Chicago - My Kind of Town

Afterward Catherine selected a couple of items form the catalog to replace her panty hose. That day at lunch time we went over to the Victoria's Secret store in the nearby mall and purchased nylons for her that had thigh high elastic tops. We also picked out some crotchless pantyhose that were very erotic. The panty hose had a waistband and two side panels attached to the stocking part. When Catherine wore the new pantyhose her ass and pussy were bare and her ass looked great framed in the hose. Catherine started wearing both the thigh high stockings and the crotch less pantyhose to the office along with sexy panties. It was very erotic when I slid my hands up her stocking covered legs to her bare skin just above the elastic tops. I would caress her bare skin before cupping and fondling her ass cheeks. Then I would remove her panties slowly dragging them down her legs and by the time I touched her pussy she was sopping wet. Catherine would move to the chair in my office and place her legs on my shoulders as I ate her pussy and fingered her asshole. She would have intense orgasms and coat my face with her pussy juice. Then we would finish with another one of her signature blow jobs.

We continued to have sex in the office, car and the romantic interlude hotel. We played games with each other taking turns being a slave and having to do what the other person demanded. There were times after aerobics that Catherine would come into my office and I would pull her spandex down just enough to bare her ass. I would fondle her ass and finger-fuck her pussy.

There was no shortage to our imagination and willingness to have sex in public as well as private places. Catherine, I was to learn, was somewhat of an exhibitionist. She loved to be totally naked in private places and was really turned on by the chances we took in public places. She loved it when I ran my hands under her skirt and inside her panties. She loved it when I pulled her spandex down to her knees and played with her buns and pubes. Catherine could never seem to get enough of my cock. She loved to fuck me, suck me and have me fuck her ass.

I was always concerned about the possibility of someone walking in on us even though the office door was locked. Staff from facilities and security had master keys and they could easily enter my office. It was one of the reasons we were never totally naked in the office. If someone did try to enter the office we could be dressed before the door opened. However, Catherine wanted to expand our office sex beyond oral sex and fingering. So I picked up a door brace at the hardware store and we used that to keep any intruders out.

Catherine would enter my office close and lock the door and then put the door brace in place. Then she would stand next to me and hold her skirt up while I pulled her panties down and off her body. She then moved to one of the chairs in my office and sat in it with her legs splayed and her pussy on display. I moved over to her, dropped my pants and undershorts and put my cock in her pussy. I fucked Catherine until she came several times. Sometimes I would cum in her pussy and other times I would fuck her ass. Catherine would kneel on the chair with her skirt thrown up over her back and her beautiful ass pointed at me. I took the lotion from my desk and lubed her asshole and my cock and then fucked her until I filled her ass with my seed. I kept paper towels in the office and we would both clean ourselves up and then get dressed.

Catherine loved our games and she loved to act as if it were the first time each time. She would stand by my desk acting innocent and awaiting my move. I slid my hand up her leg and I felt her tremble slightly as we had played this game before and she knew where it was going. I let my hand ride about and down her stocking covered leg for a few minutes. Then I let my hand wander above her knee and past the top of her elastic top hose. Catherine shivered as my hand touched the bare skin of her thigh. I caressed both of her thighs and I could tell that she was getting hot. The back of my hand brushed against her panty covered pussy and I could feel that the panties were soaked with her excitement. Catherine moved her legs wider apart causing the skirt to tighten around her shapely ass. I rubbed her inner thighs between her legs and flicked my fingers over the material covering her vulva. Catherine jumped involuntarily when she felt my hand on her pussy.

"Your panties are very wet Catherine. Would you like me to take your panties off you?" I teased her.

Catherine nodded and gasped, "Yes, please take my panties off."

