Coach's Cutie Ch. 05

Coach's Cutie - Chapter 5: Smoothing Things Over

I'm so excited to tell Greg everything I found out tonight! Now I just have to figure out the best way to do it, because I'll have no choice but to admit what I've been up to.

You see, these last two weeks I've basically been sneaking around behind my boyfriend's back in order to befriend his adorable, forbidden crush, Maddie. And while this sort of low-level deception is definitely out of character for me, I feel like in this instance the ends have kind of justified the means? All I know is, I found out tons of new information about this girl, and now I'm just dying to fill Greg in on everything I learned, even if that means confessing exactly how I came across this salacious info in the first place.

Greg knows that for the past two weeks I've been fostering this sweet, little corgi named Cassie. But what he doesn't know, is that this dog had previously been staying with Maddie's family. When I decided to take Cassie home with me, I had assumed it would give me a chance to get to know Madison a little better, and I was definitely looking forward to that. But if I'm being honest, I didn't actually expect it would lead to anything happening between my boyfriend, who by the way is a high school basketball coach, and this 18-year-old player of his.

But then I started to get to know Maddie, and not only did I confirm that she also has a huge crush on Greg, but amazingly, the one sexual act she's most curious about experiencing, just happens to be Greg's favorite thing in the entire world to do! I mean, this has to happen now, right?? She deserves to experience getting eaten out by someone who loves doing it, while he deserves to lick the pussy of this innocent, little, blonde cutie that he absolutely adores. Meanwhile, I deserve to get to watch it all go down, especially if I'm the one who ends up making it happen!

The problem is, I know Greg is going to freak the fuck out as soon as I tell him I've been hanging out with Madison. There's just no way around it. He's too paranoid about losing his job, his career, and basically everything he's ever worked for, and when I phrase it like that, he's obviously not wrong to feel that way.

But I believe that sometimes in life, you just have to say 'fuck it' and live for the moment. I know for a fact that there's nothing his body and mind want more than to make unbridled, passionate love to this one particular teenage girl. He just cherishes her like nothing I've ever seen.

Calling his feelings for Maddie a crush, just isn't doing it justice. The little comments he's made, the way he talks about her when he lets his guard down, it's all so clear. I can tell there's a level of desire within him that is really quite extraordinary. And seeing that amount of passion come from someone you care about, makes it really hard for you not to want that for them!

Okay, so I'm going to do this. I'm going to tell him everything.

Me (grabbing my phone to text Greg): "hey you still up?"

It's not even 10pm yet, so I doubt Greg is already in bed, let alone asleep. But for whatever reason, I don't get an immediate response.

Me (following up with another text): "I wanna chat about something but probably best to do it in person."

I send that off, but still nothing. As soon as I reread that second text though, I realize it could easily be interpreted kind of ominously!

Me (quickly sending a third message): "nothing bad though! Not planning to break up with you or anything :)"

Oh god. Still no reply back and now I officially sound like a crazy person! What did I just do?? Fuck.

Okay, No more sending texts. I just have to wait for a response now, but I wonder why he's not replying?? We've definitely been a little off this week, for lack of a better term, so I hope he's not too annoyed at me. If he is, I'm sure my barrage of messages just now joking about not breaking up won't help! Oh god.

This distance between us lately is 100% my fault too, as it's all directly related to my hanging out with Maddie so much. But there's no way Greg could've known about that, so I wonder if he's been rationalizing our minor rough patch in some other way? On the other hand, maybe he hasn't even noticed?

I'm hoping it's the latter, and everything's business as usual from his perspective. Either way though, I just really want to come clean about everything related to Maddie. It'll be a relief to finally get that off my chest, as it's definitely been weighing on me. No more secrets!

As much as I'm looking forward to relieving myself of that guilt, I'm also so genuinely excited to share the news of Maddie's mutual feelings for him. And oh yeah, I also cannot wait to tease him about that glorious nickname, Coach Dream, the girls on the basketball team all call him behind his back!

So all of that is obviously exciting, but I am still worried about how he's going to feel about Maddie's and my new friendship, though. The good news is, despite the fact that she and I did discuss her sex life, I haven't let on at all about what Greg thinks of her. And besides, the whole reason I know what I do about her sexual history is because she volunteered that information to me! I certainly didn't go prying anything out of her! I'll have to make that crystal clear to Greg, so he doesn't accuse me of somehow grooming her or some shit like that.

