Coach's Cutie Ch. 06

Coach's Cutie - Chapter 6: Two-and-a-Half Fantasies

In my world, Sunday evenings are reserved for getting everything squared away for the week ahead. I'll tidy up my apartment, vacuum all the floors, wipe down the appliances and counters, and even change and wash the sheets on my bed. It's probably overkill and a little OCD, but It's my little routine and I enjoy it. It also means I'll usually try to avoid making any significant plans for Sunday nights, as doing so would obviously interfere with my chores.

Tonight though, I was willing to make an exception. And that's because Maddie is coming over!

You see, a few weeks back, my boyfriend Greg confided in me that he has a huge crush on this girl named Madison, and ever since then I've been obsessed with the idea of the two of them getting together. But Maddie isn't just a student at the high school where Greg teaches, she's also a player on the basketball team that he coaches. And so as you can imagine, even though she is officially 18, it's pretty obvious that Greg's undeniable lust for this girl is constantly at war internally with a very reasonable concern for his career as an educator.

While Greg and I had spent a fair amount of time discussing his feelings for Maddie over the past few weeks, it was always from more of a hypothetical standpoint. Like if we were simply discussing some far-fetched fantasy that wasn't likely to ever come true. But in my mind, everything changed once I got the chance to know Madison a little better. Specifically, once I found out that she's every bit as infatuated with my boyfriend, as he is with her!

I finally confided all of this to Greg last night. I told him about the secret friendship I had started with Maddie, the fact that I confirmed she has the hots for him too, and then just the reiteration of how badly I wanted to watch him eat her out and make sweet love to her petite little body. And granted, there was a huge misunderstanding at first while I tried to confess all of this to him. But in the end, Greg ended up being quite receptive to the idea that something physical could actually happen between the two of them.

And that's why I feel the need to act now, as in tonight. I'm worried that any acceptance that Greg has for potentially exploring something with Maddie is tenuous as best, so I don't want to waste any time in trying to make this fantasy come to fruition.

Maddie's and my budding friendship has been thanks to this adorable corgi named Cassie, who I decided to foster after Maddie's family was forced to give her up. It's a long story, but suffice to say I sent Madison a text this afternoon playfully (manipulatively?) mentioning that I could tell Cassie was missing her, and asked if she'd have any interest in hanging out tonight. She immediately responded that seeing Cassie sounded much more appealing than studying for some physics test she has coming up, and that she'd be by around 7.

With Maddie confirmed in for a rendezvous at my place, the only question left was Greg. While I was pretty confident that he wouldn't completely back out of a meetup at this point, I wasn't sure if it made more sense for him to come over beforehand and be here when Maddie arrived, or for him to plan on coming over after she was already here. I actually decided on the latter, as I figure it would be good for me to have a few minutes with Madison alone, to almost test the waters, so to speak.

You see, not only do I have to worry about Greg panicking and getting cold feet over this whole ordeal, but who knows if Maddie is even going to be interested in it herself. I do know she has a legitimately huge crush on her teacher and coach, but it's still quite a leap to go from having those sorts of feelings, to actually hooking up with a man over twice your own age. Not to mention, being comfortable enough to do it all in front of his weirdo, sex-obsessed girlfriend! :P

So yeah, I definitely want to make a few subtle innuendos to Maddie when she first gets here, just to see if I can pick up on any warning signs that might warrant bailing on this whole escapade before it even begins.

Since I have no idea how late this meetup could potentially go, I make sure to get all of my Sunday evening chores done ahead of time. Being the eternal optimist that I am, I figure it's definitely important to have freshly clean sheets on the bed too, just in case everything goes swimmingly and we all end up in those sheets later tonight.

Once I'm done getting my place ready, I actually sit down to eat a little dinner, but I find that I'm so nervous and excited that I barely have any sort of an appetite! I finish up, get the leftovers into the fridge, and then at 7:02pm I hear a knock at my door. Cassie starts barking excitedly, and as expected, it's Madison. Cassie greets her with a number of jumps and an excessively waggy tail, while Maddie and I exchange hellos.

Maddie (bending over to greet her favorite pup): "Hey there Sweetie. Yes, I missed you! I missed you too!"

Me (as I head over to my kitchen area): "How was your weekend? Do anything fun?"

Maddie (as she sits down with Cassie on my couch): "Not really actually. Like I mentioned in my text, I've had a fair amount of studying to do, so mainly just that."

