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A Very Personal Assistant

Category: Anal Sex
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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.

My breathing would become more erratic as I was about to lose control. Coleen 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 Coleen 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. Coleen 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 Coleen’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. Coleen didn’t know it but I was very hot for her ass and I wanted a shot at it. She lived with her sister so we couldn’t go to her place. I lived with my girlfriend Marty who was a flight attendant. Marty had the international route and even though she was gone for days at a time, I couldn’t risk having someone see Coleen enter my condo. I suggested the Chateau and Coleen agreed. She was curious as to how I knew about it but I never told her about Bonnie. I told her that Marty and I went there once for fun.


Her first trip to the Chateau Coleen arrived before me and parked her car in the private spot adjacent to the room. I had paid for the room in advance. I parked in the lot which was secluded from the road and walked to the room. Coleen was already naked when I arrived. She told me that the rooms with the Jacuzzi tubs were all taken. I was disappointed but made the most of it.

I looked around as I undressed at the familiar surroundings, water bed, mirrors on the ceiling and walls. There was a TV with a porn station and a small mini bar in the room. Coleen 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 was particularly hopeful that Coleen was into anal since Marty was not and I missed it desperately. 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. Coleen 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.

Coleen 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 Coleen’s ass when she spoke.

“Use some cream,” she said urgently, “There is some in my purse.”

I got off the bed and retrieved the body lotion from her purse. As I did I realized that Coleen 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. Coleen moaned as my pecker 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 ample tits and tweaked her nipples as I leaned over her body and whispered in her ear, “Coleen 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 Coleen’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 Coleen 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. Coleen 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. Coleen then lay on her back, splayed her legs and pulled back the folds of her vagina.

“I need to cum again. 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 Coleen’s mound. It felt so smooth and warm and I knew I had achieved the desired effect from her moan I know that Coleen enjoyed it. I always 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.

Coleen 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. Coleen 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 flicked my tongue over it once and then used the tip to explore the folds of flesh on either side of it. Coleen 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.

Coleen 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 Coleen 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 Coleen 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.

Once she calmed down, we lay there for awhile making small talk and then Coleen started stroking my cock. Coleen 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 the biggest I have ever had,” she said with a sultry tone.

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

“If I had a cock I would be playing with it all the time,” she giggled.

We continued our conversation as Coleen continued to stroke my cock. I learned that she had first been ass fucked before she was married and divorced. Coleen had been 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. I shared with her my love for anal sex and some of my encounters.

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

Coleen 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. Coleen 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. Coleen 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.

Coleen 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 was still hard so I took her ass again and fucked her until I released my second load into her rectum. After that we showered dressed and left the motel.

A week later we revisited La Chateau again and this time we had gotten a room with the Jacuzzi tub. We entered the room and wasted no time taking off our clothes as the Jacuzzi filled with hot water and bath gel. Coleen and I showered together before entering the Jacuzzi. We soaped each other up and played with each other’s bodies being careful we didn’t cum in the shower. Coleen then douched both her pussy and her asshole.

After showering we entered the Jacuzzi armed with a bottle of wine. I turned on the jets and we kicked back enjoying the bubbles and our first glass of wine. After awhile Coleen leaned back into me and I reached around and stroked her firm titties tweaking and rolling her nipples in my fingers. I slid one of my hands down across her firm abs over her little tuft of hair and found her vagina. I played with the folds of her labia and then inserted my fingers in her pussy. I found her hard clit and rolled it between my fingers as I continued to tease her nipples with my other hand.

As Coleen got turned on I moved her to the other side of the Jacuzzi and I had her lean over the edge presenting her shapely ass to me. Her ass always looked good but this time it glistened with water and bath gel and looked so sensual. I leaned over and licked Coleen’s pussy from behind driving her wild. Then I had the urge to tongue her beautiful ass so I swiped my tongue from her pussy up and over her bung hole and back to her pussy. She gasped out loud when my tongue touched her asshole. I really got into it and grasped both of her curvy ass cheeks and pulled them slightly apart so that I could get my tongue in deeper. I probed her pink aperture with my tongue as I inserted three fingers in her pussy. She started whimpering, gasping and directing the action.

