Chapter Text
You know you can buy just about anything you can imagine on the dark web?
It’s fascinating, really. Silk Road wasn’t the only marketplace, but they were quickly becoming the largest, and though they got raided and shut down a couple years later, other websites have since taken its place with a wide variety of goods offered for sale. Drugs, of course – anything from weed to crack cocaine to methamphetamine, but also Rohypnol, MDMA, LSD, Valium, Viagra, and shrooms, to name a few. I was mildly surprised when I discovered that you could also order fake IDs and other forged documents, stolen credit card and bank account info, leaked login credentials, and a variety of other stolen goods. There’s also guns, predictably, and child p*rnography, obviously. If you dig deeper and know where to look, you can also hire a hacker, hire a kidnapper, or hire an assassin if you’re feeling particularly vengeful. And if you make the right connections, there are even places where you can buy and sell people. But I hadn’t made those connections. Not quite yet.
After switching from PayPal to Bitcoin transactions, I had a few Bitcoins to spend, and decided to buy myself some birthday presents. I had my own steady supply of Ambien now, but I ordered a couple other drugs to experiment with, mostly out of curiosity. I decided that a high quality fake identity was a potentially sound investment, and the best time to get one was before I actually needed it. I sprung for a top-tier identity package, because if I ended up needing it, it wasn’t going to be so I could get into a bar. And I treated myself to a few kiddie p*rn archives I’d been lusting after for a while – one collection of professionally produced videos from Holland, and another that was the largest digital collection of home movies and photos I’d found available anywhere that featured boys and girls together, mostly without adults in view.
I considered a few other purchases from a couple other markets as well, because I’m a naturally curious person, but ultimately decided that curiosity didn’t outweigh the risk involved.
And I was still working through some questions about morality. Ethical behavior, as I’d concluded after my freshman year philosophy class, was whatever you decided it was, because the rules (and especially the laws) were always arbitrary anyway. But I’d never really decided what my rules actually were, and in most cases held to the default morality I’d grown up with – that of mainstream progressive liberal America.
I had a strong sense of fairness, and the idea of balance made intuitive sense to me. Still does to this day, even if I struggle to articulate why. The idea of balance and fairness seems so fundamental to me that I’m not sure it even needs to be explained, so when logic fails, balance and fairness remain my default.
I also more or less felt like people should avoid hurting each other. Society as a whole really only works when people play nice together and don’t hurt each other. Again, I still believe that to be true today, with some caveats. Nowadays, I mostly subscribe to the Utilitarianism school of philosophy, that through our actions and decisions we should all try to “maximize total good, and minimize total bad” in the world, a rather pragmatic – if often subjective – doctrine not terribly dissimilar to the newer philosophic school of Effective Altruism. Given what you know about me, this may come as a bit of a surprise to many of you that I have any sort of moral compass, or care about doing good at all. But remember. I didn’t have to be good in order to do good. I knew I wasn’t a good person. But I still felt an obligation to do more good than harm. Keep my karma in the net positive, as it were. Metaphorically speaking, obviously, because karma is a fairy tale.
I didn’t, of course, see the harm in taking advantage of somebody in ways that wouldn’t hurt them. Taking pictures of them while they’re asleep? I get that most people find that unsavory, but nobody has ever been able to convince me that doing so harms them in any way, unless those pictures get used for blackmail or something. Same thing for touching somebody while they’re unconscious. Unsavory, you say, and I’ll nod and accept that it violates your personal sense of morality. But if they never know it happened, and it leaves no mark, and they wake up the next day and continue on with their happy life, what’s the difference to them? I’ve heard people make nebulous arguments about indirect trauma or some bullsh*t like that. But nobody has ever been able to conclusively tell me that such acts cause any real, direct, concrete harm. Not even a little bit. So it’s an entirely neutral interaction for them, and a highly positive interaction for me, making it all around a net good as far as I’m concerned.
I also didn’t see anything wrong with child p*rnography. At least not the stuff that wasn’t violent, but even then I was on the fence, and logic told me that any distinction there was arbitrary. But the stuff where the kids were either asleep; or smiling, eager participants? I don’t see the harm there, either. Arguments that kiddy p*rn leads to pedos raping kids in real life don’t fly with me. If you think kiddy p*rn leads to child rape, you’re either extremely unaware of the lack of any scientifically demonstrated causal link between p*rn consumption and sexual assault, or you should also be advocating against adult p*rn on the basis that it’s a gateway drug to the assault of adults. And while you’re at it, why don’t you ban rom-coms and romance novels, since they’re obviously the gateway drugs to p*rn?
Anti-child p*rnography activists also harp on about “retraumatization”, and how people who were featured in lewd pictures as children get re-victimized every time somebody looks at their photos, year after year after year, well into their adulthood. I don’t buy it. They don’t know when somebody new looks at their photo, so they can’t possibly be retraumatized every time it happens. They’re only traumatized once by the knowledge that those photos exist and are in circulation, and they need therapy to get over it and move on with their lives. And honestly, it’s just photos, and unless you’re a very special case, you’re just an anonymous child in that photo, so get over it anyway.
All this to say that I had – and have – no moral objections to child p*rnography, and zero compunctions about treating myself for my birthday.
I know, shocking. Bet you didn’t see that coming from a mile away.
Now, my dedication to fairness does throw up a few red flags here and there. For instance, it seems fair to me that child p*rn stars should be compensated for their talents, the same way adult p*rn stars are paid. Back in the good ol’ days of print magazines and hard copy video distribution, those children were often paid to model. Or their parents were paid, but that’s a discussion about child labor, not fair compensation. Nowadays, in the age of smartphones and p*rnHub where people offer up their bodies freely in pixel form without monetary gain, that fairness principle gets muddied pretty quickly. Kids aren’t usually paid for their services, but it’s often their parents who are distributing the pictures and videos, and the analogous adult p*rn that’s homemade rather than produced in a studio is more often than not distributed freely without monetary gain for the adults who are featured.
Still, I feel bad sometimes that I haven’t compensated all the kids I’ve profited off of over the years. But there are significant practical challenges there – I mean I can’t just mail a check to Katy with a thank you note for being my first child model, now can I? So in most cases I do what I can to show them my appreciation indirectly, and the rest of the time I just don’t worry about it. Fairness is an ideal after all, and reality is rarely ideal.
Balance is similarly an ideal. I deserve to be happy and enjoy my life no more or less than anybody else. And yes, I recognize that I take joy in others’ misery occasionally – I’m not completely lacking in self-awareness. But I do what I can to balance things out through my charity work, and putting as much joy and happiness into the world as I reasonably can. And I keep the misery I create contained to my basem*nt, where it can’t spread. Like I said, society as a whole really only works when people play nice together and don’t hurt each other. So I carefully select my guests, and remove them from society before taking them to the basem*nt. Keep my karma as positive as possible when taking happiness for myself. … It also happens to be safer that way.
I digress, however. It’s been a while since I subjected you to one of my tangents, so I suppose we were overdue. We were discussing the dark web, and the cornucopia of sins and illegal paraphernalia that it offers to those who’ve learned to navigate its depths.
