Have You Ever Fucked a Homeless Guy?

MH900442178Even though I do not work for The Man, I sure know how to put in the hours lately.  In fact, September 3rd (Labor Day in the States) was my first day off in five weeks.  No, I did not get off on my day off.

I sure as hell tried, though.

The morning starts innocently enough.  I meet my good friend, Platonic Guy, at his place and we go for a hike out in the wilderness where we can’t get into any real trouble, but my dog can sure get a shitload of burrs all over himself.

After that we scoped out a place to lunch.  For us, that means we sidled up to a bar to drink and nibble on some food.  Coming back from the bathroom, I notice the young man I’ve been drooling over for the last ten minutes–the one wearing camouflage shorts and a intsy, tintsy tank top–is standing beside my barstool.

ME:  It appears as though I should be sitting in your lap.

I say this while motioning that he is, indeed, hovering around my seat.

CAMO BOY:  That will cost you $10 or $20 if you want a photo.

ME:  How much extra without your shirt?

CAMO BOY:  All you gotta do is ask, pretty lady.

ME:  And the shorts?

I guess I go over the line, because he just smiles, laughs, and walks away. Platonic Guy leans over and whispers, “He’s never had that happen before, now has he?” and we both commiserate over the cynicism of youth these days over another beer/Bloody Mary.

We make it home alive and without a DUI, even though we clearly are running out of our drinking nine lives.  Once Platonic Guy and I get back, the clothes come off (in separate rooms), the bathing suits come on, the wine spritzers get poured, and it proceeds to rain.

Never to be one to let a little bad weather dampen my mood, I proceed to check out the Craigslist “Casual Encounter” Personals while Platonic Guy naps.  There I find:

  1. Lots of guys looking for “passable” T-girl sex.
  2. More MWM ads than I ever thought possible.
  3. Lots of guys interested in bigger women.
  4. More cockshots than even I can handle.
  5. One really cute model type wanting NSA anal sex with a woman.
  6. Two super cute guys who want to do it with one woman.

I respond to #5 & #6 and a bunch of others who probably wouldn’t typically make my initial cut, but I’m curious to see how they will respond to my panty pics (and I’m getting my period soon so there’s a deadline at hand).  Sadly, I don’t hear from the two guys right away, but I do make plans to meet Ass Man downtown.

I’ve never actually met a man I met on Craigslist before, so I’m more than a little nervous.  I’ve packed my Analyse and some condoms, but I’m still pretty much completely scared shitless.  What if he doesn’t find me attractive?  What if he’s a violent torturer and I get killed?  What . . . the hell am I doing?

Ass Man is sipping coffee at the bar when I arrive.  I never trust non-drinkers, so I’m a little put off by this.  As we begin chatting, I loosen up a bit—he’s a writer, a foot fetish Master, and does all sorts of non-mainstream entrepreneurial things.  He’s cute AND talks a lot AND is mildly fascinating AND tells me I am vanilla—so I am thrilled to be in his company.

Here’s the thing about being the kind of girl who answers Craigslist ads—you know you’re being a total slut, but it’s an easy way to get laid, and even though you both know why you are there (to go whoring), you don’t particularly want to be reminded of it.  Being called vanilla is a treat.

The thing about pleasant, interesting conversation is that it leads to more pleasant, interesting conversation, and this guy has a curfew.  No, he’s not married.  No, he hasn’t double booked on me.  No, it isn’t that he’d be coming down off of his high and needs his fix exactly at 9:00pm.  Nope.  He’s homeless and living in a Salvation Army shelter.  If he’s late, he’s locked out.

Well, he’s kind of homeless.

I don’t know how many of Ass Man’s stories to believe, or how many to flush through my bullshit crapper, so I’m not going to share them here.  All I can say is that I feel that the education I gained from this man is better than the anal sex could ever be.

That and he keeps making heroin jokes.  And there’s nothing scarier than the shit you can get from a heroin addict.

So we make plans for later in the week.

One Comment

  1. [...] him, and then I’m sorely disappointed because he’s really skinny, really hairy, really short, really homeless, or has a really small [...]

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