Not Sure What I Want Tonight
Story Codes: MF, Consensual, Exhibitionist,

Not Sure What I Want Tonight (w4m)
by Liz Doherty

Just looking at the menu tonight here on the list, and not sure what I want. Some
titillating phone chat? A drink at a local dive spot with a handsome stranger? A
scintillating guest to share this 420 and beer w/ me? I can't decide. Can I please see
a dessert menu?

Craig’s List really is a candy store of sorts, for a sexually motivated woman who
knows how to use it.  And I have quite the sweet tooth.  I was still learning when I
posted this one evening after work, at around 9. After a couple of emails and a short
phone call I was having a drink with Larry at a local dive.  It was 10:30, and I bought
the first round.  I’d invited him, right?

“I'd like to share smoke drink & whatever may come...Become friends and give you
the special attention you deserve! ...with a really nice, dominant man with brains,
good looks, and certainly knows how to treat a woman right!!  Fun in & out of the

Pretty generic stuff, but he went on to say he was in his late 30s, well endowed and
was also from back east, and he looked pretty good in the G-rated tuxedo photo he
sent.  I paused briefly to consider if he’d sent me a photo from his own wedding day,
but decided the corsage was too small for a groom.  He wouldn’t be that tacky, even
for Craig’s List, where men will say and do almost anything, on email anyway.

Larry’s corsage was small, but he’d said his business wasn’t.  I don’t always ask for a
large cock in my posts, but I try to only hook up with the well-endowed.  I guess that
makes me a ‘size queen’, an anatomical preference of mine that’s not meant to
belittle those with smaller packages.  I know what I like, and I’m not ashamed to admit
it.  I’ve heard of men who lie about their cock size, say they’re well-hung when they’
re not.  Do they think I won’t figure it out?  On Craig’s List, where people routinely
give all their ‘stats’ – age, race, height, weight, marital and STD status and cock size
- it can be a touchy thing, asking guys about the size of their dicks.  I guess because
there’s nothing they can do about it.  Unlike breasts, which women have options to
enhance and augment, a guy’s got whatever god and his genetics gave him.  You’d
think they’d be less sensitive about it for that reason, but I’ve offended some with my
polite requests for something big.  Several have been pretty hostile about it.  But I
know what my body wants and needs, and my Mr. Right, when I find him, will
definitely be packing a big one.

Larry was a little guy, no taller and not much heavier than I am, which is pretty slim.  I
could see that he was wiry and strong, and he sure didn’t look 38.  He looked like a
boy and it was working for me.  We drank our first round fairly quickly, sharing
benign stories about ourselves and a little about our adventures on Craig’s List.  I
had learned already that most men – even the playful hook-ups – don’t really want
to know the extent of my play on CL.  I imagine it activates their fear of not
measuring up to the competition, so to speak, but I can’t be sure.  I gave him my
standard, “Yes, I’ve met a few people from Craig’s List,” line, and left it at that.  I
sensed he wouldn’t have minded hearing more, but I mostly save my stories for

Halfway into our second drink, it was clear we were going back to my place, just
around the corner.  The smooth excuse:  that’s where the weed was.  I figured this
guy was a regular weed smoker.  He had the slightly spacey way of those who
indulge often, and he worked in restaurants, too, another sure sign.

We walked his bike back to my place two blocks away, and I put on a sexy mix CD as
he rolled us a joint.  We opened a couple of beers, took a hit or two, and then I
climbed on to his lap, straddling him, and took a taste.  Every now and then, I meet
someone who just tastes or smells ‘wrong’, but Larry wasn’t one of these.  His sweet
and beery breath was a good match for mine, and he was a great kisser.  Under the
sleeves of his T-shirt, I found the smooth, hard upper arm muscles I love.  His upper
back was also strong and taut, and the man had not a hair on him.  His skin was as
soft as a baby.  But the growing hardness in his jeans was decidedly adult.  I knew
he was a biker, and guessed his legs, when I got there, would be equally strong and
muscled.  It didn’t take long for us both to be pretty fucking warmed up

My dry cleaning budget was shot for the month, spent on beer and weed.  Not
wanting to leave expensive stains on my second-hand couch (yes, Craig’s List), I led
him to my bedroom, where I sat on the edge of the bed and watched him undress.  
This man was beautiful.  I walked around him a couple of times as I took off my own
clothes, running my hands over him.  “Are you sure you’re 38?  You’re in amazing
shape.”  He said he was sure, although maybe he’d smoked enough weed to have
lost track.

