Barely Paralegal Ch. 03

"Sure!" I answer, with all the willingness of a teacher's pet.

"Ok, so most importantly..." Linda starts in, wasting no time getting this private lesson started. "This... right here..." And then she uses two fingers to protrude the little knob at the top of her pussy, "is my clitoris."

I'm pretty confident I could've pointed that out if there had been a pretest of my knowledge, but I simply nod and respond, "Ok."

"You want to focus all your licking on this." Linda tells me. "I can tell you were excited to lick all over, but it's this. The clit is the key."

"Got it." I confirm, and then I start to move back in to try licking Linda's clit like she told me to, but she stops my head with her hand.

"Easy there. That's just part one. There are three parts here."

"Oh, ok." I say as I retreat my mouth and kind of laugh at my own over exuberance.

"Part two... while you're licking my clit, you should have a finger up in my pussy. Either a middle or index finger should work." She explains to me.

"Ok. Got it." I respond.

"Why don't you give this part a try." She then instructs me.

Will do. So I extend my index finger on my right hand and gently penetrate Linda's vagina. It slides in wonderfully and once again I'm blown away by how warm it feels to be inside her.

"Ok, perfect." She says, before continuing, "Now I want you to rub your finger on the roof of my pussy, almost like you're doing this..." And then she shows me with her own index finger the 'come hither' motion.

So I try to mimic that move while inside Linda, and I can clearly feel my finger rubbing along the roof of her vagina. I do it pretty slowly, but over and over I press up against her upper wall, enjoying the feeling of every slick bump along the way.

"Perfect..." Linda sighs, and for the first time seems to be showing signs that what I'm doing actually feels good.

I keep this up for a few more seconds before Linda gestures for me to remove my finger so she can move on to the next part of her lesson. "Ok, third and final step..." She says, and then she noticeably scoots herself further back on the bed, lifts her legs to be even more spread open, and then uses her elbows on her thighs to force herself to rock back even further. "I want you to use a finger from your other hand, and slide it into my ass."

Uh, what the fuck? I wasn't expecting that. Why does licking pussy have anything to do with her butt? I don't know what to say or do so I basically just stand there.

"Ok let me guide you through it." She says in response to my inaction. "So there's nothing worse than a dry finger in the butt, so first step is to make sure you get it slick. Just use the wetness from my pussy." She instructs me.

I figure I at least understand that part, so I take my index finger on my left hand and I slide it into her vagina, and then rub it around the entrance for good measure until it's noticeably wet with her juices. As I do this, I can't help but stare into her exposed butthole. It looks just like any other butthole, including my own I assume.

I've never been too intrigued by anal sex. Whenever I watch porn, I always find the vagina to be so much more interesting, perhaps because I already have an asshole of my own? I've also never desired to have anything in my own ass, so I feel like it would be hypocritical for me to want to put something in someone else's. But here I was, staring at the butthole of a 50-year-old woman, about to stick my finger in it because that's what she's instructing me to do.

"Alright, now just slide it in gently." She tells me.

So I do. I move my finger to the precipice of her asshole, wiggle it slightly, push forward with not much pressure, and holy shit it slides right in. Weird. It's certainly not the worst feeling to be fingering Linda's butt, but it's clearly a different feeling that fingering her pussy. It's super tight and constricting, as if her colon is shrink wrapped around my index finger.

"Ahhhhh... there we go." Linda says softly, seemingly enjoying the finger. She kind of adjusts her position on the bed to get more comfortable while my left index finger remains in her ass, and then says, "Ok, now it's time to add in the other two parts and get to work."

Holy shit, I'm ready. I reposition my other hand to get that finger inside her pussy, and then I move my face in so my mouth lines right up with her clit. And then I start licking, and I start fingering. There's a lot going on, but this is fucking cool as shit.

I actually kind of like licking her clit. The one downside is it doesn't have any of the tangy flavor I was getting from her actual hole, but playing with this nub with my tongue is quite enjoyable. So I keep doing all three things here and then it really hits me, holy shit, I'm eating out Linda's pussy. Like for real. And not only am I getting to do this, but she's teaching me to make sure I get good at it! And then I start wondering if perhaps I'll end up making her cum by doing this? Oh god I can only hope, as that would be so incredible.

