Coach's Cutie Ch. 04

As Greg and I walk out into the parking lot to head our separate ways for the night, I make a comment about how at least there aren't any angry dads out here berating their daughters this time! Greg gives me a bare minimum chuckle, but that just makes me think he didn't find my joke funny at all. Ugh. We're definitely not in sync right now!

Even so, we kiss each other goodnight and get into our respective cars. As I place my bag onto the passenger's seat, I notice I have a text, though.

From Maddie: "any chance I can come hang with Cassie tonight?"

My reply: "Yeah, sure. Anytime from 8 on works!"

Okay this is good. This is perfect, in fact. I need to come clean, and I think it makes the most sense to tell Maddie first. And when I say 'come clean', I'm not talking about telling her everything, I just mean telling her that I'm dating her coach. That's the perfect first step, and then afterwards, I can figure out how I'm going to let Greg know about all of this.

Maddie comes over shortly after I get home, and of course Cassie is ecstatic to see her. I pour myself a glass of wine and offer Maddie a soda. She declines, but asks for a glass of water instead. We both sit down in my living room while Cassie jumps around and plays on Maddie's lap.

Me (figuring it's time to dive right in): "So you had a basketball game tonight, right?"

Maddie (seemingly surprised at my question): "Yeah, how'd you know??"

Me: "I actually was there! Like at the game... and I saw you scored a basket, too. Nice work!"

Maddie: "Oh wow. Thanks! I had no idea you were in the stands!"

Maddie (with a little bit of a perplexed look): "So why were you there? I thought your son went to a different school, right? Do you go to a lot of our games?"

Me (trying to be as nonchalant about this as I can): "Ha, yeah. So I realized something tonight when I saw you on the team. It's kind of embarrassing though?"

Maddie (smiling): "What is it? Now I'm intrigued!"

Me (after taking a sip of wine before dragging it out for dramatic effect): "Soooooo..."

Me (pretending to wince): "I'm actually dating your coach?"

Maddie's face instantly lights up as if she's just heard the most exciting news of her life.

Maddie (with eyes so wide): "Oh my god! Your boyfriend is Coach Dream!"

Huh?

Me (with genuine confusion): "What?!?"

Maddie (processing it all): "Oh my god, you didn't even say boyfriend. Is it Claire? Are you and Coach Claire dating?"

Okay, now I'm really confused. I know Greg's assistant Claire is gay, but I thought it had been pretty obvious that I'm not.

Me (laughing and confused): "No, no, no. I'm dating Greg, your head coach."

Maddie (back to being 100% excited): "Yeah! That's Coach Dream! That's what we call him at least."

Okay, that finally makes sense. But wait... what?!?

Me: "You guys seriously call him 'Coach Dream'?? Does he know this?"

Maddie: "Actually, he may not even know. But yeah, all the girls on the team call him that, at least when he's not around."

Oh my god. This is too great.

Me (just clarifying): "And I assume this is a flattering nickname, right?"

Maddie: "Yeah, definitely. It's because he's such a hottie."

Maddie (continuing): "And because he's an awesome teacher and coach, too."

Maddie (rambling now): "Oh my god, I can't believe you guys are dating! That's so awesome... for both of you! Oh my god, I shouldn't have said he was a hottie, that was so inappropriate of me."

This is amazing. In every way.

Me (laughing): "Oh Maddie, don't apologize one bit. Hearing that the whole team calls him Coach Dream just totally made my day. That is both hilarious and fantastic!"

Maddie (laughing as well): "Oh good. I just think he's so great. That's all."

I had been pretty confident from watching Maddie around Greg as to how she felt about him, but that comment really solidifies it. I guess it's still possible her feelings are more idolization than sexual attraction, but it's pretty obvious now she thinks very, very highly of my boyfriend.

Me: "Well, you're preaching to the choir on that one."

Maddie (chuckles but then gets a serious look on her face): "So he was married, but then his wife died, right?"

