The 3 Prostitutes That Surprised Me

Or, The Good, The Bad, The Ugly (But Not In That Order)

Three times, I’ve been surprised by a woman soliciting me for sex. The first time caught me off guard because I had a stereotypical idea of prostitution. The second woman shocked and enticed me with her brazen approach. And, the third surprised me with her humanity. We never know what leads people down their paths in life.

I had no idea at first that any of them were prostitutes.

I’ve never gone public with this. I have, however, told a couple of close friends and my wife.

Wait. You told your wife about the prostitutes?

Yes. I tell her everything. Well, nearly everything. 80% for sure. Hmm. Let’s call it a solid 50%. And the prostitutes? Yeah. Of course I told her about them.

Why wouldn’t I?

These three women completely surprised me. And this story is not intended to disparage or diminish them. They’re people. It’s also not meant to glorify them or overly sexualize them.

It’s not even to say, “Look at what a great guy I am for saying no all those times.” I probably come off as a bit of a doofus in this true tale. You decide.

I’m just telling my surprising (to me at least) story.

The First Prostitute

This one is the easiest to explain. I was younger, newly married, and more naïve than I liked to admit. At the time, I’d never met a lady of the night.

Although, in light of this story, I should probably say I’d never met a lady of the night…to my knowledge.

I’d just had dinner with a college buddy. For the sake of the story and to protect his identity, we’ll call him Aberforth. We’d met at his work downtown and left his car there.

We anticipated a nice meal, strong coffee, and maybe a game or two of pool. I may not have told my wife we were shooting pool. I don’t remember, but we can put that into the 50% I don’t tell her.

This detail is relevant because I was anxious to get back home quickly. Something had kept me longer than expected.

I pulled my car back into Aberforth’s company lot. We got out and said our goodbyes.

That’s when she walked up.

“Hi fellows,” she said. “Can one of you give me a ride to The-Street-Name-Is-Long-Forgotten Street?”

Note, she asked for a ride… to a street. If she’d asked for a ride outright, I might have picked up on the innuendo.

Instead, I said, “I’m in a rush to get home. Aberforth, do you have time to take her?”

Aberforth looked at me with something bordering on agitation and anger. But he agreed.

When I got home, he called me.

“Scott,” he said. “The next time you offer a prostitute a ride, take her yourself.”

“But, she wasn’t a — ”

“Yes, she was.”

“But,” I protested. “She didn’t look — ”

“Trust me. She was.”

“But she was ugly,” I finally managed to get out.

Yes. I judged her completely based on her looks. I’m sorry. But really, I wasn’t judging her worth as a person. I just thought anyone doing what she was doing had to look like what you saw on tv and movies.

In my mind’s eye, all streetwalkers looked like Vegas showgirls. At the time, I’d never been to Vegas, which meant even my impression of Vegas showgirls came from Hollywood.

The woman looked nothing like a Hollywood starlet, so naturally, my guard was down. This probably says something about my mindset at the time, but I couldn’t tell you what.

“So,” I asked, “did you — ”

“No!” Aberforth said. And I believed him.

Not everyone goes into prostitution by choice. Some are forced. Of those that aren’t, I imagine most do so out of desperation. I’m sad to say that, even with it being something I would never partake in, my mind had glamorized it.

This was a real woman who looked to be in need. It opened my eyes, if only a little.

I told my wife. I forget her exact words. Basically, she said I needed to be more aware. And she was right.

The Second Prostitute

Fast forward a few years.

I was living in Florida at the time. Still married, I had two young daughters. Moreover, I’d like to think I was an upstanding member of the community.

I owned a business at the time — a pizza restaurant. I was coming from having closed the store and needed a quick bite to eat. I’m not proud of this but I pulled into McDonald's. This was before I started writing health and fitness articles. I promise.

As I pulled out, a young woman across the street waved at me. It was drizzling, and it seemed like the rain was only going to get worse. The woman seemed to be in some form of distress.

I pulled over. She asked if she could get a ride.

Yeah. I know what I said about the first prostitute’s wording. But I didn’t even blink at her phrasing.

I let her in and asked where she wanted to go. Instead of a destination, she gave me directions. Sort of.

“Just go down this street,” she said.

“Okay. Where are we going?”

“Depends,” she said. “Are you looking for a date?”

Her shirt, wet from the rain, was sticking to her chest. I noticed. “A date?”

She put her hand on my thigh. I jerked, drove off the road, head on into a police cruiser.

Just kidding. I stiffened, though. My posture also got tighter. There’s a joke there if you look for it hard enough.

“Yeah,” she said, and moved her hand over my crotch. “You definitely want a date.”

I’d like to say I wasn’t tempted. Her intention laid bare, she began to negotiate. In the end, I declined her services and took her back where I’d picked her up. And I gave her money for McDonald’s. You could debate if that was a good act on my part or not.

I’ve got no great takeaways like I did from the first encounter, except for my own near willingness to do something I’d never imagined myself doing. If the first surprise taught me these women were human, this one taught me I was one also.

