Jacobson's Mom Pt. 03

Jacobson's Mom * Part 3 of 3

My assignment is clear. I need to recreate this scene for Jake as best I can, so he has the chance to live out his ultimate fantasy. I'm realizing though that I probably should've gathered more information from this 18-year-old virgin before I sent him out into the hallway completely naked, because there are a lot of details I'm still pretty hazy on. It's fine though, as I think I have enough to go off of, as I already have a general sense of what he and his mom are like.

Anyway, here's what I do know. I know Jake would peer through the crack of his mother's bedroom, and watch her masturbate with a vibrator. He would stand there and spy on her, while she would bring herself to orgasm, and then he'd retreat back to his own bedroom once she was done. So that's what we're going to try and recreate here, with the obvious caveat being that I'm expecting our version to have a different ending.

The good news is, not only do I know the specific toy that Jake's mom would use on herself, but as luck would have it, I actually own the exact same vibrator! So that part is easy.

One thing I don't know, because I never asked, is what his mom would typically wear while doing this. From the bits and pieces Jake's told me about her, I find it hard to believe that she'd wear a thong to bed, like I currently have on. Jake has mentioned that his mom never seemed to date, so I'm going to go out on a limb and assume her typical choice of underwear is probably more practical than sexy. Which is fine, as I have a simple pair of white cotton undies I can easily change into.

As I start undressing in my closet, with Jake still patiently waiting out in the hallway like a child doing a timeout, I start thinking about what else I should wear. Maybe I should put on like a simple, oversized t-shirt? That seems like something comfortable for Jake's mom to sleep in night after night, so that's probably appropriate. Okay, so I think I'll go with those two pieces of clothing, cotton undies and a t-shirt. No bra.

Now you're probably wondering why I'm stressing so much over these seemingly minor details, but it's simple. I want to make this scene as hot as possible for Jake. He confided in me such a personal thing, that he has sexual feelings towards his own mother, and while it was quite shocking to hear that initially, I've come to realize that his act of confessing is definitely a huge turn on for me. I love that I know his deepest, darkest, secrets. And in some weird way, it's almost like I want to reward him for telling me them.

I kind of also like the challenge of it. I like trying to recreate a scene that is true and representative of how he and his mom actually interact with one another, while also making it as hot as possible for Jake. The trouble is, without much information, I'm going to have to improvise a lot of it. But the good news is, Jake seems to be pretty satisfied with how our roleplay has gone thus far, so I think I'm doing something right!

Okay, it's time to finish getting ready here. I already picked out the perfect t-shirt, as the baggiest shirt I own also happens to be one I got as a Mother's Day present many years ago from my own son, that says "Let's Taco 'Bout How Great a Mom You Are" with a picture of a giant cartoon taco. I figure it's an appropriate thing to wear given our mother-son roleplay, despite it being corny as shit. Ha, that in itself was a pun, given the corn shell on the taco! : P

Anyhoo, the only thing left to change is my underwear. But as I take down the black thong I had put on earlier tonight when I had been dressing to impress, I can't help but notice how much of a flood zone it is down there. Holy shit.

I honestly can't remember the last time I was this wet! I'm sure it's the result of everything that's gone on over the past hour with Jake. From the initial premature ejaculation incident, to the bath, to all the licking and fingering of his tight, little sexy 18-year-old asshole, to finally getting the chance to engulf that undersized, but engorged penis of his. I think this whole time I've been getting more and more turned on, and now I'm simply overflowing with desire, both literally and figuratively.

As I remove my underwear, I can even see the trail of my own cum stretch along with it as I pull the garment down. At first, I think about giving myself a thorough wipe, just so I can start anew with the clean pair of cotton undies, but then I reconsider. I actually think it's a good thing for Jake to see his mom as wet as possibly, so instead I carefully swap out my underwear while retaining as much of my natural lubrication as I can. I definitely think that's the way to go.

Alright, let's do this!

As I climb up onto my bed, for a moment I contemplate about whether it would be more accurate for me to be under or over the covers, you know to be true to how Jake's mom would actually masturbate. But then I realize there's probably a limit as to how important these minor details are, so I'm just not going to worry about it. In other words, I'm going to settle in on top of the covers, and I'm also going to leave the lights on, because I just want Jake to be able to see as much of me as possible.

So I get myself into position. I lie my head back onto my pillow, pull my taco t-shirt up just enough, and then I raise my knees and spread my legs open. And then for the final piece of the puzzle, I pick up my trusty, white vibrator and get it ready to go.

Now one other difference between this scene and the one Jake described from his own house, is that my bed is oriented differently in relation to the door. Jake had talked about how his mom would leave her door open just a crack, but that he was able to watch her through that space. With my bedroom, that's simply not possible. It seems like Jake has already realized this, as he left my door completely open when he went out into the hallway. But again, who really cares if it's not 100% accurate.

Speaking of Jake in the hallway though, I actually can't see him despite the door being wide open, and I also haven't heard a peep out of him, either. I have to assume he's still out there though, right? Standing there all naked, nervous and excited, with his tiny, little penis hanging out, probably still a little droopy from coming twice tonight already!

It would be kind of funny though if he just panicked, had second thoughts, and got the fuck out of here while I was busy changing. I'm guessing that didn't happen though. : P

Actually, scratch that. I'm pretty damn sure he didn't leave because all of his cum-covered clothes are still in my washing machine! Ha. Nevermind. But that reminds me, I probably should move those over to the dryer at some point, but I'm definitely not bothering with that right now.

