Barely Paralegal Ch. 03

And as I'm lying here on top of her, I realize that I'm so close to actually having sex that I can practically feel it. Something that has always seemed so inconceivable, now seems so shockingly obvious. I instinctively start rocking my hips slightly, grinding my dick externally against Linda's body while I lie on top of her, and holy shit it feels like the most natural movement I've ever made in my entire life. It sounds hyperbolic, but it simply feels like I was born to do this.

I'm not saying a word, but as I continue to dry hump her, Linda reaches down to asses the situation and grabs ahold of my erect penis.

"There's that long cock I remember from yesterday." She says with a big grin, just inches from my face. I can't help but enjoy the jolt that rushes through my body with that still novel feeling of another person touching my genitals. And then Linda says, "You're wet. I'm wet. You can just slide it right in."

My heart is beating like crazy. I'm so excited. The thought also crosses my mind that maybe it's good that I embarrassingly came in my pants before? I realize that if I hadn't, I'd surely be in danger of blowing my load right this second. But instead, my cock is rock hard, but thanks to my first release, I feel comfortably in control of my next orgasm.

I lift myself slightly off of Linda and asses what's in front of me. This middle-aged woman is about to let me have sex with her. Her big floppy tits are hanging slightly to the sides of her chest. Her stomach looks so soft and cushiony, but it's not nearly as inviting as what's directly below it. Her pussy is so wet, flushed, and disheveled in appearance that it kind of looks like it's ALREADY been fucked. And just above her vaginal opening is my hard dick, pointing straight out into the air, waiting for me to finally put it where it belongs.

I don't want to waste any more time, so I grab ahold of my cock, point it down so it lines up with Linda's vagina, and I push forward. To my gleeful surprise, it slides in without the slightest bit of resistance. One second I'm a virgin, and the next my pelvis is bumping into hers as my penis plunges completely inside her. It's such an unbelievable feeling, far surpassing the sensation of the blowjob I experienced the day before. Like yesterday, it's noticeably soft and warm, but I swear it's even warmer inside Linda's vagina than in her mouth. But even more amazing is the tight constricting feeling of her pussy wrapping itself around my cock on all sides, almost as if it's a perfect fit and the two organs were made for each other.

As I'm trying to just take all of this in, I leave my cock fully buried in her for a second and look up at Linda's face in pure astonishment. I'm sure I have a completely awestruck expression, but to my surprise Linda looks pretty amazed as well. Her mouth is hanging open and once she sees me, she kind of sits up a little so she can grab my ass. Then she uses her two hands to clamp onto my cheeks and hold me tightly into her.

She then whispers to me with a genuine look of shock, "You're so big." I can immediately tell that she's not just saying that, and my cock must actually be larger and more noteworthy than I had ever assumed. I know it's superficial, but that makes me feel so good. It also just turns me on even more, and makes me want to start actually pumping, so I pull myself out a little bit, and as I do this I feel Linda's hands gently guide me along the way. Once we get most the way out, we synchronize our efforts and I move back in while she pulls me in by my ass.

Over and over we do this. I'm fucking this woman, and it's incredible. The in-and-out motion is even better than the initial feeling of just being inside her. It's so natural, and it feels like this tremendous release that's been built up inside of me my entire life, waiting for this one moment.

My mind is also unbelievably at ease. It sounds silly, but I've always worried that I would unexpectedly die someday while still being a virgin, and thus end up having never had sex. It's been a legitimate fear of mine that I would miss out on this fundamental experience of being a human being. But now as I pump away, I can confidently retire that fear forever. The other thing I'll never have to worry about again is my brother Tyler. Now if he ever tries to make fun of me for that list of mine he found, I can just laugh it off knowing how ridiculously outdated it is with all of my new accomplishments!

But all of that is secondary, because what matters most is how amazing actually fucking someone is. The sensation is so unbelievably good, and even more astounding is that it looks like Linda is enjoying it every bit as much as I am. She has such an intense look of pleasure and concentration on her face, that it honestly looks like she might be about to orgasm. Is that possible? Could I really make her cum a second time, but this time using just my penis? Holy shit that would be incredible.

Just as I'm contemplating the potential of a second orgasm for Linda, the thought also enters my mind about my own second cumming. I realize just how good having sex right now actually feels, and that I have to make sure I prolong this as long as possible. But with each subsequent thrust in and out of Linda's wonderful pussy, that familiar tingle in my penis gets stronger and more apparent, letting me know I probably only have a few precious seconds until I cross that point of no return, yet again. Fuck, I don't want that to happen. Not yet at least.

