21yo Works With Older Boss - Ch. 03

THURSDAY

The previous three nights Bob had shocked me. He had given me surprise after surprise so many firsts that I had never dreamt of. Every one of which I had loved and become highly aroused by. Could he surprise and arouse me again on Thursday evening?

By the time we finished working I was already so aroused I couldn't think straight. He asked me whether I wanted to stay or whether I wanted to go home. He said that he had two visitors but they would love me to join them. He knew I wanted to ask about the visitor but I knew I had to make my decision without asking. We both knew what my answer was going to be. I thought things might start very differently than the other nights but he handed me the blindfold and walked through the door as usual.

I was naked in seconds putting my clothes in a neat pile on the chair in the corner. It was a shame as I thought I had dressed very sexily but his guests would never know. He had not told me to undress and not given me instruction as to what position to take up. I decided to take up the most subservient position I could think of. I reached across his desk with my hands stretched as far apart as possible. My legs would not stretch quite as far apart as my arms but I did my best. The door opened as soon as I was settled. I guessed that all three of them had entered at the same time even though they were very quiet. I sensed rather than heard someone very close behind me and a single finger reached between my legs and past my clit before being dragged slowly and gently in a straight line over my clit and just past my anus. It was done just firmly enough for the arousal to be felt and spread. I had known I was wet with arousal but I was sure the other three now knew too.

"Her bottom is exquisitely sensitive. She had the most wonderful orgasm as I fucked it the other day, didn't you my dear?"

Having not been allowed to speak the previous three evenings I wondered if I should answer. Playing it safe I nodded my head.

"If I ask you a direct question you are free to answer."

"It was a wonderful orgasm, thank you."

"Did you have permission for your orgasm yesterday?"

"No Sir I am so sorry. I tried so hard to prevent it but I couldn't."

"It is interesting that you positioned yourself as you did to welcome my guests. Do you think you were subconsciously trying to tell me something? What do you think I should do with you for disobeying me?"

I was not going to fight. This conversation was only going to end with one conclusion. If it had only been Bob in the room with me I would have expected any punishment to be mental rather than physical but I was not so sure with his two guests.

"I deserve to be punished for having an orgasm without your permission. Would you please carry out my punishment so that you can forgive me?"

"Oh my guests are experts at punishing wayward girls. I think I will sit back and enjoy the show. I have asked them to make the punishment as appropriate to your disobedience as possible. As always you can stop proceedings instantly at any time. For the benefit of my guests I require you to ask them to punish you and tell them in your own words why you should be punished."

I was trying to get an image in my mind of his two guests. I didn't know their gender, their age or whether they were naked. There were so many other questions; did they know me, would I get to see them, would they only punish me or would I get to enjoy an orgasm even half as good as yesterdays. As always I would have no say, other than to stop things, in what went on but there was no way I was not going to find out.

"Would you please punish me in any way you think fit. I deserve to be punished because I had an orgasm when I had expressly told not to."

As I finished talking a hand started to explore the whole area from above my clit right round to past my anus. The hand was gentle as it swept in the one direction time and time again. As with the finger earlier it was spreading the considerable natural lubrication that was already there and that it was creating. If this was punishment bring it on. It was a female voice that addressed the other two in the room.

"What a pleasure to work with such a stunning body that is so easily excited. If the poor girl is aroused by being punished our biggest problem will be to prevent her getting over excited. We wouldn't want her to repeat the very thing she is being punished for, or at least not too quickly."

The last half a dozen words were music to my ears. Did this mean I would be allowed to climax? I had little time to consider the answer as someone, I have no idea which of the three, spread my cheeks wide and held them there. It could have only been her tongue that found the very center of my bottom. It was just lovely. I felt like crying the feeling was so sensual. I know the line between sensual and sexual is thin but this was just sensually divine. I would have happily enjoyed this for hours even though I would have never had an orgasm. It seemed clear to me that the owner of the tongue knew this very well and was happy about it. It had to be a female, as she knew my body as well as I did.