You can buy just about anything if you know where to look and have enough bitcoin to offer, but you can also get paid for just about anything. Whether it’s physical or digital goods that you want to sell, or services that you’re willing to perform. Particularly if it’s illegal. I still wasn’t getting rich selling my pictures and videos, but I had a modest and steady income of Bitcoin flowing into my digital wallet.
I wanted more, though. Selling my homemade kiddie p*rn wasn’t the only way to make money, I just hadn’t yet found another option that seemed appropriately low-risk and high-reward.
By now I think you get the idea that I’d become an indispensable part of Xander and Hailey’s lives, and the Lopez kids’ lives too, albeit to a somewhat lesser extent. And they’d all become an indispensable part of my life, too. Honestly, they were the only people keeping me sane, I think. Without them, I’d have depression spiraled for the entirety of the past year. As it was, they were barely able to keep the images of towels tied around teenage necks at bay.
I’d made excellent progress with Xander and Hailey over the course of the summer, and Xander in particular was completely and utterly comfortable around me after that night sharing a sleeping bag with Hunter, and taking turns in his ass. Unfortunately, “completely and utterly comfortable” didn’t necessarily mean he wanted me to f*ck him at every opportunity, but I still had hope that I might be able to convince him to let me do that now and then someday.
He was, however, an enormous help in expanding Hailey’s boundaries, especially after that weekend. He had a strong innate curiosity about all things sex, and still had much to learn and experience when it came to females. With some careful hypnotic disinhibition, that innate curiosity easily overpowered his reservations about the fact that Hailey was his little sister.
For her part, Hailey had almost no compunctions anymore about the fact that Xander was her brother, and her innate curiosity about all things sex was just as strong as her brother’s, but her broader misgivings regarding propriety in general, and trying new things that, for one reason or another, she thought she wasn’t supposed to want to do, were a little more pronounced. With the aid of some more hypnotic disinhibition, however, and carefully making sure that every time we pushed her to try something new it was a fun and exciting experience for her, he and I were well on our way to molding her into a perfect, eager little sex puppet we could play with whenever we wanted. He probably wasn’t really aware of what he was doing, or how he was helping, of course. But that didn’t make his assistance any less helpful in training his sister.
For a full week straight, I dared them to watch each other masturbat* before they went to sleep each night, and reminded them that I knew everything, and they couldn’t lie to me. After the third night, Hailey was the one impatiently reminding her brother that they had to do it, and their mom was confused but pleasantly surprised when her kids started getting themselves ready for bed early. I masturbat*d with them each night, watching and listening from my computer.
She had touched both of our erections a few times, and we’d both touched her privates on occasion as well, including a few times when I’d been able to subtly rub her cl*t for a minute or two, particularly that Fourth of July weekend. But we introduced her to the concept of mutual masturbation one night during a game of Crazy Eights on my living room floor. It didn’t take her long to realize that was even more fun than rubbing herself, and before the night was over, she gave me a full-blown hand job while her brother watched, after which I had to explain to her what the “gloopy stuff” was that came out when I org*smed.
After that, I assigned them another full week of masturbation before bed, this time masturbating each other instead of themselves. They were both adorably awkward and unsure of what to do at first, but they both figured it out about halfway through the week, and started enjoying each other’s assistances.
Like Hailey, young Miguel was an eager student of all things horny, but he and his siblings didn’t join us particularly often, and their visits tended to be shorter, because their mom didn’t work late shifts as often as Carla. He had become much more of a nudist over the course of the summer (much to his mother’s dismay the few times that she caught him), and his older brother had (somewhat reluctantly) taught him how to masturbat* after a little encouragement and slight coercion.
Maria remained a bit of a conundrum. She had been thoroughly indoctrinated in the ethos of traditional, fairytale romances and the Christian ideologies of propriety and virginity that govern the behaviors of young women. She was also saturated with the hormones of adolescence and desperately wanted to fall in love and explore her sexuality, and she had a massive crush on me. Those two competing forces left her in a quagmire of warring emotions, wanting simultaneously to strip naked and jump my bones, while also covering herself up and saving even her first kiss for marriage, though of course that ship had already sailed. It made subtly pushing and expanding her boundaries a rewarding challenge, but also incredibly unpredictable. After the first couple times, she no longer hesitated to join the rest of us in the family changing room showers on Fridays, and eagerly shared a few more back porch sunbathing sessions with me, but was a reluctant participant in the few stripping games I’d hosted after movie nights in July, and couldn’t let her guard down and just have good, horny fun with us, no matter how much she wanted to. I still hadn’t had a good opportunity to hypnotize her, and wasn’t sure I wanted to. I kind of liked the challenge of winning her over to the dark side organically, even if it was incredibly frustrating and strained the limits of my patience. By the time the boys and I went on our backpacking trip, Xander had been the only one permitted to openly grope her (daily for a full week), and only then because she hadn’t really been given a choice in the matter.
I had coaxed her into letting me do more and more of her sunscreen on the back porch, until I was doing her entire body, and was able to briefly massage her breasts as part of the process, and even the outer margins of her vulva. Watching all the competing forces warring across her face as my hands got close was incredibly fun and arousing, but also served as a reminder of just how dangerous a game I was playing, so I was careful to never push too far. In return, she sunscreened me up as well, and I could tell exactly where her sense of propriety won out over her hormones. Turns out that line was about half an inch away from my genitals, beginning at the edge of my patch of trimmed pubic hair. What a tease.
Wanting to avoid a repeat of last year’s misery, I let it be known to a few of my friends that I was turning twenty-one years old on Wednesday, August tenth. Against my better judgment, I let them drag me out to do the obligatory bar crawl downtown.
It was hell, and I regretted it almost immediately. It was loud and dark, and there were way too many people everywhere, and the birthday shots at each bar were disgusting. I drank far too much, puked in a flower planter on our way to yet another bar, and woke up on Mike’s couch. I drove myself home before anybody else in the house was awake.
While I drove, I pondered how I often couldn’t stand being around other people my age. I had no trouble blending in, of course. I hadn’t lost my touch, and everybody loved me. But it was shallow and empty, and only served to remind me how alone I was. They were all just acquaintances, they weren’t really my friends. I didn’t have friends. And I wasn’t sure anymore why I bothered pretending like I did.
I’d have rather spent the night at home, playing games with my neighbors.
They were my friends.
Thursday night, as soon as their mom dropped them off with me and I closed the door, I bent Hailey over my knee, flipped her dress up and pulled her panties down, and gave her ass twenty-one moderate smacks as punishment for forgetting my birthday. Then I did the same thing to Xander, hitting him harder than his sister.
Then I hugged them both long and hard, thanked them both for being such good friends to me, and told them to go get ready for dessert, because we were going to have cake before dinner. And after.
Tuesday, August 16th, 2011, 4:45pm
“Hi boys.”
“Ack!” Xander and Tony both squawked, and immediately tried hiding what they were doing. I smirked.
“Oh. Hi, Mister James,” Xander said a little sheepishly, but stopped trying to hide his erection. Tony relaxed a little, too.
“I see you found my new magazine,” I said, dropping my backpack on the floor next to my desk. This was the first time I’d ever caught them in the act. They must not have heard me come in the front door this time.
“Yeah, um… that’s okay, right?” he asked, still sounding worried. “You’re not, like, mad or anything?”
