more spectacular. He let loose with half a dozen strong streams, each one rising as much as two feet before splashing back onto his t-shirt with a few more weaker shots dropping on to the clenched fists wrapped around his thick shaft. He let out a sigh when the last bit oozed from his cumslit. "Geez, Charlie, that was awesome," Max enthused. "I've never seen someone cum like that. You're a mess." "I didn't think it would be like this," Charlie said, "I always did it in the shower and it just ran down the drain. It's a good thing I had planned to do laundry tomorrow anyway." Max picked up a box of tissues and took a couple to clean himself off and then handed the box to Charlie who only took a few to clean his hands and then he peeled off his t-shirt, rolled it in a ball and threw it in the hamper across the room. Now unashamedly naked, he shifted over so he was sitting on the bed sideways with his back against the wall. He looked at Max who still had his pajama top on and asked, "So how long have you been doing this?" "Jerking off? Since I was twelve, if you mean with someone else, just this summer," Max replied. "The first time I came I was eleven or so. In my sleep. I haven't been doing it a lot but I intend to do a lot more in the future. This was great, thanks." Max smiled shyly as the 'buzz' began to fade. "I am kinda surprised, though," Charlie continued, "you know, you being so shy and all." Max nodded. "I know," he whispered. "I always did it alone when no one was home, but this summer, well, I know this guy really well so..." he tailed off. "That's cool. Well, this will be our little secret, although I gotta think we aren't the only ones doing it." Charlie laughed to himself thinking back on that comment and thinking how right he was. His thoughts shifted to how that freshman year progressed. He and Max hardly missed a night where they didn't strip down to bare skin, find a comfortable spot where they could sit near each other and use each other for visual stimulation and stroke themselves until they came. Despite the new frequency for Charlie, his loads were still large and explosive. The boys had quietly scrounged a large supply of napkins and paper towels from various sources around the school and dumped the used ones separately in different bins. Charlie particularly enjoyed the memory of how the situation took a turn just after Thanksgiving. It was Saturday night and the boys were once again, naked, the lights down low. A spare blanket was spread on the floor and the boys sat facing each other. Max had become much more at each around Charlie, his easy going manner and the fact that they spent so much time naked together helped overcome the smaller boy's natural reserve. As they sat on the floor with semi rigid cocks, Max decided to ask the question that had come to mind the first time he saw that big beautiful dick. "Can I touch it?" he whispered. "What? My cock?" "Yes, I've wanted to for a while now," Max admitted. "Yeah, okay, sure." Max's eyes lit up and he scooted closer to his roommate, their legs close but not touching. Tentatively, Max reached out and with a slightly shaking hand, wrapped his fingers around the thick shaft and gave a squeeze. "Oh, man, that feels amazing. It's so big," Max said quietly and then he began to stroke it. Charlie loved the way it felt to have someone else holding his dick. Although smaller than his own, Max's hand was warm and had a firm grip. As Max began to stroke his roommate's big dick, Charlie smiled and sighed a bit and slowly lowered himself to lay back on the blanket. He enjoyed the smaller boy's attention for a while and then curiosity got the better of him and he slid his hand across the boys leg and took hold of his smaller but equally rampant dick. "Oh, yeah, Charlie. Your hand feels so good on my cock. Hmmm, stroke it for me." Both boys were now laying back in opposite directions, stroking each other. By necessity, their naked bodies were touching in various places, but neither seemed to mind. They were too fixated on the sensations that were spreading outward from their cocks. Max started to get more creative as he let Charlie's fat dick go to slap against his belly. Max began to play with Charlie's big ballsack for a while and then started to rub the underside of the meaty shaft, grinding the big dick into Charlies lower abdomen. Charlie murmured his appreciation and he copied some of what Max was doing. After a bit more, hands grabbed cock shafts and began stroking in earnest. Soon, boyish hips began to move involuntarily, adding to hands squeezing and sliding along the precum slicked shafts. Max started to push hard with his hips and soon he was staining