That soft skin, muscled thighs and calves, tight round ass… and oh, my, the
strangest shaped cock I’d ever met.  This one wasn’t just curled like a banana, it was
bent.  Really bent, in the middle, almost like it had been broken and hadn’t healed
properly.  Bent back towards his body, even fully erect.  He hadn’t lied when he said
it was big; it was, at least 8” or so, but still.  I sensed some looming geometric
problems, but wasn’t going to stop now.  He had me all worked up.

After a good half hour of kissing, licking, nibbling, pinching, twisting, tugging,
exploring, I laid him down on his back and prepared to have at him. My mother said I
never sucked my thumb or fingers as a baby.  Maybe if I had I wouldn’t be quite as
into sucking cock as I now am.  I positioned myself on my knees so his fingers could
reach me, and bent my neck at the peculiar angle needed to get his dick in my
mouth.  But for the life of me, I couldn’t keep it there.  It was like it had a life of its
own, and kept popping out of my mouth, heading back between his legs.  I needed
my hands to prop myself up for balance, but it was taking both of them to control this
thing.  It made sense at that point to just go straight to the fucking.

Well that was even worse.  I started on top of him, facing him, but couldn’t even pull
him in that way.  I spun around so I was straddling him and facing away, leaned
forward until my face was on the bed between his legs, still no luck.  We literally
couldn’t even get it in.  He was strong for a little guy, and picked me up and threw
me down on my back.  We got going that way for a few strokes at a time, in
missionary position, face to face with my right leg thrown over his left shoulder, but
he kept popping back out just when it seemed we got a rhythm going.  I was
beginning to lose my heat.

I held out for my favorite position, doggy style, not wanting that to fail, too, but I was
beginning to lose my focus.  As tasty and smooth as this guy was, I feared even this
might not work, but I sure wanted to try.  Pushing him off the bed, I placed myself at
the edge on my hands and knees, hips pushed high.  He stood behind me and
pressed hard into my lower back.  Luckily I’m still pretty flexible for a woman of my
age or he might have really hurt me.  We did a little better here, but he still kept
popping out every 10 or 12 strokes.  Just when I thought we had it, we’d lose it
again.  It didn’t help that I was so wet, and I considered going for a towel to try to dry
things off a bit, but knew that wouldn’t last long, not the way his other hand was
working my nipples and his mouth was licking my ears and neck.

Finally I pulled away.  “We have a geometry problem here.”  My guess is Larry was
out getting stoned during Geometry class, if he’d even gotten that far, and I’m not
sure he knew what I meant.  I turned to face him.  “This may not work.  I think we’
re…. shaped differently or something.”  He looked stunned – or stoned, it was hard
to tell which.  Now what?  “Let’s take a break,” I suggested.

He put his knit boxers back on, I pulled on a robe, and we went back to the living
room, where the beers and the rest of the joint waited on the little coffee table (yup,
Craig’s List, too).  I was definitely coming down.  Sure, we could have gotten each
other off with our hands.  Maybe I could have asked him to help me out with his
mouth, but that’s never really been my thing.  And quite frankly, I was a little sore,
which doesn’t happen to me often, but that dick had been pushing me in some pretty
peculiar directions, ones my body wasn’t used to.  I wonder if there’s a machine at
the gym that would help with that.

We smoked the rest of the joint, finished the beers, and made some small talk.  
“What now?”  It was probably close to 2 by then, and I didn’t know about him, but I
had to work in the morning and needed some sleep.   I was dying to ask him if he’d
had this problem before, whether his dick had always been bent like that, whether he’
d had trouble finding lovers who could accommodate it.  But I didn’t.  Instead I let him
pull my head down into his lap, where from the side, with my head on his legs, he
was able to find a way into my mouth until he came a few minutes later.  I, on the
other hand, hadn’t found the release I wanted, but was feeling more tired than horny
now.  We decided that he would go, which he did a few minutes later.   

Larry’s a sweet guy.  We’ve kept in touch.  We met again for drinks once, he’s been
over to smoke a joint a couple of times, and he even spent the night once when we
got so tired talking, drinking and smoking.  We tried sex one more time a few months
later, but same problem.  Kind of a shame, that.  He’s answered a couple more of my
posts, even two that I posted not on Casual Encounters but in the romance/dating
category of women seeking men.  We’re both looking for love – and sex -  and the
second is just not going to work for us, not that he’s my guy anyway.

What I learned from Larry:  Some 38-year-olds are still as smooth as little boys,
small guys can pack big packages, and there’s no fighting geometry when it comes
to fucking.   

©2008 by Liz Doherty

Liz Doherty is a writer and editor living in San Francisco, and a regular user of the Craigslist
personals.  She continues her on-line, sex-first search for her smoking hot Mr. Right with honesty
and humor, and still hopes he’s lurking there amid the acronyms, euphemisms and raunch.  She
can be reached through her website: