This is Your Wake-up Call (Or, the Story of the Disappointing Penis)

Waking up disoriented in a strange hotel room sounds like the beginnings of an urban legend.  Maybe it was because I hadn’t had all that much to drink the night before OR maybe because my dog was there beside me OR maybe because my host had left hours earlier—but I did not find WELCOME TO AIDS scrawled in lipstick on the bathroom mirror or a stranger soaking in an ice-filled bathtub with a recently removed kidney.

I did find a few spent condoms in the trash.

I also found my panties and dress mixed up in the sheets.

As I made my way across the room filled with dirty clothes, generic whiskey bottles, and half-empty pizza boxes, I became acutely aware of the fact that I was ankle deep in self-loathing.  My worn-out, haggard expression staring back at me in the mirror only confirmed the pieces of memory floating back into my consciousness.

I had been on a date when I saw Big Boy standing in the corner.  We were in a country-western bar mimicking a night club on Ladies Night—and so I got in free and drank for free.  Twenty years ago this would have meant that I got trashed, threw up, blacked out, and ended up wherever with whomever.  Now that I’m a grown-up, this means that I pay my date’s cover, sip one beer, find myself nearly invisible, and end up in a shitty hotel room with a guy other than my date.

ME: (standing on my tiptoes so he can hear me) Come here often?

BIG BOY:  Did you really just use that line?

ME: Uh, sorry.  What’s your sign?

BIG BOY:  Aren’t you on a date?  I noticed you holding hands with some black dude.

ME:  I met him on Craigslist.  It’s only kind of a date.  He likes Cougars.

Big Boy was fascinated with the whole Craigslist pseudo-cougar-date scenario, and we fell into a rather awkward conversation with me standing up on my tiptoes each time one of us spoke.  My date scowled with displeasure when he saw me, but I still drove him home.

I was in bed when I got the text from Big Boy inviting me back out again: Calling it a night already . . .  I thought you were young at heart. LOL.  It’s still early.  Half of me really needed the sleep.  I had been out with Bad Boy Abercrombie the night before and didn’t get home until after 2 o’clock in the morning.  It had been a surreal evening with me having my wish to see him come true and shattered all at once.  Now I had a chance to meet up with Big Boy and go after that orgasm that had eluded me only 24 hours ago.

BIG BOY:  The night’s not over.  You can make the best of a bad situation.  Surely better than company with your dog.

ME:  What do you propose?

BIG BOY:  My proposal is that you come finish the night with a bang and have some fun with me.

We are both more than a little surprised when I show up in heels and a dress an hour later.  We meet on the street because the bars are emptying out after last call.  Big Boy’s friend is standing there with him.  They are not hungry but agree to go to a diner with me so I can eat.  We all order smothered breakfast burritos the size of a newborn baby.

Big Boy’s friend takes their truck, and I drive Big Boy back to his hotel room.  We are awkwardly clumsy with where this is all headed but he’s funny and has a nice smile, so I’m moderately comfortable.  Then he begins to kiss me and all bets are off.  I hate kissing him.  His tongue is weird and slurpy and there’s way too much saliva.  At least he’s going to have a huge cock, I think to myself knowing from experience that a man of his stature is typically well-endowed.

As he goes down on me, I fantasize about how we met but change things up a bit.  We’re in a bathroom stall.  I’m blowing him.  Another guy comes in and begins to fuck me . . . . Then I cum all over Big Boy’s face and I nearly pass out.  He doesn’t realize that I really need him to stop, so I flip around a bit and start playing with him.

The man has a small penis.  It’s short and narrow.  It’s not what I had in mind at all.

We fumble around, I try and kiss him again, and finally he slips a condom on and tries to enter me.  Now he’s limp and small and narrow and I’m not having any of it.  I squirm away, murmur something that I hope is pleasant, and proceed to wrap myself in his big, manly arms.

The cuddling is definitely the highlight of the evening for me.  I can get lost in a man this size.  And even though it’s a super-casual-one-night-stand, he’s practically purring into my hair as he strokes it.

Three hours later he’s gone to work and I’m peering into the bathroom mirror wishing I was the kind of girl who could do this all of the time because I didn’t have to be at work at the crack of dawn or the kind of girl who didn’t sleep with strangers.  I am neither.


  1. Hmmmm…you sound like a female version of me

    1. I will have to check you out! Thanks for the comments.

  2. […] at maneuvering the Craigslist labyrinth, and I also feel more comfortable at sex clubs. Casual sex with strangers seems to be my forte. What can I say? We all have our […]

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