Okay, it's go time. With my legs still spread, I slowly turn the bottom of the vibrator until I feel the battery-powered device come to life. I actually don't crank it up all the way, but I turn in on just enough to where I'm confident Jake will be able to hear it from the hallway. And so after taking one last glance at my open doorway, I exhale loudly, close my eyes and place the whirring phallic-shaped device directly onto the cotton fabric covering my clit.

Ohhhh, fuck this feels good. In fact, this is amazing. Holy shit, did I need this! I mean seriously, I probably need to come up with a different plan here, because I'm going to orgasm in a matter of seconds if I keep this vibrator pressed against my clit like this. And as great as that would feel in the moment, I definitely don't want to come just yet.

So I actually take my vibrator and move it away from my vagina and instead start slowly tracing it up and down my thighs. As I do this, my curiosity gets the best of me and I open my eyes ever so slightly to see if young Jacob has appeared at my door, yet. But to my surprise, he hasn't.

I feel like I need to know when he finally does show up, so you know what I do? I do that thing where you squint your eyes and leave them open just the tiniest amount where you can sort of see out between your eyelashes, but it still looks like your eyes are closed to someone else.

And then I move my vibrator back to my clit, and it feels fucking amazing, so I move it away again. Rinse, repeat, I do this a few times.

Still no sign of Jake, though. Fuck it, maybe for some reason he can't hear the device, so I'm cranking this baby all the way up. Doing this does make it noticeably louder, but it also makes the vibrations almost too intense, so now I'm no longer touching myself with it at all, and instead just kind of holding it above my crotch.

And then through my squinted eyes, I see it. Finally! Jake's head is ever so slightly popping out from behind the right side of the door frame, and he looks so fucking adorable.

Ha, I wonder if he really couldn't hear the vibrator at first, and cranking it up is what did it? It's like the bat signal wasn't initially bright enough I guess. : P

Well, who cares, because Batman is here now! Although, to be honest, Jake is definitely more of a Robin than a Dark Knight, ha, but that's okay.

I mean, sometimes you want to get wined, dined, and sixty-nined by a dapper Bruce Wayne. And that can be great and all. But other times, it can be appealing to be the one in charge. You know, where you find your own little Robin, and not only do you get to take his virginity and own it forever, but you get to show that shy Boy Wonder a world of pleasure that he never even knew existed. And if you do that, you can be confident that he's going to remember you for the rest of his life, which is an amazing thing to think about.

You know what's less amazing? Jake just standing there peeking out from the behind the doorway. Why won't he just come in? I don't want to have to call him in. I want him to creep up on me while I pretend my eyes are still closed, and then I'm going to open them up and act all surprised that he's standing there right in front of me. Is that too much to ask?

On top of that, I'm kind of losing interest in this vibrator. I'm still at the point where holding it against my clitoris is too much stimulation, but running it along my thigh is not enough. You know what I want? I want his warm mouth wrapped around my clit, not some cold, hard piece of plastic pressed into it. Come on, Jake, get the fuck in here already!

I will tell you one thing though, even through my squinted eyes, it's notable how small and cute Jake appears out there in the hallway. It's just his head poking out, as that's the only part of him I can see, but he looks so short! Maybe he's leaning over though?

I wonder if he's still limp from his second coming, or if there's any possibility he's already got a new boner? Not that I would be able to see it though, as it's hard enough to see while pretending to have my eyes closed, but also because his itty bitty dick probably isn't long enough to poke out from behind the doorway, ha.

I kid, I kid. I actually really love the fact he has such a small penis. I'm sure part of it is the novelty, in that it's interesting to get to see and feel a pecker that size for the first time. And then there's also the innocence and youth aspect, where his small cock just makes him seem even younger than he already is. But you add it all up, and it's definitely not a negative. And I say this even with the expectation that sex with him probably isn't going to be as fulfilling, but I'm okay with that.

I just really wish Jake would stop hiding and get his ass In here! I know, maybe I need to ham it up a little. Like make some noise myself? I can do that.

I take my vibrator that's still running on full blast, and I move it down towards my vagina, and then I press it into my underwear, forcing the fabric against where my opening would be. It feels nice, perhaps even better than when I was stimulating my clit, and I let out a small moan of satisfaction.

Holy shit, am I still so ridiculously wet. In pressing the toy against my underwear, I can feel it sliding around like an oil slick, and I'm sure my cotton undies must be showing visible signs of all this wetness, too. I wonder if Jake can see that from where he is? I hope he can, just so he can know how much he's turning me on.

Woah, maybe that did the trick, because here he comes! Jake just took a step out and is now standing right in the middle of my bedroom doorway.

Me (pressing my vibrator even harder into my underwear): "Oooooooooohhhhhhhhhh."

I think this is working. Now Jake is slowly walking towards me. He's being very quiet as he approaches, though.

Me (as I move the sex toy back up to my clitoris): "Oh my god..."

Jake continues to tiptoe forward until coming to a stop about three feet in front of the bed. Okay, it's time to open my eyes.

Me (after immediately locking eyes with Jake): "Oh Jacobson, what took you so long??"

Jake (standing there completely naked, and holy shit, he actually does have a hard-on): "Sorry Mom... I just... I just wanted to watch you for a bit, first."

I'm not going to lie, that question I just asked was purposefully misleading.

Me (as my vibrator continues to whir against my pussy): "No, that's not what I meant."

