Dear Jason – Chapter 8
It was an intense week at work. Our corporate office charged Fred, and a full-blown investigation was launched. It turned out that I did my job well. Every single piece of evidence pointed to him. I later learned they even used our internal CCTV footage to check if no one else had entered his office. Something Fred obviously claimed.
There was a lot of chaos, and everyone was required to come to the office instead of working from home. I didn’t like it all that much, but it did give me plenty of time to work on my side project. I copied a few lesser-known websites, hosted them on a private server, and adjusted a few things on them. Of course, one could call it fake news, but I didn’t care about that at all. Since I had complete control over James’s computer, this was highly usable for the things I had in mind.
The mandatory working at the office was a bit of a bummer because I lost my direct view of James this way. But I always had his webcam I could use, and I sure got some excellent footage from it.
I replayed one clip the camera recorded over and over again. It was the first clip where I saw James entirely naked for the very first time. He was in his room, obviously, and about to change into his swimming trunks. He was playing some music from what I learned by looking it up, Lil’ Nas X, and dancing to the beat. Then, after he ditched his shirt and shorts, he made some pretty decent dance moves in just his underwear.
But during a short break in the music, he unceremoniously dropped his boxers. He was facing the camera as he did this, and as he stood up straight, I saw him in all his glory for the first time. He wasn’t fat or skinny. He had just the right proportions for a twelve-and-a-half-year-old boy.
His almost three-and-a-half-inch dick was cut and had a very traditional mushroom-shaped head on it. It wasn’t pointy or blunt. It was like how you’d see it in a sex-ed drawing. This boy was as average as they can be, and I fucking loved it!
Thanks to the high-res camera, I could zoom in quite extensively, and I could see he had just a few strands of pubes above his cute-looking dick. His sack was completely hairless, and his relatively big balls filled it out quite nicely.
The music started again, and his dick swayed from left to right as he moved to the beat. James began to giggle at that, exaggerated the swinging, and even did a few full three-sixties. After the music was done, he turned around to grab his swimming shorts, and as I got another good look at his perfect ass, I was completely hooked.
I jerked off multiple times while looking at this gorgeous boy, and the urgency to do more snowballed in my head. But I needed this to be a mutual thing. With Raf and Alec, I more or less forced myself on them. I got away with it, it was awesome, and they probably didn’t feel that way about it, but it didn’t feel right to keep doing it this way.
My first opportunity to plant the seed I planned came Friday evening. I came home from the office feeling tired. But when James walked over, looking a bit sad, I was immediately on full attention.
“Wazzup, champ?” I asked as he approached me.
Something looked off because his whole body language showed he was down. His shoulders were hanging, and he looked at the ground. And it almost looked like he was dragging himself toward me.
“I… uhm… my keyboard is broken,” he said, almost tearing up.
“Oh,” I replied, expecting something much worse.
“Yeah… I was playing Apex, and when I got shot while I was in second place, I lost it, and then I turned my chair, and it accidentally fell to the floor, and then it…” and a tear flowed down his cheek, making my heart melt.
“I see,” was all I could come up with, not trusting my voice completely.
“Mom said I needed to tell you, and I should pay for it myself, and…”
He started crying in front of me for real now, and I hugged him in an attempt to calm him down.
“Don’t worry about it, Champ. I’ve got lots of spare keyboards lying around.”
“You do? But I didn’t see any,” he softly said.
“That’s because they’re in a box in the attic. I don’t need that many keyboards when I’ve got a wireless one, you see?”
“Right!” he said, suddenly smiling brightly.
“And I’ll tell your Mom they break easily, so you’re off the hook there. Tell you what. Why don’t you come over tomorrow morning, bring your computer and we’ll play some games together at my place? You’ll have to teach me how this Apex thing works, okay?”
“Awesome! And thank you!” he said, hugging me tightly.
“Just look under that rock over there,” I said, pointing, “and grab the spare key to let yourself in, okay? Maybe I’m outside or something, and that way, you don’t have to wait with your heavy computer. And I trust you,” I added, smiling warmly.
“Wow! Thanks! I won’t tell anyone where it is. Promise!” he said excitedly.
“See you tomorrow at, let’s say, nine-thirty?” I laughed.
“Great! Bye Jason!”
