Jimbo

It was our second full day of summer break of 1990 and my friend Zach and I were enjoying the day hanging out by the lake. We were both glad to be finally done with middle school and decided to spend the day away from the folks. Man I was glad the place wasn’t busy that day, just two older boys who were fishing when we arrived. We tried fishing for an hour but caught nothing so Zach suggested we swim for a while. Normally we would’ve changed into swimshorts at home, but the year before we discovered a small clearing in the trees on the bank where we could change and since then we always brought swimshorts to change into when we got there. I knew it was secluded, but neverthanless I always checked before going back there to change to make sure nobody could see. I was a 5′ scrawney, dark-haired, 15 y.o. who hadn’t even got much hair anywhere yet, let alone “downstairs”. Thank god I tanned easily or I wouldn’t even have wanted to take my shirt off when I swam. I do have to admit that my dick was a little larger than the other guys in my gym class at the time. My friend Zach however was not your typical average teenager. He stood 5’7″ at the time, swimmer’s build, bleach-blond hair, and ice-blue eyes that looked like they would stab you if you pissed him off. He tanned just as easily as I did, which with all of it put together, had the girls coming after him.
Anyway getting back on track, I get back there to change and Zach has already stripped out of his shorts and underwear wearing only his shoes, socks, and t-shirt with his butt facing me.
“Was wondering when you were coming back to change, slowpoke!”
“Just checking things out, making sure nobody can see.” I said.
“I keep telling you it’s secluded dummy, I proved it even furtur when my folks and I came down here yesterday.” he said with a sheepish look on his face, then he wispered “I stripped naked and jacked off right here!”
“What?!! And you didn’t get caught?!!” I wispered back.
“Nope and I swam out towards the middle of the lake pulled my shorts down to my ankles and even did it out there too!”
“Damn!” I said “I don’t think I would be brave enough to do that!”
“Well when you realize nobody can tell if you have shorts on or if you’re naked once you are under the water, you should try it, it feels great.” he said scratching at his crotch, then said “Damn man, with all this sex talk, I’m sprouting wood over here!”
“Really?” I asked, like a dummy.
“Yup, check it out.”
Zach was like that, not ashamed at all, he was the first of us to change in front of the other, the first of us to sleep naked, and even the first one to jack-off in front of the other, so it was no suprise when he turned around to show that his dick had grown from it’s soft state of 4 1/2″ to (by 15 y.o. standards) a 6 1/2″ snake!
“Man I still can’t believe how huge that thing is!” I said, shaking my head.
“6 1/2 inches!” he said beaming.
“I know, you had me measure it the last time we jacked-off, remember!” I said, noticing how he blushed after I said it.
“How big are you, did you measure yours yet?” he asked, now it was my turn to blush.
“No, not yet.” I said, laughing a little.”At least not when it was hard.”
Then the little shit pulled out a tape measure and said “Swiped it from my mom’s sewing room, she has several so she won’t miss it. Take those shorts and underwear off and get yourself hard so we can measure it.”
I wasted no time stripping to my shoes, socks, and t-shirt as well. It only took me ten strokes on my dick to get it from my soft state to raging hard-on.
“Ok, now hold still so I can measure properly.” he said, kneeling in front of me and placing one end at the base of my dick above my ball-sac. I never had anyone touch my dick like that before, (other than the doctor when he did physicals for school or scouts, but then I never had a hard on during those times) and I thought I was about to shoot a load right there. But I managed to keep my cool.
“6 inches!” Zach said, wide-eyed “Not bad bud, not bad at all, I thought you looked like you were getting close to my size the last time we jacked-off! Have you measured it when soft?”
“Yup, 4 inches.” I said.
“Wow, just about as big as me there too, I’m 4 1/2 inches!” he exclaimed.
“Duh, I know you goof!” I said, “You told me that before you had me measure your boner!”
“That’s right, I should’ve remembered that as well. Oh, well! Let’s get some swimming in.” he said, pulling his swimshorts up over his softening boner.
When we got out from our changing spot we noticed the two other boys were coming back from their fishing spot with a bucket containing their catch. We then recognized them as high school students from our town.
