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My First Night as an Escort (part 1)

My first night as an escort didn't go exactly as planned...and that's OK.
The sun was just starting to set behind the buildings as I sat at my desk finishing up my work day. I was the last one in the office, having stayed a bit late getting things wrapped up for a big project our company was working on. The office was dim and quiet, so I was a bit startled when I heard my phone vibrate softly in my purse. I dug into the pocket and pulled it out, wondering who would be emailing me at this time of night. I was pleasantly surprised to see that it was an email from my new website I had just set up. “Wow, that didn’t take long," I thought to myself as I opened the folder. It was from a potential client and my heart started pounding. I had no idea how these types of transactions would go, since I was so new to the escort business. I opened the email.

“Hello there. I came across your website and photos, and was immediately intrigued. You have a gorgeous body, and I am very interested in meeting you. I was wondering if you might be available this weekend for a drink somewhere downtown? Let me know. Talk soon.”

“Oh Dear God – this is really happening," I thought to myself. It had taken me a long time going over scenarios and potential disasters in my head before I finally decided I could go through with this. It had always been a fantasy of mine to be an escort. I’ve always been fascinated with them and their lifestyle. And I’d watched enough documentaries on them that I knew what to do, and what not to do, ever. But I was still nervous as hell.

I couldn’t reply to the email yet, anyway. I had to line up an excuse to tell my husband first. As I drove home, I dreamed up stories in my head. Maybe my boss needed me to go view potential office space? Maybe my girlfriend was celebrating a promotion? I decided to go with a work function – some of the executives were coming into town, and I was expected to attend dinner and arrange entertainment afterwards. That would work – it was not unusual for work functions to happen on weekends, or for me to stay out late on weeknights with coworkers for drinks. When I walked in the door, I was greeted by my husband and little one, dinner already on the table. I mentioned the function coming up on the weekend, and my husband kissed me sweetly as he got up from the table clearing the plates, and said, “You are so dedicated. I hope they realize what an amazing employee you are." Later on, I replied to the email that I was available, and would be in touch on Saturday.

I started getting ready for the “date” early in the evening, sent my new client a confirmation, and told him to meet me at a wine bar in a trendy area just outside of the downtown core. As I left the house, he sent me another message. He said he lived just around the corner from the bar I’d chosen, and asked if I would mind meeting him at his place. As I got into the car with my driver, I asked his advice. He said to do it if I was comfortable, and he would wait just outside the door. I trusted him, as we had been very good friends and co workers for years. I’m sure he also wouldn’t mind sleeping with me. We’ve always been very flirty with each other and it didn’t take much convincing for him to agree to be my “muscle” and my driver.

So, I replied to the email that I’d be okay with meeting at his house, and that I hoped he had a bottle of Chardonnay chilling in the fridge. I decided I might be more comfortable on a sofa than in a bar anyway. Especially since this was my first time doing this.

He replied quickly with his address and as I read it, I gasped and froze. I had been there many times in the past. I was very familiar with the address, as it was my boss’s house. I had a decision to make, and quickly. Do I reply and tell him it was off and not give him any explanation, or show up at his house anyway? I chose the latter, but told my driver exactly what was going on.

He kind of laughed, and said, “Maybe this was meant to be. He’s been eyeing you up since day one.

'I scoffed – no way!' At least, I had never noticed it. Either way, shit was about to get real and I had to come up with a plan of action for when I walked through his door.

I started shaking as we pulled up to his house. I checked my makeup in the mirror, and slowly got out of the car. My knees almost gave out as I walked up the path, and I held my breath as I rang the doorbell and listened to his footsteps on the hardwood floor. The door opened, and there was my boss, dressed in jeans and a collared shirt – his usual dress code. His smile on his face quickly turned to a look of confusion.

“Uh, wha…what are you doing here?”

I breezed by him, noticing out of the corner of my eye the stack of crisp 100 bills on the console table. I turned around to face him and said, “I’m coming in for a glass of Chardonnay.”

