The First Time I met Bill: Delayed Gratification

By now you’ve heard me mention Bill a few times. You remember Bill? He’s the married man I’m in love with (this is where the Lifetime analogy kicks in). I figured it was about time I set down just how my relationship with Bill has come about and why I find it so difficult to untangle myself from this web. In trying to write this I found myself getting lost in our interactions, so this will be written as a series of flashbacks to give you all some context over what this whole relationship has become.

Bill and I met on Tinder about three months ago. Yes, the place where true love happens in 2018. A man in his early 40’s with this glint in his eye that I couldn’t place. His profile was vague enough to keep me intrigued, but with enough content to peak my interest. He wanted a woman who was in touch with her sexual nature (check). His pictures made him look like this salt and pepper fox with a hint of a wild side, exactly my type.

As long as I can remember I’ve had a thing for older men, so much so that my friends in high school made a bet that I would lose my virginity to one of my professors in college, which almost happened, but that’s a story for another day! Back to Bill.

We flirted on Tinder, messaging back and forth. I can’t even go back and look at the first thing he said to me because he’s deleted his Tinder account since then. After a while we moved to KIK, those messages I did read through the other day. It’s strange how much like us they sound (same tone, same complimentary nature from him), but how far we’ve come from those simple, flirty messages about him being paid by my mom to take me out – I realize that sounds strange, but in context, it was adorable.

I think it took us about a week to finally set up a time to go out that worked for both our schedules, which is either average or a long time for me to make someone wait. Before our first date, I had just put a final nail in the coffin of another relationship (within the last week or two), that’s a whole other story, but it was someone I felt a strong emotional connection with, and it ended on terrible terms.

I remember contemplating my outfit for even longer than usual before meeting Bill. I was nervous. He was not a boy. He was a man. I only date men older than myself or my age, but something about him felt so much more mature. We picked a bar close to where he lived, and I remember on my way over there, in the freezing, bitter cold thinking: “at least I’m making the trek out here for some great sex. He looks like he will be amazing in bed.”

I was both very wrong and right in that statement, as he is the best sex of my life, hands down. I can’t tell you how many people I’ve slept with. I lost count. Let’s say it’s over 75 and less than 250. That seems like a safe ballpark. Apparently the kids call this a body count, news to me! Out of all these men, I have to fall in love with the one who is… well, you’ll see.

Our conversations had all lead me to believe that this would be a hook up in some form. It wasn’t explicit but implied. I expected to be seduced. Would there be some foreplay, verbal and otherwise? Yes, but at the end of the day, I didn’t expect more from our interaction than excitement and orgasms. I remember his eyes looked kind and dangerous all at the same time. That was one of the first things I thought when he sat down next to me at the bar. He was exactly what I had expected and at the same time completely different.

I believe that within the first 30 seconds of meeting someone you know if you are attracted to them and want to have sex with them. I knew in half that time I felt that way for Bill. I’d felt the same feeling for the last two guys I’d dated. Our first meeting felt like that, but different. Our conversation was polite. We talked about our work, the news, music (or my inability to listen to anything current). He seemed normal, charming, too smooth, all of which I expected. Someone that age has either perfected their game or has none, there isn’t an in between.

He told me he was originally from Georgia and started telling me this hilarious story about a chicken, all in a thick southern drawl. I think it was then that I began to fall for him. That stupid, adorable, damn accent and that southern charm just about did me in. He very casually mentioned going to a “club” a few cities away. The city is much smaller than the one I live in, and I could only think of one kind of club that I’d heard of there. My interest was piqued.

I’ve been “in the lifestyle” (as they so obnoxiously call it) on and off for 4 or 5 years, since my mid-twenties. One day I’ll tell you all about that. Having been in many dom/sub interactions and being connected to an online community of kinky people I had a feeling that the club he was referring to was a swingers club. I didn’t know of any in my city. I’d heard most people went about an hour south to find that kind of club.

“What kind of club did you go to?” I asked, not accusatorily, but with a grin and some mischief in my eye.

“What kind of clubs do you know about in ******?” he asked me, smiling as if Christmas came a little early.

“I’ve just heard that there is a swingers and kink club down there,” I’d looked away from him when I said that, to give the last part of my sentence more coquettish emphasis, “but I can’t imagine what a nice southern boy like you would be doing in such a scandalous place like that.”

