By Earth-boy
Quick disclaimers:
- This story contains descriptions of sex between teen and pre-teen males. Do not read if you’re under 18 or it is illegal where you’re living.
- Copyright by the author. Do not upload to pay-to-view sites.
- This story is fiction; references to individuals are coincidental.
- No children or teenagers were harmed in the creation of this story.
I lay naked on my bed in the darkness of my room, resting from another successful round of self-pleasure, imagining more of it with Rhett. Clean-up was simple; I’d started hiding a roll of paper towels in my closet and used a couple for every session. Rather than spilling my seed all over myself, I came into the towel instead. It also gave me greater freedom. No longer did I have to masturbate solely on my back; I could do it lying on my side, on my knees on my bed, or on my knees beside the bed, pretending my mattress was Rhett. Even if it wasn’t as warm as soft.
Tonight I added something else. I still had the other half of the oil I’d used for Rhett’s massage. I put a little on my anus and some more on a couple of fingers, then carefully slid them in part way. Now I spread them apart, stretching out my rear to form an “O”. I knew Rhett would soon want to try going there and I wanted to be ready for him.
Something else had changed as well. Last month I’d been reluctant to go nude with Rhett. Now I was frustrated at being able to do it for only a fleeting ninety minutes each week. I yearned for a repeat of New Year’s Eve where we’d been able to relish each other’s bodies for a whole evening and night. Attempting to recapture that night I started sleeping naked. I felt a little better for it, but of course without Rhett it wasn’t the same. Sometimes I fantasized about me and Mom showing up at his place to find him already undressed, and him pulling down my pants even before our moms had left. In the back of my adolescent mind I imagined Mom freaking out while Sabrina angled to get a better view.
On the first Wednesday in February my phone’s camera got more use. I was curious to see what we looked like playing around naked, so as soon as we got to the basement I told Rhett to keep his clothes on while I set up the phone to record a movie. We first took off our shirts and then the rest of our clothes, Rhett let out his characteristic “RAWR!” and I got a few minutes of us wrassling. Unfortunately this first time both of us were a little too aware of being recorded: I got half hard, and Rhett (being Rhett) mugged for the camera by going right up to the phone, poking his penis at it, and pulling his bum cheeks apart to show his anus.
I also hadn’t realized how much light a good video recording needs. Overall most of what I got looked like shadows. I made a note to do a repeat recording next week and probably the following one as well, when I could improve the lighting and we’d be more used to it.
This week’s debauchery (more properly referred to as “sexual education lab work”) was sixty-nining. I went under with Rhett over me. We’d done almost the same thing the week before, but this time I just concentrated on giving him a good blow job with a little bit of anal tickling. Rhett of course couldn’t take all of my erection in his mouth, and I wasn’t about to teach him deep throating. If he figured it out for himself, so much the better, but for me that was just too advanced for him.
Imitating me, Rhett was playing a little with my testicles and a lot with my anus.
“You’re doing really good, little buddy!” I gasped as he he went up and down on me and tickled my rear with a couple of fingers.
“Mm-mph!” was his articulate reply. He carried on. I started to marvel at his tenacity; he was spending a lot of time on this.
“If you’re getting tired,” I told him, “just start using your hands. Your mouth is fantastic, though!”
Suddenly he pulled off. “Just tell me when you’re about to shoot. That stuff’s gross and I don’t want any of it in my mouth!”
“Hmm,” I responded. “I just might decide to give you a little surprise.”
“Seriously, don’t!” he retorted. “You shoot in my mouth and I’ll crap on your face!”
“You would?”
“Do you wanna find out?” he shot back. “No way I’m taking your sperm!” Then he went down on me again.
Damn that felt great. I used my mouth and tongue on his much smaller penis, hoping I was doing as good for him as he was doing for me. Then Rhett put his hand at the base of my penis and started working from there up as far as his mouth came down. Suddenly I felt the oncoming rush. Briefly I wondered if I should bypass warning him, but thought the better of it.
“Pull off! Pull off!” I cried out. “I’m gonna cum!”
He did, fortunately with a few seconds to spare. His hand went straight to working on my head, and soon he had a small geyser erupting all over. The big shots hit me, while the little ones ended up all over his hand.
