The JOY of Anal Sex - Cover

The JOY of Anal Sex

by Master Jonathan

Copyright© 2022 by Master Jonathan

Erotica Sex Story: Michael was sent from Corporate Office to get a satellite office back in order and earning money again. When he arrived he found his secretary was more than helpful in making him feel at home!

Caution: This Erotica Sex Story contains strong sexual content, including Consensual   Heterosexual   Fiction   Workplace   Anal Sex   Analingus   Oral Sex   .

From the first day I laid my eyes on her, I wanted her. I had recently been transferred from the corporate headquarters in New York to head up the San Francisco office. I arrived on a gloomy, foggy Monday morning in July.

Traffic was creeping along because of the fog, and I was certain to be late. Not a good first impression for the new boss man to make on his employees. Especially when I was sent there primarily to get the place back in order after the previous manager had let the place fall apart!

Despite ‘Frisco’s best efforts though, I made it to work just in time and after taking the elevator to the 5th floor, the door opened to a large open floor with rows of small office cubicles.

“Hello, can you show me where the manager’s office is?” I asked the first person I came to once the elevator door opened. The guy grumbled as he pointed to a formidable wood door at the end of a row of cubicles. I went down the row and entered the office. Putting my briefcase down on the desk, I began unpacking the things I needed and setting up my new office.

“Can I help you sir?” a female voice behind me said. I turned around to see the most incredible specimen of womanhood I had ever seen.

Joy was 24 years old, about five foot six inches tall, with chestnut brown hair and an amazing 36-24-38 body with fake (but very nicely done) tits. She had a face like a fucking doll – hell, she looked as if she’d stepped out of a porn movie.

“Yes, I’m sorry, you caught me off-guard. My name is Michael Reynolds and I am from the corporate office in New York,” I said.

“Oh yes, Mr. Reynolds ... corporate said they were sending someone. We have been expecting you,” she said. “My name is Joy Andrews and I will be your secretary. I hope that you will be happy with the office here in San Francisco ... and with my work.”

“Well to be honest, Ms. Andrews, one of the reasons I was sent here is because the previous manager let this place go too much for corporate’s liking, and they sent me out here to put the house back in order,” I told her.

“Oh my, that doesn’t sound too good. I hope you don’t have to do anything too harsh,” she said, looking concerned.

“Well, first I’ll have to see where we are before I know what needs to be done to get us back on track,” I told her. “It will take me a couple days to determine that. Then I will start making whatever adjustments I think are necessary.”

“Yes, Sir. Well, welcome to San Francisco and I hope you will like it here on the ‘best coast’” she said, smiling at the joke, “Please feel free to call on me for whatever you need, Sir ... I am at your disposal.” She turned to leave the office.

As she got to the doorway she turned back and smiled. “And by the way, it’s Miss Andrews, Sir ... or Joy.” She held up her left hand and showed me there was no ring on her finger. Joy shut my office door as she left and I sat down in my chair for a couple moments composing myself!

I began going through some of the office’s past reports trying to figure out where to start putting this office back on track. I knew that every person in that office was worried about their job since I showed up, and I didn’t relish the idea of being the company axe-man.

So I was trying to figure a way we could all work together to get back in the black again. There was a knock, and I absent-mindedly yelled out a yes, not looking up. The door opened, and I heard feet shuffling inside. When I looked up, I was pleasantly surprised to see Joy again.

“Sir, can I get you a cup of coffee or anything?” she asked.

“Yes, I would like some coffee, actually. Black with one sugar if you don’t mind,” I said.

“Of course, Sir. I’ll be right back.” She left and returned a couple moments later. She walked up to the desk and bent over, setting the coffee down in front of me. She purposely took her time fixing my coffee as she allowed me a very good view down the front of her dress. Joy knew I was looking at her too, I saw the kittenish little smirk she had on her face as she fixed my coffee. She was giving me a show and she knew she had my full attention!

