The school trip

I was the oldest pupil on the school trip to Amsterdam as I would be starting my final year at school the following term and because of my age I was already eighteen. I was surprised none of the others from my year wanted to go on the trip but they obviously thought it wasn’t cool to be going on a school trip at their ages but what they didn’t seem to realise was that we would have a bit more freedom to explore and that Amsterdam is an incredible city. I did have a bit more freedom and had been allocated one of the single rooms in the hotel on the trip but the corollary of this was that I was supposed to be a bit more responsible and set a good example for the younger pupils, particularly as I was a Prefect at the school. It was a nice hotel we were staying in and it was pretty much in the heart of the city.

One of the staff in the hotel is a really attractive young thing and I regularly see her working in the restaurant at breakfast and then in the bar in the evenings. She probably isn’t more than a couple of years older than me and I had developed an instant crush on her and she seemed to know it as well. Karin always tried to serve me at breakfast and also in the bar in the evening and she teased me mercilessly with her flirting. One morning at breakfast Karin had slipped a note into my back pocket as I was getting a refill of orange juice.

“I’m finishing work at 7pm this evening I hope that you will be around to see me” was what the note said and I gave her a smile and a nod of my head once I’d read the note. We were going out on a boat trip that evening but at dinner I started to complain of a migraine and was excused from the trip and because my reputation at school was for being a ‘good boy’ none of the teachers remained behind to keep an eye on me which is what I’d expected would happen because they really needed four of them to supervise the party on any trip out. As soon as the pupils and teachers had left the hotel I slipped down to the bar where Karin was waiting with a drink so I bought her another one and got myself a beer as well.

We chatted for a few minutes before Karin took the lead and gave me a kiss which I soon returned and as I was doing so my hand was resting on the lovely curve of her bottom. As soon as we had finished our drinks we headed up to my room and were snogging all the way up in the lift and this continued as we got into the room. Karin took the dominant role, probably sensing my relative inexperience, but I would have been happy to let her take the role anyway because all the girls I’d gone out with had taken the lead in the relationship. We were soon naked and Karin notices just how hard my cock is. Karin stats to play with my cock getting it even harder and she reached into her bag and pulled out a condom before rolling it down the length of my shaft.

‘I want you to fuck me from behind’ Karin says as she is getting herself onto all fours on the bed giving me a gorgeous view of her pussy which is very inviting and already quite wet and before I push my cock into her I lean forward and give it a deep kiss pushing my tongue into it so that I can get a taste of her nectar and this makes her body spasm. I slowly pushed my cock inside her savouring the sensations before Karin started to dictate a tempo for me to follow which I did even when it got harder and faster. Karin had reached a hand back between her legs and as my cock was slamming into her she was playing with her clitoris until eventually she couldn’t stand it any longer and cried out in her climax which seemed to drag the cream up from my balls giving me the most explosive climax of my life.

Karin collapsed forward onto the bed and looked at me with a lusty look in her eyes and I joined her starting to kiss her as one of her hands was playing with my cock getting it hard again really quickly whereupon she rolled another condom down it.

‘Fuck my arse’ she instructed in her sexiest voice and took a tube of lubricant from her bag and threw it back to me.

‘Use lots and lots please’ she said and I took a large quantity into my fingers spreading it around the tight little hole before pushing my fingers in slowly feeling the muscles gripping them as they went in. I kept adding more lubricant to the mix and was getting three fingers in more easily before I pushed the head of my cock against her hole having smeared lots of lubricant over the condom. I pushed in very slowly and as I was doing it a long moan escaped from Karin’s lips but then when I eventually pushed past her sphincter she gave a deep sigh of pleasure. I loved the feeling of her body gripping me tightly as I slowly eased my way in and out of her tight hole and again she started to dictate the tempo for me. Karin continued to play with her pussy as I was fucking her arse and it wasn’t long before she was climaxing again but this time I managed to hold my own climax back and continued to fuck her until eventually she had me pull out and remove the condom. Karin spun round on the bed and took my stiff cock into her mouth bringing me to a climax very quickly with her wonderful tongue and swallowing all of my cream. We cuddled up together on the bed after this recovering some energy.

‘That was very good my lover. Have you ever gone down on a woman?’ Karin asks sexily.

‘No apart from kissing your pussy before fucking it I’ve never gone down on a woman but I’d love to learn’ I answer.

