The Nerdy Guy

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After things fizzled out with Blueberry Pie Guy, Chicago moved into its cold hearted winter where not much dating happened. It’s almost destined to be a terrible first impression when you have to show up basically covered from head to toe with hat, scarf, gloves, giant puffy jacket, and boots. Chances are you’d be hard pressed to know if your date even showed up until they had undressed themselves from all their winter weather gear and then cross your fingers, hope that they look something like their profile picture. But as winter wore off and spring bloomed, I met Steve. Steve was a skinny, nerdy guy. (I’m not sure what it is about me, but I do tend to attract the nerdy types.) We met up for burgers at a local restaurant and bar and hit it off pretty decently. We shared some laughs and enough common interests that the conversation didn’t run dry too quickly. We continued to see each other, and yes, he even made it past the three date rule. However, as things progressed, and we began to get further into the relationship, we hit a little bump in the road. Here’s a little rundown of how things went.

Couch Make-Out

By about our third date, I had become comfortable enough with Steve to invite him over to my place. Another benefit of the three date rule is that if you are liking the guy enough by then, it’s a great time to invite him over and start getting a bit more comfortable. It was a rainy day in Chicago so we ordered a pizza and cuddled up on my tiny futon/couch to watch a movie. Before long that cuddling turned to kissing, and a full-on make-out session was underway. So much for whatever movie we were watching. Things were certainly getting a bit hot and heavy, but I was able to maintain a bit of restraint. We managed to keep all of our clothes on, but there was definitely a good buzzing feeling going on by the end of this date.


As things quickly transpired during our next date to ending up in my bed, is it even believable that not so long ago my sexual experience with men was so minimal I’d barely even seen a guy naked? Much less been comfortable rolling around between the sheets with a guy I still barely knew. Progress, my friends.

Well, Steve had quite a lot of confidence in his kissing, and his sexy talk was also quite advanced for a nerdy, awkward guy. His kissing technique was good. Soft and sweet with the right amount of tongue. He was also quite adept with his hands, able to get a good reaction with just the right amount of pressure.

At this point, the anticipation is getting pretty high and things start moving quickly as clothes start flying and getting strewn about. I didn’t really get a lot of time to check out the goods before protection was secured and we were ready for lift off into sexual bliss. Sadly, this rocket was no Space X. There were no ohhhs and ahhhhs of wonder. As Steve began rocking in and out of me, I could barely feel a thing. This was like the tiny, plastic version of the toy you really wanted. What a time to realize that size does actually matter. Was his dick unusually small, or had my previous conquests just been well endowed? Sadly for Steve, he just wasn’t as blessed in that department. Eventually I finished with a little helping hand, but the overall effect of the experience left a lot to be desired.

Beach Picnic

Photo by Hannah Nelson on

Not wanting to write Steve off from one unsatisfactory experience, we continued to chat and see each other. Maybe if we kept at it, we could figure out how to create a more fulfilling experience?

On our next date, we decided to have a cute picnic on the beach. The weather was just starting to warm and how lovely would it be to watch the sunset on the beach while we cuddled together. We both promised to bring snacks to share. Steve was especially excited about this cheese that he said was just Ahhh-mazing. At the time, I wasn’t really a huge cheese fan unless it was melted on my sandwich or pizza. The thought of eating a cube of cheese kind of made me want to gag. (Don’t worry, my views on cheese have changed a lot over the years. I now enjoy a good cheese and cracker snack with delight.) But ever the optimist, Steve was just so pumped to bring it and have me try it.

We arrive at the beach which was relatively uncrowded and set up our blankets a bit away from a small group of people playing frisbee and badminton. We begin unwrapping our snacks and digging in when Steve pulls out the mystery cheese. It turns out to be a tub of what basically looks like glorified cheese whiz. It’s only saving grace being that you don’t have to squeeze it out of a can. I choke a little down with a cracker. I’m about as enamored by the Ahhh-mazing cheese as I was by our ahhh-mazing experience in bed the other night.

Not looking to ruin the evening though, I leave Steve to his cheese and stick to our other selections of fruits and crackers. We make light conversation and share sweet kisses when suddenly Steve’s hands begin moving south and finding their way to some very private areas. I blush and nervously look around, but no one else is really paying us any attention. I allow him to continue his rubbing and stroking. It’s really his best asset and the closest I’ve come to sex on the beach.

Feeling somewhat satisfied as we watch the sun set, Steve leans over and whispers in my ear,

“I can’t wait to be with you again. I want to take you while holding you up against the wall.”

Woah there, cowboy! Although our last encounter was nothing to write home about, this has definitely caught my attention. Maybe a change of position will lead to better results? Probably not. But a girl can hope, right?

With my body buzzing, I suggest we pack up this picnic and get back to my place real quick. Or at least as quick as an ambling CTA bus will get us there. Just more time to allow the anticipation to simmer, I suppose. We giddly make it to my apartment and quickly go through some frantic kissing, losing clothes and suddenly the moment is here. As he picks me up, and I wrap my legs around him, he slips himself inside me. I close my eyes and imagine how this scene might play out in the movies, but then things quickly go from sexy romance movie to wobbly jello legs. Truly a whole 30 seconds and he’s already tired? This is so not the sexy fantasy I had in mind.

We return to a more traditional missionary position before anyone gets dropped or collapses from effort. I try to get back into it, but the magic’s just gone. I give a few fake groans and clenches and pretend I’ve come just to end this sad experiment. Special note to dudes out there. Don’t make promises about advanced sexual positions if you aren’t able to hold up your end of the deal. Also, why did I think this scrawny guy’s muscles were going to be up to the task? I may be “tiny”, but under all that tiny there’s some pretty solid muscle. You’d think this would have put an end to the evening. Some guys might have their pride hurt a bit at not being able to deliver on their promises. But no, not for Mr. Optimistic Steve.

Not to be deterred after this minor blip, Steve and I remain semi-cuddled in bed. In my head I’m already trying to figure out how to let the guy down easy without hurting his feelings. But Steve has other ideas, and he asks about staying the night.

“After all, every girl loves morning sex,” he says. “I bet you love having sex in the morning.”

Ugh! I politely suggest that it’s a little early on in our relationship for a sleep over. He’s a bit right of course- there’s definitely something special about good morning sex, but no Steve, no I don’t want to have sex with you in the morning, or really ever again.

After that night, Steve and I didn’t see each other again. I hope he found himself a good match at some point. To this day he’s still the most itsy bitsy teenie weenie I’ve ever seenie.

Until Next Time,


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