“Oh my God, do it again. Lick my asshole; stick your tongue in there. Eat my pussy, tongue my ass, oh yessssss,” she cried out.

I grabbed the bottle of wine and poured some in the crack of her ass letting it trickle down over her anus and pussy. I placed my mouth on her and drank up the wine swabbing her pussy and ass in the process. I repeated this several more times until Coleen seemed to go into convulsions with her first orgasm of the evening. She collapsed back into my arms and I stroked her smallish tits as she recovered from the intensity of her orgasm.

“Not in my wildest dreams did I ever think that you would ever tongue my ass or did I know it would feel so wonderful,” she uttered in an exhaustive voice.

“I loved doing it,” I told her.

We decided to get out of the Jacuzzi before we turned into prunes. We dried off and flopped down on the water bed. Coleen began to stroke my cock into an erect state and then proceeded to suck on it. She loved to stick her tongue in the little hole and nibble on my cock head. This always made her hot and then she needed my cock in her pussy. She straddled me and aimed my cock in her hole and rode me until she achieved another orgasm.

It was time for me to fuck her in the ass so I had her kneel on all fours with her gorgeous ass in the air. She always put her head on the mattress and turned to the side so that she could watch. She had the added benefit of mirrors on the wall and ceiling and so could clearly see the penetration. I broke out the lube and put an ample amount in her asshole. I fingered her ass and pussy at the same time.

“I love the feel of your fingers in my ass and pussy together,” Coleen exclaimed!

If there was one thing I liked besides fucking a beautiful ass it is preparing an asshole for a good reaming. After several minutes of finger fucking her pussy and asshole I couldn’t wait any longer and I had to get my cock in her beautiful ass. I removed my fingers and lined up the head of my cock at her moist puckered ring and pressed forward slowly. My cock head strained to pop through and she let out a little groan as the pressure from my iron hard dick forced her little ring to open like a flower and suddenly my large mushroom head slipped past the ring and into her ass. Coleen let out a groan as her rear passage was stretched to accommodate my ample girth.

“Oh you are going to make me like this more than the regular way,” she gasped and shivered as I filled her fully and withdrew my penis slightly.

I felt her ass tighten around me and I continued to slowly stroke in and out of her tight ass until all eight inches were tightly packed up her ass. Coleen really began to moan and her whole body shook in anticipation of what she knew was coming. I began to slowly fuck her but soon picked up the pace as I penetrated her with long hard strokes that used the entire length of my thick cock. Coleen was going wild as she loved the feel of my cock as it pulled out and then came crashing back in as my big heavy balls bounced off her clit. Coleen was thrashing around uncontrollably, gasping and moaning with pleasure. When I reached underneath her to stroke her clit she exploded with her third orgasm of the night.

I continued to hammer her ass with long strokes then suddenly I felt that familiar tension in my balls and I knew I was close. I began to piston my raging cock harder into her searing ass in search for my release, which also increased the intensity of her orgasm. She was yelling and moaning, clawing and scratching at the cover of the waterbed begging me to cum.

“Give it to me, give it to me, give me your cum, cum in my ass,” she begged.

I felt powerful and dominant with my impressive dick stuffed up the beautiful ass of a woman who could not get enough of me. Coleen lay submissively before me on all fours as I towered above her like some untamed animal with a strong sexual hold on her. I took firm hold of her hips and slammed once more full force into Coleen’s ass. I did that three or four more times and then I let out a loud groan as I emptied my seed deep into her bowels. I couldn’t believe how much cum I produced as my dick continued to hammer into her ass.

When I was finished I pulled out of her ass as Coleen collapsed on the bed utterly spent. I slumped down next to her quivering body. I looked over at Coleen and I noticed my seed oozing from her asshole. It resembled a natural spring as the semen just seemed to bubble up as she tried to relax her anal muscles.

