The Pineapple Diaries

The Pineapple Diaries: The Long Game

Patience. Sometimes what seems like a dead end turns into something more—it just takes time.

John and I had a friendly connection that began, and for a long time remained, firmly on the main floor of the club. He is a frequent guest and possesses all the qualities I look for in a potential connection: tall, completely devoid of that desperate thirst for action, and armed with a good personality. We could banter back and forth without him crossing lines or taking my sarcasm personally.

There was just one roadblock keeping us out of the playroom: his arrangement didn’t quite mesh with what I was after. His partner wanted to at least be present to watch. I didn’t fault her desire and respected it completely, but as a woman who genuinely does not enjoy an audience, it was obvious we weren’t going to connect on that level.

That didn’t mean we avoided each other. There was always a casually friendly acknowledgment, sometimes punctuated with a physical hug, and always served with a side of playful lust. I was content with what we had built. It’s always good to have friendly connections at the club. But I’d be lying if I said I wasn’t incredibly curious about how he operated behind closed doors.

The Compromise
There is a massive misconception in the lifestyle that women can simply snap their fingers and get whatever they want. It gets incredibly frustrating when you find someone you genuinely click with, but the logistics just don’t align.

Or so I thought.

A few weeks prior, something shifted. A bit of slightly intoxicated banter led us to a clever compromise: the glory hole room. It is a rare occasion that I tolerate a physical barrier between myself and my… skills. Usually, it’s only an option I use if I am actively trying to impress someone. But here, it worked perfectly. I could remain securely behind a closed door without an audience, while his partner was able to keep her eyes on him however she wanted.

After a few minutes of oral acrobatics, he pulled away, leaving me highly intrigued and wondering what could have been.

The Hallway Proposition
Fast forward a few weeks, and we were both at the club again. The friendly banter felt just a little bit different this time—heavier. The previous experience was clearly enough to make a difference, but I didn’t read too much into it. The obstacle of his partner was still there, but I happily returned his attention all the same.

I was on my way outside for a few minutes of fresh air when it happened.

He was casually leaning against the wall near the doorway. I gave him my usual smile as I walked past. He returned it with a small, deliberate come here motion of his finger. A bit coy, I shot him a questioning who, me? look. He nodded.

I don’t think I have ever been propositioned so directly and completely out of the blue. I was actually speechless. His offer was incredibly simple: Did I want to go to a room? Of course I did, but mentally, I was nowhere in that frame of mind. I honestly told him I wasn’t sure, simply because I was caught totally off guard. He responded exactly as a veteran should: with understanding and space. He told me to go get my fresh air, and that he would be right there when I came back inside if my answer was yes.

The Veteran’s Takeaway
I ventured outside and let the thoughts spin. My husband—never clinging, but always aware of where I am—met me outside a few moments later. I filled him in on the current dilemma.

Without much hesitation, he suggested I go for it. Then, with complete deadpan seriousness, he told me to make sure the curtain on the door’s window was cracked just enough so he could see. He was joking, knowing it was highly unlikely I would leave the room open for any eyes, but he had to ask all the same.

I walked back inside, found John hanging at a table, and gave him my green light.

What I later learned, after we thoroughly enjoyed each other behind closed doors, was that he and his partner had recently decided to start exploring solo play. I was his very first one. That realization made me feel amazing; it proved there was a profound level of trust established between all of us.

Sometimes, the wait pays off. We had a fantastic time, and I have a feeling there is much more to come.

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