Journal—Week 7
Monday 13th July
I arrived at work nice and early to show that I was keen to do a great job.
Like last Friday I did not want to crease my clothes, so I quickly folded my skirt and blouse and put them on my desk and sat down to work. It does feel a little strange to sit there wearing only my high heels, but Mr. Wilson was right that as an executive trainee I need to think about the company first and foremost rather than my own concerns.
I wanted to show Mr. Wilson the research papers I had written over the weekend, to find out his opinion of my conclusions. However, he was on the phone and I had to wait a couple minutes.
When he finished his phone call, I quick caught his attention, held up my weekend research papers, and asked if he would look at them. Mr. Wilson said that he would, but he was busy at the moment, needing to write down a couple notes from the phone call while it was still fresh. I should have brought the papers over to his desk and stood there patiently waiting like I usually did, rather than interrupting his train of thought immediately after an important call.
I nodded, mentally kicking myself. Of course I needed to stand quietly beside his desk until he had time to give me his attention. That was part of the arrangement for sharing an office with Mr. Wilson. His time was more important than mine. I felt awful for screwing up like that.
He said I might as well stop wasting time and hand over the papers. His tone sounded impatient and annoyed. Wanting to please him, I quickly did as he said. I stood up and stepped over to his desk, holding my papers, ready to hand them to him.
However, he had turned briefly to his notepad and was writing, presumably jotting down those last few notes from his phone call. So I stood beside his desk and patiently waited for him to give me his attention.
I had not bothered to put my clothes back on since I was in a hurry and it seemed foolish to waste time getting dressed just to hand him some papers. I had not really expected it to take him so long to take them from me.
Waiting for him to get to me, I felt terribly embarrassed to be standing there totally naked. It is one thing to take off my clothes at my own desk, so they do not get creased. It is another thing entirely to stand beside my boss’s desk bare naked. I must have blushed deeply in embarrassment as I waited.
After a couple minutes Mr. Wilson looked up at me with a disarming smile that immediately put me at ease and I knew that he was pleased with me. I felt so relieved. He asked what the papers were about.
I explained what I had done at home over the weekend. He told me it showed excellent initiative and he was very pleased that I had spent my own time working on the project. It felt so good to hear his praise.
I had planned to get straight back to work, but he was so pleased that he wanted to read my research papers right away and he asked me to stay where I was in case he had any questions.
I certainly felt embarrassed then. But Mr. Wilson did not seem to have any problem with me standing there naked beside his desk. I guess I am just a bit shy and silly. Why worry about such a small thing like that? I have a bit of a way to go I think, but I am getting there. I know that I am. After all, I would not have had the confidence to stand there like that before Mr. Wilson began my training. I just know that I am going to be an excellent executive.
As he read through my weekend work, I was nervous about what he thought of it. But he idly rested one hand on my leg behind me, just beneath my buttocks. As he read, he gently stroked the back of my thigh, as a nice gesture to comfort my worries. He mumbled happy sounds, seeming pleased with my work, and I found myself relaxing.
Perhaps it was his hand caressing up and down my smooth skin, or the acute embarrassment of the situation, but I found myself relaxing into one of my naughty daydreams.
I imagined what it would be like if he casually told me to be a good girl and open my legs for him. Of course a good trainee would obey his order, so I stepped my legs apart. This naturally caused his hand to slide just a little further up my thigh.
He was now rubbing so very close to my crotch, and that sent a thrill up and down my body. I even leaned forward a little bit, pushing my butt back into his gentle stroking hand. I hope he did not notice.
His touch, so close to my intimate areas, fueled my fantasy. In my imagination he turned his hand slightly to cup my most sensitive parts from behind. Just the thought of that made me so very aroused, and I could feel my wetness. I imagined that he told me to lean forward futher, bend over, and lay across his desk with my butt up in the air. It was such a wonderfully submissive position, and one I had fantasized about many times lately both at work and at home, especially last weekend. I think I actually leaned forward a bit, just imagining being in that position.
I imagined myself bent over his desk nude, legs wide apart, slowly rocking back and forth as his hand groped and fingered me from behind. Oh how I wish that Mr. Wilson would want me in that position in reality. Maybe he would pick up on it if I dropped some hints.
