Married Guy New Experience Ch. 04

"Fuck the Wimp", "Hurt the Wimp", "What a fucking Wimp, very well named"

They started to clap to the beat of his fucking of my ass which encouraged Jim to fuck me even faster. The pain was going right through my body and I was now crying and whimpering, much to the amusement of all in the room, including the other Subs. Eventually I felt Jim tense up and I knew he was close to cumming. He slapped my ass hard as he finally came hard in me, I felt his cum spill into me.

When he was finished I went to move but was stopped. Jim came around to my mouth and placed his wet cock into my mouth. I knew what to do and started cleaning his cock, licking it dry. Once that was complete he slapped me on the head, almost like praising a dog for my behaviour. He was then handed something by Mark. I did not look up as I was slapped the previous time I looked. I then saw some flashes and it was obvious that Jim was taking pictures of me.

When he was finished the other Masters came over and looked at me closely, most of them looking at me from behind. I expected someone to do something to me but nothing more happened. Bitch came over to me signalling for me to get up. He handed me my yellow briefs which he indicated I should put back on. He then took me back to Jim and I sat down in my seat at his signal.

I looked around and noted that my fellow yellow briefed Subs were now looking very nervous as they must now be aware of what might happen. Before I could see any more Jim spoke.

"Wimp, get dressed we're leaving."

With that he got up, said goodbye to Tony and left the room. I hurried after him and I was wondering if I displeased him in some way. As I left the room I saw that Pleasure was being led to the platform and I was disappointed not to witness what might happen to him.

When we got outside, Jim walked to a waiting taxi. He got in the front with me in the back and we returned to my hotel. We immediately went to my suite and to my relief the same receptionist was not at his desk. On entering the suite Jim spoke for the first time since leaving the club.

"Get me bourbon"

I went to the mini bar and poured him his drink. He finished his drink while I stood before him. He then got up, handed me the empty glass.

"Ok Wimp, I'm off to bed, I suggest you do the same, I will now go think about your behaviour tonight, good night Wimp."

"Good night Sir," was all I could think of to say. I was afraid to say anything else for fear of displeasing him. I was wondering if he was not happy with how I had acted, had I disrespected him? Should I have said more? Should I have thanked him? Was he upset that I had been silent while he fucked me? My mind was trying to think of how I might have displeased him?

I then went to my room, trying to stay awake in case he came in. I set the alarm for 7.30am, only four hours away. However, the long day and night caught up with me and I fell asleep quickly.

The following morning I was awoken by a slap on the head. I looked at the bedside clock and saw that it was 6.00am. Opening my eyes I was confronted by an erect cock, barely two inches from my mouth. I opened my mouth and Jim placed his cock in there, then pushed it all the way in, almost gagging me. This woke me up more and I started sucking on it greedily.

Jim laughed. "Even when you half asleep you're a natural cock sucker, look at you, you can't get enough cock."

It wasn't long before he climaxed in my mouth. This time I swallowed every drop.

"Well done Wimp, you're getting better. Last night was only the beginning, now get showered and then we'll talk."

I got out of bed and went to the ensuite shower off my bedroom. I showered quickly and went back to my bedroom, drying myself as I walked. Jim was sitting on me bed.

"Lose the towel."

I dropped the towel, standing naked in front of him. He looked me up and down.

"I still find it hard to believe how small and insignificant you are, WIMP is definitely the right name for you, now tell me what did you think of last night"

"Sir, it was scary but I think I enjoyed it, can I speak openly?"

"Yes Wimp you are free to say whatever you want."

"Sir, for the most part I enjoyed it. I did not know what to expect and most of the night was very exciting. If I am being honest I did not expect you to fuck me like you did. I thought you might have built up to it, prepared me rather than rape me brutally."

Jim stared at me, "You think that was a brutal rape?"

"Yes Sir."

Jim laughed loudly. "Oh Wimp you have such a lot to learn. If I choose to go on with you, you will experience much more than that. I wanted to make sure that you could take hard sex, that you could perform in front of an audience, that you would not fight any instructions or actions."

"Did I satisfy you Sir."