“Yeah, that’s fine,” I shrugged, and joined them on the bed. “Just, you know, don’t tell your moms or anything. I’m pretty sure they’d both be mad at me for letting you look at them.”
“We won’t!” he promised, and Tony nodded his agreement with a scowl.
“Good. So, whaddaya think? You like the new one?” I’d finally decided they were ready for the gangb*ng magazine after we got home from our backpacking trip, but they hadn’t discovered it in the drawer until this afternoon, apparently. They must have been bored while I was at school attending my second day of classes for the semester. They still had a week and a half before their summer was over.
“Yeah,” Xander grinned, and Tony nodded again.
“What do you like about it?”
“Oh. Um… I think it’s cool how she has, like, five guys or whatever, and she’s doing sex stuff with all of them at the same time,” Xander said, flipping back a couple pages to indicate a very busty brunette who was riding one guy cowgirl style with a giant co*ck in each hand, and one in her mouth. A couple more guys with gigantic erections were waiting their turn in the background. “It kinda looks fun. And she looks like she likes it.”
“She does, doesn’t she? You think you’d like it?”
“No,” Tony said immediately, finally breaking his unusual silence.
“Maybe,” Xander replied at the same time.
“Wait, you mean, like, being in the middle like that?” Tony clarified. “Or just, like, being there?”
“Either one,” I shrugged.
“Being there might be okay,” he admitted.
“I dunno. Might be kinda fun to be in the middle, too,” Xander said. “Just to try it, y’know?”
“No,” he contradicted. “I mean, not unless they were girls, instead of guys. Then that’d be pretty awesome.”
“Oh. Yeah, that’d be cool, too,” Xander agreed. Guys or girls, I thought it would be a hell of a lot of fun to watch him star at the center of a gang bang.
Photos and videos of that would fetch a pretty penny, too.
Xander grabbed his erection and started stroking himself again.
“What about you, Tony? What do you like about it?”
“Oh. Um… I dunno,” he scowled again. “I guess she’s just hot? And… Oh, and there was this one picture–” he flipped forward a few pages and pointed, “–here, where she has two guys in her puss* at the same time, see? I think that’s pretty cool.”
“Yeah,” I nodded. “That does–”
“Hi, Mister James!”
“Ack!” both boys squawked, and tried to hide themselves again.
“I saw your car– Oh.”
“Hey, Hailey,” I smiled at my young neighbor, standing in my bedroom door holding an otter pop. Oiling the sliding glass door onto the back porch so it no longer squeaked had been a mistake.
“Jeez, Hailey!” Xander sighed, and resumed stroking himself again. “You scared us.”
“Wait’re you guys lookin’ at the magazines again?” she asked excitedly. “And jerkin’? With Mister James? Can I look too?”
“Uhh…” Tony grunted uncertainly. I wasn’t really sure how aware he was of the breadth of Hailey’s sexual experience at that point, but her excitement and lack of shock had clearly taken him by surprise.
“Depends,” I said. “Is your mom home?” None of them were wearing socks, but that wasn’t a reliable indicator during the summer, when flip flops and bare feet were the norm. I hadn’t paid attention to whether or not her car was out front when I’d pulled up a few minutes ago.
“Yeah. She said she’s takin’ a nap ‘fore she starts makin’ dinner.”
“Hm… Alright. Yeah, you can come look too, then.”
“Yes!” she grinned, and started running for the bed.
“But!” I stopped her, holding up a finger, and she came to an abrupt halt. “You gotta finish that popsicle first–”
“Okay!”
“–and you gotta take your underwear off. Cost of admission.”
“Done!” she said, crunching on a large chunk of purple ice, and lifted her skirt to proudly show us that she already wasn’t wearing underwear.
“Nice,” I grinned, and she beamed at my approval. She’d already started wearing her skirts and dresses more often, because they fit looser, and she’d outgrown a lot of her shorts and pants. I’d hypnotically suggested to her a couple weeks ago that she liked wearing dresses and skirts more than shorts anyway, because they were more comfortable, and they made it easier to tease boys. As a result, when they’d gone back to school shopping last weekend she hadn’t asked her mom for any new shorts or pants, only dresses and skirts. She’d decided on her own to sometimes go commando underneath, presumably because that made teasing even easier.
Tony finally started stroking himself again as well, watching her as she took another large bite of popsicle and dropped the hem of her skirt. She turned around fast enough to make the flouncy garment flare out, and dashed back out to the kitchen. We heard her slurping, followed by the clatter of the trash can lid, and then she returned at full speed, launching herself into the air to bounce up on the bed with us.
Wednesday, August 17th, 2011, 8:15pm
“Hey Mister James?”
“Hey Xander?”
“D’you think that’s why my mom’s gone tonight?”
“What?” I asked, confused.
“That,” he frowned, pointing at the magazine in front of Hailey. She’d asked if we could look at them again after dessert tonight, and I let her pick which one she wanted to look at. I was a little surprised she hadn’t picked the gay mag at the bottom of the drawer, but then again I wasn’t sure she even knew about that one. I decided I’d pull it out once we were done with this one in a few minutes. “Is that what she’s doing with that guy who picked her up?”
“Oh,” I nodded in understanding. “I think they probably went out to dinner first. But maybe, yeah.”
“Ew,” Hailey complained. “Mom wouldn’t do that!”
“She might,” I said, considering the photo in question. The young brunette was laying back on a coffee table with her legs in a wide V-shape in the air, while a faceless, muscular guy slid his co*ck in her puss*. If I squinted, I supposed she maybe resembled what Carla might have looked like fifteen years ago or so.
“Ew! No way!” Hailey complained again, shaking her head vigorously, though it looked more like she was trying to shake loose that mental image than actually disagreeing. “Why would she do that?”
“Cuz it’s fun,” I shrugged. “And it feels good.”
“What? Really?” she asked, still scowling. “But it’s icky!” That seemed rather rich to me, coming from the girl who’d asked to look at the p*rno mags again, and had jerked her brother off for the fourth night in a row last night while he rubbed her puss* for her. We’d only just sat down on my bed with the magazine, but I expected she’d start jerking him again in a few minutes, then I planned to ask her if she wanted to try stroking me at the same time while I rubbed her little cl*t for her.
“Maybe,” Xander shrugged. “But it’s prolly more fun than gross, right?”
“Yep,” I nodded approvingly at him. “And it’s not even really gross, either. It is a little weird thinking about it being your mom, though.”
“Yeah, that part’s icky,” Xander agreed, and his scowl matched his sister’s.
“It doesn’t look fun,” Hailey insisted, still dubious.
“Why not?” I challenged her gently. “It feels good when you let boys touch you, doesn’t it?”
“Yeah…”
“And you know it feels good when you touch your brother or me.”
“Yeah…”
“And when you touch each other at the same time, too.”
“Yeah…”
“So why wouldn’t it feel good to just skip the middle man? Let a boy touch you with his penis instead of his hand? That way you could both feel good at the same time.”
“Hmm…” she frowned, finding no flaw in my logic, but not yet ready to ignore her gut reaction.
That was alright. She didn’t have to change her mind right away. Even just getting her thinking about it was a start. Xander flipped the page, and I happily explained to his little sister what they were doing in each of the photos, and why people thought it was fun.
