Office Sex is the Best

Author's note: This is a story about an office affair between a married man and a married woman. If infidelity, cheating and unfaithfulness upset you, please don't read this story. The story also contains anal sex and bisexual encounters which may not be to your liking. In the past I have received feedback that I should be upfront about the content of a story so that the reader is not caught off guard, which is why, I have explained the content of this story.

INTRODUCTION

In 1984 I had just completed a strategic information technology plan for a major corporation in the Chicago suburbs. I was working for a prominent consulting firm at the time where I was a senior manager. I had been working with the consulting firm for ten years and I was very close to being made a partner. Prior to the planning engagement I had traveled extensively for the firm and sometimes I was gone for months at a time. The traveling was getting old which is why I was receptive when the client CEO asked me to consider joining his company. He wanted me to take over the information technology division and implement the strategic plan that had just been approved by the board.

I knew why he made the offer. The IT division was a mess and there was serious doubt that the existing management could turn things around much less implement a new strategy. It was a lucrative offer as I would be a Senior VP and an officer of the company. The compensation package was loaded with incentives and it was very attractive. If I accepted I would be compensated just as well as if I was named partner with the consulting firm and I would not have to travel extensively.

I had a concern however that it might be perceived that the consulting firm would be viewed as sabotaging the existent IT management. The CEO agreed with me and we worked out a plan. First he would make the call on the existing IT management and then he would bring me in as an interim CIO to provide oversight. In six months he would then make me the offer of employment assuming that was what we both still wanted. So we proceeded with that approach and two weeks later I was brought in as the interim CIO.

The previous CIO had an administrative assistant named Cathleen who was nervous about the transition. I put her mind at ease and explained that she was not in danger of losing her job. Cathleen would function as my assistant for the next six months and if I was to accept the job, I could decide then if she was the right person to be my assistant.

The first six months were hectic in turning around a very difficult situation. I had to make many changes in management and staff. During this transition Cathleen proved herself to be very loyal and capable of handling confidential and sensitive information. I worked long hours and a 60-70 hour work week had become the norm. Then the CEO approached me again and told me the offer still stood. He said that I had impressed the rest of the executive team and that he wanted to bring me on board. I accepted the position and joined the firm.

In 1984 I was 43 years old, married with two children in college. I was 6'0" tall, weighed 190 pounds and I was very fit. I was an avid tennis player, golfer, skier, SCUBA diver and in a martial arts black belt program. Cathleen was 35 years old and married to a 40 year old man. She had short blond hair with a 34-25-35 figure. At 5'5" and 120 lbs. she was small breasted and her best asset was her ass. She was solidly built and exercised regularly and in excellent shape. Cathleen was not a beautiful girl but she was attractive and dressed very tastefully. She never wore tight fitting clothes or mini skirts so unless you saw Cathleen in her aerobic outfit you wouldn't see her figure. She took aerobics two nights a week at a studio that was on a different floor in our building. Aerobic class started at 5:00 PM so Cathleen would change at 4:30 PM and go to class. She would return to the office after aerobics and work until about 7:00 PM each Tuesday and Thursday. She remained in her leotards and it was then that I noticed her firm body and figure.

An Executive retreat was scheduled in November and I was on the agenda to provide an update on the IT turn around and objectives. Cathleen worked late with me preparing for the retreat and it was during that time that we seem to grow closer although nothing sexual had happened or was ever suggested between us. The retreat was at a plush Chicago hotel and on the second evening a cocktail party was scheduled. All the Executive's administrative assistants were invited to the cocktail party in recognition of their hard work.

The retreat was very successful and everyone liked my presentation and plans for the following year. After the second day of meetings it was time for the cocktail party. Everyone was in good spirits and enjoyed themselves at the social. The company dinner was held on the first night and on this night it was just cocktails and appetizers. Stations were set up for different types of food along with two bars in the small ballroom. Cathleen looked good that evening as she had worn a tasteful black one piece evening pantsuit.

