Man Offers A Caning Service Ch 04

If you have read Chapter 3 I apologize but I have yet to have my, much awaited, session with Carly but will write about it as soon as I do. The story below is totally unrelated to Carly but the name of the main character is very similar.

Unusually Carla and I did not meet before the evening of our session together. She had contacted me following a recommendation from one of my clients but we lived too far apart to make a pre-meeting easy. We had exchanged emails and she had been very clear what she required. She wanted to be embarrassed, humiliated and caned severely. This was to be punishment for cheating on her girlfriend while her girlfriend had been away. Carla was desperate to be fully forgiven for being unfaithful. She said that she could not have sex with her girlfriend (Annie) until she felt suitably punished. Uncharacteristically, I had suggested that Annie was present for the punishment and I added I might invite someone else to maximize her embarrassment and humiliation.

Carla had told me that she had not had sex with a man for a very long time but would consider allowing me to fuck her. I had decided before she arrived that I would not be taking her up on her rather strange offer. What she was unaware of was that Annie and I had also exchanged emails with the aim of making Carla's punishment everything she could hope for. Annie's emails not only confirmed everything that Carla's had said about her wish to be very severely punished but also made some suggestions that I was delighted to take on board.

When she arrived I was stunned by her appearance. She was dressed like a professional woman of standing. About five and a half feet tall with a presence that made her appear taller. I know her age but that is not something I will divulge even though she looked much younger. Her makeup was immaculate and enhanced her almost regal looks. I suspected that she had been a model in the past and her poise gave her the look of a classy lady. Annie was much shorter and slighter in build with a cracking smile that lit up her pretty face.

Having not met before we did have a brief discussion to ensure there was no misunderstanding. I didn't mention Bill who was not in the room that I had shown them into. Given Carla's confirmed wish to be humiliated and embarrassed I was still certain that he would add so much. His involvement was one of Annie's suggestions and it opened up plenty of opportunity for embarrassment and particularly humiliation. Having agreed things I now had to take complete control of the situation. I directed Annie to a large comfortable chair and reminded her that she was not to say or do anything unless I prompted her to. In as dominant a voice as I could muster I told Carla to stand in the middle of the room and strip to her underwear. She did this with elegance and no apparent embarrassment. I knew I had a real challenge to strip this lady of her dignity. Her stockings and suspender belt complemented her classy brief panties and matching bra.

It was time to change the atmosphere and Bill was my trump card. When he walked into the room Carla appeared crestfallen and made to cover her near naked body as much as she could.

"Bill is here to watch you stripped naked, spanked, flogged and caned. He will start by checking whether the anticipation of your caning has aroused you. Take your bra and panties off ....... no wait he can check on your panties at the same time as he checks your pussy. "

If looks could kill I would not be writing this story. She looked as if she was going to stop him as he approached her but she kept still as he slipped his hand down her stomach and into her panties. It was inside them for only a couple of seconds before he held his fingers up and rubbed two of his fingers and a thumb together to show the slippery lubrication.

"Thank you Bill I will take that as a yes. Carla you can leave the stocking on but the rest can go."

She did just glance at Annie quickly before with her second sign of reluctance removed first her bra and then her panties. As she straightened up there was still defiance in her eyes but some of her confidence had seemed to ebb away. Her body was firm and toned with smallish firm boobs topped off by good-sized conical nipples. Due to the size of her breasts and the fact that her nipples were erect these looked large. I was delighted at her nipples in particular, as I had planned to start the punishment by whipping these soundly. I was very concerned that I would not be able to be severe enough especially when caning Carla. I have reached a point in a number of sessions where a client wants more than I am prepared to deliver in terms of pain. I had therefore planned to punish varies areas of her body using more than one technique on some of them. In this way I hoped that the build up of pain across her body would satisfy her demand for severity.

"Annie be kind enough to stand behind Carla and hold her arms tightly behind her back. I want her chest pushed out so that I can flog her boobs. There that is perfect."

I had chosen a heavier flogger than I would usually use on boobs and in particular nipples. Standing well back I started to spin the flogger so that its arc fell just short of her boobs and the targeted nipples. When I moved it a few inches closer the very end of the flogger whipped the very end of her nipple. Her shriek was music to my ears and the nipple was soon being struck three or four times every second with increasing force as it struck a wider area. For the first time since she had arrived I had Carla's undivided attention. I expected her to shy away from the flogger but she did exactly the opposite. Her look was now one of "is that the best you can do?"

The nipple I had been striking was soon changing from a pink color (her areola were a very pale pink) to red while growing much bigger than its untouched twin. I repeated the treatment on the other nipple but was unable to tease her before first making contact as she moved forward so that the nipple was immediately in range. When they were both the same red in color and clearly very tender I stood back.

"Bill be good enough to offer Carla's nipples a little comforting."

Carla's face looked ready to explode but for some reason she held still as holding one of her boobs with both hands he took its nipple into his mouth with extreme tenderness. He licked and sucked it for a few seconds before offering the same comfort to the other nipple. Carla looked to be about to say something when I cut her off.

"Would you like Bill to carry on comforting you for a little longer Carla?"

"No, no you bastard no."

I know that it is important to obey the word no. On this occasion even said three times it still screamed, "Yes please that is wonderful." More to tease than to obey I told Bill to stop what he was doing which didn't go down well with Carla. I suspected her nipples were probably as large as they were likely to ever get and quickly applied nipple rings to both in an attempt to keep them that way. Annie held her captive tight while I did this.

What I did next was a calculated risk. I told Bill to remove his clothes below the waist and Carla to go over to him and thank him for his attention to her nipples. I told her to use her hands and nothing else. The look of disgust on her face told me I might have gone too far. It was Annie who saved the day.

