Man Offers a Caning Service Ch. 01

It was five years after my wife died and I had not found dating easy over the last two years. I had enjoyed sex but it was all very vanilla. At nearly 50 years old I was still looking to enjoy a very full and varied sex life. My wife had always loved being spanked, strapped and caned and it had become an important part of my life. I watched some porn and came across an advert offering to spank or cane women. I decided that I would place adverts myself to offer initially caning only. I invented a past as a headmaster claiming great experience of caning both girls and grown women.

First client

I arranged to meet my first possible client to discuss what her requirements were. As agreed she brought a friend with her and much of the time was spent discussing safety issues. The lady was a little overweight and probably a few years older than me. She was very enthusiastic and we agreed on what would and what wouldn't be involved at our appointment on the next Saturday.

Even though we had discussed her requirements earlier in the week I was surprised at her no nonsense approach when we met. She immediately pulled her skirt up above her waist, pulled her substantial panties off over her feet and spreading her legs reaching for the far side of the desk. Her excitement was instantly obvious. Her bottom was large but not fat. Enjoying the view I approached her from directly behind and tapped her ankles with the cane to tell her to spread her legs wider. As she did so her generous pussy lips opened slightly and I was able to confirm they were moist. Having set the scene as agreed I got quickly on with the caning. The first six were firm and stinging but not too painful. Each one was received with a gasp but not much more. I gave the heat created by the first six to spread before delivering the next six. These were delivered with more force and were rewarded by protests and screams of pain. She did not use the safe word and I knew she had no intention to do so. I stood back and made her wait and built the anticipation. She was wriggling her bottom possibly to reduce the pain or possibly to speed me up.

Quite unnecessarily I tapped her ankles again before resuming my position. The view had changed as her pussy lips had plumped up and were now wet rather than moist. I delivered the next six with similar force to the previous six but with smaller gaps between each one. When I had finished I announced that if she wanted the last six, that they would be the hardest of all, she would have to ask me nicely for them. Through tears she requested the last six. I obliged striking her with great force. I thought she was going to use the safe word but she stubbornly refused even though she was screaming that it was too painful and for me to stop.

When I had delivered the last one and put the cane down next to her she asked me, or was it pleaded with me, to please fuck her. We had agreed that there would be no sexual contact in the session and although my cock was very ready I said I must not change our agreement. I did add that if we agreed to change this for a future session I would be happy to fuck her after caning her. She seemed very disappointed and agitated by my refusal but remained lying across the desk but brought her hand between her legs. There was not that much change in the moans that now got even louder than before.

I wasn't certain about my next move but decided to pick up the cane again and offer it to her bottom. She only uttered one word "yes" but it's meaning was crystal clear. She played with herself with no apparent urgency as I resumed the caning. I was striking her quivering bottom much less hard now and her moans were purely sexual. The next thing she said was also very short and to the point.

"Harder, much harder."

She started her orgasm just as the cane landed for third time. I listened to the sounds she exploded into to, to try and deliver the cane for as long and with the right force for her needs. I need not have worried as I kept on for what seemed ages until in a quiet voice she simply said "thanks". All tension was now gone from her body but I did notice tears rolling down her cheeks.

When she regained enough composure to stand up she gave me a lovely hug and said that it had been everything and so much more than she had hoped for. She said she would love to experience it again but asked whether I would be happy to fuck her after the caning. I promised her I would and we arranged to meet a month later. She became my first regular client.

Another early client.

This lady was the first who wasn't at least as old as me. She was the daughter of the best friend of one of my clients who had recommended me. As usual I met up with her and made all the arrangements to meet at a later date. It was the first of my clients who had specifically wanted me to dress up as an old fashioned headmaster. As I had pretended that I was a retired headmaster this was not unreasonable. The lady was also going to dress up for the caning and the role-play was agreed.

The game started with her knocking on the door and me calling her into the study. I had rearranged things as much as possible to look like a headmaster's study. The schoolgirl outfit was excellent (she had hired it) and as she walked in with her head bowed it was not hard to think that she was indeed only eighteen not the 21 she was. Having told her to sit down I pretended to go back to completing some paperwork. I then started to lecturer her about the reasons she was being punished.

"You sneaked out of your dorm after lights out and were found smoking with a group of older boys some of whom don't even attend this school. According to the report there was alcohol present at this gathering and that you were fraternizing with the boys in an inappropriate manner."

"But sir."

"I do not want to hear your lame excuses. These offenses are more than enough to get you expelled."

"Please sir I will take any punishment but please don't expel me. I have always worked hard."

"It is true you have worked well and generally have a very good record here. I do not wish to expel you, as it will give the school a bad name. Usually for the worst offenses the maximum for the girls is a dozen with the cane but today I will decide when you have had adequate punishment. Do you agree to this?"

"Yes sir, thank you sir."

"I promise you Jenkins you will not be thanking me when your bottom feels ready to explode. Given the nature of the offense your knickers will be removed after the first six and the remaining punishment applied to you naked bottom. Now approach the desk and lie full length across it taking hold of this side of it."

