Coach's Cutie Ch. 09

Before I begin, I wanted to let everyone know that this story, Coach's Cutie, is nearing its end. There will be one more chapter (#10) to follow this one, but that will be the final piece in the series. So now that you're all aware :) I hope you enjoy these last two chapters!

Coach's Cutie - Chapter 9: The Third Wheel

Me (holding Greg's hands while facing him): "You ready?"

Greg (confidently): "I am."

Me: "So what happened? How is it that you don't seem nervous at all about this anymore??"

Greg (subtly shaking his head): "I don't know. I just... I just know I want this, I guess?"

Me (after leaning in to give him a quick peck): "Well I love it. I love how happy you seem right now."

Greg (with such a genuine smile of appreciation): "Thanks, Sweetheart. You really are amazing."

I peak over at the clock hanging in my kitchen and I see it's just past 7:50 pm. I had told Maddie to come by at 8, so we're now mere minutes away from this whole drawn out fantasy finally coming to fruition.

Sure, a few nights ago when Greg got to go down on Madison (twice!), that was pretty hot. And satisfying. But it also clearly freaked my boyfriend out.

Immediately after it was over, Greg started panicking that he had made an enormous mistake. It didn't matter how sexy, adorable, and unbelievably alluring this 18-year-old student of his was, and how much he enjoyed having the chance to please her. All he could think about was that he could end up losing his entire teaching career over what just happened.

But then something changed, and to be honest, I don't know what it was, or even when this shift in his mindset happened. All I know is that Greg now seems completely fine with everything. It's a very weird and unexpected turn of events, because it's so out of character for my extremely calculating and risk-adverse boyfriend. But considering how badly I want all of this to happen, I probably shouldn't be complaining, right?

Although maybe I'm overthinking this. Maybe Greg hasn't changed, but instead he really has evaluated everything, and it turns out the pros just happen to outweigh the cons? I mean, It's conceivable that Greg thinks so highly of Maddie, that he's simply decided the chance to be with her really is worth risking everything.

Regardless, I'm just so happy that he's happy. And now that he's 100% committed, I really can't wait to see this happen. I want him to take Madison into his arms, with their two naked bodies pressed against each other, and just watch him bask in the euphoria that comes from finally getting to be with the one girl he's coveted for so long.

In fact, that makes me realize something.

Me (while still holding Greg's hands): "Hey. The other night, you didn't even get the chance to kiss Maddie, did you?"

Greg (matter of factly): "Well... I mean, I kissed her vagina plenty."

Me (chuckling): "Yeah, obviously. But no, I mean like on the mouth. Like a real kiss."

Greg: "Uh, no. Yeah I didn't. But I'm guessing I could tonight? Hopefully?"

Me (seductively): "Can you do something for me?"

Greg (intrigued): "Yeah, sure. What?"

Me: "When you cum inside her."

Me (with emphasis): "And you will cum inside her."

Me: "Can you make sure you're kissing her when you orgasm? Like one of those intense, aggressive kisses you try to do to me sometimes?"

Greg (agreeably): "Oh. Sure. Yeah. I could do that."

Me (after giving Greg my own sensual kiss): "Good, I want you to be jamming your tongue down that sweet, little girl's throat, while you're filling her pussy with every last drop of cum you have."

Greg (with an intense but also now slightly concerned look on his face): "Oh. Okay. But do you know if she's even on..."

Knock knock knock!

Me (opening my mouth with excitement): "She's here!"

Wow. What perfect timing! I'm pretty sure Greg was about to ask me if Maddie is on birth control, but I kind of like leaving that question unanswered, at least in his mind. I know from my conversation with Maddie the other day that she actually has an IUD, but I think the danger and the mystery of Greg not knowing that makes everything a little bit hotter.

Anyway, the more pressing issue right now is that Maddie is actually here! Greg seems to be realizing the significance of this moment as well, as I see him take a very pronounced and noticeably deep breath.

And while his heart rate is probably sky rocketing, I leave my boyfriend to go answer the door. Meanwhile, Cassie, my precocious foster dog and unknowing pawn in this whole elaborately planned seduction, comes running out, barking full of excitement.