Later in the evening I noticed that it was obvious that Cathleen had too much to drink. I followed her to the ladies room when I noticed that she staggered slightly. I waited until she came out of the ladies room and noticed that she still had trouble walking. She stumbled slightly and I caught her before she fell. Then I took her up to my room to let her sleep it off as she was in no condition to drive. I placed her on the bed and being worried about her getting sick; I removed her one piece black pantsuit. As I looked at her in her bra and panties I could not resist removing those as well. Her breasts were small and cute and she had a little tuft of blond hair above her pussy. She appeared to be passed out and I started to leave the room when she called out.

"Wait, don't leave me alone," she said softly in a somewhat slurred tone.

"I'll come back in a few minutes," I assured her and then I returned to the cocktail party.

I wasn't sure what I was going to do with her when I returned to my hotel room. I thought to call her husband but there was no answer at her home. Cathleen had told me that her husband often went out with people from work and he would often come home drunk. She also had shared with me that he was using coke now and that he was getting stoned a lot. So when he wasn't home I assumed that he would be useless to Cathleen that night. I put my thoughts aside and continued to socialize with the other executives until we called it a night.

I went back to my room and as I looked at Cathleen's nude form on the bed, I decided to join her. I knew I was crossing the line and I thought about that saying, "Don't dip your pen into the company ink," but I took off all of my clothes and approached the bed anyway.

THE ONE NIGHT STAND

As I knelt on the bed with my cock in a semi-erect state, Cathleen rolled toward me and said, "Oh, I am glad that you are back," and she surprised me by taking my cock into her mouth.

Within minutes she had me rock hard proving that she was an accomplished cock sucker. I was anxious to get at her ass all the while wondering if she would let me fuck her in the ass. I loved anal sex and fucking beautiful shapely asses. I always tested the water with the women with whom I went to bed. I moved her to all fours with her ass elevated and she placed her head on the mattress turned to one side so she could see me. I started playing with her pussy and her curvy ass lubricating her asshole with her own cunt juice. Cathleen moaned and cooed as I fingered her pussy and her asshole simultaneously. I tried to get her asshole wet enough with her juices and my saliva so that I could fuck her ass.

Cathleen had not objected to the ass play so I knelt behind her and tried to insert my cock in her ass but it just wouldn't go in. Afraid of hurting her I tried more pussy juice and saliva for lubrication but to no avail. My 8" long and 5" around cock just would not go into her tight ass. There are times when my cock feels bigger and this was one of those times. I was fingering Cathleen's ass when she spoke.

"Use some cream," she said urgently.

Well if there is one thing plush hotel rooms have is plenty of shampoo, conditioner and body lotion. I got off the bed to retrieve the lotion from the bathroom. As I did I realized that Cathleen was going to let me fuck her in the ass. I returned to the bed and put an ample of amount of lotion in her asshole coating the tiny puckered opening of her anus and lubricating the rim.

I added my saliva to my lotion covered cock and nestled my dick against the entrance of her anus momentarily before easing it inside her ass. I could feel my cock struggle to stretch the resistant muscles. My dick head burrowed in and her rigid passageway soon yielded to the determined action of my cock. Cathleen moaned as my penis filled her hole.

"Go slowly at first it has been awhile," she said sexily.

I fucked her with long and deliberate strokes until my cock was sliding easily in and out of her ass. I caressed her shapely buttocks as I watched my cock move in and out of her rectum worming around inside of her curvy ass. I caressed her small tits and tweaked her nipples as I leaned over her body and whispered in her ear, "Cathleen you have one hot ass, I love fucking you in your hot ass."

My hands freely roamed over her body and I pulled on her hips drawing her backwards impaling her on my inflated member. I reached for her pussy to finger fuck her and diddle her clit but I found Cathleen's hand already buried in her womb. She was frigging herself frantically working herself toward an orgasm. Suddenly I felt my cock inside her ass swell up and I started pumping faster. Within minutes I knew that Cathleen felt the warm fluid being squirted inside her anus and she immediately started to cum herself. Her cunt walls convulsed around her own hand fucking her cunt as her anal muscles squeezed every drop from my spurting cock. I grunted as my whole body became stiff and I slammed my cock harder into her. Cathleen writhed around and her body arched off the bed as a climax of massive proportion tore through her loins.