“There you go. I hope that everything is to your liking,” she said when she had finished making my coffee. She winked at me, letting me know she wasn’t talking about just the coffee! “Will there be anything else, Sir?” she asked sweetly. I could only shake my head at this point, afraid if I tried to speak, I would make a complete fool out of myself. “Well, I will be out my desk then. Please call me if you need anything ... anything at all, Sir, she said, biting her bottom lip a bit.

Oh God, those red lips. They were sparkling like diamonds. I so wanted to taste their sweetness...

The rest of that first morning, I was unable to concentrate much. While I had given Joy some work to do, I was quickly trying to think of a thousand excuses to call her in. Whenever she came in, I almost instantly had a hard-on. Her perfectly shaped legs, those tits almost coming out and her beautiful, beautiful smile were having their effect on me.

During the next few days, I managed to get myself under control again. Soon I was able to work with Joy without always thinking about sinking my perpetually hard cock deep inside her wet pussy. She was one hell of a secretary. It was as if I was only working half-time, now that she was doing all the little stuff.

Of course, people from other departments were always smiling slyly at me, and I heard a few people whispering about how I seemed to spend an unusual amount of time with my secretary. But I was careful to not give credence to any kind of rumor at work.

Joy seemed to notice this too, and she was the consummate professional whenever we were around others. If my office door was open, she made sure she didn’t get too near to me and always spoke in the most respectful manner. When I had the door closed and we were alone however, she felt comfortable enough that we could flirt a bit and tease a bit, still remembering we were supervisor and employee, but also a man and a woman.

After a couple weeks of sorting, arranging, researching, and planning, I was ready to make the announcement everyone in the office had been worrying over. “Joy can you tell everyone in the office to come into the conference room – I want to talk to all of you at once,” I said one morning as I came into work.

“Yes, Sir,” she said, looking a bit concerned. She brought everyone in and closed the door once all the employees were inside.

“Thank you all for coming. I am sure you all have been wondering about what is going to happen and what I am going to do with this office. As you all know, I was sent here from New York to fix this office and get it back to the way it should have been all along. And I am sure each of you have been worried about if you would be kept on or let go. Well I have looked everything over and I am pleased to say that everyone here will be kept on board – no one will lose their job,” I said.

A collective sigh of relief swept through the room.

“That being said however,” I continued, “we are going to have to make some significant changes if we are to make this office over.” I began outlining my plans for the office and staff and with the threat of being let go not hanging over their heads, everyone was more than happy to do what they could to get the house back in order. After the meeting, I dismissed everyone to go back to work except Joy.

“Joy, hang on a minute. I wanted to thank you for all your help these past few days. I know you have been worried about your job as well, and I wanted to thank for being such a help to me. You are a wonderful secretary and I appreciate your work. How about dinner Friday night at Jardiniére?” Jardiniére was by far the most expensive and exclusive restaurant in town.

“Oh my God, Sir, that would be wonderful! Oh thank you!” Joy beamed at me. Fuck, she was so damn pretty.

“Alright then, I’ll make the reservation then. How does 8:00pm sound?” I asked.

“8:00 will be fine! Thank you again Sir,” she said.

That Friday, Joy was bustling and cheerful at work. She kept smiling at me, and I knew she was really looking forward to our dinner date that night.

After work that day, I went home and got ready to take Joy out. I knew this was a special night for her so I wanted to do it up right. When the time came to pick her up, I drove up to her apartment building according to the directions she had given me. I was still pretty new to the area, so she had written down directions to her place and I looked them up on the map program on my computer so I wouldn’t get lost.

As I pulled up to the front of her apartment building, I saw her already standing at the entrance, waiting for me. I was speechless. Her hair was pulled back into a ponytail held in place with a rhinestone-jeweled clamp, with a couple wisps framing her perfect face. She had dark smoky-eye makeup with a touch of blush on her cheeks and luscious red lipstick.

Joy was wearing a red microfiber dress that was cut just above mid-thigh, with a plunging neckline that offered me a peek at her ample breasts and a scoop back that reached almost to the swell of her tight ass. The dress fit her like a glove and she looked incredible in it. She looked fucking sexy but not slutty. I loved it.

I got out of the car and after we had said hello, I opened the car door for her.

