I knew hiring Jessica was going to be trouble, but at the time I didn't know quite how much trouble!
Hiring a sexy 25 year old admin when you are a 40-something old guy like me could be seen as crazy or smart depending on your perspective. Jess was curvy in a way that made my whole body sit up and take notice. Her dark, Latina eyes seemed to bubble over with a bright youthful confidence untainted by worldly disappointment.
The first 3 weeks were actually rather unremarkable. Until one evening I asked her to work late with me to finish a project. It was nearly 10 pm and we were both exhausted mentally and physically. We had ordered in and the smell of stale Papa John's mingled with our sweat. I had to take a piss and as I went out of my office, I asked Jess to copy the draft on my computer onto her flash drive. The file was too big to email...in hindsight I should have used the office intranet.
When I got back from the men's room, Jess had a funny look on her face. I had a cold sweat and thought "OH SHIT!" I knew what the problem was. I had a porn site running in one window of my desk top. I didn't say anything. But it was a nasty anal sex site and I was pretty sure she had seen it. We finished for the evening shortly after that and I didn't ask her to work late the next night.
I did notice that Jess started to dress more provocatively though. She began really pushing the office dress code in more ways than one. She showed her nice C-cup breasts, went braless, and started wearing shorter and shorter skirts. She seemed to enjoy finding excuses to bend over within sight so I could catch her breasts bared or enjoy the view of her posterior.
One Monday afternoon I was working in my office with the door closed. She came in, closed the door, and asked if she could show me something she had been working on. She took out her flash drive and began fumbling putting it in the drive. She dropped it and bent over to get it off the floor. I looked and her bare ass was staring me in the face. She seemed to be having a really hard time picking the flash drive off the floor. "Darn!" she said softly. My heart was pounding and my erection strained against my trousers. "Holy hell!" I thought.
She finally got the flash drive off the floor but not before I saw her little brown anus open in front of my face.
She looked me in the eye and said simply "Mondays- you look." She smiled and walked out. I was in shock.
The next day, at 3 pm Jess came in, closed the door, walked around behind my chair, leaned over and whispered in my right ear "Tuesdays- you sniff." She came around in front of me, bent over and showed me her bare ass. She took a firm, round cheek in each of her hands and opened her bottom for me. I leaned in and inhaled the beautiful aroma of her brown bottom. It really stunk but in the sexiest, most delicious way possible. She let me inhale her for 5 minutes and then stood up, turned around smiled at me and walked out.
The following day, Jess came in right at 3, closed the door and again came behind me chair and whispered "Wednesdays- you lick". She bent over and opened her bottom for me again. My heart was pounding like crazy and I dutifully leaned in, drunk with the smell of her ass. I licked her stinky, sharp-smelling anus. For five minutes I had the absolute heaven of eating her before she stood up and walked out, pleased with herself.
The next day she came in at 3 and whispered "Thursdays- you finger me". She bent over and I lubed a finger with spit and put it inside her hot, stinky bottom. I gently fingered her asshole for 5 minutes before she stood up and walked out. I had a very stinky and delicious finger that smelled of her. I masturbated several times that evening holding the finger up to my nose.
The next day she came in at 3 and whispered "Fridays- you fuck." I couldn't wait. I had thought of nothing but putting it in her ass all week. I unzipped and took myself out. She produced a small tube of lube and a condom and bent over. It took a while to get into her ass, but it was worth it. Once I was in, I came almost immediately and Jess stood up, took the condom and walked out. She gave me one last smile before closing the door.
All weekend, I thought of her. I thought of emailing her, but I would never be stupid enough to use the office email and I didn't have any other account for her. I wanted to call her, but hesitated.
Monday seemed to drag until 3. Then Jess came in my office with a big grin on her face. She closed the door and whispered "Mondays you look". She bent over and showed me her ass. I started to undo my pants. Jess stood up quickly. "No!" she said with a angry look. "You have to follow the rules! Mondays you look!"
"But, Jess- I've been thinking about your ass all weekend. Show some mercy here.... I am about to explode. C'mon..."
"No. I am tellilng you no. Don't push me on this. Mondays you look. That's all." She must have seen the crushing disappointment in my face because then she added "I promise it will be worth the wait!"
I didn't need convincing. She bent over and I stared at her anus. She didn't know it but I could smell it too. I leaned a little too close to her, though and she said "Mondays you look!" After 5 minutes, she stood up and walked out.
So Mondays I looked, Tuesdays I could sniff her, Wednesdays I got to eat her, Thursdays I fingered her asshole and Fridays I fucked her up the ass. I got a lot better at fucking her asshole. I could get in quickly and after a few weeks I was fucking her ass nearly the full 5 minutes before Jess stood up and walked out. I was able to learn to hold back until the 5 minutes were nearly up and then shoot a huge load into the condom. Each time, she took the condom and walked out.
Things went on like this for some time with nearly unbearable tension. At other times (other than 3 o'clock) Jess remained friendly and a little provocative. Her job performance was fine. But weekends were hell. Not to mention the days waiting to fuck her ass again. Finally I had had enough. I called Jess on Saturday and asked to see her.
"No." she said simply. "Only at work."
"Jess, I can't stand this. Either I see you right now and fuck you up the ass or this is over. I will never look at, sniff, lick, finger or fuck your asshole again."
"Don't even think of threatening me," Jess said in a quiet, completely possessed tone. "I've saved your semen from the condoms and have some rubbed into one of my old skirts. I have the rest on ice in the freezer in case of need. I'll tell you how this is going to go. You are going to just keep doing what I tell you, every day at 3. You are going to look at, sniff, lick, finger and fuck my anus until I tell you to stop. If you don't do as I say, I will tell your boss you sexually harassed me and showed me your dick and masturbated in front of me and got cum on my skirt."
Jessica paused. I didn't know what to say.
"Is that clear?" she asked.
"Yes," I whispered.
She still has me by the short and curlies. I do exactly as she tells me. Every day at 3 she lifts her skirt and shows me her ass. And every day I do as I am told by my secretary. Her ass smells just as sexy as the first time I smelled it. I still love her taste. And I am dying inside every moment I am not enjoying her ass.