Pleasing Sir

I looked again at the clock in the room. It was 3.47 pm, two minutes from the last time I looked. For the 10

th

time I wondered how I came to be here in the bedroom of the drab Holiday Inn on the outskirts of this drab town. The short answer was that Sir had told me to be here.

He had told me to arrive at the hotel after 3.00pm, and he would arrive at 4.00pm. The room was prepaid in the name of Jones, a common enough name that would not stick in anybody's mind. These details answered the practical question of why I was here, but they did not answer the big question. What was I doing here?

Logically it made no sense. Why would I be here for a man that I had not even met in person before, waiting for sex with him where he would dominate and subjugate me and do whatever he wanted with me. The desire to run away out of the room flashed through my mind again. The adrenaline of the flight reaction raising my heartbeat again, but I did not move. I realised I had wanted this for so long, had looked online for the right Master to explore my desires, and believed I had found him. I kept returning to this one fact that I had found the right person, and if I ran away now, I would never do this.

I knew that this was more than just sex. If I wanted sex I could get that easily by visiting the bar in one of the endless hotels that I used for work. I would sit at the bar with a glass of white wine and wait. It never took long before a man came up to ask if I was waiting for someone or would I like company. I would look them up and down, and unless they were particularly ugly or crude, I would smile and accept their offer of another glass of wine.

My routine was that I would visit the bar on the last night of my stay. I wanted sex but I did not want the awkwardness of telling the man that I only wanted a one night fuck. So much easier to be able to say truthfully that I was going home tomorrow. We would have a drink in the bar and then the man would always ask if I wanted to go back to his room. There we would enter the room, kiss, fondle, rapidly discard clothes and have sex on the bed. If he was good then we would have round two and then when he was satisfied and dozing off, I would make my excuses and dress quickly.

I always pleaded an early start and a meeting with my boss in the morning. The businessman would reluctantly accept that he was not going to get sex again in the morning and I would slip out of his room to take the walk of shame back to my room, my knickers in my bag.

The sex scratched an itch, but it did not scratch THE ITCH. I would shower when I got back to my room, but I would be thinking "What if?" What if I found a man where I was not the one calling the shots, where I could not just walk out when I wanted to? What if I did not want to walk out. This what if always got my fingers sliding down my body in the shower, taking the familiar route to my waxed pussy with a toe curling orgasm whilst leaning against the wall of the shower following shortly after.

This was the reason that I was in this anonymous hotel room and this was why I did not run away. I wanted this and had done for so long. Adrenaline surged through me again, but this was different, this was from sexual desire and the thought that my deep wicked long held desire was close to being fulfilled. My nipples were erect and my knickers were damp. I was ready.

As I paced around the room in my business attire, waiting for the clock to move to 4.00pm, I looked at the blindfold on the desk, an eye shade from a transatlantic business class flight that I had been instructed to bring along. This brought a shiver of desire to my body, anticipation of the handing of control over to Sir when he arrived.

It had all started from a visit to a chatroom on my laptop. This had been one of the midweek hotel stays where I was not going home the next day, so a trip to the bar was not going to happen. I was however feeling an urge, an urge to find some stimulation and maybe some pointers towards scratching THE ITCH. I had eaten in my room and had demolished most of the bottle of Sauvignon Blanc that I had ordered with the meal. My inhibitions were loosened with the alcohol. I lurked on the board for a while, reading the private messages that came flooding in, but not responding to any. Amused by the lack of intellect in the approaches, I explored the site further. I noticed that there were 'specialist' rooms within the main chatroom. I clicked on the BDSM room and waited.

A desire to explore BDSM had always floated around at the very back of my mind. I had never done anything about it apart from noticing the response of my body when one of my lovers would slap my arse as he fucked me from behind. The Sauvignon Blanc had finally taken me past my resistance to explore my desire. I knew that I was setting off down a dark road to an unknown destination, but the alcohol gave me the courage I needed.