“How did you guys do?” we both asked.
“Not bad, caught 10.” they said, as they got into a van driven by a lady we assumed to be one of their mom’s, “See ya’ later!”
“Bye!” we said, waving.
The water was surprisingly warm, considering it was only the upper 70’s, lower 80’s for the past 5 days, I figured it would’ve been colder. We swam out a little ways to only where the tops of our shoulders and our heads were above the water, then started roughhousing. Then we got started talking about the hot girls in our school and how we would like to bang them, given half the chance.
“Oh my god dude!” Zach said, “All this talk about sex and I’m springing wood again!”
“Damn, you sure get horney a lot! And I thought I was bad!!” I said, snickering.
“Shut up man!” he said jokingly, “But I’m serious, I’m so hard right now that I’m thinking of pulling my shorts down to my ankles and jacking-off right here and now!”
“Dude, what if someone sees?!” I said, nervously looking around.
“Look around man, nobody’s here.” he said, waving his arm around and grinning. “Besides, no one can see anything but our shoulders and our heads above the water, so we’re safe to do it if you want too.”
“Well every since you mentioned it earlier, I was wondering what it would feel like.” I said in a low voice.
“If you want too,” he said in a low voice as well “let’s take our shorts off and jack each other off. I’ll take yours off and you take mine off, then we’ll do it.”
“How do you want to do that?” I said.
“Well I’ll swim under water up to you and pull them down to your feet, then I’ll tap your leg that I want you to lift up to take the shorts off. Once I get them off, I’ll come up, hand them to you then you do the same with me. Then we’ll jack each other off.”
“Alright, I’ll try it.” I said nervously, “But if I don’t want it done anymore, will you stop right then? This is my first time doing anything like this and I’m not sure how I’m going to like it.”
“Of course I’ll stop if you don’t want to do it anymore, you’re my best friend Jimbo and I don’t want to ruin our friendship just because I’m horney.” he said, “I mean it dude!”
“Thanks, man.” I said.
“You ready?” Zach asked.
“As ready as I’ll ever be!” I said, with a huge grin on my face.
Zach takes a big breath and disappears under the water, soon I feel his hands feeling for my drawstrings of my shorts. In like 10 seconds he unties them, loosens them, and has them around my feet tapping each leg and having me step out of them. He was right, it did feel good being naked in the water, matter of fact I was getting boned up again. Before he came up to the surface though, he did something that caught me totally off guard, he started sucking my dick! I had heard other guys talking about girls sucking their dicks and had seen two boys at scout camp do it in our tent when they thought I was sleeping, but never in my wildest dreams would I think that I would get my dick sucked by a girl let alone a guy but hey it sure felt great! I still to this day don’t know how I managed to keep from moaning LOUDLY and definatly drawing attention from the houses nearby, but I did. OH MY GOD!!! It blew my fucking mind!!! I stood there with my eyes and mouth open and my tilted back a little trying to take in this great feeling. He only does it a few times,(because he has to come up for air sometime)and when he surfaces he takes one look at me, grins, and says “So I see you liked that huh!”
“Dude!” I say, breathing hard and between breaths “That…was…fucking…GREAT!!! Where the…HELL..did you learn…THAT from??!!
“I kept hearing about dick-sucking in school from other guys and how they would get them from not only girls, but other guys as well and I always was wondering what that would be like to do. I never was brave enough to ask for fear of getting beaten-up, so I thought I have the chance to try it for a moment now and see if I like it.”
“I know I SURE DID!!!” I said, my breathing finally returning to normal, “Did you like it?”
“Not bad, might try it again if you want too.” he said.
“HELL YES, you can do it as much as you want!” I said, now that I liked it, I wanted more!! “But now it’s your turn.”
“You don’t have to suck my dick if you don’t want to.” he said, “I’ll be fine with you taking my shorts off and jacking me off.”
I don’t say anything, just grin, take a deep breath, and go under the water. I find Zach pretty easily and start untying his drawstrings. His shorts are more loose fitting than mine were and started sliding down as soon as the drawstring was untied. I quickly slid his shorts down to his feet and started tapping his legs to get his feet out of them. I started to surface and seeing his dick in front of my face, I decided to return the favor, trying to mimic what he did to me. I could only do it 4 times because I couldn’t hold my breath as long as Zach, and surfaced.