Saturday, August 20th, 2011, 10:45pm
“Jim! Took you f*cking long enough, the party’s half over already! C’mere, I haven’t seen you in, like, forever! I was starting to think you were too cool to hang out with us anymore.”
“Hey, Andrew,” I grinned, returning his hug. “Good to see you, too. I’d have come earlier, but I was babysitting the neighbor’s kids, and had to wait till she got home.”
“Babysitting for the neighbor? God, you sound like an actual adult!” he laughed. “Well there’s drinks in the kitchen. Oh! Rob, c’mere! Jim, this is my boyfriend, Rob.”
“Boyfriend?” I asked, raising an eyebrow. “You mean you’re actually settling down? Testing out the ol’ ball and chain, seeing how they fit?”
“Oh shut up,” he said, rolling his eyes and flapping his hand at me. “Rob, this is Jim. He was Nani and my’s roommate a couple years ago. He’s all snark and no bite.”
“Just because I never bit you doesn’t mean I don’t bite,” I warned jokingly, then turned to address Rob, who was just smiling indulgently. “Nice to meet you. And good luck. I’m sure you’ve got your hands full with this one.”
“I can handle him,” he assured me with a knowing grin. “Nice to meet you too.”
After a couple more pleasantries, I excused myself from the conversation, and went to find myself a drink in the kitchen. I didn’t plan to get drunk, but having a cup in my hand would help me blend in, and I could pretend to drink all night.
I poured a generous refill for a cute young blonde girl while I was at it, and she started chatting me up. She was a freshman art major, and came with her roommate, who’d already joined the LGBT Club, and was playing beer pong on the dining room table with Nanjala.
I refilled her drink a couple more times before the night was out, and helped her upstairs to Nanjala’s bedroom, and locked the door. She giggled when I kissed her, and barely noticed when I slid my hands up under her skirt, until I started tugging her panties down. And by that point, she was too drunk to really protest when I got out the condom. She did frown and whimper cutely as I f*cked her, though, and my thumb on her cl*t made sure she got off, too, even though she was barely conscious. She looked so confused when she came, I wondered if she’d ever even had an org*sm before. I didn’t bother asking, though, and she wouldn’t have been able to answer coherently anyway. She was passed out by the time I finished pulling my pants up, and I rolled her onto her side, in case she threw up in her sleep.
I mingled some more downstairs before finally saying goodnight to the few people who were still awake. I drove myself home, and added her panties to my collection. A red lace thong from Victoria’s Secret. The kind of panties you wear when you’re planning on showing them off to a cute guy, and hoping to get laid.
Monday, August 22nd, 2011, 7:45pm
Bzzt bzzt bzzzzzt
NEW MULTIMEDIA MSG
Joel was completely naked except for the blindfold over his eyes, on his back on a picnic table with his legs spread, and pulling his knees up to show off his hole. And fully erect.
Another photo from David arrived a few seconds later, showing his co*ck sliding into Joel’s ass, still in the same position on the picnic table. It was sunny in the photos, so they must have been taken earlier in the day. Probably somewhere remote, up in the mountains, where they could have fun undisturbed. That would also explain why it had taken David nearly ten hours to reply to my text wishing him a happy eighteenth birthday.
I smiled and forwarded both photos to my email so I could add them to my small collection from the two boys, and returned to clearing the backlog of surveillance videos. I’d only had a little homework tonight, but I knew it wouldn’t be long before I’d have to spend all night every night doing homework, and the surveillance DVR hard drives would start filling up.
A moment later I heard a doorbell, too faint to be my own. Out of curiosity, I switched to the live feed of the front of the house, and watched Juana step out onto the small front porch and pull the door closed behind her so she could speak privately with the short, sweaty-looking Latino man who was craning his neck, trying to see past her into the house.
Their conversation was tense, and started out in quiet Spanish, but grew rapidly in volume. Diego, as she addressed him, tried switching to English briefly, but Juana immediately admonished him, clearly wanting to keep their conversation private from the kids inside, who I confirmed later were indeed listening at the door.
Their Spanish was rapidfire and emotional, but I gathered over the course of the next few minutes that Diego was her estranged husband, recently back from somewhere. There was some discussion about money, possibly involving child support, and he insisted that he wanted to see the kids. She staunchly refused, and accused him of being drunk again. He reached for the door, but she moved to block him, and slapped him hard across the cheek, then used both hands to shove him backwards onto the lawn while he was still reeling. After catching his balance, he was fuming and balled his fists, but she just crossed her arms and stood her ground. They exchanged obscenities and gestured angrily at each other for another three minutes before he gave up and stormed off, slammed the door on a beat up sedan that looked older than me, and drove away, leaving behind a faint haze of smoke from the car’s exhaust.
Juana waited until the car was gone before turning to head back inside, where her kids waited. She ignored their questions, and angrily refused to discuss what had happened on the porch, telling them they needed to get ready for bed. They had a big day tomorrow; it was their first day of school.
Saturday, August 27th, 2011, 3:45pm
“Hey, sorry. Had my head in my homework,” I said, answering the door for Carla. It was true, I’d had to finish my train of thought before I lost it, and save the file before I could rush to answer the front door.
“That’s okay, we’re a little early tonight. Or at least not running as late as usual,” Carla chuckled, and ushered Hailey in through the front door. I still wasn’t sure why she insisted on formally dropping them off with me, instead of just sending them over through the back yard, but I appreciated knowing definitively when she left for work.
“You’re fine, no worries. No, uh– No Xander tonight?”
“No, he’s at a sleepover,” Hailey pouted before her mom could answer.
“Oh. I see.”
“Yeah, he’s staying at his friend Hunter’s house tonight,” Carla explained.
“Ah. And you’re upset that you don’t get to have a sleepover with your friends, too?” I asked Hailey.
“Yeah,” she scowled.
“Well, we’ll just have to have as much fun as we can without him,” I suggested with a smile, and ruffled her hair.
“Yeah!” she nodded resolutely, and her mom chuckled.
“Thanks again, James. I’ll try not to be too late getting home tonight.”
“No worries,” I assured her. “Just shoot me a text if you’re going to be super early or late.”
“Okay, I will,” she nodded, and headed for her car while Hailey and I waved goodbye.
“So,” I said, grinning at Hailey as I closed the door and started putting the house into lockdown. “Guess it’s just you and me tonight. Let’s see if we can’t have more fun than your brother, eh?”
“Okay!” she grinned back, liking that idea.
“Awesome. So, whadda you wanna do first?”
We started off with a scoop of ice cream for each of us in our underwear, then had an epic dance-off playing DDR before dinner. After frozen chicken nuggets and more ice cream – this time naked, of course – I let her pick the movie.
I had her sit on my lap while we watched, which she objected to at first, saying she was too old to sit on my lap. I insisted, though, and promised it would be fun. She giggled when I used my knees to hold her legs spread open, and giggled even harder when my erection poked up between her legs.
She was older than Natalie had been a little over two years ago when I’d done this with her, so the ergonomics of frotting myself against her labia and cl*t were a little different, but she quickly figured out what was going on, and it didn’t take her long to realize that it was a lot of fun, and started wiggling her hips to rub herself against my shaft. A few seconds later her juices were flowing just enough to make it a wonderful experience – wet, but not too slippery.
