Coach's Cutie Ch. 01

As you all can probably tell, I'm back for my third attempt at a story. I know I've already said this a number of times, but I can't thank all of you enough for the tremendous about of encouragement and gratitude you've so generously given me. Not only does it make me feel reassured, but it's honestly quite exhilarating.

Personally, I've always loved the feeling of sexual gratification. From the buildup and anticipation, to the pleasure and excitement of the moment, all the way through to the release and satisfaction after it's over. Everything about all the different sensations is just wonderful. And so now that I've discovered I'm able to use my words on here to help spread sexual enjoyment to people that I've never even met, I think I can safely say that I'm officially addicted. It's such a thrill!

Now granted, I know my stories aren't for everybody, and that's a-okay with me. As they say, to each their own. But for those of you that do find at least a little connection with what I write, I just want you to know that the more you enjoy my stories, or even (fingers crossed) get aroused by them, the more you're turning me on as well! I simply love reading your responses.

So once again... Thank you!

Now here we are with my third literary adventure, and with this story, I'm again going to try something new. For those of you who may not have read my previous two submissions to this great website, my first story, Dormant Desires, was actually based on real life events. It was the retelling of the single craziest night of my life. My second story, Runaway Fantasy, was the opposite, as it was a complete and total fabrication. While it was probably a decent reflection of me and my own warped imagination, none of the characters or events in it were based on anything real.

And so for my third story, Coach's Cutie, I've decided to take an approach that kind of mixes these first two attempts together, into a hybrid fiction and non-fiction tale. A number of the characters and occurrences that I'll be describing are 100% real, including myself, Becca. In fact, most of the character setup and early events of the story are completely true. But from there, I will be adding in some fictional twists and occurrences, primarily for dramatic and entertainment purposes, of course. But if I'm being optimistic, perhaps it's not so much that these events haven't happened in real life, it's just that they haven't happened... yet. :P

Okay, with that out of the way... let's get started!

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Coach's Cutie - Chapter 1: The Jury's Still Out

I've been officially divorced for almost a year, and separated for over two. I won't rehash all the details of my failed marriage right now, but let's just say that sexually speaking, I've definitely been making up for lost time over these last 24 months.

It's been fun, but it's been confusing at times, too. It's been eye-opening to see firsthand how much dating has changed over the last twenty years. Although to be fair, I barely dated much in the first place prior to getting married, so I don't even know what I'm comparing it to. All I know is that dating right now, from the perspective of a woman in her very, very, early 40s, can be a little intimidating.

But it can also be quite rewarding. And one thing I've discovered is that the biggest key to achieving an enjoyable outcome when attempting to date, is simply knowing what you want. I know that sounds obvious, but it's often harder than it seems to pin down.

You may start out desiring one type of person, or one particular trait, but once you find this thing, you might not be as enthralled as you imagined you would be. Our tastes evolve, our fantasies change, and you never know when you might develop a crushing case of the ick (a new word I've recently learned).

So where does that leave me? Well I actually do have a decent idea about who or what I want, or at least I think I do. I want an extremely nice, but devilishly perverted man. I get that that's a little bit a of paradox, as those traits may seem contradictory at first, but I'm holding out hope that a guy like that does exist.

In fact, this is what I'm envisioning...

I want a man, who when he's driving through a parking lot and sees an older lady starting to load her bags of groceries into her trunk, will throw his blinkers on and immediately hop out of his car. He'll then carefully load all of this woman's groceries for her before returning her cart to the corral. Then he'll politely let the woman know to have a great day, before hopping back into his own car to drive away without the slightest need for any recognition.

Okay, so that's the nice guy part.

But when this same guy gets home, despite it being only 4:30 in the afternoon, I want him to unexpectedly take my hand and lead me into my bedroom. From there, without saying a word, he'll begin to tie my hands to my bedposts and strip me completely naked.

Then for the next two hours, I want my dream man to take total control over me and my body. He'll use a combination of every part of his own body, and every toy in my special hidden shoebox, to repeatedly bring me to the edge of orgasm. But no matter how good it feels, and no matter how much I beg and plead over these 120 minutes, he won't actually let me pass over that magical threshold and climax.

