Chicago - My Kind of Town

PRELUDE

I rolled over in the morning and bumped into another naked body in the same bed. I slowly recalled the marathon of sex the night before and then I realized that I had a raging piss hard-on. A soft hand embraced my stiff member and held it gently and I remembered that Catherine and I were in a hotel room together.

"Good morning sleepy head. Did I wear you out last night?" she whispered in my ear as she fondled my rigid tool.

I was still groggy as I had slept soundly and had some wild dreams. I yawned, stretched and made an attempt to get out of bed. "I have to pee," I told her.

"Not until I get to ride you. I'm going to take advantage of your condition this morning," Catherine remarked as she positioned herself to straddle my morning erection.

It was not the first time that Catherine and I had sex in a hotel room but it was the first time we ever stayed the night in a hotel. We had been having an affair for over two years and most of our sexual activity was conducted in my office although we did go to a romantic interlude motel at least once a week. Even though we were both divorced and single we did not live together. You see, Catherine was my secretary and administrative assistant. Our company had a strict policy about nepotism and inter-office romances.

I had sent Catherine to an Administrative Assistant / Secretarial seminar in Amelia Island, Florida. Then I took vacation days and stayed in the same hotel. We would be together for four days and three nights and I had just survived the first night. Now I was trying to survive the morning as she rode my piss hard-on. She was determined to orgasm as many times as she could that morning until she could not cum anymore.

"Don't pee in me," she teased as she rode my shaft like a woman possessed.

"Don't worry, that is not a possibility," I answered remembering how difficult it was to pee with an erection.

A few times in the morning I had to pee so bad that I tried but it wasn't until my penis softened to a semi-erect state that I could urinate. Even then it was difficult to control and I ended up missing the toilet with the first stream. I knew that my cock would stay hard as long as Catherine rode me and that I would not accidentally pee in her pussy. She rode me hard and at times I thought that my bladder would burst but it held out. Finally after a number of mild orgasms she climaxed and collapsed on top of me. I wrapped my arms around her body and held her tight as she bucked and screamed.

Catherine was always vocal when she orgasmed and often she would cum so hard that it was scary. I had gotten used to her orgasmic behavior and I loved to make her cum as much as I could. After a few minutes she rolled off of me and flopped over on her back.

"That was marvelous. We have to have more morning sex from now on," she sighed.

I rolled out of bed and made my way to the bathroom with my erect cock pointing the way. I stood over the toilet and tried to aim so that when I finally urinated that I would not miss the toilet. It took several painful minutes for my erection to soften enough so that I could pee and then finally success. It seemed like I peed for at least two minutes and the pressure was extreme. Then I washed my hands and my penis before returning to the bedroom. Catherine was waiting for me as she knew that I wanted to cum before she left the room for her seminar.

If we had more time that morning I would have fucked in her beautiful ass again. I loved anal sex and Catherine had one of the nicest asses that I ever fucked. However she need to shower, dress and get going so I settled, if you could call it that, for one of her signature blow jobs. Catherine was an accomplished cock sucker and I had been the recipient of countless blow jobs mostly in my office. However now were both naked in bed and I reclined on my back as she masterfully sucked my cock.

I gently caressed her long brown hair as her head bobbed up and down on my 8" dick. She would pause every so often and lower her mouth as far down as she could taking in most of my cock. Catherine loved to do the deep throat thing always testing her gag line. It wasn't long before her expert cock sucking, fondling my testicles and tickling my perineum that she had me spurting in her mouth. Catherine loved to swallow cum and she drank down every drop as ropes shot into her mouth. She kept me in her mouth until she had drained my shaft dry.

Catherine then became all business like and got ready for the seminar. She showered and dressed and then headed down to breakfast. "I'll see you around 4:00 PM," she said as she headed out of the room.

"I'll be by the pool," I told her.

"Behave," she teased.

"You enough woman for me," I called back to her as she shut the hotel room door.

