Manager to Mistress

I remember her saying at my interview. "This is an old-fashioned company; we believe in old-fashioned values and customer service." What she should have added but omitted was that she also believed in old-fashioned punishment. This is the story of my journey from having Charlotte as my boss to having Charlotte as my boss and Mistress.

I was delighted when I was offered the job as a regional sales representative for a specialist insurance company. The base salary was excellent and if I achieved quota the commission was even better.

My boss is Charlotte Goddard. She is one of the best sales professionals I have ever met. Her customers love her, she is a great sales coach and drives her team hard. Although she lets her team have fun, we all know she is the boss and that we are expected to work hard. Charlotte is in her late thirties or early forties she has a lovely figure and does look after herself. I have seen her when presenting to major clients and when she is dressed to impress, she looks stunning. I am in awe of her, and I must admit I am very much in lust with her.

I did well for my first six months. I build great relationships with the rest of the sales team and was generating new business with our existing clients. I would like to think Charlotte was impressed. She did however keep encouraging me to build relationships with some new clients just in case of trouble ahead. Although I had the best of intentions, I did not manage to do this before trouble came. One of my major clients did not renew a contract as expected and I failed to hit my quota as a result.

During my time at the company, I had seen two salespeople dismissed for poor performance and I was really worried the same was going to happen to me.

Charlotte said she wanted to see me in her office at six o'clock that evening after everyone had left for the day.

At six, I knocked on Charlotte's office door and was told to enter.

"You asked to see me," I said.

"Yes, can you guess why?"

"I would imagine it is regarding the lost contract. I am sorry I did everything I could."

This sounded a lame excuse even to me.

"Really? You have done everything? How many new customers have you bought into the company?" Charlotte did not shout but I knew she was not happy.

"None," I stammered.

"So, you missed your quota and have not tried to win any new business is that the case?"

"Yes. Look, I am sorry I will work extra hard next month to fill the shortfall."

"I think it is a bit late for that we will have to let you go. You do have the makings of a first-class sales professional, but you are lazy. Business does not just fall in your lap you have to go and win it."

"Please, it is the first quota I have missed can you not reconsider?"

"So just let you carry on and hope you will do better. I am not sure that is a good idea. How do I know anything would change?"

"I will do whatever I need to do." I was pleading but I did really like the job and I had not worked as hard as I could, but I did want a second chance.

"That is a big promise. You will do whatever you need to do. You really mean you will

do what it takes?"

"Yes, honestly." I had no idea what I was getting myself into.

"Look, I like you. You have the makings of a good professional salesman, but you need to buck your ideas up. Let me think of some alternatives, see me here at the same time tomorrow. I can make no promises. There do have to be consequences for your actions."

I was so relieved that there was a chance for me not to lose my job I did not register what was being said. The next day, Thursday, was a nightmare. I did not sleep well the night before and could not settle at work. I kept thinking about the forthcoming meeting and what was going to happen.

Eventually, at six o'clock, I found myself again knocking on Charlotte's door and nervously entered when told to do so. I did not know what to expect but nothing had prepared me for what followed. I walked up to Charlotte's desk and there was a crook-handled cane. I could not believe what I was seeing. I do not look at a lot of porn on the internet but when I do, I am drawn to spanking sites especially sites where women are spanking men.

Charlotte looked at me. "Do you know what this is?"

"Yes, it is a cane," I stammered although a part of me was starting to get excited.

"What is this used for?"

"Traditionally to punish people." I was still stammering.

"Yes, those people who have not done as they were asked and have been a disappointment. Do you fit into that category?"

"You cannot mean to use that on me." Although these words came out of my mouth, I was starting to understand the situation.

"You have a very simple choice. Either you accept your punishment, and you will be caned by me tomorrow evening or you leave the company. Your choice."

My heart was beating fast, and I am sure a was looking red and embarrassed. "What do you want me to do?"

"If you accept you should be punished, you will come to my office at six o'clock tomorrow. You will then receive six strokes of the cane. Have you ever been spanked or caned?"