And with that, he ran back home. I loved feeling him pressed against me. It wasn’t anything sexual. It was just genuinely nice to feel him express his affection for me. And I would’ve loved to have him over tonight, but I already had other plans.
By now, I have learned the schedule of James and his family. Friday evening, they always made a point of eating dinner together. I knew it was a risk, but I wanted to try being inside James’s room for an evening.
As I disrobed in my bedroom, I felt anxious about what I was about to do. I inserted the voice changer in my mouth and pressed the pads together.
As I watched myself disappear in the mirror, I still felt a thrill of excitement shoot through me. I double-checked if the voice changer was invisible, and as I tried it, I was pleased with the results.
I was planning on talking to James later on. But for obvious reasons, I didn’t want him to recognize my voice. So after searching online for a while, I found a small device I could put in the back of my mouth, and it lowered my voice a couple of octaves. It used a microphone and a small speaker to change it. It didn’t sound creepy or scary, but you couldn’t make out my voice anymore. I tried using a different accent and a low voice, but it just didn’t work. This little device did.
As I walked across the street, the anxiety I had felt earlier faded away a little. By now, I felt confident enough to go inside their house and remain unnoticed. And although it still felt a little weird to walk around naked, I was slowly starting to get used to this.
I walked around the back and squeezed myself through the small opening in their gate. I could see the whole family sitting at the dinner table through the window. So far, so good. The back door was open, and I didn’t have to wait long for them to be distracted so I could sneak inside.
“Mr. Whiskers!” Julia exclaimed, “don’t leave that in here!”
I glanced over and saw their cat had dropped a small mouse in their living room and sat proudly beside it. Bill quickly got up, picked up the mouse, and threw it in the trashcan outside. This gave me more than enough opportunity to sneak upstairs.
The moment I got upstairs, I noticed both Julia’s and James’s bedroom doors were open. I never saw Julia’s room from the inside, so I decided to do a quick recon.
It was basically a mirror of James’s room. Even her bed was in the same place as her brother’s. Other than that, it was a typical girl’s room with lots of pink and a few posters of pop stars against the wall. I only recognized Harry Styles, but I figured the others were probably also famous.
Julia was a little sloppier than her brother, though. I noticed a small bra thrown over a chair and a pair of white cotton panties on the floor beneath it. The panties were white with small red dots on them. I resisted the urge to sniff them and quickly went into their bathroom.
They seemed to have made some sort of agreement together because all of the girl’s stuff was on the left side of the bathroom, and the boy’s stuff was clearly on the right. I smiled inwardly at the difference between these twins.
A few moments after I entered James’s room, the door opened, and he came barging in, shouting, “Okay, Mom! I’ll do it after Julia’s done!”
He clicked on his PC that was in the corner of his room, and as it booted, he took off his shirt. Of course, I was used to seeing him topless, but it was still an incredibly lovely sight to look at. Especially when he dropped his shorts and was standing there in his green army-camouflaged boxers. It showed off his magnificent ass perfectly. But I also realized that with an ass looking this good, even a paper bag would do it justice.
He walked over to the window and looked across the street to see if I was home. After he realized I wasn’t there, he shrugged and sat in front of his PC, put his headphones on his head, and started his game.
I was lingering in the corner, waiting for the right moment to start talking to James. He was utterly engrossed in his game, and I could hear some sounds in the hallway. So I just had to wait a little longer.
I almost got a heart attack when the bathroom door suddenly closed. Next, I heard the sounds of it being locked from the inside, and moments later, the shower started. Now that it was clear what was happening, my heartbeat dropped back to normal.
James didn’t move a muscle and was still playing his game, seemingly undisturbed. But when his bedroom door opened and his Mom came in, he looked up from his computer. A second later, his screen turned red, and James mumbled something under his breath.
“What’s wrong?” his mother asked.
“I lost, thanks to you,” he said disappointedly.
“Don’t be silly! Just play another game,” she said as she walked toward the window and looked outside.
“I’m sorry. But I was so close!” James said as he stood up to pick up his clothes and stopped them in the net hanging on the wall.
“Do you want the whole street to see you in your undies?” Ellis asked as she started closing the curtains.
“Only Jason can see me. And seems to me that he’s cool with it. Besides, it’s not like I’m naked,” James said as he sat back down on his chair.
“Guess you’re right. And Jason is a nice guy, indeed. Guess he starts seeing you as his surrogate son,” she chuckled and looked at his screen.
