Most days, Ms. Anne would be dressed like one would expect of a preschool teacher, comfortably and conservatively. I could still tell that she had a pretty good body and the smile on her face each day was all the makeup she needed to be attractive.
I had developed a bit more of a relationship with her than most of the parents at the school as I often would be the last parent picking up their child from school. It wasn’t anything beyond professional but we were friendly with one another nevertheless. I was a single parent, busy building a business, and she had a way about her that seemed to slow and calm everything down.
And then it happened one fateful, Friday night. I had arranged for a babysitter to watch my son so I could take an important client out to dinner for the evening. The dinner went well, and, afterward, we headed to the bar at the hotel he was staying at to have a few drinks to wrap up the night.
It sounds cliche, but only because it happens all the time; high-end, hotel bars are ripe with traveling businessmen and entrepreneurial-minded women looking to do the oldest business in the book. This hotel bar was no different. As two well-off-looking gentlemen ordered top-shelf booze at the bar, we basically put a sign up saying that we were prime targets to do business. I had only stepped away for a moment to use the bathroom when I returned to find my client talking to a knockout in a tight black cocktail dress and heels leaning into him and playfully laughing while touching his arm. She had her back to me but from what I could tell, whatever she was charging would be well worth it.
I made my way back to the bar and as I came upon them, my client and his new friend turned to greet me at the same time. My client was quick to introduce us, “Meet Rhiannon, she’s meeting a friend here but they seem to be running late. So she’s suffering the company of yours truly.”
My jaw almost dropped and so did hers. It was Ms. Anne, but not the daytime, kid-friendly version. This was her nighttime, adults-only side that I didn’t know existed. Her hair was done up in a nice bun with curls hanging loosely from it and her eyes were accentuated tastefully with eyeliner and mascara. She had an alluring shade of red lipstick that made me realize how full her lips really were. The front of her dress had a plunging neckline with a gold pendant dangling between two of the nicest tits I had seen in a long time. She was absolutely killer, all dolled up. I just barely managed to pull it together in time to extend my hand to say, “It’s a pleasure to meet you, do you come here often, Rhiannon?”
She gave me a smile and coyly replied, “Only once in a while. It was my friend’s choice tonight, but she seems to have forgotten where she chose to go.”
It was clear to me that she wanted to avoid acknowledging that we knew each other, and I was willing to go along with it for her sake. Before I could say anything my client jumped back in eagerly, “I’m that case, it would be our pleasure if you joined us for a drink until she arrives. How does that sound?”
Ms Anne or Rhiannon as she was calling herself tonight flashed me a smile and accepted the invitation, “That sounds lovely. I can tell you two are both gentlemen and I’d be happy to. Let me text my friend though to let her know she’s missing all the fun.”
I didn’t know where this was going but I was willing to let it play out. I moved out tab from the bar to a lounge table with two sofas on either side of it. I sat down on one side and my client and Rhiannon sat on the other. Her dress rose up her thighs as she sat down and crossed her legs, showing off her creamy white skin and her toned legs. My client wasted no time in getting his arm around her. It sent a shot of jealousy up inside of me, but seeing her like this and watching her work what seemed to be her “night” job was also alluring and sexy as hell to me.
She was good at it too. She laughed at all of his jokes and touched him just enough to get him going while only allowing herself to be touched enough to let his mind run wild with the possibilities. If she had wanted to close the sale right then and there, she easily could have. But she didn’t make any move to do so as far as I could tell and my client, despite his best efforts to whisper in her ear, was not having any success in moving their party back to his room.
I was a bit confused but Rhiannon insisted that she was waiting for a friend to arrive and that she’d be joining us any minute. I was actually surprised when another beautiful woman arrived in an equally stunning outfit. Upon her arrival, Rhiannon stood up from the sofa, allowing my client a great view of her ass that was barely covered by her little black dress, and proceed to give her friend a big hug. Both my client and I watched this scene as we both imagined the two of them putting on a show that involved a lot more than just hugging. My client and I looked at each other and smiled as we both knew we were having the same thoughts at the time.
Rhiannon broke her friend’s embrace and turned to introduce her to us, “Gentleman, this is Michelle. Would you mind if she joined us?”
My client was quick to reply “Not at all, please have a seat. We’ll get the waitress over and get you a drink.”
And then Rhiannon pulled a fast one by directing Michelle to sit next to my client as she locked eyes with me and walked over to me and sat down beside me. I didn’t know what to make of it, and my client didn’t either. But, Michelle was more his type and was already flirting with him and complimenting him on his Rolex and the other expensive aspects of his attire.
Where Rhiannon was coy and subtle, Michelle was bold and brazen. Michelle was a shark and she smelled blood in the water with my client. It didn’t take long before the two of them decided that they were going to “call it a night,” and they were walking out of the bar together.
When they had made it out of the bar, Rhiannon and I looked at each other and both laughed hysterically. I think we were both thinking the same thing but she said it first with, “Oh my gosh! What are you doing here? You can’t tell anyone about this at the school. I’d be mortified!”
I reassured her by telling her the truth, “I would never, and your secret is safe with me. Even if that secret is that you’re a stunner when the sun goes down and you seem to have made my client’s night by talking to him and then by setting him up with your friend. Or should I say, business associate?”
She blushed and my suspicions were confirmed. She was working, and I had caught her. She didn’t seem ashamed but I could tell her cheeks were beet red even under her makeup. She tried to regain control of the situation by telling me, “It’s not something I do all the time, but I could use the money and these guys pay so well.”
I had never paid for ladies’ services at a hotel bar and I had so many questions about how it all worked and her experience with it. I could tell that we were entering a potentially delicate area for her so I chose my words carefully, “Anne, I have no intention of judging you or telling anyone about what you do with your time. And, if I can be totally honest, I’m actually very intrigued by you and would love to know more. I’ve always thought you were attractive, but the way you look tonight is on another level.”
She blushed again and looked down. Then she turned toward me and put her hand on my hip as she leaned in and kissed my lips deeply and sensually. It was electric. I didn’t care who was watching because everything else disappeared at that moment. I put my arm around her and my other around her waist and pulled her in to kiss her back.
I don’t know how long it took but we eventually came up for air and both laughed again as we did. It was almost a nervous laugh but it was more like a relieved one instead. It was as if we both had been harboring feelings for one another and didn’t realize it until tonight and then so much tension had been building up until it was all released in that first kiss. We laughed more. And I finally confessed, “This is amazing. You are amazing. How have we been missing this for so long?”
She smiled, “Kids do tend to take up a lot of our attention I suppose. But, I agree, this feels really good. I’m a little worried though. Are you really not phased at all that I’m a part-time sex worker?”
“Phased? Not at all. In fact, the thought of you being with so many men really turns me on. I think it makes you even sexier to me.” Whether she knew it or not, I had just made a confession to her that I liked sharing my woman with other men. It was one of my fetishes, and she was literally exposing herself to be the girl of my dreams.
She kissed me again and her hand ran over my chest and my pants. I was at half-mast before but her hand squeezing and the kissing was well on their way to raising my flag completely.
I didn’t have a hotel room but my condo wasn’t far away. I caught the waitress’s attention and let her know it was time for me to cash out of this casino because I had hit the jackpot!