That first night, I had my first role play. It was a fairly basic story of a woman being picked up in a club and taken round the back of the club where she did as she was told, sucked his cock and then bent over as he pulled her skirt up and fucked her from behind. What elevated it above the tawdry was his demand to be called Master, and the fact that she had to thank him for his demands. This lit up a light in me that I did not know exist, and I rubbed myself to a shattering orgasm as I typed "Thank you Master" as he spurted inside me.

I was hooked by the adrenaline of it and visited the BDSM chatroom often when I was away in hotels, and sometimes when I was at home. I became a bit more discerning about who I chatted with and what I chatted about. I would ignore the requests that had unrealistic scenarios, I was not in to castles and dungeons. I would put forward my own scenarios that always had a realistic aspect to them, a businesswoman away from home. They would then normally proceed in a variety of ways with varying degrees of control and punishment. The feeling of letting go and being controlled was a strong aphrodisiac and led to some really powerful orgasms.

Most men had additional requests. Did I have a webcam, did I do phone sex, did I want to meet up. I refused all of these requests. I was happy to keep it to the written word and let my imagination fill in the gaps. That was until I met Sir online.

His approach was different. He did not want to go straight to the scenario. He chatted and asked questions. What had brought me here in the first place and what fantasies did I like. What clothes did I wear. How often did I think about being dominated and how did my orgasms feel when I was chatting on this site. In fact we chatted for an hour without starting a role play. He then said that he had to go, but he knew what I wanted and that he was the person who could deliver an experience more powerful than I had ever thought possible. If I wished to explore that, I should be online next day at the same time to chat again. With that he was gone.

The next day was my last night in the hotel. I had a long day working in the department store. I was employed at head office and visited the stores around the country to discuss marketing campaigns, sales promotions, keeping the stores on their toes and sales up. Normally I would have visited the bar after my meal, it had been a couple of weeks since I last had sex. This day I ate in my room and logged on to the chat room again. A large glass of wine with my meal had calmed my nerves a little. After all I was just chatting online again, but deep down I knew that I was stepping on to a different path. Who knew where this one would lead.

I noticed his name was on the list of visitors to the BDSM board. I waited for him to message me, and waited and waited. Didn't he want to chat to me? Unable to resist, I messaged him. I said hello and mentioned his offer from yesterday.

"You are late" was his reply.

I was flustered by his reply. I had not expected that. I had expected that he would continue in the same vein as yesterday, talking about how he would help my dream come true. But this was a different side of him, Sir was here as my Master, and I had better get used to that quickly.

He set out the ground rules quickly. I must call him Sir at all times. I must ask permission before asking any questions and I must obey everything that he told me to do. I hesitated for a while but then found the courage to say "Yes Sir. I will do as you request."

He then asked me to describe why I wanted this. Could I put in to words why I wanted this? It came down to the fact that I wanted to be dominated sexually. I had a life that revolved around my job, where I was in a position of power, calling the shots, holding people to account, even firing them if they did not perform. I determined when I had sex and who with. I enjoyed this lifestyle, but THE ITCH was all about turning this upside down and experiencing being obedient, speaking when I was spoken to and doing what I was told. The thought made me shiver with a tingle of sexuality. I had never done anything like this before, but something inside told me that I would not regret trying it.

Sir told me that this would only work if we met up, it had to be a physical experience. I had wondered about having a voice chat or maybe even cam sex, but Sir was not persuaded. If I did not agree to meet up, he would terminate our conversations and I would never hear from him again. I hesitantly agreed, on the basis that we would have some further chats to plan our meet up, and the last chat would be a video chat, so that we could both see that the other person was who they said they were. With the agreement made he said that he had to go. I should meet him online next Tuesday at 9.00pm. With that he was gone. No discussion, he had given me my orders. I relaxed in my chair, realising that I had been sitting upright and tense. I consoled myself with the thought that I could still withdraw from the process at any time. We were just two people who had chatted online. He did not know my contact details or where I lived. If I got cold feet I could stay away from the chat room and return to my daytime life. However, the fact that my knickers were soaked and I could not resist rubbing myself to orgasm with an image of Sir in my mind told me that my body did not want me to withdraw from the process anytime soon.