against Charlie's strong grip as his cum shot out, falling back on his stomach and oozing over Charlie's hand. Feeling the warm thick liquid cover his fingers pushed Charlie over the edge and his hips bucked and his cum started to fly. As usual, his larger cum load fired well above his cock head, first splashing down on his torso and then Max pulled the big cock towards himself to have the last streams fall onto his own smooth chest and belly. The last of it oozed out to cover his own smaller hand. The two roommates lay there for a while until Charlie lifted his head and said, "Wow, that was so great. It's really a lot more fun when someone else is doing the stroking." "Yeah, your dick is so nice to hold and stroke," Max replied, still holding Charlie's slowly softening cock in his hand. "Is that something you do with your friend?" Charlie asked quietly. "Yeah, we started playing together this past summer. We were jerking each other off before the end of the first week." "Wow." "Well, he's a couple of years older so he knows more stuff to do." "Did he show it all to you?" Charlie asked. "Oh, yeah. We were doing lots of stuff by the end of the summer," Max replied. "What else can we do?" "First, we should get cleaned up," Max said, grabbing some paper towels and a small bottle of water. Charlie smiled and said, "Looks like you got the worst of it this time." "I don't mind. I love the way all that hot come feels on my bare skin," Max said. It didn't take long to get the thick cream off of themselves. Lack of body hair made for a fairly simple cleanup. The stayed naked, sitting on the blanket, side by side with their backs against Charlie's bed, legs stretched out in front. Their soft cocks and relaxed ball sacks rest against their thighs. "So what other kinds of things did you and your friend do?" Charlie asked. "Well, there are different positions for stroking each other, touching different parts of each others bodies." Max went on to describe how he and his friend spent a night together in the house alone. He said they probably came half a dozen times with the last being almost cum free but still with very intense spasms. Charlie was wide eyed and his cock began to stir. "Then during the last couple of weeks he taught me how to suck a guy's dick," Max said, blushing a bit in the low light of the reading lamp. "Geez, really? I don't think I'm ready for that. I think I'll just stick to jerking off for now." "That's cool," Max said, although there may have been a bit of disappointment in the boy's tone. "So, you know, we don't have to get up early tomorrow. Do you want to do it again, since you said you did it all those times before." "Yeah, sure," Max said, looking down and seeing that gorgeous cock start to swell. "Maybe we could try and do it differently this time?" "Cool, what do you have in mind?" Charlie asked eargerly. "Let's stand up, facing each other," Max said. "Okay." The two boys got up off the floor and stood a couple of feet apart. Both were starting to stiffen, Max's smaller cock sticking up while Charlie's heavier one was more horizontal. Without saying anything, each reached out with their right hands to take hold of the others cock. They both sighed. "I love how your feels on my cock, Max." "Not as much as I love holding it," the smaller boy said, thoroughly enjoying how Charlie's hand felt on his dick." They started stroking each other. Max reached over with his free hand and began to ply with Charlies heavy ball sack. Charlie sighed again, a bit louder this time, and could feel his precum starting to flow. As he looked over at Max he could clearly see the boys nipples standing out hard and strong. He recalled that sometimes when he was jerking off in the shower he would play with his own nipples, so instead of going for Max's balls he used a finger to lightly rub one of his nipples. Max groaned under his breath and then said, "Oh, yes, Charlie, Use some of your precum as lube. It will feel so much better." Charlie did as Max asked and was rewarded with the boy's renewed groan as he then let his head tilt back, his eyes closed. Max then reciprocated, letting go of the big pair of balls and using his own precum to get Charlie's nipples slippery and hard. It wasn't long before their hips started to move and they began fucking each others hands. Max took things a little further when he stepped a bit closer and took Charlie's cock and rubbed the slick head against his own cock. Charlie's eyes flew open and he looked down to see the two swollen spongy cock heads pushed together, the precum from both mixing together and he pushed his hips forward to increase the pressure. Max was loving it, but he was really