“Yeah. He’s really nice and likes having me over. He even told me where his spare key is. And he’s way cooler than most adults I know,” James said without looking up from his screen.
Ellis giggled softly at that but managed to hide it from her son and asked, “You’re going over there tomorrow?”
“Yeah. He asked me if I could show him how this game works. And he said he needs help with moving some of his furniture.”
“That’s great, honey! I think he likes having some company over after his messy divorce. And the two of you seem to hit it off.”
“Yeah. I like him. And not just because he helps me out with my computer,” James said, and as he looked up from his PC, he smiled warmly at his mother, and I saw a twinkle in his eyes. “Can I have a sleepover with him?”
“Haha! He’s a grown man. I don’t think he’s into sleepovers anymore!”
“But can I ask him? He’s got a really cool setup in his office, and that way, we can play games all night! And it isn’t a school day on Sunday, so…” James said, hyped up all of a sudden.
“Tell you what. You can ask him, but if he says no, don’t push! Okay? And make sure you don’t overstay your welcome because this might push him off,” Ellis said a bit sternly.
“YESS!!” James said and hugged his mother.“ I promise I’ll ask him, and I won’t push. Thanks, Mom!”
“Just have fun! And if you stay the night, you can come and grab some fresh clothes. It’s just across the street, remember?” she chuckled as she nudged him in his side.
“Uhh… it isn’t cool to go out during a sleepover, Mom! And I can put on some fresh underwear the next day. That won’t kill anyone.”
“Well… you do what you do. Just make sure to be nice to Jason. And don’t forget your shower, mister!” she said as she left his room.
James balled his fist and whispered a soft “yes!” before he continued his game.
It was a no-brainer for me to allow James to spend the night when he’d asked me. But after moving my office, I only had one real bed left in my house and one mattress on the floor in another room. So I needed a way to find out if he was okay with sleeping in my bed with me. I didn’t expect him to have a problem with it, but it might look weird if he told his parents about it.
I noticed the shower had turned off and made a note to myself to hide in their bathroom next time to see how Julia looked. James seemed oblivious, but when his bathroom door unlocked and opened a second later, he glanced at the door, and so did I.
Julia walked into her brother’s bedroom wearing nothing but a towel around her hair and an almost too-fluffy and small towel around her torso. She looked smoking hot like this. Her tanned body was still damp, and her long, shapely legs were almost completely visible because the towel was just barely long enough to hide her pussy.
As my eyes roamed up over her body, they paused on her breasts. Almost the entire top half of her boobs was showing, and the towel just managed to cover her nipples. Her lovely shoulders and long neck were still damp, and she smiled as she looked at her brother.
I glanced quickly at James, almost feeling sad for no longer looking at this young girl’s body, and I couldn’t suppress a smile either. His eyes were wide, and his mouth was slightly open. Apparently, this was the first time she had come into his room like this. Or maybe this was the first time he actually noticed. But either way, it hit him hard. And also quite literally.
As my eyes went down to his crotch, I saw a small tent forming. And it kept growing rapidly.
“You’re up,” Julia said sweetly as she walked over toward his brother and looked at his screen.
James cleared his throat and casually placed one of his hands in his lap. “I’ll go in a second,” he croaked.
“Can you ask Jason tomorrow when he’s able to help me with my PC?” Julia asked, seemingly oblivious about how sexy she looked.
“I…” James stammered and cleared his throat again, “yeah. I’ll make sure I’ll ask him.”
“Great. Thanks!” she chirped and turned around to return to her room.
James’s eyes grew even wider as he looked at his sister’s backside. The towel wasn’t long enough to completely cover her back. This meant that more than half of the bottom of her pert ass was showing. I felt myself grow to full mast instantly as I looked at her walking away.
A few seconds later, we heard music coming from her room, and I heard James exhale. He released a soft “damn!” and saw his shoulders relax. This was it! This was my opportunity to put my plan into action.
“That was interesting,” I said while standing a little behind James.
The moment I said this, he almost jumped from his chair. He turned around and started looking around his room frantically. I got a good look at his still-tented boxers as he did this.
“Who… who’s there?” he stammered.
“Relax, James. I’m your inner guide. Or the voice of reason. Some call it conscience,” I said, impressed by how good my voice changer did its work.