‘It will be my pleasure to teach you and if you learn your lessons well then all girls will love you for it’ Karin says. Karin rested my head on a pillow before she lowered her pussy down over my face. It is still very wet from our earlier exploits and I lapped my tongue along its length to get another taste of her nectar. Karin grinds her pussy around my face so that I am completely smeared in her liquid and I love the sensations but then she starts to give me lots of tips and tricks to try on her. She was giving me lots of encouragement and I could feel the juices leaking out of her pussy as I was putting her teaching into practice. I absolutely loved it and then Karin climaxed giving me a feeling of absolute joy that it was me who had caused it.

‘It’s your turn now Ken. Use your own initiative and try to make me cum again’ Karin instructed.

I was getting pretty close to my target when the door to my room opened and Miss Innes walked into the room to see how I was feeling having returned from the boat trip. Miss Innes is the youngest, and hardest, of the teachers on the trip and she is also the most attractive by a long way.

‘Feeling better I see Kenneth. There never was a migraine was there? You just wanted to get into Karin’s knickers didn’t you?’

‘Yes Miss Innes that is true. What are you going to do about it?’ I asked having seen no point in denying anything as the evidence was clear for her to see particularly as Karin remained sitting naked on the bed.

‘Well I could tell Mrs Smith’ Miss Innes said.

‘Please don’t do that’ I answer because I know that if she does I will almost certainly be sent home in disgrace and quite possibly expelled from the school as well which I didn’t want.

‘But I think I will deal with this matter in my own way’ Miss Innes concludes before leaving the room.

‘Karin, you might want to leave now as Miss Innes has probably gone to fetch a tawse so what follows will almost certainly be very painful as she is the hardest teacher in my school’ I say.

‘I will stay Ken. We are both guilty and it wouldn’t be fair for you to take the punishment for both of us. Thank you for the warning though’ Karin says before giving me a kiss which she’d just broken off from when Miss Innes walks back into the room holding what looked like her heavy three-tailed tawse.

‘Karin, I have no authority over you so I would advise you to leave this room now unless you want to feel this on your bare bottom’ Miss Innes says giving Karin the same option as I had.

‘We are both as guilty as each other Miss so I will take my share of the punishment’ Karin says having sat defiantly on the bed.

‘Very well Karin. You will both receive twenty four strokes of the tawse on the bare bottom delivered in alternating sets of six. Kenneth you will receive the same punishment each night until the end of the trip’ which is another two nights after tonight. ‘Stand at the end of the bed Kenneth. Now bend over and place your hands on the bed and do not move from this position until I tell you to do so or I will start the punishment again. Karin watch carefully as you will be next’ Miss Innes says.

I have been punished once before by Miss Innes so know that this isn’t going to be easy but even so her first stroke takes me by surprise as she is drawing as hard as she possibly can. Each stroke lands with such a loud crack that I’m surprised that none of the other teachers come to find out what is going on. Each stroke gives a deep and instant pain but I am gritting my teeth so as not to give Miss Innes the satisfaction of a cry and so that I can show Karin that I am tough. Karin showed no fear as she took up the position for her first six strokes and like me she didn’t make a sound even though Miss Innes was giving her exactly the same level of punishment impressing me with her stoicism. Bending over for the next six strokes was a challenge and I found that the pause made the seventh stroke even worse and this pattern continued throughout the punishment. By the end of it my bottom felt as hot and sore as it had ever felt and there were some impressive marks across it as I saw in the mirror in the wardrobe. Karin’s bottom was equally heavily marked by the end of the punishment and I was surprised when Miss Innes just left the room without bothering to separate us.

Karin was still very horny and she laid me down on the bed and coaxed my cock back to life before riding me to another mutual climax.

‘How did you manage to take the punishment so well and retain your arousal?’ I asked in absolute amazement as we were cuddling up together.

‘I love being punished and have starred in many films with much more punishment than that although I have to say that your teacher was very impressive. Would you like copies of the films to take back with you? You also took it incredibly well Ken so how would you like to star in some of the films?’ Karin explained and asked.

‘I’d love copies of the films and I think I can see where you are coming from in loving being punished so yes I think I would like to star in the films as well’ I answer as thinking about it has made me horny.

‘I’ll bring copies of the films to you before you go and give me your phone number and email address and I’ll get in touch when I’m next over doing some filming so that you can come and watch and maybe take part’ Karin says before giving me a goodnight snog as it didn’t seem sensible for her to spend the night and run the risk of being caught by Miss Innes again the following morning as I’m sure she would check up on me.