“Oh, what a gentleman you are!” Joy said, smiling at me. I offered her hand to help her get seated and as she sat down in the passenger seat, I couldn’t help but notice her cleavage. Fuck, her tits were perfect, and there was a lot of perfection there!

The table at Jardiniére was perfect too. A bit secluded, with a nice white lace-edged tablecloth, tall white candles on the table and a smooth sophisticated atmosphere. Joy and I had plenty of things to talk about. I wanted to get to know this woman not only as my secretary, but also as a person.

During the meal, Joy kept smiling at me, and I knew she was having a nice time. I ordered us a nice Merlot to go with our dinner. After the meal, we started to talk again, and after our first bottle of wine, things went even smoother. We were already down to some rather intimate topics, and sooner or later, we began talking about sex.

“Can I confess something? When I was in college three or four years ago, I was kind of wild and now I like things a little extreme when it comes to sex,” she said, blushing a little.

I didn’t know exactly what she meant by ‘extreme’, but I knew anything she’d do sexually would be heaven. “So, what exactly do you mean by extreme?” I asked innocently.

“Well, that’s nothing to discuss in a place like this. I think we should move on!” Joy said. So she wanted to move on. Okay, I was fine with that. After I had paid the check, we went to the car.

As we pulled out of the restaurant parking lot, I asked “So, where do you wanna go?” She thought for a while.

“Well, I hope this doesn’t sound too forward, but would you like to go to my place? I’ve got a few bottles of wine, and we could talk better there,” she said, looking at me and waiting for a decision.

I agreed, and we drove back to her place. As we drove, I began tentatively “testing the waters” and seeing just how receptive my date was to the idea of something more sensual and intimate. I let my hand casually wander over and “accidently” brush her thigh. When I didn’t get any resistance, I tried again, a bit more confidently. This time as she felt my fingers trailing up her leg, she parted her legs as much as she could given the tightness of her dress.

“Mmm ... I can’t wait to get out of this dress!” she said softly. I was all in favor of that, myself! With her parted thighs as license to explore her more, I let my fingers trace the length of her stocking-clad leg, inching slowly higher until I reached the hem of her dress. I paused there, still uncertain just how much liberty I had been given.

Joy must have sensed my hesitation because she raised up a bit in her seat and pulled her dress up, freeing her legs to spread wider and giving me more territory to explore! My hands went right to work too, roaming higher until I felt the tops of her stockings and the naked warm flesh above.

Joy sucked in a bit as she felt my hands on her bare skin, then reclined the seat back a little and closed her eyes, giving herself over to my touch. My hand continued upwards until I reached her panties, and holding my own breath, I brushed my hand lightly across the front of her panties, feeling her pussy lips through the thin fabric as I did.

“Mmmmm...” Joy mewled as she felt my fingers across her pussy and she wriggled in her seat slightly. I smiled and then began softly rubbing her panty-covered pussy. Joy spread her legs even further apart and pulled her right leg up so I had more room. She reached into the neck of her dress and slid her hand under to start toying with her nipple as she began to get more turned on.

“Please hurry...” she whimpered as her passion fire began to burn brightly. I continued playing with her and stoking her fire as we drove on. I began to notice a growing dampness as we neared her apartment building...

We arrived at her apartment just as she was getting perilously close to cumming – the timing couldn’t have been more right! As we pulled into the parking lot and to the assigned Visitor Parking area, I pulled my hand away from her crotch. Joy whimpered her dismay but I smiled, letting her know it was only a temporary reprieve.

We went into the building and began climbing the stairs. Her apartment was on the third floor so I let her take the lead – besides, it gave me a great view of her tight firm ass as we climbed the stairs!

I took full advantage of the opportunity in front of me and as we climbed so did my hands ... up the backs of her legs and under her tight dress so I could feel those two luscious globes as they danced in front of me. I felt between her legs a couple times, pleased that she was soaking through her thin panties and she had to stop twice because her knees got too weak to continue.