She's far enough back on the bed that I have to lean pretty far into her. As a result, even though I'm still fully clothed and in my jeans, my cock is pressed against the footboard on their bed. It actually doesn't feel too bad though as it's providing a little bit of stimulation of my own. But my torso is fully up on the mattress, resting on my elbows to give me enough stability to keep stimulating her exactly like she told me to.

And I keep working away diligently. I'm licking and fingering and even though it's a little tough to keep both hands in position at the right angle, I'm able to make it work. Perhaps the weirdest thing of all is how I can actually feel my two fingers kind of rubbing against one another inside Linda. It's like the only thing separating my finger in her ass and the one in her pussy is a soft membrane that is shockingly thin. It's fucking nuts.

I start to hear soft moans and other subtle signs that Linda is really enjoying what I'm doing to her. That makes me feel so good and just amps up my effort level even more. At one point though, I think get a little too aggressive as she reaches down and taps me on the shoulder and says, "Not so much on the in-and-out in my ass... just leave that one in."

"Oh sorry." I pull my mouth away from her clit to apologize.

So I push my finger in her ass all the way up to the knuckle, and try to just leave it there, pressing firmly, but not moving.

"Ahh... perfect." She sighs with pleasure, which gives me a tremendous sense of my own euphoria.

I then refocus my attention back on the finger in her vagina, as I continue to rub the top of her canal over and over again. And while all that is going on, I'm still going to town on her clitoris, making circle after circle with my tongue. Linda seems to really be enjoying the job I'm doing.

"Oh honey... don't stop... keep going like this and you're gonna make me cum." She tells me.

Holy fuck. It's happening. Oh my god, this is so amazing and exciting and I can't believe this is actually happening. I lean in even further, putting more pressure on all three points of contact. I want this so bad. I need to make her cum.

And then it hits me. Oh fuck no! I'm so engrossed with Linda's orgasm that I totally forgot about my own, and now it's too late. I feel that tingle in my cock I've felt countless times before and I suddenly realize I'm about to cum. Not her, but me. And it's already too late to stop it. I have a split second of indecision and panic that hits me, but I quickly realize that what's done is done and I just need to keep licking and fingering away. But there's no doubt a wave of dread washes over me as I realize I'm seconds away from pathetically cumming in my jeans pressed against the foot of Linda's bed.

"Oh I think I'm gonna cum." I hear Linda say softly, I'm sure without the faintest idea that I was about to do the same. And so as I keep licking and fingering her as if everything is normal, my own orgasm commences. I start filling my boxers with semen while instinctively thrusting my hips subtly against her bed. I'm terrified to give off any sign of my orgasm, but I just can't help myself from quietly humping away. I continue to spew cum uncontrollably into my underwear, and I can feel the mess collecting, but at least Linda has no idea what's happening on my end. As amazing as it is to be eating pussy right now, there's no doubt this is one of the worst orgasms of my life, because I'm simply mortified it's happening.

As soon as I'm finally done jizzing in my pants, my mindset immediate starts to turn around though, as I hear Linda tell me, "Here it comes..." and then she takes a big inhale.

Now normally, once I have an orgasm, my interest in anything sexual immediately falls off a cliff. If I'm looking at porn online for example, I can't close my browser fast enough once my last drop is out. But in this case, it's totally different. Any post-orgasmic letdown I might normally have is no match for the astonishing fact that I'm eating pussy and about to make a woman cum.

Ironically, the fact that I orgasmed seems to clear my head and take my focus to an entirely new level, to where I'm even more aware and in control of what's unfolding in front of me. I have all three points of stimulation working like a well-oiled machine, and sure enough, Linda starts orgasming.

"Oh yes..." Linda moans as she grabs my head with both hands. "I'm cumming... I'm cumming... Don't stop..."

I'm so happy I almost forget about the embarrassing mess in my pants right now. I don't let up on my assignment either, as I figure I'll keep licking and fingering away until she tells me to stop. Linda continues to moan as she cums, and I swear I can actually feel her vagina pulsating around my hand. With my mouth still up on her clitoris, I can't see what's going on down below, but I'm so curious if any extra liquid has started coming out of her during her orgasm. Is that a thing? I've seen porn movies where the girls squirt a ton, but do normal girls do that too? There's so much I want to know about real female orgasms, especially now that I've actually achieved one.