With a little help from my fingers on her cl*t, she org*smed three times over the course of the movie, and I came twice, making her giggle as my sem*n on her belly and mons became lube for more frotting.
Monday, September 5th, 2011, 12:30pm
“Hey Xander, hold up please!” I called ahead. “Let’s all cross the street together.”
“Okay!” he called back over his shoulder, and squealed his bike to a halt just before the crosswalk.
“Why’s he so much faster than us?” Hailey complained.
“Because his bike’s bigger than yours, so it’s easier for him to go faster. Plus yours doesn’t really fit you anymore anyway. And I’m going slow so we don’t leave you behind.” She also kept taking a hand off her handlebars to stop her skirt from flying up.
“Oh. I wish I had a new bike,” she scowled.
“Maybe if you tell your mom you want to ride your bike to school like your brother she’ll get you a new one,” I suggested. “You might have to promise her that you’ll stop growing though.”
“I can’t do that,” she rolled her eyes at me, and swerved a little in the process.
“What, you can’t lie to your mom?”
“I can!” Xander declared proudly as we caught up with him, probably unaware of the context of my question. “I lie to her all the time!”
“Oh yeah?” I asked. “What’s the last lie you told her?”
“Um… Oh! This morning she asked if I put on clean underwear and I said yes!”
“Ew, you put on dirty underwear?” Hailey said as we waited for the crosswalk. She didn’t actually sound all that grossed out by the idea, more like her objection was an obligatory formality. I was reasonably certain she was occasionally guilty of doing the same thing, too. It was hard to tell when all their laundry lived on their bedroom floor.
“What? No, I didn’t put on any underwear,” he grinned.
“Oh, right,” she giggled. “I forgot. Me neither.”
“I can’t believe I’m the only one who put on clean underwear this morning,” I laughed as we started crossing. I’d already known I was the only one wearing underwear, of course – had known that even before they’d shown me after their mom dropped them off. I still watched them get dressed every morning while I ate breakfast in front of my computer. It was a comforting daily ritual that I’d managed to maintain almost every day over the past year.
“Your loss for not goin’ commando!” Xander called as he took off again as soon as we made it safely across. He’d wanted to show me the route he took to get to school, so it was okay that he was leading the way. All three of us had the day off from school, so I was happy to hang out with them while their mom worked extra hours for the Labor Day Weekend sale at the store. I still couldn’t remember what kind of store it was, and didn’t really care.
We made it to his new middle school, and rode our bikes slowly around as much of the building as we could access so he could point out all of his classrooms to his sister and me.
“I forgot you were in band,” I said when he showed us the outside of the auditorium. “Why don’t I ever hear you practicing?”
“Cuz the trumpet’s boring,” he complained. He’d told me a couple weeks ago that he’d signed up for band class, and apparently nobody had explained to him that might not have been what he was expecting. He’d come home dismayed after the first day of school when he discovered that they weren’t going to teach him to play the electric guitar. He hadn’t known what band instrument he wanted to play, and the school knew he couldn’t afford his own instrument, so they’d assigned him one of the trumpets they had for low-income students.
“Boring, huh?”
“Yeah, and I don’t like carrying it back and forth to school.”
“Oh,” I said. “Well, I bet we can find a way to strap it to your handlebars to make it easier when you ride your bike. Bring it home tomorrow, and we’ll see what we can do.”
“Yeah, okay,” he shrugged. Making it easier to transport to and from school wouldn’t fix his enthusiasm, of course. But if he started practicing regularly, maybe his sister would come visit me more often in the afternoons to escape the racket.
Behind the school, we stopped and dismounted, and sat on the picnic table Xander informed us his friends liked to eat lunch at. I pulled a couple water bottles out of my bag, and we all drank deeply, because it was a hot day, on its way to becoming a scorcher later in the afternoon.
“I hafta pee,” Xander announced, wiping his mouth and handing his water bottle back to me.
“Alright,” I said, looking around for a good spot. There wasn’t a whole lot of privacy, as the football field behind the school opened onto a main street, and there weren’t many trees or shrubs. “Where do you wanna go?”
“Um…” he thought about it. “Oh! I think there’s a spot around this way.”
I collected Hailey’s water bottle as well, and we walked our bikes around the side of the school to a spot where a couple annex buildings mostly blocked the view from the streets, though if there were any teachers or custodial staff working the holiday, either in the main building or in any of the annex buildings, they’d have an excellent view. There was only one car in the parking lot, though, so I figured we were safe.
“Alright,” I nodded in approval. “Go ahead.”
“Wait, we’re gonna watch?” Hailey asked in surprise when I made no move to turn around or walk away as her brother held his shirt under his chin and pulled down his elastic waistband to free his beautiful young erection.
“Yeah, why not?” I grinned. “Wait, have you ever watched a boy pee before?”
“No,” she said, eyes going wide. “Can I?”
“Yeah, of course!” I assured her, and motioned for her to go stand closer to her brother so she could get a good look. “Go ahead, don’t be shy. Xander, let your sister watch.”
“Okay,” he shrugged, unconcerned as his little sister eagerly shuffled closer to stand next to him, and I casually stood behind her to watch as well. I don’t have a pissing kink, but that doesn’t mean it isn’t fun watching kids pee. He was facing the nearest annex building, but wasn’t particularly close to it, so there wasn’t any risk of splash-back.
“Hey Xander,” I said a moment later, before he could start going. “D’you always pee like that? Or do you ever pull your skin back first?”
“Sometimes I try pullin’ it back first,” he frowned, “But I always make a mess, cuz I hafta aim different that way.”
“Well, you don’t have to worry about making a mess here,” I pointed out.
“Yeah, you’re right,” he grinned, and immediately slid his foreskin back, revealing his beautifully shiny, light purple glans. His foreskin was still tight, but it didn’t seem quite as tight as it used to be. He shifted again, resuming the golfer’s stance, and concentrated.
“... What’s taking so long?” Hailey asked after a few seconds, sounding confused.
“It’s… always harder when I have a ‘rection,” he explained with another frown. “And I think… I think the thingy’s makin’ it harder, too.”
“The thingy?” Hailey asked, sounding even more confused.
“You know, the butt thingy,” he grumbled.
“The butt plug,” I nodded, mostly to myself. He had the size three plug in, in addition to going commando for our bike ride. Under constant anal stimulation, he’d been fully erect since before we’d gotten on our bikes – I’d been keeping tabs, of course. And I loved that his loose, drapey basketball shorts didn’t do much to hide his erection, either.
“Oh yeah, that,” she nodded. “But why would that make it hard to pee? You don’t pee out of your butt.”
“No,” I agreed, “but boys have a couple valves inside that make it so it’s harder for them to start peeing on accident when they’re erect. And the butt plug is probably pressing up against one of those valves, too.”
“Oh…” she said, sounding thoughtful now. “Huh… okay.”
We fell silent and waited patiently until Xander was finally able to start peeing, and Hailey giggled in excitement as he waved back and forth, spraying the side of the building. He dribbled to a brief stop, then squeezed out a few more spurts before sighing, shaking himself dry a couple times, pulling his foreskin forward again, and finally stuffing himself back in his shorts and letting his t-shirt fall back down.