I eased her panties down over her buttocks, past her thighs and then let them slide to her ankles. Catherine stepped out of them and I put them on my desk. I returned to fondling her ass and thighs and I soon had her squirming with desire. Catherine moved her body as if she were trying to get my hand near her pussy so I slid it between her legs and stroked the outer lips of her labia. Catherine squirmed under the touch an emitted a soft groan. I started to push Catherine's skirt up but she stopped me and then she took it off. It was a wrap around skirt and she had it off in an instant. She looked so sexy standing there leaning forward slightly on my desk. Her cute ass was framed by her thigh high hose and her short blouse ending at her waist line. She actually looked hotter by keeping the blouse on.

I ran my hands all over Catherine's ass, thighs and pubes feeling her wet pussy. I slipped my finger into her vagina and then added a second one. I took some lotion from my desk and I pushed a finger between the cheeks of her ass and massaged into her nether hole. Then I fingered Catherine's ass and pussy at the same time. She was going wild with the double penetration and cried out to me.

"That's it finger me, play with me. Make me cum, please make me cum," Catherine pleaded in a deep whisper.

I continued to work her ass and pussy and within minutes she had her first orgasm. Catherine held onto the desk with both hands as her body jerked and spasmed with her climax. I worked my fingers in and out of her holes as she clenched and relaxed her vaginal and anal muscles tightening herself on them. I pulled my fingers from her holes and I stood up behind her. I dropped my pants and boxers to my ankles and brought my rock hard cock to her buttocks. I let it rest against the hot flesh of her ass and I leaned over and whispered in her ear.

"Where do you want it first today? Do you want it in your ass or do you want me to fuck your pussy first?" I teased her and then licked her ear.

"Fuck my pussy first and then my ass. I want you to cum in my ass," Catherine murmured.

I then eased my cock into her pussy and fucked her from behind until Catherine orgasmed once again. Then I moved my cock to her ass and fucked her for a short time before I unloaded my semen in her anal canal. Catherine looked so hot leaning over the desk with my cock sliding in and out of her asshole that I just couldn't prolong my ejaculation any longer. I leaned over her and she milked my cock dry until it softened and popped out of her ass.

Our sexual encounters in the office usually ended up the same way, with me cumming in Catherine's ass but only after she had cum herself two or three times. Catherine would surprise me from time to time. One day she leaned over the desk and as I ran my hands up her legs I discovered that she had already removed her panties. Another time she just walked in and immediately took off her skirt and panties. Without her skirt and panties she looked very hot in just her hose and blouse. There seemed to be no end to her creativity and willingness to try new things. However she never showed interest in adding another person to our encounters.

THE SEMINAR

The seminar at Amelia Island was the first time that we stayed together for any longer than one evening and it was great having morning sex with her. It was Tuesday afternoon and I had three more nights and three more mornings of hot sex to look forward to with Catherine. I only stayed at the pool until 3:00 PM and then I returned to my room to shower. Catherine called from her room at 4:30 PM and I told her to come to my room. I was dressed only in my gym shorts when she arrived.

Catherine smiled and grabbed my cock through my shorts, "Miss me?" she teased.

"You know I did," I replied as I grabbed her ass through her slacks.

"Let's fuck before we go to dinner," she said as she began to disrobe.

In a matter of minutes after she arrived we were both naked in my bed and I was drilling her pussy. My cock was buried in her and I made sure that in stayed in contact with her clit. Catherine orgasmed quickly but we kept right on fucking as I knew that she would cum at least once more. She wrapped her legs and arms around me and held me tight as she humped my cock. Then she exploded with another orgasm and it was intense. She cried out and bit softly into my shoulder to stifle her screams.

"God that was great! Did you cum?" she gasped.

"No, I can wait though. Let's get some dinner and then we can play some more after we eat," I answered.

"Let's have room service," she suggested.

"Fine with me," I agreed.

We looked over the room service menu and made our selections. Catherine then got dressed and returned to her to change clothes while I called in our order. Catherine returned before the food arrived and we sat out on the balcony overlooking the ocean. Twenty minutes later the food was delivered and we dined on the balcony. I had ordered two bottles of wine as well knowing that it would be a long evening.