Me (as I open the door and see Madison standing there, looking as cute as ever): "Hey! Good to see you... come on in!"

Maddie (bending over to greet the dog she used to foster herself): "Hey there Cassie, you sweet girl!"

I usher Madison in, and while you might think it would make sense for us to all have a drink or two, just to help take the edge off. After what happened the last time and how Greg got so fixated on Maddie having even a small amount to drink, I decided ahead of time that it's just not worth it tonight.

Me (to Maddie): "Can I get you a glass of water? Or a soda?"

Maddie (so politely): "Oh, I'm okay. But I appreciate it."

While Maddie is turning down my offer of a soft drink, I see Greg come moving in towards the two of us with a determined look on his face. Something's up. This seems unexpected in some way.

And then I get my confirmation.

Yep, something is definitely up, as Greg comes right over to Maddie, with a weirdly aggressive amount of urgency. But then he abruptly stops about a foot in front of her, before taking his right hand and softly, but confidently, brushing her beautiful light blonde hair behind her left ear. Maddie looks slightly caught off guard at this very sudden approach from her basketball coach, but she seems mostly fine with it.

But then without saying a word, Greg leans down and kisses her. At first, it's a firm but respectable closed mouth kiss, but then he transitions into a full blown French kiss. Maddie seems to flinch ever so slightly initially, as I see her head inch back and away from Greg, but soon enough it's clear she's actively kissing him back.

Oh my god. This seems so aggressive from Greg! But Maddie appears to be okay with it? Either way, he really is like a different man tonight! Holy shit.

Next, I see Greg's hands start to caress Madison's back, while her arms reach around and lock themselves behind my boyfriend's waist. And as these two continue to make out, I'm left standing here, pleasantly surprised at how quickly everything is already progressing during this second encounter.

Greg finally comes up for air as he pulls back from kissing his student, before breaking out into a huge grin.

Greg (to Madison, and so softly I can barely hear it from where I'm standing): "I've wanted to do that for so long."

Maddie doesn't say anything, but does respond with a huge smile.

I have to say, I kind of like this new aggressive version of Greg, again as long as Maddie is also fine with... oh my god, now Greg just picked her up into the air! And he's carrying her. And now he's apparently taking her to the bedroom!

Yeah, we are not messing around tonight. We're doing this right the fuck now, and I love it.

I follow the two of them into my bedroom, and I see Greg toss Maddie relatively forcefully onto my queen sized bed. She bounces up and down, and obviously it's plenty soft, so she's in no danger of getting hurt, but it's still a little surprising to see him callously throw her like that. Again, Maddie seems a little surprised with how rough Greg is being with her, but she still looks more startled than worried, so I don't think I need to intervene or anything. At least not yet.

With Maddie now lying on the bed and looking up at Greg, I see my boyfriend immediately begin to take off his clothes. First, he removes his shirt, and then it's his jeans. As he's doing this, Maddie follows suit and starts undressing herself while she sits there on the bed. Yet again, I think it's a pretty clear sign that this teenaged girl is indeed comfortable with how fast everything is progressing. I don't know why I'm so paranoid that she might not be okay with all of this, but I just am for some reason!

Anyhoo, with the two of them almost done disrobing, I contemplate for a second about taking off my own clothes, but then I decide that might be kind of weird. I mean, am I going to be taking part in this as well? Am I allowed to? Do I even want to? It's strange, for as much as I've fantasized about this exact moment, I never actually thought about what my role in it would specifically be!

I decide to keep my clothes on and continue to just watch from the sidelines. I figure why rock the boat if I don't need to, as the last thing I'd want to do is make either Greg or Maddie uncomfortable and derail what's about to happen.

At this point, my boyfriend is now buck naked, while our beloved high schooler is just finishing taking off her bra and tossing it to the floor. That leaves one single article of clothing between the two of them to still be removed, Madison's underwear. Greg apparently will be doing the honors here, as he reaches down and gently takes ahold of her black satin undies and slides them off her short but nicely toned legs.

As he does this, there are a couple of things to note. First, it seems like Maddie wore fancier underwear tonight compared to the last time she was here. In her defense, this past Sunday she probably wasn't expecting for the night to end up with Greg's face between her legs. Tonight though, I think there was an entirely different set of expectations coming in, which would explain the sexier undergarment.