Coleen and I got up, showered and returned to the Jacuzzi where we soaked our aching muscles. After the Jacuzzi I offered her a massage which she gladly accepted. I had her lay face down and worked her back, legs and buttocks. Not so surprisingly I got an erection as I massaged and fingered her ass again. I came a second time that night when I fucked her ass again. After the ass fuck I rolled Coleen over on her back and continued the massage this time working her tits, abs, legs and pubes. I finished her off with another thorough pussy eating which had her screaming my name and humping my face with her volcanic orgasm. After that we were really spent and had just enough energy to shower, dress and drive home.

Marty got home for her international flight late that night and I was thankful that she was too tired for sex. In the morning I woke up with my customary piss hard-on so I fucked Marty senseless before she begged me to stop. I showered dressed and left a well fucked Marty in bed. On my way to the office I stopped and picked up a muffin and latte.


Coleen had always worn conservative long loose fitting skirts in the work place so I decided she needed to shed the panty hose and wear something more appropriate for sex in the office. I brought a Victoria’s Secret catalog into the office one day. Coleen stood by my side as we looked at the catalog on my desk. As she paged through the catalog, I stroke her legs and ass again through the pantyhose. Then I lowered her hose and panties and played with her naked ass and pussy. Coleen came on my fingers again and then she gave me one of her wonderful blow jobs.

Afterward Coleen selected a couple of items form the catalog to replace her panty hose. That day at lunch time we went over to the Victoria’s Secret store in the nearby mall and purchased nylons for her that had thigh high elastic tops. We also picked out some crotchless pantyhose that were very erotic. The panty hose had a waistband and two side panels attached to the stocking part. When Coleen wore the new pantyhose her ass and pussy were bare and her ass looked great framed in the hose. Coleen started wearing both the thigh high stockings and the crotch less pantyhose 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 and by the time I touched her pussy she was sopping wet. Coleen 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.

We continued to have sex in the office, car and the romantic interlude hotel. We played games with each other taking turns being a slave and having to do what the other person demanded. There were times after aerobics that Coleen would come into my office and I would pull her spandex down just enough to bare her ass. I would fondle her ass and finger-fuck her pussy. There was no shortage to our imagination and willingness to have sex in public as well as private places. Coleen, I was to learn, was somewhat of an exhibitionist. She loved to be totally naked in private places and was really turned on by the chances we took in public places. She loved it when I ran my hands under her skirt and inside her panties. She loved it when I pulled her spandex down to her knees and played with her buns and pubes. Coleen could never seem to get enough of my cock. She loved to fuck me, suck me and have me fuck her ass.

I was always concerned about the possibility of someone walking in on us even though the office door was locked. Staff from facilities and security had master keys and they could easily enter my office. It was one of the reasons we were never totally naked in the office. If someone did try to enter the office we could be dressed before the door opened. However, Coleen wanted to expand our office sex beyond oral sex and fingering. So I picked up a door brace at the hardware store and we used that to keep any intruders out.

Coleen would enter my office close and lock the door and then put the door brace in place. Then she would stand next to me and hold her skirt up while I pulled her panties down and off her body. She then moved to one of the chairs in my office and sat in it with her legs splayed and her pussy on display. I moved over to her, dropped my pants and undershorts and put my cock in her pussy. I fucked Coleen until she came several times. Sometimes I would cum in her pussy and other times I would fuck her ass. Coleen would kneel on the chair with her skirt thrown up over her back and her beautiful ass pointed at me. I took the lotion from my desk and lubed her asshole and my cock and then fucked her until I filled her ass with my seed. I kept paper towels in the office and we would both clean ourselves up and then get dressed.

Coleen loved our games and she loved to act as if it were the first time each time. She would stand by my desk acting innocent and awaiting my move. I slid my hand up her leg and I felt her tremble slightly as we had played this game before and she knew where it was going. I let my hand ride about and down her stocking covered leg for a few minutes. Then I let my hand wander above her knee and past the top of her elastic top hose. Coleen shivered as my hand touched the bare skin of her thigh. I caressed both of her thighs and I could tell that she was getting hot. The back of my hand brushed against her panty covered pussy and I could feel that the panties were soaked with her excitement. Coleen moved her legs wider apart causing the skirt to tighten around her shapely ass. I rubbed her inner thighs between her legs and flicked my fingers over the material covering her vulva. Coleen jumped involuntarily when she felt my hand on her pussy.