Now I just need Greg to text me back so I can head over there and get this conversation started! But apparently, it's not going to be tonight, as he never responds and eventually I have to call it a night.

I sleep pretty well all things considered, but when I wake up in the morning, there's still no text back from him. I hop in the shower, and then afterwards as I'm drying myself off, I hear my phone vibrate on my nightstand. Finally! It's a reply from Greg.

Greg's text: "hey sorry - went to bed early and just seeing this. everything ok? wanna order in dinner tonight? either your place or mine is fine with me, but feeling mexican if youre up for it"

Phew. Seems like everything's good. It was just an early bedtime for him after all, nothing more.

My reply: "yeah sounds great! I'll swing by your place around 6?"

In response, Greg sends me that giant thumbs up emoji guys seem to love using.

Okay, this is good, disaster averted. I don't know why I get so panicky sometimes! But still, it's obviously super important that tonight goes well. And as I'm thinking this, I get an idea. There's something I've been meaning to do, specifically for Greg, as kind of a present. I had just never gotten around to doing it, but this would be the perfect opportunity.

I believe I've mentioned this before, but I think I do a decent job keeping my bikini region consistently shaved. I've always preferred the look of a hairless crotch over any sort of pubic hair, whether that be a small patch, strip, or god forbid a full bush! Ha. But anyway, a bald vagina seems to be Greg's preference too, and considering how much time he spends down there, I definitely value his opinion.

But as nice as a cleanly shaved pussy is, it's not quite the same as a waxed one. The truth is, I used to get my bikini region waxed pretty consistently when I was first separated from my ex-husband. But between then and now, I briefly dated a man who actually asked me to grow my hair out, which I was happy to do for him. But then after we broke up, I just resorted to shaving it myself rather than waxing.

Part of it is just the cost, as I'm constantly in a battle to save a few dollars here and there. There's also an element of laziness, as it takes effort to call and book an appointment. But with Greg's love of licking me and my desire to butter him up before this talk, what better day than today to finally surprise him with a freshly waxed pussy!

So I have this Thai lady I used to go to. Her name is Anong, and in addition to being proficient at her craft, she's also hilarious. She always did a great job being extremely thorough, meaning no stragglers left behind. But she also does her best to minimize the number of pulls, meaning as little pain as possible for me in the whole process.

What made her so funny though, is she's this tiny, older Asian lady, and perhaps not surprisingly, she has a pretty strong accent. But she would always refer to my vagina as my 'coochie' and my butt crack as my 'poochie'. And just hearing her say those words, while she's contorting me every which way, would never cease to crack me up (no pun intended).

So while I'm at the animal shelter on my typical Saturday shift, I call and succeed in making an appointment with good old Anong for my lunch break. Ideally, with all the redness that can sometimes occur right after the treatment, I'd probably want to have more than a few hours post waxing before unveiling the finished product to Greg. But unfortunately in this case, I don't think I have that luxury.

The good news is, my waxing session goes smoothly (pun definitely intended) and I don't think I'll end up with much discoloration. Good old Anong did interrogate me as to while I hadn't been there in so long, and even borderline accused me of going to some Korean waxing place that I had never even heard of, but I assured her I would never cheat on her! Ha.

After I finish my shift volunteering at the shelter, I head home to shower and freshen up. I get nice and clean, put on a cute new top I recently ordered online, and then I head over to Greg's place for our Mexican dinner and this big confession of mine.

When I arrive, my boyfriend offers me a glass of wine, which I happily accept. Greg, not surprisingly, abstains from drinking anything alcoholic and instead pours himself a seltzer over ice. Our food comes shortly after I get there, as he had taken care of the ordering ahead of time. My fish tacos are fantastic, and Greg got one of those salads in a giant fried tortilla shell, which also appears to be quite tasty.

While we eat, we put on an episode of Ted Lasso, which is the show we're currently watching. Like always, I ask Greg to turn on the subtitles because I have such trouble understanding the British accents, and while I'm pretty sure he's secretly annoyed that I always ask him to do that, he happily obliges.

