Date: Sun, 31 Jul 2011 19:10:11 -0400 From: Sam Sheppard Subject: Memories of Sixteen 8 Disclaimer: This story is true and happened just as it's written. Some literary license has been taken. The names have been changed for obvious reasons. If you are under 18 years old or offended by gay sex then please leave this site immediately. As a side note, part way through this chapter there's a short episode of hetero sex. I hope that doesn't offend anyone, but for the sake of accuracy, I had to include it. Memories of Sixteen 8 Next day, Shawn called me and asked if he could come over and swim at our pool. His folks had gone to work and he was sitting around his place doing nothing. Of course I told him to come right over and to call his parents to see if he could spend the night. Shawn and I often stayed at each other's place, so his folks said yes. I called my parents at work and they agreed. He must have already had his stuff together because he was at my door in like 5 minutes. Since I didn't have to be at the pool for a couple of hours yet, we decided to watch some TV, so we went into the den and sat down. Shawn and I got bored pretty quickly. There wasn't a lot of programming at that time of the day for guys our age. So I suggested we check out the new magazine I had in my room. Shawn plopped down on my bed while I fished in my underwear drawer for the magazine. Fortunately, my mother, after she did the laundry, would leave it in the basket on my bed for me to put away and didn't open my drawers. I pulled out the latest issue of Playboy and dropped onto the bed beside Shawn. We immediately opened the magazine to the centerfold and Miss July 1972 and all her charms greeted us. We lay there staring at the pics and slowly turned the pages until we got to the section where people wrote about their sexual encounters. You know, the ones that began, "I never believed the stories here, until..." So, Shawn and I were lying on my bed, reading the stories and very definitely getting aroused. We joked about writing a story and sending it in. Our joking around turned into kidding each other about how excited we were getting and with that we decided to take care of the problem. We both quickly stripped out of our clothes and lay back on my bed, lying with our legs and sides touching each other. Shawn and I reached over and took hold of each other's hard dicks and began stroking each other. I never failed to marvel at how big Shawn's penis was, especially when my hand or my mouth were wrapped around it. I could just get my hand around the girth of his cock and my jaw always got sore from having to stretch so much as I sucked him off. I loved watching his cock and his face when he came. We started jerking each other off in earnest and soon I could feel his big cock getting even harder and watched the head becoming even more engorged. I quickly knocked his hand away from my twitching dick and twisted so I could take the head of his cock in my mouth as I jerked him to orgasm. I sped up and began gently kneading his balls and was rewarded with Shawn crying out, "Oh fuuck, Sam, that's awesome, oh shit, so good, oh fuck, oh fuck, I'm gonna cum, oh fuck, oh fuck, oh FUCK, OHHHH FFFFUUUUCCCCCKKKKK," and with that I felt Shawn's hot, thick cum splash against the back of my mouth and onto my tongue. His legs were jerking and I looked up and saw his eyes were closed and his mouth was open as he panted while he came down from his orgasm. I kept my hand wrapped around his slowly softening member and could feel his heartbeat in it as it slowly shrunk. Once it had, Shawn grabbed me and literally threw me on my back on the bed. He dove down onto my cock and completely engulfed it in his mouth. It felt so warm and soft and he started bobbing his head, driving his talented lips and tongue up and down my throbbing shaft. He'd occasionally pull his mouth off of me and lick my shaft, head and balls and then go back to sucking me. It didn't take long before I felt myself nearing the point of no return and I started moaning and thrashing. Shawn tightened his lips and increased his suctioning on my cock, which drove me right over the edge and with a loud growl I lost all control and began blasting my teenage cum into his waiting mouth. "Mmmmm, nectar of the gods," Shawn chuckled. "You are such a fag!" I kidded him. "Yeah, but so are you," he responded. "Oh yeah? ... Oh yeah, you're right," I laughed and then we both started laughing and then wrestling. I stopped wrestling when I noticed the clock. It was 11:30 and the pool was supposed to be open by noon, so we had to stop and quickly get dressed. This was somewhat complicated by the fact that our wrestling had produced the usual effect and Speedos just didn't fit well over boners, especially one the size of Shawn's. We finally got our problems sorted and our dicks shoved into our suits, threw on