“Wow, dude I see you did it too!” he said with a huge grin, “Did you like it as well?”
“Yeah!” I said, handing him his shorts under the water, “I thought it was going to be kinda gross but it wasn’t. Sorry I couldn’t go down on you as many times as you did on me, belive me I wanted to, but I couldn’t hold my breath as long as you can.”
“No problem, hey at least you tried it and found out you liked it right?!” he said.
“Yup! Now let’s get jackin, I want to see if this feels as good.”
We jacked-off for a while and both enjoyed it but not as much as the sucking.
“Hey, let me try something.” Zach said as he stopped jacking me.
“What?” I asked.
“I don’t know what this is called but I saw a couple of boys our age do this in the swimmimg pool showers and wanted to try it.” he said, as he pressed his dick against mine and started humping me.
“Dude, you’re humping me!” I said.
“No, I heard that when guys hump each other they stick their dicks up each other’s asses.” he said, speeding up a little, “This is called something different.”
Just then he misjudged a thrust, and instead of rubbing against my dick with his, it went past my balls and brushed against my asshole. I nearly jumped out of my skin with fright thinking it was going up my ass.
“Damn, sorry dude!” Zach said, stopping quickly to make sure that it didn’t happen, “I didn’t mean for that to happen.”
“No problem, I’m glad to see you stopped before that happened.” I said, the relieved look in my eyes apparent. Just then as luck would have it a car stopped, parked, and three guys who looked to be seniors from the high school got out to swim. We quickly put our shorts back on and roughhoused a little more. About a half-hour later they got out, dried off and left. Realizing we were alone again ment that we could have some more fun.
“Hey, do you want to fool around again?” Zach asked.
“Yeah, but I want to get out of the water and to our spot on shore.” I said nervously, “That was a little close for me when that car showed up. At least when we’re in our spot, if a car parks and people get out to swim, all we have to do is make sure we don’t make any noise to be heard by them. If they happen to start to head over here, we will hear them in plenty of time to get mostly dressed and tell them that there are people changing and not go any furtur.”
“True!” Zach said, “Besides I want to try some more sucking!”
“Yup, and we won’t have to hold our breaths under water to do it!” I said, “You read my mind.”
So we got out of the water, put our t-shirts, socks, and shoes back on, and started to walk over to our changing spot, when Zach goes back, grabs something out of his bag on his bicycle, and comes back.
“Dude, what did you get?” I asked.
“Something that might be needed.” he said, with a wink.
We get over to our changing spot and set our dry shorts and underwear down. We both lay our towels on the ground which makes a nice-sized area to lay down.
“Lay down, dude!” Zach says, as he kneels down on the towels. After I lay down on my back, he starts untying my drawstrings and loosens my shorts.
“Ready?” he asks.
I nod yes, then lay all the way back looking up at the leaves on the trees above me. Zach starts pulling my shorts down and I can feel the cool air on my skin as my wet shorts get yanked down more and more, first my butt, then my dick and balls then my upper legs until I feel him stop pulling when they are at my knees. I have a full raging 6″ hard-on now begging for relief, and then I feel him start to lick my balls gently, (I was glad nobody was there at that moment because I yelped a little and I’m pretty sure had someone been there they would’ve known what we were up to.) and then he starts going down on my dick only I know he doesn’t have to hold his breath under water now, so this could last for a while if I made it. I kept looking straight up at the trees, and after a little bit Zach noticed.
“Dude, what’s wrong?” he asked.
“Nothing at all, you’re doing great” I said looking at him and my now wet dick in his hand, “I’m just afraid that if I watch you suck me off that I’ll shoot too quick and I want it to last as long as it can, that’s why I’m looking up at the trees.
“Oh, ok!” he said relieved and went back to sucking me. I suprised myself when I had him stop and had him lay down.
“My turn now!” I said, sitting up, my shorts still at my knees.
“But you didn’t even shoot yet?” he said, suprised.
