A Guide: Maneuvering 50K's into Bed

You wonder: Maybe it makes her feel unworthy, like she must compete even more?

You meet everyone, including the sister, who is actually a bit of a trainwreck and demands attention constantly. Things start to make sense: She's the athletic and pretty one. By conventional wisdom, you're with the merely second-choice daughter who still hasn't figured out life yet. Even in middle age it's a struggle, as it always will be...

You smile and say only a few words to the dozens of people you're introduced to, which is one of your superpowers, because -- these days - people assume you must be a real catch if you have manners and ask sincere questions and listen to the response.

Yes, it suddenly appears that in the last few years society has lowered its standards that much. Or maybe it is merely a reflection of the quality of man her family is used to her bringing around. Whatever. Don't worry: This is good news for you!

However, that haircut you got yesterday, which cost -- $80! -- and your best fitting suit is doing a lot of the work (like a real pro, you even coordinated your belt and shoes). Okay, the German sauerbraten and schnitzel are, in fact, amazing. #1.) Don't mention this in front of her, because she'll get mad at her sister for making an adventurous and good decision. #2.) Don't get mustard on your shirt or tie.

Meanwhile, you contemplate a few important things. For instance, how overwhelmed her choice of dresses is... She is obviously competing. There is a loooong line of cleavage showing; a hint of sun-created freckles on her upper breasts that is somehow gorgeous, probably because it dramatizes the depth of that crease created by her udders. Because, yes: Udders.

These are massive-fat-girl-super-tits pushing at clothing not designed for them. She knows what her selling point is against her sporty and high-cheeked sister. Maybe, also, because she read your expression that first night?

And don't forget, when she bends forward to straighten your tie as you sit down, it is possible to imagine what her peaks might feel like in your mouth. Imagine them: Supported and yet smooshing around and between your fingers as you consume them for hours. You have zero idea but imagine you're looking at the suggestion of twenty pounds or more of tits. Don't screw this up.

You bring out the lie a few times concerning that 1974 Jaguar with zero rust, which also brought you out here to the dry southern California climate on a happy coincidence, but no one cares. They think you're the boyfriend! Even though it's only been one date and a bunch of phone calls -- which were mostly about you being that good listener.

Some random men look at you and know: The only reason you made the trip and did everything else is because of her insane tits. It's understandable but also an asshole move. Still, can you imagine her on her back? The way those tits would slosh and spill around and just urge you on?

What did someone once say? Half of life is just showing up.

She's showing you off. She frequently takes your hand and leads you around the admittedly cramped little German restaurant, which is doing its best at this "event." It seems people don't use the word "party" anymore.

"There are two beds in my hotel room," she says. "You can sleep in one, if you want."

The Weather Channel:

You're already positioned in a TV-watching-pose in the second bed, covers only pulled up halfway, when she appears from the bathroom wearing nothing except an oversized and very long T-shirt with a faded image of the Colorado state flag stenciled on it.

Her legs are kinda' plump-cute: Does she know that? She still has that hairspray hair. Except her makeup has been removed, so her features have disappeared even more from her face, which is an unexpected thing to suddenly view.

So, yes. In a move of pure obviousness, you are displaying your bare chest. You prop yourself up against the headboard and a pillow, bent at the waist, fiddling with the TV's remote. The sound is off, and a weather map of the US is helping to light up the room. What? This is just how you sleep: In your boxer shorts and nothing else.

The glow from the TV, along with one of those cheap and awful nightstand hotel lights (that makes everything too sharp and obvious in one part of the room and shadowed and hidden everywhere else) is undeniably seductive in its own way. There's mystery and then there's clarity.

Her tits sway, jutting forward like pendulums. They're fighting for freedom underneath that flimsy misshapen / ostensibly no-sex-tonight shirt, because she's braless. Thank God your lower half is covered by the blanket and sheet. For the last 4 hours in her company, you've been managing a semi-erection and now that unbelievable side-to-side breast-sway is forcing you through your boxer shorts in a way that seems truly supernatural. Even in the relative dimness where she suddenly stands, trying to decide what happens next, she looks like she's trying to argue AGIANST herself. She's against whatever is actually happening, while simultaneously trying to encourage it.

