Coach's Cutie Ch. 02

Coach's Cutie - Chapter 2: The Victory Hug

Greg and I had our big conversation about Madison last Saturday night, and here we are on the following Thursday evening, and somehow I haven't mentioned her name to him even once since then! But trust me, you have no idea how hard it's been to restrain myself. We're talking five full days, of which this whole time I've been absolutely dying to talk to Greg about his secret crush, and yet I haven't said a single word.

You see, I know my boyfriend, and I could tell last weekend that as soon as Greg confessed he was attracted to one of the players on his basketball team, he instantly started worrying that he shouldn't have told me. But in reality, I'm so glad that he did!

And I get it. Even though she is officially 18, she's still in high school, and he's both one of her teachers and her coach! Even just admitting a small level of attraction to her is conceivably putting his job at risk, so I definitely understand his trepidation. But of all people, he can definitely trust me. I fully understand how critical it is to keep this a secret, and I would never, ever do anything to jeopardize the career he loves so much.

But on the other hand, it's so freaking hot that this adorable, little, curly-haired, try-hard (as he describes her) turns him on. But part of that is you have to understand Greg. He's literally one of the nicest, most sincere human beings I've ever met. And I think it's this combination of seeing someone who's so genuinely good, have these salacious, hidden desires that I find so appealing. Or maybe even reassuring?

And all things considered, his desires aren't even that extreme. Granted, I've never actually seen what Maddie looks like, but it's certainly not unusual, unexpected, or unnatural in any way for a 37-year-old man to find an 18-year-old girl sexually attractive. It's obviously taboo in our society though, and doubly so when you throw in the whole teacher-student aspect.

But because it's Greg, and how much of a model citizen I know for a fact he is, it's almost comforting to see that people like him can have these feelings and desires too. It's like it actually makes me feel better about my own impure thoughts?

I feel like I'm pretty accepting of myself, and I'm definitely not a judgy person, but even I'm not immune to feelings of guilt sometimes, even if it's for simply thinking about something, and not even doing anything.

I have a son in college now, and I can't tell you how many times over the past few years I've caught myself concocting ridiculous sexual scenarios involving one or more of his friends. It's like as soon as I meet a new acquaintance of his, my first instinct is to immediately start fantasizing about this poor kid in some way. Seriously, I'm so weird!

And while I do know that these thoughts are most likely completely harmless, I can't help but feel a little guilty. It's obviously nonsensical, but I'd be mortified if my son were to ever just accidentally read my mind somehow. But there's another part of me that's like, is there something wrong with me? Like why can't I fantasize about men my own age like a normal person?

But when I hear my boyfriend confess similar thoughts and feelings, it goes a long way in helping me to actually feel normal. Like, maybe there isn't something wrong with me after all? And I'm sure that's a big part of why I find it so appealing to explore this specific fantasy of Greg's.

So here we are, the two of us together at Greg's condo and already in bed for the evening. Tomorrow night is his team's first basketball game of the season, and so I think it's finally time to revisit this Madison subject. I mean, he didn't honestly think I was never going to mention her again, did he?

Me (leaning in to give Greg a kiss while we lie next to each other under the covers): "I'm excited for tomorrow."

Greg (clearly not sure what I'm referencing): "Tomorrow?"

Me: "Yeah silly, your basketball game. I'm excited to watch you coach!"

Greg (putting two and two together): "Ahhhh... of course. I'm sure you're also excited to pay attention to one particular player on my team as well."

Me (with exaggerated faux confusion): "Someone on your team??? Well whoever could you mean??"

Me (after having a good laugh): "But seriously, all kidding aside, I really am genuinely excited to watch you coach during a game. But I'm also super intrigued to get a peek at this Maddie girl, too."

Greg (sounding legitimately somber): "I shouldn't have told you that. Or really... I shouldn't have had those thoughts in the first place, is more accurate."

Okay, I really need to fix this. Greg is not at fault here, and I need to somehow convince him of that!

Me (quickly): "No, no, no! Hon... you did absolutely nothing wrong by having those thoughts. And I'm so, so, glad you told me. I absolutely love that you trust me enough to confide in me something like that."

Greg (quietly): "I don't know..."

Okay, I feel like I'm already making progress here. This is doable.