We made it to her floor and she unlocked her apartment door. Her apartment was small, but tastefully decorated. I sat down on her sofa while Joy went to get some wine and put on some music. She handed me a glass of wine and put the bottle and her glass of wine on the coffee table in front of the sofa.

“Excuse me for a moment ... I want to slip out of this dress and into something more comfortable. I’ll be right back,” she said. I waited for her for a couple minutes and she returned, dressed now in a comfy oversized sleep-shirt. “There, much better. That dress may look good, but it’s so tight I am always afraid I will bust a seam if I move wrong!”

“Well, you would make anything look good,” I said.

“Aww, thank you,” Joy said, blushing and giggling like a little girl. She sat down next to me on the sofa, with her feet on the sofa, and her practically sitting on them.

“Well, where were we?” Joy asked. I was just about to ask her about her confession for having a taste for extreme things, when she cried out. “Oh, yeah, the extreme stuff. Well, actually Michael, I think it would be better if I showed you rather than told you. See, I know you are attracted me, and I am certainly attracted to you.

“All night long you have been teasing and toying with me and you’ve got me all hot and wet. So I think you should take me in the bedroom and fuck me now!” she said. I was stunned by her bluntness, and wasn’t sure how to respond. But a response wasn’t necessary, because Joy was already pulling me up off the sofa. She took my hand and practically dragged me into her bedroom. The girl was assertive and hot to trot!

Once we got to her bedroom, she pushed me down on the bed and crawled up my length until she was face to face and hovering over me. She leaned down to kiss me and with her full, pouty lips pressed on mine, her tongue found its way inside my mouth. I didn’t know what to do, but my cock did.

It was rock-hard, and started to take over the control of my body. Without thinking, I grabbed Joy and pulled her down on top of me. My hard bulge pressed up against her as our tongues played with each other. She ground her hips over my stiffness and let out a muffled moan, and my hands began to explore her perfect body.

When my hands reached underneath that shirt I was delighted to find out that she had no panties on! I had already noticed by the way her hard stiff nipples poked at the shirt, she was not wearing a bra and this new discovery only fueled my desire for her more. As my hands found her perfectly shaped ass, Joy started working to undress me. My tie and shirt were the first to go.

“Oh Michael, lose your pants, please! I want to see your cock!” Joy moaned into my ear. She sprang up and I took off my pants and my boxers. Joy practically jumped at my hard cock, pushing it deep inside her mouth. Fuck, that girl was wild!

For the next few minutes, Joy sucked my cock like it had never been sucked before. Seeing those perfect red lips wrapped around my hard cock was almost too much. Just before I was about to come, I grabbed the ponytail and dragged her head upwards, pulling her up to kiss me.

While she kissed me again, she pulled off the sleep-shirt and, completely naked now, she quickly straddled my raging cock. Her pussy was hot, tight and dripping wet, and as she inserted the head, I was in heaven. As Joy bounced up and down on my pole, a perfect pair of 36DD tits was swinging, while her ravenous pussy was greedily swallowing my cock.

“Oh God Michael! Oh your cock feels so good!” Joy moaned as she rode me. She wasn’t the only one enjoying herself though, Her pussy hugged my cock and feeling her warmth surrounding my aching cock was incredible.

Then she leaned forward, pressing her tits against me and her hips began gyrating wildly, moving in ways I didn’t even know a woman could move! She began rolling her hips backward as she pulled them up and then forward as she shoved them down onto me again. The feeling was exquisite and I knew I wasn’t going to last long.

“Oh fuck, you are unbelievable!” I screamed, and pushed harder into her. Joy moaned in response and guided one of my hands between her ass cheeks. She rubbed her asshole with my hand, the wetness of her pussy had already made it wet. Joy wanted me to push a finger into her tight asshole, which I did. When I was in up to the second knuckle, Joy’s movements grew even wilder.

“God, yeah, push it in deeper, take another one, make me feel your fingers inside my dirty slut ass!” she whimpered, and I didn’t hesitate to follow her orders. The woman was crazy about having her asshole fingered! So I pushed a second finger in, relishing the tightness of Joy’s ass, feeling its contractions whenever she pushed down onto my cock.

 
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