“Your panties are very wet Coleen. Would you like me to take your panties off you?” I teased her.

Coleen nodded and gasped, “Yes, please take my panties off.”

I eased her panties down over her buttocks, past her thighs and then let them slide to her ankles. Coleen stepped out of them and I put them on my desk. I returned to fondling her ass and thighs and I soon had her squirming with desire. Coleen moved her body as if she were trying to get my hand near her pussy so I slid it between her legs and stroked the outer lips of her labia. Coleen squirmed under the touch an emitted a soft groan. I started to push Coleen’s skirt up but she stopped me and then she took it off. It was a wrap around skirt and she had it off in an instant. She looked so sexy standing there leaning forward slightly on my desk. Her cute ass was framed by her thigh high hose and her short blouse ending at her waist line. She actually looked hotter by keeping the blouse on.

I ran my hands all over Coleen’s ass, thighs and pubes feeling her wet pussy. I slipped my finger into her vagina and then added a second one. I took some lotion from my desk and I pushed a finger between the cheeks of her ass and massaged into her nether hole. Then I fingered Coleen’s ass and pussy at the same time. She was going wild with the double penetration and cried out to me.

“That’s it finger me, play with me. Make me cum, please make me cum,” Coleen pleaded in a deep whisper.

I continued to work her ass and pussy and within minutes she had her first orgasm. Coleen held onto the desk with both hands as her body jerked and spasmed with her climax. I worked my fingers in and out of her holes as she clenched and relaxed her vaginal and anal muscles tightening herself on them. I pulled my fingers from her holes and I stood up behind her. I dropped my pants and boxers to my ankles and brought my rock hard cock to her buttocks. I let it rest against the hot flesh of her ass and I leaned over and whispered in her ear.

“Where do you want it first today? Do you want it in your ass or do you want me to fuck your pussy first?” I teased her and then licked her ear.

“Fuck my pussy first and then my ass. I want you to cum in my ass,” Coleen murmured.

I then eased my cock into her pussy and fucked her from behind until Coleen orgasmed once again. Then I moved my cock to her ass and fucked her for a short time before I unloaded my semen in her anal canal. Coleen looked so hot leaning over the desk with my cock sliding in and out of her asshole that I just couldn’t prolong my ejaculation any longer. I leaned over her and she milked my cock dry until it softened and popped out of her ass.

Our sexual encounters in the office usually ended up the same way, with me cumming in Coleen’s ass but only after she had cum herself two or three times. Coleen would surprise me from time to time. One day she leaned over the desk and as I ran my hands up her legs I discovered that she had already removed her panties. Another time she just walked in and immediately took off her skirt and panties. Without her skirt and panties she looked very hot in just her hose and blouse. There seemed to be no end to her creativity and willingness to try new things. However she never showed interest in adding another person to our encounters.


Marty drew the weekend international duty and she would be gone from Friday through Monday. She was home all that week so I had to cool it with Coleen in the office so that I could perform for Marty. In didn’t stop Coleen and I from having sex but I was careful not to cum. At home each evening I was ready to blow my load and Marty was happy to accommodate me. She didn’t know what got into me but Monday through Thursday evenings I fucked her brains out and came in buckets. Each morning before work I gave her a ride with my morning piss hard-on. Marty was worn out by the time she left for the airport on Friday.

I had arranged for Coleen and me to spend a weekend at a nearby resort that offered many amenities including a casino. We checked in on Friday evening and stayed three nights. We brought work clothes with us for Monday as we planned to go to work right from the resort. The resort had a huge swimming pool with a swim up bar, a spa, golf course, nightly entertainment and the casino.

We checked in and were shown to our room. We both unpacked and then I stripped down to my underwear. I assumed that we would shower and then go to dinner. Coleen smiled and grabbed my cock through my boxers, “Ready?” she teased.

