The List

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Sexy older woman decides to give young tech hottie a chance.
8.8k words
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Part 1 of the 4 part series

Updated 06/09/2023
Created 12/05/2019
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Pros and Cons

You said it yourself. You don't do younger. There's a good reason for that. Or at least that's what you tell yourself.

The list of cons is long.

Younger men tend to be gauche.

They won't recognize the bands you like.

They haven't been anywhere. (Most of them, anyway.)

They have no money. And, the corollary to that - they have roommates.

They dress badly. Worse yet - they want you to dress badly.

In general, they watched huge amounts of terrible porn and 'learned' from it.

The list makes you shudder. Not to mention - look how it's worked out for older women. Demi Moore, for instance. One day, Austin Kushner woke up and realized he wanted kids and - wham! - Demi was history. Ok, so maybe it works for Bo Derek and what's-his-name. There's just something so pathetic about Susan Sarandon when she's hanging on the arm of some guy who's wearing his baseball cap backwards.

So you're always scrupulous to drop hints in your ads: silver fox, mature, sophisticated. But when you write the one entitled, "Aimez-vous Brahams?", you forget that the movie is about a May-December romance between a very young Anthony Perkins and 'woman of a certain age' Ingrid Bergman.

You forget but he doesn't.

He's the only one who references the movie. The movie you completely forgot about as you were just looking for someone to take that extra concert ticket. The extra ticket with the extra 'extra' implied.

His answer is smart. Very smart. He's 'younger'. Ok - that could be 48. That's younger. When he tells you he's 27, you pause. 27 is son territory. He was born the same year you got married. And yet...

What about the 'pro' side?

Perhaps you've been missing something?

You chat. He's strangely fascinating. Catches all your odd allusions. He's been places and he's even more educated you than you. You feel yourself caving - just a little bit.

He sends a photo. Yup, he's definitely young. There's still the barest hint of puppy fat. But the clothes aren't cringe worthy. He's got very nice hair. (You remind yourself to put that on the 'pro' list - Unlikely to be bald.)

Besides, he seems genuinely interested in the concert. You send a photo and he's not appalled. In fact, he tells you he's been with older women before. Indeed...

She picked him up in a cafe when he was an undergrad. An undergrad?! You think of all the students you've had and Mark MacDonald instantly comes to mind. Oh that kilt.... You shake your head. You'd never have hit that. All 6'5" bearded gorgeousness. Oh god, maybe this isn't a good idea after all. And yet-

you envy her her spirit. She must have seen something there and then reached out to take it.

Something you could have now...

You chat on the phone. He has the most seductive voice. He doesn't sound 27. And even if he IS 27, he's definitely an unusual 27 year old. He shows you a photo of some bone like thing he's built. It looks delicate and it makes you wonder if he's good with his hands. You ask for a photo of them. (He doesn't need to know yet that good hands on men make you swoon, that watching men drive stick shift makes you wet instantly.). He does and there they are - slender and brown, next to some rubic cube thing he's also built and you begin to think you've been unnecessarily prejudiced against the young. After all, how are young men to gain experience...? And once again, you're silently thanking that unknown Meaghan and wondering what exactly she taught him.

*

And then there's the problem of your weekend away. That rare, lovely weekend and only one day planned. You've already asked everyone you can think of and no one can come. M has his anniversary. E is in Japan. S has his favorite charity golf tournament. C has some Burning Man obligation. It could make you scream.

But this guy is free. The guy you've dubbed NMP - 'non-mormon person' - when you find out he doesn't drink. Not because of religious convictions, apparently, but because he's no good at it. Can't get out of his head even if his body refuses to answer his brain.

Well, that's not a deal breaker. What could be - should be - a deal breaker is the fact that you've never even met. And you have never, ever made arrangements to meet someone like that without having checked them out in a natural situation first. Scratch that - you did ONCE and it was an unqualified disaster.

You test out the waters. What if we don't spark? He's ok with it being a platonic dinner and some hot tubbing. Hmmm... You could be generous. After all, struggling young engineer...it would be a good deed. A mitzvah. You've got all that room. He is interesting...

