Coach's Cutie

Coach's Cutie - Chapter 7: How Many Licks Does It Take?

This is the moment we've all been waiting for.

Maddie, our sweet, lovable, cute-as-a-button 18-year-old high school student, just flat out propositioned my 37-year-old boyfriend. And while I can tell she's trying to play it cool by putting on a brave and somewhat seductive smile, her feet are telling a much different story. It's subtle, but the way she keeps crossing and uncrossing her ankles is leading me to think she's much more nervous than she's letting on.

Greg on the other hand, isn't hiding anything, as he looks downright shell-shocked. But that's not surprising in the least. You see, my boyfriend is one of the most cautious, risk-adverse, and self-disciplined men I have ever met in my entire life. And under normal circumstances, he would never even entertain the thought of potentially throwing away his career as a high school teacher and coach, to partake in some sort of an illicit relationship with a student of his.

But as I've learned over the past month, there is nothing normal about the feelings and desires Greg has for young Madison here. Even so, it's a minor miracle we've gotten to this point.

Greg just got done explaining to the two of us, a truly elaborate and bizarre fantasy scenario involving some imaginary secret club where Greg would offer to lick the pussy of any females who wanted him to, no strings attached. And when I say bizarre, I mean it! His explanation involved a top-secret referral only screening process, a Google Sheet (which he keeps referring to as a Google Doc) used for making reservations, rules about what was and wasn't allowed, and of all things, Tootsie Roll Pops.

Which, oh shit. That gives me an idea.

Me (to Greg and Maddie, right as we're all trying to process what exactly happens next): "Hold on one sec. I'll be right back."

I have this giant bag of candy in my pantry, and I bet it has a Tootsie Roll Pop in it. It has to!

I retrieve this brown paper bag that's over half full of a completely random assortment of candy, and as I'm bringing it back into the living room, I start digging through it as I'm walking.

Greg: "What is that?"

Me (as I plop the bag down on the coffee table): "Last Halloween, a bunch of people at work had brought in all their leftover candy, and somehow I ended up being the one to take it home once everyone was done picking through it."

Me (looking up from the giant stash): "Don't judge."

I'm pushing the candy around inside the bag, but it's hard to see what's what. The good news is, most of the chocolate candy is long gone from the collection, so it's almost all sugary candy, like Jolly Ranchers and yep, lollipops. The question is, can I find a Tootsie Roll Pop? I'm sure we could still go on ahead with this whole liaison without the symbolic sucker, but I think having one would be satisfyingly poetic.

At first, I think I've found what I'm looking for, but as I pull the promisingly sized lollipop up to take a look, I realize it's a Blow Pop, and not a Tootsie Pop.

Me (tossing the Blow Pop to Greg): "Here. If you branch off into a second service for dudes, this would be perfect."

Greg (after catching the lollipop in his hands): "Huh?"

Me (annoyed that I have to explain my joke, because I thought it was a pretty good one): "If you had a service for dudes? Do you get it?? You'd have Blow Pops instead of Tootsie Pops?"

Maddie laughs. Because she has a sense of humor and it's a funny joke! I'm also starting to realize how much I legitimately like hanging around this girl.

Me (as Greg still gives me a blank look): "C'mon! Since it's dudes, you'd be blowing the guys. You'd be giving them blowjobs. Blowjobs and Blow Pops? Do you really not get it??"

Ah whatever. Tough audience. I turn my attention back to the giant grab bag of candy, and Eureka! I found one! I pull out an untouched Tootsie Roll Pop in an orange wrapper and triumphantly hold it up.

Me (irrationally excited over this): "Found one!"

Maddie smiles, probably at the absurdity of all of this, and as I move the brown paper bag filled with candy out of the way, I offer the sacred Tootsie Roll Pop to Greg. Once he takes it, he'll be free to symbolically offer it to Maddie, and in the process make this elaborate fantasy off his officially come true.

Greg (after timidly accepting this piece of candy): "So we're really doing this?"

Greg (directly to me): "Are you sure this is a good idea?"

Ugh. Why does he have to make everything so goddamn difficult! I can totally tell that if anything, and I mean anything, about this whole affair goes wrong, he's going to come back and try to blame me. But fuck it. I don't care. We're doing this.

