Routine Duties

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Jan meets Chuck in his office.
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(This is the second part of a true story that my wife, Jan, and I experienced this past summer. We apologize because it took so long to write this but we are still pretty involved with this story. We know it ends abruptly but we are already working on the next part of it. If you would like to read the first part of this story it is called "Oh No!".)

It was a typical Tuesday night for me. I got home from work at 6:45 and began making dinner. I figured that my wife, Jan, was at the aerobic exercise class that she attends every Tuesday and Thursday evening after work to maintain her shapely figure. She has worked hard on keeping herself in shape since she began working at her job with an advertising agency. Jan is 25 and has a college degree in business and marketing and was hoping to land a position in advertising once she had completed her bachelor degree. However, there was nothing available so she settled for a position as executive secretary to the vice president of a medium-sized firm. She had previous experience as a secretary and she is still hoping for a break into advertising itself.

Last weekend, Jan and I role-played a sexual fantasy of ours, where she stood on a street corner dressed as a hooker and I drove up to her as a john, and picked her up. It was extremely exciting for us but there was an unexpected twist when one of the upper management personnel at her office picked her up first. The senior manager in charge of finance and billing who was out cruising for a prostitute stopped to pick up someone and it turned out to be Jan. He recognized her before she recognized him and she was so embarrassed that she did not know how to react.

Mr. Hassek thought that Jan was a real hooker and was trying to earn additional money by walking the streets. She attempted to tell him that she and I were simply playing sex games and that she was not a real whore. He did not believe her and paid her $75 for a blowjob, while parked in his Cadillac, in the darkened parking lot of a bar. Jan gave him the blowjob and even swallowed his cum. He then told Jan that he was interested in trying out her pussy, which he had been fantasizing about ever since he had first seen her at work. He had told her that he wanted to have a "date" with her on Wednesday night after work.

Jan and I had been having hot and nasty sex for the entire weekend after her debut as a street whore, while reliving the situation where she got picked up by Mr. Hassek. She would tell me in detail how the conversation went with her john. She would then tell me how it felt to be a whore with a strange man's cock in her hand and then in her mouth. Jan had sucked his cock until he had shot his load into her mouth, and then he had made her swallow all of it. She would lie on her back, with me on top of her fucking her, while she replayed the entire scene. It never failed to arouse her greatly leading to several orgasms for her. She liked calling herself a street whore as I made love to her.

The nights following the tryst were filled with our describing to one another her future "date" with Mr. Hassek and how he would use her as his whore and pay her $200 for the privilege of using her for his carnal pleasure. We would discuss this while laying in bed and this also led to passionate nights and days of marathon sex sessions.

I was hoping that on this Tuesday night we would have another night of fantasy discussion and the subsequent sexual release that would result. Jan had been a horny babe ever since that evening on the street and I found her to not just be receptive but aggressive in her sexual behavior. I think we were both secretly hoping that he would hire Jan again as his prostitute.

Jan had gone to work on Monday dressed in her usual work attire of a business length skirt and a silk blouse. She had worked with Mr. Hassek but neither of them had revealed a hint of having seen each other at any time outside of work. It was business as usual filled with Jan's routine duties. She was the executive secretary to the Vice president of the advertising agency but she also prepared documents and reports for and with Mr. Hassek. Jan was starting to believe that her secret sex life was safe and that Hassek's words to her about a Wednesday "date" were simply a threat to intimidate her. I was quite surprised by Jan's appearance and what she revealed to me upon returning home from work on Tuesday.

"Hi honey, your hooker wife is home." Jan called as she walked into the kitchen where I was in the final stages of dinner preparation. I turned to look at her and her face was flushed and her make-up appeared freshly applied.

"Hooker wife? What do you mean? I asked in a sort of mock surprise but thinking that she was referring once again to our previous weekend's activities. Jan walked over to me and gave me a lingering hug. I hugged her back and moved my hands down to gently rub her lower back.

"Yes, hooker-wife, whore-wife, whatever you wish to call me." She replied with kind of a sly half-smile. I noticed kind of a glint in her eyes so I tried to kiss her. She avoided my mouth with her mouth. This puzzled me so I pursued a kiss even further. She finally allowed me to kiss her but would not allow me to put my tongue into her mouth. She broke the kiss and looked me in the eyes. Her pretty blue eyes never fail to melt my heart and they didn't this time either.