I suddenly snapped out of my fantasy when he finished reading and put down the papers. His hand was still gently rubbing just beneath my butt, so close to the wetness on my thighs. He told me that he was very impressed, that my work was very insightful and showed a wonderful attetion to detail. I felt good that he was pleased, but I also wondered if he could tell how incredibly aroused and wet I was.
Then we discussed the contents of my papers. He asked lots of intelligent questions and I hope I gave him good answers. He seemed pleased in any case. He asked my opinions and thoughts on submissiveness, I guess to see whether I really understood the material which I had written about.
Then he asked me a very embarrassing question, especially since I was standing there naked and wet. He asked whether I had ever had any submissive fantasies. I expect that he wanted to know so that he could determine if I was “qualified” to write a paper on the subject and thus how valuable my conclusions would be. Still, it was humiliating for me to tell him that I had indeed had some submissive fantasies.
He asked question after question and before long I had told him how I had never considered any form of submissive fantasy before finishing university, but that they seemed to be the only sort of fantasies I had now. I was so embarrassed to be telling him this, but it was clear that it was important to the project and I had to put aside my insecurities and embarrassment.
It got worse though when he asked me if I had any fantasies about any people in particular. I reluctantly admitted that yes, I had indeed fantasized about someone in particular. He asked who it was.
I wanted to lie, but he has been so good to me, allowing me such freedoms, and I knew he did not deserve a lie, no matter how humiliating the truth.
So with great embarrassed reluctance, I admitted that I had fantasized about him dominating me. I even elaborated and told him that I had just moments ago fantasized about bending over in a submissive position while he touched me. I was so mortified to be telling him about my fantasies, but for some reason I could not stop myself.
Of course he was so great about it. He was not disappointed or disgusted by my fantasies. We had a nice long chat about it and he set me straight.
It was so cathartic to let it all out. Now as I write this I feel a bit silly that I did not confide in him earlier.
I had been so worried and embarrassed that I had been having these feelings for Mr. Wilson. But he explained that they were completely normal.
He is my mentor and a figure of authority in the company and so I was of course focusing my submissive desires on him. I needed to fantasize about a dominant man and he fit the bill in my subconscious mind.
He explained it was a completely natural behavior, and he would not judge me or my desires. I felt so relieved and thankful.
Of course, he explained, many young women, and especially intelligent professional women, have these powerful submissive fantasies. And further, that is what Penelope’s Pleasures was all about—helping people like me, he said, to explore our sexual desires.
He said that he thought I would probably have fantasies about any man in a position of authority over me. That was completely natural for an intelligent and healthy woman who had learned she enjoyed submission.
He told me that he thought it was because I was natural executive material. A good executive puts their company first, over and above their own desires and needs. An executive is the servant of their company, and does whatever is necessary for the good of the company. I wanted to do whatever I could so that the company would thrive. That just proved that I had exceptional executive potential.
He repeated this a few times. Well, quite a lot actually, so that I could get my head around it properly. I am glad that he did.
It all made perfect sense once he had explained it to me. I realized that he, as its leader, was essentially the heart and soul of the company. I wanted to serve as a good executive, and so it followed that I would want to serve him as he was the embodiment of the company. So it was quite natural of me to dream of submitting to him, so I could do the very best possible for the good of the company.
I cannot believe that I had not worked that out before. But now that I know it, I am much more comfortable with my fantasies. I know that they are normal and indeed reinforce that I am executive material.
We spent much of the day discussing my paper and my embarrassing fantasies. The time just flew by, it certainly did not seem anywhere near that long.
In the end Mr. Wilson declared that I had done very well and was a good girl. A strange shiver went down my spine and I felt a wonderful welling up of pleasure as he told me that. It is great that he thinks I am doing so well.
Indeed he told me that he thought it would not be very long until I would be ready for a new challenge. He hinted that it would be a very important promotion. I just know that my extra work over the weekend would pay off and I think it is going to pay off big time.