My cock slipped from her ass with an audible pop and I flopped down on the bed next to her. She surprised me when she covered my cock with her mouth and sucked any remaining cum from my tool. Cathleen then lay on her back, splayed her legs and pulled back the folds of her vagina.

"Here eat my pussy, please eat my pussy," she pleaded.

I rolled over and got between her legs. I put her thighs on my shoulders and lowered my mouth to her pussy. I took one slow lick as I flattened my tongue on Cathleen's mound. It felt so smooth and warm and I knew I had achieved the desired effect from her moan I know that Cathleen enjoyed it. I enjoyed the taste of her and I kept licking and eating her. I pointed my tongue and burrowed into her pussy as it parted her labia my tongue was rewarded with the exquisite taste of her juice. Soon having no reservation I was licking and lapping up as much as I could as fast as I could.

Cathleen was obviously enjoying what I was doing as she reached down with both hands and spread herself wide making it so much easier for my tongue to explore her pussy. Cathleen was breathing rapidly and she moaned softly whenever I got near her hard clit. As I searched out her hard clit still just barely hidden she tensed and began to quiver. After I felt like I had teased her opening as much as I could with my tongue it was time to see her reaction when my tongue finally touched that treasured pearl.

I burrowed my tongue as deep into her as I could and then I just sort of licked and sucked my way up. When I got to her clit I used the very tip of my tongue to push back the little hood. I was truly amazed at its size. I flicked my tongue over it once and then used the tip to explore the folds of flesh on either side of it. Cathleen was now moaning and she used her fingers to pull her hood back as she arched herself so that her clit stuck out even further like a little cock. I nuzzled it with my nose taking in her scent and I licked it once more before I took it between my teeth and gently nibbled it.

Cathleen went wild and started bucking and moaning loudly. She let go of her own fleshy hood and pulled my head to her pussy as she cried out in ecstasy. I sucked her clit as deep in my mouth as I could and Cathleen humped my face for all she was worth. I was excited that I was able to get her that excited and I sucked harder and played with her wonderful clit with my lips, tongue and teeth. I don't know exactly how many times Cathleen came but finally she collapsed on the bed, her body in spasms.

I lay next to her and stroked her body my hands moved freely over her tits and pussy mound. She rolled toward me and embraced me and yelled for me to hold her tight.

"Hold me, oh please hold me," she pleaded as her orgasm and spasms continued.

I had never seen anyone cum that hard before and I was briefly worried that she had injured herself. My fears were short lived when she finally calmed down and spoke to me.

"That was incredible I haven't cum like that in a long time. You really know how to eat pussy," she said with a sigh.

We lay there for awhile making small talk and then Cathleen started stroking my cock. Now at the age of 44 it was very unusual for me to cum more than once in a fuck session, particularly after having more than a few scotch on the rocks. In fact I usually could stay hard for a long time before my first cum which allowed me to pleasure my partner thoroughly before achieving my own orgasm. Cathleen added some body lotion as she kept stroking me cock and soon had me hard again.

"I like playing with your cock. You have a big cock," she told me.

"It's not that big," I replied although I was very comfortable with my manhood.

"It's bigger than Jerry's and the biggest I have ever had," she said with a sultry tone. I knew that Jerry was her husband.

"Well there are plenty bigger than mine," I assured her.

We continued our conversation as Cathleen continued to stroke my cock. I learned that she had first been ass fucked before she was married to Jerry. Cathleen was working downtown Chicago at the time and she went out with two guys from the office. They took her back to their place and one fucked her ass as she blew the other guy. She took to ass fucking after that but she was very selective about who allowed in her ass. Jerry did not like butt fucking and he also had lost interest in eating pussy, so now it was either blowing Jerry or occasional vaginal sex. She also told me that this was the first time she had sex with some other than Jerry since they were married.

I told her about my sex life too. My wife did not like oral or anal. She didn't even like to sit on my cock so with her it had been straight missionary sex for twenty plus years of marriage. I had had flings on the road when I traveled for business but up to now I never did when I was home. I loved women with great legs and shapely asses and anal sex was my favorite although I always made sure that the woman was pleasured.