I decided to go to the fitness center and work out before breakfast. After my workout I would shower, dress and go to breakfast. Then I would head to the pool and read the book that I had brought along. It was a book that I had been meaning to read and this would be a good week to do that. I knew that evening would be a repeat of the night before. First we would dine at a good restaurant and then we would have incredible sex back in the room.

That day as I sat by the pool I had a difficult time concentrating on the book that I was reading. First of all there were a number of hot looking girls in skimpy bikinis around the pool who got my attention. However the main reason was that I was thinking about Catherine and our two year affair. My mind drifted back to the start of our affair about two years ago.

HOW IT ALL STARTED

Two years earlier I, Cliff Watkins, was hired as a Senior VP to head up the IT division for a national firm headquartered in Chicago. I inherited the entire staff including the secretarial staff. Over the next six months I would make my assessments of the talent and capabilities of the staff before making any changes in personnel and restructuring the organization. During those six months I learned that my secretary Catherine was very capable and very loyal. She demonstrated that she could handle confidential and sensitive information. She was definitely a keeper.

During that time I didn't look at Catherine as a sex partner as she was not that pretty. Although not unpleasing to the eye she just wasn't the type that I usually went after. Still she was very fit and presented herself very well. She always dressed tastefully and professionally and conducted herself accordingly. Catherine participated in aerobics three days a week; Tuesday and Thursday evenings and Saturday mornings. Since we were so busy the first six months she would often return to the office after her aerobic class on Tuesday and Thursday to assist me. She would remain in her aerobic outfit and that was when I started paying attention to her very shapely ass.

It had been difficult to assess Catherine's figure when she was wearing her business clothes as she always wore long full dresses and skirts. However the first time I saw her in her aerobic outfit and the way the spandex hugged her curves, I appreciated her figure. Catherine was 5'6" tall with long brown hair. She weighed about 125 pounds and she was very solid. Her legs were muscular but shapely and her ass was to die for. Catherine was small breasted but I was never turned on by big tits so it didn't matter. At 28 years of age she looked good. I was 6'2" tall and weighed a fit 190 pounds. I was in excellent shape from my years of sports activities and frequent visits to the gym. At 32 years of age I was proud of my physique and fitness.

The day had come when it was time for me to present the Information Technology (IT) Strategic Plan to the senior management team along with my recommendations for organization change. Only Catherine and I knew what the organization changes were being recommended and how it would affect the staff. The presentation went extremely well and I received approval for the five year plan and budget. I also received permission to make the organization changes necessary to implement the five year strategic plan. That afternoon I held a town hall meeting with the IT staff and revealed the organization changes. I informed the staff that Catherine would be setting up a one on one appointment with me for many of them. That Wednesday evening I was still in the office when Catherine stopped in and asked if I was up for a drink.

"You look like you could use a drink," she observed.

"You're right! Do you know of a good spot I don't want to go to any of the local watering holes," I replied.

"There is a great bar near where I live that no one from the office goes to. They have great burgers too," she suggested.

"Sounds perfect, I am hungry too," I agreed.

"Why don't you follow me there but here's the address in case we get separated," Catherine offered as she wrote down the address.

We then left the office together and I followed her to the bar. She was right. It was a cozy place with great burgers. We discussed the day over a few beers and a burger and Catherine shared her feelings about the new organization structure. She alerted me to a few staff members who would take exception to the changes but I was already prepared for them. After we finished our beers we left the bar and walked out into the parking lot. I walked Catherine over to her car to be sure she was safe even thought it wasn't necessary.

When we got to her car I thanked her for all her hard work. "Catherine, you have been a gem these past six months and I thank you for all your hard work and your loyalty."

Catherine looked up at me and smiled. Her eyes twinkled in the street light and I had the urge to kiss her. I took her in my arms and kissed her tenderly. She kissed me back but it didn't last long.

"Sit with me in my car for a few minutes," she whispered.

I got into the passenger seat as Catherine got into the driver's seat. We did not kiss again as I expected and Catherine shocked me with her aggressiveness. She leaned across the seat and unbuckled my belt and unfastened my suit pants. Then she pulled my pants and boxer shorts down to my knees. I instinctively lifted my hips up to facilitate her. My cock was erect within seconds.

