A Guide: Maneuvering 50K's into Bed

First Date:

Of course, she knows her breasts are enormous. And now she knows that YOU know her breasts are enormous. About 20 minutes into your first date together, she gives you a half-smile which grows into a full-smile, which seems to say "Yes."

It happens unexpectedly. The woman -- who is old enough to need reading glasses when she scans the menu - is readjusting in her seat.

She's a little past her prime now, perhaps as you are, and those glasses are just one of many features which mark her gradual decline. You contemplate the subtle wrinkles by her eyes and lips; hair that is styled in a perfunctory and indifferent manner. This is particularly unfortunate because it makes her seem like she has simply given up in other areas of life.

But then you watch as she turns, offering you her profile, and she waves to capture the attention of the waitstaff.

And when she twists at the waist and raises her arm, her otherwise lose but suspiciously burdened Ross Dress for Less sweater tightens across her chest and reveals something which is far beyond your experience. Right in front of you - the silhouette of her udders. Because THAT is definitely the word. They are suddenly -- heavily - pushing against an otherwise ordinary garment. You understand this sweater also doubles as a disguise.

However, it is - for a wonderful few seconds - unable to complete that task because of what lies underneath: Udders.

Good God.

Beneath that sweater is surely an industrial strength bra struggling with the weight / volume...it's jutting massively forward. And you remind yourself -- THIS IS THE WOMAN YOU ARE ON A FIRST DATE WITH. Don't screw this up. Don't act like an idiot.

Even so, she sees a certain look on your face. There is that half-smile from her that says she is weary of disclosing her complete self, but perhaps trusts you enough to make a half-leap. And then her expression changes into a full-smile. Yes. She knows exactly what objects have you agog. And then later the way you keep glancing and waiting for another moment that will again tighten an otherwise mundane piece of clothing - she notices all of this (even while she continues to talk).

Is she interested in you? Is she secretly glad that you suddenly KNOW and are clearly happy and astonished with her? You find it impossible to read her past a certain point - or to adequately hide your focus on her body. You think back to her Match.com profile. You're the stable guy she wants, right?

Without another revealing motion, however, all you can do is sneak hopeful glances at her sweater camouflage, which is a piece of clothing she obviously selected from her closet for Strategic First Date reasons.

Extrapolating Her Size:

She doesn't want you (or the rest of the world) to know what 50K breasts truly look like. That stunning size is right there on her bra tag, although you don't know this yet: Eventually, you will glimpse this tag when you awake in a hotel room in the middle of the night. This will happen when you wander into the bathroom, catching sight of her open suitcase on the way, and bend down and rummage through it -- so very quietly -- to satisfy another part of your insane lust. Her tits and her coyness make you act like a person you are not normally.

Right now, however, you're doing your best to decipher the situation and extrapolate based on curves and wobbles. You could already teach a class on this thanks to this brief time in her company. Sometimes, she briefly straightens her back to correct her posture, and then it's more obvious what is just a reach away from where you sit. Is that the hint of her nipples? Jesus.

Meanwhile she talks about her nephew. This is a person who wants to join the Coast Guard but doesn't have the necessary grades. It's a mindless topic that means nothing to you, although you pretend otherwise, and offer helpful words and furrowed eyebrows to show concern. This is a sort of conversation that will reappear during the next week and more, as she talks and talks...

Later on, she allows that she -- herself - dropped out of school just a semester before getting her degree, and now it's too late to do anything about it. Soon after, she confides that she once had a car repossessed because she didn't make the payments. You have a feeling there are many more of these types of unflattering conversational / confessional topics yet to come.

Still, every so often she moves (and the half-light inside the restaurant finds a new way to undo all of her efforts at cloaking herself) and the reality becomes apparent: She has some extraordinary breasts. The push-shape. The weight. God, the weight. You haven't REALLY thought about that before. You contemplate those two mounds, which defy anything you've encountered in person. Standing behind her, you'd have to heft them up with serious effort. You try to keep from saying the obvious: "Holy hell."

It seems she is familiar with the dawning of her breasts on a man's mind, even if you're not.

