Barely Paralegal

Chapter 02 - Job Within A Job

My boss's wife, Linda, is leading me upstairs, and I'm both giddy with excitement and extremely nervous, all at the same time. As we leave the home office in their basement, where I've been interning for the last two weeks, Linda holds my hand while suggesting, "Why don't we head up to the bedroom?"

"Ok." I respond, while she guides me towards the next set of stairs.

At this point, I have no idea what to expect will happen once we get upstairs. This woman knows I'm a complete and total virgin, but all I know about her sexually is that she apparently has a fetish for 18-year-olds like me. I think she's around 50 years old herself, but that's just a guess. Linda looks like she could be the mom of any one of my friends, but ever since I found out that she might want to have sex with me, all I can do is look at her as if she's the girl, or more accurately 'woman', I can finally lose my virginity to.

While the thought of having sexual intercourse is clearly top of mind, to be honest, just the thought of having my very first kiss in a few moments is pretty nerve wracking. And then there are all the intermediate steps between those two bookend events of sexual experience. I wonder how many of those we might do today?

Back when I was in fifth grade, a girl named Melanie asked me if I wanted to hold her hand while our combined classes all watched a movie about volcanos in the gym of our school. I still to this day don't know why she asked me that, but I gladly accepted her offer and remember greatly enjoying being able to hold her hand. Shortly thereafter, I reflected on that moment and decided to create a way to secretly document that first experience, as well as potentially all my other firsts that were still to come.

I haven't looked at it in years, but hidden in my bedroom is a folded up piece of paper, and at the top is a line that says "held hands", followed by Melanie's initials (M.S.) and the date of that fantastic volcano movie. The next line has a spot for "first kiss". And after that there are a bunch more like, "first real date", "first time touching a boob", "first time seeing a naked lady", and even "first time licking a vagina". All in all, there are probably about 10 lines of sexual accomplishments on the list, and the very last one is of course, "lose my virginity".

Each line has its own spot for the initials of the girl, and the date the event happened, and here we are more than 7 years later and the only line that's ever been filled in is the original one about holding hands with Melanie. I think it's safe to say I figured I'd be further on down that list by now, but as Linda and I walk up the stairs to her bedroom, the thought crosses my mind. After such a long drought, am I going to get to cross off my entire secret list in one day?

Once we get upstairs, Mark's wife leads me to the master bedroom of their house. We walk in and I can't help but notice how fancy everything is. It's not just their giant king-sized bed that's immaculately made up, but also the real paintings and ornate sculptures they have scattered about that are unlike any bedroom I've ever stepped foot in. They even have a super fancy chandelier over their massive bed. I knew the Dwyers were well off, but the way their bedroom is decorated just confirms it.

Their bedroom Is on the corner of their second floor, so they have windows on adjacent sides, and Linda has them all open on this beautiful summer morning. Even in the short time I've been standing here, I've already felt a pleasant breeze flow through the room causing the drapes on the windows to flutter. Outside, I can hear the drone of a lawnmower off in the distance. And as I take all of this in, I realize I'm purposefully looking around the room because I'm too nervous to focus on Linda and what she has planned for me. It's so weird because I've wanted this moment to come for so long, but now that I think it might actually be here, part of me feels willing to wait a little longer?

"What do you think of our bedroom?" Linda asks me.

"It's REALLY nice." I stress.

"Thanks! You're such a sweet kid." She responds, and then she takes a few steps towards me and takes both my hands with hers. With her directly across from me and the two of us holding hands, I have no choice but to look right at Linda and make direct eye contact.

"Have you really never kissed a girl before?" she asks me. This triggers a fresh wave of both embarrassment and nervousness and I struggle to even answer the question.

Eventually, I get the word "No" out and immediately after, she releases my left hand and uses her right to place a finger up to my mouth and make contact with my lips. Linda is relatively tall, but she's still probably 4 or 5 inches shorter than my 6'2" frame, so she's peering up at me as she touches my mouth.