You make arrangements, partly cursing yourself for being an idiot. This could SO backfire.

He could be all of the things on the 'con' list.

All the way there, you consider calling it off. But you'd feel bad. After all, he did drive quite a distance. So you screw your courage to the sticking point.

And there he is. Taller than you expected. Well, one thing is true - he's a terrible dresser. Still, his smile is friendly and he's as easy to talk to in real life as he is online.

You change into a dress for dinner. A low cut wrap dress with gray sandals. If he approves, he doesn't show it. He drives because he's not drinking. His van is indeed the beater car he said it was and somehow it puts you at ease. He finds a parking spot right by the restaurant - a minor miracles - and you take it as a sign.

Dinner is weirdly easy. You both loosen up and you find yourself looking at his mouth. He's got the sort of plush lips you adore. And you notice him noticing your cleavage. Till now he's been scrupulously polite but it seems to come naturally to him. This is freaking him out a lot less than it is you - possibly not all.

The conversation on the ride home is engrossing and continues as you go in and lie down on the bed. He joins you and it actually takes a while before you notice you're having an obvious 'wardrobe malfunction'. Your breast is mostly exposed and you've got no desire to tuck it back in.

In the soft light, he looks younger than he did at the restaurant. Hopefully, you do, too. Nine out of ten men would reach for that breast right now but he doesn't. Instead he moves to the end of the bed and takes your left leg in his hands.

His crazy, gifted, strong hands.

There's a scene in one of your favorite movies, Hang the Red Lantern, where the favored concubine- the pregnant one! - gets a foot massage. Some old Chinese lady lays into her feet with a small hammer and ... hmmmm...

He's clearly no old chinese lady and yet - what he's doing to your feet is making you feel like butter in a warm pan.

And making you wonder what those same hands could do - elsewhere.

But, luckily, you don't need to think about that right now. You're belly down so he can't even see if you're enjoying this. But you are and, every once and a while, a small purr escapes your lips, making it amply clear.

He could go on like this for hours, as far as you're concerned, but, of course, he's not going to and - when he releases your sighing leg - and moves up to the head of the bed, it comes as no surprise to you when you're face to face with his eager cock.

It should come as a surprise, this new young cock but it doesn't. When your lips meet it, it seems like nothing less than its owner's due. You're so relaxed - when it slips into your lips, it's like ice cream. You can't have ice cream but you can have this and it has the same melting sweetness.

You could lick him forever. It tastes like warm frozen yogurt and cardamon.

You'd probably just keep doing this except he's rearranging you, sorting around under your dress.

Suddenly, he's snuffalapuagus. His mouth is everywhere under your dress, probing, tasting. He's an engineer and he is going to work to optimize this machine for his pleasure.

And when he begins fucking your ass with his tongue, your cunt stops being jealous of your feet.

You were born with bones. You know this. and yet, in this minute, you are akin to jelly fish. You have no brain and it matters not at all. You will move back and forth on the tide that is his tongue and it will be fine.

Better than fine.

Pros

Uninhibited. The past 20 some odd years have done away with a shit ton of no-nos.

Energetic. There. is. no. pill.

Hair. Did I say 'hair'? Yes. Hair. Gorgeous. Dark. Hair.

OMG. In the past twenty years, God has seen fit to give men mouths. Not just for kissing (though - dear God - that, too!)

When he asks - does this make you feel full? You're so full, you can't answer. There are no words for how his hands inside you make you feel. A million years ago, when you were a single celled animal in a warm salt sea - then, then, you knew the word for that feeling.

When shells break apart on the beach because of the thrust of waves, they feel this way.

When the fox sinks his teeth into the neck of the hen, this is her last thought.

This is why this is verboten. This is why you never did this.

Because his hands are crack. And he knows enough to take them away just when you want them most. He wants to know how much you're prepared to offer.

And yet - he's no better off. You can tell. If you turned off the faucet between your legs, he'd stay there like some abandoned dog - waiting, his tongue hanging out. When you scoop out your wetness and bring it to his mouth, he's like one of those sorry 49ers, who'd trade gold nuggets for a drink of silty water.