We chatted a few more times online. I asked general questions about his domination and my forthcoming submission. How he had realised that he liked being a Dom, and how I realised that contrary to my day to day life, I wanted to be a sub. He had stressed that I had to be completely submissive, I must do anything that he required or it would not be a true experience. That troubled me a bit. If he could do anything, he could do serious harm to me. I raised my fears with him. His response was that I should only do this if I trusted him completely. He was not trying to pressurise me in to doing this. He had dominated other women before, and there would be other women in the future. I almost felt rejected. I wanted to feel special, wanted, but here I was being told that I was just one in a line of women under his spell. His other argument was that he wanted more than one session with me. I was a BDSM virgin, and he wanted to educate me and develop my experiences. This would not be possible if I was seriously harmed the first time. He also mentioned that there would be a safe word for me to use if it became too much at any time.

This discussion ended one of our chats and I said I would consider his statements carefully before our next chat. I thought a lot about it over the next week. The two sides of my brain arguing back and forth. The sensible side saying that I didn't need the pain or the danger. I could get sex as often as I wanted and it fit in with my lifestyle. I could have the ultimate zipless fuck that did not mess up my life. Why change a winning combination?

The other side of my brain sneered at the sensible arguments. Why had I kept going back to the BDSM chat room? Why did I get so turned on by the chats and role play? Why did I have such incredible orgasms from my sessions in the BDSM room? Why had I not bothered seeking out a man in a bar for vanilla sex for the last 6 weeks? Ultimately what swayed my decision was the naughty side of my brain telling me that in the future whilst I may regret some of my sexual escapades, it is far better to regret things that I have done rather than regret things I have not done. I didn't really have an argument against that.

My decision was all but made. Our next chat was going to be a video chat, and unless anything sinister happened during that chat, I was going to go ahead. I realised my nipples were hard and my pussy was wet. I slid a hand inside my knickers and masturbated myself to orgasm, my mind conjuring up images of what might be to come.

The video chat went well, no unpleasant surprises. We had chatted about who we were, what we looked like, what accents we had. The chat confirmed that Sir was as he had described himself. This reassured me and reduced my heart rate from the rapid rate I experienced as the call was connecting. Sir also confirmed that there were no surprises at the way I looked. He told me about the arrangements he would make for our session. It would be on neutral ground in an anonymous hotel in an anonymous town. We arranged it for a Friday afternoon. Sir had told me that after the session there would be some marks on my body and it might also be a little uncomfortable for me when I sat for 24 hours. I did not want anybody at work wondering why I was wincing when I sat down, so it made sense for me to take a Friday off for our meeting and have the weekend to recover.

He told me that he would text to confirm the hotel and location. I would arrive at the hotel first and enter the room. He would pick up a key from reception so that he could enter the room at precisely 4.00pm. I was to be sat on a chair in the middle of the room, dressed in my work clothes with a blindfold on. I would receive the rest of my instructions when he entered the room.

I put the blindfold on with two minutes to go to 4.00pm. As my vision was removed, my other senses were heightened. I could hear the drone of traffic on the dual carriageway outside. I could faintly here the intermittent noise of lifts moving up and down the building, but I could not hear anybody in the corridor outside the room. How long would I stay with my blindfold on? I obviously could not see my watch or the clock, and being blindfolded made time seem very elastic. I didn't want to take the blindfold off to look at the time, because Sir might arrive at that precise moment, and my disobedience would not be a good start. I desperately wanted to make a good first impression, I wanted the session to go well and confirm to me that this was what I had been searching for.

