Barely Paralegal Ch. 04

Chapter 04 - Not 'Til You Finish Your Homework

I wake up Saturday morning, and I'm still trying to make sense of everything that happened the day before. Obviously, the fact that I finally lost my virginity is the biggest headline from yesterday, but even with this undoubtably exciting development, I still can't help but feel a little worried about what's to come.

It's safe to say my first time did not unfold as I had always imagined. I would've figured that even though I'm quite shy, I'd eventually be able to meet a girl my own age, either through school or running, and we'd strike up a friendship. That companionship would turn into romance, we'd start fooling around, become boyfriend and girlfriend, and then one special evening we'd decide to take things all the way. That's how I had always fantasized it would be.

In reality, it wasn't my first girlfriend that led me to losing my virginity, it was my first internship instead. And that's because this fateful summer job comes with a boss named Mark and his 50-year-old wife named Linda, who apparently had been looking for an 18-year-old just like me. Not just for the mundane legal grunt work I had been told about, but also to be the personal sex toy of this middle-aged woman. And don't get me wrong, 90% of me is glad things have worked out the way they have so far. But it's that other 10% that I just can't shake that makes me wonder if I should actually be doing this.

Did I miss out on the typical teenage experience by not having a girlfriend my own age? Is the fact that they're paying me like an employee to have sex with Linda somehow morally wrong? Are they going to make me do things sexually that I don't want to do?

Ok, maybe it's more like 30% of me is worried. But that still leaves a solid 70% that is ecstatic. I got to see, touch, lick and fuck my first real vagina yesterday, and that part was amazing. The physical sensation itself was incredible, but so was the way Linda was completely understanding of my obvious cluelessness. She actually made me feel accepted for who I am, which is no small feat. It makes me want to try even harder next week so I can please her even more and show how great a lover I can become.

Speaking of improving, that reminds me how I need to do a better job shaving. Linda told me I needed to keep a clean shave everyday now, and while technically that only applies to weekdays when I go into work, I figure getting a shave in today and then again on Monday, should ensure my face is nice and smooth like she wants. I'm also not allowed to jerk off while I'm home, but I kind of like this idea of abstaining as it should make me super turned on and ready to go for next week. Although, as I take a quick status check on my cock this morning, one touch is all it takes to realize I'm still really turned on from all of yesterday's events. For a split second, I consider cheating and rubbing one off a quick one here, but then I realize how lame it would be to break one of her two main rules before I even have my first full day of working for her. Time to go shower and shave instead.

Later that Saturday night, I'm having dinner at home with my parents and brother, like we typically do. My brother Tyler happens to be boasting about all the money he just made mowing lawns.

"One hundred and thirty bucks today, can you believe that?" He proudly announces.

"Nice work, sweetie!" My mom commends him. "What're you gonna spend it on?"

"I don't know yet." He answers, before adding, "Maybe I'll take Beth to Six Flags next weekend or something."

Beth is this girl from our high school that Ty is apparently dating now. She's going to be a senior this fall while my brother is a year younger. Now that Tyler has his driver's license, he's been all about the dating lifestyle recently. And no surprise here given his track record, but Beth is both very nice and extremely pretty, so I can't help but be a little jealous of my younger brother.

Ty then turns his attention to me, and says with a sarcastic tone, "How's your nerd job going? Working on your tan much sitting in that dude's basement all day?"

I don't even have time to respond before my dad calls Ty out. "What are you talking about?" My dad says. "Making fun of your brother for having a real job that pays real money is just about the dumbest put down imaginable."

Wow. Go dad. It's so awesome seeing my brother get taken down a peg, that I just can't resist jumping in as well.

"As a matter of fact, I just got a raise this week too!" I proudly exclaim.

"What?!?" My dad instantly reacts with a look that's surprisingly more disgust and confusion than excitement. "Why did Mark give you a raise???" He quickly follows up with.

Oh shit. Should I have not mentioned that? How am I going to explain away the fact that my raise was based purely on having sex with Linda, when I obviously can't tell him anything about that. And otherwise, getting a raise after only two weeks of work doesn't make any sense at all!

"Uhhh..." I struggle to get out. "He just said I was doing a great job so far." Is the best I can come up with. Fuck.