“That was cool,” Hailey grinned, then her expression soured. “I wish I could do that.”
“Why? Do you need to go, too?” I asked, noticing how her left knee turned in subtly as she said it.
“Yeah, kinda,” she pouted.
“You can try it,” I encouraged her, remembering one of our conversations from last summer, when I’d first informed her that it was indeed possible for a girl to pee standing up. “Have you ever practiced in the shower?” I knew she had, but I couldn’t say so, of course, without explaining the surveillance camera hidden under the shower faucet handle, disguised as a large screw hole.
“Yeah,” she admitted, and blushed a little in cute embarrassment. The way she blushed like that always made my co*ck twitch. It was a shame she was hardly ever embarrassed like that. I should really use the trigger ‘you’re really shy, aren’t you?’ more often.
“Then now seems like a great time to try it for real,” I grinned at her, and Xander nodded vigorously in silent agreement.
“Oh… okay,” she said hesitantly. “But, um…”
“What?” I asked, keeping my voice friendly and reassuring.
“I don’t think I can do it with the thingy in…”
“Oh, yeah,” I nodded, realizing the problem. Rather than one of her usual vagin*l dilators, I’d given her a g-spot vibrator to wear that looked more like a butt plug than a dild*, figuring that was less likely to accidentally fall out while she was riding her bike, while still providing plenty of stretch and stimulation. I was being nice, and hadn’t turned the vibrator on, but I did have the remote in my pocket in case I changed my mind. Of course, the little finger that extended forward so that it could vibrate against her cl*t at the same time was blocking her urethral opening, ensuring that if she tried to pee right now, it would make an enormous mess.
“Should I…”
“Here,” I said, holding my hand out. “You can take it out for a minute, and I’ll hold it for you while you go.”
“Okay,” she nodded in relief. Had she been worried I’d tell her to leave it in anyway? I wasn’t that sad*stic.
Well, I was. But I couldn’t risk being too hard on them. I had to be careful to always keep our games lighthearted and fun. Unfortunately.
Having received my permission, she unhesitatingly and completely immodestly lifted the front of her skirt and reached down to grab the toy while her brother and I watched. With a little bit of a wiggle, a half squat, and some cute grunting, the toy popped out with a faint squelching sound, and she sighed in relief as she plopped it into my waiting palm. It was still a little slick with the lube she’d used to put it in, but her body had added its own lubrication to the toy as well.
“Okay. Now what?” she asked, looking to me for direction.
I grinned, and directed her closer to the annex building, off the sidewalk and onto the weathered patch of brown wood mulch. Then I had her lift her skirt again, spread her legs, and push her hips forward, and instructed her to use her fingers to spread her labia apart too, just for good measure. Xander and I both crouched off to the side where we could get a good view, and I told her she could go whenever she was ready.
She started with a hesitant dribble before gaining confidence and letting loose. It didn’t come out in a tight, tidy stream, of course, but thankfully it wasn’t a wide spray, either, and she immediately found that she had reasonable control. All three of us grinned as she emptied herself out on the ground, until she dribbled to a stop.
“That was so cool!” Xander said excitedly as she stood straight again.
“Yeah!” she beamed, absently wiping her hand on her skirt. “That was crazy! I totally did it; I peed standing up like a boy!”
“You did,” I grinned, matching her enthusiasm and handing her back the toy. She didn’t even complain as she did another half-squat and a few wiggles to work the pink silicone device back inside her vagin*, while her brother and I watched. She did grunt cutely again, though, and I clenched around my own butt plug, watching her. I didn’t particularly enjoy wearing a butt plug, but I enjoyed knowing Xander and Hailey were wearing their toys, and I loved watching them put the toys in. And I’d been pretty thorough in baking the idea of fairness into most of our games, and instilling the virtue of reciprocity into their young minds, so I couldn’t really argue when they insisted that I had to wear a plug whenever they did. At least whenever their toys weren’t the result of losing stakes, obviously. Stakes weren’t about fairness and reciprocity.
With all of us plugged, hydrated, commando, and still grinning, we set off on our bikes again, and I navigated us to Hailey’s school, so I could show her the best bike-friendly route home if she could convince her mom to buy her a new bike. We were all sore, and grateful to remove our toys once we made it back home, though.
Later that week, when Xander finally remembered to bring his trumpet home, I helped him devise a way to secure the case to his handlebars using a couple bungee cords. Then I had him demonstrate for me the note they used to tune their instruments – the A above middle C, apparently. A quick search on YouTube returned a video of a tuning pitch that musicians could use, and he confirmed that was the right note. After dropping him into a trance, I had him imagine that note again, imagine playing it perfectly, and everytime he hit that perfect note, he could feel it, feel it vibrating through his mouth and fingers, radiating down through his whole body, into his butt, and every time he hit that perfect note, he could feel it vibrating in his butt, reverberating in that spot inside his butt that felt so good, so that every time he hit that note, and hit it just perfectly, he could feel it, and it was one of the best feelings in the world, and no matter where he was, whether he was in class at school or at home practicing in his bedroom, he loved that feeling, and could feel it every time he hit that perfect note, that A above middle C, and it felt amazing.
His sister had a very difficult time not giggling riotously through the whole thing and interrupting his trance, but she managed to keep it down, and I made it through the process and brought him back to full consciousness. We decided to test it out, and he snatched up the trumpet again. It took him a couple tries to get the right note, using the YouTube video as a reference, but as soon as he did he cut off abruptly with a startled yelp, and all three of us devolved into giggles. He tried it some more, and it wasn’t until his sixth try that he was able to concentrate enough to hold the note for a couple seconds before lowering the instrument and grinning proudly at his sister and I.
Saturday, September 10th, 2011, 8:45pm
Boredom.
I wasn’t used to sitting alone in my house on a Saturday night. This was only like the third time in over half a year that I wasn’t watching Xander and Hailey while Carla was at work.
Xander was having another sleepover at Hunter’s house, and this time Hailey had managed to wrangle herself an invitation to spend the night at her friend Marissa’s. As a result, I strongly suspected that Carla wouldn’t be coming home after work, either, and would choose to spend the night with her boyfriend instead.
It was also the weekend of the anime convention, but Joel and David weren’t coming to visit this year. Apparently they were both out to their families now, so they didn’t have to be quite as secretive about their relationship anymore, and didn’t need me to provide them with a safe place they could escape to in order to be horny together. They were probably still being sneaky about it, but the stakes were now significantly lower if they got caught.
Juana wasn’t working tonight, so the Lopez kids weren’t likely to come visit, either.
As far as I knew, the queer crowd didn’t even have a party going on this weekend.
So I was sitting alone in my house on a Saturday night. Horny, lonely, and bored.
I had a little bit of homework I could work on, but that seemed like a pathetic way to spend a Saturday night, so I immediately rejected that idea.
After catching up on surveillance footage and updating my website with a new compilation video of Hailey giving handjobs, I turned to one of my favorite dark web forums. There was a new thread sharing photos of a young Indian girl not much older than Hailey getting gang raped by seven teen boys, apparently as retribution for some sort of cultural transgression. The lighting sucked, and the pictures weren’t very good, but they were plentiful, and by the end of the series, she was bleeding, barely conscious, and covered in bruises, piss, and cum. It was hot as f*ck.
