An Affair to Remember

Many readers of my works have inquired about my affair with a secretary of mine from the past. I had not written about that experience but I did mention it in my writer profile. Since there has been sufficient interest I decided to write about it. This affair goes back in time to the years 1984 through 1989. It is a true story although I did embellish it a little.

Introduction

In 1984 I joined a large Midwestern healthcare company as a Senior Executive at the age of forty-four. I inherited the secretary from the previous person a woman executive who held that position. My secretary Cathy was 35 years old and married to a man of my age. 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. Cathy was not a beautiful girl but she was attractive and dressed very tastefully.

The first year of employment was hectic in turning around a very difficult situation. I had to make many changes in management and staff. During this transition Cathy proved herself to be very loyal and capable of handling confidential and sensitive information. After the turnaround and when I felt that things were now headed in the right direction, I decided to hold a management retreat off-site. Cathy helped me organize the retreat and it was held at the Indian Lakes resort for two days. I had finalized my management team with ten managers as direct reports. The meeting was designed to get the new team pumped up about the new direction and team building. After the first day's activities we had a cocktail social in my two-bedroom suite. I invited the other two department secretaries, Annette and Sandra to participate in the social gathering.

Everyone was in good spirits and as the social came to a close my staff with the exception of Cathy and two managers adjourned to their rooms. The four of us had a couple of more drinks and it was obvious that Cathy had drunk too much. At one point she had come out of the bathroom and staggered across the room. I caught her before she fell, picked her up and carried her into one of the bedrooms. I placed her on the bed and being worried about her getting sick; I removed her one piece black jumpsuit. 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 suite.

"She's out cold," I lied to Mike and Paul as I rejoined them to finish my drink.

"What are you going to do with her Walt," Paul asked?

"Well I'll let her sleep it off for awhile. I expect that she'll wake up and make it back to her room. If not I'll wake her in the morning. I am in the other bedroom so I don't have a problem if she crashes there." I replied.

The three of us finished our drinks with some more chit-chat. Mike and Paul said goodnight and headed for their rooms. I went in to check on Cathy and as I looked at her nude form on the bed, I decided to join her. I knew I was crossing the line but I took off all of my clothes and approached the bed.

The Affair Begins

As I knelt on the bed with my cock in a semi-erect state, Cathy rolled toward me and said, "Oh, I am glad that you are back," as she took 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 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. Cathy moaned and cooed as I fingered her pussy and her asshole simultaneously. I tired to get her asshole wet enough with her juices and my saliva so that I could fuck her ass.

I knelt behind her and tried to insert my cock in her ass but it just wouldn't go. Afraid of hurting her I tried more pussy juice and saliva for lubrication but to no avail. My cock is 7-8 inches long and about 5' around. There are times when it feels bigger and this was one of those times. I was fingering Cathy's ass when she spoke.

"Don't you have any cream," she asked.

Well if there is one thing resort rooms have is plenty of body lotion. I got off the bed to retrieve the lotion from the bathroom. As I did I realized that Cathy 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 rectum 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. Cathy 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 penis 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, "Cathy you have a hot ass, I love fucking you in your hot ass." My hands freely roamed her body and I pulled 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 Cathy'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 Cathy 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. Cathy 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. Cathy 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 Cathy's mound. It felt so smooth and warm and I knew I had achieved the desired effect from her moan I know that Cathy 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 I was like a puppy at a saucer of milk, licking and lapping up as much as I could as fast as I could.

Cathy 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. My tongue explored all of her as my mind took notes of what seemed to turn her on. Cathy was breathing rapidly and she moaned softly whenever I got near her hard pearl. 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 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 pearl 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. Cathy was now moaning and she used her fingers to pull her hood back as she arched herself so that her pearl 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.

Cathy 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 Cathy 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 Cathy came but finally she rolled off of me and 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 Cathy 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. Cathy 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 me manhood.

"It's bigger than Terry's and the biggest I have ever had," she said with a sultry tone.

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

We continued our conversation as Cathy continued to stroke my cock. I learned that she had first been ass fucked before she was married to Terry. Cathy was working in Washington, D.C. 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. Terry did not like butt fucking and he also had lost interest in eating pussy, so for them it was straight sex. She also told me that this was the first time she had sex with some other than Terry since they were married.

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

Cathy 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. Cathy 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 with my dick. Cathy 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.

Cathy 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 think I need to get going," she said as she got up to get dressed.

"Yes, we have a pretty full agenda tomorrow and we could both use a little sleep," I agreed.

The next day's meeting went fine well and we wrapped up the retreat. Cathy and I never even mentioned the previous night to each other. We all headed home for the weekend.

The following Monday we all returned to work. Cathy and I went about business as if nothing ever happened. I wasn't sure if we would ever get together again. I assumed that we wouldn't that it was a case of both of us having too much to drink and letting our guard down. For the next several weeks we didn't even speak of the one-night stand.

Cathy participated in aerobics held at our location on Tuesday and Thursday evenings. Often after aerobics she would come back to the office and finish up some administrative tasks. She would still be dressed in her leotards which showed off her firm legs and shapely ass. It took all my restraint not to touch her hot looking bubble butt.