"Don't feel bad at all. It's soooooo hot that you haven't." Linda says, almost whispering. "I love how innocent you are, it's adorable." My heart is now beating out of my chest, as it's clear this is getting more and more real by the second. And then she continues on, "And besides, you're going to get to kiss me right now." As she says this, she takes both her arms and places them on my shoulders and gives me a big smile before finishing with, "That is, if you want to of course."

At this point her face is less than a foot from mine and I can even feel the warmth of her breath. I can't imagine how weird it would be on so many levels for me to say no right now, so I figure I pretty much have to go through with this. I nod my head slightly to indicate my approval.

As soon as I do this, Linda moves her head up and pulls me towards her at the same time. I move in, and not really knowing whether I'm supposed to open my mouth here or not, I default to basically doing nothing and keeping my lips in their resting, closed position. Soon enough though, she makes contact with me and I can feel her mouth touching mine.

My eyes are open, but I can see that hers are closed. She's obviously right in front of my face, and I'm kinda frozen in action not knowing how to kiss or what to do. All I'm able to do is look around in panic, trying to see past her head so I can focus on anything other than what is actually happening. I have no idea why I'm not relishing this moment of my first kiss, but at least so far, I feel like I'm barely participating.

With my mouth still closed, I can feel Linda open hers and kind of take my upper lip between her two lips. This pulls me in even more, and I finally decide to close my eyes too. And holy shit, does this make a huge difference. With nothing to focus on visually, I can actually concentrate on the physical act of kissing, and for the first time I feel like I'm actually enjoying what is happening. I start using my lips to apply some pressure and kiss her back, and once I do, I feel Linda reach one of her hands up and use it to pull my head forcefully towards hers.

Once she does this, the pressure of our two mouths on each other is greatly increased. She then turns her head slightly to her right while using her lips to force my mouth open and plunge her tongue inside me. Her strong, slippery, wet tongue in my mouth is unlike any sensation I've ever felt before. I can clearly taste her breath now too, and while I wouldn't describe it as either good nor bad, it's pretty apparent. I instinctively retreat my own tongue to give her's room, but it feels like she's actively searching to make contact, and I'm helpless to keep them apart. The feeling of our two tongues touching is definitely the weirdest sensation yet, but after the initial shock of this connection, I quickly get used to the feeling and start actively circling her tongue with mine.

We're officially making out now, and to be honest it's not too bad. Kind of cool, actually. I almost forget that she's thirty years older than I am and this scenario is absolutely nothing like I ever could've imagined. As we continue to kiss, Linda's hands start actively moving around. She generally is keeping one hand on the back of my head to hold me in place, but she continuously switches off which hand of hers is doing this. Meanwhile, she's using her other hand to rub up and down the back of my shirt. At one point, Linda reaches down and starts feeling around my butt before quickly escalating the situation by grabbing and firmly cupping one of my ass cheeks.

I instinctively start using my hands too and start rubbing the back of her shirt up and down. I can't help but feel her bra strap while doing this, which just reminds me of the fact that I might soon get to see and feel Linda's tits. Since she's still actively grabbing my ass, I decide it's probably ok for me to feel hers as well, so I just go ahead and do it.

I reach down her backside and place both of my hands, stretched out as wide as can be, right on each of her round ass cheeks. As I do this, I apply a little bit of pressure so I'm actually grabbing them and pulling her into me at the same time. Linda's wearing stretchy pants again today, so there's not much material there and it really feels like I'm just holding her ass. Her butt is super soft and squishy, and the sensation of grabbing it is really satisfying. I find myself squeezing and then releasing over and over again, as I relish my chance to grope this older woman.

In addition to feeling up Linda's ass, I can't help but notice her boobs are now pressed against my own chest. She has such huge, soft tits, that I'd be so curious to explore, but for now I have to settle for experiencing them tangentially through my own chest. Either way, it's safe to say I'm officially getting to experience a girl's body for the first time in my life. And also for the first time since I got up to her bedroom, I can feel a boner growing in my jeans. Up until this point, I think I was a little too overwhelmed and nervous to actually get an erection, but clearly this feeling of our two bodies pressed against each other has finally triggered one that I'm helpless to control.

