She's the Boss.

My name is Ken. I work smackdab in downtown Boston. And I totally want to have sex with my boss. Good morning.

My boss is about 56 years old. Blonde, roughly 5'3". Prolly 100 pounds soaking wet and holding a sack of potatoes. She is a mother of four from one of the city's affluent suburbs. And, holy mother of god, I want to bury my face between her legs with an intensity that only guys who've been in prison for twenty years can appreciate.

Why do I wanna bone a woman who is roughly ten years younger than my mother? Because she's my boss. Sure, she's also an incredibly hot 56-year-old professional who has her hair done on Newbury Street and depends on a team of twenty five Vietnamese women in Newton to keep her nails appropriately chiseled. But, dude, fucking the boss? That's gotta be bonus points the likes of which my feeble mind could never comprehend.

It's also never going to happen. Because she's the boss. And she didn't get to be the boss by throwing herself at goofy, pale, nerdy subordinates.

Not that there isn't something there. We've been on countless business trips together, during which jokes about sex and making out and getting fingered fly fast and furious [that last one being a story she told me about her high school prom that had me up all night in my hotel room jerking off to the dulcet tones of CNN]. Once, while we were setting up our company's booth at a trade show, she bent over and inadvertently backed up squarely against my crotch, then stood there for a beat, noting, "Hey, I hope you at least buy me dinner after this." And, voila, I had enough masturbatory fuel for, oh, ten months.

But, again, I can fantasize all I want; I ain't gettin' in the boss' three-hundred dollar pants. Although I would like to assure her that letting me bone her in the Executive Conference Room wouldn't shift the balance of power. In fact, it would probably make me an even better employee, as I see it.

Perhaps, in the dark recesses of her mind, she's thought of this as well. And is even considering throwing me a bang before her retirement. In any event, I'll be here, waiting for the Boss to come to her senses and swoop me up in her streamlined Mercedes for a night of passionate snogging and backseat screwing.

In the meantime, I may try my luck with the 62-year old Haitian cleaning woman. I see the way she looks at me...

Guest Post: I Still Got It

As you may or may not have noticed, the lovely Ginger has been absent from these pages for some time now, as she pursues other ventures. For fear that this blog may start bursting at the seams from all the testosterone I'm pumping into it, I reached out to the lovely Skye at Met Another Frog, who helped me recruit a dazzling array of fine female bloggers who have agreed to contribute some guest posts, provided I cease and desist with my constant begging for them to sit on my face. With that, I give you the first of these guest posts, from Lucky Girl of the blog How Very Lucky:

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There’d been too much disappointment. Heartbreak. And far too many 60-something comb-overs wearing mom-jeans trying to enter my digital domicile in the online mating marketplace.

No, sir. You do not look young. You look exactly your age. Maybe even older. The fact that your ex-wife and last girlfriend were both 30 years your junior doesn’t at all make you more marketable in my eyes. It makes you creepy.

When I find it rising in me, that cynicism, like a pot of rolling milk, rising, erupting into to an overflowing boil, it’s time to remove the pot from the stove. I needed a break. To reconnect with myself, to restore my faith and optimism. To remember that I am not a magnet for losers. But that the interweb sometimes is. Right?

So began my dating vacation.

My allergies were bad that Friday. I decided, impulsively and impetuously as I am wont to do, that a major spring cleaning was the solution. I put on the 30-something girl’s equivalent to my grandmother’s housedress. Minus the dress part. The point is, it wasn’t meant to be seen by anything other than the tile floor I was scrubbing.

But then I decided to wash the rugs and curtains. At the laundromat.

I walked out of my apartment. An unkempt, caramel-skinned man stood on the corner, singing. I smiled. He shifted to Sam Cooke’s “Cupid”, and followed me on my journey to the laundromat. I felt like the Pied Piper.

It was a moment that I should have appreciated. Normally would have appreciated. But instead I was annoyed. Who follows a girl that looks like she should be cleaning your toilet singing “Cupid”? Apparently, this guy does.

I quickened my gait and turned the corner nearing the laundromat. But not before a man sitting on a stoop, smoking a cigarette and talking to his friend stopped me.

"Excuse me. Miss?"

Ugh. What does he want?

He rose. What I’d hoped to be “Can you tell me the time?” or “Do you know how to get to _____” turned out the be this man’s poor attempt at a pick-up.

"So. Um. Yeah. Um."

He was a close talker.

"Yeah. Um. I just wanna talk to you. You know? Um. Yeah. Do you have a quarter?"

Wow. I’m standing there holding a huge bottle of Tide, two rather large and heavy rugs wrapped in a pair of brown silk dupioni curtains (which, incidentally and much to my dismay, later proved their dry cleaning tags correct), and a couple rolls of quarters in plain site. This sucked. But giving him one would be easier than saying no.

I couldn’t quite see over the heaping pile of laundry in my arms, but managed to free a quarter from the roll and hand it to him. And that’s when I saw it. He was holding his penis in his hands, smiling.

"You know what? A simple thank you woulda done it."

Unbelievable. In broad daylight! Jesus.

