The Reality of a Hooker

The bars and restaurants were reopening on the island. Things were returning to normal, so he found himself, sure enough, sitting at a bar watching the tourists. And thinking about something from long ago.

It was indeed a long time ago.

That as a young man he headed to this island for the first time, where he had read that there were both legal and non-legal prostitutes. He had determined he would find one and have an experience with a prostitute while he was there.

He checked into the Holiday Inn, which had more of a family vibe. Not the place where you’d meet a working girl, be they legal, or not.

He tried to do some of the touristy-like things available, such as a glass-bottom boat tour, but his mind kept coming back to his mission of finding a commercial liaison.

He was young and inexperienced, what to do?

Ask a cab driver, a bellhop, someone that looked like they might know.

Somehow he found his way to a certain hotel in the downtown area. And found his way to the bar. There he saw her. She looked like a Swedish actress he couldn’t think of the name of, but she also reminded him of a girl he knew in high school.

He watched her. A guy approached for negotiation, and then the departure together. He watched her return to the bar after about thirty minutes or so.

How to approach? What to say? He got his courage up. And sat down next to her.

What should he say: Excuse me, are you a working girl? I noticed you leaving with that guy. So how much do you charge?

He didn’t know how you did this, for he’d never done this before. Luckily she had. First, she smiled at him. She opened the conversation, “You looking for something, darling?” Her accent was foreign of some sort. It seemed odd that she called him darling. But perhaps that was just a thing. His response was based on movies he had seen.

“Some companionship for a little bit?”

She smiled again. “How old are you?”

He tried to sound mature, “Old enough.”

Her face became business-like, yet she responded, “You’re kinda cute, one hundred American for thirty. You here?”

“Holiday Inn.”

“Okay, we’ll get a cab, unless you have a car?”

Now he smiled, “Let’s get a cab.”

The cab ride seemed longer than it should and cost more than it should.

No one seemed to notice them as they moved through the lobby of the Holiday Inn. Soon in his room, the transaction continued.

She picked up on his awkwardness. “You can put the money on the dresser.”

Not having any experience, he did.

Before he knew it, she was standing naked before him and moving erotically. He pulled off his t-shirt and sat on the edge of the bed.

But slightly caught off guard, he responded, “Can we just talk a bit. I do have thirty minutes, right?”

“Sure, darling.” She sat down on a chair in front of him, yet still touching her breasts.

His erection was tight in his jeans. He wanted to slow things down. It seemed like his arousal had trapped him in place. He was captured by his desire.

“What do you want to talk about, darling?”

He didn’t know. He blurted out, “You remind me of this girl I knew in high school.” He thought of that girl and that time with her at his parent’s house when they were out of town.

“Really, darling? Did you really like her?”

She spread her legs and started to touch herself. He continued to watch her.

Suddenly she lunged forward and her hand found his crotch, and with several quick strokes, “Did she like you like this, darling?”

His erection exploded inside his jeans.

She was truly an experienced professional. He would not be inside her for this transaction.

“Oh darling, that’s okay.” Before he knew it, she was dressed and taking his money, and heading out the door.

He sat spent at the edge of the bed. He felt foolish. Why did he bring up that girl from high school? He felt embarrassed by the whole thing.

He pulled his jeans off. Amazed by the amount of semen in his underwear. He stripped, and headed to the bathroom. As he washed his underwear in the sink, he vowed to himself that he would never use a prostitute again.

And that was a long time ago.

....As his mind came back to the present, and the newly reopened bar full of tourists, he noticed her across the room. He watched her sit down at the bar. She reminded him of a girl he knew in high school.

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