some shorts and T-shirts and headed down to the pool. I barely had enough time to clean the pool before I had to open it. Shawn and I sat at the end of the pool and joked around while I did the lifeguard thing. It was around 2 when Stevie showed up and came over to say Hi. I introduced him to Shawn and he dropped his beach towel beside my chair and lay down on his back to get some sun. Stevie's fourteen year old body was completely on display for our eyes (have I said how much I loved Speedos?). Shawn looked at me and raised his eyebrows as if to say, "Cute kid, eh?" I raised mine in response, smiled and nodded. Shawn tilted his head, pointed at Stevie and gave me a look that said, "You didn't, did you?" to which I simply smiled and nodded again. Shawn mouthed "Cool," and looked at Stevie's cute body again. I could see he was interested, and for a second the thought of my best friend and my "little brother" getting together really bothered me. I went back to keeping my eye on the pool and just enjoying the sun. Lane showed up a short while later and came over as well. I also introduced him to Shawn and he dropped his towel next to Stevie. Shawn looked at me and smiled. I smiled back and nodded my head slightly. Shawn just sat there and shook his head. Then the rest of the guys showed up, including Mike, and everyone, except me, jumped into the pool. The guys invited Shawn to join them and the next thing I knew there was a major splash war going on. I should have broken it up so as not to disturb the other swimmers, especially the older folks, but fortunately, once the guys had all gotten in, the old folks had gotten out, leaving the pool to the boys. The guys horsed around for about half an hour, splashing, playing tag and jumping off the board and then I had to chase them out so the other people could use the pool. Bill and Bob left and went upstairs, Mike dropped onto his towel face down and Freddy pulled out a book, lay on his stomach and started to read. Lane and Stevie had returned to their towels and were also laying face down getting some sun on their backs. Shawn flopped in to the chair and shook his head, spraying me with water from his long hair. I jumped and yelled and Shawn laughed, which started me laughing. By about 5 pm most of the people had left the pool, leaving me, Shawn, Stevie and Lane sitting there. Stevie's mom came down to the pool and told him he had to go upstairs, so he gathered his stuff and off he went. Just before closing time, Lane told us his parents had gone out and he wanted to know if we wanted to go to his apartment for a while. I wasn't sure that was such a good idea. If his folks suddenly came home to find two sixteen year old guys hanging out with their twelve year old kid, there would be a lot of uncomfortable questions and we could be in deep shit. I suggested we try to get together another time and he reluctantly agreed. Shawn and I went up to my place and had dinner with my parents. After dinner Shawn and I went into the den to watch All in the Family and my dad listened to the Argos play Winnipeg on the radio. My mom went downstairs to one of her friend's apartment to play MahJongg. Shawn and I finished watching TV and decided to call it a night. We went into my bedroom, closed the door and got changed. Up until now we'd been wearing our swim suits under our shorts, so we needed to change into some underwear. Both Shawn and I wore boxers, so we kicked off our swim suits and pulled on our boxers. I stuck my head out of my door and yelled "Good night" to my dad and then we lay down on my bed and grabbed the Playboy. My parents would never dream of walking into my bedroom without knocking and when Shawn was over they wouldn't even think about bothering us once the door was closed. I sometimes wondered if they knew what we did behind closed doors and decided that they were OK with it. When you're sixteen, parents can be hard to figure out sometimes. Shawn and I were reading the magazine (we really hadn't gotten very far earlier) and we boned up pretty quickly. It just felt so good lying there with my best friend knowing that I could be who I was and say what I wanted with him that it actually took my breath away. I reached into the opening in Shawn's shorts and rubbed my hand up and down that magnificent cock of his and through his curly blonde bush, feeling his dick grow to its full eight and a half inches. I took my hand out, reached up and dragged his boxers down and off him. Like I said, I wasn't worried about my folks bothering us. Shawn laid there in all his 6'3", blonde, sixteen year old glory, his cock sticking up and arcing back toward his flat stomach. It's a sight that was burned into my memory for ever, and when we meet now (we're still good friends) almost 40 years later, I can still see him like that. Shawn had his eyes closed and one arm behind his