"Yes Wimp you did well enough for your first attempt. What did you think of all the other Subs, did you notice anything?"

"Several things Sir, the different colour briefs indicating some kind of Sub rank, that they all had uncut cocks, that I was by far the smallest of all."

"Do you think you want to wear other colours, Wimp."

"Yes Sir."

"Do you realise what efforts are involved in reaching each colour?"

"I think so Sir."

"It normally takes four meetings at each level. Are you prepared for that level of commitment?"

"Yes Sir, I want to learn more from you."

"Bitch has been with Tony for two years now. Bitch is also a married man but is totally committed to Tony. When Tony calls Bitch comes running to wherever he is required. Bitch has a wife who knows nothing about his activities and he still has sex with her when Tony allows. I have been looking for such a Sub, can you be that Wimp?"

"Can I still talk openly Sir?"

He indicated that I could. "Sir, this is all still very new to me. I think I want more but how can I be sure. I enjoy the cock sucking, I think I enjoyed you fucking me even though my ass is still incredibly sore this morning, I am not sure I like the humiliation about my small cock even though I now totally know how small I am compared to other guys. I am still very worried about Olivia finding out, or my work colleagues. I am not sure what I would do if they found out. You tell me to trust you but how can I be 100% sure about you. Sorry Sir if that offends you."

"Wimp we have to be honest with each other, otherwise this will not work. I think you are a natural Sub, I think this is what you were born to be. You can trust that I will never do anything that I do not think deep down you do not want. I am prepared to invest time in you but only if I have your total commitment."

"Sir I think I want that, at least to try and be what you want me to be."

"Ok, I know you have meetings today so you need to get ready. I have put some new yellow briefs on your bed. Wear only yellow until I tell you otherwise, even when I am not with you."

"What will Olivia say about that Sir?"

"Wimp that is your problem, now go get dressed and get to work, I am going to sleep for a while, will contact you later."

I looked at the clock and saw that I only had thirty minutes to get to my first meeting of the day. I dressed quickly, left the hotel and got to my meeting with only a minute to spare. My ass was still sore and my mind was in overdrive. I somehow got through the meeting, even actually beginning to talk some sense and answer some of my clients questions and concerns. The meeting lasted over an hour and then we had coffee and chatted for a short while before I left for my next appointment.

I checked my phone but there were no messages from Jim. I wondered if he was still sleeping and when I would hear from him. Deep down I was hoping that maybe we would be having more fun tonight before I left for my next stop tomorrow. It still scared me how far I had come in the short time since I had first met Jim.

My next meeting went without incident and I was still waiting on any contact from Jim. I had already agreed before I had travelled to have lunch with this particular client and that went ahead as arranged. At 2.00pm I left the Client to head for my final meeting of the day. This was with a potential new client who had only contacted our Head office the week before. I checked the address from an email and hailed a cab. The offices were in a part of town with which I was not familiar. When I reached the address I noted that it appeared to be a house rather than an office block that I had been expecting.

I rang the door bell and a young woman answered the door. I told her who I was and she instructed me to follow her. She showed me into a large room which looked like a doctor's room with table and chairs, a large couch and an inspection table with stirrups. I sat down and waited to meet the potential client.

I heard the door open before me.

"Hi Wimp."

Stunned I turned around to see Tony, Jim's friend from last night standing there.

"Tony?" was all I could think to say.

He laughed, "So tell me how can you help me sort out my financial problems?"

"How did you know where I worked?"

"Jim arranged this, you have no idea how good he is at gathering information about people."

"Do you want to be a client of our firm?"

He laughed loudly. "I do actually need a new accounting firm but the rates would have to be very good. Do you think you could get me good rates, ha ha."

"What kind of business are you in?"

"I'm a Gynaecologist, isn't that funny, I spend all day looking at pussies but all I like is cock and man pussies."

I laughed at his comment. "So what financial problems do you have?"

"Actually, I don't have any, business is very good, stand up."

I stood up without question.

"Strip to your yellows."

Again I did as instructed and stood before him. He pushed a button on his phone.

"Betty, can you come in here please."

I started to gather my clothes.

