21yo Works With Older Boss - Ch. 01

The week I am going to describe here changed my life. I turned up for a weeks work as a temporary secretary to a director (Bob) of a medium sized company. The chemistry was instant. He seemed old to me at the time, but he was probably early forties. As for me I was twenty-one, in a three year relationship that was going nowhere. Why I was still with my boyfriend I have no idea. There was nothing good about the relationship and even the unimaginative sex we had had dried up. It was therefore a naïve and sexually unfulfilled woman who turned up.

The work was not demanding and I spent much of the first day working beside Bob. I could sense him appreciating my body whenever he got the chance. It might have felt uncomfortable but it felt wonderful. He had a manner that left me wanting to do anything and everything I could for him.

I was aware that when I went into his office soon after 5.30 all the staff in the area had gone. We went through the letter I had just typed and he thanked me. He then looked me in the eye and said the most unexpected thing I had and still have ever heard.

"I am going to be back here in five minutes. You can leave straight away or you can be here when I return. If you stay you will be kneeling on my desk with your head down and your beautiful bottom high in the air. You will be completely naked and will not say a word. Whether you stay or go I will see you back here at 8.45 tomorrow morning."

With this bombshell he walked through the door behind his desk without another word. It was at least 30 seconds before I had re-run what he had said and tried to make sense of it. There was no sense to make of it. I started to consider the possibility of staying but knew it was totally bonkers. When I started to consider the option of leaving my heart sunk. I felt empty and I knew I would be gutted if I didn't stay. My body was buzzing. I had never felt this alive in my life. If I stayed what would happen? What did I want to happen? The only thing I did know was I wanted to find out.

My clothes came off quickly until I had just my panties on. I then panicked. Was my bottom totally clean? There wasn't time to go and wash. I made the best use of my brief panties to ensure I was clean. I climbed onto the low desk facing away from the door he had gone through. I rested my head on my arms and pushed my bottom as high as possible into the air. My boyfriend had never been keen to take me from behind. I felt more vulnerable than I had ever felt. Vulnerable but so excited. I closed my eyes when I heard the door behind me open and close.

"Not a word. Open your legs wider."

I did without thinking about it. Much to my surprise he did not touch me but pulled his chair up behind me and I think he sat down. I wanted to ask so many questions. The most relevant of these was why was he not fucking me? Was there something wrong with me? It seemed like hours before he said one word.

"Masturbate."

It was almost a relief. I had been buzzing for minutes but I was still a little surprised just how wet I was when my fingers found my pussy. I had never masturbated in front of anyone before. Somehow it seemed to be almost natural given that I was kneeling naked on this stranger's desk while he sat watching.

I was excited in so many different ways. I was loving exhibiting myself to this gorgeous sexy man. My fingers were causing havoc between my legs particularly to my clit. Expectation was building by the second. I imagined him fingering me and then fucking my vulnerable pussy.

My fingers were soon threatening to unhinge me. I wanted to orgasm but I wanted his prick inside me before I did. I was delighted when I heard him stand up and push his chair back. I sensed rather than felt him get very close to my bottom. If I was right I heard him draw a breath in through his nose. The bastard was sniffing me without touching me. I was so close to screaming at him to fuck me but remembered his clear instruction.

He may have been smelling me but now with his lungs full he started to blow air directly onto the heart of my anus. My bum twitched and I tightened what had been my very relaxed arse. Another deep intake of breath was followed by my clit being hit by air targeted perfectly. I knew I was not far from having an orgasm and pleaded without using a single word. I was suddenly aware that he was no longer inches from my pussy.

"See you at 8.45 tomorrow morning don't be late."

The most amazing encounter of my young life came to an abrupt end in yet another amazing way. By the time I pulled myself together Bob was long gone. I spent the evening at home trying to work out what had happened. I was aroused all evening remembering the earlier events. I did not find sleep easy and had to fight myself not to end up masturbating. I knew I would be seeing Bob the next day and I had no idea what that would bring. The only certainty was that it would not be predictable.

I was there early in the morning, suffering from lack of sleep but frighteningly excited. Sexually excited. The day was unbelievably uneventful. Bob was as he had been the previous day, charming and totally gorgeous but very professional. When I entered his office with what I hoped was the last work of the day my pussy was leaking.

"Is that all for the night Sir?'

I never called him Sir but I did so in the hope to provoke a reaction. I got it.

"That is up to you my dear. I will be back in five minutes. I will either see you then or tomorrow morning at 8.45."