I think that as a little reward for myself I am going to indulge myself for the rest of the evening. I know that I deserve it, and besides I have not been able to get that wicked fantasy out of my head all day, of me standing by Mr. Wilson’s desk in that submissive position, pushing back into his hand. I am going to enjoy myself thinking about it this evening.
Tuesday 14th July
Not too much to write about today. It was a good day, I got plenty done in my research and Mr. Wilson seems very happy with my progress. He said so on a number of occasions today.
I have nearly finished through all the material on the sites for which Mr. Wilson purchased me access. Probably I will only need a few more days before all my research is complete. That will be a bit of a shame since this task has been so stimulating.
I think I will miss this project. I expect that my next task from Mr. Wilson will not make me so aroused. So I suppose I will not get to remove my clothes. The wicked part of me is going to miss being naked, since I think that Mr. Wilson is finally beginning to think of me sexually too.
I noticed him a couple of times today watching me as I brought myself to orgasm. It was extremely thrilling to masturbate with Mr. Wilson glancing my way every now and then, particularly when I had to moan and gasp out loud in the throes of my pleasure.
In previous days I had tried very hard to be discrete, to hide my moans when I masturbated at my desk, I suppose from shyness. But lately it has felt so good that I cannot help myself, I am getting louder and louder. I am helpless to cry out in pleasure, and even though it embarrasses me, I feel such a thrill that he knows just how tremendously aroused I am.
Wednesday 15th July
Another good day. I am really getting into the freedom that Mr. Wilson is granting me by allowing me to remove my clothes to keep them from creasing.
I just love being able to spend time naked. it is so nice not to have to wear uncomfortable clothes except when necessary. I only need to get dressed for the journey to and from work and while I walk in the building to Mr. Wilson’s private office.
It feels so good to be able to sit at my little desk in the nude and have the ability to masturbate if I become aroused while doing my work.
This morning I was watching an especially hot video and taking copious notes. The video portrayed a strong-willed young woman who was tamed by a powerful man. He stripped her and humiliated her and she found herself enjoying being his slut.
I became increasingly aroused by the video and could not stop myself from playing with my clitty. I guess I made quite a bit of noise, especially so when I could hold back no longer and finally came with a wonderfully powerful orgasm.
When I recovered Mr. Wilson had a frown on his face. He told me that I should contain myself a little. I had been so loud that I had disrupted his concentration. There has to be boundaries at work, particularly when it affects my colleagues. While he is happy for me to express myself, when it becomes disruptive it causes problems.
I was so sorry I had distracted him from his work. I had been so selfish. I am embarrassed to think that I was thoughtless enough to disturb him with my orgasm.
Of course, he had to punish me for my error. I admit I was excited at the idea, quickly laying myself over his lap. I am growing very accustomed to that position.
This was my first spanking where I was naked, and somehow that made it even more arousing. As he smacked my bottom, my breasts jiggled beneath me, oh it was very exciting. I did not really feel much pain either. I suppose from that respect the punishment is not working particularly well.
In fact, while he spanked me, I let my thoughts drift to a naughty fantasy. I imagined that between spanks he rubbed his hand between my legs. Sometimes he would rub around my clitoris and other times he would dip a finger or two inside me. I cannot believe that I allowed myself those fantasies while I was supposed to be getting punished. I felt incredibly aroused, but in my fantasy he did not allow me to cum. I knew it would be inappropriate to orgasm while being punished for orgasming!
After my time standing in the corner, we had a nice chat about my orgasms and I now see that I have to be careful not to disturb him in the future.
We agreed that it might be better if I was a lot more careful about orgasming at work. In particular, since he is the one whose time is most valuable to the company that I really need to fit my cums in around him. So in the future I will ask him permission before I cum, so that he can pick the most appropriate time when he will not be disturbed. It made sense after he explained it to me.
It is just one more sign, he said, that I was becoming a great executive. I would be giving up control of an important aspect of my life to a more senior executive all for the good of the company. I felt so proud that I was demonstrating my aptitude for a senior position.
Mr. Wilson also suggested that it might help me become accustomed to the idea if I made it a routine and applied it to orgasms outside of work too. That would help me to fall into the habit faster. To facilitate this, he told me that it was fine for me to phone him at any time to ask for permission, whenever I needed to cum. He is such a great man, willing to allow me to interrupt him outside of work, to help me out.