Online Shopping:

Sure, she posted pictures that gave a suggestion, but she's probably frustrated by the type of attention she receives when she really gives a sense of their enormity. These days she's more reserved around men. A couple of decades ago, they were -- Yes -- already very big, but she's gained weight since then, and now? Good God. Does simply getting older make breasts bigger? In her case, it apparently does. Various midlife changes have worked a sort of mystery on her body.

It's just too much mass right there, she knows, and they just keep on growing; now, when she orders bras online she's going to the dropdown menu and selecting from the 'K cup' options. She feels dowdy. Unsexy. But at least the straps are wide, so they don't cut into her shoulders. The cups are structured to support serious poundage. Her bras are thusly "engineered."

It's embarrassing to her. Well, maybe that's not the right word: She is worried this is a particular physical characteristic that defines her as a person. These two encumbrances are bad for her back, particularly if she slumps, so she continually checks her posture, which only makes them more obvious in public. Clothes for that difficult and copious region are thereby conservatively selected and with an unflattering looseness. Breast-deniability is a top priority, as it has been for years now.

At home in her kitchen, it's the same.

The cabinets are full of soy milk and there's a blender for those good-intention-vegetables sitting in the bottom drawer of the refrigerator. She's signed up for Hello Fresh. But then there's also the four containers of ice cream in the freezer. On Sunday mornings, it's donuts. When she sits in front of the TV and watches Dateline, she's digging into the potato chips. Of course, she feels guilty, except nothing has changed aside from the size of her body -- and the size of her tits, which have seemingly overdeveloped by four times what might be expected.

Match.com:

Unsurprisingly, she's trying to reinvent herself in other ways.

At this point in her life - and without a Significant Other to enjoy the holidays with - or to take along with her to her sister's wedding in San Diego (this is going to be her second wedding in only three years **eyeroll**) there is a sudden emphasis on the emotional and intellectual qualities of life.

She wants men to know she's romantic; she's into board games; she'll read anything about the fascinating Anne Bolyne. She wants a RELATIONSHIP. Did you read that? She mentions it twice in her profile. Also, very important: She has standards when it comes to men.

So, yes: She creates a generic dating profile and fills the space with the usual sentiments, but also exacts a type of revenge against her last boyfriend when she underlines her expectations for a 'mature man.' As you will eventually learn, her previous man played in an 80's metal cover band **exasperated sigh** and probably cheated on her numerous times. (In fact, this remains a worry. She and him barely had sex their last few years together, and she often concerns herself with this lingering resentment. It surely doesn't help her body image.)

She checks the box for 'BBW' on several dating websites and other times 'full-figured' and 'ample,' and once 'a couple of extra pounds,' which is a complete lie. Soon enough, she's conservatively displayed in many places on the web. She warns men she's 'really, really curvy' - but otherwise avoids the topic.

She's urging the life-pendulum to swing the opposite direction: She's a mature woman, now! The physical world is being traded in for the mental and emotional one. She expects the same in a partner. Are you 'stable'? That's what she wants!

In her profile, she even writes the shriveling 'no time for games' phrase. And, like a lot of other things, she's unaware how cranky and unfun that makes her sound - almost like she's given up.

Online Sex:

Contradictions are everywhere.

She hides and avoids drawing attention to her sexual self, even though her vibrator is on Yellow Alert in the top-drawer bedside her bed. She's made a commitment to the sextoy by buying rechargeable batteries.

This thrice daily activity is "stress relief," she decides. It helps her sleep. She often watches what is euphemistically described as non-consensual material on her laptop. Videos of such material figure prominently in her stress relief; she has many of these scenes bookmarked, including a 20-minute video that is correctly titled Forced Oral Slut.

Her sextoy works its magic on both her insides and outsides. This activity enthusiastically happens while she views the men in her most-watched video: Their cocks are insistent. Importantly, the woman kneels on the floor like a sex slave. She is traded around. The men's hands hold the woman's head. The woman is used. It is a type of scene that ends with each man ejaculating on the blindfolded woman's face, though she rarely makes it that far. It's like they're doing something to her that is completely unguarded and honest, although there is also a troubling anonymity to it. Like it's REAL and WRONG.