He opened a draw in his desk and took a box out of it before putting it on the desk. He did not look at me as he walked out of the door. I opened the box before he closed the door. Inside the box was a tube of lubricant and a smaller box labeled butt plug. Unbelievably at 21 it wasn't until I had studied the instructions that I understand its purpose. I now knew its purpose but what was Bob expecting me to do with it? As he had given me no instruction but I wanted to show him how willing I was, I took the plunge. I lubricated both the plug and my tight bottom. It was much more painful than losing my virginity but eventually, on about the sixth attempt, it slipped past the widest girth and settled deep in my bottom. He had not said anything but I knew I had to be naked on his return.

I am sure that it was more than five minutes before I was in position and he was seated behind me. The one word command was music to my ears. This time I was determined that my masturbation or better still some intervention from Bob would bring me to orgasm. My pussy felt stretched by the butt plug deep in my arse. My clit felt stretched by my fingers that were soon working hard. It was working as the excitement built until his words destroyed everything.

"It is not time. You have not earned it. I will tell you if and when it is your time. I want to see you fuck the butt plug. Push it an inch out and then suck it back in."

Inwardly, I cried with the frustration but made no noise. I reached back as I was concerned if I pushed the plug out an inch it might come right out. The idea of that happening horrified me. I pushed it out and back in quickly. It felt so dirty but so exciting. He was very close behind me seeing me doing something so intimate, embarrassing, humiliating, dirty and so fucking arousing. I repeated the action a dozen or so times. The penetration was as arousing as having a prick in my pussy. At last I heard him stand up. He removed my hand from the plug and ensured it was fully inserted. I had no idea what would happen next but held my breath in anticipation. Everything seemed to be worthwhile when my pussy was contacted by what I knew immediately was the head of his rock-hard cock. I managed to stop the urge to push back and impale him. I could not stop myself from saying, rather pleading.

"Please"

"I said not a word. One more word and I am gone."

I had no doubt that he meant it and the idea didn't bear thinking about. I needed to be fucked and I needed it now. Surely he would fuck me now. The head of his prick played around the whole of the area of my pussy. It felt very special as it circled my clit time and time again. With horror I remembered how close to orgasm I had been the day before. Would he leave me hanging again?

"If you want me to fuck you keep perfectly still and relax your pussy."

It was the strangest feeling having to keep still and relaxed just when I wanted to express myself. The feeling of total submission was overwhelming. Even then he teased me for what seemed like hours but was probably no more than 30 seconds. When he eased his cock into me it felt a little bit like losing my virginity again. No pain but I was being stretched to enable him to enter my pussy while the butt plug was already filling me. He took many gentle but firm strokes to work himself fully into me. He felt huge but I think the butt plug was partly responsible. When he was fully buried he repositioned himself so that his stomach was against the plug.

"Push the plug out as I push into you."

Right at this time I would have done almost anything he asked. He seemed to know what I wanted. It was stunning as he pushed into me and the plug tried to escape my bottom. As he pulled out his stomach pushed the butt plug deep into me. I had never felt so full in my life. I wanted this double fucking to last forever but I had been on the brink of orgasm for minutes. All I could do to delay the inevitable was to relax except when pushing out and keep as still as possible. I delayed my orgasm by all of 30 seconds before my whole body exploded. My body was no longer under my control as he increased his pace and his power. The spasms were stronger than I had ever felt. I have no idea how long they lasted but his prick was withdrawn as they ebbed away.

I thought he had finished with me as he pulled the butt plug from my bottom. In fact he did so to enable him to replace it with his still rock-hard cock. I panicked expecting pain but received only deep pleasure. When he reached round me and found my clit it responded immediately. I thought that the stunning orgasm I had experienced had left me satiated but he masturbated my clit beautifully as he gently fucked my bottom. My urgency had gone but the arousal and pleasure was perfect. I wanted to tell him but remembered his threat to be gone.

My boyfriend never lasts more than three or four minutes but this was a marathon compared. My second orgasm grew so slowly I was afraid I would never quite get there. I got there. It was different to anything before as it washed over me. It was blissful but with a gentleness I had never associated with orgasms. As it ebbed away I knew he was nearly ready to explode himself. I was disappointed that he was almost quiet as I felt him unloading deep in my bowels.

He withdrew, kissed me on the bottom and said, "8.45 don't be late." I couldn't wait to see what he had in store for me the next evening.