"I have wanted to do this for a long time," she whispered right before she engulfed my cock in her mouth.

Her head bobbed up and down a few times on my 8" porker and then she lifted her head to speak again. "You have a nice cock," she said and then returned to sucking me.

Catherine was very accomplished in oral sex and I was as hard as a rock. Then she stopped sucking and I watched as she reached under her full length skirt and removed her pantyhose and panties.

"I am really hot. I need to sit on your cock. I want to fuck you," she announced surprising me with her language.

I had heard women use the words cock and fuck before it was just that I had never heard it from Catherine. Then with catlike movements and agility, she straddled my body and guided my cock into her pussy. She groaned as my shaft filled her vaginal cavity and I felt the wet silkiness of her cunt. Catherine rode me hard and fast and it was obvious that she was only thinking about her own orgasm.

"Oh. Oh, this is going to be a quick one," she gasped.

I looked at the car windows to see if anyone was spying on us but the windows were steam covered and it was impossible to see in or out. We did make quite a sight though as we fucked in her car. I was still in my suit jacket, shirt and tie with my suit pants and boxer shorts down below my knees. Catherine's dress was gathered around her waist and I held on to her shapely ass while she did all the work.

"I'm going to cum. Hold me!" she called out excitedly as her hips flailed on top of me.

I held her by her curvy ass and then my arms moved up and wrapped around her upper body as she screamed into my shoulder. Her screams were muffled in my shoulder as her body shook and shivered with the intensity of her orgasm. Catherine eventually stopped moving and relaxed in my arms briefly before easing her body off of mine. She sensed that I had not cum and in her desire to pleasure me she lowered her mouth back onto my cock. It was obvious that she did not mind the taste of herself as she gave me an incredible blow job.

Catherine fondled my testicles and ran her finger along my perineum as she swirled her tongue around my shaft. I felt my discharge building within me and I warned her that I was about to cum. Catherine never removed her mouth from my cock and she received a mighty discharge. Ropes of semen shot into her mouth splashing off the back of her throat but she never missed a beat. Catherine stayed glued to my cock until she had sucked every last drop of semen from my shaft. Tingles ran through my body and I felt my toes curl up inside my shoes. It was the best blow job ever.

We relaxed for a few minutes and then got dressed the best we could. At least I did. Catherine opted to stuff her hose and panties in her purse. Then we opened the car windows and let the air in. I waited until the windows were clear and it was safe for Catherine to drive home. We said goodnight but didn't kiss. I walked back to my car and then watched as Catherine drove off. I then drove home all the while wondering where this would go. I had clearly crossed the line by having sex with a company employee and my secretary at that.

SEX IN THE OFFICE

On Thursday, Catherine arrived at the office on time and she went about her duties as normal. There was no mention of the car sex that we had the night before. She did not bring it up so I decided not to mention it either. We both went about the day in a business like manner. That evening after her aerobic class Catherine returned to the office wearing her snug spandex outfit. I observed her move around tidying up her desk and doing some filing before she left for home.

As I watched her I focused on her round curvy ass and I got a boner just from looking at her. It was all I could do to keep my hands off of her. I wanted to pull her into my office and pull her pants down and bare her ass. However I knew better and I restrained myself although it took all of my will power. If we hadn't had sex the night before I would have never thought of doing that.

"Good night, see you tomorrow," Catherine said as she poked her head in my office.

"Oh, good night, don't forget that we are doing your performance review tomorrow," I reminded her.

"I won't. I'm looking forward to it," she replied and then waved goodbye.

I returned to my work of finishing up Catherine's performance review. I gave her an outstanding review as she had been invaluable during my first six months on the job. I recommended that her position be raised one level and that she be given the title of Administrative Assistant. That would be consistent with the other Executive's former secretaries who all now held the title of Administrative Assistant. I was sure that Catherine would be pleased with her review and promotion.

The next day I conducted Catherine's review at 10:00 AM thinking that we could go to lunch afterward and celebrate her good news. Promptly at 10:00 AM Catherine was seated adjacent to me at the small conference table in my office. I had locked the office door so that we would not be disturbed.