"Jan, what's the deal?" I asked.

"You can probably smell him on me." She replied cryptically.

"Smell who? What are you talking about?" I asked a little more forcefully than before.

Jan didn't reply right away but instead took me by the hand and lead me to our bedroom. She pushed me down onto the bed and climbed on top of me. I reached for her warm body and she allowed me to pull her close. I held her and snuggled with her for a few minutes and then my hands slowly began to caress her soft but firm little bottom. She appeared to enjoy that so I continued to squeeze and rub her. I started to feel my cock becoming erect so I inched my hand slowly under her skirt between her legs. My fingers were greeted by a warm and damp feeling as I inched higher. As I touched the crotch of Jan's pantyhose I knew that she had been up to something as she was very warm and very wet in that special place. Jan began to make soft growling sounds so I knew she was enjoying my touches.

"Do you want to tell me what happened today?" I asked as I began to tug Jan's pantyhose down off her legs.

"Are you sure you want to hear about what kind of slut you are married to?" She asked as she helped me by pulling her pantyhose and panties down over her butt and down her thighs.

"Baby, I want to hear every detail about what a naughty little slut you are." I answered as I pulled her hose and panties off from her legs and on to the bed. My hand slid up her soft warm thighs and onto her very soft and wet pussy. Jan felt like she had just been playing with her pussy or had let someone else play with her pussy.

"I was at work and it was around 4:30 when I received a phone call from Mr. Hassek. I was at my desk doing some letters for John, who was in Chicago. I picked up the phone and this voice said to me.

"Hello Jan, how about a nice blowjob for $75?" I immediately recognized the voice as Chuck's voice and I felt a shiver run up my spine.

"I am not sure what you mean." I answered in my best professional secretary tone. I looked around and no one was anywhere around as John's office is isolated from the other employee's offices.

"Jan this is Chuck, is anyone around right now? Is John there?"

"Hi Chuck, no, no one else is around. John is in Chicago all week. What can I do for you? I replied in a somewhat standoffish manner. I could feel a kind of nervous excitement creep along my skin.

"What you can do for me is come to my office at 5:30 and give me one of your special blowjobs and we can discuss my getting into your pussy." He replied.

"Yes sir, I'll be there at 5:30." I replied and he hung up the phone. What the hell was I suppose to do now? I am not a whore, it was a one-night sex role-play and I did not want Chuck Hassek to think I was available as his private prostitute. On the other hand, he could really screw up my job here at the agency if I didn't come see him. Then something else occurred to me, I liked the thrill of being a paid prostitute. I was excited about the idea of a man paying me for sucking his cock into my mouth and letting him feel my body. I then thought of how much of a turn-on it would be for you if I did this also.

I finished my work as best as I could with the randy thoughts that were surging through my head. I felt my nipples begin to tingle and my clit started to stir as well. I went into the lady's room on the floor I worked on to freshen up. I washed my face and hands and wet a hand towel to take with me into the stall. I pulled down my pantyhose and panties to give me access to my pussy. I noticed my feminine odor as soon as my legs opened. I took the hand towel and washed my pussy lips and my entire crotch areas with it. The warm wetness of the towel seemed to stimulate me more as I ran it over my neatly trimmed pussy. I pulled the cloth up and examined it. My shiny secretions were apparent on the material. God I was feeling very, very nasty.

I pulled my clothes back up and exited the stall. I looked at my face in the mirror and noticed the pink flush of excitement in the skin of my neck and cheeks. My blue eyes examined the face of the woman in the mirror. "Jan you are such a slut." I thought to myself as I began applying my makeup. I put on my makeup on a little heavier than usual especially around my eyes. I then dabbed Liz on my neck, wrists and between my breasts. A quick brush and a spray of my hair and I was looking hot!