Me (giving Greg a longer kiss on the lips): "You're literally one of the nicest people I know. Don't ever feel bad about being attracted to someone. It's human nature to feel that way. In fact, you telling me about Maddie has actually made me more attracted to you than ever."

Greg (skeptically): "Seriously?"

Me: "Yeah, I'm not joking. I love it."

Okay, my plan tonight was to bring Maddie up in the conversation and to see how Greg reacted. Obviously, he's still feeling somewhat guilty about the whole thing, but it's not the end of the world. I think the key here is I just need to try and normalize his feelings as much as possible. But it also probably wouldn't hurt if I helped associate any conversation around Maddie with some positive physical feelings? If you know what I mean... :P

I not so subtly begin to slide off both my sleeping shorts and my underwear underneath them. Greg notices and gives me a look that says both 'what are you doing?' but also 'please don't stop'.

Once I'm bottomless, I slowly start to free some space under the covers so I have enough room to climb on top of Greg. He's still wearing his standard boxer briefs, but that doesn't matter right now, as I have a different plan in mind.

One thing I've learned about Greg in the couple of months we've been dating, is that there's nothing he loves more than oral sex. And I'm not even talking about blow jobs, I'm talking about him giving me oral sex.

Now don't get me wrong, I've encountered a guy or two since my divorce that genuinely seemed to enjoy going down on me, as well as a few that had zero interest whatsoever (those guys didn't stick around for long!). And I think I do a decent job of keeping myself nicely groomed (i.e. shaved) down there. But the level to which Greg enjoys licking me, is something of which I've just never experienced before. He's downright addicted to it.

And while this is obviously a nice-to-have feature in a boyfriend on an everyday basis, right now it's especially convenient. You see, at the risk of sounding manipulative, I really need to make sure that Greg is fully in the mood, if you know what I mean. So I figure I have no choice but to use this weakness against him.

With room now under our covers, I gracefully swing my leg over his bare chest and lift my naked lower body overtop of him. From there, I start inching my way further up his body, bringing my vagina closer and closer to his face. I can see his eyes alternating their focus between making eye contact with me, and darting back down to stare at my slowly approaching pussy. Each inch forward brings me ever closer, and then I see Greg both close his eyes and take a deep inhale through his nose.

My plan is working like a charm. Perhaps the only thing Greg loves as much as licking my vagina, is smelling it. God bless this man.

I decide to rid myself of the only thing I'm still wearing, so I cross my hands and slowly start lifting my sleeping t-shirt up and over my head, so now I'm completely naked. I continue to straddle Greg, and my vagina is hovering only an inch or two above his nose and mouth. It's so close to him, I can actually feel his breath on my lips as he exhales.

Greg (finally breaking the silence with a meek question with an obvious answer): "Becca, what're you doing?"

Me (still with my pussy right above him): "What does it look like I'm doing?"

Greg (turning his head to the side so he's no longer looking right at my crotch): "I don't know? That's why I asked."

Huh? What's with him? I'm actually shocked Greg hasn't taken the bait here and just started eating me out. Instead, he has his head turned away like a dog with a treat that it's not supposed to go for, so it has to pathetically look away in order to control itself.

The only thing I can think of is he's figured out I'm trying to associate sex with Maddie, and he's purposefully holding that against me. But if he wants a battle of wills, I say bring it on.

Me (lowering myself even closer so now my lips are grazing against his nose): "Do I smell okay down there? Or is there something off about my pussy?"

He knows I'm genuinely self-conscious about that sometimes, so I don't think there's any way he would lie and say there was.

Greg (starting to breathe a little heavier): "No... you smell so... you smell amazing like always."

Me (reaching down to pull the skin where my thighs meet my pelvis apart to open up my vagina as much as possible): "Do I look okay too?"

Greg (panting now): "Yeah, you look so good..."

Me (smiling): "Okay, good."

And then with a sudden jerk, Greg finally capitulates and gives in. His two hands grab onto my naked hips and sit me down, right onto his face. His nose immediately presses into my clit while I feel his warm, wet tongue thrust up and into my pussy. Fuck yeah.

Greg wastes no time whatsoever, as I immediately feel his mouth and tongue start feverishly moving in and out, back, forth, and around every slick fold and crevice of my vagina. But while his lips, mouth, and tongue are completely hidden underneath my crotch, I'm able to see his eyes poking out just a little bit. And once we make eye contact, I see the sides of his face wrinkle up, letting me know there's a giant smile behind my mound as he continues to orally please me.