"No never," I replied honestly. I did not say that I had always wanted to be.

"Well, this will be quite an experience for you. So, punishment or dismissal?"

"Punishment."

"So, you will report here tomorrow at six o'clock."

"Yes."

"After your punishment, I will be monitoring your performance very closely. If I do not see a marked improvement, you will be looking for a new job anyway."

"I will do my best, thank you."

"Tomorrow at six, and you will receive six strokes on your bare bottom. Dismissed."

With that bombshell, I left.

That evening, I was in turmoil. There was a part of me that has always wanted to be caned. I had always wondered what it would feel like having to submit to the cane. But now I had the chance to experience my fantasy, I was scared. If I could have chosen someone to punish me Charlotte would be close to the top of the list. Would I be able to take the cane? Would I cry?

Needless to say, I did not sleep at all well, and at work on Friday, very little got done. I did see Charlotte a couple of times in the office, and she ignored me. Part of me dreaded six o'clock coming and part wanted to get it out of the way and another part was excited at the prospect of what was going to happen. At five o'clock, there was the usual Friday rush to the door. Charlotte and I were left in the office. I mentally prepared myself and knocked on her office door at the requested time.

The cane was on the desk waiting for me.

"No second thoughts? You want to go through with this?" Charlotte looked deep into my eyes.

"I have had many thoughts, but yes, I want to keep my job and if this is the price, I am willing to pay it."

"You will leave here with a very sore bottom and from next week, I wish to see a new attitude and approach to your work. You can be a very successful salesman you just need the right encouragement. That starts now."

I tried to swallow on a very dry throat.

Charlotte stood. "I want you to remove your trousers and underwear and stand before the desk. You will fold your clothes neatly on the sofa in the corner. I will be back in a couple of minutes. I want you ready when I return." She left me in the office.

This is it I thought. I undid my belt. Took off my shoes and socks. Finally, I took off my trousers and underwear. As requested, I folded them neatly. As I stood before the desk, I could not help but start to get an erection. Although I was very nervous, I was also starting to feel excited. I covered myself in a somewhat foolish attempt at modesty. It is hard to keep your dignity when you are semi-naked in the office with an erection.

Charlotte returned and sat down. "Hands at your sides," she snapped. "I see you find this exciting." She was looking at my erection as she said this.

"Yes, sorry."

"You like the thought of being punished?"

"Honestly, part of me does, part of me is terrified."

"Interesting," she said this last word with a very thoughtful look on her face. "So, you have never been caned?"

"No."

"Have you ever wanted to be?"

"I am not sure."

"I would expect that to be a yes or a no, how can you not be sure?"

"I have always had a bit of a thing about spanking but now I am here, I am not sure."

"Well, fantasy and reality can be very different, as this is your first caning let us make it memorable. I want you to bend over the desk. Spread your legs wide and push your bottom out. Off you go."

This is it; I was going to be caned. I bent over as instructed and opened my legs.

"Your legs need to be wider than that."

I did as instructed.

"That is better, push your bottom right out I want you to offer yourself to the cane. It will have more effect that way."

I felt so exposed here I was displaying everything before my boss, who was holding a cane she was about to use on my bottom. My penis was stiffer than ever, and I am sure she could see this as well.

"Right, you will stay in that position. This will be painful, but I expect you to take this without too much fuss. If you shout out or move too much after a stroke, that stroke will be repeated, and I am sure you would not want that to happen. If you swear at any time, we will start the caning from the beginning. Is that clear?"

"Yes," I was now really scared. Would I be able to stay still? Would I get extras?

Charlotte walked to stand in front of me. She was flexing the cane between her hands. "You only have yourself to blame. I am going to enjoy showing you the error of your ways."

She looked stunning there is something about a fully dressed dominant woman especially when you are semi-naked, and she is holding a cane. This is normally the stuff of fantasies.

However, in fantasy, your bottom did not get caned.

I heard Charlotte walk behind me. She placed the cane in the centre of my bottom and gently tapped me there.

"Here we go remember to stay still."

