The next morning dawned like those before it, except I felt this mash of total anxiety and deep relaxation racing back and forth across my lower abdomen.
As I stretched my body and awoke, I inched my fingers down across my belly to the tuft of public hair and ran my fingers down until they finally gripped and warmed themselves on my penis.
As I gently squeezed myself there in bed I started to go through the scenarios again, pumping and kneading myself with my fist. I remembered the first time with Anne, my boss, at the local advertising agency, of me sitting there, buck naked, slurping on her hot labia in the office. Then I flashed forward to her warm mouth sucking my hunkering dick the night before, drinking my cum, telling me I was well-hung and beautiful.
She also told me another interesting fact I recalled as I lay there masturbating myself before work. We'd be getting an intern and I was supposed to "train" her. After being given this assignment from my superior after a bout of deep oral sex, I thought that "train" had other connotations, but did it?
Anne said she was a 19 year old kid who wanted to get into advertising. Her name, I remembered, was "Allison." Almost automatically I envisioned her walking into the office. She would be wearing casual blue jeans and maybe a tank top (it was still early autumn) and she would have blue eyes and an auburn pony tail. Pulled back. Perfect for gripping and using as she descended on my organ - all at Anne's request, of course.
The idea of having a "hot young co-ed" promised to me really turned me on and so it wasn't long before my hips bucked and I shot off a dry load. I was still empty after the night with Anne. And soon I would have to face her again.
****
As I pulled my clothing on and headed towards work in my car I felt oddly at ease. I was listening to some pretty chill music and I had already emptied my tank, so I felt quite confident striding into the office to face Anne. But the first person I bumped into was Barbara, our really big superior. The one who had an office, but where it exactly was located I couldn't tell.
Barbara was medium height with curly chocolate brown hair. She was Italian or Greek American, and she had olive oil skin, that was aging healthily. She must have been about 46 or 47. She liked to wear small silver hoop earrings, and she always had her nails done. She also liked to wear a black sporty leather jacket, and curl her hair as she talked to an important customer. She was buxom and filled in nicely for a middle aged woman. If Anne was the brains behind our agency. Barbara was definitely the face and she had a face that I would do.
"Hi Peter, How are you?" she asked with a buoyant smile.
"Oh, I feel great, Barb," I shot back.
"Oh, I bet you do," Barbara replied with a bit of mischief. "I bet you do."
I paid no mind. I had no illusions that Anne would keep her lips sealed the night after they were so open and extended around my young dick. It was natural for her to flaunt her sexual prowess. I'm sure I would be telling my buds all the details once I got back to school.
"So what's up Barb?" I asked trying to get off the very sensitive topic.
"Well, today is the day you are promoted," she said. "You have an intern coming in at noon and I expect you are knowledgeable enough to show her the ropes, especially during a busy week like this week," Barbara said.
"So just remember to be polite. And be professional," Barbara said. Just then her hyperactive mobile phone acted up and rang. "Oh, I gotta take this," Barb said. "Talk to you later, Peter."
"Be professional. Bet you know." I know that it may be normal that the older ladies at the firm I worked at might share, but I kind of felt a little strange about figuring it out for myself in the parking lot. With the head honcho no less.
Shaking our conversation off I strode into the office, and then downstairs past Anne's office, where she sat there, her usual self, the computer screen light fogging up her glasses.
"Hi Peter," she said in a business-like way. "Today is the day Allison is coming in so I want you to put her an introductory folder together."
"OK Anne" I said, enjoying the thrilling game we were playing. "Where's the stuff for her folder?" I asked. "It's in the back" she replied. "I'll be back there in five minutes to give you some more feedback on it. Just go ahead on back."
I walked into the backroom and took a look at the documents lying on the table, which sort of chronicled what kind of menial tasks this poor girl would have to do under my supervision. Believe me it was going to be a boring internship for 19-year old Allison Co-Ed. She might even get so bored that she...
I heard the door close behind me.
"Hi Peter," said Anne. "Hi," I responded coldly.
"So you want to know about your new assignment?"
"Yes," I said, feeling more apprehensive.
I was bent halfway over the desk with the papers and Anne walked up slowly from behind, placing one of her hands on the small of my back, and the other hand around my waist, right above my belt.
"Well," Anne said, as she began to slowly massage me in these two sensitive places, "your assignment is named Allison."
"I know," I said sarcastically. I felt like James Bond as played by Sean Connery, simultaneously making love and trying to get more information out of this very potent adversary.
"And it is your job to train her," she said. She then started slipping her hand down below my belt, connecting with the tip of my warm and growing cock.
"Oooh," she said. "What have we here? I remember this thing," she said, undoing my belt buckle and button. Slowly she let my cock out of my pants and held it in her warm palm.
"This is the young cock I had in my mouth last night, isn't it?" she said gripping me tightly. Her other hand lowered from my back and clasped my balls, her finger nails gently scraping and playing with them. Something had come over Anne. She was much more direct and more empowered since she had gotten laid. I wonder what would happen if we kept hooking up, but the relaxing power of her hands soothed me of any hesitations I might've had.
Instead I stood there, bent over, being milked by my 50-something year old boss, preparing for the best.
"So...so what do you want me to do to *gulp* train Allison?" I asked nervously.
"I will send you an e-mail every Monday morning with a description of your duties. And I expect you to complete them," she said. "Then I will want you to file a report back with me by Friday to make sure everything has been completed on time."
"You have six weeks to train this girl," Anne said. "Don't disappoint me. Or her."
She stood up on her toes and pulled my mouth into hers and kissed me passionately. "Now," Anne said. "Put yourself together. She'll be here in two hours."
****
As I settled down to my desk to check my e-mail I anxiously opened my outlook inbox to see what my "duties" for this week were.