We share some good laughs though, as I love me some Roy Kent, and everything seems pretty normal, despite the lingering feelings I've had that we've been a little off. When the initial episode we started watching ends, Greg actually brings up the fact that I had mentioned wanting to talk to him about something, but I let him know it's probably more of a bedtime conversation. I say it with a little bit of a seductive tone, and that seems to pique his interest.

We end up watching a couple more episodes before deciding to call it a night. As we're getting ready for bed, I manage to change into my sleeping attire without Greg noticing my freshly waxed nether regions, but as we both finish up brushing our teeth, I figure it's time to finally unveil my little surprise present.

After spitting my remaining bits of toothpaste into the sink and rinsing my mouth out with water, I turn to Greg and give him a mischievous smile.

Greg (after finishing rinsing out his own mouth): "What? What're you grinning about?"

I don't say anything, but I walk over next to Greg and put my hands around his waist.

Greg (after giving me a small peck): "Oh, we're doing this tonight? I could definitely be up for that."

I take Greg's right hand, turn it palm side out, and slide it down the front of my shorts and into my crotch.

Greg (with his eyes widening): "Oh wow. It's really smooth. Did you like just shave or something?"

I still don't say a word, but I shake my head no.

Greg (smiling but looking a little confused): "If you didn't shave, then why is it... wow... it's reaaaaaally smooth. You must've just shaved?!? How did you do that??"

Me (finally breaking my silence): "I wanted to surprise you, so I went and got it waxed."

Greg (clearly excited, just as I had hoped): "Oh wow, really?!? What all did you get waxed??"

Me (grinning now, as I feel Greg's fingers starting to probe and explore my slick folds): "Everything."

Me (as I remove Greg's hand to lead us towards his bed): "You wanna see for yourself?"

Greg: "Oh my god, I would love to."

We head into the bedroom and Greg guides me down onto his bed's comforter. So far my plan is working to a T! Now I just need to figure out how to break the news about Maddie. I figure if we're right in the middle of having sex while I do it, he can't get that upset, right? A horny brain is definitely my ally here.

Once I'm fully lying on my back, Greg wastes no time in removing my shorts. I help him out by taking off the t-shirt I had just put on a minute ago, so now I'm lying spread eagled on top of his covers, completely naked. And as soon as Greg sees my freshly waxed coochie, as Anong would call it, he gets even more excited.

Greg (as he dives in right in front of my pussy): "Oh my god... it's so fucking smooth. I love it, Hon. Thanks for doing this."

Me (responding to Greg's nice comment): "My pleas..."

But before I can even finish my sentence, Greg's tongue darts right in between my lips and makes one long lick up my opening. At the same time, his hands take ahold of the inside of my knees and tilt my entire lower body up and towards the ceiling. And then without pausing, I feel Greg retreat down below and begin a second, even longer lick with his tongue. This time he starts at the bottom of my butt crack and traverses directly over my asshole, up my taint, into my vagina, and then up and over my clit.

Greg (with a huge grin on his face that's starting to show a little bit of a glisten): "I looooooove how smooth and hairless it all is."

I smile back at my boyfriend, and then we apparently both get the same idea as we simultaneously pull the covers aside and climb in underneath the sheets. Once we're repositioned on the bed, Greg moves his head back down towards my crotch, and I reach out to start gently running my fingers through his lovely, short brown hair. My boyfriend's tongue then returns home to my spread-open pussy, and I figure it's time to do this.

I think I'll start by first telling him all the juicy details I learned about Madison, and then later on I can explain how I came across this information.

Me (as I continue to stroke Greg's head): "So it turns out, our girl Maddie isn't a virgin after all..."

As I say this, Greg immediately stops eating me and just kind of peers up from behind my bare mound.

Greg (kind of skeptically): "What do you mean?"

Me (smiling mischievously): "I mean she's had sex before. Twice, in fact."

Greg (after taking a moment to process what I said): "Okaaaaaay? Who did she have sex with?"

Me: "This boy named Will. He's not a student at your school, so I'm guessing you don't know him."

Greg kind of nods, taking in this information, and then returns to eating me out. This time he's giving me small, light, sensual licks right around my opening. Then for the first time tonight, he slides a finger inside of me.