Me: "Yeah, it just breaks my heart thinking about it. It was a drunk driver. Some asshole. Greg doesn't talk about it much, to say the least."

Maddie: "Ugh. That just makes me queasy thinking about it. Poor guy."

Maddie (perking up): "But I'm so glad you guys are together now. I'm happy he's not alone anymore, and I'm happy you ended up with like the most perfect boyfriend ever!"

Wow. Okay, there's absolutely no more doubt in my mind. It's crystal clear how she feels about Greg, but it's also kind of humorous how she phrased that, too. I'm sure Maddie didn't intend to, but she basically just compared me to being a warm body, while calling Greg the 'most perfect boyfriend ever'. Too funny!

I obviously don't take offense to it though, as I can still remember what it was like to have a crush at that age. You really do feel like the object of your affection can do no wrong, and while I never lusted after someone significantly older than I was, I can only imagine the age difference between Greg and Maddie makes him even more infallible in her eyes.

Suffice to say, Maddie's comment about Greg being the perfect boyfriend makes me smile. It also gives me an opening. Up until this point, I haven't really asked Madison any direct questions about boyfriends or dating or anything like that, but I've been dying to, so this seems like a pretty good opportunity to break the ice.

Me: "Yep, I'm very lucky. So... do you have a boyfriend or anything?"

Maddie (answering like it's just any other question): "No, not really."

Hmmmm. 'Not really' is an interesting answer. I don't say anything, but I'm sure I have a little bit of a questioning look on my face.

Maddie (feeling the need to clarify): "There's this one boy, but I don't even really like him."

Me: "Oh?"

Maddie (very dismissively): "Yeah, it's a long story. Well, it's not even a long story about that boy. There's just another long story about a different boy."

Me (after putting my wine glass back down on the table): "Well, I've got nowhere to be, so I'd actually be curious to hear it."

Maddie: "Seriously?"

Ha, if you only knew the half of it, Maddie. But hell yeah I want to hear about it!

Me: "Yeah, seriously. So who's this other boy?"

Maddie (after taking a sip of her water): "Okay... well... There was this other boy. His name is Lucas."

Oh shit. I wonder if there's any chance this is the same Lucas who's the boyfriend of that Amanda girl on their team?!? She's their star player... and unbelievably beautiful, and popular, and she and Lucas are going to be prom king and queen supposedly. All of this is according to Greg, at least.

Me (trying my best not to make any sort of visible reaction): "Okay..."

Maddie: "Yeah, and so he and I dated, but not for very long."

Hmmm... maybe it's not the same Lucas then? I mean, could sweet, innocent Maddie really have dated one of the biggest studs in school? Granted, she is a cutie, and I still haven't seen what this boy looks like, but supposedly he's a star football player and all, and I would have to imagine that Greg of all people would've known if Maddie dated him, right?

Maddie (continuing): "But then we broke up. And now he's dating this girl on our team, Amanda."

Oh fuck! It is the same boy! That's incredible. I can't believe I know this huge piece of gossip about Maddie that Greg doesn't even know. This is so exciting!

Oh man, you know what else this means? I'm guessing Maddie's not a virgin like Greg and I had surmised. I mean, if she's dating the most popular boy in school, then that sure seems like she's probably not that innocent, right?

Me (getting back to the story that Maddie is actually telling): "Oh, I'm sorry. That must be tough... seeing your teammate with him and everything?"

Maddie: "It's not great. But honestly, it's not that bad. Amanda... she's actually really nice and hasn't been petty about the whole Lucas thing at all. And I don't know how much of the game you saw tonight, but she's really good. She's like by far our best player."

Me (feigning doubt yet again): "Oh yeah, I think I remember her? She's tall with a brown pony tail, right?"

Maddie: "Yeah, that's her. Like I said, she's so nice about it. And Lucas was even so nice when we broke up. It's hard to explain."

Me: "Wait, so why did you and Lucas break up?"