Me (to Maddie): "Are you up for this? Are you willing to be the first ever official user of Coach's Free Tootsie Roll Pop service?"

Maddie (herself now looking a little unsure): "Yeah... I think so?"

Fuck. Now Madison's having doubts?? Am I going to have to personally drag these two across the finish line here myself?!?

Okay, calm down Becca. This obviously is a big deal for both of them, for different reasons, and it's not unexpected that there would be nerves. Let's take a step back and just confirm that everyone does want this.

Me (trying to give her a chance to really think about it): "Maddie, do you wanna do this? Like, are you sure? You definitely don't have to."

Maddie (much more confidently this time): "No, I'm sure. I definitely want to. Just nervous is all."

Okay, good.

Me (smiling): "That's okay. It's totally understandable to be nervous."

While I think it was important to clarify with Maddie, I'm not going to bother asking Greg a second time.

Me (excitedly): "Okay then, well let's do this..."

I stand up and gently lift my coffee table, which honestly isn't very heavy, out of the way so the space in front of the couch where Madison is sitting is completely clear. As I do this, Cassie the dog, who had been sleeping next to Maddie for the past half hour or so, groggily jumps down and trots slowly over to her bed on the other side of the room. She obviously couldn't care less about what's about to go down. Or perhaps I should say, who's about to go down on whom. :P

That leaves Maddie on the couch by herself, looking ready, but on edge. I'm sure her brain is going a mile a minute right now trying to figure out what's about to happen, but I don't think any of us really know.

Me (turning to Greg, who's still holding the orange Tootsie Roll Pop in his hand): "So were you envisioning your guests would disrobe themselves, or would you take their clothes off for them? What's the protocol here?"

Greg (still looking a little awe-struck to be honest): "Oh. Uh... I think they would take off their own clothes?"

I turn to Maddie, and god bless her, she immediately pops open the top button of her jeans while staring right at Greg. She is absolutely bringing it!

She then works her pants down and slides them off, and now we can all see that she's wearing a pair of light turquoise underwear. They appear to be cotton, and are otherwise pretty non-descript besides the color.

Once her jeans are off, she then lifts the lightweight v-neck sweater she had been wearing up and over her head, cross-handed. This reveals the white tank undershirt she has on underneath. And after a brief pause, almost as if she's looking for confirmation that she should keep going, she again looks over at Greg. My boyfriend is still sitting in his chair holding that damn lollipop, but he's leaning forward as if he's absolutely captivated.

Maddie (to Greg as she begins reaching down to her feet): "Didn't want you to think I was trying to break your no socks rule."

And as she's saying this, she begins taking off the two ankle-high socks she had been wearing, before tossing them to the floor. All the while, she's keeping direct eye contact with Greg.

Greg (giving off a nervy smile): "Oh, you remember that?"

Remember that? It was like 20 minutes ago, Dude.

Maddie (answering, but with a pretty noticeable crack in her voice as she says this): "Yeah, I was paying attention."

Oh my god. The shake in her voice just now. She clearly is so unbelievably nervous. But she obviously is trying to hide it, because she has this swagger about her. It's so hot to think about that dichotomy going on inside of her head right now.

You know what's going on inside of me? My heart is racing like a motherfucker, that's what. But even so, I'm guessing I'm actually the calmest of the three of us here, so I can't even imagine what these other two are feeling.

Maddie, to her credit though, isn't stopping. Now that her socks are off, she returns to her other garments and smoothy lifts her white tank top up and over her head. In the process, she reveals a simple, beige padded bra. And while seeing her pale, slender upper body with just a bra on is pretty noteworthy, there's something else about her I notice.

As I said before, her underwear is a pretty shade of turquoise blue, but there's an unmistakable dark blue oval shaped spot on the under side of them. It's right where the garment is meeting the couch cushions, so it's a little hard to tell how big the spot is, but I know a wet spot when I see one, and that's clearly a sign that young Madison's juices are literally flowing right now. Holy fuck.

And Holy fuck indeed, here we go. Maddie reaches behind her back and all of the sudden, she's topless. Her bra is off and on the floor next to the rest of her clothes, and all she has on now is the pair of half soaked, light blue underwear. She's just sitting here half-naked on my couch, looking like the most precious, alluring, nubile creature god has ever created.

She looks so unbelievably innocent, too. Her eyes are darting back and forth between Greg and me, as now she does actually seem to be waiting on us for permission to proceed any further with her undressing.