"How much was the raise?" My dad continues with the questioning.

"Ten dollars." I say pretty meekly as I'm now much more worried than excited about sharing this news.

"An hour?" My dad asks still genuinely perplexed. "So twenty-five an hour now?"

I figure I had better act confident here, so I gather my composure and triumphantly say, "Yep! Pretty exciting, right?"

"Well that is GREAT news, honey." My mom chimes in. "I'm so proud of you!"

"Thanks, mom." I respond.

And then I hear something I wasn't expecting, as Tyler goes, "That's pretty impressive. Nice work, dude."

Wow, was that a genuine complement from my brother? Between his reaction and my mom's, maybe this is all going to be ok after all. But then I glance over at my dad and he still looks very skeptical of this supposed pay bump. I'm a little worried what he might be thinking, but I figure it's best not to dwell on the topic.

So we move on to a new conversation and the rest of dinner goes fine. As soon as we're done though, I realize I should probably let Mark know that I spilled the beans on my pay raise. He has stressed how critical it is that I not mention our whole sexual arrangement with his wife to ANYONE, but I honestly don't know if that means I had to keep the raise a secret or not. I hope I didn't fuck this all up!

So I make my way to my room and text my boss.

"Hey Mark, I told my family about my raise. Hope that's ok? Sorry if it's not." I type.

I click send, and then I see the delivered confirmation. It only takes a few seconds before I see the bubble with the three dots appear to indicate he's replying. God I hope he's not mad.

Then the bubble momentarily disappears and the next thing I know my phone starts vibrating. It's a call from Mark.

"Hello?" I answer.

"Hey it's fine. No worries." He immediate tells me.

"Oh ok." I exhale and come down from my brief moment of panic.

"Yeah, I mean the money is going into your bank account so it's not like we could hide it anyway." He then explains. "So honestly it's probably better to be up front about it. It would've been weirder if you DIDN'T tell them you got a raise."

"Yeah you're right." I respond. And once again Mark makes everything seem fine. He's so good at that.

Then he asks me, "So what did you say was the reason for the raise?"

"I just said you thought I was doing a good job. That's it." I reply.

"Ok, perfect. The simpler the better." Mark says. And then he adds, "But hey, do me a favor and if you ever need to chat, don't send any texts. Just call me ok?"

"Yeah, ok. I can do that." I confirm.

"Yeah I know talking on the phone goes against everything your generation stands for." Mark says with a laugh. "But it's definitely better for us given our whole situation, you know?"

"Understood." I respond. I assume he's talking about not wanting any of our conversation in writing? But maybe I'm over thinking things and he just thinks it's easier to stay on the same page if we talk rather than text. Either way, I'm pretty sure I can handle his request.

"Ok great, well have a good rest of your weekend and I'll see you on Monday."

And we conclude our call. Phew. I was genuinely scared there I had royally fucked up, but thankfully I think everything is still fine, even if I am a little paranoid my dad already thinks something weird is going on. But could he possibly imagine the scenario that is actually happening? That his two friends are paying his son to have sex with them (or her more accurately)? I'm the one living it and I don't even fully believe it's real. So if there's no way in a million years he could foresee this, that probably means he's unlikely to ever figure it out on his own, right? It's impossible. It has to be, right?

Monday morning comes around and I'm awake even before my 7am alarm goes off. I think I'm pretty excited for the day, but yet again there's this nagging worry in the back of my mind that Linda has something extreme planned for me this week. At this point, as long as it doesn't involve sticking something in my butt, I'll be relieved no matter what it is. Although, there's a reason why they say, 'careful what you wish for' so I probably shouldn't be so confident there aren't way worse things Linda could come up with.

But anyway, I can't control that right now, so I need to focus on what I can control. Priority number one, shave my face! I managed to make it through the weekend without masturbating, and despite our dinner conversation on Saturday, I didn't spill the beans on our arrangement, so my only homework assignment left is a nice, clean, shave.

After showering, I take my time making sure I don't slice my face open accidentally, and it's a success. I'm looking good and heading off to work. I arrive at my usual time, but my heart is beating faster than ever as I approach the door. I'm even more nervous than I was on Friday, when I had absolutely no idea what was going on and I was worried I might get fired.

