tagAnalIf It's Wednesday It Must Be Anal

If It's Wednesday It Must Be Anal



It was 1979 and I was managing the western region office for a small privately held software company. Our office was based in the Chicago office near the O'Hare airport. Our sales team covered all states west of the Mississippi River and we had district offices in Dallas, San Francisco and Denver. There were six sales and two technical staff based in the Chicago office and they were always on the road on Wednesdays. Some of them would be gone Monday through Thursday and others Tuesday through Thursday or Friday but they were always out of the office on Wednesdays.

My secretary Susan and I had been having an affair for over a year. We had been very discreet and no one in the office suspected that we were intimate. Susan was 28 years old, 5'6" tall and weighed about 115 pounds. She had short brown hair, brown eyes and a slender figure. She was just about flat chested but she had long nipples that stood out when she was excited. Susan had a narrow waist, shapely legs and an absolute perfect ass. Her ass was her best asset and it seemed to reach out to be touched. It was so round and protruding it was as if it was attached to the rest of her body.

My name is Walt and I was 38 years old at the time. I kept myself in very good shape playing tennis, skiing, SCUBA diving and working out at the gym at least three days a week. I stood at 6'3" and weighed a fit 190 pounds. I was also pleased with my manhood as my penis when erect was just shy of eight inches long and measured five inches around. I had my share of flings with other girls in our company as well as some customers and I always made sure that the women were pleasured in our sexual encounters.


Every Wednesday Susan and I would engage in anal sex in the office. We had decided sometime ago to only have anal sex once a week and to do it in the office on Wednesday when we had the office to ourselves. There was something very erotic and exciting about anal sex with our clothes on in the office setting. On Mondays and Tuesdays, Susan would wear tight fitting mini skirts that showed off her great legs and fabulous ass. She would drive me wild walking around the office with her curvy ass under her tight skirt. As much as I wanted to fuck her on those days we had agreed to wait until Wednesday. Mondays and Tuesdays were foreplay leading up to our Wednesday encounter.

On Wednesdays Susan would come to the office dressed in a dress that was cut just above her knees. The skirt of the dress was full cut and flowed with her sensual movements. Under her dress she wore stockings held up with a garter belt and silk panties under her garters. At 10:00 AM like clock work, Susan would get up from her desk and tell me that she was going to the ladies room. That would be my signal to get things ready. I placed a hand towel, a tube of lubricant and a butt plug on my desk. When Susan returned to the office she would have douched her asshole making it squeaky clean.

Susan re-entered the office and locked the door. Then she smiled at me and sat back down at her desk. I got up from my chair and walked out of my office toward Susan. When I reached her desk I extended my hand for her to take. Susan looked at me quizzically as if she didn't know where this was going. I loved the way that she role played as if she had no idea that I was going to fuck her in the ass. Susan stood up and I led her into my office by the hand. I closed and locked my office door behind us and then I placed a door brace under the door handle to prevent any of the building personnel from entering. I didn't expect anyone but facilities and building services had master keys and it was just a pre-caution.

Susan acted nervous and unsure of the situation when I turned her toward my desk and told her to place her hands on the desk top. Susan leaned over and put her hands on the desk looking over her shoulder as if she was wondering what I had in mind. That's what I loved about Susan; as many times as we had done this she acted as if it was her first time. I lifted Susan's dress up and draped it over her back baring her stocking encased shapely legs and her panty covered curvy ass. I ran my hands over the bare skin between the tops of her stockings and her panties and smiled as goose bumps appeared on her skin. I loved running my hands over the tiny mounds of flesh that arose when Susan got excited.

I took a hold of her panties in both hands and slowly lowered them down baring her flawless ass. I pulled the panties down as far as they would go inside the garters. Susan gasped as her ass was bared and she once again looked apprehensively at me as if she was unsure of my next move. I caressed her bare bottom gently in my hands relishing the feel of the smooth firm buttocks. Then I knelt down behind Susan and lovingly placed kisses on her luscious ass. I kissed and then gently nibbled on the enticing ass flesh drawing moans and groans from Susan. I kissed my way to the center of her bottom and let my tongue dip into the crack of her ass.

Susan trembled and gasped when my tongue moved up and down her crack. I put both hands on her buttocks and gently pried them apart exposing her anus. I loved looking at her cute rosebud just before I probed it with my tongue. Susan let out a soft scream when my tongue touched her tight aperture and she shivered slightly. I began to lick Susan from her anus to her vagina and within minutes her pussy was soaking wet. Susan was breathing rapidly and moaning as I kissed, licked and probed her two love holes.

Then I stood up and retrieved the lubricant from my desk top and applied it to Susan's anal passage. Susan squirmed when she felt the cool lube enter her ass and the goose bumps returned on her bottom. Next I eased my finger into her ass and pushed it all the way in to the last knuckle. Susan's body went rigid momentarily as she adjusted to the anal penetration. I finger fucked her ass slowly and I felt the passage loosen up around my finger. I added my middle finger and ring finger to her pussy and then finger fucked both of her holes simultaneously.

"Oooh, agh," Susan moaned with pleasure.

I added more lube and then I took the butt plug from my desk and inserted it in her ass. Susan again groaned as the plug spread her anus and then disappeared in her rectum. Her sphincter instinctively closed around the rubber plug. I stood up and had Susan turn around to face me. Susan knelt down on the carpeted floor and pressed her buttocks against the front of my desk. Then she reached up and unzipped the fly to my trousers to free my throbbing erect cock. She fished my cock and balls out of my boxer shorts and trousers holding it her hand. Susan stared at my impressive member for a few seconds before she began to lick up and down the shaft. Then she covered my cock with her sensuous mouth.

