My Dark and Twisty Mind (Part 2)

January 17, 2013

I realize it’s taken me way too long to continue this story about me working as an escort and my boss unknowingly hiring me.  I blame the holidays   Anyway…if you want to refresh your memory, here is part 1

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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.

Written by cheatingwhore Posted in Uncategorized Tagged with boss, butterflies, escort, fantasy, infidelity, wine