Maddie (seeming a little sad reminiscing): "Well, he broke up with me. But he was so nice about it. He came over to tell me in person, and he basically just said he liked me but he wanted to try dating some other people before graduation, and he was so apologetic about it. I'm sure it makes me sound pathetic that I just accepted that as a valid reason, but I didn't know what else to do."

Me: "No, no, no... that doesn't make you sound pathetic. I totally get how that could be so sad to hear but wouldn't make you hate him or anything like that."

Maddie: "I can't believe I'm telling you this, but I'm sure it had to do with sex. Or specifically, the lack there of."

Oh Madison, I'm so glad you're telling me all of this! This is incredible. Yeah it's a little surprising you're being so open with me, but it's like a treasure trove of information I'm getting here.

And based on this latest comment, it sounds like Maddie is a virgin after all??

Me: "So he wanted to have sex, but you didn't?"

Maddie: "Yeah, basically. And it was so dumb. I don't even know why I didn't."

Me (with the moment of truth): "So you're a virgin?"

Maddie: "Yeah, well... I was at the time."

Wow. Interesting. So she was a virgin then, but she isn't one now?!?

Me: "Okay..."

Maddie: "Yeah, that's where the other boy comes in. After Lucas and I broke up, I hooked up with this friend of a friend. His name is William. He doesn't even go to our school. But we had sex. Twice. And did some other stuff. But he's kind of annoying and I don't even really enjoy hanging out with him."

Interesting. But poor girl, it sounds like she still has it bad for Lucas, and she's just biding her time with this other kid?

Me: "I'm so sorry things didn't work out with you and Lucas. But how was it when you did stuff with this other boy, William? Was he at least nice about the physical aspect of things?"

Maddie: "He was fine. He didn't pressure me or anything. In fact, I think I kinda used him if anything. After Lucas, I just really didn't wanna be a virgin anymore."

Me: "Yeah. I could see how you could feel that way. I'm glad it all happened on your terms, though."

Maddie: "Yeah, it did."

I take another sip of my wine.

Maddie (looking up at me with the sweetest expression right now): "I'm so sorry I'm spilling my guts to you. I can't believe I'm telling you all of this."

Me: "No, no, it's totally fine. I'm glad you're telling me. I'm even happy to help, not that I'm an expert on relationships or anything, let alone teenage ones. Ha."

Maddie (with a concerned look on her face all of the sudden): "Oh my god, you can't tell coach about any of this! I would die."

Me: "Oh of course not. I totally understand. I would never tell him. We'll keep this just between us girls."

Who am I kidding? I'm obviously going to tell Greg everything. I mean, how could I not?!? And I fully realize how shitty this makes me, so you don't need to tell me, too. Trust me, I'm probably going to hell for this.

Me: "So it sounds like you still have feelings for this Lucas boy?"

Maddie (with a look that's somehow half excited and half depressed): "He's so nice. Like I said, even the way he broke up with me was compassionate. And he's like this superstar athlete, and so people always assume that's all he is. But there's so much more to him."

Me: "Wow. He does sound like a pretty awesome guy. But so, was he pressuring you to have sex, though?"

Maddie (with a friendly, but correcting tone): "No. Definitely not. He's too nice to do something like that. But I could tell he wanted to. And he would sometimes ask, or he would offer to do things, but he wasn't pushy about it at all."

Me (genuinely curious): "What do you mean, 'offer to do things'?"

Maddie (smirking): "Like sometimes the topic of oral sex would come up, and he would tell me that if I ever wanted to, he would do that to me, even without..."

Maddie (with her hands out gesturing): "Like, you know..."

Me (laughing): "Without you having to return the favor?"

Maddie: "Yeah exactly. He said I didn't have to do that if I didn't want to, but he was still offering to go down on me."

Me: "So have you never done any sort of oral sex? Like did you and that other guy do that?"

Maddie: "So I gave that Will guy a you know... blow job, hoping kind of that he would then... you know... reciprocate? But he didn't."

Me: "That's so lame... of him, that is."