"All this talk and playing with your cock has got me hot again. I need to sit on your dick," she announced.

Cathleen straddled my body and lowered herself onto me as she held my tool and aimed it at her vagina. My hard cock slid easily into her womb and she emitted a small gasp as it filled her hole. Cathleen rocked back and forth on top of me as I held on to her curvy ass. I stroked her ass cheeks and molded her firm buttocks in my hands as she picked up the pace fucking herself on my dick. Cathleen started moaning as she fucked faster and faster. I sensed her pending orgasm and then she yelled out.

"I am going to explode. Oh, Oh hold me, please hold me tight," she screamed.

Cathleen collapsed on top of me her body quivering from the intensity of her orgasm. I could feel her juices coating my cock as it remained buried in her womb. It took a few minutes for her to regain her composure and she just lay on me and cooed. Eventually she rolled off of me and lay on her back next to me. I let her stay in the room that night as I was still afraid to let her drive home alone.

The next morning I woke up first and looked at the Cathleen lying next to me in bed. It was hard to believe that I had fucked my admin assistant last night. She looked so angelic sleeping on her back with her cute firm tits poking up in the hair and her hot pussy on display. I eased her legs apart and lowered my mouth to her vulva. I teased her with my tongue until her pussy heated up and glistened with moisture. She started to stir and reached down to her pussy to find my head between her legs. She opened her legs wider giving me easier access to her luscious pussy.

I located her clit and brought a soft moan to her lips as I nibbled it gently. I then inserted a thick finger into her pussy and continued to tease her hard clit. Her pussy was getting wetter and wetter and she started to move her hips with a desire to cum. That was the signal that I was waiting for and I moved my body up and knelt between her legs. I lined up my erect cock with Cathleen's sopping wet cunt and eased it in. Her face tensed with the anticipation of my big cock filling her pussy. I loved to watch my cock slide into a hot pussy and see the expression on my lover's face as the cock spread her wider.

I fucked her slowly at first and then I began to pick up the pace. Soon I was pounding her pussy and fucking her into submission. Cathleen had orgasm after orgasm as I relentlessly fucked her. I just kept at her with my piss hard-on until she screamed and pleaded with me to stop. Cathleen's body convulsed in a mind blowing orgasm and then she went limp on the bed. I smiled to myself and eased my cock out of her well fucked pussy. I got up and went into the bathroom to relieve myself and take a shower.

As I was in the shower Cathleen came in and joined me. We soaped each other's bodies and my cock was rock hard at attention. She knew that I hadn't cum yet that morning so with a smile she dropped to her knees and took my cock in her mouth. She only took about five inches in her mouth and stroked the rest of it with her delicate hand.

"Let me know when you are about to cum. I want you to cum in my mouth," she told me.

I just nodded and told her that I was close. Cathleen kept sucking me and jerking me off until I put my hand on her head as a signal that I was close. She took me deeper in her mouth and jerked me off with her hand. Cum flew out of my cock and sprayed the back of her throat. She pulled my cock out and let my remaining cum splash against her tits and neck. The shower water washed the semen away as quickly as it hit her body. Several ropes of cum shot out of my cock she squeezed the remaining seed out then took my cock back in her mouth and sucked me dry.

Cathleen stood up, kissed me and then said, "Wow that was a good load."

We got out of the shower and dried off. Cathleen put on a robe supplied by the hotel as I got dressed. I left the room and told Cathleen to wait until about 10:00 AM before she left the room. I told her that the other admin assistants would most likely assume that she had slept off her hangover. I joined the other executives for a continental breakfast and then we wrapped up the retreat. The retreat went until 4:00 PM and after that I returned home.

The next day everyone returned to work and Cathleen and I went about business as if nothing ever happened between us. I wasn't sure if we would ever get together again. I assumed that we wouldn't and that it had been a case of both of us having too much to drink and letting our guard down. I was satisfied with the one night stand as it had been great sex. For the next several weeks Cathleen and I didn't even speak of the one-night stand.