At this point, Linda has switched from just one hand feeling my ass to having both of them pull me into her every bit as hard as I'm holding her to me. Our four hands are working together to keep our pelvises firmly pressed against each other, and now I'm sure she must be able to feel my hard-on. The feeling of our crotches together gives me just the slightest preview of what sex might feel like, and holy shit this feels so good, that I can't even begin to comprehend how amazing actual sex must be. I can tell Linda is enjoying it too, as each time we grind our crotches together a little harder, I hear her let out a soft, moany exhale.

After just a minute or two of this, Linda releases her hands and opens up her eyes. She then looks up at me and asks, "How was your first kiss?"

I can't help but feel embarrassed hearing that question out loud, but I'm still able to respond, "Really nice."

While still gently holding onto my hips, Linda responds with a smile. "You actually seem to know what you're doing." I'm not sure why, but this makes me feel really good. Part of it I'm sure is I was pretty paranoid she'd think I was a terrible kisser, but apparently I'm not?

Linda doesn't seem to dwell on this exchange long though, as she next moves her attention back to me, and specifically my body. She breaks eye contact with me and instead looks down and starts using her hands to feel the front of my body. She aggressively runs her hands on the outside of my clothes, up across my chest, and even down each one of my thighs. She then untucks my shirt from my jeans and sticks both her hands underneath it to start caressing my bare stomach and chest. I'm standing here pretty still, not sure how I feel about this, but not preventing her from doing any of it either.

Linda then pauses her groping, looks back up at me and says, "I REALLY need to see you completely naked. I NEED to see your body."

Oh boy. I love that she wants that, but hearing her say it just ratchets up my nervousness to a new all-time high.

I don't respond verbally, and am still just kind of frozen in place. Linda apparently thinks she has all the consent she needs, because she takes ahold of the bottom of my shirt with her two hands and gradually starts lifting it up. I instinctively go along with it and start slowly raising my arms out until she's able to remove my collared, short sleeved shirt right off and over my outstretched limbs.

Linda casually tosses my shirt aside and returns both her hands and her attention to my now bare chest. I'm so skinny that I've always been paranoid my torso is actually concaved in, but for whatever reason this middle-aged woman seems to find my body attractive.

"I looooove how fit you are." She says as she runs her hands all across my chest. Linda then moves closer and actually starts kissing my body. First it's my pecs and nipples, but then she crouches lower and starts both kissing and licking my abdomen. It's a weird feeling and a weird situation over all, including the fact that I can both feel and see the saliva she's leaving behind on my body. I'm sure I've fantasized about licking a naked girl's body many times, but I can't help but be in disbelief that Linda's actually enjoying doing this to me, but clearly she is.

Soon enough though, I realize the next huge milestone is at hand, as Linda lowers herself all the way down to her knees, looks right up at my face, and grabs the end of my belt and pulls it through its buckle. Yep, she's about to take off my pants, see my penis, and who knows what will happen after that.

My cock is still rock hard, and my heart is still racing away, and I'm still powerless to ask her to stop or even slowdown. I think if given the choice, I'd prefer she not rush into this right now, but if I can't even tell her to stop, how is she supposed to know? Instead, I stare down intently watching the whole situation unfold.

She undoes my belt to where both ends are hanging freely to each side. She next unbuttons my jeans and proceeds to slowly unzip my fly, all without breaking eye contact with me. With my jeans now undone and loose, she gently pulls them down until they get stuck at my shoes. I still have my boxer shorts on, but I'm genuinely curious whether she's going to just leave my pants at my ankles or if she's still intent on getting me completely naked.

I have the answer to my question soon enough, as she lifts up my right foot and pulls my shoe off, not even bothering to untie it. She quickly follows by also taking my sock off before proceeding to do the same thing with my left foot. With my feet bare, she has no problem removing my jeans and tossing them aside next to my shirt.

I'm now standing almost naked, with only a thin pair of boxer shorts doing their best to contain my completely hard penis, but there's clearly no hiding my arousement as it's sticking straight out and pitching a tent.

"Oh my god, what a glorious cock." I hear Linda say quietly, but almost as if she's speaking to herself and not to me. And she can't even fully see it yet either, as it's still covered by my underwear. But then she looks up at me and says, "I figured with how tall you are and the size of your feet, it was going to be impressive." She then gets a big grin and says, "There's just nothing sexier than a long, young, cock."