As expected, Jake looks confused.

Me (as I spread my legs wider, while moving the toy to the side to give Jake an even better view of my soaking wet undies): "What I meant was, why did it take you so many nights of watching, until you finally walked in here?"

Now obviously, the answer is because all those other nights were real life with his actual mother, and this is all pretend with a woman he knows already wants to have sex with him. But what I'm actually attempting to do here, is point out something that I'm 90% sure is true. That his mom has been aware this whole time that he's been spying on her.

Jake (staying in character without missing a beat): "You've known that I've been watching you??"

Me (still staring right into Jake's eyes): "Of course I've known, Honey Bear. I'm your mom. I've always known you were there, peeking through that crack. I didn't want to make it obvious that I knew you were there, but I've always loved seeing your cute little face staring in at me."

Jake looks quite stunned. I can only assume he's contemplating whether his actual mom knows he's been spying on her, and the ramifications of what that means.

Me (I'm obviously going to keep going with this): "And as much as I always enjoyed having you watch me from afar, I wanted so badly for you to open that door and come on in. It was like every time I saw you appear, I was hoping and praying that would be the night where you'd finally get the courage to come on in... and see up close... exactly what your mom was doing to herself."

Jake (looking sad almost?): "Oh Mom..."

Me: "Yes, Honey?"

Jake (very apologetically): "I'm so sorry, Mom. I wanted to so badly. I swear I did. I've always wanted to come in. I'm so, so sorry."

Aw, poor guy. I'm not actually trying to make him feel bad!

Me (as I turn the vibrator off and place it next to me on the bed): "It's okay, Jacobson. It's okay, Honey. Don't feel bad. All that matters is you're here now."

And then I give him a huge smile.

I want to reach out and touch Jake to comfort him, but I'm kind of stuck with my legs spread open and I don't really want to get out of this position, as I kind of like how I'm presenting my vagina to him, even if it's covered.

In fact, I see Jake is now looking right down at my pussy. He must be able to see how wet I am. How wet he's made me.

Jake (speaking softly, but with an intense look on his face): "Oh my god, Mom."

Me (sweetly): "What is it, Honey Bear?"

Jake (seeming hesitant): "It's... it's... it's that smell. It's so strong."

Ha. Just what every woman wants to hear. It's obvious what Jake is referring to though, as I too am getting more than a whiff of my vagina, and I'm not even directly in front of it like he is. Interestingly enough, I can't actually tell from his expression whether Jake thinks my aroma is a good thing or a bad thing.

Me (figuring I might as well be up front): "That's my vagina you're smelling, Hon. Is it okay?"

Jake slowly nods.

Me: "Do you like the way it smells?"

I have to keep in mind that while we're obviously in the middle of this whole elaborate roleplay, I'm pretty sure Jake has never seen any sort of female anatomy in real life before, well at least not up close, so this is probably the first time this boy has ever been exposed to the smell of pussy. That's kind of hot to think about.

Jake (nodding again): "I do. And it... it... it smells so familiar too."

Ha. Is he going to make a joke about how since I'm supposed to be his mom, then that means 18 years ago he came out of this vagina and now he's remembering what it smells like? Obviously that's ridiculous, but I wonder if that's where he's going with this.

Me (genuinely curious): "What does it remind you of, Honey Bear?"

Jake doesn't immediately answer.

Jake (seeming timid again): "Can I confess something to you?"

I have to say I love this trend of Jake confessing various things. Every time he asks that, I'm so excited to hear what he's about to say next.

Me (trying to downplay my excitement): "Of course, Hon."

Jake: "Your vagina... it smells so much like your underwear always does."

Well, well, well... isn't this interesting.

Jake: "I know that seems obvious, like why wouldn't it. But it really, really does."

Okay, so the take away here is that Jake has a habit of going through his mom's underwear drawer?

Jake (very apologetically): "I'm so sorry about this. But whenever you would leave the house, I couldn't help myself and I'd often go through your laundry."

Ah, even more interesting.

Me (this is kind of hot): "And you'd be looking for my dirty underwear?"

Jake (looking like a guilty puppy dog right now): "Yeah."

I've heard that supposedly a lot of vaginas do smell similarly, so I guess it's not unreasonable that mine really would remind him of his mom's.

Either way, I need to know more!

Me: "And what would you do with my undies once you found them?"

Jake (after a pronounced swallow): "I would smell them. And I would hold them to my face. And I would lick them. And then I would suck on them."

Me (I'm not sure if it's even possible, but I think this is making me even wetter): "Did you like the way they tasted?"

Jake (nods): "I did. And sometimes I would find little bits of residue. Like a dried, crusty white layer that would be on the inside of the crotch. And I would scrap it with my fingernail to loosen it."

Wow. This is quite graphic, and kind of gross. But I love it. I love the shamelessness of it all. And I love the fact that there's no way he's making this up.

Jake (continuing): "And then I would lift the underwear up to my mouth and I would push the flaky, little, white crusty bits onto my tongue. And I would suck on them. And they would melt in my mouth."

Me (wow, this keeps getting more and more explicit): "So what you're saying Jacobson, is that you would secretly raid my dirty underwear, so that you could eat the dried secretions from my vagina? You really would do that?"

Jake (still looking genuinely remorseful): "I would. I'm so sorry, Mom. I'm so weird, and gross, and pathetic. I don't know why I did that."

I know why he did it. And he really is all three of those things he just listed, but that's what I love about this.