When she was in position I took my time going round the desk. She was not tall and to reach the far side of the desk she was standing on tiptoe. Her short school skirt had ridden up her legs I could make out a couple of inches of her bottom covered by large dark blue school knickers. I took my time tucking her skirt into its own waistband, adjusting a number of times so that I could enjoy the view and build the anticipation. The knickers were thick but I did think that I could detect the aroma that indicated that she was aroused. I spread the knickers so that they covered as much of her bottom as they could.

Her bottom was full but very shapely with a firmness that suggested playing of sport or using the gym. With her in place I stood to her side ready to cane her. It felt right to build even more tension and anticipation so I started to lecture her again while gently tapping her knicker-covered bottom with the cane. Even this gentle tapping elicited a quiet moan from her.

I could not delay much longer and landed the cane firmly but not hard as I finished talking. With all the anticipation it was still a surprise to her and she sucked in her breath before moaning much louder. By the time I had delivered the cane three times light colored marks were just beginning to appear each side of her knickers. I took my time delivering the first half dozen and while they would certainly sting nicely they were not harsh.

"Those first six were mere taps compared to what you can expect next. You were also protected by your very substantial pants that I will now remove."

My next move was probably my least headmaster like so far as I knelt down behind her magnificent bottom. So many thoughts and desires crossed my mind as I found the waistband of her knickers and very slowly started to peel them off her very round bottom. She eased her hips off the desk to allow me to slip them down until they bunched just where the roundness of her bottom met her legs. My face was inches from a beautiful bottom with gentle cane marks making it even more exciting. I wanted to bury my face into the vision in front of me but had to settle for a very quiet but deep breath in. If I hadn't been certain of her aroma before I was left in no doubt now as the sweet smell of arousal filled my nostrils. I had to pull myself together as I eased the knickers further down. As I did so they turned inside out as they were trapped between her legs. The sight confirmed what my nose had already told me. Her plump pussy lips were moist and had dampened the gusset of her pants making completing my job of removing them even more difficult.

Eventually I could not take any more time knelt behind her and reluctantly stood back up. Without being asked she spread her legs wide meaning she was back on a slightly shaky tiptoes. I was slightly surprised that the view this left for me included the dark crinkled skin of her anus and most of her plump red pussy lips. Fighting my urge to simply fuck the helpless girl in front of me I positioned myself so I could recommence the caning.

The next strokes were much firmer and her cries were now of real pain. She pleaded with me to stop or at least strike less hard, but I knew this was not what she really wanted. If she had wanted me to stop she would have used the safe word agreed. Towards the end of the next group of six she started calling me names as well as her pleading and sobbing. The stripes on her bottom appeared almost immediately and although they were red they did not threaten to break the skin. After this six I gave her a rest and actually went round the desk and sat back down.

I reminded her of the names that she had been calling me and said that she needed to apologize to me or else I would need to cane her further. Without thought she exploded in apparent anger calling me a dirty old man who loved inflicting pain on innocent young girls. Well she was far from wrong, although "innocent young girls" was pushing credibility a little. I wasn't sure that she had stayed in the role-play with this response as it didn't indicated that she wanted more from the cane, or not. Knowing the safe word was available to her I stayed in character.

I lectured her more giving the heat in her bottom time to spread and develop before returning to start the caning again. I struck as accurately as possible missing the existing stripes that had now started to turn purple as well as red. I was amazed looking at her bottom that she wanted me to carry on but clearly she did. I did not strike her any harder than the second set but she was immediately sobbing pleading and moaning loudly. She did stop the name calling, which indicated to me she was really reaching her limit. She was clearly counting these as immediately I had landed the sixth blow her body slumped and she exhaled all the air in her lungs.

This was where the role-play was floored. What she wanted was to have a matron summoned who would apply cream to her damaged bottom. It was agreed that I would apply a cream very gently to the damaged area and she would have to use her imagination. She closed her eyes and I said nothing as I traced each stripe with a cream loaded finger. I was as gentle as possible but this was still a painful experience for her. It took some minutes to cover the whole area and the longer it lasted the more she moved her bottom up to meet my fingers. She was no longer holding the far side of the desk as her bottom gyrated such that my fingers were delving deeper between her swollen cheeks until I was grazing her anus.

When my finger first made contact with the crinkled skin the moan was of pure sexual arousal. I repeatedly brushed gently across her anus as if by accident. We both knew it was far from that. I ventured further applying cream as I went until I made contact with her pussy. There was no need to apply cream here as it was producing copious amounts of its own. The "matron" spoke for the first time and I told her it was okay for her to enjoy the feelings she was clearly enjoying. She made little protest sounds but her body made it clear that she wanted this to continue. I did not let my fingers enter her pussy but used my palm to caress the hot, swollen, red and very wet area. Again her body told me what it wanted as she arched her back so that my fingers for the first time reached her clit.

I applied very little pressure, as I knew she was on the brink of orgasm. It took only a matter of seconds before she swore badly and exploded on my fingers. She rode my fingers that I simply tried to keep in contact with her clit. She was very verbal as her body shook time and time again. It was a mixture of swearing and cursing, calling me names and yelling "no" many times.