Linda answers the door, like always. "Hey sugar!" She says, as she has a seemingly endless supply of pet names for me. She invites me in, and once the door closes behind us she simultaneously kisses me and runs her hand across my cheeks and chin. "So smoooooth. Nice job on following my instructions!"

I smile, and say, "Of course, I wouldn't want to let you down."

Her facial expression quickly changes though as she then abruptly quizzes me, "So when was the last time you ejaculated?"

"Uhhh... Friday. When we had sex?" I answer honestly but nervously.

Linda keeps giving me a stern look for a moment, but then breaks out into a smile. "Good. I can tell you're not lying to me." And then she laughs, before continuing, "So I'll tell you what... I have a few things to take care of first thing this morning, so why don't you come up to my room around 10."

"Ok." I answer simply, but I can't help but think our interaction just now was a little weird. Regardless, I head downstairs, happy that I have a little time to regroup and chat with Mark before my official Linda-time begins. Although, I briefly wonder if some days she won't have any time for me at all, and then I realize I'd probably be pretty disappointed with a scenario like that, so I clearly am looking forward to the time I spend with her, anxiety and all.

I check in with Mark, and to be honest we don't talk about too much this morning. We're both busy, and knowing I only have a limited amount of time downstairs today, I feel like I want to focus and get as much done in these first two hours as possible.

But soon enough, 9:58am rolls around and I mention to Mark, "Your wife asked that I go upstairs at 10 o'clock. Is that ok?"

"Of course! She's the boss." He says with a smile.

So I head on up. When I get to their bedroom, the door is half open so I quietly knock and look on in. I see Linda sitting in bed, under the covers, and she appears to be naked, or at least topless.

"Right on time." She greets me.

"Hi." I say back, and my heart rate is elevated once again.

"Why don't you get naked and come join me." Linda suggests, as she lifts the covers up in an inviting manner.

"Will do!" I say happily, as now I can see that she's not wearing any clothes on her lower half either. So I quickly get rid of my shoes and clothing and practically jump into their giant king-sized bed.

I bound right into Linda and she pulls the covers over us both, and we immediately start kissing. It feels so good to have our two naked bodies lying next to each other in their wonderful bed, as I had been dreaming of this exact moment all weekend long. And then it hits me. In all our naked time together so far, I've barely gotten a chance to feel Linda's giant boobs, let alone play with them, because I've been so singularly focused on her vagina. Well, that's about to change, I think to myself. I don't even ask permission, but instead just reach down and use both hands to start fondling her tits that are right in front of me. They're each bigger than my hand, so I'm alternating between squeezing them individually and smushing them together, but holy shit are they fun to play with. I'm groping her wonderful boobies while the two of us alternate between kissing and just looking into each other's eyes.

"You like them?" Linda asks me playfully.

"Yeah." I respond with a huge grin while taking a second to look down at them and not her face.

And then I decide that I want to try licking them, so I just do it. I don't know what's gotten into me right now, but my own assertiveness is surprising even to me. Maybe my anxiety over what Linda has planned for me today is causing my subconscious to take the initiative so I can try and dictate what happens, instead of her? But either way, I dive right in and start licking her areolas, back and forth between the two. While they don't taste like much, the tiny little bumps feel so good on my tongue and I'm loving every second of this.

Linda starts running her fingers through my hair as she's been prone to do, and I keep my face and mouth buried between her boobs. But before I'm ready to be done and move on to whatever's next, Linda moves her hands down to my armpits and gently nudges me to come up.

"Ok darling, that's enough of that for now." She tells me, in a very teacher to child sort of way. Hearing this takes a little of my euphoria away, both because it means I have to stop motorboating her tits, but also because it reminds me she is clearly the one calling the shots.

"We need to get started on today's lesson." She tells me.

"Ok." I respond. "What's today's lesson?"

"It's something I've wanted to do to you since the beginning." She starts off with, and the fact that she says 'to me' has me worried, because I think I much prefer it when we do things 'to her' if I'm being honest. And then she continues, "We're going to explore..." and then she pauses very deliberately, "all the pleasures..." another pause, "of your adorable..."