So in order to prevent my orgasm, I decide I have no choice but to slam on the brakes. I halt my pumping immediately and lift myself up so only the very tip of my penis is left inside of Linda. This obviously gets her attention, as she says all panicky, "What is it? What's wrong?"

I take a moment to gather myself and then admit, "I was going to cum again so I had to stop."

Linda clearly is not in agreement here as she gets an almost angry look on her face and says, "No, no, no. That's the worst possible thing you could do. Don't fucking stop!" And then she grabs me and forces me all the way back inside her. "Fuck me! Cum in my pussy! It's fine!" She begs.

Goddamnit, I didn't mean to upset her, I was trying not to disappoint her by cumming too soon, but clearly I made things worse. Fuck. So I do as I'm told and I start fucking her even harder than before. In fact, I lift myself up off the mattress with my arms so I can just piledrive my dick into her with no resistance. And as soon as I start this, I immediately get back on track and go steaming full-speed ahead towards my second orgasm. With my jizz about to start exploding at any moment, I'm struck by the loud half-thumping, half-slapping sound our bodies are making as they forcefully collide together at the crotch. It's both amazing and physically strenuous, all at the same time.

"Ohhhhh. Fuck..." Linda yells, like seriously, a full blown yell that Mark might be able to hear from the basement. I'm slamming her and I start erupting inside her. My body starts convulsing and my powerful, rhythmic, thrusting morphs into a heap of limp spasming as all the cum left in my testicles is expelled into her vagina while my body collapses onto hers. Linda grabs my ass to hold me tight and starts passionately kissing me, as we seemingly both enjoy this incredible experience that I can only describe as making love. At least that's what it feels like to me. I know better than to say it out loud, but god I think I love this woman. I at least know I love this moment.

Finally, I finish cumming and we break our kiss. I feel so relieved and so exhausted, that I am just completely spent, both physically and emotionally. I'm ready to just collapse onto Linda's wonderfully comfortable bed, so I roll off to the side of her and withdraw my penis in the process.

"Woah, woah, woah." She says, seemingly surprised that I moved off of her so quickly. "Shit! Grab me some Kleenex!" She instructs me as she points to a box on their bedside table.

I do as I'm told and grab a handful of tissues and hand them to her. She takes them and quickly covers her pussy, before slowly and thoroughly wiping her entire crotch with them. She then looks at me and says, "You can't just pull out like that without warning. When you do that you're releasing the flood onto the bed."

I feel like an idiot but I honestly had no idea. "I'm sorry, I didn't know." I say.

Linda gestures for a couple more tissues, so I grab three more for her and then she proceeds to climb off the bed and onto the floor while holding the fresh wad of tissues below her vagina. Without saying a word, she waddles over to the bathroom and out of sight. She doesn't bother closing the door though, and a few seconds later I hear the unmistakable sound of a girl peeing into a toilet. It's something I've never experienced in real life before, and is pretty crazy to think about. My curiosity would love for me to get to watch what she's doing right now, but being in bed and worried I've already annoyed her enough, I settle for just getting to hear this phenomenon.

After the tinkling noise ends, I hear the toilet flush and Linda walks back into the room and crawls into bed next to me. I'm still in awe of the fact that I'm no longer a virgin, but part of me is anxious that I've made a few too many mistakes during this whole process and she's almost certainly disappointed in me.

Once again, it's almost as if she can telepathically see the worry in my brain. "Don't worry too much about cumming so fast." She says, "We'll work on that and it'll get better the more sex you have. I'm sure of it." That's nice of her to say. And then she cracks a smile and says, "I'd rather your performance be short and your cock be long than the other way around." This makes me laugh, and then she concludes, "Because one of those we can work on, but the other we can't."

I love that she thinks I have a big cock. That in itself is crazy to think about, but part of me wonders if it's just because her husband has an abnormally small dick? My curiosity gets the best of me, but I mask it by asking the opposite of what I'm actually wondering, "Does Mark have a large penis?"

Linda chuckles and says, "Definitely not as big as yours..." and then she pauses and continues. "To be honest, you'll probably get to see it soon enough, but it's maybe 5 and a half inches? Maybe a little more?"

What did she just say?!? I'm going to see Mark's penis myself? What did she mean by that and why did she say it so casually?

Before I even have time to get some clarification on what she meant by that, she redirects the conversation. "So what are you looking forward to most during this summer when you'll be working for me?"

I'm still trying to process that comment about Mark's dick, but the question she poses is pretty easy to answer, so I respond, "Honestly, if we just did what we did today... me getting to lick your pussy and then having sex... that would be pretty awesome to do everyday."

This makes Linda smile and she takes her finger and starts rubbing it ever so softly on my bare chest. Then she looks me in the eyes and says, "You are just the sweetest thing, aren't you?" I smile. "I'm sure that would be nice..." And then she pauses, before tapping me on the chest and says, "But... I have a lot of things planned for you this summer. Just you wait and see..."