I duck into the laundromat. I drop the motherload in my arms onto the floor with relief and proceed to pack the rugs and curtains into three super-sized machines, plugging each of them full of the 22-quarters they required. I added detergent and grabbed the small bag I’d brought along. There were three empty seats along the east wall. I chose the middle seat. I reached into my bag, placed a ball of yarn on the seat next to me and started to knit. Yeah, so I’m that lady now. Single. No prospects. Proud cat owner. Proud cat owner who knits.

I know what you’re thinking. Prize. Clearly.

Anyway, I’m minding my own business when a man walks in. There are other seats surrounding the laundromat. All of which are empty. But he has to have the one next to me. The one with my knitting supplies. Damn it.

I begrudgingly move them and slide down to the next chair.

"Excuse me. Miss?"

Jesus, really? Can’t a girl just do her laundry and knit in peace? Did I really just think that? God. I did. This is why I’m on vacation.

I look at him. With attitude.

"Yes?"

"I just want to talk to you. You’re a really beautiful woman."

Oh god. I ignore him. Slip. Slip. Knit. Yarn Over.

"Miss? I said you look beautiful."

Seriously? Pony-tailed, no make-up, dirty yoga pants and a gray t-shirt with a stain looks beautiful? Well, I did get a serenade and a strip tease...

"Thank you."

He goes on. I’m trying to count. I’ve already fucked up this baby blanket three times and had to start over.

I look at him. I look annoyed.

"Please. Just stop…"

But before I can finish, two cops enter. My wishful boyfriend jumps up. He walks coolly around the folding table to the other side of the room, clutching a large gym bag. The officers approach slowly, taking position on opposite sides of the folding table. My laundromat libertine is cornered. He pauses for a moment and then takes off in a tornado, running full-speed into a woman in his path who is slowly sorting whites from colors. She wobbles like a Weeble but thankfully is left standing, terrified and stunned. The cops sway side to side like linemen ready for a tackle. One goes for the bag, the other for him. The Don Juan of Detergent gets away. They get the bag.

I return to my knitting. I guess I can add petty thief to today’s list of Lotharios.

So in summary. I still got it. I don’t need the interwebs. I can attract losers everywhere.

Sometimes You Just Have to Come Right Out and Ask Them

In my never-ending quest to convince women to sit on my face, I've employed many tactics: buying dinner and drinks, laying on the compliments, bragging about how I've spent most of my adult life hunting the killer whale that devoured my uncle. And so on.

Never, ever had it occurred to me to walk up to 'em in a public square, lie down on the concrete, and simply ask 'em, point blank, to use my mug like a sofa.

But that's exactly what this guy did:



I can't imagine the guy didn't get his ass whipped at some point during the proceedings. But the fact that he somehow talked two rather attractive and well-arsed lasses into sitting on his face instantly makes him my write-in candidate for mayor.

Open Letter to Myself: Please Don't Go Drinking With the Crazy Girls from the Office

Dear Ken: Next week, you will be representing your company at "the conference." While you are at "the conference," you will be in the company of several coworkers, all of them female, between the ages of 23 and 46. These girls, as you well know, like to drink. Often to excess. This note is to remind you that no matter how much you want to, you should not go drinking with the crazy girls from the office.

Part of the reason is that you know how you get. A coupla beers and suddenly you're going on and on about how you've mastered the art of eating pussy. How you gently suck the clit and hold it between your lips, appying gradual pressure while briskly racing your tongue across it. These are not the sort of things you should be saying to women you work with. So please, don't go drinking with the crazy girls from the office.

Also, you know they like to dance. Remember that night they pulled you onto the floor with them at the Hong Kong? If you go drinking with them, you'll invariably end up dancing with them. Which means Loretta from Customer Service will sashay up to you and arch her not entirely bad ass at you, inviting you to start dry humping it to the dulcimer tones of "Paradise by the Dashboard Light." And you'll do it, because you're drunk and, well, it's a female ass. And, because you're a heterosexual dude, you'll begin to stiffen. And suddenly Loretta from Customer Service is giving you a hard-on. And that's not what you want to happen, dude. It just isn't. So please, don't go drinking with the crazy girls from the office.

Remember, also, that these girls never know when to quit. And because, as Tom Waits once sang, "the night does funny things inside a man," you'll invite them all up to your room after last call. Because you've got "the big room." The Executive Special that comes with a big-ass conference table and a wet bar. And you'll imagine them all fighting over who gets to blow you first, but they're really just coming to drain your minibar. And the closest you come to naked flesh is when Janet inexplicably pulls you into the bathroom with her, locks the door, and forces you into the shower and closes the curtain so she can take a whiz. When you come back out, you see Frances polishing off a bottle of champagne which, according to the Hyatt mini-bar pricelist, just cost you sixty dollars. You don't need to be explaining such expenses to your boss, so please, don't go drinking with the crazy girls from the office.

Dude. Seriously. Do you really want Loretta telling people that she gave you a hard-on? Just don't even give it a chance to happen. Don't get yourself into such situations. There's probably a good movie on. Hell, get a porno and spank it till the wheels fall off. But don't go drinking with the crazy girls from the office. There's just nothing good that can come of it.