head. I moved up, leaned in and began kissing and tonguing his chest and nipples, slowly working my way down to his stomach where I stuck my tongue in his belly button and wiggled it, tickling him. He laughed and his stomach tensed up. I slid my tongue down his abs until I reached the top of his pubes and then nuzzled my way around his bush for a minute or so, feeling them tickle my nose and lips. I kissed around the base of his cock and down to his balls, occasionally gently nibbling on them, causing Shawn to utter little gasps. I sucked first one and then the other of his teenage testicles into my mouth and rolled them around, feeling the crinkly skin of his scrotum, and the curly hairs, on my tongue as well as the soft, spongy, hardness of his balls. I let go and licked my way back up to the base of his shaft and then up it to the swollen dark pink crown, where I stuck my tongue in his slit and wiggled it around a bit and then took the whole head in my mouth. I looked up and Shawn still had his eyes closed but now he had a smile on his face. Sliding my lips down his shaft, I gradually worked most of his enormous cock into my mouth, stopping when I just couldn't get any more in. I stayed like that for a minute to get used to the stretching of my jaws and then began pulling back up the shaft until just the tip of his head was in my mouth and then plunging back down as far as I could go. After a few times, I felt Shawn grab my head and lift me up. He whispered to me, "Swing around, I want to do you at the same time." Who was I to argue? So we rolled onto our sides and I swung around with my hips at his head. He pulled my boxers off, grabbed hold of my penis, which was at full mast and throbbing and took it straight into his mouth. I dove back down onto his cock and we started sucking each other for all we were worth. Pretty soon I could feel myself getting close and I could tell that Shawn was at about the same point. His massive dick was throbbing, his balls were up tight against his abdomen and he was panting like a race horse. The other really good clue was that he said, "Oh God, Sam, don't stop. I'm gonna cum." Shawn began to moan and thrash his hips back and forth and a low growl escaped his throat (my parents didn't bother us, but they didn't need to hear us either). His cock stiffened even more, the head swelled and his cum started splashing into my mouth. Just as he started to shoot, I felt that sensation in my cock that let me know I was there too and I began cumming into Shawn's mouth, trying hard not to scream. We both lay there, panting and sweating, with the remains of each other's cum in our mouths and I swung around and we hugged. After we cooled down a bit, we climbed in under the sheets and I snuggled in against Shawn. He put his arm around my shoulders, I laid my head on his chest and within minutes was fast asleep. We slept like that all night and I woke the next morning in exactly the same position. The next week was unremarkable, as I didn't get to spend any time with Lane or Stevie, other than at the pool. I went out on my date with Sandy on the Friday. We both thought "The Godfather" was awesome and talked about it all the way home. As I was driving home, Sandy brought up the subject of what she'd seen at the pool. I just about swerved off the road. I apologized for making her uncomfortable, but she said she didn't feel uncomfortable, as a matter of fact, she'd kind of like to see it again. I almost hit the curb that time. My heart was pounding and I could hear the ocean in my ears. "What the fuck am I gonna do now?" I thought. "Ummm...OK," I stammered. "We can't go to my place, my folks are home. What about yours?" "No. My parents are home too," she said. I was thinking fast and furious and suddenly realized that there was a park near where we were that some of the guys at school talked about. It was a large park with a couple of roads that wove through it with a bunch of parking lots. Maybe we could go there. I suggested it and Sandy readily agreed. As I was driving, I kept thinking, "What am I gonna do here?" And then I realized that I was already hard and since I was supposed to be straight, I might as well go with the flow. Sandy and I reached the park, followed one of the lanes and found a secluded empty spot. On the way, I noticed there were quite a few cars with steamy windows parked at various spots. I parked the car and turned it off. We undid our seat belts and Sandy slid over towards me but we found that the bucket seats were fairly restrictive so I suggested we climb into the back seat. Once there, we began kissing and when Sandy stuck her tongue in my mouth, I went from half to full mast at once. She dropped her hand onto my crotch and began rubbing me through my tight jeans, which were now becoming extremely, uncomfortably tight. I responded by reaching over and taking hold