surprised when Charlie let go of his cock and used both hands on his bare ass and pulled the smaller boy up tight so that their bodies were grinding together. Due to their height and size mismatch, their cocks were only partially rubbing on each other. Charlie wanted more so he moved them back to where he could sit against his desk lowering his waist to a level with Max and with legs spread he pulled the smaller boy in tight, their cocks fully engaged now. Max leaned forward so their bodies were pressed against each other, his head on Charlie's shoulder. "Oh,god, Charlie, you feel so good against me and holding me like this," Max murmured into Charlie's shoulder. Charlie just growled low in his throat. He kept squeezing Max's tight ass cheeks, keeping their grinding hips together. Max let his arms slide around Charlie's bare back, his hands roaming over the smooth, warm skin. They continued to dry hump each other like this for some time with large amounts of precum smeared on their cocks and bellies. Max finally pulled back, his eyes lidded and his breathing ragged. He dipped his head down and began to lick Charlie's hard nipples. Charlie groaned more and his hips bucked twice before the first heavy stream of cum fired out of his cock up between the two boy's bodies and splashed against Max's chin and neck. He pulled back reflexively and caught the next shot in the face, causing him to gasp, then laugh. He started cumming as well, adding to the mess that was forming between the two. As both boys spewed out their cum, their hips remained pressed together, grinding as they rode out their orgasms. As their intense spasms began to fade, Max slumped against Charlie, his forehead leaning on the larger boy's shoulder. Charlie had to move his hands to rest on the desk behind him to hold them both up. Max began a low mutter. "Oh, damn, Charlie. That was so great. I love how you feel against me and all this hot cum between us." Charlie laughed good naturedly. "You really love this guy on guy stuff, don't you?" "Oh, yeah," the boy sighed, "I love the look and feel of a big hard cock." "I guess you'll need to show and tell me more, but not now. We need to get cleaned up." "Yeah, you sure do make a mess when you fire that thing off." As he sat on the bed in his college dorm room, Charlie had to smile again when he thought about all the adventures he and shy little Max had during those four years and how the boy had never seemed to lose his fascination with Charlie's big cock and copious cum loads. The fact that by the time he graduated from the prep school his cock was close to ten inches long probably had a lot to do with it. As it turned out, little Max had a lot to show Charlie. Apparently it had been quite an educational summer for the the boy. Charlie especially enjoyed laying back on the floor and having Max straddle his hips and grab both of their cocks and squeezed them together using both of his small hands. The addition of some form of lubricant, which varied depending on what they could find, made it much more fun. They carried on in this way all through the remainder of the semester until the night before they were heading home for the Christmas break. It was to be an early morning so they settled for a single load of cum and then they turned in. As Charlie slept, he began to dream of floating on a warm soft cloud, just drifting along. However a more basic sensation began to intrude on his sleep and as he woke up he found that the warm wet sensation was centered on his cock. Looking down toward his feet he saw Max kneeling by the side of his bed, both hands holding the base of Charlie's cock, his soft wet lips sliding up and down. He was able to get about half of the thick shaft into his mouth. "Oh, Max, what the hell are you doing," Charlie asked in a low, moaning whisper. Max slid his mouth off Charlie's cock and looked at him, his eyes bright. "Don't stop me, Charlie, please. I love your big cock so much. Let me do this as a Christmas present for you," he said and then gave the cock head a few more licks. "Oh, shit, yeah, go ahead Max, don't stop." Max began sucking with renewed enthusiasm and Charlie just punched up his pillow so his head was elevated enough for him to watch. The smaller boy could only work half the big dick in but he was slobbering enough to coat the rest and have it run down over his hands. Max then let go of the Charlie's cock entirely and feverishly worked to get Charlie's boxers down his legs. Once he had them off and tossed to the floor, he pushed Charlie's legs apart and began to lick and and suck on the big smooth balls as he stroked the big slippery cock shaft. Charlie was losing himself in the