by Cheri Grade
The correct approach would have been to throw the paper in the bin and forget about it. The situation was too strange and I could easily be getting into something which I wouldn’t be able to handle. On the other hand, here was a rich, confident man who could have any woman he wanted and he had chosen me. Admittedly, I wasn’t sure what I had been chosen for but it must surely be more exciting than anything I had planned otherwise.
I couldn’t concentrate all afternoon at work thinking about what I was going to do. I ran all the objections through my mind. Would Jack be angry if I didn’t go? He was the boss after all. What if I didn’t like it? What if I did it wrong? My subconscious screamed problems at me. I didn’t listen to any of them. By the time I left the office at five, I had resolved to become a new person – one who was willing to try new things and would prove herself worthy of Jack Beaumont.
Chapter 3: Stage One
As soon as I got home, I started thinking about how I could look my best for Jack. I had a bath and shaved my legs before thinking about clothes. As I looked through my wardrobe, I cursed myself for my unadventurous fashion sense and resolved to do something about it as soon as I could.
After some thought, I put on a red, lacy bra and knicker set. For me, it was quite revealing although I anticipated that Jack would find it relatively tame. I looked at myself in the mirror disapprovingly, wishing that my breasts were larger or my hair was longer, but there was nothing I could do about that.
I only had one dress which I thought would be suitable. It was a simple, short black dress with some lace detail around the hem. It was relatively low cut and I was happy to see that my bra had given me some noticeable cleavage which I was unaccustomed to. I had only worn the dress once before on a night out with the girls and had felt uncomfortable with the attention it attracted. That night, I had paired it with tights, but I had decided the new Lily would go bare-legged.
I tried on every pair of shoes I owned to finish the outfit before finally settling on a cute pair of heels with a pretty strap around my ankle.
My make-up took nearly as long. I didn’t usually wear much, but I wanted to impress Jack and so I gave myself bright red lips and used mascara to emphasise my eyes which were the one part of my body I was proud of.
It had taken a couple of hours, but now when I looked in the mirror, I saw a different person to who I had been this morning. I just hoped it was enough for Jack. He was clearly more experienced than me and had his own plans for tonight which I was slightly apprehensive about, but more than anything, I felt excited that a man like that would want me.
With a girlish giggle, I imagined that by the end of the night, Jack would be removing these clothes that I had chosen so carefully. I thought about him caressing my sensitive areas whilst I gradually approached ecstasy.
I spent the rest of my time looking at bondage videos on the internet, trying to imagine myself in the position of the beautiful models as they were tied up, spanked and finally taken by the men. I felt wetness between my legs as my excitement grew. I was desperate to orgasm as I felt myself getting closer, but I resisted the temptation, wanting to save myself for later.
It was soon time to set off. I had a short bus ride to town. Looking around me, I was surrounded by people on the way to nights out. My confidence wavered for the first time as I saw that, despite my best efforts, there were many girls who were prettier or better dressed than me. However, I had come this far and there was no way I was going back home without having seen what Jack had planned for me.
After getting off the bus, the cold made the walk to Jack’s flat unpleasant. I had decided against wearing a coat as I wanted Jack’s first impression to be me in the dress. I was grateful when I finally reached Jack’s building, shivering and with numb legs. I had only just made it in time so I half-ran to the lift and then from the lift to Jack’s door.
My watch said it was two minutes to nine. I had made it and now was my last moment to back out. I felt overwhelmed by cold and by excitement as I hesitated for a moment before raising my hand as if in slow motion and knocking on the door.
After making me wait about thirty seconds that felt much longer, Jack answered the door. He was still wearing the jeans and t-shirt from earlier but had added his suit jacket. I don’t think the look would have worked as well on anyone else but I thought Jack looked amazing. He looked me slowly up and down as I stood there on the doorstep waiting to be invited in and I was rewarded with a slight smile.
“Come in,” said Jack leading me to the sofa in the middle of the flat. “Glad you could make it. Before we start, there are a few points to discuss. Let me know if there is anything here that causes a problem and I will decide whether we can still proceed.” He took a piece of paper out of his pocket and handed it to me as we sat down.
As Jack looked at me intently, I read the neatly typed text on the paper. It was headed “Stage One Agreement”. Underneath the heading, there was a list of things I would agree to and a request for my signature.
As I scanned the list, I was relieved to find that there was nothing particularly objectionable there. Most of the items related to obeying Jack’s orders, for example he could tell me what to wear, when to speak and any other commands would have to be followed to the best of my ability.
The slightly more worrying items related to him being able to tie me up or spank me if I was “naughty”. I was reluctant to agree to this, thinking how humiliating it would be to be put over my boss’s knee and spanked like a child. However, the document specified that he would not leave a mark and therefore the actual pain would not be unbearable. In any case, surely if I followed all Jack’s commands satisfactorily, he would have no excuse to punish me.
All thoughts of raising an objection vanished as I read the last item: “I agree that Jack can touch me anywhere on my body and his cock can be placed in my mouth or pussy at any time he wishes.”