Indeed. He's drinking at your cunt like it's some crazy oasis. He's been wandering in a Silicon Valley desert and suddenly! There's a body like a palm tree complete with coconuts and by God! He's going climb it, crack them and drink till he falls.

when he finally gets the condom on, it's an afterthought. you're so punch drunk, he could do anything. or nothing. It doesn't matter. you're glued to each other like ambisexual earthworms - either side, either way, sex is happening. has been happening. will continue to happen. however you happen to be connected.

Did you get into the hot tub before or after? You should remember a simple fact like that and the fact that you don't is more proof that sex makes you stupid. And he makes you an absolute imbecile. What did you actually plan to do with him afterwards? How many of your lovers have begged you for a whole night - sleep, sex, food, sex, sleep again. Perhaps not in that order but it would have been something like that - something unhurried.

There is another bed up in the loft. You don't want him to feel obligated...

How do you feel about sleeping next to someone?

He laughs and claims he was about to ask you the same thing. Suddenly he looks his age - sweet and cuddly like an overgrown puppy - and so very, very happy. It comes as no surprise to you that he's good to spoon - arranges himself so you align smoothly against his shoulder, his one hand cupping your breast, his cock almost tucked into your tail. You told him you don't sleep yet tonight you both do, the sound of his light snore lulling you into the same rhythm as his breath.

It's only a queen bed so - occasionally - you shift. Or he does. This is not really wakefulness, more like something in-between that and a shared dream. In this state, it's especially easy for your lips to find his despite the dark, for his hand to trail up between your legs till you're turning again to give him better access.

How long has it been since someone woke you in the middle of the night for sex? For MORE sex. He makes the night both infinitely longer and collapses it entirely. The things he whispers to you are the things you've heard in your dreams so there is no reason to separate what's going on now from them.

There's a japanese print called Dream of the Fisherman's wife that shows a woman writhing in the erotic grip of two octopi. You can't remember when you first saw but it's stuck in your imagination ever since. His hands are everywhere and his mouth tastes briny. Yours does, too, and you can no longer tell if it's your flavor on him or his on you. The whole room smells like ocean - a combination of salt and sweat and the faint tinge like stranded kelp heated by sun. It might be that you suddenly understand what that print was truly about.

Pro

Insatiable. (Note to self - possibly also a con)

In the light of the next day, it's a bit more awkward. You've got zero breakfast so you hand him an apple. (Yes, a friggin' apple!) He's got to go because you've got the conference. AND you're booked. Double booked. While you're watching him dress, it occurs to you that the warm up band has suddenly become the main attraction, making you feel lucky and gypped all at once.

He's surprisingly ok with being summarily evicted. After all, there is the concert...

****

There is a week in-between the weekend and the concert. Plenty of time for your sang froid to return. But somehow - it doesn't. Thoughts of him intrude upon your brain at the oddest moments. You hear someone counting and immediately you're transported — how did he think to count those anal beads from inside? Maybe he counts everything. He could be the "Rain man" of sex? Perhaps you've fallen prey to some sort of sexual idiot savant? That would actually explain a lot...

You shake your head, thinking that will clear him out.

But he refuses to leave.

For one thing, like all members of his generation, he's surgically attached to his phone. And he's not afraid to use it.

What are you wearing?

Go to the restroom and take a pic of your muff.

He wants you to grow "it" back. You should be thankful - there's $60 a month you've saved, not to mention the pain.... But you can hardly picture yourself with

pubic hair, it's been so long. Really? Is this some sort of retro thing...?

show me show me show me

He seems like he has an awful lot of time on his hands, especially for someone who claims to work for Boeing.

You ask him if he'd like to play 20 Questions. He's game so you start.

What's your full name?

He tells you without hesitation. It's not the name he told you before but that's normal for the internet. The first name is more obviously Indian than the name he 'goes by'. You tell yourself you really shouldn't google him but you find yourself doing it anyhow.

He's so young. Chances are there won't be anything anyway...

How wrong you are!

Oh. My. Frigging. God.