I knew there was at least one female in the room with me but I wondered whether there were two. Very slowly the tongue demanded more and more. It probed and demanded entry into the very tight orifice that gave up its secrets very slowly. I was trying to lift myself off the desk in an attempt to receive the tongue deeper into me but her hands kept me spread wide and pinned down. I was aware that there was some movement in the room and a male voice whispered into my ear.

"That is so hot I cannot wait to fuck a beautiful wet pussy."

Given everything I had experienced in this room I was a little surprised at how direct and quick this was. Very quickly the mouth was removed from by bottom and a cock was spreading the juices around my pussy. I pushed back trying to get what felt like a substantial dick into my willing pussy. The owner of the prick lent forward and again whispered in my ear.

"Your pussy will have to wait I am going to bury my very ready cock into my wife's very ready pussy. She cums amazingly strongly when she has a mouthful of female pussy or ass. Now turn over and offer her your pussy."

Who was I to argue? It was difficult to get into position without being able to see what I was doing but with a little help from someone's hands I was soon settled. The mouth that latched onto me was immediately in teasing mood. I wanted my clit to sucked and bitten but instead my clit was ignored but a tongue played from near my anus to just above my clit. The playing quickly changed when the owner of the tongue was clearly entered from behind. Her breathing changed and her tongue concentrated on the area just below my clit. Not surprisingly this connected directly to my bladder that was suddenly feeling very full. As the fucking that she was receiving got harder she was unable to keep the contact with my urethra and instead fell forward so that her stomach rested between my spread legs.

My clit craved contact and I wrapped my legs round her body that was being vigorously pumped from behind. Now the fucking that the female was receiving was rubbing her stomach against my pussy and my clit. I squeezed my legs around her trying to get enough contact to bring about my orgasm. My female lover announced that she was being fucked by both of us and that it was going to make her climax. Her husband laughed and told her to enjoy her orgasm. If the noises she was making were an indication of the strength of her orgasm then it was a spectacular one. Unfortunately it finished far too quickly to allow me to have one at the same time. As her weight was removed from me a mouth found my clit and sucked it hard. I cannot remember anyone going down on me when I was already very aroused and it felt beautiful. It didn't last long enough as a male voice not Bob's said,

"I haven't seen many clits that big and beautiful. I think we will have to do something about it if she is not going to cum far too quickly. Let me have the nipple pump and three rings."

The feeling of having my clit sucked hard changed and it didn't take me long to realize that it was not a mouth doing the sucking. My clit was being stretched like never before. Something then snapped against the base of my clit and squeezed. Pressure was built up again as my clit was painfully drawn further away from my body. The base of my clit was pitched again even harder than the last time.

"There that should keep it fully erect but the numbness will soon kick in and she will be ready to be punished without fear of orgasm. Give her one last licking before the sensitivity is lost."

Fuck - somebody knew my body better than me. The warm mouth felt wonderful as I felt a tongue moving along my clit. My clit felt as if it must have been an inch long as the tongue played along its full length. A minute ago this would have made me explode in orgasm but now my clit was becoming numb, as the owner of the tongue knew full well. The sensitivity was reducing quite quickly but the feel was still very erotic.

"Well my dear your clit will very soon be out of the game but your nipples look very ready to take the punishment that you deserve. But before we punish them lets see how they react to more gentle attention."

The couple were one on each side of me and in perfect unison they found a nipple each. They were firm but so arousing as they sucked each nipple first to full erection. This done they set about stimulating them staying in perfect unison. I had had my nipples sucked on many occasions but never by two people at the same time. It was clear that this was not new to them. They must have been using signals as every time one changed what they were doing the other did so at the same time. I expected my nipples to be slapped, pinched, squeezed viciously or attacked with a cane or something but this didn't happen.