“But.. I’m… you…” he stammered, looking directly at me, but looking right through me.
“I’m here to help you get through puberty. I won’t be here all the time, and I’ll only be here for a few months, maybe a year.”
“I… I never heard of such a thing. Or read anything online about it,” he softly said, clearly feeling less scared. His boner was gone now, but his bulge was still prominent, and he looked hot standing there.
“Yeah. I know. But would you post online that you hear voices?”
“Uhh…” he responded thoughtfully.
“That’s what I mean. There are some articles online and why I’m here is still a mystery to science. But hey! Why not make the most of it, right?”
“I guess… What do I call you?” James asked as he sat down.
“Well… Jiminy Cricket is taken,” I chuckled, causing James to giggle too.
“How about John?”
“That’s a bit generic, isn’t it?” I asked, but honestly didn’t care.
“That’s why it’s so good!” James smiled, “John is one of the most common names, so if I call you, it won’t be too obvious, right?”
“Then John it is!”
“But uhh… why are you here now?” he asked as he fiddled with his mouse.
“I don’t know. I guess your hormones are starting to work. And I don’t blame them with a pretty girl like that in your room.”
“She’s my sister!” he said, acting offended.
“I know. But you got hard seeing her. I don’t blame you, but it is what it is.”
“I didn’t want… it wasn’t… she..” James stammered with his face and upper half of his chest turning beat red.
“Don’t sweat it! She’s a girl, she’s hot, and she was practically naked. So it’s only normal to get hard. And just so you know, all your secrets are safe with me. You’re the only one I can talk to.”
James thought about it for a few seconds. Practically seeing the wheels inside his head turn was adorable to watch.
“We used to go to nudist resorts in the past. I saw lots of girls and women naked. It never bothered me. And we often walked naked around the house. I never thought of Julia as…”
I laughed inward at his epiphany. So I helped him out by saying, “And that’s probably why your Mom stopped this whole nudist thing…”
“I guess that makes sense. And I get it now,” he said softly, “but… why do I get so many boners lately? It’s very uncomfortable and awkward sometimes.”
This was good. He started to believe what I said and already trusted me on such a delicate subject. So I said, “You get boners, also called erections, to prepare your body for reproduction.”
“You mean…” he said after my dramatic pause and a few seconds of thinking about it.
“I mean sex, yes.”
“Oh… but I don’t have a girlfriend yet.”
“I know. But your body doesn’t care about that. That’s why it’s good to masturbate. It’s like having sex, but you do it to yourself,” I said, knowing this would put the gears inside his head in overdrive.
“But… I don’t know how. I read about it online, but I’m afraid I’ll break my willie or something,” he said, blushing brightly.
Now it was my turn to spin up the gears inside my head. This was a great opportunity I shouldn’t let go to waste. So I said, “I can’t show you, but you can always ask your Dad. Or another male you trust.”
I just knew he wouldn’t go to his Dad with this. I knew I didn’t want to do this during my own puberty. Dads are asexual creatures at that age. They can’t possibly know how this works. And if they do, they’ll probably make a big fuss out of it.
“My Dad?” he responded, clearly repulsed by the idea. And after a short pause, “Maybe Jason can help me,” which was music to my ears.
“I think you can trust him. And he mentioned that he used to be a nudist too, so he’ll probably understand what you’re going through. And I guess he might not even care if you want to try that stuff over at his place,” I said, laying it on a bit thick.
“You think so?” James said as his eyes lit up, “Mom said I shouldn’t impose myself on him, so…”
“You can always ask, right? If he says no, just let it be. If he says yes, you’re good. Simple as that.”
“But what if Mom finds out?”
Damn! This kid sure overthinks his stuff! I thought for a second and said, “Just ask Jason not to tell your Mom if he says yes. He’ll probably understand.”
“You’re right,” he said after a few seconds.
“I think it’s time for your shower now,” I said, smiling.
James just nodded and, without any hesitation, dropped his boxers. Seeing his cute dick and ass up close in real life was even better than being able to zoom, pause and rewind. Of course, I write about it in my stories, but I never knew kids at that age could actually ooze sexiness the way he did.
He grabbed a towel from his closet and walked over to the bathroom. Right before he entered, I said, “Why don’t you leave both doors open this time? Maybe your sister wants to take a peek at you.”