Guys obviously talk all the time about penis size and how much women love a large cock, but to be honest I always assumed that was mostly bullshit. I always figured that as long as you knew how to be a good lover, girls would be ok with whatever penis you had. And from hearing my friends brag about their 8 and 9-inch dicks, to seeing what penises actually looked like in online porn, I knew I was going to have to get by with just an average-sized penis.

But here I was about to have someone see my hard dick for the first time ever, and Linda seems to already be impressed with it, even underneath my boxers. Perhaps it's just a flattering view having it stretch my underwear out like it is? Or maybe her husband, Mark, happens to have a small cock? Either way, I hope she's not disappointed once she sees it for real.

Still on her knees, but apparently waiting to fully undress me, Linda looks up and asks with a mischievous grin, "Have you ever measured it?"

The truth is I have, many times in fact, but that's obviously embarrassing to admit so the best I can respond is, "Maybe?"

"Oh that's so hot to think about. You lying in your bed, holding your stiffie next to a ruler... stretching it out as far as you can. Fuck." She says. "So how long is it?"

I figure I might as well be honest since she seems so into this, so I tell her the truth, "6 and 7/8ths of an inch."

"Oh fuck. You're so adorable." Linda responds as she stands up. She actually gives me a soft kiss and then pulls back away and says, "I love how large that is. I love how precise a measurement that is. And I love how you could've easily rounded up, but you didn't." And then she just looks as me and smiles.

"Isn't that just like an average size for a penis?" I genuinely ask.

"Oh sweetie, no. No, no, not by a long shot." She quickly answers back.

"But I know a ton of guys at school that have bigger penises than that." I tell her.

"Have you ever seen these dicks?" She asks.

"Well, no..." I answer, and as soon as Linda hears me say that, she interrupts me.

"Your friends are full of shit. I guarantee it." She then takes her hand and places it gently on my boxer shorts, right where my cock is pressing out. For the first time ever, someone is touching my penis (well almost) and it's obviously exhilarating. She then says, "I would bet anything you have the biggest cock of all your friends, and I know for a fact it's going to be the biggest cock I've ever had." Holy shit does that both intimidate me and make me feel relieved all at the same time.

And with that, she gives me another kiss, but lingers a little bit longer this time. Once she's done, she then lowers herself back down onto her knees, and then wastes no time in starting to pull my underwear down. As the waistband passes over my penis, it uncoils my cock, causing it to spring forcefully back up once it's free. Linda then slides my boxers off my feet, and now I'm standing here in this married couple's master bedroom completely naked, while Linda kneels before me, still completely clothed.

A number of thoughts are running through my mind, but primarily it's the question of what is going to happen next? Based on the fact that I'm currently naked and she's currently not, it seems like Linda might be planning on giving me a blow job? Like most guys my age, I think about sexual intercourse a lot. I also think about receiving oral sex, and I can't begin to fathom what either one would feel like. But to be honest, the one act that I probably fantasize about more than anything else, including those two I just mentioned, is eating pussy.

When I look at porn online, the genre I spend far and away the most time watching is lesbian porn. And the main reason why is I'm so fascinated with the idea of licking a vagina, and there's no type of porn more geared towards pussy licking than girl-on-girl. I'm not even sure why I'm so fascinated by this act, but I think it's probably because the vagina is such a complete and total mystery to me, and there's no more intimate way to experience something than by tasting it in your mouth. I'm so curious to know what it would feel like, what it would taste like, and how a girl would actually react to my doing those things.

It's such an obsession, that I'm even paranoid that after all this build up, I won't even like it. Growing up, guys always talked about how much pussy tastes like fish, and I've never been a fan of seafood. I can remember countless standoffs with my parents over being forced to eat some gross salmon dish my mom prepared, and the smell and taste of it still makes me shudder. Could I really find the smell and taste of vagina that unappealing? Looking at a picture or video of it, I can't imagine not loving it, but I have no idea what it'll actually be like in real life. Either way, I'm dying to at least give it a try.