Me: "It's okay, Honey. I'm not mad. I'm not mad at all."

Me (looking down at my own crotch): "Would you like to take off the underwear I'm wearing right now? And would you like to put them in your mouth, so you could taste all of my secretions... while they're still wet?

Jake nods again, but more emphatically than before.

Me (this is all so fucking hot): "Because I would love to watch you suck on them... to see how happy it makes you."

Me (as Jake doesn't immediately respond): "Well... what're you waiting for?"

Jake (still looking subdued, but I can sense some combination of nervousness and excitement): "Oh, sorry."

After apologizing, Jake kneels down at the front of my bed, which results in his face ending up mere inches away from my soaking wet crotch. He gingerly slides his fingers under the elastic band at my waist, and then starts to slowly remove my underwear. And as he pulls them up my thighs, I can see, hear, and even feel the intensity of his breathing pick up, as his warm breath is noticeable on the inside of my legs.

Once he slides the underwear completely off of my feet, Jake then takes my damp, white cotton undies and slowly moves them towards his mouth. But the interesting thing is, even after all this discussion about his mom's dirty underwear and how much he loved sucking on them, the wet piece of clothing currently balled up in his hand, almost seems like an afterthought.

And that's because this cute, little 18-year-old virgin is staring daggers at my now completely exposed, wide open pussy. I still have on my ridiculous taco t-shirt, but that's the only thing I'm wearing right now, and it's safe to say that Jake is enjoying the view of me being completely bottomless. And with how captivated he looks, It's also pretty obvious he's never seen a vagina in real life before. I fucking love this moment!

And with his eyes still glued to my vulva, Jake makes a half-hearted attempt to open his mouth and take a symbolic bite of my undies, but it's clear that both he and I have already lost interest in this storyline.

Me (staring at Jake, while Jake stares at my vagina): "Honey... would you rather suck on my pussy itself, instead of on my underwear?"

Jake doesn't bother answering, but instead just casually drops my undies to the floor, takes ahold of my legs, and dives right in. He comes in with the widest tongue I've ever seen and just starts licking, from bottom to top. It's unlike any time I've ever been eaten out before, because it's almost as if it's non-sexual. You see, normally when a guy goes down on me, there's clearly an element of him trying to make me feel good. But this is nothing like that.

Instead, this appears to be more about Jake trying to consume me, to devour my vagina, and to get every last drop of my juices into his mouth, as if his life depends on it. And ironically, even though he's totally focused on what he wants to do, and even though he's not making any contact with my clitoris, it's still somehow the hottest instance of oral sex I've ever received.

Picture Jake, on a sunny, 95 degree summer day, holding the most top heavy ice cream cone imaginable, that is dripping on all sides. And then picture the race against time he's facing, in order to frantically lick that cone before it melts. That's how he's licking me right now, with that sort of gusto, with that sort of urgency, like a boy eating ice cream, and I fucking love it.

He's also focusing so much on my vaginal opening, as opposed to my clit, as obviously that's where all of my wetness is coming from. In fact, I wonder if he even knows what a clitoris is? Either way, it's so unusual to get eaten out this way, but like I said before, it's incredible.

Me (as I take my right hand and run my fingers through his curly, light brown hair): "Oh, Honey Bear. This feels soooooooo good."

Jake doesn't respond or look up, but instead he just keeps on licking. My god, imagine me, as someone who went through so many years of having a husband who never wanted to go down on me, how amazing this must be. And it's not just the physical sensation of being licked, but it's also the satisfaction and self-assurance that comes with seeing someone enjoy the taste of my vagina this much. It makes me feel so sexy, and so beautiful.

But let's be honest, it also feels pretty damn good physically. But as satisfying as this is, I'm sure it could feel even better, so if this kid doesn't yet know what a clitoris is, then I think I'm the perfect person to show him.

So I take my left hand, and I add it to the other side of Jake's head, and I use both hands to not so subtly pull my young lover's head up a few inches. I think I'm a little too forceful though, as Jake's face ends up above my mound, and he gives me the biggest grin, from ear to ear.

Jake (with a sheen of pussy juice glistening all over his face): "Am I doing a good job?"

Me (quietly): "Oh Honey, you're doing a great job."

And then I immediately force his face back down to my pussy, but I make sure to line his mouth up with my clit. I'm mostly successful with my alignment, as Jake resumes his big, wide licks, but this time it's directly on my little button.

Me (giving him some encouragement): "There we go..."

While this does feel good, and we're getting closer, it's still not quite perfect. And while I probably could give him some sort of verbal instruction, I instead try to just force the result I'm looking for. So I push through his curly hair and take a firm grip onto his head, and then I shove his face down into me. This forces Jake to switch from his initial licking technique, to more of a sucking sensation that gives me the constant pressure on my clit that I was desperately looking for.

Me (rather loudly): "Oooooooohhhhhh my god, yes. Ooohhhh... keep doing that..."

Holy shit, now this feels incredible! And I needed this so badly, after all the buildup from earlier tonight. But fuck, I think we might already be at the point of having too much of a good thing. Because if he keeps doing this, I'm going to come, and I don't want to orgasm just yet. Later on I definitely do, but not now!

Me (as I use my two handfuls of Jake's hair to forcefully remove his head from my clit): "Oh Honey, give me one second here..."

While Jake hovers just above my vagina, he makes eye contact with me again, but doesn't say a word. Fuck, he looks so adorable. And I love the fact that he's doing whatever I say right now! Okay, time for a little more sucking.