She had not seemed to finish her violent orgasm before she swore at me and ordered me to fuck her. She was up on the desk on her back with her legs wide apart within seconds and I was greeted by the sight of very open and ready pussy. I didn't see the view for long as I entered her fully and firmly taking hold of her hips and fucking her violently. I knew this was what she had fantasized about and although I would have much preferred to enjoy a more considered mating I complied with her wishes. I knew I would not last long fucking as we were but was amazed as she triggered my orgasm by cumming again within a couple of minutes. I was not very aware of her orgasm as mine was so violent but she was still shaking with spasms for a little time after I finished.

Within seconds with me soft but still inside her she said that the experience had been absolutely brilliant and the role-play had worked perfectly for her. She asked me if I was okay and I laughed as I said it had been great for me too. We had arranged a further role-play before my limp prick finally fell out of her very wet pussy.

Some of my other clients

I built up a large clientele quickly without needing to advertise again. Word of mouth recommendations were much more comfortable. Not all of the sessions with new clients were successful but most came back again with many becoming regular clients. Not all clients wanted the sessions to involve sexual activity but those that did varied greatly. Although I originally only offered caning many of my clients preferred whipping or spanking. A small number just wanted caning strapping or whipping with no other involvement.

One of these clients developed her sessions until they followed a regular pattern. She would go over my knee and be spanked through her panties. Then her panties were removed along with any other clothes she was wearing. When she was settled over my knee again my left hand would be between her legs while I spanked her with my right. The spanking was never hard but was for a protracted period. I would sense her arousal growing but knew she wanted this to grow slowly as the spanking continued.

This way her bottom turned a lovely flushed reddish color but never looked angry. I never knew how but after what could be in excess of half an hour she could somehow indicate that she wanted me to step up the fingering of her by now saturated pussy. I would keep the spanking constant and she would without warning explode on my fingers. As she did so she squirted fluids all over my hand and carried on doing so until her orgasm gradually faded. She would always offer to bring me to orgasm as a thank you but I knew she didn't really want to, as she appeared completely spent.

Another client also loved to be spanked over a long period of time. This was different as she clearly became very aroused as I spanked her naked bottom but she never actually orgasmed while with me. She told me that she came to me as her husband would not spank her but she would become so aroused by my spanking her she would return to her husband after our sessions for the best sex they ever enjoyed. The husbands' not being prepared to spank their wives was a very common theme with my clients. Some, as this lady did, shared their enjoyment of our spanking sessions with their husbands but others could not tell them. Arranging these sessions were trickier as my clients bottoms were clearly marked some for many days.

Then there was Cassie. She was a friend of one of my regular young clients. Cassie was about 21 and engaged to an older man who had a big international job that meant he was away a lot. Cassie said that he was quite unable to meet her sexual needs that she admitted were extremely high. She didn't want to cheat on him but felt if she was punished at the same time as getting sexual pleasure it wouldn't feel like she was cheating. I am not sure that she really believed what she was saying but who was I to argue. I realized during our first session that she wasn't really into pain much. She allowed me to spank her but after a brief warming of her gorgeous bottom she asked me, or nearly ordered me, to fuck her. She was so stunning that I could refuse her little and she quickly had two orgasms before I had one. She did not finish there and was soon down on me bringing my soft cock back to life. I fucked her the second time and she orgasmed again. I had had enough by then and faked an orgasm and ended the session.

Cassie's sessions fell into two categories. Firstly, she asked to be spanked to justify getting me to fuck her. Secondly, it was to punish her for what she had already done. Gradually these became the norm and she did actually require me to punish her a little bit more forcefully. The most memorable session was when she admitted being fucked by three men in a gangbang and required me to cane her. She also admitted that it had been the best sex ever. I caned her soundly but even then as always she pleaded with me to fuck her. Her single orgasm was the most spectacular I saw her experience.

I thought I had experienced most things before I started offering canings but I was wrong. Some of my clients wanted to use various sex toys during the sessions. Usually this involved them inserted in either their pussy or their bottom as I spanked, whipped, strapped or caned them. There was one rather large lady who always kept her knickers on and due to her size and positioning never exposed her pussy to me. Due to her large size her bottom was able to tolerate the cane applied with significant force. As her canings proceeded her hips started to thrust as if she was fucking an invisible cock. On the third or fourth visit the large dildo she had inserted moved and I became aware of it for the first time. I simply took hold of it and held it in place as I caned her and she exploded into her best orgasm yet. She was apologetic about using and hiding the dildo from me but I reassured that it was okay with me. After that day I always used a dildo or vibrator on her as I caned her. She loved it.

The most effective toy used in conjunction with spanking, whipping or caning was a small vibrator shaped in a "c shape". This could be inserted either before the punishment or during it. It held itself in place with one end inserted in the pussy a few inches and the other end covering the clit. It has a remote control that enables it to be turned on or off as required. It was Sandra who showed me this and asked me if she could wear it and I could control it. I was delighted to oblige and managed to use the vibrator as I spanked her. Her sexual excitement was very easy to read and enabled me to keep her on the edge of orgasm as I delivered groups of six increasingly hard spanks. It was Sandra who said she could only take one more set of six. She was four into this set when her orgasm started with a violence I have rarely witnessed.