"That's it babe, get my cock hard and wet for your ass," I whispered excitedly.

Susan had a talented mouth and it didn't take long to bring me to the height of desire. I lifted Susan back to a standing position and had her turn toward my desk again. I lifted up her skirt and placed it on her back as she leaned over my desk. Then I pulled the butt plug from her ass and we both heard the audible pop. Moving closer to Susan I let my cock brush against her buttocks and then positioned my cock head against her anus. With a gentle but firm steady push my cock spread her flower and the head disappeared in her asshole.

"Not too deep at first and then deeper," Susan reminded me placing her hand on my thigh.

Susan said that every time that we had anal sex even though I was always gentle with her. I slowly fucked her ass letting my cock go a little deeper each time. I was in no hurry to sink my cock all the way in her ass and I loved to watch it slide in and out between her beautiful hillocks. Susan groaned each time I went a little deeper but her groans were in pleasure not discomfort. My cock eventually slid all the way in and my pubic hair brushed against her buttocks. I held her lovely ass in my hands as I fucked it slowly never wanting it to end.

As much as I wanted to fuck her forever in this position I felt my release start to build. Susan was frantically rubbing her clit and fingering her pussy in search of her own orgasm. She would usually manage to have at least one orgasm before I ejaculated and that day was no different. Susan moaned out loud when she climaxed and her sphincter muscles tightened around my cock. Her body thrust up and down and she rolled her ass when she came. I held to her buttocks and picked up the pace fucking her. Then I felt my pending release.

I pulled my cock from Susan's ass and aimed it at her anus and buttocks. The first stream hit her right on her anus and then the subsequent streams landed on her back and buttocks. I then pushed my cock back in her ass and Susan milked the remaining cum from my cock. She handed me the towel and I wiped her back and buttocks clean as my cock softened in her rectum. My cock eventually slipped from her ass and I wiped it clean with the towel and then I wiped my seed from her anus.

Susan stood up and pulled her panties back up and smoothed out her skirt. I tucked my cock and balls back into my pants and zipped up my trousers. Susan smiled at me as I opened my office door and then she returned to her desk. I checked my watch and saw that it was almost noon and time for lunch.

"Where would you like to eat today?" I asked Susan.

"How about Carmella's, I'm in the mood for Italian," she replied.

"Carmella's it is," I agreed.

Susan and I left the office and dined at Carmella's restaurant. Our anal sex on Wednesday mornings was just part of our office routine. We followed the same ritual every Wednesday and we never tired of it. I always ejaculated on Susan's body and not in her as it was neater that way. Otherwise she would be sitting down with an asshole full of cum the rest of the day. The two of us had a leisurely lunch and then returned to the office about 2:00 PM.


On Mondays, Wednesdays and Fridays, Susan attended an aerobics class at 4:00 PM. The exercise facility was in the building next to the one our office was in. I always used the gym in the morning before the business day started but Susan liked the aerobic class. On Wednesdays after aerobics, Susan would return to the office as if she had some last minute things to do. She didn't change her clothes and her fabulous ass was outlined in her tight leotard outfit.

Susan moved around the office as if she was busy but she was really teasing me with her curvy ass. As I watched her I wondered how many guys in the gym got a hard on looking at her ass in those leotards. I finally had enough of looking at her curvy bottom and it was time to fuck her again. I called Susan in my office and secured the door as I had done in the morning. I sat in my chair and had Susan stand next to me facing away from me. I then took a hold of her leotard bottoms and slowly peeled them down to Susan's knees. I took my time as if I was unveiling a masterpiece and actually I was.

Susan's ass was a masterpiece. It was the finest ass I had ever seen and fucked. I played with her shapely buttocks and kissed her beautiful globes. Then I put the lube in her anus and finger fucked her ass once again. This time there would be no butt plug and no tongue probing. I stood up and I had Susan lean over the desk again. This time I lowered my pants and boxer shorts to my ankles and stepped up behind Susan. Once again I eased my cock into her ass and I began to fuck her slowly.

This time I would last longer since I had already cum once that day. I fucked Susan's ass with steady slow in and out strokes. I caressed her luscious buns as I watched my cock slide in and out. It was almost impossible to describe how beautiful she looked with my cock in her ass. Susan had her hand back in her pussy and she was groaning as another orgasm approached. Susan had two orgasms before I came. This time I stayed in her ass when I ejaculated. I could feel her sphincter muscles contract around my cock when I came in her ass. I continued to fuck Susan slowly and she continued to milk my cock dry until I softened and slipped from her ass.

This time Susan used the hand towel as a pad and pulled up her leotards over it. She liked driving home with her ass still full of cum. She told me that it was an erotic feeling and that when she got home she was so turned on that she used her dildo on her pussy. I pulled up my underwear and pants and then we both left the office. As I drove home I still had the vision of my cock sliding in and out of her beautiful ass.

Susan and I would get together over the weekend and we would have great sex together. It would be oral and vaginal sex as we would wait until Wednesday for another anal encounter. I loved having sex with Susan as she was a marvelous partner. She loved oral sex in a 69 position and she loved having her pussy drilled by my cock. However good our weekend sex was I still looked forward to every Wednesday and our anal encounter in the office.

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