I looked up into Jack’s eyes and imagined him having sex with me, knowing that this was how the night was going to end. I ached for that moment and was prepared to do anything for it. Not trusting myself to speak, I gave a small nod. Jack rewarded me with another slight smile and handed me a pen for my signature.
“Thank you,” said Jack. “I look forward to training you and once you are truly mine, I will make sure you get what you want too.”
My hand trembled slightly as I signed the bottom of the agreement and tentatively handed it back to Jack. There was still part of me that harboured doubts, but I was being led by my libido. Even without the agreement, I don’t think there was anything I could do to resist Jack’s allure.
Chapter 4: Training
“Good,” said Jack, scanning down the paper before folding it up and putting it into his pocket. “I thought you were the type of girl who would want to be taken charge of. Don’t worry, that is exactly what I am going to do. If you please me, I will reward you and if you disappoint me, you will be punished. Do you understand?”
“Yes,” I said.
“Yes, sir,” he corrected me.
“Yes sir,” I repeated, worried that I had already made a mistake.
“That is much better, but you will only learn from your mistakes if you understand the consequences. Now, stand up and stay still.”
I stood as requested. Jack remained sitting, his eyes focussed on my body in a way that made me self-conscious. I looked back, trying to fight the trembling caused by my worry of what would come next. Jack was stretching the moment out as I mentally thought of all the items that were on the list and wondered what he was going to do to me.
Suddenly Jack rose to stand in front of me. “Drop the dress,” he said, abruptly.
I hesitated for a second, suddenly shy of this man seeing me in my underwear. However, I knew that I had to comply. Quickly, I slid the straps off my shoulders and let the dress fall to the floor, wiggling slightly to get it over my hips.
Jack had been motionless through the entire movement and continued to move only his eye
s up and down my exposed body. I was glad of the time I had spent choosing my bra and knickers as I knew the red looked good on me. For a second I wished I had picked red shoes to match as the black heels now looked out of place. However, it was too late to do anything about it now.
In one motion, Jack was standing in front of me. He was so close, I almost stepped back. I could smell his aftershave and see every detail of his face as he leant towards me and gripped my chin as if to kiss me. However, he held me back as I tried to lean in.
“Not yet,” he said. “We are only just getting started.” His hand traced a line under my chin, down my neck and on to my right breast. Feeling my nipple through the lace, he suddenly gripped it and pulled. I gasped in shock and excitement.
“Now follow me,” he said turning away from me and leading me to one of the doors in the wall. He opened it and led me inside.
The room had no windows and was lit by a single bulb hanging from the roof. The walls were plain white and the floor wooden however, the room was full of bondage equipment. There were racks and frames which were clearly for people to be tied to as well as holders for whips and other spanking implements on the walls. There was a large proportion of the equipment which I couldn’t even guess the use.
My nerve almost failed me as I heard Jack shut the door behind me with an ominous thud. “Impressive isn’t it?”
“It is,” I said, stunned. Then, catching Jack looking at me, I added “Sir”.
“Too late. Remove the bra.”
Frustrated with myself, I reached behind myself and unhooked the bra letting it drop to the floor. My breasts were at least pert although I was worried about their small size. As before, Jack just stood in front of me, the only movement was his eyes going up and down my body. “At least you are obedient, even if a little forgetful,” he said.
Jack gestured to “Before we play with any of this, you will have to learn some positions. Kneel down.”
I knelt as quickly as I could. I knew that one more infraction would lead to me losing my knickers and after that, I was sure that further punishments would involve the equipment in this room and I was not looking forward to experiencing that.
Jack roughly grabbed my hands from where they sat on my knees and pushed them flat to the floor. “Now look up and open your mouth wide.”
Again, I complied as best as I could.
“That is the position I want you to take on the command, ‘Kneel’. Do you understand?”
“Yes, sir.” I saw the first hint of a smile cross Jack’s lips before he caught himself and regained his dominant persona.
“You aren’t as dumb as you look,” he said. “Now lie face down on the ground with your arms by your sides.”
As quickly as I could, I moved to take the position. The hard wood felt uncomfortable on my nose, but I didn’t dare to turn my head to the side.
“The command for this position is ‘Lie’. Do you understand?”
“Yes, sir.”
He continued in this vein, teaching me “Spread” where I sat with my legs as far apart as possible, “Dog” where I got on all fours and the worst one, “Jump,” where I had to do star-jumps until Jack told me to stop. The star-jumps were particularly tricky as I was still wearing my heels and I was sure Jack wouldn’t let me take them off.
After teaching me these five positions, he started barking the commands for each position in a random order. I complied with each command. I think he was waiting for me to make a mistake, either to be too slow or to not replicate the position perfectly. I lost count of the number of commands that I had successfully complied with and felt I was doing well. However, I couldn’t keep it up forever. Jack was leaning comfortably against one of the bondage frames whereas the constant changes of position eventually started to tire me out.
“Lie,” said Jack. I was grateful for the momentary rest as I lay on the floor, the only sound was my laboured breathing. After too brief an interval, Jack said “Jump”. I pushed myself awkwardly up off the floor and started to do star-jumps. My legs felt heavier and heavier and I was slowing down. My throat burned with every gasped breath. Jack was clearly aware of my mounting discomfort and was delaying issuing his next instruction.