Cathy came to me and asked if one night we could stay late and go through a large number of file cabinets. She told me we were running short of space but she did not want to throw anything out without checking with me. The best night for her would be either a Tuesday or Thursday after aerobics. I agreed and we set the date for the house cleaning.

The Affair Continues

The following Thursday after aerobics Cathy and I tackled the project of cleaning out the files. It was a huge task and took us several hours but we emptied about twenty file drawers. Most of the stuff was old marketing material that could be tossed. As we worked that evening it was hard for me to keep my eyes and hands off of Cathy's butt. I was tempted to risk it and touch her but I thought better of it. Cathy then surprised me.

"Will we ever do anything like Indian Lakes again? And don't tell me that you don't know what I am talking about," she challenged.

She caught me totally off guard and I replied, "I thought that may have been a case of both of us drinking too much and getting carried away. I would love to get together again if you are sure that is what you want."

We wrapped up our work and went over to the local tavern to get something to eat. The tavern was known for the best burgers in the area and was a little secluded. You had to know where it was located and the parking lot could not be seen from the street. Cathy and I had burgers and a couple of beers before calling it a night. During our meal we discussed how we could get together and the importance of being discreet.

After our meal I walked Cathy to her car and she asked me to get in for a minute. Well we there longer than a minute as she proceeded to give me a fantastic blow job. She unbuckled my belt, unbuttoned my trousers and pulled them along with my boxers down to my ankles. As Cathy pulled my boxers down over my balls she licked and sucked them before kissing her way up my shaft. Looking up into my eyes, she slid her lips over my bulging head with her hand still wrapped around my shaft. Her tongue swirled under the ridge of my crown as she sucked me deeper into her mouth. She tested her gag line and was soon taking my entire cock down her throat.

My cock was alive and my hot flesh pulsed against her lips. She pulled me deeper into her mouth, pressing her lips tightly against me and sucking hard. The feel of my hard cock sliding between her lips and over her tongue had me on the verge of a huge orgasm. Cathy had slipped her hand into her leotards and fingered her dripping pussy. The smell of sex was rampant in her car.

I grabbed the back of her head and started fucking her face. She was slurping and sucking as fast as she could. Cathy drooled as she tried to keep up with my thrusting motions. Her fingers dug into my thighs, moving her head as I pumped my cock in and out of her mouth.

I knew her pussy needed attention but I wasn't about to stop anything she was doing. I could sense that I was going to cum soon and I warned her but she just kept sucking me in anticipation of receiving a creamy treat.

I felt my cock swell and knew that she was about to receive my load. Muffled moans escaped from her throat as she eagerly sucked my dick awaiting her prize. She moved her lips up and down over my shaft in rhythm with my thrusting motions. She was drooling like crazy and I could feel it running down my pecker onto my balls.

My breathing became more erratic and I was about to lose control. Cathy looked up at me with those big eyes and nodded her head, letting him know she wanted to taste his cum and then covered my cock with her mouth just as I lost it. I let out a soft grunt as I pumped stream after stream of hot cream into her mouth.

I shot the first jet against the roof of her mouth then several more blasts of hot cum poured into her mouth. She moved her hand under my scrotum to squeeze out the last few drops and then Cathy had her orgasm. Apparently the feel of my throbbing cock in her mouth, the taste of my seed and her hand in her cunt was just too much. The pressure in her lower tummy gushed out through her pussy and soaked her fingers.

My cock fell from her lips and cum dripped from her lips and chin as her body jerked and shuddered in orgasm. Cathy looked up at me when she was done, blotches of cum glistened on her lips. The smell of pussy in the car was powerful. I took Cathy's hand and licked her fingers clean. I pulled my shorts and trousers back up and dressed the best I could in the confines of her car. We said good night and I went to my car feeling totally drained as I drove home.

That night started our torrid affair that lasted until the end of 1989 when I took another job in a different part of the country. Over the next several weeks we would get together on Tuesday and Thursday evenings after aerobics at a hotel. Typically the evening went like this; Cathy would suck my cock and I would eat her pussy, then I would fuck her pussy and finally her ass, cumming in her ass. We also brought sex into the office on days when we would not be meeting later at the hotel. Cathy 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. Cathy 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 always kept lubricant in my desk now and I would lube up her bottom and finger her ass. I played with her pussy as I fingered her ass and she squirmed on my hands and fingers.

"Yes, play with me. It feels so good. Make me cum, make me cum," she would repeat over and over.

And cum she did soaking my hand with her female juices. She had to cover her mouth to muffle her moans of ecstasy. Then after she composed herself she would have me stand up and she knelt in front of me. Cathy unbuckled my belt and lowered my pants to the floor. Then she slowly pulled my boxer shorts down my legs. She loved it when my erection got caught in the waistband of my boxers and my cock would spring forward as it cleared my shorts. Cathy would then suck my cock until I came in her mouth.

I decided that the pantyhose were inconvenient for office sex and I purchased nylons for her that had thigh high elastic tops. Cathy started wearing the thigh highs 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. I would remove her panties and by the time I touched her pussy she was sopping wet. Cathy 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.