I walked out of the ladies room, put my things away in my desk, grabbed my purse, locked my desk and my office, and headed toward the elevator. I worked on the fifth floor and Chuck's office was on the third. I got in the elevator with a few other women and chit-chatted with them on the way to the third floor. We said "goodnight" as the elevator closed. I walked down the hall toward Chuck's office. My legs were kind of shaking but I didn't know if it was fear or lust. I finally made it to Chuck's closed door and knocked on it. He opened the door and usher me inside.

"Well, my little whore, right on time." He smiled as his wandering eyes looked me up and down. His eyes lingered on my breasts and I felt my nipples begin to tingle again as I looked into his eyes. He locked the door and guided me into a conference room through another door in his office. He locked that door too. His hands began rubbing my butt and I felt embarrassed.

"Chuck, I don't think…" I began but he cut me right off. He reached into his pocket and pulled some money from it and handed to me.

"Right, right. Here is the $75 dollars for the blowjob. You know you are really a very sexy woman. I am still surprised that you are a whore but I am glad!" He smiled at me as if he was giving me a complement. I took the $75 and counted it. I then opened my purse and stuffed it inside wanting to get it out of sight as soon as possible perhaps thinking that it would make it seem better when the money was hidden.

Chuck sat down on a small leather couch that was against the wall and patted the spot next to him so I would sit down next to him. I looked at him as I walked over and sat beside him. He was really not a bad looking man for being in his late 50's. He had almost a full head of hair which was dark brown but graying at the temples. I sat down beside him and he smiled and put his arm around me.

"So, Jan, did you tell your husband Jesse that I was one of your customers." He said in a pleasant but condescending tone. I was taken-aback by his question and hesitated a few heart beats before I answered.

"Justin, and yes I told him that you were my only customer. You were my one and only john." I replied. He kind of pulled me to him with his one arm and started to feel my breasts with his other hand.

"I almost believe that but you are just too good to not be a professional. Besides it doesn't matter, we both know you are a hooker now, don't we?" He said as his fingers found the buttons on the front of my blouse and began to unbutton them. I was starting to feel quite strange by now, kind of horny but kind of embarrassed and kind of ashamed. He finished unbuttoning the buttons and his hand reached in to feel my boob through my bra. I made a small sound as his fingers touched my bare skin above my bra.

"Chuck, it may not seem important to you but it is to me. I had never had sex with anyone for money until you picked me up on the street, honest. Do you believe me?" I asked as his fingers slipped over the bra and reached in to cup my naked breast. His other hand caressed and stroked my hair and he ran his fingers through it like a lover would.

"Jan, I believe you I guess, but what did your husband say?" He asked as he reached over and played with my other breast. I was starting to get excited by his touches and my nipples began to reveal my excitement to Chuck. I was beginning to feel quite aroused and wanted to tell him about our fantasy game and the results of it.

"That feels very nice when you touch me like that." I whispered and then I said. "Justin was very turned on by my story of you picking me up and paying me for blowing you." Chuck then began to pull my shirt over my shoulders and kissed me neck. He then took my hand and put in on the bulge that had appeared in his lap. I could feel his cock through the material of his suit pants. I gently squeezed and stroked him.

"He likes it, eh? Well, he will love it then when I fuck that pussy of yours. I was thinking tomorrow night after work." Chuck said with a grin as he removed my blouse from my shoulders and pulled the remaining material from the waist band of my skirt. I helped him remove it and then I reached around and unhooked the clasp on my bra. It hung from my shoulders and slightly covered my breasts.

Chuck gently plucked my bra from boobs and teased my nipples with his fingers. I began the process of unbuttoning and unzipping his trousers. He shifted his weight and allowed me to pull them down until they and his boxer shorts were at his ankles. His cock sprung up and did not appear to be the cock of an older man. His cock was a very light in color, almost white. It had a nice, round, and well defined reddish-brown head on it. A drop of clear pre-cum was emerging from the slit and I leaned down into his lap to lick it with my tongue. I smelled Chuck's manly scent as my head approached his crotch. He smelled like urine, sex and sweat. I could feel my nostrils flare as I descended to his lap. I was feeling so intoxicated by the act of smelling Chuck's arousal as I began to lick up the glistening drop from his cock.

"God, Jan, you are so beautiful, this is like a dream come true." Chuck exclaimed as I began my oral pleasures.