of her breast and rubbed and tweaked her nipple. Within minutes she had her shirt off, I had my pants undone and the car windows were starting to fog up. One thing followed another and pretty soon my jeans and boxers were around my ankles and Sandy was sucking my cock (I have to say here that while this was actually pretty enjoyable, her skills didn't come anywhere near either Stevie's or Shawn's). I was playing with her tits, as I'd removed her bra and next thing I knew Sandy's pants and panties were off and she was straddling me. She lowered herself onto my rock hard dick and I felt a firm resistance. She repositioned herself and slowly lowered down again. I felt something give, Sandy cried out and I was buried to the hilt in her pussy. We fucked for quite a while, all the time Sandy was moaning and I was wondering if this was what it would feel like fucking Stevie or Lane. I felt my cum building and asked Sandy if she wanted me to pull out. She said no, she was on the pill. So as my orgasm hit, I thrust deep into her, imagining it was Stevie's ass and blew. As I bucked and thrust, Sandy started to tremble, cried out and I felt her pussy contract and release repeatedly around my pole, milking me of the last drops of my semen. We both collapsed against the back seat and began kissing again. After a minute or two, my soft cock slipped out of her pussy with a plop. She moved off me and I pulled up my boxers and jeans. Sandy got dressed and we got into the front seats and kissed some more. Then I started the car and drove her home, her hand resting on my now soft cock most of the way. I walked her to her door, we kissed and made plans to go out the next week and I went home and jumped in the shower. I was sure my parents could smell that we'd had sex as I walked in the door, but they were discreet enough not to say a word. I showered, pulled on some boxers and, exhausted as much by the sex as by the stress of worrying about the date, went right to sleep. It was Saturday and this Saturday my mom was scheduled to play Mahjongg at a friend's place and my dad was off to an Argos game at Exhibition Stadium downtown. That meant that I had the apartment to myself until at least 11 o'clock. And to make things even better, the weather had turned somewhat chilly, as it will do from time to time in Toronto. So this meant that while I had to open the pool, it was unlikely that anyone would be swimming and I could close early. I called Shawn and told him to come over. I just had to tell him about Sandy and I figured maybe I could also get Lane or Stevie over as well. Shawn showed up and we went down to the pool and opened it. As I'd thought, no one was interested, but I had to keep it open for a while, just in case. All of a sudden Lane dropped by, so we started shooting the breeze and I asked him if he'd be interested in coming upstairs with Shawn and me. His face brightened and he said, "Sure I would. When do you want me there?" I told him to just hang here for a bit and then we'd go upstairs. After about another half hour it was obvious that no one was going to show, so I decided to close the pool. I locked everything up and the three of us went up to my apartment. We had around six hours to have some fun. Once we'd gotten in the door and I'd locked it, we all started shedding clothes. We were all completely naked in a flash. We grabbed our clothes and went into my bedroom and all lay down on the bed. I had to hand it to Lane, not many twelve year olds would trust two sixteen year olds, but here he was. I watched Shawn as he eyed Lane. His interest was obvious and not just from the way he looked at the naked twelve year old. Shawn was hard as a rock and he was flushed. Lane looked at Shawn's cock, his eyes opened wide and he said, "Holy shit, look at the size of that! How big is it?" I replied, "Last time we measured it, eight and a half inches." "Fuck," he said, "That's twice as big as mine! Can I feel it?" Shawn assured Lane that that was exactly what he wanted Lane to do. Lane reached over and tentatively touched Shawn's shaft. His hand didn't get all the way around that monster. Shawn sighed and Lane began stroking Shawn's dick. It was incredibly exciting to watch this naked twelve year old boy stroking my best friend's penis. I reached over and started jerking Lane's cute little cock. Lane asked Shawn if he could try sucking his cock. "Sure," Shawn said, "I'd like that, but don't hurt yourself." Lane moved up and knelt beside Shawn and holding Shawn's cock in his both hands he lowered his sweet mouth onto Shawn's rigid penis. He was only able to take the head in at this point, but he made the most of it, nodding and bobbing his head and rocking back and forth as he sucked on my best friend's rod. His tight, white, hairless ass was in the air as he did this and I couldn't help but move up and start kissing and licking