You innocently ask: "Wanna maybe watch a show or something?" You've selected the bed closest to the TV for a reason.

"Sure," she says, and you try and avoid gawking at her as she walks the distance over and then places herself atop the covers, and abruptly she's right next to you.

You catch a memory of that legs-out Match.com photo, which also captured your imagination in a surprisingly complicated way. Her ankles are thin and almost dainty. Her toes are painted red - maybe because she is now trying at life in all sorts of little ways? At least for this abnormal weekend. Her back is propped upright on the pillows, and she is positioned just like you.

However, the significant difference is that your naughty bits are underneath the covers, while her unbelievable breasts now spill hugely to either side of her torso, contained and covered only by the thinnest fabric imaginable. She's maybe letting you know, again. Those masses of femininity stretch and overextended that Colorado flag, making her an astounding presence. They are simply THERE, as mounds of sex, and in ways that challenge your supposed familiarity with women.

You're just a man. She's presented like a strange cartoon fantasy, frumpy no-sex shirt and all, and yet she doesn't truly realize exactly how much it affects you. The more ordinary she appears, you suddenly think, the more she turns you on.

"There's a storm on the way, back home," you say, as if the weather is on your mind, although you raise your arm and sorta' wrap yourself around her shoulders, drive-in-movie-style, pulling her close.

Maybe, you'll both just sit here and watch the Weather Channel with no sound on? Snowplows are on the screen, reminding you of something: That you are both on a vacation and far away from your other -- sometimes - messed up lives.

Something Happens Under the Covers:

You've done this arm-around-her thing immediately, almost without thinking about it. After so much handholding and being in each other's proximity constantly for the last several hours, this isn't necessarily the awkward move you expect. She leans in; you glimpse her tits reposition under the fabric with the change in her orientation, sloshing sideways in an erotic offer of all-night breast-obsession, which she is apparently oblivious to. Or not?

Except then, her hand travels under the covers and finds your monumental cock, even before you've kissed on this night. Before you've made any kind of romantic gestures beyond the most basic ones. Holy hell: Something is happening.

She plays with it gently -- saying nothing - to understand its size and shape, and then whatever desires she kept hidden begin to become apparent. She scoots your boxer shorts down your legs without a single word.

Still...at first, it's like she's almost embarrassed. That word, again. She doesn't want you to know. Not really.

Immediately, she's snuck her whole self under the covers. She kisses your stomach on the way down, because she wants it to be romantic. Because she likes your body. Because she wants you to anticipate it.

There she is rendered: A woman's form kneeling under a blanket and a sheet, so that her mouth is right where it will do the most damage to your composure. She doesn't want you to see, perhaps, or she is also pretending that it's not happening. She's conflicted, you think. You want to tell her: "It's okay to be this girl with me. In fact, it's everything I desire. You're a fantasy."

But you are holding back too. You worry about showing her your true self and lust for her. Because then she'll know. EVERYTHING.

From a mechanical or logistical standpoint, there is no need: Your cock is at maximum strength. It is unquestionably fully deployed and operational and ready for its first San Diego mission. And yet she is sucking on you like she's performing textbook-style foreplay before sex (To Prepare the Man for Intercourse, Chapter 3).

Throwing the Textbook Away:

She's sucking your cock because it's been years, you now understand. Yet this is also just a friendly bedtime BJ, as you contemplate caressing her insane tits. You understand (somewhat correctly): Sex is a physical release for her. That's what she's providing for you too, she thinks.

And then you run your hands through that still-crunchy hairspray hair underneath the sheet and something changes. Your restraint is crumbling with the sensations she brings, as you actually start to feel her. The scrambled thoughts in your brain - THIS IS ACTUALLY HAPPENING - are starting to fade, while the pleasure is starting to coalesce. Be a hedonist, you think. Enjoy.

You hold her head and help yourself even more into her mouth and she moans a muffled blanket-covered sound.

You open your eyes to see the lumpen shape of her underneath the covers. The satellite images on the TV are marked with a red swath through the middle of the country, and that erotic form under the covers is now bobbing up and down and you are feeling EVERYTHING but also wanting to see EVERYTHING and show EVERYTHING.