Remember when all your girlfriends were reading 50 Shades of Grey and you tried to tell them what crock of shit it was. A 23 year old VIRGIN from PORTLAND? If there were actually such a thing, she'd more than likely be having LESBIAN BDSM sex. A super hot young TECHIE gazillionaire? Yeah, right. You've seen those guys and they are definitely NOT HOT. They're all mathematical awkwardness.

And yet here he is.

You scroll down the articles. Forbes. Wired. Revolutionary. ... changes the conversation. Rethinking....

You stop. This feels like spying. Why should it? These are all public articles. It doesn't change anything. Does it matter he didn't tell you he's some hot shit start up entrepreneur?

Of course not. Except you're suddenly flooded with the red hot certainty that he could have anyone if he put his mind to it.

You text him. What do you really do?

I fix things. (Yes. Oh yes. You certainly do...)

Which makes him sound like some sort of 21st century handyman. Yeah, lady, if I don't get up under there, that's just going to keep leaking...

You want to slap yourself. Fuck. You can't relate everything to sex! What's wrong with you!?

Like what?

You can practically hear him laughing.

Problems companies have.

What companies?

He rattles off a bunch of names you wouldn't have believed a half hour ago but now...?

You fix things? That's it?

Yup. That's it.

It's weirdly attractive - his matter of factness. As if there were nothing unusual about a 19 year old flying business class with a black AmEx card he can't even use to buy himself a glass of wine because he's too fucking young...

I fix things.

Yes. Yes you do. That fill-in-the-blank fantasy — the blank is no more. Those doubts you had about the existence of a so-called C spot? Gone. Not sure there is anything like a 'full body' orgasm? WRONG! Remember how you tried to convince yourself there was no man who 'just knew'? Wrong again. You think about his hands and shudder.

20 Questions was a mistake. He likes what you like. He's just saying that. But how would he know?

Do you have ben-wa balls?

Yes.

How many? There we are. Counting again.

You dig out your toy bag. Six. (How the hell did you get 6?)

Six.

Put them in.

All of them? He's crazy. You've tried two and that was hard enough.

Four.

He's definitely crazy and there is absolutely no reason you shouldn't say - fuck that! Or simply lie to him. How would he ever know?

And yet you know - you won't lie to him. Because he would know. Somehow. And - suddenly - you want to know what he knows. Can you?

You can and you do. 4 balls.

Good girl.

He's got a lot of cheek, calling you 'girl'. You could be his mama...

But there they are - 4 ben wa balls rattling around inside you. Reminding you all damn day long that your boy toy lover likes how tight you are. Reminding you how you flushed all over when he whispered: I can feel your cunt clutching my cock...

It's not like no one has ever said anything. You've seen their eyes dilate

when you cum on them. They know. You know they know. And yet no one's been so unabashed. He's absolutely delighted by your body's machinations,

You could swear he's just fucking you for information. this is how the female sex organs work...

And yet then he says these crazy, unexpected things.

You're precious. Precious? Has anyone EVER said that to you?

It's my job to coo encouragement in your ear. Coo? He's going to coo? Who says that? And yet you know instantly - that is exactly the right word. That is exactly what he's doing and - by god! - it works.

When he tells you...

I want you to come so hard

You are 100% certain your orgasm will blow the top of your head off just because he wants it. Because he asked.

*********

You're no great believer in phone sex. It seems like something only desperate people would do - people who can't have real sex (whatever that is). Phone sex is for seedy old men who have to pay to have sex but are too cheap or chicken to spring for a hooker. You've tried it before and it was awkward and unsatisfying.

But, then again, did anyone have a voice like his? It's oddly unlike his body - both more like him and less somehow. Up close, he looks 27, still slightly unformed, fuzzy around the edges. (Though, it occurs to you, that could be because his taste in clothes leans towards NASA t-shirts paired with beat up sneakers...). But his voice! His voice is already the man he will be - deep, rich and unhesitating. It goes down like Turkish coffee - sweet and strong and intoxicating. It never fails to give you a jolt. You know you should treat it like Turkish coffee, too; there's a reason they serve it to you in such tiny cups.