tagAnal14 Memorable Anal Encounters 06

14 Memorable Anal Encounters 06


This story is dedicated to my best ever anal encounter. Not only was Cathleen the best anal lover she was by far the best sex partner I ever had. I 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 Cathleen 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 Cathleen 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. Cathleen 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 Cathleen'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. Cathleen was 5'6" tall with short blonde hair. She weighed about 125 pounds and she was very solid. Her legs were muscular but shapely and her ass was to die for. Cathleen was small breasted but I was never turned on by big tits so it didn't matter. At 36 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 40 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 Cathleen 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 Cathleen 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 Cathleen 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," Cathleen 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 Cathleen 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 Cathleen 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. "Cathleen, you have been a gem these past six months and I thank you for all your hard work and your loyalty."

Cathleen 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 Cathleen got into the driver's seat. We did not kiss again as I expected and Cathleen 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 7+" porker and then she lifted her head to speak again. "You have a nice cock," she said and then returned to sucking me.

Cathleen 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 Cathleen. 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. Cathleen 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. Cathleen'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. Cathleen 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.

Cathleen 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. Cathleen 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. Cathleen 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. Cathleen 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 Cathleen to drive home. We said goodnight but didn't kiss. I walked back to my car and then watched as Cathleen 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.


The next day Cathleen 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 Cathleen 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," Cathleen 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 Cathleen'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 Cathleen would be pleased with her review and promotion.

The next day I conducted Cathleen's review at 10:00 AM thinking that we could go to lunch afterward and celebrate her good news. Promptly at 10:00 AM Cathleen 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 Cathleen's performance review and my evaluation of her work. As I read through each category and began to explain my rationale for the rating, Cathleen 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 Cathleen 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. Cathleen 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.

Cathleen 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 threw my tie over my shoulder and watched as she lowered her mouth to my cock. Cathleen 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.

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

Cathleen, 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. Cathleen 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. Cathleen 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 Cathleen.

"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. Cathleen had a beautiful pussy with a little tuft of blonde 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.

Cathleen groaned when my mouth covered her cunt and then she emitted a squeal when I located her clit. Within minutes Cathleen 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. Cathleen was in a euphoric state and she glowed in her pleasure.

Cathleen 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.

Cathleen 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. Cathleen 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. Cathleen 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.

"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. Cathleen 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. Cathleen would then suck my cock until I came in her mouth.

We also revisited the bar near her place and after a burger and a few beers it was sex in her car again. Sometimes we fucked and sometimes she just sucked my cock while she fingered her pussy. She would unbuckle my belt, unbutton my trousers and pulled them along with my boxers down to my ankles. As Cathleen pulled my boxers down over my balls she would lick and suck them before kissing her way up my shaft. Looking up into my eyes, she would slide her lips over my bulging head with her hand still wrapped around my shaft. Her tongue would swirl under the ridge of my crown as she sucked me deeper into her mouth. She would test her gag line and take my cock down her throat.

She would pull 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 would have me on the verge of a huge orgasm. Cathleen would often slip her hand into her panties and finger her dripping pussy. The smell of sex would be rampant in her car.

When I felt my cock swell and I told her that she was about to receive my load. Muffled moans would escape from her throat as she eagerly sucked my dick awaiting my release. She would move her lips up and down over my shaft in rhythm with my thrusting motions. She would be drooling like crazy and I could feel the wetness running down my pecker onto my balls.

My breathing would become more erratic as I was about to lose control. Cathleen would look up at me with those big eyes and nodded her head, letting me know she wanted to taste me and then she would cover my cock with her mouth just as I lost it. I always let out a soft grunt as I pumped stream after stream of hot cream into her mouth. She would move her hand under my scrotum to squeeze out the last few drops and then Cathleen would have her orgasm. The feel of my throbbing cock in her mouth, the taste of my seed and her hand in her cunt was just enough to set her off. The pressure in her lower tummy would gush out through her pussy and soak her fingers.

My cock would fall from her lips and cum would drip from her lips and chin as her body would jerk and shudder in orgasm. Cathleen always 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 would take Cathleen's hand and licked her fingers clean. I would then pull my shorts and trousers back up and dress the best I could in the confines of her car.

One night when we were having a burger we discussed getting together in bed and being completely naked when we had sex. Cathleen didn't know it but I was very hot for her ass and I wanted a shot at it. She was married so we couldn't go to her place. I lived in an area where other corporate executives lived and I couldn't risk Cathleen being seen at my place. We discussed hotels and motels but I was leery of them as many of our vendors stayed at the ones near the office. That's when Cathleen suggested a romantic interlude motel called La Chateau.


On our first trip to La Chateau Cathleen arrived before me and parked her car in the private spot adjacent to the room. I had given her my credit card to pay for the room. I parked in the lot which was secluded from the road and walked to the room. Cathleen was already naked when I arrived. She told me that this was the only room available as the ones with the Jacuzzi tubs were all taken.

I looked around as I undressed and spotted the water bed, mirrors on the ceiling and walls. There was a TV with a porn station and a small mini bar in the room. Cathleen was naked in bed watching me as I undressed and I could tell that she liked what she saw. I liked what I saw too as it was the first time that we were completely naked together. I moved to the bed and 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 had 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 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.

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bywalterio© 4 comments/ 86382 views/ 56 favorites

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