Nerdie: the City Adventure

Nerdie, which is my mash up of cutie and nerd, is my first true FWB - friends with benefits.

36, 5'10", 165 lbs, pale skin, light brown hair with the most adorable cowlick which makes a tiny bit of his hair stand up in the front. One front tooth that's at a a bit of an angle - also super cute! Thick, muscular thighs and healthy-sized butt. Not very hairy although some on his shoulders and back owing to his Italian side.

During my first week on Tinder, I accidentally Super Liked him. A Like would be a swipe right and a Super Like is a swipe north. I hit northeast spot on and it interpreted it as north. It happens to the best of us.

He wasn't very talkative over text and I almost thought he was going to ghost me for our first date. I have off on Mondays so I wrote him early in the day to try and confirm our date for that evening. He apologized for being too busy at work and said yes we were on. He lives in the next valley over - probably 20-30 miles as the crow flies - but an hour by car. We decided to meet in between.

He picked a very casual, down homey Italian restaurant in a strip mall. When I arrived, he was already seated. I noticed a high ball with a Coke can sitting next to it. I assumed it was rum and Coke - unusual choice to pair with Italian food.

We were both a little awkward and nervous. He grew up in the valley he still lives in, only child. His parents had been estranged for years although never divorced. Both had taken up with other people from time to time.

He was a nerd in the classic sense - loves Star Wars, plays video games. But interestingly he also owns guns, and he and his business partner trick out Subarus for a living.

Turns out that Coke was just a Coke. He doesn't drink, save for a chilled shot of Grey Goose every once in awhile. He also has the blandest palate I could imagine. He ordered cheese ravioli and bread pudding for dessert.

After learning these sobering facts, I thought one and done. How could I date someone that doesn't drink and is as picky and boring as a four year old when it comes to food?

My Tinder profile wasn't as crystal clear as it is now so toward the end of the date I explained my relationship history and how I didn't want to even try to work toward being serious with someone right now - just FWB. He paused, stammered a few words out and then went radio silent on me. In my head, I was like yes for sure one and done.

We walked out to our cars, said our good-byes without even a touch. I drove home confident I would never see him again.

The next morning he thanked me for the evening. I was just going to let our small talk drift out into the ocean, but we struck up a conversation. I reiterated my desire for only FWB and he said he was ok with that - just that no one had been so direct about it with him before so he didn't know what to say. Yes, direct Jersey girl at your service!

He asked me out for the weekend saying we could "get into trouble." Yeah sure straight-laced guy! Then he mentioned going to the city for an overnight. Oh wow, ok! I appreciate stepping up your game. Scary to think about going on a second date to a hotel room in the city with someone I barely knew, but I was intrigued - so let's do it!

I met him at his mom's house just to drop my car off - no mom siting. We jumped in his beat up Subaru and off to the city we went.

Second date, going to the city, no idea what he has planned - living on the edge of fun or being hacked to pieces - who knows?!?

We drove to the Intercontinental Hotel at the top of hill overlooking the city - ok impressed Nerdie! Valet park, check in, it's 3PM, king sized bed, ohhh...

Since he told me he only drank vodka, I bought him a bottle from one of my favorite local distilleries as a thank you present. Least I could do for a second date that would probably cost him a cool grand.

We were both peckish so he ordered a cheese plate from room service. He drank a little vodka and I had some wine I brought.

First plans he shared was to go to the bar at the top of the hotel when it opened at 5PM.

I knew this was going to be a fun evening and I would definitely drink a bunch. For me that means diminishing chances for an orgasm during sex. Plus with a little time to kill I was just so curious that I went for him. We pushed the plates aside and started kissing.

He laid me on my back. Lots of passionate kissing, bodies rubbing, clothes peeling off. Grinding of his thigh against my pussy. Getting heated.

He unzipped my skinny jeans and cupped his hand around my pussy, pulled up hard and then put two fingers inside me. He whispered, "You are so wet for me," in my ear.

He then peeled my jeans off to reveal no panties (don't do them with skinny jeans). A pleased look of surprise washed over his face.

He moved down my body with his mouth. First sucking on each nipple while fondling the other. Then kissing my waist and belly while grasping my hips firmly. He moved further down and began kissing my pussy lips. At this point my hips and body moved without consciousness, my eyes closed to enhance the sense of touch.