“You know I am,” I replied as I grabbed her ass through her slacks.

“Let’s fuck before we go to dinner,” she said as she began to disrobe.

In a matter of minutes we were both naked in bed and I was drilling her pussy. My cock was buried in her and I made sure that in stayed in contact with her clit. Coleen orgasmed quickly but we kept right on fucking as I knew that she would cum at least once more. She wrapped her legs and arms around me and held me tight as she humped my cock. Then she exploded with another orgasm and it was intense. She cried out and bit softly into my shoulder to stifle her screams.

“God that was great! Did you cum?” she gasped.

“No, I can wait though. Let’s get some dinner and then we can play some more after we eat,” I answered.

“Let’s have room service,” she suggested.

“Fine with me,” I agreed.

We looked over the room service menu and made our selections. Coleen then got dressed in relaxing clothes while I called in our order. We sat out on the balcony overlooking the pool. Twenty minutes later the food was delivered and we dined on the balcony. I had ordered two bottles of wine as well knowing that it would be a long evening.

After we ate we relaxed on the balcony finishing the first bottle of wine. Coleen started getting frisky and she put her bare foot in my lap. Then she ran her foot over my stiffening cock as we drank our wine. I felt my cock harden under her foot but I made no moves to take the action further.

“Take your cock out,” she told me.

I fished my cock out of my shorts and it stood up in an erect position. Coleen had slipped off her other sandal and then she placed her feet around my cock. She rubbed both feet together up and down my shaft. It was a very erotic act and I decided to let her have her fun. I felt my balls tighten as they normally did right before I ejaculated. At that very moment I decided to cum on her feet.

Coleen had a very wanton look on her face as she jerked me off with her feet. She was really getting into it and I decided to surprise her with my ejaculation. Then without warning cum spurted out of my cock shot straight up and landed on her feet and shins. Coleen giggled when I came but she went right on stroking my cock with her feet. She continued to rub my shaft with her feet squeezing cum from it.

Then she spoke softly, “I douched my pussy and my ass for you when I was in the bathroom.”

I knew exactly what she wanted without her asking, “So are you telling me that your bottom is squeaky clean and that you would like my tongue in there.”

“Oh yes,” she said excitedly.

We then left the balcony and headed to the bed stripping off our clothes. Coleen never bothered to wipe the semen from her feet. She was anxious to be rimmed again and I was ready and willing. Coleen got on the bed on all fours and wiggled her ass at me in anticipation. I got behind her and ran my hands all over her lovely buttocks and then pried them apart to expose her anus. I dipped my tongue between her cheeks and tickled her pink rosebud. I pushed my tongue into her taut anus and wondered how she could take my cock in there so easily. I licked Coleen from her anus to her pussy and she went wild. I kept that up until so orgasmed and collapsed face down on the bed.

Then I began to massage her body as she recovered. I used the body lotion supplied by the hotel and covered her back and shoulders with it. Then I worked my way down to her legs and massaged her calves and the back of her thighs. Next my hands covered her curvy buttocks and I massaged those glorious globes. I lifted Coleen by her hips and she kept her head on the mattress and turned her face to the side. She had a dreamy look on her face as I fondled her buttocks and began to finger her anus.

Satisfied that she was well lubed, I eased my cock into her ass and began to fuck her slowly. I was determined to take my time and last as long as I could. I loved watching my cock slide in and out of her shapely ass and I felt as if I could last for hours. I don’t know how long I fucked her in her ass but by the time I ejaculated my thighs were burning. I fired several streams into her rectum and as she always did Coleen milked my cock with her sphincter muscle.

We were both exhausted so we moved into the spoon position and cuddled together. We fell asleep in that position and didn’t move until morning. Then the insatiable rejuvenated Catherin was ready for morning sex. Once again I fucked her with my morning piss hard-on until she begged me to stop. Then after I relieved myself we fucked in the shower and I took her ass again. After the shower we dressed and went to the coffee shop for breakfast.

