Man Offers a Caning Service Ch. 03

Chapter 3

I am afraid I cannot write about a meeting with Kristina, as it has not taken place. I am still hopeful that it might.

Breaking my own rules - 1

Recently I have broken my own rules as regards sessions with my clients. The first time was with one of my favorite clients who was also one of my first. She has always asked me to call her Anna even though I know it is not her real name. Anna is one of my younger clients. She has always become very easily highly aroused by being spanked. She did try caning once but decided it was not for her. The agreement we have is that however much she pleads with me to fuck her after the spanking has stopped I must refuse. This has always taken all of my willpower as she has the most stunning body. She says she is always desperate to be fucked and orgasm after being spanked but wants to save this for her husband. I am delighted to say she is not the only one of my clients who uses me as foreplay before joining their partner.

After one very intense session, during which I did wonder whether she would orgasm over my knee, she asked me whether next time she could invite her husband along so that he could fuck her straight after her spanking. I like to think I am not homophobic but I have no interest in men and had never allowed a sexual partner to accompany my clients. Anna was very persuasive and with some concern I agreed. She had always told me that her husband knew all about our sessions and was delighted to welcome her home after each one. I did insist on a couple of conditions. One was that I did not want to be able to see him while I spanked her. The other condition was obvious that I wanted absolutely no contact with him. Anna was delighted as she left asking for an appointment ASAP.

I was less uncomfortable as I had expected to be when she turned up with Rob (no idea if this was his real name). He was happy to sit in the corner out of my eye line. Anna was always nervous before a spanking but that day she seemed even more jumpy. As always she stripped off all her clothes very quietly and without looking at me. She did however glance at her husband each time she removed a garment. When completely naked she stood in front of me and in a meek voice.

"Please will you spank me I have been very naughty."

She waited until I held out a hand to pull her over my lap. Her eyes were pleading but submissive as always before she went across my fully clothed knees. I rested a hand on her round but taut checks and told her exactly what I was going to do to her and more specifically her bottom. I never spank her until she is settled and relaxed. I caressed her warm bottom while talking quietly to her. Finally her body sagged and I knew it was time.

There is never anything rushed with Anna. The spankings start almost gentle and build gradually until they are very firm. No two sessions are the same. Sometimes I spank her for three or four minutes but usually it is much longer. Without saying a word it is Anna that has total control on how long and how hard the spanking is. I am not even sure how but the communication is always clear. That day her body responded very quickly and I was soon spanking her very firmly.

Her bottom was pushing up to welcome my hand before dropping down to try and find something to rub herself on. As the session went on she always found some part of my legs to squeeze against. I have to admit that it almost felt like she was making love to me. My cock was as always hard but kept out of harms way. The final stages of spanking Anna were when she found her voice. Completely quiet until then she now started urging me on (or was it really herself). She pleaded for more and harder spanking but this was interspersed with requests to fuck her. I was a bit concerned that Rob would correctly think that she asked me to fuck her each time but decided not to say anything.

This session of spanking ended as it always did. Before delivering the final half dozen hard spanks I always caressed her now hot cheeks allowing my fingers to slip between her legs just enough to confirm her complete arousal. Her sigh was accompanied by her lifting herself so that my fingers became coated by her aromatic lubrication. The final six were then delivered hard and fast during which time she swore at me and screamed out her agony.

Within seconds of the last spank landing she was on her knees on the floor facing me. As I heard movement from behind me I made to leave them to it. Anna however had other ideas.

"Please stay I want you to see what spanking does for Rob and I."

Rob was behind her on his knees very quickly and it was clear that penetration was exceedingly easy and pleasurable to both of them. Her eyes were bright and lively as she held my gaze with a look of pure ecstasy. She begged and pleaded with him to fuck her harder. I wish I could say that they fucked energetically for hours cumming numerous times but in fact she exploded in less than 30 seconds triggering him to cum noisily.

She claimed it was her best ever orgasm and Rob seemed delighted if a little spent. He asked Anna whether she wanted me to fuck her and very nervously she said, "yes please". I said I would love to but that I never fucked clients unless we agreed before the session. Rob looked surprised by this reply but laughed as he said,

"So you do fuck some of the women you spank? Do you not fancy Anna (not the name he used)?"

"I think she is drop dead gorgeous but we agreed that however badly either of us wanted to the spanking should remain foreplay for Anna and you."