I push Jake's head back down into my vagina, and he seems to have learned what I like as his mouth heads straight for my clit again. This time though, in addition to his lips pressing against the top of my vagina, I can also feel his tongue running circles around my magical little button.

Me (even louder now): "Ohhhh... fuck yesssss..."

Once again, this feels incredible, but once again, I'm already getting too close to coming. I'm sure you're like, but why don't you want to come? And the answer is, that's just how I am. Maybe I'm weird, but the reason I don't want to orgasm just yet is because I need his cock inside of me first, and we still haven't done that. All the best orgasms I've ever had in my life have come from a combination of fucking and clitoral stimulation at the same time, and tonight deserves nothing but the best, so that's what I want to do.

And on that note, I do think it's time to get on with the fucking. So I lurch forward, and I pick petite, little virgin Jake up by his armpits, and I pull him onto the bed with me.

Me (almost angrily): "Get the fuck on the bed!!"

Jake looks completely shocked, and to be honest a little scared, but I just find that humorous.

Once he's fully up onto the mattress, I force him down onto his back, and I take aim at his little, rock hard three-and-a-half inch boner that's once again sticking straight up into the air. I have to hand to Jake, as while he certainly doesn't have the biggest cock, or even an averaged sized one at that, holy shit can this kid maintain his erections. I mean, not only has he spent the majority of this night stiff as a board, but he barely even needs any time after coming to get hard again! It's seriously impressive.

But for all the boners this adorable, little 18-year-old has had in his lifetime, I imagine this one is going to be unlike any before it. And that's because for the first time ever, Jake's tiny pecker is going to end up where's it's always wanted to go, inside a warm, wet, pussy.

And as they say, there's no time like the present, so with Jake now lying flat on his back, and his eyes looking up at me with great anticipation, I climb up over him, straddle his waist, and then use my right hand to guide his small, hard cock into my desperately awaiting vagina.

Me (as Jake's penis slides in so fucking easily): "Ohhhhhhh... there we go... fuck... I needed this... oh I needed this so badly."

Holy shit, it really does feel incredible to finally be fucking this boy, and truth be told, his cock feels great. Who would've known, but his three and a half inches are doing the job just fine!

Ha, look at Jake's eyes! He's so fucking cute, and his eyes look like they're going to pop out of his head. And his mouth! His jaw is extended out, and he's breathing so hard that I can see his chest moving up and down.

I lean forward and really start to grind on young Jacob's midsection, and it feels oh so good. And now Jake puts his hands on my hips, as he gently slides them underneath my dumb oversized taco shirt that I probably should just take off at this point. But I'll do that in a second, as I really want to focus on how good it feels to rub my clit against this boy's plentiful pubes.

Me (as I gather my wits enough to form a coherent sentence): "How does it feel... to no longer be a virgin?"

Jake (with a slightly less serious and more relaxed look on his face as compared to when I first inserted him into me): "Oh my god... it feels so good."

I lean forward a little more, which gives me an even better angle to grind. And I kid you not, this boy's cock feels so good inside of me. I know I'm repeating myself, but I could not give two shits about how short it is. I know, I'm as surprised as you are! But this is fucking great!

Jake seems to be thoroughly enjoying himself too, as he transitions into a huge grin. Although, based on where his eyes are focused, it seems like it's my shirt that's making him smile? I guess it is kind of ridiculous that I'm still wearing it.

Me (calling him out): "What're you grinning at? Is it my stupid t-shirt?? I only put it on because it's a mom shirt."

Jake (still beaming): "No, the shirt's fine. I like the shirt... it's your boobs..."

Me (a little self-conscious now because I know they're hanging down all floppy and clearly visible through my neck hole): "Yeah, that's the one downside to this position. Sorry."

Jake (subtly shaking his head): "No... don't apologize. They look amazing."

Me (as I can't help but laugh at that): "Ha. If you say so."

Jake (reiterating): "No. I like them... because they remind me... they remind me of when my mom would always tuck me in at night. She'd always wear a nightgown... and it was so loose... and when she'd lean over to give me a kiss, I could see her boobs like I can see yours now."

Ha. It tracks that his mom would wear a nightgown. She's my age, right? Who wears a nightgown these days?! And it's also notable that apparently we're taking a break from our roleplay, because Jake just referred to his mom as if she's not here, instead of referring to me playing the part of her. I guess Jake actually losing his virginity was enough to snap us out of the pretend mother-son scene we had been playing up until this point.

Me (perfectly fine to refer to his mom as someone else): "So did you like being able to see your mom's breasts like that?"

Jake (still struggling a little to speak as I continue to fuck him): "Yeah... I loved looking at them."

I have to admit, yet again this is kind of hot to think about.

Me: "Did you ever want to reach out and touch them?"

Jake (with a hint of desperation): "Oh my god, I always wanted to touch them. I wanted to grab them so badly."

Me: "Well... you can touch mine."

I assumed Jake might reach out with a hand and softly caress one of my breasts, but instead, as soon as I suggest that, he takes his two hands and shoves them through the neck hole of my shirt and firmly grabs ahold of both of my boobs.

Jake (with eyes closed now): "Ohhhhhh... they feel so good."

Okay, my shirt needs to come off.

Me (as I start lifting my Mother's Day taco t-shirt up and over my head): "Here, let me help you."

Jake removes his hands from my chest just long enough for me to pull my shirt off, at which point his mitts head straight back to where they were before, firmly clamped onto my very modest tits.