his firm globes. I reached between his legs and started kneading his nice size balls as I licked everywhere across that ass. I spread his cheeks and there was his cute little pucker, open to my sight, and now my tongue. I dragged my tongue down his crack and right across his opening, causing Lane's head to snap up and off Shawn's cock. He quickly looked back at me and smiled and went back to blowing Shawn. I continued to lick and kiss Lane's adorable twelve year old ass and down across his perineum to the back side of his wrinkly sac and his balls. As I did this I couldn't help but wonder if Lane would let me fuck that gorgeous ass of his. I decided to experiment and see just how far I could get, so I wet my middle finger and put it against his pucker. I started wriggling it against his hole and in a short time he'd relaxed enough that it slipped in up to the second knuckle. I began to twirl it in his hole and I could feel his sphincter tighten up on my finger. Lane responded by moaning while he had Shawn's cock in his mouth. Once his opening relaxed, I slid the rest of my finger in and let it rest there making sure Lane wasn't in any discomfort. I slowly started to push it in and pull it back and Lane let out another moan. After a few strokes, I pulled out and Lane stopped sucking Shawn, looked me and asked why I taken it out. I told him to hang on and ran into the bathroom to get the Vaseline. When I returned, Lane was back sucking Shawn and his ass was in the air. I lubed up two fingers and then Lane's hole and slid my middle finger back in. Now, with the lube and his previous experience it was much easier to get my finger into Lane's pucker. I wiggled it for a while, trying to avoid the lump in his ass (his prostate) for now and then slowly slid the tip of my second finger against his opening. It slipped in and I felt Lane tighten up so I let it rest there. I could hear Shawn starting to moan and watched as Lane slid up and down Shawn's huge pole, gradually getting more of Shawn's cock in his mouth. He had the entire head and what looked like the first couple of inches in his widely stretched mouth and saliva was dribbling out the sides of his mouth, running down Shawn's rod and pooling in his pubes. Lane's eyes were closed and he just looked like he was really enjoying himself. It was time, I thought, so I gently pushed the rest of my second finger into Lane's rectum and started rotating both fingers. Lane took his mouth off Shawn long enough to cry out "OH GOD!!" and then plunged back onto Shawn's piece of meat. I rotated and sawed my fingers in his ass for a few minutes and felt Lane push his ass back against my probing fingers. I decided that it was now or never, so I pulled Lane up off Shawn's cock. He looked bewildered. "Listen, I want to try something and I wanted to see if you'd be ok with it first," I began. "Your ass is driving me crazy and I want to try putting my cock where my fingers have been." "You mean you want to fuck me," he said matter of factly. "Will it hurt?" "It might, but I think I have you stretched pretty well right now, so it shouldn't be bad. But if it hurts, I'll stop and pull out, OK?" He looked unsure and said, "Well, I guess so, but you'll stop if I say, right?" "Definitely," I replied. "I don't want to hurt you, ever. You let me know and it won't happen." "OK," he said, "Let's try it." I was having the same reaction as when I was in the car with Sandy, my heart was pounding and I could hear the ocean. I repositioned Lane and he went back to sucking Shawn, who was now intently watching what I was doing at the other end of the boy. I slid my fingers back into Lane's ass and started to push in and pull out. As I did this, I reached over to the Vaseline and, grabbing a good amount, lubed up my aching cock. It was harder than I remembered it ever being, or so it seemed, as I pulled my fingers out and positioned it at the entrance to Lane's most private part. I asked him again, "Lane, you sure you're OK with this?" and he simply nodded yes. So I spread his cheeks, put the tip of my cock against his hole and holding it in one hand and Lane's hip in the other, pushed my head against his soft pucker. It slid part way in and hit some resistance, so I pulled back and tried again. This time, when I hit the resistance, I stayed where I was, trying to let Lane get used to the pressure. In a very short time, I could feel his anus relax and slowly the head of my cock slid into him until it was completely inside my boy. Now I had to rest or I was going to cum. His ass was so much tighter than Sandy's pussy and hotter as well. I couldn't take much more waiting, so I started sliding more of my clock into him, feeling like I was pushing my dick into a warm, moist glove that wrapped itself around my shaft. His sphincter was clamping down on me and releasing and I could hear him panting and