May 19, 2021

After 21 years of Sex with the Same Person, I had my First One-Night Stand. {Adult-ish}

*Adult language!


For about a year, it held the record as my first one-night stand.

I explain later how that changed.

I got married when I was 18, so it was also my first time being a single adult. Not only was I mourning my marriage, coping with issues of abuse, and trying to heal myself, but it was a brave new world of internet and dating apps.

These things weren’t around when I was a teenager. How do I meet someone—shit, how do I approach a man? What the hell is Tinder and how does that work? All of it seemed so overwhelming. Such impossibly scary things to learn and navigate.

I was 39—holy fuck! How do I do this?

I threw myself into healing first before diving into Tinder waters.

First: I am stubborn and was hell-bent to get through this and learn a new way of life.

Second: I took advantage of services provided to me through my local domestic violence agency, including counseling and assistance with legal costs for a divorce.

Third: I started practicing yoga—something I had wanted to do for a while—from a DVD that was given to me as a divorce present.

Fourth: I reached out to family and friends for help and advice.

Fifth: I explored so many options of me and adapted a no-fear attitude to the point that I went sky diving and got tattooed. These were things I had sworn I’d never do.

I wanted to learn, grow, and evolve from this major life change as best and as quickly as possible. I explored this path to learn about me before I could even think about being with someone else.

After about six months, I regained a sense of who I was and an ability to feel safe. I now wanted to put myself back out there and explore the wilds of singlehood. I wasn’t going to live in fear anymore, and this was part of that. I wanted to do a dry run of going out in public, single, and free to be me.

Through my life experiences and over time, I’ve learned certain safety tactics. Like parking under a street light, walking with a key protruding between my fingers as a defense measure in case someone grabs at me, among several other things. Knowing and using safety measures helped me a lot through this process.

So, I decided to go out—by myself.

The local mall had a nice outside food-court style area with a handful of restaurants, from Cheesecake Factory to Panera Bread. Most all of them had inside and outside seating. There was even an optional valet service for restaurant patrons after mall hours on the weekends and certain holidays. Among the restaurants, there was a bar that I had been to before. It was familiar and there was enough foot traffic I felt a level of safety.

I remember walking up to the door that was covered in promotional stickers and stopping to take a breath before pulling it open to cross that threshold. As I took this breath, I felt the air go into my lungs. This helped me memorialize the moment, curb anxiety, center myself, and muster up enough gumption to open the door and walk into the bar.

Thank goodness for yoga and learning how to come back to the breath.

I didn’t go with the specific goal of hooking up with someone but it was a thought I had toyed with a little. My main focus was to go out alone—by myself and be myself, successfully.

The bar had a wall of craft beer taps. If you don’t know craft beer, it’s the “special” made stuff they charge more for because it has a higher alcohol content and it’s just fancy. That isn’t a big selling point for me. I prefer the cheap domestic ones, like PBR, instead of craft. But my reason for being there wasn’t the beer.

I found one I liked enough and had a couple to acclimate myself to the surroundings. After all, it was a bar, and I wanted to fit in. Bonus, having a couple also helped take the edge off.

While I watched whatever football game was on and was interesting enough to pay attention to, a guy stopped by my patio table and started a conversation. I guess he noticed I was sitting by myself. After a couple of feeler lines: “How are you tonight, where are you from, are you here with anyone,” he asked if he could sit and we could keep talking.

I said, “Sure.” And was intrigued.

We had a pleasant conversation. Mostly random this’s and that’s, but there was a mutual flow and rhythm to it. It wasn’t awkward, uncomfortable, or forced conversation. We talked enough to get some basics and a vibe of each other. He seemed to be a decent enough guy. I didn’t have any of those danger warning feelings, like hairs standing up on the back of my neck or an uneasiness in my stomach. He learned I was newly single, and I learned he was in town on business.

According to the card he handed me, he was, indeed, in town for business. I figured I wouldn’t see him again. So, when he asked, I agreed to meet him at his hotel.

What a great opportunity for my first new-to-me dick in 21 years: can I have sex with someone who isn’t my husband?

No strings attached sex with someone I won’t run into again. For me, it seemed like a good way to dip my feet back into single waters. I felt empowered to be myself and let my soul shine.

Despite some fear, I wanted to get past this hurdle too and took advantage of the opportunity presented to me.

We met at his hotel, which wasn’t far from the bar. I was prepared with condoms and let someone know where I was just in case–another safety measure I took. After sex and a little cuddle time, I politely excused myself. I more than accomplished my original goal and wanted to go back to my own bed. Also, I was not ready to be vulnerable enough to actually fall asleep with someone else. That would be a task for another day.

I cleaned myself up a bit, got redressed, gathered my things, and checked my face. During this process, he asked if I was okay. When I answered that I was going to head home, he was thoughtful enough to give me a hug and kiss, and help make sure I had everything, including a safe way home.

I left in one piece—without being murdered, raped, or freaking out—I can do this!

As I went back to the safety of my home, I had an overwhelming feeling that I can survive and thrive. I can be me, and be okay. Plus, successfully get laid.

Well, successfully have sex with someone who isn’t my ex. Sad to say it wasn’t great sex. But a feeling of, woohoo I can do this, helped me sleep that night. Surviving everything the past six-ish months and realizing that I can have a new life was better for me than great sex.

About a year later, and some more experience, I was at that bar again.

This time, I was more comfortable going out by myself. Still keeping safety in mind, I sat at a bar-high table on the patio, again by myself, this time listening to an unknown cover band that happened to be playing that night. After a couple of beers, I went inside to use the restroom and noticed him sitting at a booth with a group of people. Not knowing who he was there with and not wanting to approach him with a, “Hey, do you remember me,” line, I just peed and went back to my table.

After cashing out and tipping appropriately, I went walking through the parking lot to my vehicle—still with my keys positioned defensively. I noticed him leave behind me. When I heard him call out to me, I stopped and turned.

“Do you remember me?” Seemed kind of ironic that he used the line instead.

“Yeah,” I added his name.

He explained it was that time of year again to be in Florida for business and was having drinks with colleagues. Turned out he noticed me too when I went inside. After a couple of quick feeler questions—hey how you doing, what’s your situation—came the question.

“Do you want to meet up at my hotel?”

I figured, why not? I don’t have anything better to do the rest of my night. I could use some sex and there was a level of familiarity.

The guy who I was never supposed to see again was in town the same night that I went to that bar on a whim? Hmm, things do happen for reasons, right? Going with the flow and listening to my gut hasn’t led me wrong yet. I’m still okay and still happy being me.

So, my first one-night stand turned into a second-night stand. It still wasn’t great sex but having physical contact and the synchronicity of it helped me sleep better that night. I had a coming-full-circle kind of feeling.

Even though it wasn’t great sex, it was still good for me.


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