And it feels absolutely wonderful.

Me (softly): "Oh my god."

Greg (while fingering me): "So tell me about this Will guy... what's he like?"

Me (having to legitimately concentrate because it's not easy to form sentences right now with how good this feels): "It sounds like... that he's... kind of lame."

Me (continuing after losing my train of thought briefly): "Maddie doesn't even... even like him... that much."

Greg (while sitting himself up a little higher): "Oh really? So where'd you hear all of this?"

This is it. The real moment of truth. I look right into Greg's eyes while he continues to rhythmically slide his middle finger in and out of my vagina.

Me: "Maddie told me. We've been hanging out."

Greg's eyes open a little bit wider, but he doesn't freak out or anything, so that's definitely a positive.

Me (trying my best to distract him): "Oohhhhhh Hun, that feels so fucking good."

Greg: "Oh you have, have you?"

Me (figuring I might as well give him the full explanation): "Yeah, she's been coming over to hang out... hang out with that dog I'm fostering... Cassie. It turns out Cassie... used to be Maddie's dog."

Greg then abruptly pulls his finger out of me. Shit. Is he pissed?!? I don't know. All I know is he steps down off the bed, but then he proceeds to push his boxer briefs down his legs, before kicking them off to the side. Phew. He's not pissed. In fact, now he's climbing back up onto the bed, I think to start fucking me.

I'm still lying on the mattress spread-eagled, and as Greg moves overtop of me, I look down and see just how soaking wet I am, and how ridiculously hard he is.

Greg (as he lowers his face to be just above mine): "Well that's quite a coincidence, isn't it?"

Me (as I feel the tip of his fully-erect penis make contact with my vaginal lips): "It is..."

I have to admit, this is going about as well as I possibly could've hoped for. He hasn't freaked out, and he's about to make love to me, which I have to imagine is a really good sign. But I'd be lying if I said I wasn't at least a little bit surprised.

Me (timidly): "You're not mad?"

Greg (after chuckling): "No. Did you want me to be?"

Me: "No, not at all. I want you to be happy."

Greg: "Oh good..."

Then without warning, I feel Greg shove his rock-hard cock all the way up inside of me. And while he thrusts, he gives off a pretty loud, caveman-like grunt. Our pelvises collide with a loud smack, and then Greg forcefully grabs onto my hips so he can hold us tightly together.

While the initial entry was unexpected and a little rough, I absolutely love the fact that he's so into the moment. Plus, my pussy was already well lubricated at this point, so his sudden thrust wasn't too uncomfortable, all things considered.

And as Greg pulls back and then pushes forward to begin fucking me in rhythm, I figure I might as well continue filling Greg in on everything else I've learned.

Me (with Greg's face only inches front of mine): "So do you know who Maddie dated before this random Will kid?"

Greg (smiling and shaking his head no while he continues slowly grinding in and out of me): "No, I don't... but I'm dying to know."

Me (smirking now too as this is so much fun): "She dated Lucas. You know... Amanda's boyfriend?"

Greg: "Wow. I didn't know that. But that's very interesting. Who could've seen that coming?"

Me: "I know, right?!? The biggest stud in school... dating your precious, sweet, little, adorable Madison. How were you not aware?"

Greg (now moving his hands up to take ahold of mine and pin them back above my head): "That's a good question."

Greg (as he gives me an extra forceful thrust): "Maybe I haven't been stalking her as closely as I should've been."

Oh I like this. He's really taking this and running with it. Scratch that. I loooooove this.

Me: "You know what else I learned? That when Maddie and Lucas were dating, she was a little bit of a prude."

Greg (smiling): "That doesn't surprise me."

Me (breathing heavily now): "Yeah... you know what else isn't surprising? That Lucas really wanted to fuck her. But he also really wanted to eat her pussy. But Maddie was too scared to let him do either of those things."

Greg closes his eyes and moans as he continues to slowly make love to me.

Me: "But now, that's all she can think about. Getting her pussy licked, that is. She really, really wants to know what it feels like to get eaten out. To have a cute boy force her skinny little legs open and just go to town on her innocent, sweet vagina."

Greg immediately opens his eyes and gives me that look that indicates he's about to blow his load.

Greg (nonsensically): "Oh my fuck..."