Can you imagine those plump cheeks pulled in as she sucks? She is now lavishing attention in a way that makes it okay for you to hold her head again. The sex textbook is set aside. There's that muffled moan. Whenever you do it. There's that confession from her. All at once you reach further down and grasp and then cradle a massive hanging udder in your hand, because that is what they are: UDDERS.

The flimsy t-shirt is stretched, and God, now you are finally holding a breast in one hand. It's soft. It's ungodly huge. It's HEAVY. It's pliant to a point. And then firm. It's smooshing into your hand as you support it's swinging mass. Nothing else feels like that. God, the weight. Her nipple is presented and studied by feel, bigger even than you imagined. You think back, and remember your first assumptions: they were each apparently like the fat cap to a felt tip pen. But now it is more like a marker.

Her breasts are offered as an addendum to the blow job, but they are - in fact - equally mesmerizing. Your hips rise off the bed, because you can't help it.

This moment started as an erotic Hallmark card, but it is headed somewhere else.

It's a 'Thank You!' from her for being a perfectly decent man to show off - but also, there's that moaning sound. And your needs - and her needs.

Your restraint is falling apart. You hold her head and raise your hips off the mattress to urge more of yourself into her mouth. You're half-fucking her mouth and every time you do it there's an approving sigh. You understand: You can ask an awful lot of things from this titanically breasted woman right now. One hand is holding one of those magnet-breasts, while the other hand is guiding her head. That's pure pornography.

Pink Chiffon:

A man with an ordinary job and sensible haircut might have just succumbed to the pleasure -- and the idea -- of what was happening. But right now, you're not that type of person. You are the guy who lied about wanting to fly a thousand miles to checkout a barely running 1974 Jaguar sedan. You lied to her aged aunt and uncle, her sister, and everyone you met in some manner. One of a hundred white lies that have accumulated. Because of the most incredible tits, and maybe some other things.

In fact, it would have been easy to relax and lay back and coo your appreciation as she does that early-in-the-relationship-fellatio-maneuver, which is simply heaven. The before bedtime BJ so you can sleep the deep restful sleep of the recently drained man.

But...

You could push the lies aside. You could REALLY concentrate and feel her deep kisses around your cock, which also feels like she is kissing your whole body. Her tits. God, her tits hanging in your hands. It's so good. You lift them up and let them sway. You tell her: "You're amazing." You are becoming the first amount familiar with a huge-breasted-blow-job. But there's something wrong, because you don't want to cheat the truth.

In almost one movement, before she has an idea of what is happening, you're reluctantly pulling out of her mouth and then pulling the covers back. You're turning her on her back, that flimsy shirt again covering the two hanging-mountain-targets you were just taking turns fondling. You're expertly pulling down her panties. You see a perfect triangle of pubic hair in the midst of those fat hips. On top of her now, she's starting to understand, as are you.

The hyperclarity of that bedside light is making a statement. She gets her first real sight of the item that was just an instant ago making her moan in ecstasy, which is now dangling from your body in what you don't realize is a VERY masculine sight. Neither of you would ever say the word at such a time and so early in whatever this might become, but you both want to fuck.

But then there is that other revelation.

"Do me a favor," you say. It's a weird thing to say.

"Okay."

"Put on that awful bridesmaid dress. And put on those neon pink shoes that go with it."

Maybe she understands something: You want to have sex with her - with that dress on her body. Or more likely only half on her body. You two are going to share some kinky weirdness together in a hotel room so far away from your lives. You are going to take something back from the world and own it for yourselves.

"I'm not on birth control," you hear.

"Okay," you say.

She's going to allow you to cum in her mouth or between her tits several times tonight, she is apparently telling you.

People are Going to Know:

Tomorrow afternoon, when she stands up in front of everyone at the wedding, alongside those other much thinner and smaller-busted bridesmaids, she's going to be wearing that same pink dress and matching high heels. You watched with silent delight as she opened and rooted around in her suitcase to find the shoes, just because you asked her to.