“Yuck!” he said, with noticeable disgust in his voice. “Gimme a paper towel; I gotta get this stuff off me.”
I handed one to him, and continued sucking him while he wiped off his hand. Then he said, “You can stop now. I haven’t had an orgasm, but after getting your stuff all over me don’t think I’ll be able to.”
I let go of his penis, and he moved to sitting beside me.
“You really don’t like that stuff, do you?” I asked.
“No!” He practically shuddered. “It’s slimy. It’s okay when it goes on my tummy, but it just felt icky on my hand!”
“If it’s any consolation, it’s not supposed to end up on either. Tell you what—from now on let’s make sure it can’t end up on your hands or in your mouth. Uh, you okay with not having an orgasm?”
“Sort of. It’d be nicer if I had.”
“I’ll try giving you one in the bath.”
“All right!”
I ran a bath for him and as always we got in together. One change from my first visit back in December was the bath toys were no longer in use. Rhett didn’t need an excuse any more to enjoy an nice long bath; I was all the reason he needed. We usually passed the time appropriately splashing and inappropriately touching each other, telling silly jokes, farting in the water, wagging our bums at each other, and generally just goofing off. It was great fun for both of us. More than at any other time Rhett got to be just a little kid. I loved it too, being able to abandon my role as a babysitter for half an hour and going back a few years when being a kid was fun.
When it came time to doing the actual washing up part, I did as I promised earlier by masturbating him with a finger in his rear, stroking his prostate. I took a bit longer than normal, but eventually Rhett sounded an “Ooohhh!” as he had a dry cum. We were both happier for it.
We finished off the rest of the evening as we always did.
Rhett celebrated his tenth birthday in February. I saw him again on the second and third Wednesdays of February, the third one being the day after his birthday. As I’d done for the past couple weeks prior, I set up my phone to do some video recording. Using lessons learned from the previous two sessions, I turned on as many lights in the basement as I could find, and even produced a lamp of my own from my backpack for additional lighting.
The wrassling bout was brief, though, because I had a full agenda planned for the evening and we didn’t have a lot of time. With my phone still recording, I sat us down closer to it and pull two gift-wrapped boxes from my backpack.
“Happy tenth birthday, Rhett!”
His eyes lit up when he saw my gifts. “Oh, thanks!” Eagerly he tore them open. The larger package contained several more sections of track and two railroad switches. But the smaller one had the better gift: a model steam locomotive for running on the track.
“Neat!” exclaimed Rhett as he tore off the wrapper. “Thanks, Chad!”
“You’re welcome, little buddy! Do you want to try the engine now? I’d like to make sure it actually works, because I don’t have anything at home to test it with.”
Wary of Rhett simply tearing open the box, I carefully opened it up, extracted the locomotive, and handed it to him. He immediately took it over to the track. I followed him with my phone, capturing a nice view of his butt. He put the engine on the track and gave it a spin. It worked perfectly and Rhett exclaimed, “Yay!”
I stopped recording and saved the file to the phone. After turning off the unneeded lights, we sat down on the basement couch to review the video. This one was by far the most successful; with the added light it came out crystal clear. Both of us were now used to our little wrestling matches being recorded and it showed. We simply went at it without worrying about the camera, and I had a nice candid video of two naked boys roughhousing in a basement.
“Can I get a copy of that?” Rhett asked when we’d finished watching.
“Uh, well, not right now,” I replied. “I forgot to bring a USB cable to transfer it with. I’ll see if I can remember one the next time.” Of course, by then the video would be hidden away on my computer and deleted from the phone.
The USB cable excuse was only partly true; a search in their house would likely have turned up a suitable one. The real reason was I hadn’t yet found a way to hide or encrypt the file and didn’t want Sabrina stumbling on it. While I doubted she’d have any problems with the content, I’d be really embarrassed to know she’d seen me naked. I also knew things could get complicated if they ever sent their computer out for repair and the shop saw the video. I was only fourteen, but even at that age I’d read stories about that sort of thing and didn’t want it happening to me.
“Oh, I just remembered!” Rhett suddenly exclaimed. “Mom saved some of my birthday cake for you! Do you want to eat it now or take it home?”
“Hey, thanks! I’ll have it now. And if there’s enough I’ll let you have a small piece, too, even if your mom says you shouldn’t.”