“Uhh… why would she want to see me?” he asked with confusion all over his face.
“Why do YOU want to see her? She’s probably just as curious about you as you are about her. And maybe she’ll return the favor…”
That seemed to trigger something. He shrugged, and I could see his cute dick chubb up a little as I joined him in the bathroom. I sat down on the toilet as James did his thing. Seeing him take a shower wasn’t sexual at all, but I felt privileged to be able to watch him.
In the corner of my eye, I kept looking at Julia’s door. And sure enough, after a few minutes, as James was washing his hair, she peeked inside. She looked at her brother’s body, and I saw her eyes roam all over him, and they stayed focused on his dick for a while. This was working out better than expected.
When James turned off the water, Julia’s head disappeared, and I got another eyeful of his tight ass. As he started drying his back, he swayed his hips so firmly that his dick slapped left and right against his body. Of course, all boys and men did this occasionally, but his adorable giggle as he did this made me laugh softly too.
When we got back inside James’s room, and he started searching through his drawer for a fresh pair of boxers, I said, “I didn’t mention this, but I’m not always around. I come and go unannounced. Even I don’t know when I’m there and when I’m not, so don’t be surprised if I’m suddenly gone.”
“That’s okay,” he said without any visible emotion as he pulled up his boxers, “I think I’ll go online and look for more info on you. Is that okay with you?”
This was precisely what I wanted! I already rigged his computer for this, so I said, “Of course I am! The more you know about me, the better. And I’m not sure if you know it, but there are a few sites online with good stories about boys your age who are also curious about sex and girls. There’s Lubrican, Nifty, storiesonline, and a few others. You just have to find the right story. Maybe read some of that too?”
“Oh. I… I don’t know. I think my Dad is monitoring the internet feed, so I’m not sure if it’s a good idea. I’m not in the mood for ‘the talk’ with him,” he smiled as he made air quotes saying this.
“I get it. It’s up to you. Maybe ask Jason if he knows a way around it? I just…” I said, figuring it was enough now and wanting to end our first get-together dramatically.
James looked confused and asked, “John?” Then, after a few moments, he did it again but shrugged after he didn’t hear me talking anymore.
James grabbed his short pajama bottoms, put them on, and pulled a t-shirt over his head. I made sure to linger near his bedroom door, so I could get out with the first opportunity I got.
That opportunity came sooner than expected because James opened the door and went downstairs after he pulled down his shirt. As I approached the stairs, I saw their cat walk up. He looked me straight into my eyes, walked up to me, and started rubbing his side against my leg. This was creepy. I didn’t know if animals, or maybe just cats could see me. His coat looked funny with dents in it where my leg was, so I knew now I needed to make sure to stay away from him. Otherwise, he might give away my presence.
After I got rid of the cat and reached the bottom of the stairs, I easily sneaked out of the house and was in my living room before anyone could see me. I got dressed, waited for the invisibility to wear off, and made sure to put the key under the rock I pointed out to James.
I poured myself a nice, big glass of whiskey, which I quickly gulped down. I poured myself another one, feeling pleased with how things were going. Sat behind my computer and checked what James was doing. And sure enough, he was currently browsing the websites I copied and filled with fake articles about hearing voices during puberty.
On his webcam, I kept an eye on him, and it was clear that the more he read about it, the more relaxed he scrolled through the remaining sites. He even scrolled around quickly on the Nifty website, scanning the young friends and incest section. But he only opened one story, which wasn’t a very good one. It was about two adults and was very poorly written. This wasn’t lost on James, and he quickly closed his browser window when he heard his Mom come upstairs.
After she told him it was time for bed, he shut down his computer and went to bed. Maybe it was the alcohol, but the feeling of victory about all this swept through me. I celebrated by drinking another glass and felt myself getting slightly drunk after that.
I undressed and crawled into bed, looking forward to another day. Tomorrow, I’d probably be in bed together with James because I’d let him have that sleepover he wanted without even thinking twice about it.
The image of James in just his underwear, lying next to me, filled my head. And even though I wasn’t planning on doing anything sexual with him, I got hard and jerked myself to a quick orgasm, with images of his dick flopping from left to right in the shower, and his tented boxers, pushing me over the edge.
Copyright 2023 – Jason Crow
All rights reserved
semina sunt quaedam grata futura
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