Barely Paralegal Ch. 05

Chapter 05 - Testing My Limits

I've had some miserable homework assignments through my four years of high school. For example, I've never liked math, so I have painful memories of long, hopeless, problem sets that I would sit and stare at for hours not knowing where to even begin. And I'm sure this fall when I go off to college, there will be plenty of long nights at Wash U. where I end up having to choose between finishing some assignment or getting any sleep at all, but not both.

But this homework? It's hard to imagine ever having a worse assignment than the task that sits in front of me right now. And I mean literally in front of me, as on my desk I'm looking at a ballpoint pen and a sharpie marker. Not only do I have to stick each of these two pens up my ass and take a picture, but I have to find three additional objects before the night is over and photograph them inside me as well. And as my boss's wife Linda repeatedly pointed out, all the objects have to be different sizes. Fuck me.

I've already given my bedroom a pretty thorough once-over for any potential items, and I'm struggling to come up with a third, let alone a fourth and fifth makeshift dildo. One of the problems is that now that I've settled on using the sharpie, I'm hoping that will end up being the largest object I use, but that makes it really hard to find four SMALLER items, all with different widths. Having had zero experience prior to today of sticking anything up my ass, and just going off of the not so pleasant feeling of Linda's finger inside me this morning, I don't think I ever want to attempt anything bigger than a sharpie.

Still stumped for ideas in my room, I decide to try a new approach and head to our bathroom. I share the bathroom with my brother Tyler, but he's downstairs playing Xbox, so I figure it's safe to rummage around. I start by checking the drawers near the sink, and the first one I open gives me an idea. Right there in the front of the drawer is a giant box of Q-tips. One of these would be perfect, as it's certainly smaller than a ballpoint pen and it's soft, yet should be firm enough to get in. But then I think, is Linda going to tell me it's TOO small? I mean, it is kind of ridiculously tiny.

Fuck it. I don't have a lot of ideas and she never mentioned a minimum size, so technically it follows her rules. I'm using it. Two to go. I continue searching for ideas, and on our counter I see my electric toothbrush. Nope. Not gonna happen as it's both way too thick and it also has a completely flat base that's a non-starter as far as inserting into me. But while this specific object is a no-go, it gives me an idea. What about a normal, disposable toothbrush?

I have a Ziploc bag below the sink I use whenever we go on a trip, and I know that has a basic toothbrush in it, so I reach down and pull the bag out. Success! And not only does it have the toothbrush, but it also has a disposable razor that seems to have a reasonably sized handle. Hmmm, these could be my fourth and fifth objects right here.

I grab the toothbrush, razor, and a few Q-tips and head back to my room, closing the door behind me. I contemplate locking it, but since it's already 10:30 at night, I figure it's unlikely for anyone to come in at this point. I lay out the five different items on my desk, and my first thought is god, Linda's going to be so disappointed with these. It's so obvious I've chosen the absolute smallest objects I could possibly find, and there's no way she doesn't call me out on this. But what the fuck else can I do?

I genuinely don't want to disappoint Linda, and I REALLY don't want her to get mad at me, but I honestly don't think I can go any bigger? How is it my fault that I don't like sticking things in my ass? Does that make me weird? It doesn't, in fact I'm pretty sure it makes me normal. I'm following the instructions she gave me, so if that's not good enough, than it's clearly her fault in how she laid out the assignment. That's my story, and I'm sticking with it.

So I arrange my five objects. The Q-tip is obviously the smallest, and then next is definitely the ballpoint pen. The sharpie is the biggest, but the razor and toothbrush are a little less clear. The toothbrush starts off small and then gets wider up near the head, while the razor is a consistent width throughout. Maybe it should be razor third and toothbrush fourth, and then I just need to get the toothbrush in far enough to its widest spot. I think that should work.

I figure it's time to do this, and since I have to take pictures I should probably leave the lights on. Knowing how compromising a position I'll be in, now I have no choice but to lock my door, so I do. I head over to my bed with my five objects, and I open up the photo vault app Linda had suggested I download. I fully remove my mesh shorts and boxers, and now I'm sitting on my bed naked from the waist down, ready to fornicate myself for this godforsaken assignment.