"In which case we both give you full permission to fuck the living daylights out of Anna at your next session. I will look forward to the second fuck after her spanking as these are always the best as they last more than a minute."

We all laughed at this. My erection that I had contained in close fitting underwear threatened to explode at the vision of fucking the stunning Anna. The next session has not happened yet but I am nervously excited by the thought.

Breaking my own rules - 2

Having agreed to let Anna's husband join in a session, and it working out well, I reconsidered the request from one of my other clients. Lin had asked me to agree to a session with Bren who had been the client who had introduced us. She asked that I spank them both during the same session. I did see a problem with this as Bren always asked me to penetrate her after her spanking whereas Lin just received a spanking. I had no idea how honest the two were with each other but decided to agree to the session and not ask questions.

Both ladies were in their early to mid thirties and super fit as they went to the gym together. They arrived together and there was a buzz between them as they walked in. Usually they both received their spankings over my lap but we had agreed that they would both lean over the low back of the sofa so that I could spank them at the same time. Lin nearly choked when Bren stripped all of her clothes off before taking her position. She looked at me with a questioning stare. I offered no reaction and was delighted when she followed suit. It was the first time I had seen her small firm boobs that were topped by hard thick long nipples set on nearly non-existent areola. Their dark color contrasted beautifully with her pale skinned boobs. I could not understand why she seemed to try and hide her beautiful chest from me before settling beside her friend.

When I walked round behind them the view was wonderful. Bren had her legs wide apart and her very adequate bottom stuck well back. Lin was much more modest with her legs together and her hips pushed hard against the sofa back. I scolded Lin for this and ran my hand up the back of her legs as they eased apart. As I reached the top of her legs they opened at exactly the right time for my finger to run from her pussy right across her anus. Her quiet verbal protest was in complete contrast to her body that pushed back to increase the contact. I was a little relieved, as I had never touched Lin so sexually previously.

Given that Lin's spankings were always longer and harsher than Bren's I started by giving her half a dozen firm spanks. I had to create a little gap between the two women before delivering the same number to Bren. I noticed that while I had split them up behind the sofa they were now clinging to each other on the other side. It was nice to see and I did wonder whether their closeness would develop further. I delivered two more groups of six to each bottom with Lin's being harder as I knew this was her preference. Sessions with Bren usually involved me caressing her spanked bottom half way through. Well I say caressing a more accurate description would be masturbating the excited Bren's bottom and pussy. She said that the second half of the spanking was blissful if she was on the verge of orgasm when it started.

I had a decision to make at this stage. Did I masturbate Bren now and see what reaction I got from Lin? I rested a hand on Bren's warmed backside and her reaction made it very clear that she was ready for my hand to do more than spank her. She had made the decision for me and my hand reached between her legs to find her pussy as wet as I had expected. I heard Bren say something to Lin but could not hear what it was. What I did hear was the single word that Lin half whispered and half growled, "please". I was slightly nervous of my interpretation as I slipped my hand between her legs in response. Bren was beautifully wet but Lin was dripping right across the area from beyond her clit right round to past her anus. I had only once in my life experienced a woman this wet and she... well that is another story.

I used a hand to caress/masturbate each woman. I was unable to tailor make my actions so they both got treated equally. Given the slippery lubrication of the whole area between Lin's legs I found myself concentrating my decisions on what this hand found. My fingers reached as far as her clit but my thumb was naturally teasing her dark anus. Bren's anus was relatively dry to the touch but almost without thought my thumb eased into Lin's wet and relaxed anus. A little push resulted with my thumb penetrated Bren's bottom. I now had a thumb up both bottoms and my fingers playing with two wet pussies. I was delighted as both women pushed back and forward first to ensure my thumb was fully buried and then to gently fuck my thumb. It was hard to locate Lin's clit as the whole area was awash with her lubrication. I did not concentrate on Bren's clit as we both knew that she would not want to orgasm just yet. I flattened both hands out so that they played with the whole of both pussies. Lin's was so wet that by accident my fingers did probe inside her a couple of times. Having never touched Lin's pussy before or seen her close to orgasm I was unable to read her body. This became redundant when Lin screamed loudly and exploded on my fingers. I had had no intension to bring her to climax but worked her spasming body to give her every bit of pleasure I could extract from her excited body. My hand playing with Bren replicated what I was doing to Lin but I was unable to concentrate on where her arousal levels were. When Lin's body sagged I turned my attention to Bren. She was ready, ready for more. I could have carried on and brought her to orgasm or spanked her more which I was sure was her preferred option.