Me: "Ah yes, I remember those days. I was always the type who would be so anxious about tests, and then in the end I would end up waaaaaaay over studying."

Maddie (chuckling): "Yeah, that's pretty much how I am too. Ha. I guess it's better than not studying at all and failing."

Me (laughing): "Definitely. So can I get you something to drink?"

Maddie (chipper as can be): "Sure, a glass of ice water would be great!"

Me (as I start uncorking a bottle of Trader Joe's Pinot): "I'm actually having a little wine. Would you like some of that instead?"

I'm very curious to see how she responds here as I've never offered her a real drink before.

Maddie (clearly caught off guard): "Oh. Uhhh...."

Me (trying to be chill): "It's not a big deal either way, just thought after a weekend of studying you could use a glass, ha. But maybe you don't ever drink, which obviously is fine too."

Maddie: "Oh, yeah. No, I do drink from time to time with my friends. Nothing crazy though."

Interesting.

Maddie (looking at my glass as I pour it): "Is there any chance you have any white wine though?"

Me: "I do. I have an already opened bottle of Chardonnay in the fridge. Does that work?"

Maddie: "Yeah, sure! I'll take a small glass, if you have some to spare."

Ha, some to spare. At this point, even if I didn't have any white wine, I would've happily run to the grocery store to get some for her. But this is perfect.

I pour Madison a very reasonable glass of the Chardonnay and put the bottle back in the fridge. I join her and Cassie in the living room and sit down in a chair across from the two of them on the couch.

Me (raising my glass to hers): "Cheers!"

Maddie smiles, clinks her glass to mine and then takes her first sip. For whatever reason, she seems to be in an exceptionally good mood tonight, and I love the fact she accepted my offer on the wine. But what happens next though is going to be the real test.

Me: "So I hope it's okay, but I think Coach Greg might stop by in a little bit."

Maddie (chuckling while looking down to acknowledge the glass of wine she's holding): "Oh, ha."

Me: "But I did give him the heads up that you'd probably be here as well."

Maddie (now looking a little confused): "Oh. You're serious? I thought you were just making a joke because of the..."

Maddie (now holding her glass back up to me): "...you know... the wine."

Geez! Why does this keep happening?!? Everybody always thinks I'm bullshitting them when I'm actually telling them the truth! It is something I'm doing?? Is it the way I say things?

Me: "Oh my gosh! No, sorry. Yeah he really might be stopping by."

Me (now pointing at Maddie's wine): "But don't worry about this. He won't care. And besides, he thinks the world of you."

Maddie (after taking another sip): "He does?"

In all honesty, I have no idea if Greg is going to be annoyed that I gave Maddie some wine, but I figure even if he is, he'll be discreet about it and just blame me after the fact.

Me: "Yeah, I told him yesterday that it turns out I was fostering your old dog, and he was just going on and on about what a great person you were. How hard working, smart, and nice, and funny..."

...and adorable you are, and what a cute, sexy, and unbelievably fuckable body you have, and how he would give his left arm for the chance to bury his face between your skinny, little legs. Ha, I wish I could tell her all of that. In due time, Becca. In due time.

Maddie: "He really said I was funny??"

Me (blatantly lying because yeah, of all the things he's said about her I don't think he ever actually said that): "Yeah, he did. I swear."

Maddie (chuckling): "I think we just have the same sense of humor, that's all."

Me: "Well, probably. But yeah, I just think in Coach Greg's eyes..."

Me (smirking): "...sorry, in Coach Dream's eyes... you can do no wrong. So I don't think you need to worry at all about having that glass of..."

Knock, knock, knock, knock.

Greg has come over to my place enough times that I can recognize his distinctive four quick knocks a mile away. He's here. But what the fuck is he doing here so early?

I check my phone. It's 7:14! I had told him to come by between 7:30 and 7:45!?! What is he doing here now?? Is he that excited for tonight to take place, and can't control himself? Or is it just that he's super paranoid and is borderline freaking out?

At least things with Maddie are going well, because if they weren't and I had wanted to bail on the whole plan, I wouldn't have been able to warn him not to come!

Me (as I stand up): "Speak of the devil, I think that might be the coach right now."

I walk over and answer the door. Greg's there and I welcome him in. He immediately sees Maddie on the couch with Cassie on her lap, and then I'm pretty sure I see him notice her glass of wine.