And it's the same dress that now enters the room on her body from the bathroom, her hair still crunchy, no makeup on her face, the heels adding a couple of more inches to her height and making her legs now appear genuinely plump-awesome. Oddly, it's that moment that makes you want her in truly romantic way after tonight.

You are trying to find something to correspond to her earlier complaints about the aesthetic qualities of the shape, color or style of the garment -- on her, it seems to advertise her breasts in an excessive manner -- which is obviously perfect for you. Was that the REAL PROBLEM she had with it?

If so, then why did she choose to wear a dress to the "event" tonight that accomplished the same thing? A dress that emphasized her breasts. There are so many disagreements and paradoxes with her that a person can't sort through them all.

Tomorrow, that pink dress is going to be smoothed and ironed and ornamented with a corsage, but in this other incarnation the dress is designed to be pulled down and hiked up. It's like a sort of prom dress worn with honor by the sluttiest girl in high school. The critical fact - that it is now instead on an obviously middle-aged woman in a hotel room - is even sluttier. The cheap high heels definitely help in this regard.

Maybe, looking at you, she's beginning to realize something: Her size, her downward trajectory, her life-failures, her face, her fat, her irrationality - including her breasts - combine into one person. And that's all fine for you.

You stand up and walk towards this second date experience. She's still easing her way to the bed, slowly and modestly, but you intercept her halfway, her eyes very obviously watching your cock bounce in its needful state. And then you hug her, almost like that first date hug, now recast more than a week -- and several revelations -- later.

The expectation of All Night Sex is very apparent as your cock smooshes into her pink-covered stomach. The two of you are obviously not going to be showing up to the breakfast "event" tomorrow morning at 9:00 a.m.

People will not talk, but people will still know. Missing breakfast means you two fucked over and over last night and had to sleep in. Your mouths joined in long kisses as her plump high heel-adorned feet bounced in the air, spread as they were with legs hooked around your arms. They'll somehow know it was that kind of night.

Clearly, the second-choice huge-titted-sister was used for an unlikely event in her life: fantasy hotel room sex.

Until then, your mouth is on her lips in a soft kiss; your hands are on her sides. She's deeply kissing you in return. Arms around you and grasping you for reassurance. Okay, she's fat. But this time you pull back and your hands travel to those breasts. You moan, sigh and shiver and feel them through that supposedly awful fabric, and then you whisper in her ear: "Get down on your knees."

A File Cabinet Full of Needs:

How many of the other bridesmaids are getting this treatment tonight? How many of them are wearing their dresses without anything on underneath, so that when a man's hand slips between the fabric and her skin there is nothing to insulate, support, or play defense?

Your first thought is how much her tits make you want to simply fill her with cum. It's an amazing transfer of libidinal urges. On her knees in front of you, that nightstand light is working a sort of pornographic exposure; you catch a sight of her middle-aged features as she wastes no time adopting -- again - a certain pre-intercourse role. The idea of her breasts go straight to your cock, which goes straight to her mouth. Later, the idea of her tits will pull you into her pussy.

You guide her and tremble and want to lay down because she makes you wobbly and unsteady. Why are fat girls so good at sucking men off? Because they're HUNGRY. But you can't let it happen so soon...so easily. You withdraw and lay your cock on her face and she immediately kisses it, maybe astounded that you are showing how much you want to just play the kinky, lazy hedonist with her. Even at this time of night. An urgency born from years of desire also means the two of you want it to last. She holds your cock in her hands and returns your gaze, asking -- maybe -- for permission to be your partner in this plan.

Maybe she's sorting through her own file cabinet of needs and wants? She never did this sort of thing with the 80's metal cover band boyfriend, even after several years together supposedly building trust and compatibility.

She wants a relationship. She wants a stable guy.

Despite what's happening, THIS was the year(!) to get things DONE. Turn a corner. Get rid of those old and ill-fitting clothes that continue to clog up her closet - or to get rid of the sugary food that crowds her refrigerator -- neither of which has happened.

Instead, some guy found her online. And now she's getting face fucked by that very same weirdo-aficionados of huge breasted women. In a hotel. On what qualifies as a second date. The very thing that she DIDN'T want to have happen, supposedly.