After we ate we relaxed on the balcony finishing the first bottle of wine. Catherine started getting frisky and she put her bare foot in my lap. Then she ran her foot over my stiffening cock as we drank our wine. I felt my cock harden under her foot but I made no moves to take the action further.

"Take your cock out," she told me.

I fished my cock out of my shorts and it stood up in an erect position. Catherine had slipped off her other shoe and then she placed her feet around my cock. She rubbed both feet together up and down my shaft. It was a very erotic act and I decided to let her have her fun. I felt my balls tighten as they normally did right before I ejaculated. At that very moment I decided to cum on her feet.

Catherine had a very wanton look on her face as she jerked me off with her feet. She was really getting into it and I decided to surprise her with my ejaculation. Then without warning cum spurted out of my cock shot straight up and landed on her feet and shins. Catherine giggled when I came but she went right on stroking my cock with her feet. She continued to rub my shaft with her feet squeezing cum from it.

Then she spoke softly, "I douched my pussy and my ass for you when I was in my room."

I knew exactly what she wanted without her asking, "So are you telling me that your bottom is squeaky clean and that you would like my tongue in there."

"Oh yes," she said excitedly.

We then left the balcony and headed to the bed stripping off our clothes. Catherine never bothered to wipe the semen from her feet. She was anxious to be rimmed again and I was ready and willing. Catherine got on the bed on all fours and wiggled her ass at me in anticipation. I got behind her and ran my hands all over her lovely buttocks and then pried them apart to expose her anus. I dipped my tongue between her cheeks and tickled her pink rosebud. I pushed my tongue into her taut anus and wondered how she could take my cock in there so easily. I licked Catherine from her anus to her pussy and she went wild. I kept that up until so orgasmed and collapsed face down on the bed.

Then I began to massage her body as she recovered. I used the body lotion supplied by the hotel and covered her back and shoulders with it. Then I worked my way down to her legs and massaged her calves and the back of her thighs. Next my hands covered her curvy buttocks and I massaged those glorious globes. I lifted Catherine by her hips and she kept her head on the mattress and turned her face to the side. She had a dreamy look on her face as I fondled her buttocks and began to finger her anus.

Satisfied that she was well lubed, I eased my cock into her ass and began to fuck her slowly. I was determined to take my time and last as long as I could. I loved watching my cock slide in and out of her shapely ass and I felt as if I could last for hours. I don't know how long I fucked her in her ass but by the time I ejaculated my thighs were burning. I fired several streams into her rectum and as she always did Catherine milked my cock with her sphincter muscles.

We were both exhausted so we moved into the spoon position and cuddled together. We fell asleep in that position and didn't move until morning. Then the insatiable rejuvenated Catherin was ready for morning sex. Once again I fucked her with my morning piss hard-on until she begged me to stop. Then after I relieved myself we fucked in the shower and I took her ass again. After the shower Catherine dressed and returned to her own room to get ready for the seminar.

It was a marathon as we had sex that evening, Thursday morning and evening and Friday morning before I left the hotel. I took an earlier flight on Friday then Catherine as she finished up with the seminar and returned later. That weekend I chilled out at my condo as I had had more sex in four days than I would have ever imagined. It had been an unbelievable week.

MOVING ON

Over a five year period the affair continued. We had sex frequently at least once and sometimes twice a week. I was recruited by a firm in California and accepted the position. Catherine elected to stay behind even though I offered her a position as my assistant with the California firm. We had a going away party on a Friday evening. After the party Catherine ended up back at my condo with me and for the first time in five years we had sex at my place. Catherine stayed through Sunday evening and we never left my condo. We had sex for two straight days and it was as if Catherine wanted me to never forget our final hours together.

I met some very pretty women in California and had sex with some gorgeous ladies. As good as it was in California I still remembered the times with Catherine. The sex with her was great but it was the risk and reward things that we did that made it exciting. I never had the opportunity for office sex again but I always recalled how erotic it was. I could still close my eyes and visualize Catherine standing next to me with my fingers in her pussy and ass. I would never forget those days.