Eventually, Linda's moans and convulsions subside and she releases my head from her hands. Her arms drop to her side and while I don't know much about what just happened, I know enough to tell she's done. So I pull my head away from her pussy and then slowly slide my index fingers out of her two holes. They're both wet and saturated with moisture, and I can't help but take a sniff from each. The pussy one smells as expected, but the ass finger smells surprisingly similar to the first as well, with maybe just a small hint of butt smell. I figure there's no need to lick either one so I turn my attention back to the most pressing issue of all, the jizz in my pants.

I look down at my jeans to assess the damage, and to my surprise I think there's only one tiny, dark, wet spot visible. Clearly I'm lucky to be wearing jeans, as I'm sure any softer material would be showing the wetness much more apparently. Maybe if I can stay dressed, I can make my way to the bathroom and clean up without Linda finding out?

"That felt soooooo good." Linda says, startling me as I look down at my jeans. "You're a very quick learner." She says with a smile.

I look up and bashfully say, "Thanks."

Linda then takes my hand and says, "Come here." as she gives me a gentle pull.

"Oh, I'm ok. I don't need to climb up there." I politely tell her.

This seems to catch Linda by surprise, as she gives me a weird look, tugs my arm a little harder and says, "I'm not asking you, I'm telling you as your boss." But she does say it with a big smile that makes it seem like she's just being playful.

I figure I don't have much of a choice though, so I quickly pop my shoes off and climb on up, otherwise fully clothed. And as soon as I get up there, Linda crawls over towards me and immediately reaches for and unbuckles my belt. Fuck. For a split second I contemplate making up some excuse to just up and leave, but I realize how fucking crazy that would seem. So I accept that I have no choice but to face the music on this one. God I'm such an idiot.

Linda gets my belt loose, and then unbuttons my jeans. Even though it's right in front of her face, I don't think she even notices that small spot of semen showing. But all that does is delay the inevitable, as she wastes no time in unzipping my jeans and pulling them down. She clearly wants my penis, which under normal circumstances would be amazing.

And sure enough, as soon as she pulls my jeans down to my thighs, she and I can both see the enormous dark spot in my boxers standing out against the otherwise light gray material. She doesn't say anything right at first, but instead just stares at it, furrows her brow, and then reaches out to touch it and confirms it's a huge wet spot.

Then finally, she looks up and me and says genuinely confused, "Did you cum in your pants?"

Ugh. I feel the embarrassment deep within the pit of my stomach. I can't think of anything else to say, so I just apologize. "I'm so sorry. I didn't mean to."

Linda still looks baffled. "When? When did you cum?" She asks.

"While I was licking you." I answer.

"Wait." She then says, clearly still trying to figure out what happened. "So you weren't even touching yourself? I mean how could you, both your hands were busy with me. Right?"

I guess this makes me seem even more pathetic, but I confirm that's what happened. "Yeah, it was when I was licking and fingering you and right when you told me you might cum. I didn't even realize that I might cum too until it was too late."

Linda just stares at me blankly, not saying a word. And then finally, her straight face starts ever so slowly turning into a grin. And then finally, she says, "Holy shit. You are just the sweetest, horniest, little thing, aren't you?" So I guess she's at least not upset with me? And then she goes on, "Talk about one hell of a compliment. The taste of my pussy made you cum without anyone touching your cock. That's simply incredible."

She's downright effusive right now, which definitely makes me feel better as I was paranoid she'd be upset and annoyed. Still, I feel like I need to confirm that this is really happening, so I ask her, "So you're not upset?"

"Oh sweetie, god no. I LOVE your innocence. And this is just too perfect to describe." And as Linda says this, she resumes removing my jeans and quickly gets them down and off my legs. Next, she quickly dispatches my socks before reaching up and pulling down my cum-soaked boxers. As she takes my underwear off, she exposes my tired, semi-limp cock that's still covered in a shine of semen. But before she can even focus any attention on my spent penis, she takes my boxers and turns them inside-out in front of both of us. She's now clearly showing the source of the gigantic wet spot as there's a noticeable layer of white jizz residing on the inside of my underwear. And then without warning, she lifts it up to her face and starts sucking as much of the cum out of my boxers and into her mouth as she can. Holy fuck, this woman is insane.

