21yo Works With Older Boss Ch. 04

Friday

Friday evening started the same way as the other evenings. When I walked into Bob's office I was so excited my heart was pounding my mouth was dry but my panties were not. The anticipation was unbearable even though I had no idea what was going to happen. I was aware that things were slightly different but could not work out what had changed.

Bob invited me to stand in front of him as he sat on an armless chair. It looked very suitable for putting someone over his lap to spank them. He opened his legs and invited me to stand between them. He looked into my eyes as he started to unbutton my blouse very slowly. He pulled it out from my short skirt before undoing the last two buttons. Still with a slowness that I found very erotic he eased the blouse off my shoulders and it fell behind me. I had been very tempted to dispense with my bra that day and again before I had entered his office but was pleased I hadn't as its presence added to the eroticism.

My boobs are not as big as I would like them to be. They are very firm and conical in shape with no cleavage to mention. Even now that I am 40 they have no droop and point skywards. The only reason I ever wear a bra is that my nipples are very prominent. The bra I was wearing was opaque and seamless with the catch at the front. My dark nipples were clearly on show and had without being touched had become erect. Bob traced around both, through my bra, in circles. When the circles were small enough and the erect buttons were contacted it felt wonderful. When Bob had removed the bra his mouth found each nipple in turn and my knees threatened to buckle. I could have stood there for hours and received this pleasuring but Bob stood and eased me back on my back onto the desk.

Unusually his removal of my skirt and panties seemed almost functional but I was very happy to be naked in front of him yet again. He had put a cushion on the table for my head which allowed me to watch him undress without straining my neck. His body was fit and full without any suggestion that he spent much time in the gym. His prick was and still is the only circumcised I have ever seen. It was a good size but not the biggest I have encountered. There was something, possibly the circumcision, that made it very pleasing to the eye. Now naked he pulled his chair up and lifted my legs so that they were hooked over his shoulder. He drew a long deep breath before he ran his tongue along my pussy until he found my clit. I love receiving oral sex and this man was the best I had received it from. I relaxed back still able to watch as he pleasured me.

One of my female friends had said to me that no oral sex was as good as that received from another woman. This was so wonderful I could not imagine anybody so skilled let alone more skilled. He did stop long enough to tell me that I could speak as much as I liked and have an orgasm whenever I wanted to. This was because on previous evenings both were strictly forbidden. I enjoyed giving him a commentary of how fantastically he was doing and how great it felt. I loved the pace of things. He was not teasing me as he had done so much doing the week and I was just loving the progress to the inevitable conclusion. Given his track record I did wonder whether he would suddenly surprise me. I had started to play with my nipples that added to my feeling of surrender to total pleasure. Unlike the previous evenings with Bob this felt like lovemaking at its most enjoyable. I didn't know what Bob had planned but unnecessarily when I was very close i asked for permission. He didn't react but kept doing exactly as he had been.

I felt the orgasm building from miles away and welcomed it as it got closer and closer. I closed my eyes and a warmth engulfed me and all my closed eyes could see was orange exploding in front of me. The waves while strong did not have high highs and low lows but rolled strongly through my body. He held my hips down and his mouth managed to carry on doing what had given me so much pleasure. It was not the strongest orgasm I had ever had but it had been as intimate as any I had enjoyed. My orgasm had fully run its course before he removed his mouth just as my clit became too sensitive. I thought this might be the end of our last evening together but I had never been so wrong.

He pushed the chair back and offered his erection up to my pussy. I had just cum but I realized he had not. I settled back as he penetrated me with ease and started to gently fuck me. It felt pleasant and I was delighted to see that he was clearly enjoying the contact. He fucked me gently with long deep strokes. When he changed the angle by lifting my hips the whole thing changed for me as his fingers found my sensitive clit. His timing was perfect as my clit was sensitive but not too sensitive. Now he fucked me with great vigor and I knew he would not take long to cum. It was now a race that I just won. This orgasm was very different. The highs were high and almost sharp. The spasms were very distinct but only lasted for a few seconds. He was still thrusting into me as my orgasm ended and I was able to see the last of his.