making little high pitched moaning sounds around Shawn's cock. With each thrust, he slid farther down Shawn's pole and I slid deeper in until I could feel my pubes right up against his smooth cheeks. Looking down, the sight of my cock buried in this kid's ass just about made me cum right there. I asked Lane if he was OK and he mumbled, "Unnhh-hhuh." The feelings were way too strong, and I'd love to be able to say I fucked him for hours, it was only about three or four thrusts and I couldn't take it anymore. "Oh holy shit, oh my god, oh god," I moaned with each thrust. "So tight, so hot, oh fuck, unghh, unghh, unghh, unghh , Oh fuck, cumming, cumming, cumming, OOOOOHHHHHH FFFUUUCKKKK," I screamed as I unloaded what felt like the biggest cum of my young life into Lane's ass. I thrust and thrust and as I came, held onto his hips and pulled him back, mashing my pubic mound against his ass. Lane later said he could feel every shot of my cum squirt into him. I collapsed across Lane's back, keeping my still oozing cock buried in his ass and watched as he sped up his oral and manual ministrations on Shawn's cock. Shawn was soon bucking his hips off the bed and I watched his face as well, to see the telltale signs of when he was reaching orgasm. It didn't take long. His face contorted into a grimace, his neck muscles stood out, he broke into a sweat and his eyes screwed up tight. Shawn started panting and writhing and held Lane's head with both hands, bucking his hips and cock up into Lane's mouth. With a roar, Shawn blew his load into Lane's mouth. Lane did his best to swallow as much as he could, but with his lips stretched by the massive girth of my friends' penis and the amount of saliva he'd been producing as he sucked Shawn, a fair amount leaked out at the sides of his mouth and ran down Shawn's cock to add to the moisture already there. Lane collapsed down onto Shawn, I collapsed onto Lane and my softening penis slipped out of his ass. We rearranged ourselves on the bed with Lane lying in between Shawn and me. I leaned over and kissed Lane, slipping my tongue into his mouth, this time tasting my best friend's cum in my little lover's mouth and gently began stroking Lane's rock solid 4 inch boner. Shawn and I had gotten off, and now it was Lane's turn. I kissed my way down his little body and into his sparse pubic hairs, licking at the base of his penis and around down to his balls. I then engulfed his entire cock in my mouth and began sucking Lane for all I was worth. As I did, I ran my fingers down under his balls to scratch at the sensitive skin between his balls and his ass and found myself coming away with sticky, wet fingers from my cum leaking out of his ass. I used some of my cum to lube the base of Lane's cock and began pumping his cock with my hand at the same time I was sucking on his head. He lasted maybe a couple of minutes and soon his hips were thrusting that sweet little penis deep into my mouth and he was mumbling incoherently. I could feel his cock begin to twitch uncontrollably and his balls draw up and knew he was about to cum. I slid my mouth all the way down his cock, right up against his pubic mound and used my tongue and throat to milk his penis. With a screech, Lane began cumming in my mouth. I could taste the warm, nutty flavour of this adorable, willing boy and savoured every drop. Lane slowed down, his breathing become regular and his penis stopped spurting. I held him in my mouth until he asked me to take it out because it was too sensitive. I swallowed, slowly drew my lips along his rapidly softening shaft and licked my lips. Shawn had been watching this and, one of the miracles of being sixteen, had a boner again. It was getting late and I wanted to make sure Lane was gone by the time my parents got home, so I suggested we jump in the shower, yes, all 3 of us, and clean off before we got dressed. I went into the bathroom and got the shower running and then went back to let the guys know it was ready. Lane had hold of Shawn's cock and was starting to jack him off, but I had to interrupt and remind them of the time. We all climbed into the shower and washed each other off. I paid particular interest to cleaning Lane's ass and opening his hole to drain any of my cum that may still have been in there. It would never have done to have him go home with cum leaking out and staining his shorts. Once I was sure he was clean we climbed out, dried each other off and got dressed. We went to the apartment door and Shawn and Lane hugged and then Lane and I exchanged a truly passionate kiss. I told him how happy he'd made me and he replied that he was really happy he'd let me do it. He said it felt amazing and was looking forward to doing it again. With one last kiss, Lane was off and I suggested to Shawn that he spend the night, which he did. We had plenty to talk about and relive that night.