intense feelings that Max's warm wet tongue and lips were giving him. He groaned and flexed his hips when he felt Max's lips slide back over his oozing cock head. He brought his hand to rest on Max's bare back and as he explored he found that the boy was completely naked as he knelt by the bed. Reaching down he took hold of the smaller, but equally hard cock, feeling the slick oozing fluid as he rubbed it into the hot smooth skin. Max moaned around the dick filling his mouth. Charlie squeezed and stroked the shaft then let his hand cup and fondle the tight ball sack. As an added touch he let the heel of his palm press against the hot little cock and he rubbed it against Max's belly. Max's hips began to swing and grind and his legs slid a bit further apart. Charlie let a finger slide past Max's balls and rubbed on the root of his cock before sliding to the puckered little asshole and he began to rub it. Max moaned heavily around Charlie's dick as he pushed his ass down against the probing finger. In response to the feelings coming from his asshole, Max began to push Charlie's legs apart and licked his way down the big shaft and over the wet shiny balls. He was trying to get his tongue in between Charlie's cheeks but couldn't. He finally scrambled up on the bed, got between Charlie's legs and pushed them wider and back a bit. He used his small delicate fingers to pry the hard cheeks apart, exposing a pink, tight ring. He attached it with his tongue, licking and probing. Charlie hissed, "Oh, shit, Max, what are you doing? Oh, yeah, that feels so amazing." Afraid of crying out, Charlie grabbed his pillow and held it over his mouth. His hard cock lay like a steel pipe against his belly, leaking precum. All the oral attention was proving to be too much and he finally pulled the pillow away and muttered, "Oh god, Max, I'm going to cum." Max let go of Charlie's ass and scrambled forward to grab that big dripping cock and clamped the head between his lips. He sucked and stroked until Charlie's ass bounced off the bed once and then his balls emptied. To his credit, Max tried to capture all that creamy flood but he failed miserably after the second spurt. The thick white liquid began leaking out of the corners of his mouth. He was forced to open up and back off, letting the remaining shots hit the top of his mouth and then run out over his chin and onto Charlie's cock and stomach. As Charlie's flow ebbed and his own need peaked, Max slid up on his knees and aimed his dripping dick at Charlie's cock and stroked furiously for a moment and then began shooting his load. It was the hardest he ever came, four strong solid jets of cum splashed onto Charlies cock and balls, followed by some oozing dribbles. As his orgasm subsided so did Max's ability to stay upright. He folded forward and wound up laying on top of Charlie, who brought his hands up to rest on Max's ass. When the alarm went off at 6 AM, they were still in that position. They both started awake and Max scrambled off of Charlie and then off the bed. He stood naked next to the bed, dried cum clinging to his bare skin. It appeared he didn't know what to do. Charlie looked at him and gave him that easy smile. "Relax, Max. It was a lot of fun. Right now we need to get into the showers and get ready to go home. It's all cool, okay?" Max smiled a bit but looked relieved. "Thanks, Charlie. I just couldn't help myself. And you're right, it was a lot of fun." They pulled on robes and headed for the showers and got cleaned up, no one the wiser. They were both on their way home by eight. As Charlie sat in his new dorm room he remember how dull vacation was. He only managed a couple of shower sessions and there was no one there to lend a hand. When he and Max got back to school they tried to make up for lost time with the smaller boy sucking two loads out of Charlie's big dick, who then tried his hand at sucking a cock. While not as enthusiastic as Max, he did it well enough to get a nice load out of the boy, watching from close up as it shot from the smaller cock. This set the pattern for the rest of the year. Nearly every night, he two shared some form of oral sex or jerking off, usually combined. Charlie particularly enjoyed having his ass licked and Max was an avid rimmer. On the night before they left for the summer, Max even persuaded Charlie to slip his finger up the boys tight ass and finger fuck him. Max's orgasm was so intense he collapsed onto the bed and it was over half an hour before he could bring himself to resume the session. When they parted company to head home, Charlie had to wonder what he was going to do with himself all summer. He was sure he didn't want to do it alone.