With that, she withdrew the cane. I heard a wump sound and the cane returned to my backside with force. Nothing can prepare you for your first stroke of a caning. It hurt more than I could have imagined. My hands flew to my bottom to protect myself and I shouted out.

"Right, that stroke does not count. You must stay still and quiet. Let's start again. We could be here all night at this rate."

The second stroke was the same as the first, but I did manage to stay in position but only just.

"That is better, five to go."

I could feel the two lines of pain decorating my bottom, tears had formed in my eyes.

I never believed it would be so bad.

I made it through the next two strokes. But I shouted out after the next.

"That will have to be repeated. I will add penalty strokes if it happens again."

Charlotte's voice showed no sign of mercy.

I managed to take the next strokes until Charlotte said, "The last one coming up, do you know anything about the tradition of the last stroke?"

"No," I replied honestly.

"Well, traditionally, it is the hardest stroke it is the one you will remember tomorrow. I am a great believer in tradition. After the stroke, stay in position until I tell you otherwise. Is that clear?"

"Yes," I could not believe she was being so cruel.

The cane rested at the junction of the top of my legs and the start of my bottom. I knew this was going to be bad.

"One more and it is all over," Charlotte announced. With that, the last stroke whistled into my bottom. I cried out and stamped my feet but managed to stay in position.

The fire in my bottom centred upon the stroke I had just received.

Whilst I was getting some composure back, Charlotte had put the cane back on the desk and walked to stand behind me. I could feel her bending over to look at my battered bottom.

"That does look like the bottom belonging to a very naughty boy."

She traced her finger along a couple of the stripes I had no doubt were present on my poor behind. "We do have some lovely marks you can inspect in the mirror later. So now you know what happens to naughty boys. Are you going to pull your socks up and perform now?"

"Yes, I will try."

"We are going to meet every Wednesday to discuss progress, and if progress is not satisfactory, we will meet every Friday and do this all over again. Now get dressed and have a nice weekend. I will lock up the office in ten minutes."

She left and I slowly levered myself upright. I reached out to massage both of my bruised buttocks. My bottom felt swollen and hot to touch. Mindful of the time I dressed and drove myself slowly home. Once there, I went straight to the bedroom and dropping my trousers looked at my bottom in the mirror. Eight clear stripes faced me. The pain was starting to ease, and a warm throb was replacing the intense pain. I was becoming aroused and sought relief with images of Charlotte wielding the cane filling my head. I brought myself to a very intense orgasm.

Throughout the rest of the weekend, I could not help thinking about what had happened on Friday. I regularly inspected my healing bottom. The experience had been very painful however it was also highly erotic. I did not want to rush to do it again however I did want a repeat at some stage.

On Monday, I threw myself into work. I made more calls and chased more leads and was more productive than I had been for a long time. When I bumped into Charlotte, it was as if nothing had happened on Friday. She was her usual self.

On Wednesday after work, Charlotte was full of praise for my efforts and proved to be a great mentor. We worked through my client list, and she offered advice and encouragement. At the end of the meeting, I felt like the boy who got a gold star at school. My performance continued this way for the next few weeks and the results started to show in the amount of business I brought into the company.

At the end of one of the Wednesday evening sessions, Charlotte said, "You enjoy running to keep fit, don't you?"

"Yes," I replied. "I have been running for many years and generally try to keep myself in shape."

"Do you fancy joining me on Saturday for a five-kilometre run? My gym is organizing the event and guests are welcome."

"That would be great. I would love to?"

"Do you fancy a wager?"

"What sort of wager?"

"If you win, you get to cane my bare bottom and if I win, I get to cane yours?"

"You are on," was the immediate reply I had given no thought to the answer but knew whatever happened, it was a good bet.

I did not see Charlotte the next day. On Friday, Charlotte dropped an e-mail with the address of the gym, asking that I arrive at nine-thirty the following day.

I met Charlotte as arranged and she signed me in as a guest. We went to get changed and agreed to meet outside in ten minutes. Charlotte looked stunning in her running gear. I always thought she had a great figure now I knew this for certain. She had Lycra running pants and top and looked the image of a seasoned runner. I was beginning to feel that I might be in trouble winning this race.