Though when he first mentioned it, I felt rather embarrassed at the thought that he would discover just how much I have been masturbating at home. His idea made a lot of sense and I did want to do my best for him, but I wondered if it truly would be necessary.
He reminded me that when I was very aroused just before an orgasm I always found it hard to concentrate. I guess I had never thought about it before, but it is true. He is very wise and observant. He explained how that difficulty in concentrating might cause me to slip up and inadvertently distrub him. So by making it a habit to ask for permission every time, I would learn faster how to prevent embarrassing myself by losing control and cumming without getting his permission first. That made sense, once he helped me understand it.
Well, I made sure that I got started with the habit right away. My research continued with more videos in the series about that strong-willed girl who was humiliated into submission and as she was subjected to more and more sexual encounters, I grew more and more excited myself. I had to ask for permission twice during the rest of the morning, and three more times in the afternoon, and I must admit that the pause while I waited for Mr. Wilson to say ‘yes’ somehow made the pleasure, when it did come, so much stronger.
It is hard to explain, but I loved it when Mr. Wilson exercised his control over me. I know it was simply done so that he would not be disturbed by my moaning. But to me it felt wonderful to know that my orgasm was tied to his approval. I just know that it will drive my fantasies tonight.
I am about to log off the computer now, and head into my bedroom for some playtime. I must admit that I am getting excited, and at the same time embarrassed, just thinking about the fact that I will most likely have to phone Mr. Wilson later tonight.
Thursday 16th July
I did indeed have to call Mr. Wilson last night, and he was very understanding. I was terribly embarrassed and unbelievably aroused. I had tried my best to survive without having to phone him, but I just could not hold off. I had worked myself up so much thinking about how embarrassing it would be if I rang Mr. Wilson for permission and that combined with my submissive fantasies to drive me wild.
I could not keep my fingers from my hungry pussy. It was driving me crazy. So finally, late at night, I buckled and picked up my phone.
Oh it was so humiliating waiting for him to answer knowing that I was going to have to ask him for permission to have an orgasm. The worst part though was that when he did finally pick up, I blurted out my desperate plea even before he had said hello.
He was so good about it, he just said “yes of course my dear” and as he did I was overwhelmed and had such a fantastically strong and powerful orgasm. Wave after wave of pleasure crashed over me. As I recovered I could hear Mr. Wilson; he was still on the line! Oh it was embarrassing to know that he overheard me screaming and moaning. He was saying over and over “good girl” and “let it all out”. He is so caring.
Anyway, I woke up this morning tired and very horny. I considered phoning him first thing and asking for permission to orgasm again but I just could not bring myself to do it. I still had not really recovered properly when I got to the office this morning.
And oh god, it has been such a frustrating day!
We were so busy today it was unbelievable. The client phoned us first thing in the morning and they wanted Mr. Wilson to get them a report by the end of the week. So he has been snowed under with work all day.
Alongside that he needed me to pull together comments on some new videos and stories. It turned out these were even more exciting than any I had seem yet so far. Which of course was a problem! Plus I was already incredibly aroused, even from before I came to work. As usual, while I researched, I masturbated. The new material was just so hot!
Anyway, Mr. Wilson was so busy that even when I got really close to cumming and had to ask him if I could, he just told me to hold on. He could not be disturbed then.
I felt so sorry for him, since he had to work so hard. I knew that I just had to grin and bear it, but it was so so frustrating to be denied. But at the same time it also felt very good, since it gave me a warm feeling inside to know that Mr. Wilson was in charge even if it meant I could not cum right then. I knew that when at last I do cum, it will be a mind melter.
With the overwhelming workload, he even had to work through lunch so I got no respite then either. I only asked him when I was really desperate, but each time he was not able to let me disturb him. So I remained on edge throughout the afternoon too. By the end of the day my mind was buzzing. And to be honest, it still is.
He was still busy at work when I got dressed before leaving. Oh my poor nipples felt so tender as they rubbed against the inside of my blouse. I hate having to put on my clothes at the end of the day, I wish I could be naked all the time. Then he told me that he expected to be working at the office all evening. He is so dedicated. But of course that did not solve my problem.