As soon as the word “Chardonnay” passed my lips, his face dropped. He laughed nervously. “Well, come on in then," and he shut the door behind him.

I headed straight for the kitchen, and saw the open bottle of wine on the black granite counter, with 2 glasses beside it. The kitchen opened to the living room, and I sat down on the arm of the over sized sofa facing him as he poured the wine. I crossed my legs, so as not to reveal anything as I was wearing a fairly short wrap dress. Despite my efforts, one side fell open and my upper thigh was exposed. He turned to hand me a glass, and looked down at it, then quickly looked away. He was obviously a bit uncomfortable with this situation. I decided I had to say something to put him at ease. In the office, he and I have a great relationship – always joking back and forth, teasing each other about everything. Whenever we are at company events we usually end up in deep conversations in the corner, and my coworkers have asked me if there is anything going on between us.

I always scoff and say “Never!!” but the truth is, I had thought about it. Fantasized about it, even. But now that I was faced with this situation, I wasn’t sure I could go through with it. But, I decided that I had to remain professional as always so we at least had to have a conversation about it.

It had been quite some time since I’d been in his house at night – probably since the executive Christmas party last year. The charcoal walls, dark hardwood floors, and dim lighting created a very sultry atmosphere. There was a fire burning in the fireplace, and candles lit on the mantle. He had music playing, but not too loud. I felt at ease there, but he was pacing the floor in front of the fireplace. I had to break the awkward silence.

I took a deep breath. “Well, I’ll go first,” I said, not quite sure what I was going to come up with to ensure he still respected me as his assistant the next day.

“Obviously, this is a tricky situation for both of us. I have no intention of anyone ever finding out that I’m in this business, so you can rest assured your secret is safe with me. I know you, and know that you are a discreet guy, so I’m sure I can safely assume that you will also keep this to yourself.”

He took a long sip of his wine and nodded. He looked deep in thought, so I let him process what was going on and sat in silence. Finally he asked, “How did you even get into this? How many clients do you have?” He paused, and as I opened my mouth to answer, he added, “I have more questions but I’ll let you answer those first.”

I started to explain my interest in the industry, and how I started up my “business." I told him he was my first client, and he looked relieved. We continued chatting a bit, and as we did, we finished the bottle of wine. The mood was light, and we laughed and joked as we usually do. I didn’t feel any pressure, but there was never any discussion about his expectations of the evening. I assumed he didn’t want to go through with the original arrangement, but I started to think I was wrong when I smelled his cologne and felt his breath on the back of my neck as he leaned in to fill my glass from the second bottle of wine. I moved forward, a bit surprised and uncomfortable with the closeness.

We continued talking and drinking, and the next time he came over to refill my glass, I made a quick decision. As he leaned in to me, I leaned back. My shoulder rested on his chest, and I tilted my head up to look at him. He turned his head down to me and we made eye contact. I have never been this close to him, looking him right in the eye like this. My heart started pounding, and I started shaking. I could barely breathe. I certainly couldn’t move even if I wanted to. I didn’t know what to do next, or if I should do anything. My adrenaline was going crazy. How will this change our working relationship? How will he act at the office after this?

“Fuck it," I thought, and went for it. But just as I stood up and stepped in closer to him, he jerked back. “Oh shit, what have I done!” I thought to myself and mumbled an apology. This is not how I saw this evening going AT ALL.

Completely mortified, I excused myself and went to the washroom. I took a deep breathe, and decided that I would go back out and end the evening now before I made an even bigger ass of myself. Obviously, I can’t read signals and just suck at this.

As I came around the corner to the living room, I scanned the room for him but he wasn’t on the couch or in the kitchen. Just then, from the dark dining room to the left of the kitchen I felt a strong hand grab me by the wrist. He spun me around, and pulled me close to him. Without saying a word, he pressed his lips to mine and kissed me deeply. I immediately froze, but relaxed in to him as he held me tightly, my arms around his neck. I didn’t care how he acted the next day at the office, I wanted this.

I felt my knees start to weaken as we kissed.

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