Me (probably kind of panicking here, but oh well): "That's all me. I told Maddie I don't like drinking alone and I pressured her into having a glass with me."

Maddie (kind of giggling while sticking up for me): "That's not true, she didn't..."

Greg (not even hearing Maddie and instead kind of looking at me sternly): "What are you talking about?"

Shit. Is he pissed? He's pissed.

Greg (then breaking out into a smirk): "You drink alone all the time!"

Okay phew, that was a joke. But ouch, that was kind of a decent burn he just hit me with! He's definitely right though, I do drink alone way more often than one probably should.

Greg (turning to Maddie now): "It's totally fine. Just make sure you're not hungover for practice tomorrow. That's all I care about!"

Oh snap. As good a mood as Madison is in, I think Greg might be even more chipper! This is fantastic, and very promising.

Me (figuring why not?): "What can I get you, Hon, red or white?"

Greg (who again, rarely ever drinks because of the whole dead wife from a drunk driver thing): "I'll go red."

Fantastic! Let's get this party started.

I pour Greg a glass of the Pinot Noir I'm drinking, and then we each have a seat in the two chairs opposite Maddie (and Cassie the dog) on the couch.

Me: "Well... how about this? This is quite the unexpected threesome..."

Me (realizing what I just said and that I swear to god wasn't even intending to): "...all hanging out together on a Sunday evening."

Greg gives me a look that simply says, reallly?!? But then he quickly gets passed my Freudian Slip as we start chatting about school, their basketball team, and a few gossipy subjects related to students both Greg and Maddie know. I feel a little left out from the conversation, but I love that we're talking about topics that are at least a little bit suggestive.

Greg eventually finishes his glass of wine, and as he gets up to pour himself a refill (another good sign), I ask him if he could top me off as well. I then see Maddie is almost done with hers, and ask if she would also like some more.

Greg (interjecting): "Maddie, how did you get here, did you drive?"

Oh god, I know where this is going.

Maddie: "Yeah, I'm parked right out on the street."

Greg: "Okay, let's hold off then on a refill for you. But maybe in a little bit."

Lame. But oh well. It's not worth pushing back on. Maddie doesn't seem to care that much either, so it's fine.

Greg hands me my new glass of wine, and then he mentions that he has to use the bathroom. Once he leaves and it's just the two of us, I see Maddie give me kind of a funny look. It's almost as if she has something to tell me, but doesn't know how to say it.

Me (with my curiosity getting the best of me): "What? What is it??"

Maddie: "Oh..."

Maddie (after pausing): "It's nothing. Forget it."

Me (definitely not going to let this drop now after she said that): "No seriously, what is it? Whatever it is, you can tell me."

Maddie (looking down as if she's nervous): "No, I was just going to ask you something, but it's almost certainly going to be so totally random, that you'll think I was so weird for asking it."

Me: "Well now I really need to know! Seriously, Maddie, whatever it is I'm sure it isn't weird and it's totally fine to ask."

What is she going to ask?? It is something sexual in nature?!? I sure hope so! Fingers crossed.

Maddie (very quietly as if to make sure Greg can't hear): "Are you guys like..."

Me (waiting for her to finish): "Are we like...??"

Maddie (even quieter): "Are you guys... like swingers?"

Ha. Awesome. This is fantastic.

I can't help but laugh.

Me: "Ha. That is not a ridiculous question at all. That's awesome."

Me (quickly clarifying): "We aren't swingers though. At least, I've definitely never done anything like that before, and I'm pretty sure Coach Greg hasn't either."

Maddie: "Oh, sorry, that was definitely a stupid question."

Me: "It really wasn't. Believe me... more than you know."

After I say that, I hear the toilet flush in the bathroom, so I figure we probably only have about 30 seconds or so before Greg comes back. In the interim, all I can think about is how Maddie asking me if we were swingers is such an interesting question on so many levels.

First off, it means she's once again thinking about, and clearly willing to talk about, topics related to sex. But more importantly, if she thought that we could be swingers, then she must've gotten some impression or hunch that we might somehow be trying to seduce her? She's obviously not off base at all, so kudos to her on her intuition. But if she did think that, and she's not freaking out about it, which she doesn't seem to be, then that sure seems like a really, really, good sign, right?

I do want to make one more comment before Greg rejoins us, though. Nothing too over-the-top, but something that at least alludes to our potential intentions tonight.