I told my wife when I got home, including the part where the lady touched me. I may have told it with less innuendo and skimmed over the part where I was tempted to partake. The point is, I told her.

“You could have gotten arrested,” she said. “You need to stop picking people up.” It wasn’t the first person I’d offered a lift to, though it was the first that solicited me afterward.

The Third Prostitute

This one is my favorite. Don’t take that wrong though. I mean the story. Well, I also mean the story.

I travel for a living these days. This is the part where I hope you don’t hate me. I’ve been all over, including to Hawaii, multiple times.

Have you ever been to Waikiki? When I’m working in Honolulu, I try to stay there. It’s ideal. You can walk everywhere, including to the beach. It’s touristy, sure. As an experienced traveler, I often avoid touristy. But sometimes it’s exactly what you want.

There’s a trick to walking the streets of Waikiki at night if you’re a man that doesn’t want attention from the ladies of the night.

If you walk on the side of the street next to the ocean, you will not be approached. Well, not by working women at least. There’s a story there.

If you walk on the opposite side, and it’s late enough, you will probably be approached. I haven’t done an extensive study on the subject, but late enough seems to start somewhere around 8 or 9 at night.

On my first trip there, I was approached by multiple women, sometimes two at once, which is a sentence that could be a lot more fun if it were that sort of story.

And they were gorgeous. Apologies to my wife, but it’s true. They came in multiple body types, shapes, sizes, and ethnicity. Possibly in multiple genders. It’s impossible to say, but I’ve heard rumors.

And I’m not counting any of these in my count of surprising prostitutes. I wasn’t caught off guard by them. They wore sexy outfits and looked like those Hollywood starlets I mentioned earlier.

Don’t misunderstand. You can’t assume a beautiful woman dressed to kill in Waikiki is a streetwalker. It’s just one of the possible signs.

The way you tell is when they approach you or someone else. If she tries to go to your hotel with you, she’s probably working. Money will eventually come up as well.

I declined every invitation. I was new to exotic locations and assumed I was approached because of the deer-in-the-headlights look on my face.

When I returned a couple of years later, more jaded by travel, I was still approached. And, I noted, so were men in groups. Men in pairs. Men with their wives.

That’s when, with a little bit of observation, I figured out how to avoid them. Cross the street to the opposite side.

I think it was the third trip when I met the third prostitute. The one that surprised me.

I was walking down a side street toward the main strip, when I saw her get out of a car’s passenger seat. She wore something like a trench coat. Whatever it was, it covered most of her body.

She was short, Hispanic, cute, and approached me. Her demeanor was different from what I’d previously experienced, though. She asked if I knew how to get to a particular bar. It happened to be right across from my hotel.

“I sure do. Are you driving there or walking?”

“Walking.” And sure enough, the car she’d been in pulled away. “I’m meeting a friend there, but I don’t usually come to this side of town.”

“I’m heading that way,” I said, now confident that she was just a tad lost.

We chatted on the way until her phone rang. She answered and told her friend that “the nicest guy in the world is helping me find it.”

Before we arrived at the bar, she told her friend, “I see you!”

I looked down the road and one of those drop-dead, gorgeous women dressed in a provocative dress was waving at us. Now, remember, you can’t assume by attire alone that the women are escorts. In fact, my new friend wasn’t dressed remotely like —

That’s when she took off her coat, revealing the tightest mini-dress I’d seen since… okay since earlier that night when I’d crossed to the ocean side of the street.

The change was immediate. She was pretty before. No coat could hide that. I also found her charming. A delight to be around. She remained the same person with the sexy outfit revealed.

But, I’ve done enough stage acting to see the shift. She put on a character. She became a different person, and that person oozed sexuality.

She then tucked her arm in mine and said, “We’re out for a good time. Want to join us?”

And you know what? I kind of did. But I didn’t do it.

“I’m going to my hotel,” I said.

“Which one is it? We’ll join you.”

I made an excuse. I forget what it was. And I left.

There was also no doubt in my mind that they were working. Even less when, as I removed myself from the situation, they gave me their business cards. Yes. If you didn’t know, Waikiki women of the night have business cards.

I was surprised that she turned out to be a prostitute as well. I was even more surprised when she changed into her working persona. When she put on her proverbial mask, it was like an entirely different person stood there.

Maybe it’s because I knew it was an act, but I preferred the persona she’d worn before. The one that I’ve decided to interpret as her “real self.”

If that person had asked to join me in my hotel, I’d have had a harder time turning her down. Especially if that person was wearing the same tight dress as the new woman in the mask. (I’m being honest here.) And especially, especially, if it wouldn’t cost me however many hundreds of dollars they were asking. I never found out the price.

I told my wife about this as well, minus the insight into how much more appealing the real version of the woman was.

My wife asked, “What is it with you and prostitutes?”

I still don’t know the answer to that. I do think I’m much less naïve now. But these were three times I was surprised.

It happened to me.

Scott Hughey still travels for a living. He’s noticed that the streets of Waikiki are much less crowded during Covid. And yet, he’s seen it’s still necessary to walk on the ocean side.