We brought our clothes upstairs with us. Sabrina had thoughtfully set my piece aside on a plate in the fridge. I found the rest of what remained of the cake and cut another piece for Rhett.
Of course Rhett had to smear some icing on his bare chest. That gave me an idea, and I took a bit of the icing from my own slice and spread it over my foreskin. Rhett giggled and did the same. Quickly we finished up our slices, then ran to the bedroom where we spent an enjoyable couple of minutes licking each other clean.
“Now,” I announced, “I have another present for you.”
I got out the oil I’d used previously for his massage. First I applied it to some of my fingers, then easily stroked him to an erection and slicked up his penis.
“All right, little buddy. Tonight’s the big night! It’s the graduation ceremony for your private Chad-tutored Sexual Education course! On the program: insert penis R into anus C and have the best orgasm of your life.”
I applied some oil to my rear, got on my knees on the bed, and bent over. As I’d practised for last two weeks, I slid a finger from each hand into my anus to the first knuckle and easily stretched it open.
Rhett’s eyes widened when he realized what I was offering. “Oh, wow!” he cried, and in an instant was behind me. A moment later I felt his penis slide along my fingers and enter me. I removed my fingers and my anus closed around it.
He needed no further instruction and began sliding his boy penis back and forth inside me. A couple of times he misjudged and pulled out completely, but it took only seconds for me to open up and he was in again.
I wasn’t sure what Rhett was feeling, but for me it was so much better than I’d expected! I was afraid with his small penis (erect it was barely three inches [7.5 cm] long) I wouldn’t be able to feel it at all inside me. Boy was I wrong! Erect, he was similar in size to my index finger, and the sensations were the same.
Quickly Rhett got into a steady rhythm, pulling out almost all the way and going back in. Soon he was going faster and I could hear some moans from him. And me, too. He was actually hitting my prostate! I hadn’t planned on this—the point of this exercise was to give him an orgasm, and I’d take care of my own later. But sheer novelty of having Rhett do me from behind, feeling his small hard member sliding in and out inside of me, and hearing his thighs slap my butt every time he bottomed out was turning me on big time.
And I’d neglected to get paper towels from the kitchen.
He was really getting into it now. He paused momentarily add more mineral oil where we came together, then picked up again with renewed enthusiasm. Now he was going to town on me, seemingly trying to hump me as fast as he possibly could. His breathing deepened and quickened, as much from physical exertion as from the sex itself.
Slap! Slap! Slap! With every thrust my rear felt incredibly full with Rhett’s penis filling it and withdrawing. A familiar sensation started rising in my groin. In an attempt to avoid coming all over his bed I completely let go of my own penis and put both my elbows on the blanket.
“Just! a! little! bit! more!” I heard Rhett gasp as he continued driving into me. He was almost at a frenzy now, pulling out just a little before slamming back in. Then … “Ah! Aaahh! Ah—ah—aahh—errrrgggghhhh!” as his orgasm grabbed hold and consumed him.
I came too. With no other stimulation than Rhett in my rear, my penis spasmed and I shot hard three times all over the blanket, followed by several smaller ones. Gasping for air, Rhett collapsed on my back and his penis unceremoniously popped out of my rear.
It must have taken him two full minutes to recover, all the while an almost motionless dead weight on my back, save for his breathing. Finally he rolled off me and flopped down on his back beside me. Both of us were at a complete loss for words; he simply gazed straight into my eyes while I gazed back at him.
Finally I spoke. “Did you like it?” I asked quietly.
He smiled. Not a grin, but a wide smile of complete satisfaction. “Oh yeah, did I ever! It was, like, as you said, the best one so far! So, did I pass?”
It was my turn to smile back at him. “That was the graduation, not the final exam. But if it was, you would have scored 110%.”
“That good, eh?”
“Absolutely that good! But now we have a bit of a cleanup. I came all over your bed.”
“Gross! You get to clean it up; I’m not touchin’ it!”
Of course I did so, using a couple of wet paper towels and two more dry ones, which I again carefully disposed of at the bottom of the garbage bag under the kitchen sink.
As I was running the bath, Rhett asked, “So are you gonna do me next week?”
“Uh, you’re talking about what we did tonight?”
“Yeah, except this time it’s you in me.”