Another thread went into great descriptive detail – with photographs – about a group of five boys in Kenya as they went through their tribe’s coming-of-age ceremony, particularly the ritual circumcision. I was surprised to learn that the circumcision was performed while the boys were standing, rather than sitting or laying down. At the end, there was a link to another thread detailing the coming-of-age ceremony for one of the village girls, during which the women of the village held her down while an elder removed the girl’s cl*tor*s with a piece of broken glass. Seemed wasteful to me, but the power the elder had in that moment must have felt incredible.
A collection of leaked crime scene and autopsy photos of an infant boy who’d died after he’d been raped in the ass by his teenage babysitter.
An emaciated girl in a soiled white dress chained to a bed.
A five-year-old whose back was covered in fresh, bleeding red lines from a whip.
I couldn’t help but wonder what it would feel like to cause somebody that much pain. To have that much control over someone. To know that they were completely at your mercy, and you could do absolutely anything you wanted to them, and there was nothing they could do about it. And after you’d taken everything else from them, to watch the light fade from their eyes as you took the only thing they had left.
I’d only gotten the briefest glimpses at that sort of power before, but I’d really liked it. I wanted to taste it again.
Wednesday, September 21st, 2011, 3:20pm
“Hi Mister James!”
“Hey Xander,” I grinned and waved as he bounced up onto the curb on his bike, and rolled around to the side of the house to park. I finished unlocking my front door and went inside. I was home earlier than usual, after my last class of the day had been canceled. I’d have been home two hours earlier if I had a smartphone, and had seen the email the professor had sent out just before lunch. Annoying, but whatever. I’d done some of the required reading for my psychology class, so it hadn’t been a complete waste.
As I’d expected, I’d barely finished peeing when Xander came in the back door. I’d discretely taped a little piece of plastic to the door so it made noise again, but was still able to slide freely.
“How was school?” I asked, coming out of the bathroom as he was slipping his socks off.
“Fine,” he shrugged. “Ms. Waller gave us a pop quiz in math class, but I think I did okay. And Mr. Blumhorst says my embouchure has gotten a lot better.”
“I bet it has. Hey, where’s Tony? I didn’t see him come home with you.”
“Oh, yeah. He got detention.”
“What? Why?”
“He punched Cory Hickam in the nose in the middle of gym class, cuz he called his sister a mamacita or something like that. I was on the other side of the gym, and he wouldn’t talk about it later, so I dunno. He was really mad, though.”
“Oh,” I said, taken aback. “Wow. I never would have expected that.”
“Yeah,” he scowled as he snipped the top off an otter pop for himself. “He’s been acting kinda weird the last coupla weeks, though. Like, ever since school started. Or even before.”
“Weird? Weird how?” He hadn’t been coming over to visit very often, so I hadn’t seen him very much. Come to think of it, though, he had seemed a little different recently. Distant. And reserved.
“Just like… grumpy or whatever. And hanging out with new people, and trying to act cool and stuff.”
“Oh,” I frowned. “Well that’s not very cool. I’m sorry.”
“Yeah,” he shrugged, but his casual tone was belied by his continued scowl. “Whatever. Hey, can I borrow your laptop? I’m s’posed to do an assignment for English, but Mom’s laptop’s like almost as old as me or something, and we don’t have internet anyway.”
“Oh. Yeah, sure. It’s next to the TV, help yourself. You can take it home with you, just don’t forget the power cord. Or you can hang out here if you want, too.”
“Oh, cool. Um… maybe I’ll just do it here, if that’s okay?”
“Sure,” I smiled. “Here, let’s get you set up at the table.”
Tuesday, September 27th, 2011, 6:20pm
“Alright, time for homework,” I announced, after we’d finished our ice cream.
“Aw,” Xander pouted. “I don’t wanna, though. Can’t we just, like, play games or something?” Oh, how I wanted to. They had no idea.
“Just cuz your mom’s on a date doesn’t mean it’s not a school night,” I chided. “You’ve still gotta get your homework done for tomorrow.”
“Aw,” he pouted again, but didn’t protest further.
“But if you finish early,” I added, “maybe we can play some games before bedtime.”
“Okay!” he grinned.
“What about me?” Hailey asked. “I don’t have homework. Can I play games?”
“Nuh-uh,” I shook my head. “Aren’t you forgetting something?”
“Huh?”
“Your mom made me promise I’d make you read your book.”
“Oh yeah,” she scowled. “I forgot. Do I hafta, though? Reading’s boring!”
“Yes, you hafta,” I sighed. “But I’ll make you a deal. If you can sit quietly and do your reading, you can stop when your brother finishes his homework, and we’ll let you choose the game. How’s that sound?”
“Fiiiine,” she groaned dramatically, still scowling. “Xander, you better hurry, though.”
“I will,” he promised solemnly.
I told Hailey she could choose whether she wanted to read on my bed or on the couch, and she chose the couch, stalking away cutely in her daisy-print briefs that were definitely too small for her, which meant that she had a persistent cameltoe that she unconsciously tried to pick out every time she stood up. Her mom had bought her new underwear, too, and she wore it occasionally, but for whatever reason, she’d decided to wear one of the too-small pairs when she got dressed this morning. They pulled even tighter across her skinny ass as she huffed and bent over to pull her book out of her backpack by the front door. Then she stood, hooked a finger in the back leg of her panties to pull the wedgie out of her butt, and flopped herself dramatically on the couch.
After her brother and I were finished watching her little display, I pulled my laptop out for him, and showed him how I’d set it up so he could log in as a separate user, so he had his own account and could keep his files in his own folders and everything. He thought that was pretty cool and thanked me, and got started working on the history essay he said was almost done. He didn’t need the internet tonight, but next time he opened Google Chrome from his new user account, he’d discover that I’d set it up to automatically open a few p*rn tabs in the background. I figured it was about time to introduce him to the wonderful world of internet p*rn, now that he’d taken in all the magazines I had to offer.
To her credit, Hailey was dutifully quiet and focussed as she laid on the couch, reading her book while she sucked idly on the end of a pen. And Xander wore a look of intense concentration, tapping away at the computer and reading from his textbook and the assignment sheet, while I slogged through my statistics homework. My grades in calculus in high school had exempted me from taking most of the required math classes in college, but now in my final year, I hadn’t been able to put off taking a stats class any longer. It wasn’t difficult, just incredibly tedious.
Hailey was briefly very excited when Xander announced that he was done with his History paper, but sulkily returned to reading when he informed us that he still had math homework of his own to do. That didn’t take him long, though, and we all stood, stretched, and put our books away, all of us equally eager for the fun that came next.
When she’d dropped the kids off before her date picked her up, Carla had quietly confided in me that she might be home even later than usual tonight, but had asked me to make sure they still went to bed at a reasonable time anyway, since it was a school night. I’d promised her I would.
I figured that meant we had about two hours in which to have fun. After that, I had to make sure they were in bed to maintain a reasonable safety buffer before their mom got home. That safety buffer was one of the rules I’d come up with for myself, placing limits on our fun each night to make sure we didn’t get carried away and take any unnecessary risks. It required a hell of a lot of discipline and willpower, but it was necessary.
