tagAnalA Very Personal Assistant

A Very Personal Assistant



Coleen entered my office and sat in one of the chairs at the small conference table. It was time to conduct her performance review and I had the prepared documents on the table. I closed and locked the office door and then I put the door brace in place to guarantee that we would not be interrupted. I turned toward Coleen and she smiled at me knowing what was to come. I spelled out the approach for the morning.

"I have prepared your review papers and you can look at them any time and sign them. As you would expect I have given you an outstanding rating. There is no doubt that you are a very qualified Administrative Assistant and your work is impeccable. What I am going to discuss with you today is what else you bring to this position and the way you serve my needs. Before we begin I am going to remove your panties so that I can play with your pussy while we have this chat."

I moved my chair closer to Coleen and pushed her skirt up to her waist. I admired her shapely legs encased in thigh high hose with elastic tops and I recalled the day I took her shopping for them. I reached for her panties and pulled them slowly down her legs. She lifted her legs so that I could remove them and I place them on another chair. I ran my hand up her smooth skin above the hose and brushed her vagina. Coleen flinched when my hand made contact with her pussy and I found it to be sopping wet.

"You are wet already," I said as I dipped two fingers into her twat. I held the fingers to my nose and said, "You smell wonderful." Then I licked her juices from my fingers and said, "You taste even better."

I pushed my fingers back in her pussy, searched for and located her g-spot. With two fingers rubbing her g-spot and my thumb on her clit, Coleen raced toward her first orgasm. I would let her get close and then stop. Once she calmed, I began the masturbation again. She was going crazy and I loved teasing her.

"Now some of the skills that are not listed in the performance review should be discussed. Let's start with oral sex. Without a doubt you give better head than any other woman who has blown me. You are the best and most accomplished cock sucker of all time."

"Thank you!" Coleen replied with a blush.

"In terms of vaginal sex you are the best fuck I have ever had in my life." I began as I continued to work on her pussy. Coleen was dripping wet and she was soaking my fingers. "I love the way your body moves under me when we are in bed. I also love the way you ride my cock when we are seated in my office or the car."

"I appreciated you kind words," Coleen responded blushing again.

"I saved the best for last because there is no one who can compare to you when it comes to anal sex. You have the shapeliest, curviest, loveliest ass that I have ever fucked. I love caressing your smooth buttocks as I watch my cock slide in and out of your beautiful bottom. It is the biggest turn on for me and I am pleased that you like anal so much."

"I have to say something," Coleen offered, "I love your big cock. I love sucking it and having it in my pussy and ass. I love the feel of your seed shooting into my rectum."

"Thank you Coleen. That concludes the review now where would like it first today?"

"Are we going to the Chateau after work?"

"Yes, I planned on it and I already booked the room with a Jacuzzi."

"Wonderful, let's wait until tonight to do anal. I want you to fuck my pussy now but remember don't cum in me. I want you to cum in my mouth."

With that said I helped Coleen up on the conference table and spread her legs apart. Normally I would have eaten her pussy first but she was so ready that I dropped my pants and pushed my cock into her hot cunt. You moaned softly when I entered her and wrapped her legs around my torso. I fucked her slowly causing her to orgasm twice before I was ready to cum. I told her of my imminent ejaculation and she dropped to her knees to take my cock in her mouth. Coleen sucked me deep and I came in her mouth seconds after I entered it. Coleen drank down every drop as she always did and then we both cleaned up and straightened our clothes.

I removed the door brace and unlocked the door. Coleen left my office and as she did she said, "Thank you for a wonderful review."

I smiled and replied, "You deserve it."


I hired Coleen two years ago after my former assistant Bonnie got married and moved away. Bonnie had been my assistant for five years and the last three of those years we had a torrid affair. Bonnie was engaged to be married and I was surprised that she was so sexually active. I had always viewed the engagement period to be more sacred than marriage. It was not the case with Bonnie however.

Bonnie and I had sex in the office, in our cars and in a romantic interlude called the Chateau. Bonnie had introduced me to the Chateau. She had also been the reason I purchased the door brace for my office. The office door could be locked but facilities and security had master keys so I used the door brace to provide our security. It would have been very embarrassing if someone was to unlock the door and find me with my cock buried in Bonnie's ass.

Bonnie was a 30 year old sexpot when we began out affair. She was 5'6" tall, weighed a fit 125 pounds and had a respectable 33-26-36 figure. She was small breasted but she had a killer ass and she loved anal sex. Our times in the Chateau we would shower together first and douche her pussy and ass before entering the Jacuzzi. In the Jacuzzi I would play with her ass and pussy. She would lean over the edge and present her gorgeous ass to me to be kissed and rimmed. She loved having my tongue run up and down between the cheeks of her ass probing her anus.

As part of our foreplay I would lick her pussy and anus from behind and she would go wild. We then adjourned to the bed where I took good care of her pussy before I fucked her in the ass. We both loved anal sex and Bonnie was the best I ever had until Coleen.

It was nearly a year after I hired Coleen that we had our first encounter. It was totally unplanned and it just happened. It was after our corporate Christmas party when I gave Coleen a ride home. I had always found her attractive with her flowing long blonde hair and 36-28-36 figure. She had gorgeous legs, seemingly nice breasts and a very shapely ass. Coleen was 5'7" and weighed a trim 130 pounds.

At 31 years old I was in good shape from working out and my other activities which included golf, tennis, skiing and SCUBA diving. I was 6'0" and weighed a fit 185 pounds. I kept my light brown hair cut short and I had hazel colored eyes. Coleen loved my eyes and eventually told me that they were seductive.

Coleen had gotten a ride to work the day of the Christmas party from her older sister whom she lived with. I had promised to drive her home after the party. At the party we found ourselves dancing together several times. It started out with up beat music and then a few slow dances. The last couple of dances Coleen pressed her body in close and slipped her leg between mine. I was in an unmistakable state of desire and I knew she could feel my hardness on her thigh.

People had been drifting out for the last hour so when we got to my car in the parking lot no one was parked nearby. Before we got in the car, Coleen 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.

"Let's get in the car," she whispered.

We did not kiss again as I expected and Coleen 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 8" porker and then she lifted her head to speak again. "You have a nice cock," she said and then returned to sucking me.

Coleen 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 Coleen. 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. Coleen 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. Coleen'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. Coleen 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.

Coleen 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. Coleen 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. Coleen 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. Coleen 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 to drive Coleen home. I would have the weekend to think about what happened. My current live-in girlfriend Marty would be home Saturday and Sunday which I hoped would help me forget about the encounter with Coleen.


On Monday, Coleen 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 previous Friday night. 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. Coleen attended an aerobic class in the building next to our office and she would often return to work afterward since I let her leave work early the day of her class. That evening after her aerobic class Coleen 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 that Friday night before I would have never thought of doing that.

"Good night, see you tomorrow," Coleen said as she poked her head in my office.

"Oh, good night, don't forget that we are doing your first annual 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 Coleen's performance review. I gave her an outstanding review as she had been invaluable during her first year 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 Coleen would be pleased with her review and promotion.

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

Coleen 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. Coleen 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.

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

Coleen, however, as she had done Friday night in my 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. Coleen 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. Coleen 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 Coleen.

"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. Coleen 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.

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

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

We often visited a 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 Coleen 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. Coleen would often slip her hand into her panties and finger her dripping pussy. The smell of sex would be rampant in the 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.

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