I'm not going to lie, the way she says this makes me anxious. What does Linda have planned for me? My first thought immediately goes back to yesterday and how she seemed really into my butthole. Does she have things planned for my ass? And then obviously there's the comment just now about her husband's penis. What does she have planned for me and that? It doesn't take a genius to jump to conclusions here, and these are conclusions I have zero interest in exploring this summer.

Damn it. These last 24 hours with Linda in her bedroom have been a roller coaster of emotions, constantly swinging between extreme joy and terrifying anxiety. As soon as I relax and start to get comfortable with my decision to do this whole escapade, she brings something up that really worries me. I want so badly to make her happy and please her, especially since they're paying me money to do this, but at the same time I do have limits on things I know I don't want to do. What am I going to do if they don't respect that? Will she (or they) be understanding if I say no to something?

I continue to lie in bed next to Linda, and maybe she can tell how distraught I am, because she tells me, "Don't you worry about a thing though, we are gonna have so much fun and make each other feel so good all summer long... it's gonna be amazing."

That definitely helps to hear. So much so that I feel at ease enough to close my eyes and just enjoy the sensation of lying in a giant comfy bed having just had sex. To top it off, Linda starts gently running her fingers over my back and it feels so comforting and relaxing. So much so, I actually drift off to sleep and take a nap.

By the time I wake up, Linda has left the room and I'm in bed all alone. I reach for my phone and see it's already past noon. I figure I should probably get dressed as I'll need to have lunch, but when I look down at the floor I don't see my jeans, or my underwear. Weirdly, I do see my shirt and socks though. Since I'm completely naked, I figure my best bet is to just stay in bed.

So I hang out here for 15 or 20 minutes catching up on my phone, and then I finally see Linda poke her head in the door, fully dressed.

"Nice nap?" She asks.

"Yeah, sorry I fell asleep." I apologize.

"Oh darling, don't you worry about it at all. You had a big morning." She says with a laugh. "Oh, I hope you don't mind but I threw your jeans and undies into the wash, and they're drying now so they should be ready shortly."

"Oh wow. You didn't have to do that. Thank you." I say, and all I can think about is how nice and considerate Linda always is. And once again, my roller coaster of emotions takes another turn and I can't help but think how ridiculous it is to be worried about what this summer might entail. She's so consistently nice and thoughtful, I'm sure she wouldn't ever make me do something I didn't want to.

"I bet you're hungry. I'll go grab your lunch from downstairs." She tells me as she turns around and heads out the door.

All afternoon, Linda and I just hangout in bed, me naked, her clothed. We kiss a little bit, but otherwise there's not much sexual activity. We watch a little tv, talk about school and growing up, but most of all we just lounge around and relax together. Multiple times I ask her if I should head on downstairs and do some work for her husband, but each time she tells me that she's in charge and she wants me to stay put. Who am I to argue with that?

While we're watching tv in bed, occasionally she'll flip over to check in on a baseball game. And each time, she seems to be quite pleased with the fact that the Cardinals are winning. However, she mentions that Mark is also watching the same game downstairs, but he's in a sour mood because his Cubs are losing. She tells me it's even more reason for me to stay up here with her in bed. I'm honestly not much of a baseball fan, or even a sports fan, despite the fact that I am a competitive runner. But regardless, I think it's cute that they both enjoy watching baseball, even if they apparently cheer for two different teams.

Eventually, four o'clock rolls around and Linda and I both agree it's probably time for me to head home. She has since brought my freshly cleaned jeans and underwear up from the wash, so I finally get dressed. It baffles my mind that I am getting paid so much money to just sit around all afternoon, and to be honest I can't help but feel a little guilty. But in fairness, I was constantly checking to make sure I didn't need to go downstairs, so what more could I have done?

As I'm getting ready to head home for the weekend, Linda reminds me about what we had discussed earlier. "Now don't forget your homework!" She tells me. "Just make sure you shave every morning before you come here, and no masturbating of any kind... At least not anything that ends in you cumming without me." And then she winks at me.

"Understood." I say with a big smile.

I make yet another mental note of these two requests of hers, and then I also remember what Mark and I had discussed this morning about how important it is I not tell anyone about our new arrangement. So that makes three things I need to keep in mind, but I'm pretty confident I can handle this.

And then as I'm literally walking out the door, Linda catches my attention and adds, "Take it easy this weekend and rest up. You have A LOT to learn next week, and it could get a little intense."

And there's that crippling feeling of anxiety and dread that I just can't seem to shake. Oh god, what the fuck is she going to do to me on Monday?