So I sit here at home, naked as usual. My nipples feel so sensitive and I have touched my pussy almost constantly all evening. I have had a hard time trying to concentrate, I am just so horny. I know that I cannot disturb him at work this evening but I need to so badly. I hope that Mr. Wilson will have a few moments tomorrow to be able to give me permission to cum. I just do not know what I will do if he does not.
Friday 17th July
As with yesterday I was very frustrated since Mr. Wilson was so busy he could not grant me permission for an orgasm. It felt ten times worse today. I was on edge all the time and could not keep my fingers out of my pussy. I felt so horny, and got so wet that I stained my chair with all the fluid I leaked onto it. I am not sure how I managed to keep myself from cumming but I did. Later Mr. Wilson told me how proud he was of me for not disturbing him and that made all the frustration worthwhile.
It was not until the late afternoon when Mr. Wilson finally delivered his report to the client. They were so impressed that they approved the next phase of the project. I will find out more about that on Monday.
Anyway, by the time Mr. Wilson finished his report and emailed it off, I was crazy with frustration. I could hardly concentrate my mind was swirling so much with naughty horny thoughts.
Just before he mailed off the report, I had put my clothes back on and popped out to grab him a tea. He deserved a stiff drink but we did not have any alcohol in the office and so a cup of tea would have to suffice.
Back in his office with the tea, I quickly shed my clothes again. It felt so good, so free, to be nude again. As I gave Mr. Wilson his tea I do not know what happened, my thoughts were so distracted, but I knocked the tea over and spilled it across some papers on his desk. He leaped back and told me to be more careful.
Of course my mistake had to be punished, so in a few moments I was bent over his knee. It felt so good to be there naked while he spanked me, even though I felt terrible for having spilled the tea.
I could not avoid thinking about the naughty fantasies swirling around my head and coupled with my frustration I was soon moaning and squirming on his lap. If there was any pain from the spanking, it was completely eclipsed by the boiling pleasure suffusing my whole body.
Time seemed to strech out. I am sure this punishment lasted longer than my previous spanking sessions, but my mind was not really working properly. Perhaps it lasted no longer after all.
To my embarrassment, as the spanking continued, I began to ask repeatedly ‘please may I cum?’ I was so desperate. But he kept telling me ‘not yet.’ I was being punished and so I did not deserve an orgasm. Of course he was right, but I was in a complete state of desperate arousal. Tears flowed down my cheeks and I was babbling in my need for an orgasm.
Eventually my justly deserved punishment came to an end and I fell to my knees sobbing, partly apologizing and partly pleading. Honestly, I do not know how I managed to get through it all, but I guess it was because of Mr. Wilson. He was so supportive. I know he was punishing me to help me improve myself.
He undoubtedly could clearly see how aroused I was as I knelt there naked besides his chair recovering from my spanking. I thought about looking up at him and putting on my saddest puppy-dog face and begging again if I could cum, but I knew I would probably be denied again. Oh god I felt so desperately horny and frustrated then. I knew then that when I finially did get to cum, it would feel so mind-bendingly good I would do just about anything.
Mr. Wilson looked down at me and ruffled my hair kindly. What a sweet man. And he told me if I was a very good girl then he would give me permission to cum. Of course, in my desperation, I promised him I would be good. And I do hope that I can be, so that I can do my very best for Mr. Wilson and the company. But honestly, right then, I would have done anything to get an orgasm.
It was then that one of my deepest wishes came true.
Mr. Wilson told me that he was a normal, healthy man and that my moaning and squirming, and prancing around naked, had the expected effect on him. My heart soared. After all the fantasies I have explored, I had dreamt that he would find me attractive, desirable, and now it was clear that I was affecting him.
He told me that he could not do his job if he could not concentrate properly. So he offered me a deal. If I helped him relieve his tension then I could cum too. Oh it was just like my fantasies and I eagerly nodded.
Mr. Wilson undid his trousers and adjusted himself in his seat. I blushed as I saw his erection, as I felt a brief flutter of shy embarrassment, but the passion burning within me spurred me on.