Maddie: "And you know, honestly now that I've had sex, I'm actually most curious about what oral sex would feel like."

Wow. Yet again, I'm just astounded that she's sharing all of this with me!

Me: "So you're saying you really wish you could find a guy to go down on you?"

Maddie (kinda of blushing): "Well not just any guy, but yeah..."

Holy fuck. I wish so badly I could just tell her how much Greg would absolutely love to do that to her, but I obviously can't. But my god, Greg is going to blow his load when I tell him all of this.

Me (laughing): "Yeah, I can see that."

Me: "Well... speaking from experience, it can definitely feel pretty good. But like you said, only if you find the right guy. Ha."

Maddie (laughing): "Now you're making me jealous."

Me (wondering if that was a specific comment about Greg): "Oh, am I?"

Maddie (continuing): "God. I'm such an idiot. I think back to how Lucas was practically begging to do that to me, and I wouldn't let him. Fuck. How much of a moron am I??"

Holy shit, I think that's the first time I've ever heard Maddie curse. And how funny is it that the one thing to get her riled up enough to swear, is how badly she needs her pussy licked!

Me (trying to be reassuring here, but secretly I keep getting more and more turned on as we talk): "Oh no. Don't blame yourself. You weren't ready then. It seems like you might be ready now, but you weren't back then. And that's totally fine!"

Maddie (sadly): "I guess..."

Maddie (after perking up slightly): "Well, I probably should go. I've taken up enough of your time already, and I've bombarded you with waaaaaaaay too much information, ha."

Maddie (after reaching down to scratch Cassie all over): "I'm gonna miss this girl though. I'm gonna miss you, Sweetie."

Maddie (looking back at me): "But thanks so much for listening to all my drama. Seriously."

Me: "Oh of course. And Maddie, don't let anyone ever try to convince you that being open about sharing things is a bad thing. I actually think it's a superpower, and it's really refreshing to see how comfortable you are with yourself."

Maddie (looking right at me while smiling): "Thanks. That's really nice to hear."

Me: "I'm just sorry I don't have any better advice to give you at the moment. It's obviously cliche, but it's true that there are so many fish in the sea, so don't beat yourself up over it not working out with Lucas. Despite how great he is, I'm sure there are even more amazing guys out there for you."

Maddie (chuckles): "Ha. That's easy for you to say. You actually found one of them."

Oh my god, Maddie. Just hearing you say that makes my heart skip a beat.

Looking at you, sitting here on my couch, you really are something else. You're so kind, sweet, and thoughtful. You're an absolute cutie, too. And while you're still so innocent, you're also quite mature and obviously curious about your budding sexuality, and I absolutely love how open and comfortable you are with it.

I was so shy when I was a teenager. I was never able to even talk about sex when I was in high school, let alone do anything with the boys. You're so much more self-assured than I was, that I'm legitimately jealous. It makes me want to live vicariously through you.

And it doesn't hurt that I find the idea of teenage love, sex, and relationship drama to be so fucking hot. The hormones, the curiosity, the young, flawless 18-year-old bodies. God, if only I had a time machine that would allow me to redo those years of my life. I would be so different, and so much more adventurous, than I was the first time around. But if I can't do that, then at least I can try and help you, Madison, to get the most out of these glorious years.

And holy shit, you want someone to go down on you, Maddie? And you clearly have a crush on my boyfriend, Greg? Well, do I have some news for you! He will eat your fucking pussy for hours on end. He will devour it. He will worship it. He will make you cum, over and over and over again, and I will love watching every single time it happens. Fuck, he'll probably jizz in his own pants just from licking you. That's how much he'd enjoy doing it.

I don't know exactly how this is going to play out, or how I'm going to make it happen, but I am. I've never wanted a specific sexual act to occur as badly as I want this one, and it doesn't even directly involve me!

Me (after composing myself): "Yeah, Greg is definitely a catch. Okay let me walk you out to your car..."

Fuck. I really need to call Coach Dream. He is not going to believe this.