I'll want him to lick me, I'll want him to penetrate me, and I'll want him to vibrate me over and over. And every time he builds me up to cum, I want him to sense my approaching euphoria, and no matter how hard I try to deceive him and hide my impending release, he'll see through my deception and bring whatever stimulation he's using on me to a screeching halt. And then after a brief pause, he'll completely switch up whatever he's doing, forcing me to start all over and rebuild my orgasm from square one.

And then only after I've suffered a total and complete loss of time and situational awareness, and I've given up all hope of ever actually cumming, will he finally build me up one last time. But on this crescendo, instead of mercilessly ripping out my pleasure just when I need it the most, he'll do the exact opposite. He'll lean in to whatever he's doing to excite me, and he'll double down on the intensity of the stimulation, bringing me to and through a mind blowing orgasm that leaves me completely and totally paralyzed from equal parts, pleasure and exhaustion.

That's what I want. Those two things. Actually... make it three things. After I cum so hard I basically pass out, I'll want him to order a delicious spread of sushi delivered to our door, so both of us can feast on it in bed while we watch a show and start to recover from our mind-blowing sexual escapade.

So all of that shouldn't be too hard to find in a man, right? :P

Well, as luck would have it, I actually am dating someone at the moment who could possibly be the one. And when I say 'the one', I'm not talking about him being my soulmate or even future second husband. I'm just talking about finding this perverted nice guy I've convinced myself is my ideal dating partner, at least at this stage of my life.

So the guy in question is named Greg, and we've been dating for a couple of months now. And at this point, I think I can safely say he clearly passes the nice guy portion of the test. While we haven't actually run across any grocery shopping grandmas just yet, I've witnessed plenty of instances already that give off a very similar Good Samaritan vibe.

There was one time a couple of weeks ago when we came across someone's driver's license just laying out in the open on the sidewalk. We both saw it, as it was impossible to miss, and of course Greg rushed over to pick it up. From there, he started looking around trying to find whomever had dropped it. It had a picture of a middle-aged woman on it, and so the first thing Greg did was hustle around to check anyone walking nearby to see if it might be theirs.

When he didn't have any luck finding its owner on the spot, he didn't turn to ask what we should do next, he simply told me we'd need to find a post office. And sure enough, we googled the closest post office, walked almost a mile to get there, bought a stamp, politely got a free envelope, and then he sent this woman's ID on its way in the mail to the address listed on the license. After that was done, we went on to enjoy the wonderful lunch we were walking to in the first place, albeit a little later than we had initially planned.

So that's just one example of how nice a guy Greg is, but you get the idea. However, that's still only half the equation though, as it's important for this man to check the box on the sexual side of things as well. And while so far things in bed with Greg have started off well, I think it's fair to say the jury's still out on whether or not he has the required amount of pervertedness hidden behind that nice guy exterior that I'm so desperately hoping to find.

One thing I am sure of though, is that Greg is different from the other guys I've dated up until this point. So far, there have been two distinct categories of men I've encountered: divorced guys, and guys who have never been married. I'm sure hypothetically I could explore the third option, currently-married guys, but I honestly have zero desire to ever get involved in something like that.

With these first two groups though, I've definitely seen some patterns with the men based on whether they're divorced or simply single. Basically, the single guys usually come across as more immature, while the divorced guys seem to be a little more jaded or cynical. Don't get me wrong though, plenty of these guys have good traits as well, but either way, I haven't really developed a clear preference for one group over the other.

With Greg though, it's all irrelevant as he actually comes from a fourth, albeit it much less common group, widowers. At first, a widower seems kind of like an ideal person to date. They were tolerable enough for someone to marry them, and while no one ever wanted to divorce them, they're still fully available to start a relationship with.

Now, there is one extremely critical catch to dating a widower though, and I say this mostly joking, but with a small sliver of seriousness. And that is, you have to be 100% sure that there's no way in hell the guy you're about to date is at all responsible for his wife being dead. I mean, it does happen, right? So you do kind of need to evaluate the circumstances around his wife's passing.