He looked me up and down, then right back in the eyes, a grin spreading across his face which he quickly suppressed. “I can’t imagine what a nice, Catholic girl like you is doing knowing about such things.” I could hear a bit of that southern drawl starting to peak out again, and my excitement mounted.

“You have no idea, Bill, the things that I know.” I quickly replied.

“I have a feeling I’m going to find out,” he said back, putting his hand on my knee and brushing a dark curl off my shoulder.

“That’s incredibly presumptuous of you,” I said with a smile and took a quick sip of my drink. I looked back at Bill, and staring at my body hungrily, a hand running down my leg over my calf covered by my tights.

“I had a feeling when I first saw your pictures that there was something more to you. A darker side that you cover up by dressing and acting like such a proper young woman…”

“Acting” I interjected, half in mock offense. Bill didn’t know me well enough to make such assertions, all of which were eerily true.

“Acting, but behind closed doors, I sense that you like to submit to your men. Am I wrong?” he finished, looking me boldly in the eye, daring me to prove him wrong.

I contemplated playing coy. I contemplated drawing out the line of inquiry or spinning things back on him. I contemplated deflecting. At that moment, I just went with my gut. The wonder of how this man could read me so well.

“Bill, am I that transparent? I’ve been told I hide my… proclivities very well upon first meeting someone.” I was curious, but not ready to give everything away with a full confession.

“You do, much better than most. It’s one of the things that makes you so incredibly seductive and attractive.” At that, he leaned in and started speaking very huskily in my ear (I honestly thought people only did this in movies). He moved my hair aside and stroked my neck and ran his hand down to rest on my lower back.

“Something I look forward to learning more about when I do get you behind closed doors. I intend to explore every inch of your body.” At that, he pulled away from me, gave me a knowing smile and went back to drinking his drink.

I wouldn’t have been surprised if my mouth was left agape at that moment. It was one of the most sexually arousing things I’d experienced, and I’ve experienced some Christian Grey level shenanigans. This interaction was erotic, the promise of what was to come.

I learned later that night that he had a ‘no sex on the first date’ rule. I think I had a tiny, tiny stroke when he said that. All that talk, all that excitement, and my lady boner would go wasted! His work kept calling him and texting, and he finally said after two and a half hours that he had to go back to his office, but that if he hadn’t, he would have taken me home.

“Take me home? But you have a no sex on the first date rule?” I asked accusatorily. In my brain, I was plotting ways to ruin this company in the next 4 minutes and make his appearance at the office unnecessary.

“I may have that rule, but that doesn’t mean I couldn’t use my mouth on you until you came a few times.” He starred back at me with an amused look on his face. I’m sure I looked flabberghasted, but I tried to hide my mixture of excitement, shock, and disappointment in a statement of neutrality.

“I suppose it doesn’t matter what I’d prefer since your employer is preventing me from having the option and opportunity to find out,” I said, my annoyance genuine.

“I promise I will make it up to you the next time I see you.” he squeezed my knee and asked for the check. He walked me to the train station, a concert had just let out a few minutes before, and people were starting to matriculate into the station. We stood inside the station, and before I could begin to say anything about goodbye or I enjoyed myself, he pulls me in at that waist with one arm toward him and with the other guides my head towards his for an intense and primal kiss.

You know how you read about the whole world slipping away, forgetting anyone is there when you are in the throes of passion? It’s how I felt with him at that moment and still do now. We are nothing but a jumble of hands and lips, roaming, caressing. It felt like 20 minutes of this but was probably only 3 or 4 at the most. Eventually, he pulled away and said, he hates that he has to leave but has to go to work and that when he gets back into town in a week, I’m the first thing on his agenda.

During the next week as we texted, I remember him saying that he thought I wanted to go home with him that night. That “your kiss told me you wanted to come home with me. That and your eyes.” He was right on both, but I played it as cooly as I could for the next week until he was back in town.

That’s a story for another day.


Thinking about those first interactions, part of me wishes I could send a quick text to myself before this date saying “this guy is going to give you more pain than you’ve felt for any man in your entire life.” Would I lie to my past self and tell her that by not meeting Bill that night she would also be denying herself the most intense and exquisite pleasure? Since I am a bit of a masochist, I have a feeling knowing what I know now; I’d say “screw your courage to the sticking place.” I’d take the pleasure with the pain, and get that drink.

Up to No Good 😉

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