Lin remained where she was as I started to spank Bren again. The second session of spanking Bren was always a little firmer. When I paused there was a whisper from Lin, "Please more, I need more." I had not known how to progress with Lin but now she had made it very clear. I am often asked how I decide how much and how hard to spank and my simple answer is that almost always my client tells me. This communication is more often than not non-verbal. I knew that Bren would not want much more spanking (her spanking is lighter and less than nearly all my clients). I therefore decided to be very firm with Lin whose sessions usually were long and rather harsh. I delivered a total of three groups of six to each woman after the masturbation. By the end of this Bren was totally primed for the penetration that was always the culmination of our sessions.

Bren simply moved round to front of the sofa and knelt down with her beautifully prepared bottom high in the air. I thought Lin was going to join her but was slightly disappointed but not surprised when she did not offer me her pussy. Instead she sat on the sofa close to Bren and opened her legs wide. Faced with this view I couldn't believe that my first thought was that the sofa would need a good cleaning. There was clearly some exchange between the two women and they both moved until Bren's mouth was buried in the very hot grotto that was Lin's pussy. There was something that made me think this was a first but of much more interest was how my dressed erection slid with the greatest of ease into Bren's inviting pussy.

There are few visions that you know will stay in your memory for the rest of your life. This was certainly one of them. Fucking a female whose bottom you have just made very red would normally be everything you can ask but when you add the view of her going down on another woman at the same time - well. This wasn't the end of it as Lin was now playing with her extraordinary nipples with total abandon. She had gone slightly light on pain during the spanking, but she was making up for it as she was very hash with her huge hard nipples. I pride myself on being able to control myself and last as long as most females require but I knew this was going to be the ultimate challenge. Fortunately Bren came to my rescue. I suspect that her quicker than usual climax was triggered by Lin exploding loudly in her second of the day. I enjoyed part of Bren's orgasm before I lost control and emptied myself into her protected body.

When the dust settled it was a hugely embarrassed and apologetic Lin who was very verbal. She apologized to Bren for asking her for oral and me for not offering to let me fuck her. I reassured her that she had nothing to apologize to me for. We had never had any penetrative sex and that was fine by me. I am often left highly aroused and unfulfilled after a session with a client. This time was unusual, as I had taken the precaution of taking a blue tablet before the session, as I had never had a session involving two women. While I had enjoyed a strong orgasm the whole event had left me very aroused with an erection that was not going down any time soon. I wish I could say that Bren and Lin relieved me of my erection but I think they were much more bound up in how their relationship had developed.

This happened only a few days ago and I am far from certain that Lin will want another session with me. Bren however kissed me on the cheek as she left and it was clear that she would be back soon. I wondered whether she would invite Lin the next time.

I hope I have made the right decision.

I now have so many clients that I have become very choosey about taking on new ones. New approaches now almost always are referrals from existing clients. The last such approach was from a client who has been with me for a couple of years (usually visiting every three months). I thought she was very early 30s but she said she had a daughter who was now 18. She said that her daughter was rather headstrong and she wanted me to have a session with her daughter to punish her for her recent behavior. I immediately made it completely clear that while some of my clients enjoy the fantasy of punishment and even being forced this was always their fantasy and not the actual purpose of the session. (I did, however, later reflect how one of my clients does see me as a substitute for the confessional but this was different.) She dropped the subject until after her next session. She then asked me again to have a session with her daughter. She said that the two of them were very close and she had admitted to her daughter how her sessions with me were very special. Her daughter had requested that her mum asked me again to at the very least meet with her.

I agreed to this but made it clear I was not committing. I insisted that I had time alone with Carly to ensure that I was happy with any potential session. We met a few days ago and Carly was so like her mother in looks, looking much more like a sister than a daughter. Like her mum she was stunning. There was only one big difference between the two. Carly was into bodybuilding and although no more than 5 foot 6 or 7 was heavily muscled. She made it clear that her mum had been very honest, totally honest, about our sessions together. She knew that our sessions always ended with us having sex. I was uncomfortable about her age and inexperience. When I alluded to this she knew exactly what I was suggesting but her very knowing smile said more than words ever could.

"Don't worry I can take everything you can dish out. I cannot wait."

She convinced me but I was still a little nervous, as she was young enough to be my daughter. I agreed to a session and in the days since have become extremely excited about the prospect. I hope to write about it soon.