"Leave them," he shouted as Betty entered the room. She did not appear to be in any way surprised at a guy standing there in briefs.

"Betty, can you get Wimp here ready for an examination while I go clean up."

Tony left the room leaving Betty in front of me looking me up and down.

"You heard the man, get on the table."

I went to the table and lay down on it.

"Legs in the stirrups."

I lifted my legs and she strapped them to the stirrups. She then went over to a desk and opened it to reveal some medical instruments. At that moment Tony came back into the room in a white coat.

"Wimp, I need to check whether you have any damage after last night. Betty, can you please remove the yellows."

Betty reached for a incisor blade and using them slit the briefs off me. She then removed them and threw them aside leaving me naked and bound to the table. Betty was the first woman to see me naked since before I had met Olivia.

"What do you think Betty?" Tony asked.

"I can see where he got his name. I have children bigger than him. Did you say he was married?"

"Yes, to Olivia."

"I must say that either Olivia doesn't like sex or she's getting it elsewhere. There is no way that cock could satisfy any woman." She slapped my cock as she said that. "Unusual for Jim to find a cut cock, he must think there's potential here."

"Ok let's start."

Betty lifted my cock up and began examining It closely. She took a tape and measured it.

"1.5 inches."

She then measured around the base and made another note. She followed that with a detailed examination of my balls and made more notes. She then went to the sink and got some shaving foam and a razor. She proceeded to shave my cock and balls area totally. She then pressed a button and the table lifted leaving my ass area totally exposed and my legs wide apart. She proceeded to shave the entire area from my balls to my ass and my ass area. I felt totally humiliated as she undertook the tasks in total silence. Tony sat at his desk watching.

When she finished shaving me she washed and dried me off but left me in the same position. She got some lubricant and put some into my ass, fingering me roughly as she did it. From my position it was difficult to see what she was doing. Next I felt something being placed against my ass hole and then being inserted into me. It felt very cold but slipped in easily. It did not appear to be thick and did not give me any pain.

She then turned to Tony.

"He's prepared."

"Thanks Betty, I'll take over from here, I'll call you if I need you."

With that Betty left the room and Tony left his desk and walked over to me. He came over alongside me and pinched my nipples hard.

"Wimp, see even Betty thinks you're tiny," he said reaching for what looked like a remote control. He pressed a button and immediately I felt the instrument in my ass began to vibrate, first slowly then much faster.

He looked down at me, "Does Wimp like that?"

"Yes Tony. It is nice."

"What did you call me?"

"Sorry, should I call you Sir as well?"

"Of course Wimp."

He pressed a different button and I felt as if the instrument in me was beginning to grow and expand. It expanded and expanded until I started to scream. Still he didn't stop pressing lightly on the button until a red light appeared on the remote.

He then put it down and went to the end of the table. He examined closely my penis and balls. Lifting them, slapping them, pinching them. I felt as if my insides were being stretched but I had become semi erect.

"Interesting," Tony said as he made more notes. He then pressed a button on the remote which lessened the thickness of the instrument in me. I felt as if the wind was being released from me but the pain remained.

"On a scale from 1 to 10 how bad is the pain?"

"Ten Sir"

He made a note, "Before long you will not regard that as ten."

He again used his phone and asked Betty to return, which she did immediately.

"Ten," he said to her.

"Wimp is correct name," she laughed.

"Can you clean him up."

Betty took the instrument out and cleaned me with some warm water, fingering me as she did that, smiling at me as she did so. As she cleaned me I became fully erect, she looked down, laughed, got the tape and measured me again.

"3.5 inches, should I let him wank for us?" as she made a note.

Tony looked over, "Wimp show us your cum."

"Please Sir don't make me do that in front of Betty."

They both laughed loudly, Betty slapping my erect cock.

"Do it."

Not wanting a bad report going back to Jim, I began to wank in front of both of them, each standing on one side of me looking down at my face. It wasn't long before I came but as usual not much came out of me. Betty took my fingers and rubbed them in my cum. She then put my fingers to my mouth which I willingly opened to taste my own cum. She then repeated the action but this time rubbing my fingers all around my face. She made more notes.

After she had finished she untied my legs.