“I don’t want to yet!” I said, gently pushing him down.
He shrugged his shoulders and laid down on his back, but kept his knees bent up.
“Dude, put your legs down so I can get your shorts down.” I said, trying to push his legs down.
“No, it’s easier to take my shorts down like this.” he said, “Besides I want my shorts to my ankles, makes it easier to suck me because I can spread my legs for you to get in there.”
“Ok.” I said as I untied his drawstrings, and pulled the baggy shorts down to his ankles. His 6 1/2″ dick looked more monsterous this close up, and as I jacked it a few times it even seemed like it was thicker too.
“Man, that feels good!” he half-wispered, as I jacked him.
I started playing with his balls, noticing how much hair he was starting to get even below his balls and into his crack just a few but they were there.
“Dude, you have hair in your asscrack too?” I asked.
“Yup, have a look for yourself.” he said, as he spread his legs open as wide as his shorts let him go.
I couldn’t help myself as I not only looked, but felt down there too.
“Stick your finger up there while you suck me, I want too see what that feels like.” Zach said, “The lake water cleaned us off so there isn’t anything gross there now.”
So I did and he gasped but reassured me that he was ok and to keep going, I could only get about 3/4 the way down his dick, but it was amazing. I had only did it 7 times when he has me stop.
“Dude I am going to shoot too quick if I have you keep that up.” he says, his breathing becoming rapid “How about we rub our dicks together like we did before that car showed up.”
“No problem, I’m game!” I said, scooting up so I had my dick on his. It made it easier for me to get a better position than in the lake, and as lined my dick up with his, put my hands on either side of him (looking like I was going to do a push up) and started moving our dicks together, it even felt better too. If someone would’ve seen us right then they would swear that it looked like we were fucking, Zach’s shorts around his ankles, mine around my knees, me on a push-up position between Zach’s legs and my butt going back and forth over his crotch area. But not then.
“Hey dude, stop for a minute, I want to ask you something.” he says, as he reaches for his dry shorts and into the front pocket pulling out a small travel-size hand lotion and shows it to me.
“So that’s what you went back to your bicycle and got before we came back here huh?” I asked, my naked dick and balls still pressed against his.
“Yup, and the question I wanted to ask is..” he said blushing a little, “..would you like to take both our shorts completely off spread this on your dick and my asshole and fuck the shit out of me?”
“Do I have to let you fuck me in return?” I asked.
“Not unless you want to.” he said, opening the lotion cap and setting it aside.
“I can try it if you go gentle, like I said it’s the first time I ever did anything like this.” I said, my voice trembling slightly.
“As slow or as fast as you want to go, it’ll be up to you.” he said.
“Ok!” I said, “I get to go first right?”
“Duh, that’s why I asked if you would take our shorts completely off, put this lotion on your dick and my asshole, and fuck the shit out of me.” he said jokingly.
With that said I got up off of Zach, pulled his shorts off over his shoes and I stood up letting my shorts fall to my shoes and stepping out of them, returning us to the state of undress we were in when we were back here just a few hours ago, t-shirts, shoes, and socks only. Kneeling between Zach’s legs I squeezed some lotion out onto my middle finger and smeered it around his asshole, and putting some more lotion on my middle finger, I worked it into his hole.
“Fucking you with the bird!” I told him jokingly.
He responded by grinning from ear to ear. I could tell that he wasn’t in any pain when I did that, but when I smeered my dick up with it and started slowly pushing in, that all changed.
“Oh my god!” he started shouting, “shit, Shit SHIT!!”
Then he realized he was making a LOT of noise, so he put his arm over his mouth and continued to moan loudly, but now he knew it wouldn’t attract attention. Poor guy, I asked him several times if he wanted me to stop but he just kept shaking his head no, and the last time he shouted NO DON’T STOP!!! (thank GOD no one heard that outburst) Finally after about 3 full minutes he stopped moaning loud and was still moaning a little but low enough that he took his arm away from his mouth.
“Ugh!” he grunted through clentched teeth, eyes tightly shut, “Feels like I’m getting fucked with a baseball bat! God what was I thinking, this fucking hurts so bad. you almost there?” he asks, with pleading eyes.