Positioned on her bed in the semi-darkness, with the shades pulled down, and her legs spread wide and the laptop to her side, the scene makes its point and speaks to her fantasies - however complicated they are. Oftentimes she massages her tits and tweaks a nipple. Her vibrator does the rest.

She completes her solo stress relief for longer periods of time and even more often on lonely weekends, which is kind of depressing, but then she also doesn't want to be a fetish or a conquest for some weirdo-aficionado of huge breasted women. Those guys are very much out there! On her Match.com profile, she decides to add a picture of herself scooting down a zipline in Costa Rica...from five years ago. Because it's "fun."

She is stress relieving at 3:15 pm on a Saturday afternoon for 90 minutes, but you'd never know it when you trade messages with her. She wants to believe (and for you to believe) that she likes men with ordinary jobs and sensible haircuts above all else.

Aside from her various nondescript photos, there's also a treacly sunset picture, but then a picture of her plump and surprisingly sexy legs as she stretches out on her condo's balcony.

No man who bothers to actually read her words or who looks at her pictures completely understands something: That her efforts at dating are -- in fact - a mess of opposing forces and unhappy compromises.

Your Deal:

She hasn't guessed that you have your own agenda, because at this stage in your life, you're not entirely a sex fiend either: You can tell a good story, although you don't talk particularly much. You dress with some style. You have a garage, and in it an old Saab that you're trying to get back on the road, which means -- she says -- you're living a well-balanced life. That's good to know!

She is unaware that you certainly noticed the way her pictures provide a half-hint of the incredible middle-aged peaks on her chest.

In truth, you actually really don't like board games. You had to type 'Anne Bolyne' into Google. Your computer's search history, in fact, would tell her far too much about why you dropped her a note in the first place. The only thing that even made you interested in that zipline picture (or her profile at all) was the apparent enormities underneath that T-shirt. You discovered her mounds among thousands.

You are a breast-stalker, clearly.

You assume she must get dozens of messages each hour based on that picture alone, but that's actually not the case. You keep on returning to that five-year old picture: she's leaning back, while the contraption carries her down through the tropical rainforest. Her T-shirt is stretched and forced into extreme shapes to cover those female mountains; they are two outrages against ordinary expectations.

Holy hell. Is she for real? Is the camera lying? You magnify to 250%.

On the day you write her and say "Wanna grab a drink?" you happen to be the only man she's even considering meeting. You answered her question - What are you looking for? - appropriately. You want a relationship! (Liar)

One truth is this: Women approaching their fifties, with rather plain-plump faces and a checkmark next to the word 'BBW' and the words 'no time for games,' simply do NOT receive many messages. It's like the humor has been drained away - life and perceptions can be a little bit cruel that way.

Things Start to Develop:

At the end of the first date, it's dark. You've had a couple of drinks and when you walk her to her car you two hold hands. She's a little friendly.

However, she is still talking. She talks a lot. This reminds you of an old saying: 'The biggest bore is the person who keeps talking. And then continues to talk AFTER they've made their point.' That might describe her.

You wonder if this continual chatting is just nervous behavior. Then you find an opportunity and kiss her and it's pretty wonderful; you breathe in that close air and hug that body. This -- you think -- is surprisingly nice. Your hands find her sides. Okay, she's fat. That sweater / camouflage from Ross isn't working. But then those coast-to-coast tits smoosh into you, and there's instant lust. Unbelievable. They must weigh -- what? You have no point of understanding; she can certainly feel your passion but not the true nature of it.

You wonder about her nipples. There were hints of them before during that famous twist and waive for the waitstaff and then a few times later. Okay, think about that: Her nipples were suggested, even covered with a bra and a sweater.

Unbelievable. It takes all of your willpower to keep your hands planted on her sides and NOT grope those mammoth jutting fantasies - this as your mouth moves towards her neck. This becomes a secondary kiss near her ear, and it is so much more sexual than you intended.

She unexpectedly gives a little sigh. That alone gives you hope that there's a secret side to the woman you're now obsessed with.