After breakfast we donned our swimwear, packed a bag and headed for the swimming pool. We spent most of the day by the pool and ate lunch poolside. Later we returned to our room, showered and dressed for dinner and a show. After the show we stopped by the casino for a while and Coleen played Blackjack while I played Craps. Ironically we broke even as what she lost at the Blackjack table I won at Craps. It was near midnight when we returned to the room and we were so tired that we passed on sex until morning.

We spent most of Sunday morning in bed. The day started off with me fucking her into submission with my morning piss hard-on. Coleen had begun to love that ritual. This time I was trying to survive the morning as she rode my piss hard-on. She was determined to orgasm as many times as she could that morning until she could not cum anymore.

“Don’t pee in me,” she teased as she rode my shaft like a woman possessed.

“Don’t worry, that is not a possibility,” I answered remembering how difficult it was to pee with an erection.

I knew that my cock would stay hard as long as Coleen rode me and that I would not accidentally pee in her pussy. She rode me hard and at times I thought that my bladder would burst but it held out. Finally after a number of mild orgasms she climaxed and collapsed on top of me. I wrapped my arms around her body and held her tight as she bucked and screamed.

Coleen was always vocal when she orgasmed and often she would cum so hard that it was scary. I had gotten used to her orgasmic behavior and I loved to make her cum as much as I could. After a few minutes she rolled off of me and flopped over on her back.

“That was marvelous. We will have to figure out a way to have more morning sex from now on,” she sighed.

I rolled out of bed and made my way to the bathroom with my erect cock pointing the way. I stood over the toilet and tried to aim so that when I finally urinated that I would not miss the toilet. It took several painful minutes for my erection to soften enough so that I could pee and then finally success. It seemed like I peed for at least two minutes and the pressure was extreme. Then I washed my hands and my penis before returning to the bedroom. Coleen was waiting for me on all fours with her ass well lubed.

I got to my knees behind Coleen and kneaded her gorgeous ass cheeks. I began to kiss her cheeks and run my tongue lightly in the crack of her ass. Coleen wiggled her ass feeling very wicked as I tongued and kissed her cheeks and got close to her nether hole. I lifted Coleen by her hips so that her ass was perched in the air. Coleen’s head was still on the bed and she turned it to one side and let out a gasp as my tongue licked close to her asshole. I ran my tongue from her pussy to her ass causing Coleen to tingle in anticipation of what might be next. I spread her ass cheeks with my hands and dipped my tongue into the crack locating her nether hole. My tongue slowly circled her anus and she flinched at the contact. I pushed my tongue as far as I could into her asshole and I found myself needing to fuck her up the ass. I continued to ass fuck her with my tongue and she was at my mercy. Her desire grew as I worked her to the point that she really wanted more in her ass.

Coleen arched her back and pointed her beautiful ass back at me. I coated her asshole with a generous amount of cream and slid my thick finger into her hole. I took my time preparing her ass relishing every moment. I coated my entire cock with the cream and placed the head at the entrance to her anus. I pushed forward and the thick cock head squeezed into her tight asshole.

Coleen winched in response as her asshole was stretched wide and she gasped, “Go slow. I love it when you go slowly.”

I withdrew my cock head and pushed it back in this time causing more pleasure than pain. I pushed until a couple of inches were in Coleen’s ass. I could feel her sphincter muscle surrounding the first 2-3 inches of my cock. Coleen relaxed and felt more of my cock slide into her asshole. She grunted out loud as she felt fuller and a wave of pleasure passed through her body. I kept feeding more and more of my cock into her ass.

“Oh my God, you feel so good, I feel so full,” cried out Coleen, “Uh, uh, uh oh yes, it’s so good,” she cried out.

I reached around and played with Coleen’s clit as I pounded her ass. Her pussy and asshole were on fire as my big cock reached the sensitive areas in her passage. Coleen was on the brink of another huge orgasm as I methodically fucked her in her tight anus with my sizeable cock. I loved watching my big cock slide out of her shapely ass and plunge back in as my hips slapped against her curvy ass cheeks causing them to jiggle with each thrust. I loved watching her ass impaled on my cock. Coleen looked so submissive and vulnerable on all fours as my cock filled her asshole. Her orgasm surged within her as I fucked her ass harder and faster. I loved fucking a beautiful ass and Coleen’s was the best I ever had.