The second thing to point out, and I apologize for being so graphic here, is that this time there's definitely not a noticeable trail of vaginal secretions (if there's a better term for it, by all means I'm open to suggestions) clinging to Maddie's underwear as Greg removes them. I mean, the first time, that pair of cotton blue undies she had on was absolutely soaked! But I wouldn't take the missing wetness as a sign of any less interest on her part, but rather just a byproduct of how quickly things are moving along tonight.

But more important than either of those two things, is the fact that for the first time ever, Greg and Maddie are now both completely naked in front of each other! And holy shit do their two nude bodies look so hot.

Now, I think I've written plenty already about how beautiful Maddie is, and how jealous I am of her adorably youthful body. But in case I haven't pointed this out enough, I also want to be clear that Greg is absolutely no slouch when it comes to his own physique.

He has an interesting build though, as he's not a huge guy. But he is tremendously fit and surprisingly strong, and so he has what I would call a deceptively smoking hot body. If all you ever did was see the guy when he was fully dressed, you probably would never guess the definition and tone of muscle he has underneath those clothes, let alone his shockingly impressive abs!

And I think I'm seeing Maddie realizing this exact phenomenon in real time, as her eyes are darting back and forth between Greg's face and his naked body below. Although, let's be honest, as impressive as his six-pack is, I think most of her glances down are focusing on one particular thing, his fully erect cock.

And I get it, it's the first time she's ever seen this man's penis, and on top of that it's currently sticking straight out and pointing right at her! So how could she not be looking at it, right?

But I have to say, watching this high schooler staring at my boyfriend's cock is extremely entertaining. I'm so curious what she's thinking! Now, speaking from experience, it definitely is a nice penis. Greg keeps his pubes trimmed relatively short, and when he's got a full hard-on like he does right now, it looks surprisingly big against his slender frame.

But speaking of hair, one other thing Greg's body does have is a lot of fur! This includes his legs and thighs, as well as his arms and chest, but thankfully not his back, ha. But I would have to assume that the one boy Maddie has been with, that William kid, couldn't possibly have had as much body and chest hair as Greg does. So, I think it's safe to say she's never seen a naked body that looked anything like this before.

And along those lines, my god, I just absolutely love the juxtaposition of these two. There are so many ways in which Greg and Maddie differ from one another, and this contrast is such an amazing turn on for me. Part of it is their huge age gap, and the taboo nature of the fact that he's more than twice her age.

But then it's also the whole student teacher relationship, both in terms of their mismatched levels of sexual experience, where we know Greg is so much more well versed in bed than young Maddie is. But then also, you add in the fact that Greg was once this girl's 10th grade teacher, and their history from being in class together and the power dynamic that brings into play, and it's even hotter.

And then finally, I think the biggest turn on for me of all, is the stark differences between their two naked bodies. You have Maddie, and her smooth, young, and petite shape along with her pale, flawless skin and her soft, light blonde hair. She's the perfect embodiment of youth, innocence and purity.

And then you combine that with Greg's lean but muscular build, and his plentiful covering of manly body hair all over. He looks so much older, and so much stronger, than this sweet little girl in front of him. But despite that hardened facade of a grown man we see, I know for a fact there's a damaged and jaded soul in there. There's a man, a husband in fact, who had to do the unthinkable, and bury his young wife before their lives had barely even gotten started.

And so as I look at him standing there, with his rock hard penis pointing straight out at the one thing I know he wants more than anything else right now, all I want is for him to have it. Fuck, I want it so badly for him, because he deserves it more than anyone, after what he's been through.

But I also want it for Maddie. I know it's clearly not the same level of hardship, but knowing how tough it's been for her to see her ex-boyfriend Lucas with somebody else, a friend and teammate in fact, it just makes me want her to be happy as well. To feel wanted. To be desired. And just look at her sitting there naked. She's so goddamn cute! She deserves this too.

So holy fuck, can we just do this already?!?

And as I'm thinking this, I see Greg place one knee up onto my bed and start to climb up. Maddie seems totally receptive, as she reacts by slowly spreading her legs open to welcome her approaching coach in. And as Greg begins to crawl across the mattress towards his forbidden teenaged crush, I'm so excited, but also so curious to see what he's going to do to her first!