Jake (seeming so appreciative): "Oh Becca, your boobs are amazing!"

Wow. He just called me Becca. He really has moved on from the roleplay. How interesting! Not that I'm complaining, as fuck, this is just so great, either with or without me pretending to be his mom.

It's so great in fact that I need to kiss this boy. Like really kiss him.

So I lean forward and down, and as I do I force his hands to come off of my chest. Next, my lips head straight for his mouth, while he moves his arms around back to pull me in as well. Once our lips make contact, I immediately force his mouth open, and then I send my tongue past his parted teeth to meet his tongue on its own territory. Mmmmmmm. It's so good!

I haven't really made out with Jake yet, and so it's kind of amazing to have our first passionate kiss happen while he's already inside of me. But it makes me feel so connected to him. And I have to say, for a virgin, he has a pretty decent fucking rhythm going right now. And he also seems to be showing no warning signs of coming either, which is fucking amazing, but probably expected given he's already come twice tonight. Kudos to me on planning this out perfectly! : P

But as we continue to kiss, and fuck, and his hands are still lovingly rubbing my upper back, I realize something. I'm actually pretty close to coming! Yep, I think I'm well on my way. And why shouldn't I be, as this whole night has been building and building to this wonderful crescendo.

And don't worry, there is no need for me to delay my orgasm any longer. I am ready to finally come all over this sweet boy's tiny, little perfect dick.

And fuck, his tongue feels so good playing with mine. It's been so long since I've kissed someone like this, and it's such a great trip down memory lane. I have to say, he's a surprisingly good kisser, too! God, I love the fact that he's a virgin, though. He's like the best possible combination, so young and innocent, but actually not half bad at kissing and fucking.

And I love thinking about how much he would masturbate, and how he's been waiting for this moment his entire life! And oh my god, I still can't get over the fact that he used to stick that miniature baseball bat up his own ass. That is still so fucking hot to think about.

But most of all, I can't stop thinking about Jake and his mom. I don't think I'll ever fully come to grips with the fact that he has all these sexual fantasies about his own mother. It's so crazy, and it's so amazing that he actually told me about it. But I love that he did.

It's such a huge turn on to think about. The naughtiness, the taboo-ness of it. Fuck, I think I need to sit up again. Yeah, I want to come while riding him. That seems like it'll feel so amazing.

So I break out of our kiss and I press my hands into Jake's shoulders in order to lift myself up. Now I'm back to sitting straight up, but I don't stop grinding Jake's cock, not even for a second.

Oh I'm going to come. I'm going to come so hard. There's no doubt about it. And you know what? It's this idea of Jake and his mom that's going to put me over the top. I can't believe he would spy on her! And I can't believe he would watch his own mom orgasm, and then go back to his own bedroom and jerk off to that. And holy shit, I really can't get over the fact that he would eat the crusties out of her dirty underwear! And then the staring at her boobs in the nightgown. Fuck. It's all so shamelessly perverted.

And I'm telling you, the mom knew. She probably still knows! There's no way she doesn't. She must've seen him through that crack in the door. Watching her. I'm sure she did.

And during those goodnight kisses? There's no way she wouldn't have seen his eyes peering into her nightgown. Jake wouldn't have known enough to hide his blatant gawking. In fact, I'm guessing she'd see him staring at her hanging tits and just chuckle to herself at how horny her son must be.

And you know what? I bet she even knows he was going through her underwear. I mean, I know I'd notice something like that in a heartbeat. If my laundry was all askew from being rifled through? Damn straight I would, because again, I would bet anything that Jake wasn't being meticulous about putting it all back how it was. And given everything else, I'm sure she could put two and two together and know immediate what he had been looking for in that pile of her dirty clothes. Fuck, that's so hot in itself. It's so wrong, but so good.

Me (with my eyes closed and hands now on Jake's chest): "Oh, I'm gonna come soon."

Jake: "Oh Becca, I want you to come so bad."

Me (fuck, I can't believe I'm going to do this, but I am): "Oh Jacobson... call me Mom. Don't call me Becca."

Fuck, now I'm the one who's completely shameless.

Jake (with immediate compliance): "Oh Mom, I can't believe I'm finally getting to fuck you."

I grind his cock even harder.

Jake (continuing): "I've always wanted you more than anyone else. I've always wanted your pussy more than anything else. I've wanted it forever..."

Oh god, Jake. This is perfect.

Me (opening my eyes now to stare down at this adorable boy): "Oh, I've wanted it too, Honey Bear. Your cock is the only one I ever think about. I've always known you wanted me, but I could never tell you how much I wanted you. I've always wanted your cock in my pussy so badly."

Jake (looking very serious now): "Oh Mom, just come. I want you to come so hard on my cock. I want you to come all over it. I wanna give you the best orgasm of your life."

Oh this sweet boy. His love for his mom. His desire to consume her vagina. To lick all of her juices. To suck on her dirty underwear. To have her stick objects up his ass. Oh I wish I could watch Jake's mom eat his asshole in real life. Fuck. I'm going to come.

I grind harder than ever before, and yep, I'm coming. And just as my orgasm commences, Jake sits up and completely surprises me by sucking my entire right boob into his mouth. It's both shocking and wonderful, as I realize I haven't had someone suck on me like this since my days of breastfeeding, so long ago.