A man whose wife died of breast cancer? It's tragic and devastating, but clearly nothing to worry about. A man whose wife died due to an accidental drowning on a lake while the two of them were alone on a supposedly romantic boat ride? No fucking way am I sticking around to see what it's like to date that fella. Hard pass.

Okay, all joking aside, thankfully Greg is firmly in the first group. He actually briefly brought up his wife Jane on our very first date, and how she had passed. It clearly is a subject he doesn't like talking about though, which is obviously understandable. But he mentioned upfront that she had died in an automobile accident due to a drunk driver.

Of course after I found that out, being the degenerate that I am, I did some googling when I got home after our date and found out the full story. Jane was apparently hit head on in the middle of the afternoon by a male drunk driver who had crossed over the median. Both cars were single occupants, and both Jane and the drunk driver were killed instantly it seemed. The whole thing is just so heartbreaking and tragic.

Greg is a few years younger than I am, as he's currently 37, and this happened like 5 years ago, so it was when he and his wife were in their early 30s. And while I have one son in college, he and Jane never had any kids before she died. He says he has no desire to ever get married again, and it also seems like he hasn't dated a ton since the accident. But I can safely say that his lack of relationships is not due to any lack of interest from women, as Greg, on top of being the genuinely nice guy I described before, is no slouch in the physical appearance department either.

He's a high school history teacher and a basketball coach, and he's both classically good looking and in great physical shape. And even in the short time we've been dating, I've already seen and heard about him getting hit on by the moms at his school too many times to count. He even gets propositioned by women that are supposedly still married! So yeah, Greg's a catch, no doubt about it.

Losing his wife has definitely had a profound effect on him, though. The most obvious way, although to be fair I don't actually know how he was before the accident, but today Greg is not much for drinking himself, and not surprisingly, very, very critical of anyone who even remotely drinks and drives.

The fact that Greg hardly ever drinks has been a little tricky, because I do enjoy my fair share of alcohol, and drinking alone is always kind of awkward. So I will often offer Greg an adult beverage on evenings when we're hanging out together, but he will almost always politely decline. There are rare occasions however when he'll actually consume a few, and as luck would have it, our story picks up on one of those such nights.

Greg's closest teacher friend had his 40th birthday party tonight, and so we all went out for dinner and drinks at a restaurant that happened to be near my apartment. After the party wrapped up, Greg and I walked back to my place and now we're about to climb into bed, both still enjoying a little buzz from the beverages we consumed over the course of the evening.

Greg gets under the covers first and has on a pair of boxer briefs, which is what he always wears to bed. I have on a t-shirt, which is part of my normal sleeping attire, but before I get into bed I casually drop the other half of my outfit, my shorts and underwear, off my legs and onto the floor before climbing up and under the covers completely bottomless. I'm pretty sure Greg doesn't notice my partial disrobing.

Here's my plan. On a night like this, I could easily initiate sex, and I'm sure it would be great. Mainly because overall, sex with Greg has been quite satisfying, even from day one. But it's getting to the point now in our relationship where I'm craving something more. I want to know what makes Greg tick, sexually speaking that is. I want to share more about myself, including my own desires and turn-ons, but I really want to get a peek inside Greg's head. You know, to uncover the sort of embarrassing stuff that you'd never admit to your friends, and possibly not even to your significant other. I want to see if hidden behind this extremely nice-guy exterior is the secretly perverted grown man I so desperately want to find.

And with Greg actually having had a fair number of drinks tonight, I figure now is the time to strike, while the iron is hot as they say, or in this case, slightly drunk.

Me (snuggling up to Greg under the covers): "Did you have a good time tonight?"

Greg (giving me a loving kiss on my forehead): "Yeah, it was great. Seems like Chris had a good time, despite all that talk leading up about how devastating it was to be turning 40."

Me (sliding a hand across Greg's bare chest): "Yeah. Someday you'll have to join the rest of us in the old folks club. It's not too bad."

Greg chuckles and then slides his hand down towards my hip.