Oh shit, I almost forgot about the small bottle of lube Linda had given me, so I go over and retrieve that. I also grab a used t-shirt from my laundry to place underneath me in case things get a little messy. So now I'm all ready to go, and I get into position on my bed. My legs are spread, I'm kind of crouched over, and holy shit is this weird. But I'm going to do it.

The lube has a dispenser cap, but I unscrew that and instead just dip the Q-tip right into it. That gets it plenty wet so I go to insert it. I run the tip of it around my asshole to get the opening a little slick, and then boom, I slide it in. Interesting. That wasn't hard at all, although it is pretty fucking tiny. I push it in a little more and then even experiment with sliding it in and out. The Q-tip's not very long, and it's obviously super thin in the middle, so there's not much feeling during the in-and-out, but I have to say I much prefer having control over this sensation compared to this morning when Linda was ramming her finger in and out of me without my consent.

I push it all the way in so it's up against the other end of its tip, and then I grab my phone and take a picture directly in the photo vault app. It's fucking weird as hell seeing a pic of my asshole, let alone with something in it, but the picture comes out in focus so I'm sure it'll suffice. Ok, on to the pen. I remove the Q-tip and I can't help but notice there appears to be a little shit on the end of it that was inside me. Ewww. So I grab some tissues to dispose of it in, and toss it into the trash next to my bed.

Next, I dip the bottom of the ballpoint pen in the lube. The pen I'm using is about as small a pen as you'll ever see, so it's not thick at all. It's much more rigid than the Q-tip obviously, and this helps to slide it in even more easily. It's quite a big longer too, so I take a minute and experiment with pushing it in and out, and I actually get it all the way up to where the cap of the pen I left on is now at my opening. I figure I might as well take a pic of it in as deep as it'll go, hoping that's what Linda would prefer.

I move on to the last three objects: the razor, the toothbrush, and the sharpie. I lube each of them up, stick them in as far as they will reasonably go, and then take the necessary picture. As I have the last item, the sharpie, still inside me, I'm struck with the realization that this assignment isn't nearly as bad as I had feared. I think the biggest key though is that I'm the one in control, and as crazy as this would've sounded 24 hours ago, I'm forced to admit that I kind of like the sensation right now with this marker inside me. This is especially true once I try lightly jerking myself off, and I get to experience that blissful combination of simultaneous penis and asshole stimulation that Linda had introduced me to this morning.

I lie back on my bed, sharpie in my ass and with my hand on my cock pointing straight up, I think for a second about actually jerking off and making myself cum. I had such a huge buildup to a potential orgasm this morning that never panned out, and on top of that I haven't cum at all since Friday, so it's safe to say I am ready to explode. But as great as it would be to cum while having something stimulating my asshole, I decide once again I'm not going to disobey Linda's orders.

But while I do abandon the idea of jerking off, I instead wonder if perhaps I could fit something a little bigger than a sharpie in my ass? If I'm being honest, I think this marker has felt the best of all five objects, so maybe the ideal size for me is a little larger? If I did find one more object to insert, then I could also delete the pic of the Q-tip and pretend like that never happened, because I'm sure Linda is going to find that item most ridiculous of all.

But as I'm contemplating a sixth object, I realize I still don't have any good candidates that aren't significantly larger. At least nothing that I've found so far. So despite the surprising intrigue around what a slightly bigger object might feel like, I decide that what I've photographed already is good enough to hand in. I get myself cleaned up, wash and return all the items to their rightful locations, and call it a night.

I wake up bright and early, remember my daily shave that Linda requires, and head off to work. I have my five homework pics stored safely in my photo vault, and I'm ready to turn them in. I'm actually feeling quite a bit of that good nervousness, as my new found curiosity in anal play combined with Linda's promise yesterday that I would definitely get to cum, has me cautiously optimistic for how the next 8 hours will unfold.

I arrive at the Dwyers' door, and for the first time since I started working here over two weeks ago, my boss Mark, and not his wife Linda, answers the door.

"Oh hey, Mark." I say, a little off guard.

"Good morning." He responds. And then he says, "She's waiting for you upstairs if you want to head on up."

Oh wow. We're just jumping right into this apparently. This is good, I think? Maybe not, as hearing this news amps my heart rate right up.