I have never done it before. I always felt it was dirty and degrading. But no matter, this was what I wanted more than anything. I gently took hold of his member and then gently took it in my mouth. Mr. Wilson has been so good to me and has taught me so much I had to do this for him. I wanted to repay him for all he has done.
I definitely was not very skilled, but Mr. Wilson was good about it. He told me what to do, offering advice and coaching. What a considerate man to make a special effort to teach me. I am nothing if not a good learner, so I did my very best to bring him pleasure. Soon I could tell I was having the desired effect and he was moving closer and closer to his own pleasure.
He told me I was a very good girl, that I was coming along very well and that I could masturbate myself while I ministered to him. Of course he reminded me not be so selfish as to cum before he gave me permission.
Oh it was music to my ears! I reached down between my spread thighs and touched myself. I felt electrified. As my head bobbed up and down on Mr. Wilson’s beautiful dick, my fingers rubbed around and around my throbbing and tender clitoris. It all felt so wonderful, so powerfully pleasurable.
I was almost at my moment of crisis when I felt him tense and grip my head in his hands. Then his dick exploded, filling my mouth with his semen. As he orgasmed he told me to cum too. It felt so wonderful. After a couple days of pent-up desire, my orgasm felt fantastic. It crashed over me in waves. That was the best orgasm I have ever had, and it was even better because I knew that I had pleased Mr. Wilson.
I felt a strong connection with Mr. Wilson at that moment.
He was still gripping the back of my head, but more gently, stroking my hair. I had a big load of his slimy cum in my mouth and he told me I should not spit it out, since we did not want to stain his office carpet. That made sense, but I did not know what to do with the mouthful of salty sperm.
He stroked my cheek and told me to swallow it all like a good little girl. He also told me how proud he was of me and told me that he thought I was ready for another promotion. I was so pleased to hear that I had made him proud, and I still felt so blissfully happy from my pleasurable orgasm, that I did not mind swallowing his cum then. Besides I know it would have disappointed Mr. Wilson if I had not.
After that I needed several minutes to calm down. My orgasm had been so powerful that I felt like I was floating on bliss for awhile afterward.
We finished out the workday by discussing that promotion he mentioned. Mr. Wilson said that he thought I was ready for a real executive position. So next week sometime, he plans to officially promote me, and I will no longer be a trainee, though of course Mr. Wilson told me that I will continue to learn. Still, I will be a real executive with responsibilities. I am so excited!
Sunday 19th July
I had to phone Mr. Wilson several times over this weekend, to ask for permission to cum.
He is such a great man with the patience of a saint. Who else would be so willing to help me enforce the habit of asking for permission to orgasm so that I can learn to be a good executive?
Tonight when I called Mr. Wilson for permission, before I even had a chance to ask, he started talking about the upcoming week starting tomorrow, and about my upcoming promotion and new responsibilities. He sounded excited about the new project I was going to tackle. I was excited about it too, but at that moment I was torn.
I so badly wanted to cum, my fingers could not stop sliding around my hard little nub as I teased myself on the edge of orgasm. But at the same time, I did not want to interrupt Mr. Wilson as he was talking to me. I want to do good for him, listen and learn from him.
Mr. Wilson was telling me how I was being offered such wonderful opportunities, and would prove myeslf worthy as long as I could overcome the challenges of the new project. He gave me some advice and suggestions about how to approach the new week. I could listen to him giving out his pearls of wisdom all day. So I just relaxed and listened to him as I played with myself. His voice sounds so deep and smooth and wonderful, I could just drift away on it.
And then suddenly the conversation was ending and we had hung up, and I had not even asked him for permission which was the reason I had called in the first place! I was feeling quite frustrated on the edge of an orgasm, but I did not want to bother him by phoning right away again after we had just ended this call.
Even though I really want to cum again tonight, I think I can wait. I will have to hold on. I am going to force myself to wait until I am in the office tomorrow before asking him for permission again. Besides, I have discovered that my orgasms feel so much better and more powerful if I let my need build up a little before he gives me release.
I am so excited about tomorrow!