Let's Play

Damien

Damien

I sat there in shock as Jessika walked away from me on the roof top. And not only because she left me with a massive hard on. But because I had never met anyone like her.

I've hired countless PA's and they were all the same. They fall for me fast and hard. And Jessika was right, I get bored of them easily and that's the end of their employment. The only reason none of them have spoken out to the public is because of the non disclosure agreement I have them sign as part of their on-boarding paperwork. Jessika has signed one too already. I'm not sure if she knows yet.

Jessika was insanely intuitive. Hardly anyone has figured me out so fast before. I mean, it's only her first day and we've probably only spoken for 15 minutes total, if that. And no one, I mean no one, has wanted to play along.

I leaned forward and smiled. She was a spit fire. Strong willed. A bad ass. And I loved it. I haven't had a challenge in a while and Jessika is definitely a challenge. I will win this game for sure but it'll be fun to see her try.

I finished my meal alone and called for house keeping to clean up the rest. When I got back downstairs I stared at Jessika the whole time to my office, hoping to get a reaction out of her. But I got nothing. She had a laser focus on her work and the business side of me was impressed. Before we had gone to lunch I saw that she even prepped my schedule for the next few weeks exactly how I liked it: meetings in the morning before lunch. PA's always screwed that one up.

The rest of the day flew by with endless amounts of emails and phone calls. By the time I found a good stopping point it was night time. Jessika had already left for the day. I knew because I saw her walking down the street from my window. I would have to arrange transportation for her from now on. A woman like her shouldn't be walking around Seattle alone.

My driver Henry took me to my mansion in Madison Park. Luckily the drive wasn't too bad that night. I opened my front door to see my two boxers, Moka and Bean, run towards me. "Hey babies." I said as I gave them both scratches. Moka and Bean are sister and brother, both rescued from a local shelter nearby. People can argue all day about how I dont have the capability to love. But it's probably because all my love is spent on my dogs. The rest of my pack, Emma a german shepherd, Lucy a golden retriever, and Sasha a chihuahua came running shortly after.

"Mrs. William's how was the pack today?" I asked. Mrs. William's was married to my driver Henry and have been with me for over 10 years. She takes care of the house and my dogs while I'm away at work. They were practically the only "family" I had left now.

"Perfect little angels but you already knew that. Is there anything else you need from me Mr. Hart?"

"How many times must I ask you to call me Damien?"

"I guess for the rest of your life Mr. Hart." She walked over to me and patted me on the cheek. Anyone else I would've taken this as an insult. But Mrs. William's was almost like a mother to me. She was in her 60s and had graying hair. She walked with a bit of a limp and no matter how hard I tried to take her to a doctor she always shrugged it off as "old age".

Mrs. William's left with Henry and I headed to the shower. I stepped in and let the scolding hot water cascade down my shoulders. All of a sudden, the thought of Jessika came to mind. The way she climbed on to my lap, the way her hand closed around my neck, the way she rode my fingers and took charge, the way she came and made me taste her on my fingers...

I looked down at my growing erection. God dammit. I've already been left hanging once today and I cant do that again.

I started picturing Jessika, in a room on the 40th floor. The floor she was so curious about. I started stroking myself as I layed her over a bench and entered her, slowly. God, how I wanted to be inside her. I pictured the face she made as she moaned, lips slighty parted and eyes squeezed shut. I pounded into her, roughly. I made sure she felt every inch of me. I pictured her legs wrapping around my waist as I entered her repeatedly. She screamed my name as she came and I came with her, emptying my seed inside of her.

I opened my eyes and entered back in to reality. My cum was all over my shower wall instead of inside Jessika and I cursed at myself. I shouldn't have imagined her but I couldn't help myself. It looks like I was going to show her what was on the 40th floor. I wont lie when I say a part of me was excited...

Jessika

I sunk into couch, exhausted after a long, and interesting, first day. Our couch was old and I'm pretty sure I could feel a spring poking my ass but at this moment I couldn't care less.

"Honestly, I cant say for sure she's the one, Jess" Kat said as she sat down next to me with a bottle of wine, talking about her date from today. "She's new to the LGBTQ community which is fine but it also means I have to teach her how to, you know, do the nasty" Kat said, taking a swig of wine straight from the bottle.

I grabbed the bottle from her and took a drink myself. "Oh c'mon Kat. If you really liked her that wouldn't matter. And besides, you've taught women before, why is this any different."

"Because, Jess. Sometimes I just want my pussy to get rocked without me having to ask" Kat huffed as she crossed her arms over her chest.

"You're being ridiculous! No matter who you have sex with you're going to have to teach each other things. No one is going to know exactly how to please you without a little trial and error. I think you didnt have a connection with her and you just dont want to admit it" I said. Honestly, I was glad the conversation was about her and not about me. I wasn't ready to share that my boss made me cum on my first day.

"I hate you." She said, snatching the bottle back again.

"You only hate me because I'm right. And besides" I said as I leaned towards her. I placed my hand over her pussy and began to apply pressure. "You can always ask me if you need to release all that tension."

Kat sighed and leaned back. After a second, though, she smacked my hand away. "You're my best friend and I appreciate that you'd do that for me but we agreed that we were done. "

Kat and I had known each other since high school. When Kat first thought she might be gay in the 10th grade, her and I started trying things with each other, sexually. I've known I was bisexual since I was 12 but Kat came from a conservative family and was really shy about the whole thing. I wanted her to feel comfortable about her sexuality, being her best friend and all.

Technically I was her first, well, everything. I didnt think much of it but after a few years Kat admitted to me that she had feelings for me that were more than just friendly. She wanted to stop having sex and keep our friendship and I, of course, agreed. Hell, we live with each other now and if that didnt point to how close we were I dont know what would.

"Well you know I'm always here if you need me". I stood up and stretched out my aching limbs. All the walking and the buses really do a number on you. "I'm gonna take a shower now and go to bed. I need to make sure I'm well rested for tomorrow" as i turned to go, Kat grabbed my hand.

"I'm so sorry babes I didn't even ask how your first day was!"

I gave her a small smile. I dont know when I'll be able to talk about what happened but it definitely wasnt now. "It went great honey buns. Exactly what I'd hoped it would be".

As I walked away I couldn't help but feel a little guilty. I couldn't stand lying to Kat. But I guess it wasnt really lying. It was just withholding the truth, right?