I looked him straight in the eyes. “Rhett, right now the answer is ‘no.’ It took me a week to stretch myself out back there to accept your penis. Mine’s a lot bigger, and you’re smaller. If I tried to do you, the pain would be incredible. I mean, it would probably be so bad you’d throw up. You’d feel it for days afterwards. And your mom would notice and ask you what’s wrong. There’s no way I want her to find out we’ve been having sex!”
“She probably wouldn’t care that much.”
“I don’t want to take that risk. Yes, best case is she’s just cool with it. Worst case is she totally freaks out and says we can never ever see each other again. And you go back to having girl babysitters. Do you want that?”
“No way!” he cried. “You’re the best babysitter I’ve ever had and I don’t wanna lose you.”
“I know that. Now, your mom knows we take baths together and she’s all right with that, but she probably doesn’t know about all the other stuff, like us being naked practically the whole time I’m here. And if you want to keep seeing me and having fun with me, then please keep quiet about it. Like I’ve said before, just tell your mom we wrestle around a bit in the basement and play video games. She doesn’t need to know about everything else.”
“So, when are you going to do me?”
I’d actually thought about this before, knowing at some point Rhett would want me to. I gave him the answer I’d already decided on.
“Not before summer vacation’s over. I’d really prefer to wait until you’re eleven or even twelve, but that’s a long ways off. You’ll probably not need a babysitter any more after you turn eleven, and then we probably won’t see each other very much any more. So … let’s wait until after summer, okay? Do you think you can do that?”
Rhett was clearly disappointed. Summer was four months away, and “after summer” was a whole six. To Rhett that probably looked like half a lifetime. “I wanna do it before.”
I shook my head. “No promises on that one, little buddy. ‘After summer vacation’ is the only one I’ll make, and even then we’ll have a lot of work to do to get you ready.”
“Why can’t we start now?”
With that question he was making more sense that I was. I was the one afraid to take this last step; he seemed to be eager to go ahead as soon as possible.
Once again my resolve crumbled. “Let’s get in the bath,” I said. “We’ve got some stretching exercises to do. And I’m not talking about on Jupiter.”
“What?” asked Rhett, confused.
“Like I said, the stretching exercises aren’t on Jupiter. They’re on Uranus.”
“Bleah!” was his only comment on my bad pun.
Once in the bath, I soaped up a finger in anticipation of starting a long process of getting him to the point where I could enter him. Then I realized I saw him only once a week, while he took a bath every night. It was like the old adage of giving a man a fish versus teaching him how to fish.
“All right, kiddo, if you really want to feel me inside you, you’ve got to get ready for it. First, lay down on your stomach.”
He did so.
“Now, put soap on two of your fingers and run then into your rear. They don’t need to go all the way, only part way. In fact, right now just try one finger. That should be easy, because I’ve put one of my fingers up there and it was all right.”
He tried first with one and had no problems. Then he did two.
“All right, that’s good. Now try spreading your fingers apart while keeping them there.”
“Ow!” I heard him say.
“You see, that’s what I’m taking about. That hurt, and you barely spread your fingers apart. Now think of what my whole penis would feel like!”
“Yikes! Yeah, that would hurt!”
“So here’s your homework. Every bath time for the next week, you put two fingers into your rear and gently stretch your anus just a little bit. I know you well enough to know you’ll want to try a great big stretch right way, but, seriously, don’t do that! Just a little bit every day. Okay, try again and show me what I want you to do.”
He did as I asked, putting in two fingers and spreading them just a little.
“Good. Now, I’m going to repeat what I just told you. Do not try to stretch too far. I don’t want you hurting yourself. Just up to the point where it feels a tiny bit painful, but no more. Now, repeat that back to me.”
He did, and I had him repeat it once more for good measure. We finished off the rest of our bath as usual and I carried him out of the tub as he enjoyed me doing. While drying him off I had him repeat the instructions yet again. I firmly told him to follow them and as best I could, and extracted a promise he would do so.
“And remember,” I added, “this is only stage one. We’ve got at least two weeks of doing this before I’ll even think of doing you, and probably three weeks. Please don’t try to rush it! Promise?”
“I promise.” He sounded sincere, and I really hoped he would follow the instructions I gave him.