Karin and I managed to sneak another night together on the final night of my trip and it was just as wonderful as that first night even though Miss Innes did punish us both again but having thought about what Karin said I really was beginning to enjoy being punished. At the start of my final year at school I discovered that Miss Innes was going to be my teacher for Mathematics and she kept me back at the end of the first lesson.

‘I presume that you remember what I did to you when we were in Amsterdam Ken and that I can therefore expect no problems from you this year?’ Miss Innes said.

‘Yes I do remember the punishments very clearly Miss Innes and I will try hard not to give you any problems this year’ I answer although I wouldn’t be too averse to being punished by her again having done a couple of films with Karin during the summer.

‘Good boy’ Miss Innes said before dismissing me from her room although we both knew that I would be kept behind more than once during the year ahead.

The golden girl

I have a fantastic job as the live-in bar manager for a hotel in the Highlands of Scotland having originally worked for them as a barman during the long summer vacations of my degree. I have full responsibility for the main hotel bar and also the bar in the basement club both of which are heavily used by hotel guests and the local community. It’s a wonderful hotel to work in because it’s cheap and at the hub of many different outdoor activities which means that it’s regularly filled with schools and students giving a real buzz to the place. I love the job I’m doing because I’m very into outdoor activities so it means that whenever I have any time off I’m able to get out into the mountains or onto the water for whatever activity I feel like at the time. We have lots of casual staff coming to work in the hotel during the summers so there are plenty of opportunities for sexual liaisons with them and also with guests of the hotel and I only very rarely turn these chances down so it is always enjoyable.

At the very start of one summer we have a large party of girls staying in the hotel from a very posh private school in the south of England and the older girls in the party are allowed to use the hotel bar if they are sensible and they all are because the teachers are never that far away and they are all martinets from what I’ve seen. There were stories circulating amongst the hotel staff about having seen and heard the teachers applying the cane to the girls which I certainly believed could be true even though I hadn’t witnessed it myself. I had to admit that the thought of some of the girls bending over to be caned was a highly arousing one but there was also a twinge of arousal at the thought of some of the teachers doing the same thing to me for having these thoughts.

One of the girls in the party seems to be the real golden girl with all of her fellow pupils and teachers. Isabella stayed behind in the hotel one afternoon when the others went riding claiming that she wasn’t feeling well and wanted to sleep. Because Isabella was the golden girl none of the teachers remained behind to supervise her so as soon as everyone had gone she came down to the hotel bar to talk to me, or rather to chat me up. I knew that Isabella was old enough to drink because she’d left the school before the start of the trip but had been allowed to come on the trip as long as she continued to abide by the rules so when she asked for one I bought her one but did comment.

‘We’ll both be in trouble if we’re caught’.

‘Yes I’ll be caned if the teachers catch me but I’m certainly not going to be telling them and I’m sure you’re not either’ Isabella answers.

‘No I’m not going to say anything. So it’s true that the teachers cane you then’ I say.

‘Yes it’s true and it’s a regular occurrence but all of us older girls see it as a badge of honour to wear the stripes even though it is always a very painful ordeal at the time. So does it interest you then Ken?’ Isabella asks.

‘Yes when the other staff have been talking I’ve been interested in it and also wondered what it would be like to be on the receiving end from some of your teachers, who look like they are real dragons’.

‘Well why don’t you get cover for the bar and come up to my room where I can show you the marks of the caning I received a couple of days ago. Yes some of the teachers are dragons but some of them are pussycats and I’m sure that I could persuade one of them to give you a caning if you are that interested’ Isabella says with a wicked grin on her face.

‘Mmm that could be a very interesting experience’ I say wondering if Isabella was being totally serious or just teasing, ‘I’m coming off shift in half an hour anyway so that would be a good chance to see the marks on your beautiful bum but my room will be much more comfortable than yours’ I finish off.

‘Deal’ Isabella says before finishing off her drink and she heads out of the bar just before my staff member comes in so that there is a little bit of discretion for her because I certainly wasn’t worried by the attention. As soon as we are inside the dormitory block for the live-in staff we head up to my room which is on the second floor and one of the biggest rooms in the complex.