A million thoughts are running through my mind. The first of which, is that Maddie's body is literally flawless. It is absolutely perfect, just the way it is. And it instantly brings back memories from when I was her age, and believe it or not, actually looked like that too.

The smooth perfect skin, with nary a mole, skin tag, or Varicose vein in sight. My current body, with all its inevitable imperfections that comes with age, can't possibly compare.

Her breasts, while not large by any means, are so perfectly round, perky, and cheerful. They clearly haven't had to experience the painful joy of breastfeeding a gnawing, starving, finicky baby for eight full months like mine did. And then there are her lovely nipples. They look so soft and delicate, and as they sit atop her plump little boobs, their light pink fleshy tone blends right in with her fair skin, that it's almost hard to decipher where her areolas end, and the rest of her boobs begin.

I'm so goddamn jealous. And so fucking regretful. I had that body once, and I hate the fact that I did nothing with it. I was so shy, timid, and introverted during my teenage years, and now all I can think about is what a waste that was. If only I could be a teen again and have that wonderful gift of youth one more time, I would act so differently.

I definitely wouldn't waste my wonderful body the second time around. I wouldn't be afraid. If I saw a boy I thought was cute, I'd come right out and tell him. If an older man made an inappropriate comment to me, I'd immediately call his bluff and give him a flirty response right back. I'd hook up with all sorts of boys at my school, and fuck plenty of dirty old men three times my age. And I would love every single second of it.

But you know what? I'm all talk. Because I had my chance to do those sorts of things when I was younger, and the crazy thing is, I even wanted to. I thought about sex all the fucking time when I was Maddie's age, and I even remember specific comments here or there that showed people were thinking about me in that way, too. And yet armed with a glorious, young, 18-year-old body, and a sexual curiosity that I'm only now starting to the let the world see, I did nothing. Zilch. Nada. Four years of high school, and I didn't kiss a single boy, even once.

But look at Maddie. What a fucking rockstar she is. She's sitting half-naked in front of her 37-year-old basketball coach and his 41-year-old cuck queening girlfriend, and for all we know she might even be more comfortable with this situation than we are.

The crazy thing is, it's possible this is the first time anyone's ever seen her naked too, and she just stripped down in front of us, like it was no big deal at all. Yeah, yeah, I know she had sex two times with some kid named William, but she probably wasn't sitting on a couch in front of a crowd under full lighting like she is right now. Sure, she's got that timid smile on, but it's still a smile!

Okay, it's time to do this. And it seems like Maddie is definitely waiting for one of us to make the next move here.

Me (turning to Greg): "I know I asked you a moment ago what your protocol was, but I think you need to get down there and take off Maddie's underwear yourself."

Greg no longer looks unsure, as he almost immediately stands up from his chair after I say this. Once he's up, I see him look down at his hand and realize he's still holding that orange Tootsie Roll Pop.

He stops and looks at me.

Me (to Greg): "What do you think? Time to give that to her?"

Greg doesn't say anything, but he starts slowly walking over to the couch, kneels down in front of this young, adorable, topless girl, and then he hands her the lollipop.

Maddie (very quietly): "Thanks."

Maddie places the piece of candy down by her side before timidly returning her hands to her lap. Greg meanwhile, wastes no time in making first contact with her as he gently places his hands on each of her two cute, little knees.

I can't believe this is actually happening.

My boyfriend, one of the nicest and most moral and principled people I've ever met, is about to cross a line in which there truly is no going back. And in the process, he is going to put every part of his life, career, and reputation in jeopardy. And he's

going to do it for one reason, and one reason only, lust.

There's no long term payoff here. Any benefit he's getting out of doing this is going to be extremely short lived. Maybe this is a tonight only thing, or maybe there will be a few nights of unbelievably satisfying sexual bliss between him and his absolute most favorite student. But either way, the illicit nature of this tryst pretty much guarantees that Greg and Maddie will never end up in a long term relationship together.

But I'm sure Greg realizes this, and I'm sure he's not fooling himself into believing it could ever be anything more. In fact, knowing my boyfriend, I'm sure he's also well aware of what the cost of doing this will be. So the only question left in his mind, is whether the pure joy and unimaginable satisfaction is going to be worth the price he pays.