Me (kinda quietly as if to imply I don't want Greg to hear): "but you know Maddie, there is a first time for everything..."

I smile, and I see Maddie react by opening her eyes kind of wide. She certainly doesn't look offended or anything, mostly just surprised and probably slightly intrigued as to what I meant by saying that. I love it.

I hear Greg coming out of the bathroom, and as he's walking over, I raise my glass up to Maddie's for another cheers. She gets a slightly mischievous look on her face, and then clinks my glass with hers, except now I see that she's completely empty.

Me (taking Maddie's glass): "It's been long enough. Time for a refill."

I head to the fridge to get some more Chardonnay for Madison, and as I'm walking back to rejoin the other two, I decide it's definitely time to take things up a notch.

Me: "Who wants to play a game?"

I have something in mind that I want to do, but I realize as soon as I say this, that calling it a game was probably a poor choice of words.

Greg (seeming very agreeable): "Sure, what game were you..."

Me (interrupting): "Sorry... it's not actually a game."

Me (as I hand Maddie her new glass of wine and have a seat): "Here's what I think we should do. I think we should take turns each sharing a fantasy of ours. But don't worry, I'll go first."

Greg (giving me a very perplexed look): "Becca, I'm not sure that's very appropriate... do you?"

Honestly, if it wasn't for the brief exchange that Maddie and I just had while Greg was in the bathroom, I'd probably feel the same way. But there was just something about that swingers question she asked, and how she responded, that makes me think she knows full well what Greg and I are up to tonight. She may not be the most experienced person sexually, but I'm coming to realize that she's definitely not as innocent as we had first thought, either.

Me (turning to Madison on the couch): "Maddie, are you okay with my suggestion? It's absolutely fine if you're not, and we can do something else."

Maddie (after taking another sip of her wine): "I'm definitely okay with it."

I look over at Greg, and he looks quite surprised at Maddie's answer. Pleasantly surprised, though.

Greg: "Oh. Okay. Maddie, yeah, if you're fine, then I'm fine."

Yeah, no shit, Sherlock. You'd better be fine with it.

Me (placing my own wine glass down onto the coffee table before cracking my knuckles): "Okay great. So let's begin..."

I see Greg and Madison kind of lean forward ever so slightly as if they're both very interested to hear what I'm about to say. In fact, the only one who couldn't care less about this story is Cassie the dog, as she's now contently snoring away on the couch next to Madison. But even I'm a little curious to know what I'm about to tell them, and it's my fantasy! Obviously I have a general idea of this erotic vision I want to portray here, but I just don't know how good a job I'm going to do conveying it to them. But here goes nothing...

Me: "So my fantasy is quite hypothetical, as it specifically involves me dating a college professor. Ideally, a psychology professor."

Greg (with a furrowed brow): "Ouch. Seriously? That's pretty harsh."

Me (confused): "What? What's harsh?? I haven't even gotten to the fantasy yet."

Greg (with a little chuckle): "I mean, a college professor is basically just a better version of a high school teacher, right? Like I said, kinda harsh."

Me (realizing the connection): "Oh, ha. I swear I hadn't even thought of that. It's definitely not a critique of your profession, Hon."

Maddie (laughing and turning to Greg): "I actually was thinking the same thing as soon as she said that."

Greg (looking back at Maddie): "Thank you!"

Well, if nothing else, I like how the two of them are bonding over my supposed slight of Greg.

Me: "Anyhoo, okay yeah, sorry. It's nothing personal against your being a high school teacher or anything, but for this fantasy it just makes sense that he's a college professor."

Me (looking right at Greg): "Is that okay?"

Greg (smirking): "That's fine. Go ahead, Dear."

Me: "So picture this... It's the last day of classes before Winter break, and a lot of the students have already left campus and gone home. In fact, a number of teachers actually canceled their classes for today, just so they could get an early start on their break as well. But my boyfriend decided to still have his lecture, and that's because this particular class is going to be a very special present for me."

Both Maddie and Greg look quite interested so far.

Me: "His class is in one of those huge lecture halls with a ton of seats. And it's so big that it even has a stage. He invites me to come, but he has me standing backstage and out of sight from his students, but I can see him lecturing. He told me this class was going to be a surprise for me, but he didn't say how. Needless to say, I'm super curious to find out what he has planned."