No time for games? Perhaps you should confess your interest in her? Perhaps she can sense your ridiculous instant-on and enormous erection just next to her. You'll do anything to have breasts like hers in your life, including pretending to be a gentleman for weeks on end, and so you withdraw and act as reasonable as possible. Smart move. Relationship stuff is all you care about, right?

An hour later you text her: I had a great time! You're so much fun.

Still, you're thinking: Udders. Holy hell.

Also: There is no doubt. She clearly realizes the secret is out. They're HUGE, and you know it. Remember: She half-smiled and then full-smiled. Especially her nipples, which were suggested in ways that seemed impossible, are filling you with insane lust for their size. Maybe they are like the fat caps to a felt-tip pen. The truth is this: You've seen the push of her breasts and felt them smoosh into you during that too long hug.

Whatever you do next...keep silent. DON'T ASK: "What bra size do you wear?"

Distance-Dating on the Phone:

One week later you're telling her about this automotive discovery on Hemmings.com.

You've apparently found a barely running '74 Jaguar sedan located out in San Diego. This dubious item is located at a car dealership, and you've been curious for weeks now (you are such a liar), and it's just waiting for an adoring owner, and you want to see it in person!

So...the point is this: Maybe you could be her date for her sister's wedding after all?

Before you can imagine it, you are suddenly her Plus One and she'll pick you up at San Diego's airport on Friday at 8:30 pm. With all the hurry and supposed spontaneity of the situation, neither of you talks about hotel rooms, the fact of which only occurs to you after you're off the phone.

Congratulations! Thanks to your mostly reasonable life and good table manners you clearly are suitable to meet her family, and therefore rated an invite. She wants a mature / reasonable man, right? You can be that. Stable. That's your middle name. "Relationship" is all you care about. Never forget.

You tell yourself: Do NOT mention the hotel room situation until the absolute last minute (when it's too late to do anything about it) - and you hope she'll somehow accept the inevitability of you two together in a bed.

Still, it's like a weird version of high school with her. She's not talking unless she's complaining about something. You're starting to grasp her tortured psychology: She's trapped by emotional problems of a certain variety. Namely some sort of inferiority complex.

She hates the bridesmaid dress that she is "forced" to wear, of course.

It's a cliché, but she won't stop talking about it. Yes. The color is like a prom dress from 1985. Yes. The material is cheap and feels it. What else is new? She thinks the dress was intentionally chosen to humiliate her. She's going to look AWFUL. "The color makes my skin look weird."

The phone call covers the topic from all conceivable angles, and you're exhausted by her mania, and then suddenly she says: "You're a good listener. Thanks."

She meanders around for a little while and then says: "My sister drives me crazy, sometimes. (There is a pause.) You know what? The fact that you're going to be here tomorrow with me...? It's kinda' making me more excited than I want to admit."

Der Kaiserhof:

When she picks you up in the passenger arrivals area, she's in a rental car and dressed for the bridal party "event," which is currently ongoing in a separate not-big-enough room at some German restaurant.

Who selects a German restaurant for something like a bridal party "event"?!? And in Sand Diego, which seems like an especially odd combination. She rolls her eyes, but all you notice is the dress she's wearing. It's like an anti-bridesmaid dress; it looks expensive and is certainly flattering, but then there is her excessive makeup. Also, her over-styled hair, which appears like it must be crunchy to touch. Before she was bland, now she's Extra Glamour Girl.

Earlier: What was she saying about avoiding 1985? She is -- in fact -- right there in spirit.

Still: Holy hell. Her plump arms are exposed but easily overwhelmed by her profile even sitting there behind the wheel. She's dropped the frump-look disguise and embraced her curves for the night. "Nice suit," she says, a little relived you decided to dress up like her, even before the wedding. "It looks great on you." For once, she is voicing something other than a complaint.

You sit there and look out through the windshield, trying to figure out if you should kiss her.

Even people who are walking by and standing around bored (while waiting for their ride home) seem both attractive and cosmopolitan in this part of the world. Hey, there goes an old Bentley! Cool. They are fit, wealthy, and stylish in San Diego.