"Sort yourself out Wimp."

It was difficult to stand up straight for a moment after my legs being held high and bound for so long. Tony threw new yellow briefs at me and I dressed quickly.

"Jim said for you to return to your hotel immediately, he is waiting."

I left both of them looking at their notes and returned to my hotel by taxi. My ass still felt bloated and stretched as I passed the reception. The receptionist from the previous day called me over saying he had a message for me.

"I was told to tell you that you should go up to your room, to shower and to lie face down on your bed and wait," he said to me smiling with a wide grin.

I was stunned and didn't know how to reply so I just said "Thanks," and left the reception area quickly. I could not believe that Jim had involved the receptionist. I went up to my suite in the lift, wondering what lay in store for me.

I could not see Jim or anyone when I entered the room. I did as instructed, showered and lay on the bed, waiting for what I didn't know.

I lay there for over 20 minutes, I knew that from the bedside clock. Then I heard some noise outside my bedroom and heard the door open.

"Nice," I heard someone say, "do not even think about turning around, put the pillow over your head."

I felt a hand touch my ass and spread my legs. Fingers then played with my ass, putting some cold lubricant into me. I heard a zip being lowered and felt the pressure on the bed as the person placed themselves next to me. They continued to finger me.

"Nice and Tight," as they reached under me and touched my balls.

He then got up on top of me and I felt a hard cock against my ass. He moved himself up and down my body teasing my ass as he did so. He then positioned himself and placed his cock at the entrance. He pushed himself in and I felt his hardness as he pushed what felt like a large cock into me. He eased in and out gently for a minute or two, building up the pace gradually until he was pounding into me with great force, pushing me down into the mattress. He also held the pillow down as he fucked me hard, and I was finding it difficult to breathe easily. The guy was very fit and kept up the fucking for what seemed a long time, varying the pace between very slow and furiously fast. Eventually the guy started panting hard and came hard in me. I could easily feel his hot cum spurting into me and they seemed to be a lot of it.

When he was finished I went to take the pillow off my head. He stopped me doing it.

"Wait until I'm gone, then count to 100. You can then get up, Jim said to wait by the phone."

With that I heard him getting dressed and leave the room. I counted to 100 and thankfully took the pillow from my head and breathed easily. I wondered who had just fucked me, I wondered if it was in fact Jim disguising his voice, had it been Tony? Could it have been the receptionist?

I lay on the bed, feeling the cum dripping from my ass. I placed my fingers there getting some cum and tasting it. It did not taste like Jim's cum.

A few minutes later the phone rang.

"Wimp, hope you had a good day, we are not going out tonight, order me steak and chips and get yourself whatever you want, we will eat in the suite at 8.30 pm." With that he hung up.

I looked at the clock, it was now 7.30. I picked up the phone and ordered his dinner and some lasagne for myself. I turned on the TV and watched some news programme. I have no idea what the news of the day was as my mind was still in turmoil. At 8pm Jim arrived and I was still naked on the bed.

"Get dressed Wimp, I don't need to see your small cock."

Quickly I dressed in a shirt and trousers, not forgetting my yellow briefs and went out to the living area. Jim was sitting on the large couch drinking a beer and watching a football match on the TV.

"How was your day Wimp?"

"Interesting Sir, my meetings went well, and then I met Tony, but you know that."

"How did that go?"

"Betty and he examined me fully Sir, they really stretched me out."

"And when you came back?"

"Sir, I did as you instructed and someone, I don't know who, fucked me."

"Wimp, you did well, did you like it when you came?"

"Yes Sir though it was humiliating in front of Betty."

"Did it taste different to the guy who fucked you after?"

I looked at him stunned, wondering how could he possibly know that. He laughed at my obvious shocked face. With that he reached for the remote control and switched channel. The picture changed and I could see myself on the screen sitting in front of Tony's desk before I met him.

"I watched it all Wimp, it makes a great video. He has some great camera angles. Let's watch it together."

We watched as the events in Tony's office took place, with some real close ups of my ass, my face, my small cock. It was even more humiliating to be watching what had happened than I felt when I was actually there.

Jim said every now and again.