“Almost but I can stop if you want. I can see it’s hurting bad.” I tell him.
“Nope I wanted it, it’s starting to subside anyway.” he says.
About 2 minutes later I tell him I’m about to shoot.
“Do it inside of me!” he demands “Don’t you dare take it out until you have shot every last drop!”
“Oh shit!” I wisper, and shoot the biggest load ever in my life. Finally spent I collapse on the towels trying to catch my breath which I manage to do 10 minutes later.
“Oh my god!” I say, “That was fantastic!”
“I know!” Zach says “It felt like I was getting fucked by a baseball bat there for a while, but at the end it was starting to ease up a bit. But I guess it’s your turn now huh?”
“Yup.” I said “Just remember to take it easy, I was easy with you.”
“I know, and I will.” he says as I lay on my back.
Zach starts smeering lotion on his dick as I get a good comfortable position on the towels, and after I get one he starts smeering lotion in and around my asshole getting it ready just like I did him.
“Ok dude, here it comes! he says and levels his dick with my asshole.
He starts slowly pushing in and now I KNOW what he was going through! PAIN CITY!!! I clamped both of my hands over my mouth as I screamed like I never screamed before, thank GOD I muffled it or the cops would’ve shown up there for sure. I fought my body to get as much in as I could of his dick and finally after struggling for a half-hour, Zach was able to start fucking me.
“Ow-ow-ow!” or “Shit-shit-shit!” was all I could wisper for the next 10 minutes as I was fucked in the asshole by my best friend. Thank god those high school guys we saw fishing when we first got here, or in the car later had left and didn’t walk-in on us fucking, they might have wanted to join in maybe, but I don’t think my asshole could’ve taken anything else then what it was getting now.
“Oh shit dude, I’m gonna shoot! Zach says moments before I feel a flood of cum fill my asshole.
“Man, that was great!! he says, as he pulls out “Did I hurt you dude?”
“Probably as much as I hurt you earlier!” I said, “But what do you expect for the first time? I knew it would hurt a lot, just didn’t expect that much!”
“Yeah, I hear ya’ there!” he says, “A LOT of pain! But now we know what to expect you want to try it again before we leave?”
“Sure, I guess I’m a glutton for punishment!” I said “But this time lets not hold back, fuck as hard and fast as we want! I know there were times I wanted to go faster with your asshole, and I know you wanted to go faster with my asshole too. But we wanted to see how much each of us could take before we did that.”
“I agree!” Zach said “Let’s do it!!”
“Ok.” I said, “But let’s our t-shirts off and tie them around each others mouths so that way the one doing the fucking can grunt and moan all he wants, and the one getting fucked up the asshole can scream and shout all he wants and both will be muffled so as not to draw attention over here.”
“Sounds like a plan to me!” Zach says, pulling off his t-shirt as I pull off mine.
We ball an area of the t-shirts up, stuff it in our mouths, and tie the ends behind our heads making nice muting gags. Zach goes first again as I lube him up and lay down behind him pulling one leg up and entering him from behind and loving it so much that I am slamming it home so hard and fast he is screaming quite loudly and has tears coming out of his eyes, while I am moaning over the best fucking feeling of my life. 15 minutes later, I am shooting another HUGE load into his asshole.
After 5 minutes of rest, Zach motions for me to stand up after lubing me up for my turn. I never knew how strong he was until this moment. He motioned for me to lock my arms around his neck, then he picked me up off the ground under my ass and speared me on his dick! He was moaning at the pleasure he was getting while I was getting it so hard that I actually was crying, bawling was more like it, I was never so glad in my life when he finally shot his load into me and pulled out. But as the rest of that year and the rest of high school went by it kept getting easier and easier for us to do, so we no longer needed gags, even though Zach’s dick grew to 8″ and mine a whopping 9″ by the time of summer 1992.
Now, 20 years later I still go by that lake and “our spot”, yes it’s still there and wonder how many other boys like us got their start there in that spot.
And even though Zach died in the World Trade Center disaster in 2001, I find my mind wandering back to this moment from time to time. Funny how certain events keep memories of friends alive!

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