I opened the booklet containing Catherine's performance review and my evaluation of her work. As I read through each category and began to explain my rationale for the rating, Catherine just stared at me the entire time. She seemed disinterested in what I had to say. About half way through the review she reached over and took my hand in hers. I stopped talking and looked into her dreamy eyes and sensed that she wanted something to happen.

"I know that you gave me an outstanding review and I appreciate that and the promotion. I want to show you how much I appreciate it," she whispered and added, "Stand up in front of me."

I stood up and remained still as Catherine unbuckled my belt and unfastened my suit pants. She took her time and then lowered my pants down past my knees. I could feel my cock rising to the occasion and my boxer shorts tented in evidence of my excitement. Catherine smiled as she reached for my cock and then she fondled it through the fabric of my boxers. I groaned as she gently squeezed my shaft. Then she slowly pulled my boxers down my legs allowing my stiff cock to get caught in the waist band. She continued pulling my shorts down until my cock cleared the waistband and bobbed in front of her face.

Catherine lowered my pants and shorts all the way to my ankles and then she pushed my dress shirt and tie up out of the way. I rolled up my shirt and through my tie over my shoulder and watched as she lowered her mouth to my cock. Catherine looked up at me as she moved her head up and down on my cock and the expression on her face was one of pure ecstasy. She gently held my balls in one hand as she worked her magic on my cock and I did not last long at all.

"Catherine, I'm going to cum," I whispered.

Catherine, however, as she had done Wednesday night in her car stayed glued to my cock. I exploded in her mouth with one of my most massive ejaculations ever. It seemed like I kept cumming for minutes although I knew it was over in a matter of seconds. Catherine sucked me dry again as she had done the first time. She kept my cock in her mouth for a seemingly long time after I came and she nibbled on it teasing me and driving me wild. I had tingles running through my body and I had to push her head away as I began to feel weak in my legs.

I steadied myself by holding onto the table and then I began to redress. Catherine smiled at me again and licked her lips in a very sexy way. I had pulled my shorts and pants back up and then I tucked my shirt back in and buckled my belt. I sat back down and smiled at Catherine.

"There isn't any provision for me to evaluate that skill on your appraisal form," I said jokingly and then added, "But if there was you would receive the highest grade possible."

"Forgive me but that made me very hot. I need to cum," she whispered as she lifted her skirt and pulled her pantyhose and panties down just below her pussy.

I looked at her neatly trimmed pussy for the first time and liked what I saw. Catherine had a beautiful pussy with a little tuft of brown hair just above it. I surprised her when I moved to my knees in front of her. Then I pulled her hose and panties down to her ankles. I did not remove them as I wanted her to be able to pull them back up if we were interrupted. I lifted her legs up and ducked my head under the hose and panties gathered around her ankles. Then I leaned in and placed my mouth on her pussy.

Catherine groaned when my mouth covered her cunt and then she emitted a squeal when I located her clit. Within minutes Catherine was cumming and juicing my mouth. She covered her mouth with her arm and moaned into the elbow joint stifling her outcry. I continued to lick her pussy as she thrashed around on the chair until she went limp. Then I kissed the inside of her thighs and eventually removed my mouth. I lifted her legs back over my head and then sat back in my chair. Catherine was in a euphoric state and she glowed in her pleasure.

Catherine then pulled her panties and hose back on and smoothed her dress as she stood up. She kissed me on the cheek and said softly, "That was an incredible performance review."

"It certainly was," I replied.

Catherine then left my office. It was the first of many office encounters. In the weeks to come, we had sex in my office and at times in the car. Catherine would give me marvelous blow jobs in my office. She loved to suck my cock and swallow my load. Sometimes we would play little games of seduction as if we were getting it on for the first time. Catherine would come into my office, close and lock the door and come around to my desk as if to show me something important. As she showed me some document I would let my hand move up her legs over her pantyhose up to her ass. I would fondle her ass for awhile and then lower her hose and panties to her knees. I played with her pussy as I fondled her ass and she squirmed on my hands and fingers.