We were joined by several other people who were going to take part. Whilst we waited, we chatted about running. Charlotte, in her youth, had run at county-level and just missed running for the national team. She ran now only for pleasure, but she did take the sport seriously. I now knew I was in big trouble; my running was only at an amateur level and a low amateur level at that.

Once the race started, Charlotte took off. I tried to keep pace and the view of her bottom did keep me fully engaged. However, after ten minutes, the pace was too much, and Charlotte drew ahead. Although I finished in a respectable time, Charlotte was easily the winner.

She walked up to me whilst I was recovering. "Looks like I won the bet. Someone is going to have a sore bottom. I am going to change. Do you fancy a coffee? I will see you in a café."

I would have loved the opportunity to cane Charlotte but even so, I was excited to be punished by her again. I changed and over coffee, Charlotte said, "I have to go into town and buy a couple of things. Do you want to tag along, and we can do lunch?"

My heart skipped not just one beat but several. "Yes, that would be great."

We left our cars at the gym and walked into town, conversation flowed easily and after fifteen minutes, we found ourselves in the centre of town. As we walked past a lingerie shop Charlotte announced. "I just want to pop in here, come on you can help me."

I could not believe what I was hearing but followed her into the shop.

Once inside, Charlotte headed for a rack displaying stockings of various designs.

"I do think stockings look so elegant on a woman, don't you agree?"

"Yes," I stammered. I could not quite believe what was happening.

"Which do you prefer the dark chocolate or the midnight black ones? I cannot decide."

"I like them both but if you pushed me black is good."

"All men are the same. I think I will buy both. I have some black stilettos that would go nicely with both. Do you like stockings and stilettos?"

This was like asking a fish if it liked water. "Yes, definitely they certainly do show legs to perfection."

"Men are such simple things," she said with a smile on her face. "Let me get these and we can go for lunch. Do you like Italian food?"

"Yes, Italian is my favourite"

We went to a small restaurant tucked away from the high street, Charlotte said she had a reservation for two and we were shown to our table.

"How did you know to reserve the table?" I asked.

"As I said, all men are the same. I knew you would accept." Charlotte smiled.

The food was lovely and over the main course, I was asked, "So, you like stockings and heels. I wonder do you prefer lace or latex?"

"I'm sorry what?" I started to blush a shade of red.

"I asked what lingerie you prefer: lace or latex?"

"Well," I then had a long pause. I decided to be honest. "If I was going to live out a fantasy it would be latex."

"That is very kinky. So would you like me to wear stockings, heels, and latex lingerie?"

"That would be wonderful, yes." There was no hesitation this time.

"If I do that your punishment due would have to be significantly increased. What do you think?"

"Yes, I think that would be a good idea." Again, I was speaking before engaging my brain in this conversation.

"So, a severe punishment from me, basically dressed as a dominatrix, is that what you are asking for?"

"Yes," again no hesitation.

"I will see you tomorrow late afternoon at my house and your wish shall be realized."

My brain finally caught up with the conversation. "Great." I suddenly had a very dry mouth. I was given Charlotte's address and told to arrive at five o'clock the next day. We walked back to the gym mainly in silence, I was lost in my thoughts. Very exciting thoughts, I must admit.

Just as we arrived back at the car park Charlotte said. "One other thing: could you shave down below? I do like a naked man to punish." With that bombshell, she left me to my thoughts.

The rest of the day passed in a blur. I could not focus on anything. I watched mindless television and went to bed early only to find I could not sleep. In the morning, I carefully prepared myself I took a long bath and shaved for the first time below the waist. It took a long time as I wanted it to be done perfectly for Charlotte. I looked at myself in the mirror and thought how strange I looked, somehow even more naked than usual.

Time dragged until at five o'clock I found myself knocking on Charlotte's door. She lived in a period detached cottage in an up-market area of town. It reflected her business success. I was not sure what to expect but Charlotte opened the door dressed in jeans and a sweatshirt.