As Coleen had a string of orgasms her entire body went into spasm. Her pussy convulsed and clamped around my fingers coating them with her cunt juice. Coleen’s asshole pulsated as I drove my big cock in and out of it. Her ass involuntarily squeezed and released my huge member as I fucked it causing me to finally lose it. I slid my pecker deep into her rectum as my cock spasmed and sent a thick stream of hot cum into her channel. I kept fucking her as semen was fired into her ass and my cock kept twitching and spurting inside the impaled Coleen.

Coleen was so full of cum and there was no where for it to go as it was blocked by my swollen cock buried in her ass. I slowed my pace and eventually stopped, allowing my cock to remain buried in Coleen’s ass. I did not go soft right away and I gently moved my hips pushing cum around in her ass. Some of it trickled out and ran down over her pussy lips.

We eventually separated, showered, dressed in our swim wear and headed for the pool. At the pool we ate lunch and spent the day, sunning, reading and swimming. That evening we ate dinner and took in another show but passed on the casino. It was our last night at the resort and we wanted to have sex again before we retired. Once in bed we made slow passionate love and Coleen had multiple orgasms before we rolled to our sides and I entered her ass in the spoon position. I fucked her slowly as I was in no rush to cum.

My left arm was under her body and I fondled her breast and toyed with her nipple. My right hand stroked her clit lightly as I moved my cock steadily and slowly in her ass. We fucked in the position for at least 30 minutes and then I came in her marvelous ass once again. We stayed in the spoon position with my cock still in her ass when we fell asleep. I didn’t even remember my cock slipping from her asshole.

The next morning we were all business as we showered, dressed, packed, ate breakfast and checked out of the hotel. I drove to the office with Coleen and we left her luggage in my car. That day we passed on sex in the office but when I drove her home that evening I got one of her signature blow jobs. “That’s for a great weekend,” she said after swallowing my load. I dropped her off at her place and got her luggage out of the trunk. Then I drove back to my place knowing that Marty would be home in a few hours.


Marty continued with the weekend flights for a few months and each weekend she was gone, Coleen and I spent the weekend together. We moved around to different hotels and even spent a few weekends in the city. Coleen and I continued to have sex in the office but it was more for her than me as I had to save myself for Marty in the evenings.

Then one day I learned that I wasn’t the only one having a full weekend of sex. Marty told me one evening that she had been seeing a Frenchman in Paris and they had been having sex every weekend. She told me that she was moving to Paris for awhile. She would be living with her lover and she would she where things went. Apparently she could keep her job and be based in Paris. I wished her well and told her that she was always welcome at my place. I never told Marty about Coleen but I suspected she knew that I was getting my share of pussy when she traveled.

I told Coleen about Marty’s decision and she was thrilled as we could have weekends together. Coleen and I continued to have sex in the office and on the weekends. We had discussed her moving in with me but then we decided that it would take the excitement out of our office sex and it would be a problem if people at work learned we were living together.

We did catch a break though as Coleen’s sister took a job on the west coast and Coleen kept the apartment. I paid for her sister’s share as it was less expensive than weekend hotel stays. Instead of going away for weekends, I would spend them at Coleen’s place. We still had our office sex as we found that to be the most exciting. Maybe it was the possibility of getting caught or maybe it was just that there were hundreds of people in the building. I never tired of having her bend over and pulling her panties down to unveil her incredible ass. Of course I could never get enough of anal sex with Coleen and she loved every minute of it.

Our affair continued for four years until I was offered a big job in New York. I wanted Coleen to follow me to the city but she elected to stay in the Midwest. She did visit me a few times but then one day she told me she was getting married. I wished her well. In spite of all the great looking ladies in Manhattan, I always remembered the exciting sex with Coleen.

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