"If you want my forgiveness you must do everything you are told. You must also take all the physical punishment offered. Now get on your knees and do exactly what you have been told to."

I now knew that I, no we, could deliver the embarrassment and humiliation Carla so craved. Whether I could deliver enough pain was a different issue. I told Carla that I would be asking Bill to rate how good her hands were when she was told to stop. For someone who claimed to detest penises Carla appeared to do a very reasonable job. Bill's prick was soon looking like it could explode at any time. I didn't want to risk that so told Carla to return to the middle of the room and kneel down with her head in her hands her bum in the air and her legs spread wide. By now her immaculate stocking were beginning to look rather sad so reluctantly I told her to remove them.

In this position she was going to be introduced to the cane for the first time that day. The area of very dark skin that surrounded her very neat anus was nearly three inches across giving the most wonderful target for the cane. I wasn't ready to commence the main caning but had found that the cane applied to the anus could be very painful. I stood over her facing her feet giving me a great angle to apply the cane and appreciate the view. Even as I gently tapped it with the end of the cane I got the desired response. Her whole body tried to remove itself from where the cane struck but a firm rebuke from me soon had her back in receptive mode. I made it simple if I had to wait before I struck the contact would not count. It took a couple of tries before she got the message and when I struck harder she cursed me. She even seemed to try and move so that the cane struck her pussy but I avoided it.

I let her collapse into a lying position after about a dozen stinging blows. Bill was again recruited to be the comforter. He had to spread her cheeks with both hands to enable him to find the most sensitive area that the cane had found. Now her protests seemed very real. It was not the pain but the humiliation particularly when I told her to spread her cheeks with her own hands. Quite rightly it was not Bill who she vented her anger at it was me. I was delighted I was at last getting through to her and breaking down the last remnants of her resistance. When I suggested that Bill returned to his seat it was Annie who told Carla to go and thank him. She said this time she should use her mouth as Annie wanted Carla to think of her crime in silence. When there was no protest I knew Carla was getting close to being tamed. It was no longer the confident professional woman who wrapped her mouth round Bill's prick.

Bill knew to indicate to me before there was any danger of him emptying himself into the willing mouth. It was now time for the caning to really start. Now I wanted Carla to publically admit that she wanted to receive the cane. A submissive and docile Carla made the request. I asked her how many she should receive. I had hoped it would not be too many and was rather shocked when she said 24. I usually give six or a dozen but this was no usual caning. I said I would deliver a dozen and review the state of her cheeks then.

The position I had always planned was one that I hoped Annie would enjoy. I asked her to form a back as she knelt down so that Carla could mount her as if mounting a horse. Carla then wrapped her leg around the horse's waist presenting the perfect taut checks to the cane. The first strike was harder than I had ever delivered a first strike. I wanted to ensure that Carla got all she wanted and more and preferably without me delivering two dozen. Much to my amazement Carla made no noise until I had struck three times. She had been holding her breath and this exploded out of her after the third. I wanted to add a twist to the caning and recruited Bill yet again. He traced each of the nasty looking red lines across her cheeks until he eased a single finger into her relaxed sphincter. The expelling of breath was almost as dramatic as it had been from the caning. I told Carla to thank Bill verbally this time. She did without argument. Three more groups of three were delivered with a similar penetration of her anus. No protests were now being offered but each strike with the cane was registered with a scream of pure pain. For the third of these groups I required her to thank me and request the next one. She needed no reminding.

I had only delivered twelve blows but was reaching a point I did not wish to go past. I told Bill that he could explore a little further if he wished. With a huge grin he slipped his thumb into her anus and brought the fingers of the same hand round to find her clit. I had deliberately ensured that any contact with her clit had been minimal. She ensured that he had full access to her pussy and clit and started to ride his fingers and thumb. Even though her body must have been hurting, or maybe because it was hurting, she was clearly highly aroused and possibly close to orgasm.

At my request Bill withdrew his hand and returned to where he had been sitting. Carla complained as she stiffly dismounted. As they stood facing each other Annie held Carla's tear stained face in both hands and said,

"There is just one more thing you need to do and one more thing I need to do before I forgive you. You betrayed me with your body and your final punishment is the most painful thing I can ask you to do. Go over and thank Bill and keep thanking him until he fills your pussy."

I hadn't seen this coming but realized that it was probably the final humiliation that Carla needed to suffer. It was a very subservient Carla who with tears now flowing down her cheeks mounted the very erect Bill. Bill removed the nipple rings before Carla fucked him until they both exploded in orgasm. The view from behind her as she rode him with so much apparent enthusiasm was heightened by the raw stripes that were now turning from red to purple. She seemed to have converted the pain into raw sexual excitement.

I thought this was the final act of a session that I hoped had brought Carla everything she had wanted. But the person who had orchestrated more of this session than I had had one more surprise up her sleeve.

"I have been faithful to you since we first made love. It must have been humiliating for you to be forced to orgasm on a prick the very thing you despise so strongly. I however have missed a good fucking by a man for so long and to complete your punishment and my forgiveness I am going to enjoy a most needed fuck with the man that has made our reconciliation so complete."

I had hardly noticed how arousing the last hour had been for me but when I entered her pussy we were both extremely ready. She came before me but insisted that I fucked her until I emptied my overfull balls deep inside her welcoming pussy.

As they went to leave Annie insisted that Carla presented me with her panties and thanked me for punishing her

.

This done Annie announced that Carla was fully forgiven and the matter would not be raised again.

Carla contacted me the next day and said that she had loved the whole session. She said when they got home they had enjoyed a long session of 69ing as a way of washing all traces of us males out of their bodies. She had found the repugnant taste of my seed had still not prevented her matching Annie's first orgasm with her for weeks. Carla was delighted that Annie had completely forgiven her.