So I hooked up with Alex the other night. I was supposed to meet up with someone else, but logistical problems stymied us. Since I was in a horny state of mind (and wearing my new purple thong), I decided to check-in on Alex who'd sent me a text earlier that day asking, “do you want some ice cream?”. I thought this was rather sweet until I realized he was making some sort of man-cream reference. I think.

Alex is pretty much my only “cute meet”. A couple summers ago I was out of town for several weeks. Alex and I 'liked' each other on OkCupid. We flirted on and off for awhile but things sort of fizzled out due to the physical distance between us. Flash forward a few weeks. I was back in town, had gone out dancing one night and on my way home I remembered I was supposed to pick up some Dayquil for my mom. After learning my go-to Walgreens was no longer 24 hours, I drove a few miles to the next closest drugstore. I bought the Dayquil, got back in the car and was just about to turn on the ignition when I noticed someone approaching in my peripheral vision. In the three seconds it took for him to reach me, I'd already morphed into 2am-matter-of-fact-don't-fuck-with-me mode.

“Excuse me?”, says a male voice.

“Yeah.” I reply with a sidelong glance and a non-encouraging manner.

“Aren't you Kitty?”

I take a good look at him for the first time and think to myself, no way would I have forgotten a guy this cute.

“Do you know who I am?”, he asks.


“It's Alex from OkCupid.”

Omg. Right. Alex from OkCupid. What are the odds of running into an OKC match at 2am at a non-usual drugstore AND he recognizes me from my pics (and still decides to strike up a conversation).

I get out of the car and we chitchat for a bit. He's a cute Brazilian who drives for Uber, also does massage (ka-ching), and has his own place nearby. Say no more. He seems mildly surprised that I'm so amenable to going home with him but that's just how I roll. I can be rather shy and awkward unless there's a bed in the room, metaphorically speaking.

The encounter was nice. He busted out the massage table, the sex was good, but there was a certain lack of chemistry between us. Our second encounter wasn't great. His enthusiasm level was not where I would've liked it to be. He seemed happy to let me blow him; didn't seem anxious to fuck me. So the next few times he hit me up, I brushed him off or simply didn't reply to his texts. I figured he'd get the message. I have to give him persistence points. He shot me a message every few months (which I ignored). I was kind of surprised he bothered. I figured it was either that he was super horny or that I was super easy or some combination of both. It never occurred to me that he might be into me in particular. It still doesn't. I take it very personally when a guy doesn't fuck me when he clearly has the green light to do so.

A few weeks ago I received a kik message from a user I didn't recognize. Curiosity got the best of me and I sent a message back asking “who is this?”. Some polite chitchat ensued with the usual we-should-get-together-hmu sometime.... I doubt a hookup woulda happened, however, if I hadn't accidentally messaged Alex thinking he was someone else (those darn kik usernames), then liked his Ice Cream message, and finally, been disappointed by my semi-planned assignation.

So I ended up dropping in on Alex with the intention of a no-sex handjob. I told him I was abstaining from fucking for the time being. I really like to watch guys masturbate and he agreed to put on a show for me if I participated a bit for inspiration. I start by watching him stroke. He's bigger than I remember. Then I gave his jaunty balls a tongue bath. The next thing I know he's in my mouth. This is what usually happens when I attempt to watch. I can't help myself. It's there. It's hard. It wants my mouth. At some point Alex moves behind me to stroke my ass. His hand moves between my legs and he does a commendable job of locating then stroking my clit. I ask him if he has a condom.

“You want me to fuck you?”


I grab a condom from my purse and watch as he puts it on. He fucks me doggy-style and his size hurts a bit at first then we adjust and he does some impressive stroking with that cock. He asks if he can fuck my ass but I decline. He's just too damn big for anal.

As I'm writing this, he texts me, “so how tasty was that cum???” Lol. Should I be offended, cuz really I'm just amused... He tends to send somewhat piggish messages like “come eat it” with a nice video of him wanking. The messages seem to be sans misogynistic overtones (really!) so I let them slide. I take this opportunity to ask if he has problems coming if he's wearing a condom.

“Why do you ask?”

“Cuz you didn't cum while fucking me”.

“Sometimes I can, sometimes I need more stimulation. What are your thoughts on that?”

“I'd like to think that my pussy is stimulation enough, but I understand.”

I tend to get hung up if a guy doesn't cum to my expectations. I take it like he's not that into me/it. Or what am I not doing right. The only cardio I get is jumping to conclusions. Ha.

So he tells me he's going to sleep now but he's going to bust a nut first :) so I send him a naughty pic for his spank bank and tell him 'nighty night....