My body was in a state of considerable arousal. I could feel the dampness in my knickers. I squirmed around on the chair, trying to get a bit more comfortable. It was then that I heard the sound of the card key in the bedroom door lock. "Oh shit, I hope this is not room service" went flashing through my mind. There was no "Room service" greeting from the person, just the faint noise of footsteps coming in to the room, and the slam of the bedroom door behind.

"Well done slut. You have carried out my initial instructions as required. Let us hope that you continue to perform to an acceptable standard." The voice was cold and emotionless, but it did nothing to dampen my excitement, if anything it made my knickers even wetter. I could tell that Sir had walked past me and placed something on the bed. Was it a case or a briefcase? I could not tell.

I imagined him standing up straight before addressing me.

"Here are my instructions for the evening. You will call me Sir at all times when you are answering my questions. If you wish to ask me a question, you will raise your hand and wait for me to give you permission to speak to me. Any instructions from me shall be acted on immediately. Any delay in implementation will be punished. Any exclamations or speaking as a result of my actions will be taken as disobedience and will lead to further punishment. We have discussed your limits and these will be respected, but you must expect your punishments to hurt. This process does not work without pain, so you must be prepared to endure my treatment of you. If you accept your punishment and behave as required you will be rewarded at the end of the session. If you cannot accept your punishment, the safe word for you to use is Hamburg. If you use the safe word at any time, I will stop immediately. The session will be over. I will leave and you will never see or hear from me again. Do you have any questions slut?"

"No Sir. I understand everything you have said today and in our previous conversations. Thank you Sir for this opportunity."

My body was melting inside, a strong cocktail of arousal coursing through my veins carrying blood to all of my vital organs and sexual organs. I was on a high of knowing that it was happening, that I would finally be scratching THE ITCH. I was hoping that the pain would enhance the experience, but I didn't know for certain that it would. It might be too much and I might have to resort to the ignominy of using the safe word and having my fantasy come crashing to the ground.

"Stand up."

The instruction was terse and cut through all of my worrying. I stood up from the chair, conscious that any tardiness would be punished.

"Go and stand behind the chair"

I put my hand behind me to feel the top of the chair and then shuffled around to stand behind the chair. I was wearing a work outfit, black jacket and skirt with a white blouse underneath. Black high heel shoes but because it was summer time, no tights or stockings.

"Take off your jacket, skirt and blouse"

I slid the jacket down my shoulder and arms and let it drop on the floor. I nervously started to undo the buttons on my blouse, down the front and at the cuffs of my sleeve. Eventually all of the buttons were undone and the blouse followed my jacket. I unhooked the fastening for my skirt slid the zip down and then wriggled the skirt down over my bum to the floor. I hoped it was in a sexy way as I bent over, pushing my shapely bum out.

I stood up in my light blue underwear and black shoes, shivering slightly from the eroticism in the air. I sensed movement and realised that Sir was gathering up my clothes and moving them away from the chair.

"Bend over. The first step is to warm you up a bit"

I bent over and heard a swishing in the air near to me and then felt the first impact on my bum, rapidly followed by multiple strikes. I realised that Sir was using a flogger on me with a forehand strike followed by a backhand strike as the flogger struck my left and right bum cheeks alternately in a figure of 8. The strikes were not too hard but the repeated strikes were warming up my skin through my knickers, giving me a warm glow. After about 30 seconds the strikes moved up my body to warm up my back.

The strikes from the flogger stopped.

"Stand up"

I stood up, slightly disappointed that the flogging had stopped, as I was enjoying the glow spreading across my skin. I did wonder what was going to come next. I felt movement again as Sir moved to the side of me.

Thwack. I heard the sound and felt the pain across my nipples at the same time. My bra covered breasts had both been struck simultaneously with a long implement which I assumed was a paddle. My breasts bounced in response as the sensations spread through my body. My pussy lubricated more as the instantaneous pain turned to pleasure as the endorphins spread through my body. I had managed to stifle my urge to shout out. Sir would not be pleased with verbal reactions to pain.