"Ok. Sure. Thanks." I say as I nervously walk up the stairs. I get to their bedroom and Linda's in there, fully clothed but seemingly getting the room set up.

"Hey there." Linda says to me, in kind of a seductive and playful tone. I notice the bed is meticulously made, but there are two closed shoeboxes sitting in the middle of it. "Why don't you get undressed." She then tells me, which is clearly more of an order than a suggestion.

"Ok." I answer, as I start removing my clothes. I'm a pretty even split of nervousness and excitement right now. I obviously have no idea what she has planned for me, but in my mind I'm hoping for one of two things, and shockingly both of them involve my butthole.

I'm thinking maybe she'll eat my ass again, but this time one of us will jerk my cock off at the same time. I can't imagine that would be anything short of incredible. But if not that, then maybe after viewing the pictures of everything I stuck in my ass, she'll try sticking something inside me too? Perhaps it'll be something that's slightly larger than the sharpie, like I was curious about? And then maybe while she's doing that, she'll jerk me off at the same time, or better yet give me a blowjob? God, that would be amazing. Either way, I hope it's one of those two things, because I really need to cum.

Once I get fully undressed, she sits down on the bed, casually moves the two shoeboxes out of the way, and pats for me to have a seat. I'm a little disappointed that she's still clothed, as I much prefer our time up here when we're both naked.

"Do you have your homework?" She asks as I sit down.

"Oh yeah, one sec." I tell her as I reach into my jeans on the floor to retrieve my phone. I swipe over to open up my photo vault app, and then I ask, "Should I start with the first picture?"

"Yep. I'm excited to see what items you chose." She tells me with a smile.

I'm pretty nervous. I'm sure I'd be nervous no matter what, but I know choosing a Q-tip as my first object is not going to go over well. But I obviously have no choice at this point, so I open up the first pic and point the phone so she can see.

Linda kind of squints, then takes the phone from my hand and pinches to zoom in. Then she gets an almost disgusted look on her face, looks up at me, and asks, "Is that a fucking Q-tip?"

"Yeah." I meekly respond. "But the objects get bigger after that."

Linda hands the phone back to me and says in a disappointed tone, "This is not a good start. Not what I had in mind at all."

"Ok. Ok. I know, I'm sorry." I plead. "You have to understand I've never done this before." I figure the pictures do get better so I quickly move onto the next pic and show her the ballpoint pen in my ass.

Linda looks at it and simply says, "Ok, next."

"Ok." I say and now I'm worried she's actually pissed.

I show her the razor handle in me.

"Next." She says, still not amused in the least.

I try the toothbrush one.

"Mmmm-hmmm. And the last one?" She says.

"Here, a sharpie." I say as I show her the final picture in the series.

It seems like after she saw the first picture of that pathetic little Q-tip in my butthole, Linda became disinterested in reviewing the remainder of my assignment. There's no doubt in my mind she's disappointed with me, and as I finish showing her the last pic, she turns, looks at me and goes, "You do understand the point of homework, don't you?"

I'm not sure if she means in this particular instance, or just homework in general, so I answer vaguely, "To learn something?"

Linda kind of nods and and says, "Yeah, that can be one reason." Then she goes on, "But there can be another reason too. Homework is what helps prepare you for your tests."

She says this quite ominously, without any sign of a smirk or smile, which makes me really nervous. What the fuck does she mean by 'tests'? Is she going to give my asshole some sort of test???

I'm scared of the answer, but I can't help myself. "Am I gonna have a test on this?" I ask.

Linda looks at me, then looks over at the shoeboxes next to us on the bed, and she taps one of the boxes and says, "You'd better believe it. We're gonna do it right now."

Oh shit, there's my extreme anxiety rushing back. I'm sitting here naked, Linda is completely clothed, and there's clearly something in that shoebox that she's about to stick up my ass, and there's no way it's going to be slightly larger than the sharpie. I'm sure it's going to be SIGNIFICANTLY larger than a sharpie. Fuck, fuck, fuck. I know a few moments ago I was kind of, sort of, hoping for something like this. But I definitely do not want this.

My heart is beating out of my chest, and my instincts are to get defensive. "You never said there would be a test." I try to tell her.