Greg (pulling up my t-shirt just a smidge): "Woah. You're naked?"

Me (leaning in to give him a kiss on the lips): "Yeah, is that a problem?"

Greg (smiling): "Definitely not."

I feel Greg start to move down, as if he's going to jump right into the activities, so I decide to catch him.

Me: "Hey, so... before you do that... I was wondering if maybe you'd be interested in a little sexy conversation to spice things up a bit before we start on the main event?"

Greg (clearly a little surprised and confused by my request): "You mean like... dirty talking?"

Me: "Not necessarily like dirty talking, more like a real conversation about fantasies or desires or things like that? I feel like we've gotten to know each other pretty well, but I can't say I know much about any deep, dark, fantasies or secrets you may have."

Greg (with widening eyes): "Oh. Okay. Well I'm not sure I have much to spill, but I'm happy to try and oblige."

Me: "Exactly. Soooooo... do you have any secret fantasies?"

Greg (thinks about it for a few seconds): "Well Becca... you know how much I love going down on you. I definitely fantasize about that when we're not together."

Okay, not off to the best start here. I'm well aware of how much Greg loves to lick me, and I would be insane to ever complain about that fact, but that's not the type of answer I'm looking for here.

Me (calling Greg out a little but in a joking manner): "That's hardly a fantasy and definitely not a secret. Ha."

Greg (sincerely): "Oh, sorry."

I think I may have to be the one to go first here. And that's fine.

Me: "No need to apologize. But here... let me give you an example of a secret of mine. And it's more than a little embarrassing, so don't judge."

Greg (giving me a kiss): "I'm actually really curious to hear what this is, and I promise I definitely won't judge. I swear."

Me: "Okay, good. Okay, well here goes... so you know how often times you'll see like a local news clip, and it's pretty much the same story every time. There's a mug shot of some pretty blonde woman in her 30s or 40s, but since it's a mug shot, she certainly doesn't look her best. Like her hair is all messed up, or she's frowning. And then the news anchor will say in a super serious tone how she's a teacher and she's accused of having a sexual relationship with one of her male students?"

Greg (laughs): "Yeah, I've seen news blurbs like that before. And then some meathead will inevitably make a joke about how they wish they had been a victim of some hot teacher like that when they were growing up, but they'll use air quotes when they say the word 'victim'."

Me (chuckling): "Yeah exactly. And believe me, I totally get that these boys are victims, here."

Greg (now looking like he has know idea where I'm going with this): "Okay... but this is like your fantasy though?"

Ugh. I can feel him already starting to judge me. This might end up backfiring. Oh well... I can't stop now so let's just see where this goes.

Me: "Not my fantasy. That's not the right word. But I am intrigued by these stories. Or maybe fascinated is the better term?"

Greg: "Okay, I don't think that's that weird."

Okay, good.

Me: "Yeah, it's like if I hear about some teacher like this, and for whatever reason it's always the female teacher and male student combination that really gets me going, then I'll immediately go online and google the name and try to find out all the sordid details. Like was it just one boy or multiple boys? If there was more than one, did she have them all over at the same time for like some sort of sex party? Did she give them booze and get them drunk? Did any of them get her pregnant?"

Greg seems like he's intrigued and listening to my explanation, and he doesn't look disgusted, so that's a plus.

Me (continuing): "I just want to know all the details... and yeah, this is the bad part... yeah, it definitely turns me on to hear what happened. I would never do something like that myself, but I'm curious to know about others who have?"

Greg: "That's really not that bad, Dear. Believe me, I'm not judging you in the least."

Me (feeling good as I was legitimately worried he was going to be totally freaked out): "I'm glad you said that. Thanks."

Me (continuing): "Yeah if anything, and this is the totally random part, I think my actual fantasy is to be like a juror on a case like that, like if it went to trial? Then I'd get to hear all the details, even the stuff that wouldn't ever become public. And I could see the teacher and the boy firsthand, and how they look at each other. I'd be so curious to know, like are they still attracted to each other? Do they ever give each other secret signals or interact in the courtroom, even though I'm guessing they're not supposed to? Yeah, I think all