But as great as this feels and as satisfied as I am knowing that Greg is enjoying himself, I want to make sure I stick to my plan. So I gently, but abruptly, start lifting myself up, and despite some minor resistance from his hands holding me in place, I begin to spin around.

Greg's not deprived of my pussy for long though, as once I've completely the 180 degree turn I had in mind, I begin to lower myself back down onto his face. But this time, instead of facing the headboard, I'm oriented towards the bottom of the bed, as well as Greg's lower body.

Greg immediately takes ahold of me in this inverted position and pulls my hips down even harder, forcing my crotch onto his face. And now I'm sitting on his head, with pretty much my entire weight pressing down on him.

Normally when we're in this position, I'm so self-conscious that I might be smothering him, that I struggle to relax. Like I literally worry that he won't be able to breathe from underneath my vagina and he'll end up passing out.

But right now, with as much as I want Greg to really, truly get as much enjoyment and satisfaction out of this as he possibly can, I say fuck it. Not only do I not resist Greg's pulling my pussy and ass down onto his nose and mouth like I normally would, but I even start adding some of my own force and pressure by really grinding my crotch into his face.

I can tell this catches Greg by surprise, as he lets out an enormous moan that vibrates the lips of my vagina from deep, down below. Mmmmmmmm.

As I continue to sit on my boyfriend's face with more force and weight than I ever have before, I look down and see Greg's pitching a huge tent in his black boxer briefs. I start rubbing my crotch forwards and backwards, enjoying all the sloppy wet stimulation that comes with every movement. I even feel his nose press directly into my butthole with each jerk, and to be honest even that feels quite pleasurable.

I want more though, so I lean forward and take ahold of his stretched out undies and start to push them down and off his crotch. Once I do this, his fully erect penis comes springing out from behind the one garment that had been holding it back. Greg then begins to slowly lift his legs and knees up, signaling to me that he wants his boxers completely removed. I happily oblige, sliding his underwear off his legs before tossing them aside and onto the floor.

As his legs crash back down onto the mattress, his adorable cock bounces a little forwards and backwards, almost like a spring. It's so erect, so engorged with blood, and so unbelievably tempting. God, I need to put it in my mouth!

I lean forward to get my lips near his plump mushroom tip, and as I do I feel Greg's head come along with my pussy, as if he's determined to not let his face get separated from my crotch, even for a second. I have no problem moving enough to get into range though, and I immediately use my tongue to make contact with the head of his penis. I give him a few, small seductive licks before quickly transitioning to taking his entire length in. I feel his cock jam into the back of my throat as my lips touch down on the skin and pubic hairs surrounding the base of his penis.

Greg (finally pulling back ever so slightly to separate his mouth from my vagina): "Ohhhhh... fuck...."

I bob up and down a few times, trying to both keep firm pressure on his shaft while also offering up a nice, soft glide while I do so. My mouth starts to make some audible slurping sounds, and almost as if we're in some sort of competition, I hear Greg start making exaggerated wet moans and slurps on the other end of this glorious 69 we're currently engaged in.

But as amazing as this mutual oral sex is, I know it's still not the end goal I had in mind (I know, I'm never satisfied!). This whole sexual encounter was predicated on my desire to talk to Greg about Maddie, and considering that both our mouths are currently filled with each others genitals, we're obviously not in a good place to have a conversation right now, ha.

So even though we just started sixty-nining a minute ago, I again decide it's time to switch things up, but this time we're moving on to the main course. I simultaneously remove my mouth off of Greg's penis while also swinging my leg to the side in order to dismount his head. In doing so, I can see a brief moment of discontent in Greg's face, but as soon as I reorient myself and make it clear that I'm about to start riding him, any sign of disappointment in his expression is already long gone.

With both my pussy and his cock nice and slippery from our simultaneous oral sex sessions, I climb over him and slide his rock hard boner inside me with the utmost of ease. And as I sit down and rest the full weight of my body onto his pelvis, we both break out into huge grins.

And oh my god, Greg's cock feels so fucking good all the way up inside of me. I absolutely love this initial moment of entry. In fact, it might be my single most favorite part of having sex, and it's most satisfying of all when every part involved is nice and lubricated, like it is right now.