"You're right. My mistake. It's not a test, it's a pop quiz." She clarifies while finally losing the serious look on her face in exchange for a grin. And then she says, "Look, you and I both know you did a pretty terrible job with your homework last night. I mean that was the absolute, bare minimum you could've done." She pauses to look at me and then asks, "You do know that, right?"

I don't know whether to agree with her or try to defend myself, so I choose neither. "Was it really that bad?" I ask.

"Honey, that sharpie would've been a perfect choice for your first item, or MAYBE your second. But to end with that???" She tells me with a half-scolding, half-laughing tone.

"Ok. You're right." I admit.

"But look, all you did was hurt yourself. Because now, your test... sorry, pop quiz... this morning is going to seem a lot harder because you didn't put the effort into your homework." Linda tells me, and then adds, "It's just like your teachers used to say, your homework isn't for them, it's for you."

I have to admit, Linda's metaphor here is pretty spot on, because the prospect of her sticking whatever huge thing is in that shoebox up my ass is certainly going to feel like taking a pre-calc test I'm woefully unprepared for. Although if given the choice right this second, I'd take a dreaded math test over this, any day of the week.

"Ok get up on the bed." Linda orders me, and I realize this is already happening. She then reaches over and grabs the other shoebox, not the one she originally had tapped with my supposed test in it. She opens it up and takes out a couple of long straps with some sort of Velcro on them. What the fuck, am I getting tied up?

Linda then walks around to the back of the bed and starts attaching a strap to the back left corner bed post. Wow, I am getting tied up. This is kind of frightening, but perhaps the slightest bit intriguing? It's 100% nerve wracking though. Without saying a word, she takes my wrist and secures the strap with some serious, industrial strength Velcro. Then she takes a second strap and does the same to my other wrist and the bedpost on the other side. My arms are officially tied to the bed now.

"You look like a deer in headlights." Linda says with a laugh as she assesses my current state of restraint.

"Why do I have to be tied up??" I ask.

"It's mainly so you can't touch yourself. Can you reach your cock?" She asks.

There is a fair amount of leeway with the length of the straps, but when I pull my arms in, I'm about a foot short of reaching my penis. The restraints are pretty secure, not anything crazy where I wouldn't be able to eventually get out if she just up and left, but certainly nothing I can just slip out of whenever I want.

"Perfect." Linda says. And then she tells me with a smile, "It's time to begin." She then opens up the other shoebox, reaches in and pulls out a big, black, dildo. Well, to be honest, it's not ridiculously huge. Actually it looks to be roughly the same size as my cock, but it's not molded to look like a penis or anything as it's got a fair amount of curve to it and it's made up of a number of smooth bumps rather than a single shaft and head. Nonetheless, it's fucking intimidating.

"So this..." Linda says, adding a dramatic pause, "...is a prostate massager. I think you're really gonna like it."

I don't know what a prostate massager is, but I have to assume that's just a fancy name for a dildo and she's planning on sticking that thing up my butt. Instinctively, I check my restraints again by trying to bring my arms forward, and yep, I'm not going anywhere.

Linda continues. "So this is specifically designed for men, and its shape will make sure to stimulate your prostate once it's all the way in." Fuck, she just confirmed it's going inside me. "And on top of that, it vibrates!" As she says that, she presses some sort of button and I can hear the device start humming. She quickly switches it back off though.

I don't know what to think. I'm pretty scared of what's going to happen here, but when I look down at my penis, I'm rock hard and sticking straight up. So clearly my mind and cock are not on the same page. There's no doubt this black dildo is bigger than what I was imagining would be the next step up in any anal experimentation of mine, but to be honest I don't think it's as big as I was initially fearing when Linda told me about the test in her shoebox.

As I glance at both the dildo and then my penis, trying to fully gauge the size of this sex toy, I think Linda sees me doing this as she then brings it and places it right next to my stiff cock. "Pretty close, I'd say." Linda comments, referencing the two objects' similarity in size. Now that I can see them side-by-side, it's clear the toy is actually a little shorter than I am, but I'm sure it's still at least six if not six and a half inches in length. And while the tip of it is also smaller than the head of my penis, it gradually widens enough that the base of this sex toy is significantly wider than the shaft of my cock.