Hailey wanted to play Super Smash Bros, since we hadn’t played that in a while, and her brother and I agreed gamely. It seemed like an appropriately fast-paced option as well.
After losing the first round, I cheerfully removed both Hailey’s and Xander’s underwear with my teeth while they giggled, and after the next round, I made Hailey do the same to me. A few rounds later, I made her stand in the bathtub and pee standing up, so her brother and I could watch again, then when she won I suggested she make her brother let her aim his dick for him while he peed, and she thought that was a great idea.
After that, I suggested we switch up the format of the game and play two-player rounds with the handicap on. Loser would hand their controller over to whoever was sitting out that round, and the winner would give them instructions for what to do while they sat out the next round. With the loser’s handicap constantly rolling over, I figured it should stay a fairly balanced game.
Hailey lost first, and I instructed her to sit with her legs spread, and rub herself while her brother and I played the next round. Then Xander made me do the same thing, and after that Hailey made him take a turn at it.
When she lost again, I made Hailey sit between her brother and I so that she could jerk us both off while we played the next round. After that, Xander had me do the same to him and his sister, and we continued that pattern for several more rounds. I kept intentionally losing, because I really enjoyed touching them both.
After a while I decided to win again, though, so that I could break the cycle, and make Hailey sit in my lap. She knew exactly what I meant when I instructed her to rub herself against me again, and did so enthusiastically while her brother watched in wide-eyed fascination.
I lost, of course, and lacking a better idea, Xander just had me masturbat* them both again through the next round. When he won the second time in a row, however, I suggested he try making his sister sit in his lap too, and he eagerly agreed. It took them a little bit of coordinating to figure out the ergonomics, given how much smaller his erection was than mine, but they got it going, and we played the next round.
I’d have been hard pressed to throw that round, not only because Xander was distracted by what his sister was doing on his lap, but also because he just had a hard time seeing around her. He pouted a little that it hadn’t been fair, but his heart wasn’t really in it, and after he handed the controller over to his sister, he quit complaining entirely when I instructed him to keep sitting like that with her on his lap, and to pick up where she left off rubbing himself against her while she played.
He shuddered through an org*sm a minute and a half into the round, but kept up the frotting after I gave him a gentle reminder to keep going.
We spent the next half hour with Hailey swapping back and forth between her brother and I for whose lap she was sitting on. She didn’t say so, but Xander and I could both tell she enjoyed my lap more, because my larger erection was much easier for her to rub herself against. She had one org*sm while on Xander’s lap and two on mine, mostly because I made sure to give her cl*t some attention with my fingers as well. Xander had a second org*sm as well, and I shot my load all over Hailey’s mons and thighs once.
After that half hour of fun, though, I very regretfully had to usher them back next door, and make them get ready for bed. They both pouted, and I heartily agreed, but I really didn’t know how late to expect Carla to stay out on a school night, and keeping them up late was just too big of a risk.
Don’t get caught.
So I made them a deal. If they brushed their teeth and promised to pretend to be asleep when their mom got home, they could stay up as late as they wanted. Hailey immediately pointed out that they could do that anyway, any day they wanted, and I laughed and told her she was too smart.
“How ‘bout this, then,” I bargained, my co*ck still throbbing, and my balls aching to be released again. “After you brush your teeth, I’ll give you guys one more dare, and you can give me one in return?”
“Hm…” Hailey mused, squinting at me suspiciously. As if I’d ever given her a dare she didn’t think was fun.
“That sounds fair,” Xander shrugged.
“Yeah… okay. Deal,” she nodded.
“Great,” I grinned, and made them carry their backpacks next door while I carried their clothes. I stood in the doorway of the bathroom and enjoyed watching them brush their teeth. Hailey and I both giggled at the way Xander’s boner shook back and forth while he brushed. Then I watched them both empty their bladders one last time, and gave them both a playful swat on their butts as they filed past me into their bedroom.
Hailey was on the top bunk this week, but they both sat down on the bottom bunk and looked at me expectantly.
“So?” Hailey asked impatiently. “Whatcha gonna dare us?”
“Hm…” I said, enjoying the identical expectant, slightly eager looks they were giving me, while they squirmed with impatience. “Okay, I’ve got it.”
“Okay! What?”
“For one whole week,” I said, “You both have to go commando.”
“That’s easy,” Hailey said, frowning a little in disappointment. Her brother shrugged.
“And each day,” I continued, “you have to find someone new, and secretly show them that you aren’t wearing any underwear.”
“Oooh,” Xander nodded in understanding. “That’s harder.”
“Yeah,” Hailey agreed, frowning again. “That’s a lot harder. How’re we s’posed to do that?”
“Easy,” I shrugged. “Just tell them you wanna show them something, and go to the bathroom together. Or sneak behind a tree on the playground or something like that.”
“Oh… yeah, okay,” she nodded.
“When you say someone new each day…” Xander squinted, “you just mean a different person each day, right? Not, like, somebody we’ve never shown before.”
“Hmm, good question,” I replied. “Try to make it someone completely new. But if you haven’t been able to show anybody and you’re running out of time at the end of the day, you can pick somebody you’ve shown before, as long as they’re new for the week, and you convince them to go commando too. And if it’s safe and you have enough time, you have to let them watch you masturbat*.”
“Wow,” Hailey frowned again. “That’s gonna be really hard.”
“Yeah,” I nodded. “But I bet you can do it. You’re creative. And persuasive.”
“A whole week, though?” Xander asked. “What about the weekend? We won’t be at school.”
“Weekends too. I’m sure you can still find somebody new each day. And I expect a daily report from both of you, telling me who you showed and how,” I added. “Bonus points if it’s somebody of the opposite gender.”
“Hm…” Hailey mused, then nodded resolutely with a serious expression that was completely incongruous with her current nudity. “Yeah, okay. S’gonna be hard, but I think I can do it.”
“Yeah,” Xander nodded in agreement. “I think so. Okay.”
“Good,” I grinned. “Okay, your turn. You guys have to agree on a dare to give me. So what’s it gonna be?”
“Oh, I know!” Hailey declared, serious expression vanishing in an instant to be replaced with her usual eager, playful smile. “Erry day for a whole week, I dare you to let us watch you shoot the gloopy stuff!”
“Hah,” I chuckled. “You mean my sem*n? You wanna watch me ejacul*te?”
“Yeah!”
“Alright,” I considered. “Well, that might be hard if your mom’s home. But as long as she isn’t home and it’s safe, yeah. I can do that.”
“Okay,” she nodded, accepting that as a reasonable stipulation. “Starting tonight.”
“Hah, yeah, okay. Starting tonight. Xander? You agree that’s the dare you wanna give me?”
“Um…” he frowned, thinking hard and staring vacantly off into the distance in the direction of my co*ck. “Yeah. I don’t have any other ideas, so that sounds good.”
“Okay,” I nodded, and it was my turn to wear a serious expression, while Hailey grinned in satisfaction. “Then it’s a deal.” What a week it was going to be. Damn. “Alright, I owe you some sem*n, then it really is time for bed, cuz we all have school tomorrow, and your mom’s gonna be home soon. So, did you just wanna watch me do it? Or did you wanna do it yourself?”