Note: The conference was actually last week. And, yeah, I went drinking with the crazy girls from the office.

Homeless, Yes. But Well-Laid.

So last Friday, me and my man Sully were taking lunch at a bar near Kenmore Square. And there's this skeevy looking dude sitting all by himself at a corner table. A dude who seriously looked like a bona fide homeless fella, with a tattered Herald under his arm, one of those hand-held transistor radios they stopped making back in the Carter administration, and hair like he'd just brushed it with a pillow. Sully and I started wondering aloud how long it would be until a waitress or bouncer kicked him out.

About four beers later, this cute, professional-looking woman walks in: long brown hair, tight skirt, smokin' hot ass. And as Sully and I suck in our chests and start involuntarily flexing our biceps, she passes us and beelines for the hobo. Gives him a kiss on the cheek. Runs her hand through his impossibly scroungy hair. And I'm thinking this has gotta be a joke, A B.U. sorority chick "let's tease the homeless dude" thing. But as they're talking, he places his unkempt hand on the spectacular curve of her derriere. And it stays there. Until she kisses him again and joins him in the booth.

So Sully and I start doing the math. A hand on her ass. Kisses on the mouth. It's not her dad [and if it was... ewwwww]. Not a brother. Might be a cousin, but... who the fuck feels up their cousin's ass? No, we figured. These two must be romantically involved. And as they sat there, her perfume covering the dirt fumes rising off his scalp, you could see that she was actually enjoying his company. Christ almighty, she was there by choice!

And it gets us thinking... how do guys like that [and you see the photo above, folks? Not that far off.] score premium trim like her? It's the one thing that always blows my mind when I see a guy who by all accounts is either destitute or filthy with some hygiene-related disease or barking madly at a wall in a Heineken-inspired haze and he's got a fucking hottie on his arm.

What is it, ladies? Do these scumbags have money? Huge cocks? Real estate in Miami? Or is it a sympathy thing? Because I'm ready to give up on the whole showering bit if it lands my mouth between your legs with greater frequency.

Oral in the Car. And Why Not?

The blowjob in the car is one of those things that is awesome simply in and of itself. Slightly cooler than the blowjob in the hammock but a little less fantastic that the blowjob in the space shuttle, the car smoothie is intensified by the fact that it adds a precise element of danger to the proceedings.

As the driver of the car, I know I have to keep my focus on the road. Because, man, there's big-ass trucks and crazy seventeen year old girls trying to simultaneously text their BFFs and steer a Lincoln Navigator across six lanes of highway out there. But as the recipient of the blowjob, I also know that the lifeblood which is so necessary to keeping my brainwaves nice and snappy is being filtered away to my lower extremities, giving me that slightly dizzy, slightly buzzed, holy-shit-I'm-getting-a-beaner-in-the-car feeling that truly dulls the reaction times.

Also, if it's a particularly long drive, and said blowjob is helpful in keeping me from slipping off into a narcoleptic coma on interstate 95, then I certainly want to prolong the sensation and retain my seed for as long as possible (which for me, ladies, ain't all that long). But that increases the risk of being discovered by a fellow driver who might snap a quick vid of the proceedings and throw it up on YouTube.

Worst of all, as a guy who just hasn't mastered the art of post-orgasm smalltalk, I find myself in a precarious situation once the BJ has officially ended and I realize I've still got 65 miles to Boston. Once, after a Kennette obliged me in the car, I simply nodded, smiled, said, "Woah" and "Awesome" and then proceeded to mess with the radio buttons for the next twenty minutes.

I Still Don't Understand Women

So the other night I meet a female pal of mine for dinner. As we sift through the appetizers, she tells me how her lovelife's been pretty lame of late, and with each successive glass of booze, she gets a bit more descriptive as to what it is that's got her bummed. Apparently, the last few guys she's dated haven't gone down on her, and she's absolutely "dying" -- her words -- for a bit of tongue-lashing.

This being a long-time pal of mine, and quite a hot little number to boot, I assure her that those guys must be crazy or perhaps even a bit queer to not want to work her over, and that everything will likely change with the next boyfriend.

And she starts to explain how she just needs to be sucked on so badly that she's just looking for someone -- anyone -- who'll go down on her with no strings attached. Just so she can remind herself of what it feels like.

And I tell her again that the next man who comes into her life will probably be the guy for the job. I also add that if all she really wants is a little downtown action, I'm sure any guy in any bar in any part of the country -- provided, y'know, he swung that way -- would be more than up to the task.

And she says, no, she doesn't have the time to filter out the psychos and sissy-boys and Dave Matthews fans. She needs someone she can trust. Someone who'll just do the job like it needs to be done. As she puts it, she literally just wants to lay down, get eaten like there's no goddam tomorrow, and put this cursed drought behind her.

So I, fueled purely by alcohol and a prolonged look at her derriere when she got up to use the ladies room, lamely offer my services, seeing as how she almost seems to be steering the conversation in that direction. Hell, I'm always down to go down, as the Cub Scout Mantra dictates.

And that's when she quickly changes direction. "Oh god, no," she says. "We couldn't do that."

But at least I offered. And perhaps that all she wanted to hear.