"I am his whore.' I thought to myself as I planted kisses with my lips and licks with my tongue to his cock. Chuck's hands were busy caressing my breasts and pulling and rubbing my nipples while I began working to give him his money's worth. He slowly worked one of his hands between my thighs and was beginning to play with my pussy through my pantyhose and panties. I spread my legs further apart to give him better access to my very horny pussy. I was hoping he would touch my clit with his fingers as I needed to feel his touch on my very erect clit.

He disappointed me and instead reached around to pull down my pantyhose and panties.

"Lift up." He ordered me so he could get to the waist band of my panties and pantyhose. I complied and he tugged them both off from my waist and down to my ankles. His hands began rubbing and stroking my buns. His hands were very warm and I enjoyed his touch. I made a sighing sound as his hand returned to my crotch, to my very warm and wet pussy.

"Jan you are such a sexy lady I can't wait to get you into bed and to fuck your sexy ass." Chuck told me as his fingers found the wet opening to my body and he began to run his finger over my pussy lips. His finger felt slippery but wonderful as he rubbed it over my clit. I was having a problem concentrating on the task in my mouth as he was making me feel so good. I started to make little moans as he slowly made circles with his finger on my clit. Chuck knew what he was doing and stopped masturbating my clit and instead slipped his finger into my horny pussy. His fat finger felt like a cock entering me and I opened up my legs further to give him complete access to my pussy. At this time I had a majority of his cock in my mouth and I was sucking it and moving my mouth up and down on his erection.

"Jan I want you to cum for me, cum like the little whore you are." Chuck ordered as he slipped another finger into my pussy and fucked me hard with the two of them. His other hand was squeezing and pinching my nipple and this drove me closer and closer to my impending orgasm. I hunched myself on his fingers as I took his entire cock into my mouth and throat. I moaned loudly onto his cock as he continued to fuck my pussy with his fingers. I felt his cock begin to pulse and the head swelled larger in my throat. I knew he soon would be cumming and this drove me over the edge. I came on his hand and this triggered Chuck's orgasm too. He shot two squirts into my mouth and throat and I swallowed them. He stopped fingering me and his fingers slipped from my pussy and breast. He kind of convulsed as he continued his orgasm with one final jerk into my mouth.

"Jan, you are so hot! You make me feel so great!" Chuck whispered to me as I let his cock slip from my mouth and I watched it bounce against his belly. A string of saliva and sperm connected my mouth to his cock.

I smiled and caressed his balls. I looked him in the eyes and said.

"You are no slouch yourself, you are really quite a sexy man. You sure cum a lot, it almost choked me." I said as I laid my head on his belly and licked the ooze from the slit on the top of his cockhead. I found myself watching his cock slowly become softer and softer. He was patting my head and caressing my hair. He then spoke to me.

"That was a wonderful blowjob Jan, you are the best whore I have ever had suck my cock. You are well worth the money. Now about tomorrow." I shifted around and looked up into his face as he spoke to me.

"Chuck, please…I am not a whore." I pleaded with him. He smiled at me and then said.

"Maybe you weren't a whore when I first picked you up but I have paid you twice now for a world-class blowjob so I would say that you are definitely a professional now. Tomorrow night when I have had you in my bed then you will definitely be a whore, my whore." He replied.

"Now tomorrow night, I want you to meet me at the Black Swan Restaurant at 7:00, the reservation will be in my name." He informed me. The Black Swan is the most exclusive restaurant in town located at the top of the best world-class Hotel in town and I was impressed by this.

"I want you to be dressed, not as a hooker, but as my date for an evening of dining and drinking at the classiest place in town. You are a classy woman and I want you to look the part. Dress to impress and we will have a great time. I will be there waiting for you." He finished his directions and began to pull his pants back up. I felt like I had been dismissed and began pulling my panties and pantyhose back on to preserve the sloppy mess between my legs. Chuck watched me dress and when I was finished he pulled me close and hugged me. It was a tight warm hug and it felt reassuring to me. I hugged him back and he rubbed my lower back. I felt the need to kiss him but he only allowed a kiss on the cheek.

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