Happy endings: Turn over sir

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Long before my nuptials, and somewhere around 2 girlfriends ago, (15 years ago) I wondered in for a massage with a middle aged woman that a friend recommended. She was older, but still very sexy for her age. She was very small, petite even, but she had very strong hands for her small size. None of this is extremely relevant to the happy ending story, but hey, why not.

After the introductions, she left the room and I undressed. I kept my underwear on as this has always been how I do this. She came back in, and she massaged my back. She was strong, but gentle at times, almost sensual with her fingers. I’d been to many massage places, and had men and women work on me over time, but this was different.

Turn over sir, that’s what she told me after awhile. I didn’t think anything of it, they massage the back of your body, and then they massage the front of your body. I was relatively young and inexperienced, and though I had heard of happy endings, I literally had no idea what was happening.

She massages my chest, shoulders, and then whispers a question in my ear, “Are you police?” I turned and looked at her, still completely unaware, “Police? No, I’m not the police.” She smiled softly, “Are you sure, if I ask you have to tell me?” Again, I replied that I was not a police officer and I wasn’t sure why she was asking me this.

She smiled at me, and then her hand effortlessly went inside my underwear. That’s when everything hit me, and it all made sense. She began to touch and play down there. Now I’m thinking, “Holy crap, this woman is about to give me a happy ending.” She pulled my underwear down, pulled out some oil, and went to work on me. She looked at me and asked, “Is this okay baby?” At that point, what the hell was I supposed to say? There was no turning back now, so I replied, “Yes, I’m okay.”

I was very nervous, I had never experienced this before, and she could tell. “First time?” Yes, this is my first time, I didn’t know this was real. My mind was going crazy, “what if the cops break in here? What if I get some skin transmitted disease? Did she was her hands?” I was bugging y’all, and junior was not responding. Obviously she could tell I wasn’t responding, and she said, “relax baby, he won’t wake up if you too nervous, not good.” She continued to play until I calmed down a bit and nature took its course.

At that point, we hadn’t discussed tip or anything, and in hindsight, I think she took me for a ride on what the customary tip was. She over suggested the amount by nearly $60. I later learned what the usual rate was, and realized that I got robbed.

This experience is not something I’m proud of, some would argue I should not share it, but it is part of my history, and my New York story. Also, I’m sure that legally I’m okay, there is no proof that what I’m saying is even true, I could totally be making all this up. Anyway, you’d be surprised how many men in this city have done this. In some cases individuals who I’d never think were capable of this, have told me that they have partaken. Once I started seeing my now ex girlfriend, I left that stuff alone, and have never returned since, but that was one interesting experience, and it all began with the words, “Turn over sir.”



Note the date on a post as it may be an old point of view. If you learn that your views are wrong, yet they remain the same, then you are a fool.

The opinions and views expressed are solely those of the author.