Just when I thought that I would have to give my knickers up after all, I heard Jack say “Kneel”. Gratefully, I dropped to my knees, my head dropping as I gasped for air.
“You forgot to put your head up,” said Jack immediately.
I knew instantly that he was right and I hadn’t got into the position correctly. Too late, I raised my head and opened my mouth as I should have done earlier. I consoled myself with the thought that the physical exertion was now over. How long had it been since I had come into Jack’s flat? Surely, I had done enough to earn the sex I craved?
“Stand and remove your knickers,” Jack said, breaking my concentration.
Thus, I stood there, in the centre of a room filled with bondage equipment, naked except for my heels along with my fully clothed boss. I felt like I was blushing at the indignity of the situation, but consoled myself with the fact that, given the exertion earlier, my face was probably already as red as it was going to get.
Jack knew how to keep me guessing as he again waited, just looking at me. Then he walked slowly in a circle around me, presumably looking at me from every angle. I stood there, trying not to react as I wondered what his next move would be.
Jack circled me a number of times, like a predator who was wondering how to take down his prey. He was standing behind me when he made his move and put a hand on my naked breast, squeezing it tightly until I almost cried out in shock and pain. He cupped the other breast and started to massage both more gently. My nipples had been erect just from the thought of him looking at me and I was getting increasingly excited as he fondled them.
I could feel his body against my back as he stood behind me and his warm breath caressed my neck. I closed my eyes, trying to concentrate on nothing except the feeling of Jack touching my body. His hands were now falling to my hips, moving behind me to squeeze my bottom. I ached for him to move his hands around to the front of me, to feel the wetness that I had been saving up for him all day. As if reading my thoughts, his hands started to move around my hips to just below my belly button before making their way down, lightly brushing my pubic hair as they moved to my thighs.
He had to move even closer to me to get into this position and I was sure I could feel his erect penis through his jeans. It was proof that he wanted me as much as I wanted him. However, he continued to tease me, his hands desperately close to my pussy but never quite touching it. He moved his hands between my breasts, bum and thighs, generating sensual excitement at every touch.
He must have known how excited I was from the way my breathing deepened and the dampness of my pubic hair as he kept me on the edge of ecstasy as I stood there pliantly submitting to his every touch.
Finally, I felt his head lean in towards my neck as his fingers worked his way up my thighs. I thought that this was the moment, he was going to kiss me and finally I would be his. Instead he whispered “That’s all for today,” and abruptly took his hands off my body.
“No,” I objected, unsure what else to say. I felt so horny, it overrode my better judgement and I grabbed behind me, feeling for his penis as I turned around. My hand brushed the front of his jeans as I found what I was looking for and even if I hadn’t, I could see his excitement for myself.
I put on my sultriest voice. “Enough of this, I want you now.”
My sudden confidence drained as I saw the anger in Jack’s face. “I said I want you to leave.”
“But…” was all I could say before he cut me off.
“Take your clothes and go. If you cannot follow the rules, I want no more to do with you.”
Meekly, I turned away. I was conscious of my nakedness as I picked up my knickers from the floor before opening the door and walking back into the main room. Jack didn’t follow me as I walked to where my discarded cl
othes were lying on the floor and hastily slipped them on.
Jack still hadn’t left the bondage room and I didn’t want to go back there and face his anger again. As I left the flat, I was reprimanding myself. How could I have been so stupid? After all I had been through tonight, how could I have thought that acting so brazenly would be what Jack wanted? It was clearly part of the game he was playing to turn me on and then to deny me. I was sure that other nights would have ended differently. However, there wouldn’t be any more nights. I had messed everything up. It was a long and cold walk back to catch the bus back home.
Chapter 5: Return to Normality
The next day, I had to go to work as if nothing had happened. Katie looked at me in a funny way as I walked in and I wondered if she suspected or knew what had happened. She had been the one to tell Jack about our conversation and had unwittingly or not set this whole process in motion. I tried not to give anything away and to exchange pleasantries as if nothing had happened.
Susan and Beverly were chatting away, clearly oblivious to any real or imagined tension between me and Katie. I just got on with my work rather than joining in.
Jack was already in his office and I could see him every time I looked up from my computer. Unusually, he was never looking back at me. At least I didn’t have to work directly for him. It would be mortifying to have to speak to him the day after he both fondled my naked body and threw me out of his flat. I thought about trying to speak to him, to apologise or to beg for one more chance. However, he still intimidated me, the previous night certainly hadn’t changed that.
Once I had finished the letter I was typing, I walked over to the stationary cupboard. As I picked up an envelope as I waited for my printing, I noticed a pile of familiar looking large brown envelopes. Jack must have used one of them the day before to give me my instructions.
I had already started walking away when I had an idea and indecisively stopped for a moment in the middle of the office before turning back around. Hunched over the printer so nobody could see what I was doing, I took a pen and a sheet of plain paper from the cupboard and wrote “I’m sorry” in big letters on the paper before putting it in one of the brown envelopes. I might not be able to face Jack, but at least I could give him a message.