Is he going to climb up over her and plant another huge, passionate kiss right on Maddie's mouth? Or is he instead going to start by using his hands to caress and fondle her wonderfully naked, young, nubile body? Or maybe he's just going to dive right in, skip the whole foreplay, and immediately attempt to jam his rock hard cock inside her sweet little pussy?

As it turns out, the answer is yes. Greg moves in and instantly starts doing all three of these things simultaneously. His fingers touchdown near Maddie's waist, before gracefully making their way up her cute, little ribcage until he's cupping her small breasts in each of his two large palms. His mouth heads straight for Maddie's face, and they resume the same passionate French kiss they had started before when they were out in my living room.

And then most importantly, I see his pelvis move aggressive into Madison's crotch, and it becomes immediately clear that he's not trying to dry hump her, or simply rub his genitals against hers. He is definitely trying to fuck her.

Maddie's legs are spread wide, and despite it being out of view, I can tell Greg is lined up to where his cock is right where her vaginal opening must be. The positioning looks correct, the angle looks good, but I don't think he's inside of her, at least not yet.

Instead, I can see Greg shifting his hips around, as if he's still working on the proper alignment, and then every few seconds I see him thrust forward. But each time, he seems to be failing to reach his desired result.

I think part of the issue is that Greg's primary focus, at least for the moment, is on what his hands and mouth are doing, and not his cock. His head's orientation is constantly switching from the left side of Maddie's face to her right. Meanwhile, their kissing is so passionate and sloppy that I can actually see their tongues dancing in circles around one another.

Greg's hands are also constantly moving, as they keep switching from one part of her upper body to another. They go from Maddie's boobs, to her arms, and then up to her head and hair, before returning back down to forcefully squeeze her perky little tits some more.

Wow, I can tell from his movements and demeanor that Greg is relishing the chance to fondle Maddie's petite little body right now. In fact, he appears to be enjoying it so much, that it almost doesn't seem to matter that he's not actually having sex with her yet.

And just as I'm thinking this, I see it. It's about to happen. Holy shit. Those tiny, persistent thrusts of Greg's hips, I'd recognize them anywhere. I know, because I've been on the receiving end of them many times before. And from that experience, I can tell he's about to break through, any second now.

Just to give you a little background here. Sometimes when I have sex, my man and I will both end up plenty lubricated before we actually even attempt to have intercourse. This could be from him licking me, or me sucking him, or simply him spitting into his hand to wet his own cock. Or it could be any combination of the above.

And so whenever we're all proactively wet like that, it's usually pretty easy for the man to slide right into me. But it also kind of takes the suspense out of it. In fact, I've actually come to prefer the approach that Greg took with Maddie just now, which is the completely hand and spit free method of trying to enter the vagina. For lack of a better description, it's kind of a dry, brute force approach.

It definitely takes longer, but interestingly enough, I love that aspect of it, because you never know when it's actually going to happen. And while the outside of the genitals start out completely dry, there's always a hidden well of wetness inside that pussy just waiting to spill out. And so each initial poke up there unleashes a little bit more lubrication, which allows the next push to slide in a tiny bit further, releasing even more of those magical juices. The progress is slow, but consistent, however the anticipation, at least from the woman's perspective, is just incredible.

You can tell when he's getting close. He's getting lined up, and you can feel your moisture starting to spread. He's an inch-and-half in you. Then it's two. Then it's two-and-half. Each thrust is a tiny bit wetter and a little bit deeper.

And that's exactly the stage where Greg and Maddie are right this second. My eyes are laser focused on their conjoined pelvises, as my boyfriend continues to give her these little mini pumps in rhythm. Meanwhile, they're still so engrossed in kissing each other, than I'm sure they have no idea how intensely I'm staring at their crotches.

And then it finally happens. Greg's next thrust gets enough momentum and enough lubrication, and there's no stopping it. He goes from halfway in, to all the way deep, and believe me, I'm so jealous of Maddie right now. That moment his cock first plunges all the way inside of you, while his pelvis simultaneously slams into your clit, it just can't be beat.