We're both still completely naked, and as I lean down and take ahold of Greg's hands and press them against his pillows, I see his gaze momentarily redirect to check out my extremely modest boobs that are now dangling in front of his face. And with his attention currently on my tits, I figure this is as good a time as any to try and kick off this whole conversation about Madison.

Me (joining Greg in looking down at my chest): "Does Maddie have bigger or smaller breasts than I do?"

Greg (a little caught off guard by the question): "Oh, uh... I don't know... about the same maybe?"

Awesome. He actually answered the question. That's a good sign.

I completely interlock my fingers with his and press his hands even more firmly into the mattress. I start slowly rocking up and down on his cock, doing my best to make sure we get a good rhythm going without him having to move a muscle.

Me: "So what number is she?"

Greg (confused): "Number?"

Me: (clarifying the question while starting to bob up and down with a little more speed): "Yeah, what jersey number does Madison wear in the game?"

Greg: "Oh, uh... 12. She's 12."

I can tell the motion is really starting to affect Greg, so I probably need to be careful as I don't want him to cum too early! We still have more to discuss. :P

Me: "So you said she'll get to play some tomorrow?"

Greg (struggling a little to answer): "Yeah... she'll play."

Me (grinding and smiling): "Nice. Do you think she'll play enough to break a sweat?"

Greg: "Yeah, probably. She plays... she plays so... so hard."

Me: "Mmmmm... nice. So I have a would-you-rather question for you."

Greg (with a very intense look on his face as I continue to slowly grind his cock around inside of me): "Okay..."

Me: "Would you rather eat Maddie's pussy... immediately after a game when she's all hot, flushed, and super sweaty?"

Greg moans softly.

Me (finishing the proposition): "Or would you rather eat her out after she's all showered and freshly clean, smelling like some super girly shampoo?"

Greg (closing his eyes while tilting his head up): "Ohhhhh..."

Wow. I don't think he's cumming quite yet, but he sure seems to have liked that question.

Greg (quickly opening his eyes up to look at me): "Sweaty. Right after the game."

Me (loving every single thing about that answer): "Ohhhh... that's so hot."

Greg is staring at me so intensely right now, and I can tell he's really worked up by our topic of conversation. This is exactly what I was hoping for! And while I'm not quite on the edge of orgasming myself or anything, I feel like it's worth pretending I am.

Me (after increasing the intensity of my grinding): "Oh Hon... All this talk about Maddie is gonna make me cum. I'm gonna cum so hard..."

Greg (after grabbing ahold of my hips and for the first time starting to fuck me as much as I'm fucking him): "Oh babe... I want you to cum, Becca. I'm gonna cum so fucking hard too."

Okay, I guess I'm going to fake an orgasm here? I hadn't really planned on doing this, but this is happening.

Me (after a little embellished squeal): "Oh please make me cum. Tell me what you want to do to Madison's pussy."

Greg (desperately): "Oh I wanna eat her little pussy so bad... I wanna lick her so much.... I wanna make her feel so good... and then I'll need to fuck her. I'll need to cum inside her. Oh god... oh fuck..."

Oh my god, that's so hot.

Me (faintly): "Oh Greg, I'm cumming..."

I'm not actually orgasming (please don't judge!), but I am thoroughly enjoying this.

Greg (clearly not faking it like I am): "Ohhhhh... I'm fuuuuuuckking cumming... Ohhhhhhh..."

As Greg orgasms, he starts thrusting his hips up so hard that I'm actually bouncing up and down on his pelvis. In fact, I'm a little scared I'm going to come entirely off of his penis and end up breaking his cock when I land back down, but once I realize that's not happening, it starts to hit me just how good this feels. Holy shit, this feels soooooo fucking amazing.

His powerful thrusting lifting me up, his cock hitting me from the inside, the fact that Greg just admitted that he not only wants to eat Madison out, but that he wants to fuck her pussy and cum inside her. Holy fuck, everything about this is so fucking hot.

I absolutely love the idea of a man cumming inside of a vagina. I always have, and I always will. I don't fully know why, but it's something about the uncontrollable passion and lust involved. Like the fact that it's a bad decision, but people do it anyway, is what inherently makes it so hot. It creates a sloppy mess, it brings the obvious risk of pregnancy to the table, not to mention STDs, and yet people still do it, even in cases where they specifically discuss not doing it ahead of time. I just fucking love it.