I mean I totally get it, as just a few moments ago I was relishing in the chance to taste all of her juices, and now here she's feeling the same way about mine. But it's still surreal to think about someone actually wanting to consume MY fluids, and then to see it in person. Oh my god, not only is she eating my semen but she's looking me straight in the eye as she does it.

Soon enough, she's content with how clean she's gotten my boxers, because she tosses them aside and starts making her way over to me on their king-sized bed. When she reaches me, she immediately lifts my shirt off so now I'm just as naked as she is, and for the first time ever we're both completely naked at the same time.

She pulls me down onto the bed and we fall into an embrace on the mattress and start making out. It's pretty incredible. We're basically full-body hugging while naked, and I can feel her soft, huge tits pressed up against me, and her smooth thighs wrapped around me. Considering I just blew my load roughly five minutes ago, I'm not very hard, but having our bare genitals pressed close to each other starts to get the blood flowing back to my cock for sure. We're lying there passionately kissing, moments after we both just orgasmed, and everything feels so amazingly comfortable. Her bed, her arms and legs around me, our tongues in each other's mouths, and most of all our naked bodies pressed up against each other. All of it is simply perfect.

As apprehensive as I initially was about all of this, the way Linda has made me feel ok with who I am, whether it's my skinny body, or my lack of sexual knowledge, or my embarrassing moment of premature ejaculation, she's been so accepting and complimentary, it makes me feel amazing. And on top of that, I was able to give her an orgasm! God, I'm so glad I agreed to all of this.

Eventually, my moment of self reflection is paused when Linda pulls away and switches from kissing to just looking at me and stroking my hair.

"How're you doing?" She asks.

"I'm great." I answer with a smile.

"Good." She responds. And then she runs her hand over the stubble on my face and says, "So what's the story with this? Are you trying to grow a beard?"

The truth is I couldn't even grow a beard if I wanted to. In fact, I only need to shave like twice a week because my facial hair is so pathetic. So I tell her, "Oh sorry, no, I just need to shave."

"Yeah, it seems like it." Linda says, and then she adds, "I want you to shave every morning before you come to work. Understand?"

It's a little weird how she just phrased it as a demand and not a request, but it seems reasonable. I guess she wants my face to always be smooth? Maybe it makes a big difference when I'm eating her out. I definitely don't want to do anything that would inhibit my ability to go down on her.

"Ok. Yeah I can do that." I confirm.

"Good." Linda says. And then she continues, "And one other rule." At this point I'm a little nervous with this somewhat aggressive turn in her requests, but I'll hear her out. She then says, "No jerking off at home. I need you to save all your cum for me."

This request seems a little more extreme. My first thought is how would Linda even know if I DID jerk off? Can she tell how long it's been when I cum? Maybe she can and that's a thing. But either way, I guess this request is reasonable. I mean if I'm getting off while I'm here, I probably won't have any need to jerk off at home. But even so, why is she being so demanding all of the sudden? As great as I was feeling just a few seconds ago, now I'm starting to feel anxious again. I figure I should at least tell her what she wants to hear though.

"Ok, I can do that." I respond.

"Excellent." She says. And then Linda pulls me up and on top of her so I'm lying on her instead of the bed. My weight is now pressing down on her, at least as much as my skinny 150 lb. frame can do. Her naked tits are right in front of me, but even more amazing is the fact that my cock is mere inches away from her pussy right now. This must not have been lost on Linda either, as she then says to me with our faces pressed together, "So, do you think you have enough left to fuck me?"

There's no doubt that I do, because as soon as I hear Linda ask that, my semi-hard that is currently pinned against her abdomen perks up to become a full-blown boner again. As amazing as eating her pussy was, it's only ever been one half of my dream sexual scenario, so I'm certainly not going to miss out on a chance to accomplish the whole shebang. This all may be happening ridiculously fast, but I'm done being a virgin.

"Definitely." I answer.