He licked my pussy and clit as if he had done it a million times before - like a cherished, dog-eared book he had already read and knew every story line and word to. I was astonished and overwhelmed.

I came quickly, easily, with great pleasure. He stopped immediately afterward, but I continued to grab, kiss and push on him. After a few minutes, he said, "I'm gonna fuck you later."

"No," I replied, "now AND later."

I unzipped his pants and ran my hands over his hard cock still in his underwear. I pulled them down and everything off. He pushed me back on the bed and then rammed his cock inside me. I still felt the tail-end of my orgasm and the hard penetration extended the feeling of bliss.

I watched him watch his hard cock slamming into me and back out again. So fucking hot. I ran my hands over his shoulders and biceps. It didn't take him long to yell out, explode and then collapse on my chest.

Act One scene!

We did finally get into our fancy clothes and up the elevator to the hotel bar. He wore a deep red button down, and I put on a flirty blue dress with a frilly angled edge that I bought in New Orleans. I pulled out of storage my 4" spike heels with open toe to reveal my new purple-black pedi.

Because of the "Now", we were 20 minutes late for the bar opening, so the wait was long and all the window tables had been taken.

We had an early dinner reservation at a restaurant his dad frequented during his long career as a banker in the city. A very casual, quirky Italian restaurant in the Italian neighborhood.

We had one drink and jumped in an Uber.

I let him order dinner, I ordered myself red wine. I was feeling happy, I talked a lot. Told him about my 17 year relationship (with PhD) that had ended about a year ago, and how our sex life was shit, but I had been faithful and monogamous to the bitter end. During all those years, most days I masterbated in the shower before work. We fucked 2-3 times per month, maybe. It was miserable, but I had absolutely no idea what was possible in relationships until I started reading and exploring over the past year.

I offered to pay for dinner and requested a glass of limoncello. It was not on the menu, but the waiter left abruptly and went behind the bar. We couldn't see what he was doing back there. Finally he emerged with a half a glass of the secret stash. I felt privileged and it was delicious!

Early for our next adventure, I walked extremely deliberately in my 4" heels down the major thoroughfare to a Tiki Bar I knew a few blocks away. He finally joined me for another drink.

Uber to the club, and we had a small table right near the dance floor. Two more cocktails for me and a few shots of Grey Goose for Nerdie. We yelled at each other over the music while people watching. I waiting for a familiar song to dance to. It never really materialized.

We commented on what was surely was an escort wearing knee high boots and a tight sweater-fabric dress in which there was no way to bend over in a "lady-like" fashion. I made it to and from the bathroom without incident.

The hotel was just three blocks away, but there would be no way I could walk that with those shoes on and that amount of alcohol sloshing around in my veins.

He called an Uber while we were on the steps of the hotel. I got distracted by a homeless Rasta man who started singing to me and walked away a few steps. Nerdie was trying to wave down the car while pulling me away from the serenade.

That's where my memories of the night ended. The following the stories were retold to me the next morning.

Once back to our hotel room, we started smooching on the edge of the bed. Things got heated and the "Later" sex started happening. I laid back across the bed and he pushed his hard cock against my panties. He started taking off his pants and intended to push them to the side and ram his cock in me. Unfortunately, he had to stop because I was mostly falling off the bed.

"You almost broke my dick!"

Thank god I nailed the "Now"!

I undressed and insisted I sleep naked.

In the middle of the night, I wondered toward the bathroom, but apparently went for the hotel door to the hallway in my birthday suit. He jumped up, and pointed me in the right direction. Successful trip, no incidents.

I insisted repeatedly that I don't throw up. True, I haven't since 1999, and the record wasn't broken that evening. Then I passed the fuck out.

When I began stirring around 10AM, I opened my eyes to reveal a large white expanse of bed in front of me while my naked ass was pressed up against his cock. I had crowded him almost right off the bed the entire night. He hung on to me for dear life for hours.

While he retold me this fantastical tale, I froze waiting for his voice to sharpen and his face to get angrier, but it never happened. We both just laughed and laughed.

After a greasy breakfast, we drove toward his home. He showed me his work. Then we stopped for ice cream at his favorite place a neighboring small town. I was smitten.