Date: Sun, 28 May 2023 20:25:50 +0000 (UTC) From: "wantstrat63@yahoo.com" Subject: Messing Around Buddy Training - Chapter 21 Messing-Around Buddy Training - Chapter Twenty One Disclaimer: This story is a work of fiction which features sexual activity between pre-teen boys and teenage boys. If you do not want to read such a story, or it is illegal for you to do so because of your age or where you live, I'd recommend that you bail out right here. I'd love to hear from readers and I'll try to write back. My name is Zane. If you want to get in touch, please email me at wantstrat63@yahoo.com If you are enjoying this series, I invite you to read my other works that have been published in Nifty. For an easy way to find those stories, go to the Nifty home page and type WANTSTRAT into the search bar. If you can, please support Nifty with a financial donation - whatever you can afford - so that this archive of stories can remain free and available. Just go to http://donate.nifty.org/ +++++++ "You just stick it up inside the asshole and it feels like you're fucking a girl." The words actually sounded weird when he said it. I considered Jon's proposition once again and just couldn't get past the asshole equals shit thing. He'd been trying to talk me into it for the past few messing around sessions we'd had together. I'd been doing stuff with Jon for a couple of years at that point. I'd also been meeting with another boy, Adam up in the treehouse on a regular basis as well. We'd look at titty magazines, then traded handjobs and blowjobs. Sometimes, it was just me sucking him off. His hairless little boner had matured from a three inch weenie to six inches, with a nice triangle of pube hairs. Adam would hold my head and fuck my face until he ejaculated his load of jit inside my mouth. The expectation was that I'd feed on what he gave me, and I did. I'd even felt up a couple of scout buddies in the dark on camping trips. I'd lay up against them and touch my hand on their bulge to see if they'd get hard and if they did, I'd slip my hand down inside their white briefs and play with the dick. Then I'd take it out and jerk the guy off or blow him in the dark, quiet privacy of our pup tent. I'd done all those things over the past couple of years, but Jon's prodding to try ass fucking still seemed gross. Before he'd first talked about it, I'd had no idea that it could be done to a boy. We were alone at my house on this day, both naked and doing boner play on my bed when he brought it up again. Jon turned over on his belly, reached back and spread open his butt cheeks at me. "Look Zane. See, it'll go right in and it'll feel great." He relaxed open his anus to prove his point. I looked in his winking little hole and it seemed so red and tender inside. I just didn't know. "You can do me first, buddy. C'mon, it will feel just like you're fucking a girl." This was decades before the internet and I had no point of reference for this bizarre act that Jon was proposing. All I'd seen were Titty mags, National Geographic naked native pictorials and the boy's underwear section of the Sears catalog. There was no mention anywhere about guys fucking each other's assholes. I only had Jon's word that this was a thing, and his hairless little starfish anus, winking up at me. "I dunno, Jon. What if there's shit." The needs of my erect penis were beginning to cloud my mind, weakening my resolve in the matter. I was starting to consider it. "C'mon man, I took my morning dump already and got a shower. All you need to do it stick it inside and you'll know what do to then. You get to go first! Don't ya want to feel what it's like to fuck a girl? I'll be face-down so you won't even see my junk and you can... y'know, pretend." "Pretend what?" I was such a pea brain, even at the mature, worldly age of 13. "Dumb-ass! Pretend like you're putting to Valerie, be both know that you've got the hots for her." Jon arched his back a bit, thrusting his butt up to me. He spread his ass cheeks wider, making his hole seem to open up a bit. It was silently beckoning to me. "I don't have the hots for Valerie, you dumb-ass... I just think she's cute." I looked at Jon's winking butt hole and slowly stroked my 5 inch boner. It was so hard and had that urgent feeling. "Do it then! Spit on my hole and rub some spit on your dick. Go slow when you're putting it in... I'll tell you when you're good to go and start fucking." How in the hell did he know this stuff? That thought popped up in my mind once again, but I never got up the nerve to ask Jon anything about how he knew about all the acts messing-around guys did together. I cast aside my squeamishness and bent down over Jon's butt, then spit right on his hole. It winked shut for a second when he felt my spit, then relaxed back open. The interior of his most secret opening looked so slick and inviting. I could see his muscles inside, making the soft, slick tissues of his anal wall move and flex. This was so weird. My mind was conflicted, I was so horny. There was that ringing in my ears. I checked and didn't see a turd inside. I hawked up some more spit in my hand and smeared it over the acorn-tip of my boner. I straddled myself over the back of Jon's legs and held my dick up close to his hole. This seemed so dirty and wrong. "C'mon, you gonna do it or what?" Something about Jon's tone gave me the resolve I needed and it was almost like I wanted to penetrate him to teach him a lesson. I pressed my cock against his hole and started to push. It was a struggle. He grunted. I grunted. I held my boner so it wouldn't bend and pushed. Nothing. Jon was breathing heavily, trying to relax himself so I could penetrate his boy-hole. That little opening just wasn't having it. It couldn't even accommodate my average sized teenage stiffy. We struggled together for a couple of minutes. I spit some more. He reached back and spread his ass open for me. Nothing. It just wouldn't go in! "Okay you had your chance, now get down here and let me show you how to get it in." Jon's instructions were more of an order than a request, but I complied. I lay face down on the bed and reached back to spread my butt cheeks open, just like he'd done. Jon spit on my hole, and I quickly felt the pressure of his boner pushing against me. We were both struggling, just like when I had tried to mount him. I suppose we weren't really ready to give our youthful bodies up to anal sex. Those teenaged holes were really tight. I was afraid of shit, and all we had for lube was spit. We were both sweating. I had no more spit because my mouth was dry and I only had half a hard-on now. Jon continued to struggle to push inside me, but it was a losing battle. For some reason, it started to seem really funny. I was giggling while he struggled, thinking about how stupid this must look. Finally Jon laughed too. It was so goofy. We weren't ready for it. Maybe it was because it was the last step of admitting to ourselves about our sexuality. Or maybe we just needed lube, but for whatever the reason, teenage anal sex was a fail for us. We ended up laughing and wrestling on my bed. I rolled onto my back and Jon got on top of me, facing me. We were both erect with our dicks pressed together, squished between our bellies. Jon looked down at me and started to hump. I responded by thrusting back up at him. We ground our dicks together like that for quite a while, until we were sweaty and sliding around on each other. I had my arms around him and was hugging him as he humped against me. Jon put his face down beside mine as he thrusted away at me. We nuzzled cheek to cheek while doing our mock boy-fuck. I liked that. We were almost kissing. I'd wondered what it would be like to kiss a boy. I thought about kissing Jon, but I remembered his unwritten rule that if you made out with a guy, that meant you were homo. Yeah, I know, we'd just been trying to fuck each other up the ass and for some reason that was acceptable, but that was the rule. Who was I to argue? That moment would be the closest I ever got to kiss a boy until I was away at college. We ground away at each other until it got really intense and mutually urgent and just about at the same moment we both climaxed. We lay there, breathless. I could feel our combined loads of jit that had squirted between our bellies, making it slippery between us. It ran down my sides as we lay there in our tight embrace, catching our breath. We stayed like that for as long as we could before the feeling that it was homo started to creep in. Finally, Jon lifted off me and our slick bellies and boy-dicks peeled apart. It took several tissues from the box on my nightstand to mop up the evidence. When we got dressed and went outside to do regular stuff that afternoon, it took some strenuous racing on our bikes around the development to get the feeling of weirdness to wear off. I think it even had an effect on Jon that day. But the guy was relentless. Little did I know, he was already working out a plan so that the next time we tried to go at it, things would go much smoother.