After the bath we did our usual naked reading in in bed, got dressed, and I kissed his bum as he liked me to before we kissed each other good-night.
“Uh! Uh! Uh! I’m almost there, Rhett!”
“Oh! Feels good!”
“You’re liking it?”
“Oh yeah! Keep going!”
“Just a little bit more! Oh! Oohh! AAAHHH!”
I shot my semen all over his back.
It was the first week of March, two weeks since I’d taught Rhett how to stretch himself to get ready for me. He wasn’t there yet, so for tonight I had him on his stomach, while I put oil between his bum cheeks and went at with my penis there—an idea I’d picked up from a story on Nifty. Hot-dogging was what they called it, and this was the first time I’d done it. It was a huge rush, having my erection fully surrounded by Rhett’s body.
I used a paper towel to clean him up. He’d already done me, so now it was bath time.
“Let’s see how you’re doing, little buddy,” I told him when we got into the tub. “Show me how far you can stretch.”
Rhett grinned, soaped up his hand, and to my surprise put three fingers into his anus and stretched. Wide.
“Wow!” I said. “That’s impressive!”
“Thanks!” he replied. “Next week I should be able to take you. I’m really looking forward to it!”
“I am too! All right, we need to try something else. Get on your hands and knees and lower yourself so I can see your anus.” He complied. “One finger, coming up. Or rather, going in!”
I soaped up an index finger and put the tip on his anus. “All right, what we’re doing now is a relaxing exercise.” Nifty could be a real educational resource at times. “You’re pretty good, but a lot of times people really tense up the first time someone tries to shove his penis up there. So I want you to do right now clamp your anus as tight as you can.”
I saw it flex, and I tried inserting my finger. It couldn’t make any progress at all.
“Good! Now relax it. Then relax it some more.”
I tried my finger again. This time it went in like a spoon into porridge. I found his little prostrate and rubbed it a couple of times, and was rewarded with a small cry from Rhett. I pulled out again.
“That was great!” I complimented him.
“And it felt neat!” Rhett replied. “I can’t wait to feel your whole cock up there!”
“My ‘what’?” I asked, trying to add a mock sternness to my voice.
“Sorry, I meant dick!”
I gave him a light slap on the bum. “You keep that up, little one, and you’ll be waiting a long time to feel my penis inside you!”
Rhett didn’t say anything; he just looked at me and grinned.
“All right, lesson’s over,” I told him. “You can get comfortable again.” Rhett turned around and sat down it the tub.
I put the tips of my index finger and thumb together to form an ““O”. “See this?” I told him. “This is how big I am when I’m hard. Put three fingers through there.”
He did do, easily.
“Hmm. Try adding your thumb.”
Rhett’s three fingers and thumb nicely filled in the space.
“There you have it,” I told him. “When you can do that to your anus without feeling any pain, we’ll be ready!”
Rhett flipped over in the tub, soaped up a hand, and gave it a try. “Oh!” he cried. “Almost! For sure next week!”
“All right!” I responded. I admit I was looking forward to it as much as he was.
We washed each other, I carried him out of the tub, and like always I dried him off. Then it was off to his bed for some more reading. Thanks to Sabrina making the house warmer for us, since New Year’s there’d been no need to cover our legs and feet to keep them warm; we just sat down naked on the bed, got close, and read. We were making decent progress on The Elves of Forest Green, averaging about fifteen pages a night. I was getting into the story myself. Then we got dressed and I gave Rhett two kisses on his bum, then our usual kiss good-night.
“I’m ready!” was the first thing Rhett said to me the following week once my mom and Sabrina were out of the house. “Three fingers, thumb, and no pain at all! Let’s do it!”
We didn’t even go down to the basement. We headed straight for his bedroom and stripped as fast as we could.
“Let’s start with this!” he told me. He put a hand on my already hard penis and sucked it for a minute. He was really hard. too.
“All right!” he cried. I’d barely said two words beyond greeting him at the door. He gave me a big kiss on my lips, then looked me in the eyes and with a funny smile asked, “Chad, can you please insert your penis into my anus and have an orgasm inside me?”
“You’re making a little ceremony out of this,” I said.
“Hey, it’s a special day—the first I’ve ever had someone have real sex with me!”