It couldn't have been an easy question for him to answer, because there's no doubt the cost will be high. He's going to have moments of regret. He's going to panic. He's going to worry for years that it's only a matter time until their secret comes out. That people will find out what he did. That his career will be over. But even with all of that, he seems to have made up his mind.

Part of me honestly feels a little bad that I'm an accomplice to this. That I'm helping Greg go down this path knowing full well what it's going to do to him. But then there's another part of me that knows that Greg is a big boy, and he can make his own decisions. Does that make me a horrible person? I don't think so. I'm certainly no Mother Theresa here, but then again, who is. All I know is, it seems like Greg wants this, I'm pretty sure Maddie wants this, and I absolutely fucking want this, so we're going to do it.

And with that, Greg takes the knees of his precious little backup shooting guard, and he tilts her entire lower body up and into the air. Maddie's head is forced back onto the cushions of my couch, and despite having a level of body fat that most females would kill for, her stomach bunches up into cute, little rolls of pudge. And oh my fucking god...

Remember before how I mentioned I could see a dark little wet spot on Madison's turquoise undergarment? Well I was mistaken. It is most definitely not a little spot. As once Greg tilts Maddie's legs back, he unveils an enormous dark blue patch of soaking wet cotton underwear. I'm talking roughly the size and shape of an adult male's clenched fist, and it's so wet that we can actually see the sheen of it reflecting off of my living room lights.

Greg (seeing this evidence of Madison's extreme amount of natural lubrication): "Oh my holy god."

Maddie (with her head now looking between her raised up legs): "What is it? I'm sorry whatever it is..."

Greg (so quietly we can barely hear him): "Don't apologize."

Greg then removes his hands from the inside of Maddie's knees and brings them down to take ahold of her completely drenched underwear. He grabs the back of the waistband and begins to slide them over her butt and up and off her legs. And as he does, all I can think of his how unbelievably graphic this entire scene is. And I love it. I hope I never forget this image for the rest of my life.

Maybe it's because I'm realizing right this second that I've never actually seen another female's anatomy in real life before. I mean, sure, I've been around other naked women a number of times, but I've just never been in a position to see them sitting on a couch with their legs spread open like this! Holy fuck is this intense.

I immediately fixate on Madison's exposed asshole as it peaks out from behind the two whitest, softest butt checks you could ever imagine. And then as Greg continues to lift her underwear up, I'm introduced to her naked vagina. It's so pink and fleshy, and I can see all of her lips. The little inner flaps, the big, soft outer ones. I can even see some of the dark, inner redness of her opening. But then oh my god, everything I just mentioned, it all takes a backseat to this girl's extraordinary amount of wetness. It's like nothing I've ever seen, and perhaps didn't even know was possible.

In fact, it's not even like a normal wetness, as it's more like a slime than a liquid. It's a heavy, thick, gooey mess, and it's everywhere. In fact, as Greg continues to raise Maddie's underwear up and off her legs, there's a thin web of this pussy mucus valiantly attempting to keep ahold of her departing undies. But obviously it can only stretch so far, and the bond is finally broken as Greg slides the pair past Maddie's knees, down her legs, and eventually off her feet.

My boyfriend then tosses the soaking wet undergarment aside and returns to his position on the floor right between Madison's partially spread open legs. But they're not slightly ajar for long, as Greg takes his hands and rather abruptly forces his young student into a very wide, completely spread-eagled position. Holy fuck. His face is right in front of her opened up pussy. He's going to do this.

And for all that wetness that got carried away with her underwear, it's clear that was only the tip of the iceberg, because Maddie's vagina is still just so unbelievably sloppy. She has these sweet, innocent blonde pubes, and while the ones up on her mound are a beautiful shade of gold, the hairs down below near her actual vagina, are much darker and all clamped together, simply because like everything else in the region, they're soaking wet.

While I'm taking this whole scene in, I suddenly realize that we're actually forgetting one very important component. The Tootsie Roll Pop! So I hop up, and as I walk over to Maddie on the couch, I see her eyes timidly follow me as I come towards her. Greg doesn't seem to notice me one bit though, as honestly he looks like he's about to dive in and just start eating her pussy any second now. But once I get to Maddie's side and pick up that orange lollipop I had originally worked so hard to procure, I notice I now have Greg's attention.