And at this point, my instincts take over and I grab ahold of the back of Jake's head with my right hand, while I squeeze my unattended left breast with my other. I continue to frantically buck my hips forwards and backwards on Jake's perfect cock, and I come so fucking hard.

Me (with a great sense of release): "Ohhhhhhhhhh my god."

The stimulation of my clit, the feeling of his penis up and inside of me, all the forbidden taboo tales and desires, and now this one final element of Jake sucking so hard on my boob, he's basically breastfeeding from me. It's all so perfectly weird, forbidden, sweet, innocent, and extremely perverted.

It really is the best orgasm of my life.

And then it's done. And I feel so unbelievably good. Euphoric even. But also exhausted. And slowly, my hips stop grinding, and my whole upper body collapses down onto Jake.

Me (with my mouth pressed up against Jake's collarbone): "Oh my god... that was so incredible."

Jake doesn't respond, and considering I can't see his face, I have no idea how he's reacting right now. Is he happy? Terrified? Weirded out?

I give him a few more seconds to say something, but still it's just silence. My curiosity gets the best of me, so I summon every ounce of strength I have left, and I push myself up, just so I can get a view of Jake's face.

Ha. What a cutie. He has the absolute biggest grin I've ever seen, of pretty much anyone ever. In fact, he looks almost too happy to talk, which must be why he didn't respond before.

Fuck, this makes me feel so good to see that he's every bit as blissfully content as I am about what just happened. But as perfect as that orgasm was, there's still one final element that needs to occur, to truly make this a perfect night.

In fact, just the thought of it gives me a second wind.

Me (mere inches from Jake's face now): "Jacobson, I need you to come inside of me. I need you to come inside of your mom. And I need you to blow the biggest... fucking... load... of your entire life... inside your mom's pussy. Can you do that for me?"

Yeah, fuck this idea of Jake and Becca having sex. I'm all-in on this fantasy. I'm Jacobson's mom, and I need my son to fill me up with every last drop he has.

Jake (after nodding ever so subtly): "Can I be on top?"

Fuck yeah, you can. I use my new found energy to simultaneously lean back while pulling Jake's upper body up off the bed. As we do this, we seamlessly flip ourselves over and immediately end up in a standard missionary position, almost like we're a couple of acrobatic porn stars. Amazingly, I don't think Jake's cock ever leaves me during our whole transition.

And now that we're in Jake's desired position, he doesn't waste any time in starting to fuck me, just as passionately as I fucked him a few moments ago.

With my back flat against my soft, pillow-topped mattress, Jake takes ahold of both of my hands and interlocks his fingers with mine. He then pushes them up above my head and pins them down forcefully against the bed. As he does this, he has a look of determination and desire on his face that I've never seen him have before, in the brief time that I've known him. It's wonderful.

Me (staring right into Jake's eyes): "Fuck your mom's pussy. Fuck it so hard, Jacobson."

Jake does as he's told and he immediately starts pounding me. His pelvis is slapping into mine, and with each thrust he gives off the cutest little grunt. He's working so hard, that I'm starting to see little beads of sweat forming on the side of his forehead.

In fact, his intensity and rhythm are so impressive, that it reminds me of a conversation I once had years ago with a male friend of mine, where this guy was trying to convey to me what it feels like for men to have sex. He explained that the typical motion of a man fucking, and specifically having sex in the missionary position, is one of, if not the most natural and instinctual movements a human male can ever make. He likened it to breathing, and he explained how even the very first time he ever had sex, for whatever reason, it felt like he had been doing it his entire life.

I actually think about that conversation a lot, and while I have no idea if all guys would agree with his description of fucking coming as naturally as breathing, as I lie here and see firsthand how Jake is thrusting into me right now, I can't argue against it. This boy is humping me with such vigor, passion, and competency, that if it was any other skill in life, it's hard to imagine him being this capable, the first time he ever attempted it. But I guess we have evolution to thank, because young Jacob, who's never fucked anything in his life before tonight, is using his millions of years of caveman instincts to know exactly what to do to me, and to my pussy.

It's so wonderful, but it's also time for Jake to come. I want him to come so badly, and I want him to come right now. I'm sure under normal circumstances, any virgin boy would've orgasmed long ago just from the grinding I gave him, doubly so when you consider Jake's history of coming from simply brushing up against the corner of a desk. : P

But like I said, he's already two orgasms in, so I may need to work for this one a little bit. The only catch is, with my hands pinned back as they are, there's not much I can control right now, so I do the only thing I'm capable of, to help facilitate this third orgasm. I spread my legs open a little wider and I do my best to lift my hips off the bed to meet Jake halfway on every thrust he gives me. This definitely ups the impact of our fucking, and leads to even louder slapping noises every time our pubic areas collide.

Me (figuring I can also use my words to help the cause): "Oh Jacobson, it's been soooooooooo long. I waited my whole adult life for this."

Jake's mouth opens, and he looks like he might be close. He doesn't say anything though.

Me: "I haven't had sex since the day you were born. I wanted to wait... for you..."

Obviously I have no idea if that's true, as all I know is that Jake mentioned his mom never seemed to date anyone. And to be honest, it seems extremely unlikely that she would've abstained from sex for that many years of her adult life, but who's to say it's not possible.

Jake (finally breaking his silence during his intense fucking of me): "Oh my god, Mom, are you serious?"

I smile and nod to confirm it's true. Like I said, why not?

Jake (giving off a total O-face right now): "Ohhhh god..."