Oh fuck. I know where this is going, and I don't want this.

She continues, "tight..."

Fuck. She's definitely talking about my butt. Fuck.

"little..."

Fuck. Is she dragging this out just to torture me???

"butthole!" She finally says emphatically and with a huge grin.

Ugh. What do I say? Do I dare tell her 'no'? I have no fucking idea what I should do, but I do know I don't want to do this. I don't want her to explore by asshole, regardless of what pleasures she promises.

I don't end up telling her how I feel, in fact I don't say anything. But apparently, my face tells her all she needs to know, as after seeing my facial reaction, she says trying to reassure me, "Oh don't worry. It's going to be just fine. I promise I'm not going to hurt you."

She says it quite sincerely, and I'm a little torn whether to trust the words coming out of her mouth, or trust my gut instinct that is still 100% against this idea.

"How do you know that? How do you know that I won't not like it?" I ask her, with a ridiculously worded double-negative.

"You're going to LOVE it." She replies, showing her confidence.

I don't say anything, but my mind is racing. I'm thinking about all sorts of things that she may want to put in my butt. Fingers? Dildos? Her husband's penis? Knowing how freaky this couple seems to be, I don't think I can safely rule anything out right now.

"Ok, first off let's figure out what we're dealing with here." Linda says, as she sits up on the bed while I'm still lying down. "What sorts of things have you experimented with before? What all have you stuck in your ass before?"

What the fuck kind of question is that? And I respond appropriately. "What?" I say. "Nothing. What are you talking about?"

"Wait, you've never stuck ANYTHING in your butt before? Not even out of curiosity?" She asks.

"No." I respond. "Of course not."

"Oh honey, that makes me feel even better." She then gushes, and now I'm completely lost. But then she goes on, "THAT'S why you don't think you'll like it, because you've never even tried it!"

I don't agree with her at all, so I try to explain that as clearly as possible. "I've never tried hitting my hand with a hammer, but I know I won't like that either!" I say. I guess I'm hoping that she'll just accept that I know what I like and don't like, and respect that.

Then Linda goes, "Answer me this. Do you think a man liking the feeling of having something in his ass makes him gay?"

I hesitate. If I'm being honest, I think it kind of does, but I don't think I want to say that. So I say somewhat annoyed, "I don't know."

Then Linda goes on, "The answer is... it doesn't. You know what does? Having romantic feelings for another man. That's what makes a man gay, and that's pretty much the only thing."

"Ok." I respond.

Then she asks, "Have you ever had a crush on another boy?"

That's an easy question, and I immediately answer honestly, "No."

"Have you ever had a crush on a girl?" Linda follows up with.

"Yeah." I say.

"You're straight. It's that simple." She tells me, and I can't really argue with her logic here, but I don't know how she can argue with my logic that I just don't want to do this.

"Now..." Linda then says in a rather stern voice. "I'm not asking you, I'm telling you here. Get up on all fours and lay your chest flat on the bed."

Fuck. This is basically it. This is the moment I've been dreading, because I pretty much have to decide once and for all whether I'm going to continue on down this path I chose with Mark and Linda, or if I'm going to call the whole thing off. I don't think there's a middle ground. What the fuck do I do? And how do I possibly decide in the next ten seconds? Should I obey her instructions and present my naked asshole for her to do with what she pleases? Or should I hop down, put my clothes on, walk out their front door, drive home, and never come back.

Neither option is appealing in the least. Having my asshole penetrated seems downright horrible, but having to go home and come up with some story to tell my parents why I quit this great job? That sounds like a complicated nightmare, not to mention dealing with any repercussions from Mark and Linda, as I'm sure they won't be happy with me.

In the end, after those precious few seconds of intense internal debate, I chose the option that I found to be the lesser of two evils. If I'm really being honest though, it's possible that subconsciously there was part of me that also saw some far fetched upside in the option as well. Maybe deep down I had some morbid curiosity to see what would happen, even if I wasn't able to admit it to myself.

Regardless, I make up my mind and accept my fate. So I get out from underneath the covers and turn to face the headboard. I get up on my knees and raise my ass high in the air, and then I submissively bury my face in one of her pillows. And I don't say a word through any of this.