I could do nothing other than to lie back and accept everything that was done to my nipples. After a few minutes I was in tears. I had no idea why I was crying. Was it helplessness, frustration, arousal or just sheer pleasure? I didn't know and I didn't care. There might have been things that could have been even better but I didn't want what was happening to stop. They only played with my nipples but it was my whole body that was buzzing. My clit was now completely numb or at least I could not feel it. That was until I felt a gentle tapping very close to it.

"Your clit may be numb right now but I am going to punish it for disobeying me yesterday."

I had nearly forgotten that Bob was still in the room. Now the increasingly hard striking of my clit had my full attention. My clit might have been numb but the pressure built around my clit and pussy was getting my attention. It was as Bob started to strike my clit that the stimulation of my nipples seemed to change. It became more demanding and for the first time it seemed possible it could be the trigger for me to orgasm. Hands were being used in addition to the mouths on my nipples.

"Today your challenge is to reach orgasm not to prevent yourself from having one. It will not be made easy, as your clit will remain bound very tightly. When it is finally released it will be very painful and I look forward to comforting you through that pain. Now I am going to leave you to our guests and watch your struggle."

Our guests took this as a challenge. Not one to frustrate me but one to help me in my struggle. I felt and heard the breath of both of them very close to my ears. A single finger played around my lips before accepting my invitation to be sucked into my mouth. I treated it, as I would have if it had been a small cock. It was erotic to suck on this finger. The next change was a wonderful shock. Both of my ears or more accurately my earlobes were gently sucked by warm mouths. Right at that moment my earlobes were as sensitive as my nipples. It felt like having four nipples expertly played with. Sensual morphed into sexual and even without my clit joining the party the possibility of orgasm entered my head. The build up was beautifully slow and I realized it was going to happen a full thirty seconds before the first spasm arrived. Lights of different colors exploded in my brain. Waves of pleasure washed through my whole body but the spasms were not violent allowing me to savor every last sensation including the finger fucking my mouth. The stimulation of my nipples and earlobes did not stop until I slumped, totally drained.

I was given no time to recover as my legs were opened further, bent further and pushed back towards my chest. The visitors then held them as Bob found my imprisoned clit. I could feel he was touching it but it was only a feeling of pressure as the clit itself was totally numb. He had obviously rolled the tight rings off my clit as I felt him apply something cold to the area and my clit did start to register the sensation. When the ice cube was removed his mouth replaced it. The cold had been soothing but the warmth was agony as my tortured clit exploded in pain. I screamed in pain as he entered my pussy. I barely felt the prick in my pussy as my clit was screaming as loudly as I was. From beside me a hand covered my mouth and a female whisper in my ear said.

"We are going to slap your tits and make them as painful as your clit but at least Bob will keep fucking you. I am going to take my hand away and give you the chance to say stop. If you don't your nipples will soon be very sensitive."

"Stop, stop don't you dare stop. Whatever I say slap them, slap them hard and fuck me silly."

I have never experienced pain that is indistinguishable or at least interchangeable with sexual arousal. Now I was asking for more, more pain and more arousal. The couple delivered as my nipples and areolas were struck with considerable force. The pain in my boobs and nipples was now joined as the numbness in my clit wore off. Nothing was touching my clit but the pain exploded as if my clit was being beaten. The fact that Bob was fucking seemed almost irrelevant but I was pleased that he was. The pain built but I did not expect this to trigger the violent orgasm that it did. Even the spasms that rocked my body were sharp and painful. The orgasm was short and ended as abruptly as it started.

Bob was still fucking me and it was really lovely to hear him announce his orgasm before increasing the depth and force of his thrusting. My eyes took time to adjust to the light when he took the blindfold off. Looking around I was disappointed that it was only Bob and I left in the room. He smiled down at me as he pulled out of me. He bent and took my clit in his mouth and sucked it gently. I did not need to wonder what his intention was for long as he stood up and with a big smile said "wonderful". He walked out of the door leaving me feeling very naked, very alone but very satisfied.

I could not imagine being aroused any time soon and even if I could what Bob could dream up for Friday night. Would he find one last way to surprise me?