What had happened could easily be described as he had gone down on me and then fucked me. It felt so much more than that. Had this brought the amazing week to a surprisingly conventional end? He looked down at me and asked me if I would give him one last treat. I knew I would have to make a decision without knowing what he had in mind. I had not refused this charismatic man anything all week and I didn't want to start now. I nodded my agreement but did wonder what I could offer given that I was exhausted and sexually satiated.

He walked across the room and pulled a cover of what looked like a saddle with one big difference. I did not know what a Sybian was but I did know what the dildo sticking up from the saddle was. When he led me across to it I thought it was the first time all week that I was being asked to do something that I did not want. I was able to straddle the saddle and hold the dildo just touching my lips before he started it vibrating. My clit was super-sensitive and the vibrations were positively painful. He looked me in the eyes as he gently pushed my shoulders down. My pussy did not mind the penetration but my clit screamed to be spared. Bob did not spare my clit as he eased me down until all my weight seemed to be on my pussy and particularly on my painful clit. The vibrations deep inside my pussy were pleasant but my clit was complaining. When he turned the vibration level up I asked him to stop. He said that he would stop if I sat still for 60 seconds and then asked him again to stop. The pain got worse for a few more seconds. I accepted that there would be no relief quite yet and relaxed as much as possible. Very quickly the pain morphed into uncomfortable sexual stimulation and from there into extreme sexual arousal. At this time the extreme sexual arousal was such that it was not pleasant as pain was still the strongest feeling.

I loved it and hated it at the same time. I had no idea how things would progress. When he informed me that the minute was up my mind was as confused as my body. Before this week I would have jumped of the vibrating cock. Instead I leant forward thereby putting all my weight on my screaming clit. It hurt more but it also stimulated more. I looked up at him asking him a question that I wasn't sure what it was. His smile was encouraging but gave me no more guidance. I now went for broke sliding along the saddle an inch or so in each direction. The pain and pleasure both grew. The pleasure was like an orgasm without a start or an end. No spasms just an ever increasing state of euphoria, that I sensed would only end in one way. No not an orgasm proper but my body closing down due to over stimulation.

It was as if he had seen this before as he told me to let my body go and if necessary he would hold me up. He was behind me as my body gave in having experienced a level of pain and pleasure at the same time that I had not thought possible. I sensed him lifting me off the Sybian and lying me on the floor. As I came round he was beginning to clean up and tidy away the toy that had brought me so much pleasure.

"Before you put that away I want you to give me one last treat."

His look was questioning but he said nothing until I added,

"Sit on it."

He roared with laughter before he asked me to confirmed that he was to take the phallus into his bottom. I was next to him before he lowered himself down onto the cock that I had set vibrating. His own cock was growing fast and I wanted to feel the final stages of this growth in my mouth. He was fully erect before I removed my mouth and used my hands instead. His balls were firm as I teased them with my fingers as my thumbs played behind the head of his erection. I varied the use of my fingers hands and mouth until I sensed he was past the point of any control. I knew exactly how I wanted to receive his cum. I took just the head of his straining cock in my mouth and found the sensitive point with my tongue. The final expansion of his cock signaled the first squirt that filled my mouth. At least six more followed before his erection felt like someone had stuck a pin in it. I carried on sucking away until I knew that it was painfully over-sensitive before I released it and allowed him to dismount.

When we had recovered slightly and we had dressed (except for my panties which he asked if he could keep) he told me there was a permanent position going in the company and asked me if I was interested. I said I had had the most wonderful week but I was going to decline the offer. He asked me why and my reply caused him to laugh,

"My pussy could not possibly stay the course."

All these years later I saw an advert for a job as Bob's secretary, or maybe it was for a secretary for his son (also Bob). I was very tempted to see whether my daughter was interested in applying for it. That week years ago had taught me so much. It had initiated interests in certain sexual things that I have developed since. Finally it has created many memories that have been a source of masturbatory fantasies to this day.