Me (let's bring this puppy home): "Oh Honey Bear, this feels like it's my first time, just like it is for you... will you deflower me? Will you deflower my pussy that I've been saving just for you?"

And with that, my young, adorable 18-year-old friend gets to experience the sensation he's always dreamed of. Not only is he orgasming into a warm, wet, vagina for the very first time, but he's living out his ultimate fantasy of coming inside the pussy of his own mom.

It's fucking incredible.

Jake finally lets go of my hands, and I use their newfound freedom to reach around back and grab ahold of Jake's tight, little butt cheeks and pull him and his wonderful cock into me even harder.

Jake (with a low, deep moan): "Oh Mom... oh fuck... oh Mom..."

Jake's whole body is spasming, and I can only imagine the amount of semen he's currently depositing into my vagina. On the one hand, it's his third time coming, so it's possible there's not much left. But on the other hand, I saw firsthand, both in his underwear and then into my throat and out my nose, how much this boy can come, so it seems totally plausible that this load would be just as epic.

Me (speaking softly as not to disturb Jake during his big moment): "Oh Honey, just fill me up... fill me up with every last drop you have."

God I love this. Jake's definitely reaching the end of his orgasm though, and I can already feel myself starting to reflect on everything that just happened. Holy shit. What a night.

Me (as Jake starts to quiet down): "Shhhhhh... Hon... shhhhhhh..."

Yep. He's all done. Jake collapses on top of me, completely spent, but with his penis still inside of me.

Me (starting to rub Jake's back): "There we go Honey... that was so special. You made your mom feel so good."

How fucking insane was all of this? Can you believe that at the start of the night, I was all worked up, obsessed even, about the idea of Jake simply coming in his pants! And somehow we went from that extremely innocent and naive act of prematurity, to one of the most taboo and perverted fantasies possible, a boy losing his virginity to his own mother.

As I switch to softly caressing Jake's head, I continue to run through the highlights of this evening in my mind. On top of all the mom stuff, there was also the wonderful exploration of this 18-year-old boy's butthole. I think what I loved most about that was that he had already been experimenting on his own with anal play, and I just helped him take it to a whole new level. I still love that mental image I have of him forcing than miniature wooden bat up against his bedroom wall. And while I didn't get to see that for myself, I did get to explore the inside of his young rectum with my own finger, which was pretty fucking crazy in its own right.

Me (as I give Jake's head a soft kiss while he continues to lie on top of me): "You're sooooooooo sexy, Honey."

Ha. And then there was that Angry Dragon I gave him. I bet he never forgets that for the rest of his life!

Jake (mumbling so quietly into my chest, it's barely audible): "Thanks, Mom. I love you... so much."

And then there's that. The whole mother-son aspect. I'll be the first to admit that I was initially skeptical of this whole roleplay. But holy shit did I end up embracing it by the end. I definitely surprised myself. But as hot as it was, and still is to think about it, I think it's actually secondary to what I loved most about tonight.

Wait. Holy shit. Jake's breathing just changed. It's all rhythmic and measured. He's fucking asleep! That's so sweet.

Me (as I ever so gently rub his back again): "Shhhhhhh... there you go, Honey Bear. Get some sleep. You deserve it."

Let this boy sleep on me all he wants. He can even sleep in me, as I'm pretty sure his cock is still inside my vagina. Although I figure it's only a matter of time until it softens up enough to slip out, at which point I'm sure my sheets are going to get soaked. Oh well!

Ha. That reminds me, I still haven't moved Jacob's load of laundry over to the dryer. They're definitely going to be sitting there overnight! : P

But anyway, where was I? Oh yeah, about to explain what I loved most about tonight. You know what it was? I loved the confessions.

I think the very first one took place last weekend in front of his dorm, when Jake confessed that he actually did come in his shorts, just as all of his friends had surmised. I loved the vulnerability that Jake displayed in telling me that, not to mention the embarrassment he must've endured both at the time it happened as well as when he rehashed it to me.

Now obviously, the biggest confession of all was everything dealing with his mom. But it wasn't just the bombshell that he had sexual feelings for her, but also all the little extra confessions along the way. The spying on her masturbating. The watching of the door while he anally masturbated himself, hoping that she would catch him. The licking and sucking of her dirty underwear. Even the peering at her breasts down her nightgown. Every single time he admitted something new, it just turned me on more and more.

I sweetly give Jake's curly brown head another kiss, and now he's full-on snoring on top of me.

Last week, I came to grips with the fact that not only do barely legal boys turn me on, but that the more innocent they are, the better. Basically, bring on all the 18-year-old virgins you got!

But this week, I've discovered yet another layer to that fetish. And it's one that I probably couldn't even have told you existed, let alone what the name of it is. But I love, love, love this idea of these young, innocent, virgin boys confessing all their greatest secrets and desires to me. And obviously, as you can tell from tonight, literally anything is fair game.

Give me your weirdest masturbation stories. Your biggest crushes, no matter how forbidden they are. Tell me what you've always wanted to do to a girl, and who you want her to be, and I'll become her. Tell me what you want this girl to do to you, and I'll do it all. And if you like it, I'll do it all again.

Because what really turns me on the most, is turning you on. And it's hard to imagine anyone getting turned on more, than a shy, nervous, horny, perverted, 18-year-old virgin who has secrets he's scared to death to tell anyone. But there's no need to be scared, at least not with me. Because not only will I not judge you for your deepest and darkest fantasies, but I'll do everything humanly possible to make all of them come true.

The End

(for now)