“It means you’ll no longer be a virgin,” I said. “Well, okay, that usually happens the first time you do it with a girl, so I don’t know if this counts.”
“Who cares? C’mon, let’s get started!”
“How do you want to do it?” I asked.
“What do you mean?”
“Oh!” He didn’t have the advantage of all the porn I’d watched. “You’ve only ever done me when I’m on my hands and knees; that’s called ‘doggy style’ because it’s how dogs do it. Uh, a couple of other ways … on your stomach, or you on your back—”
“That’s it!” he said. “We can watch each other.”
“Yeah! Let’s get something to prop you up a bit. I know—blankets!”
I raced to the linen closet and grabbed three blankets. I threw them on the bed on top of each other.
“Lay down on your back. I’ll get the oil.”
“Way ahead of you!” said Rhett. “I’m ready back there. Here, let’s get your—penis—ready.”
His hand was already greased up; he slicked up my penis. It was so hot I almost came right there. Then he got on his back on the blankets and raised up his legs. “Put it in!” he begged. “Put it in!”
I got on my knees behind him and put my tip right on his anus. “Countdown!” I said. “Let’s start at five! Five …”
He picked up on it right away. Together we said, “Four. Three. Two! One! ZERO! LIFT OFF!”
Gently I thrust my hips forward, just a little. Effortlessly my tip slipped inside him.
“Oh!” Rhett cried.
“Did it hurt?” I asked, concerned.
“Hurt? No way! Hell, that felt neat! Go in already!”
I went in a little deeper. “All right?” I asked.
“More than all right! Go in all the way!”
I did. In one smooth motion I put the rest of my penis into him, and my sparse pubes met his bum. “Oh!” I exclaimed. “That feels—I don’t know how to say it! Amazing!”
“Same here! Chad, we did it! You’re all inside me! Oh man this feels neat!”
I pulled back a bit and in again. And I did it again. Then further back and in once more. “All right there, little buddy?”
“Oh yeah! It’s … it’s wild! Keep going!”
I was as excited as I could ever remember. Three weeks of waiting, and now we were finally doing it! Wanting it to last as long as possible, I started a slow, steady rhythm, going out almost all the way and gently sliding back in. It was amazing feeling his anus clamping my shaft as I went back and forth. Almost without realizing it I started pushing in a bit harder each time. Rhett was going “Mmm! Mmm!” with every thrust. He grasped his own penis and started masturbating.
Every withdrawal caressed my penis, every thrust increased my desire. I was trying hard not to ramrod his rear, fearing it would become too much for him and he’d want me out.
Pull back. “Ah!” Press in. “Oh!” I sped up as lust took hold of me, then slowed down just in time to stop from going over the edge. I paused for a few seconds and carefully started again. The excitement was incredible; the pleasure even more so.
“This one’s for real, Rhett!” I cried as I started going faster. “No way will I be able to hold off this time! Prepare to get creamed!”
“Do it Chad! Cum inside me!”
A few more strokes and I was there. I buried my penis as far inside him as I could while my orgasm sent shock waves all over from my chest to my toes. I pulsed and pumped and flooded his insides; I cried out something but I’ve no idea what. I felt the muscles of his entire rear contract around my penis as his orgasm swept over him and played itself out.
I lowered myself to his body, then with my penis still inside rolled on to my back with him on top of me. I lightly massaged his back and bum while my erection subsided and eventually slipped out. When it did, I hauled him up on me to get his head even with mine and planted my lips on his. We french kissed for a several seconds.
“That’s it,” I said. “We did it! Was it as good as you hoped?”
“Wow! Yeah. That felt so awesome!”
“I’m so glad we didn’t wait until after summer vacation” I said. “I didn’t hurt you, did I?”
“Hurt?” Rhett replied. “No way! Not at all.”
“That’s great! That’s why we spent all that time getting you ready. Otherwise you’d be crying now.”
“I’m so not crying!” He put his lips on mine for another brief round.
“Shall we get a bath?” I asked.
He agreed with enthusiasm.
Comments are welcome at earth-boy-2755@protonmail.com, and constructive criticism as well. As I’ve mentioned before, this story is complete (12 chapters in all.) But as of the date I’ve posted this, I can entertain suggestions as long as they don’t break the established plot or have a serious impact on the remaining chapters.
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