‘It certainly is more comfortable than my room. Sit down on the edge of the bed and let me entertain you for a bit’ Isabella says having looked round the room and when she spots my iPod connected to a speaker system she strolls over to it and looks through the collection of music which is on it.

‘There is some really cool stuff on here Ken’ Isabella says with a hint of surprise in her voice as she is selecting the music she wants to play. It is a very chilled out dance track that Isabella has selected and she starts to follow the rhythm perfectly with her very raunchy strip show which revealed a tight, toned body with very pert, perky breasts topped by rapidly stiffening nipples. To end the show Isabella came close in to me and turned round so that I got a wonderfully close look at the cane stripes on her bottom particularly when she bent over tightening both hemispheres of her bottom beautifully. There were six separate stripes in total and all of them are still a lovely pink colour. When I run my hands over them I can feel the slight hardness and roughness in the skin and the gentle touch brings a sigh from Isabella so I place my hands on her hips and start to kiss and tongue at each of these stripes. Shivers start to run through Isabella’s body and she tries to push her bottom back into my face as my tongue becomes even more teasing on the welts. We spend the next few hours teasing and playing with each other until eventually Isabella looks at her watch and realises that the rest of the party will be back from their trip very shortly.

‘I should get back to my own room so that I am there when the teachers check’ Isabella says, ‘Or of course we could see if I can arrange for you to be caned along with me Ken if you are still game’ Isabella adds.

‘I’m still interested what are you thinking of’ I answer.

‘Well I could go to Miss Prince who I’m sure would be prepared to cane you and explain that I’d lied when I said I wasn’t feeling well because all I wanted to do was stay in the hotel to have a drink and get to know you. This is the reason why I stayed behind and it will certainly guarantee me a caning. As for you I could explain to Miss Prince that you knew you shouldn’t have been serving me alcohol in the afternoon and you feel that you should be caned for this indiscretion. One thing we must not mention will be what we’ve been up to this afternoon as that will result in a very severe punishment for both of us but by the same token I would advise against lying to Miss Prince as she can spot a lie from a mile off and will tie us in knots until we have admitted the offence’ Isabella explains.

‘That sounds good Isabella. Miss Prince sounds a lot like one of my teachers from school, Miss Nicol, who got real pleasure from punishing pupils except in her case it was a tawse that she used. She also knew exactly when a pupil was telling the truth and when they were lying and you only made the mistake of lying to her once because the tawsing was so painful that you wouldn’t do it again’.

‘Yes that does sound a lot like Miss Prince which is why I’m sure that she will be delighted to cane you in addition to me. Unfortunately though her thrill in the use of the cane is also accompanied by a real skill and she is regarded as the hardest caner in our school’ Isabella explains.

‘Well I suppose if we’re going to do a thing we may as well do it properly by going for the hardest teacher’ I say confirming that I was up for it, ‘I wonder if it would actually be best if we are sitting in the bar when the others arrive back as this might stop her even thinking about the possibility that we could have been having sex’.

‘That’s clever Ken and it will almost certainly mean that she earmarks you for punishment as well as me. We’d better get changed and back to the bar pretty quickly if we are going to do this’ Isabella answers and we do get up and get dressed. I buy Isabella a glass of red wine and get myself a pint as we sit chatting in the bar about different outdoor activities waiting for the rest of the party to return and find us. We are actually taken by surprise because they have come in the back door and Miss Prince has gone up to check on Isabella but hasn’t found her in her room so she doesn’t look too surprised to see Isabella sitting in the bar when she walks in looking for her.

‘I see you are feeling better Isabella. It has either been a remarkable recovery or there never was an illness in the first place’ Miss Prince says leaving the statement hanging in the air for Isabella to ponder on.

‘No Miss Prince I am afraid I lied in saying that I was ill. I have seen Ken in the evenings when you have kindly allowed the senior girls to have a drink in the bar and yesterday evening he was talking to another customer about his love of downhill racing on the mountain bike and I wanted to talk to him about this and get him to take me out into the hills to do some as it is something I really want to do but I know that it’s not covered by the school insurance policy so you can’t let me do it’ Isabella answers and I’m amazed by how genuine she sounds in this answer.

‘So you have admitted to your lying over the illness and quite clearly you have been drinking and I am presuming that Ken has been buying you the drinks which is something I’m not at all happy about as he should know better as a responsible adult than to be buying anyone from this party alcohol, even if they have left the school and are legally entitled to drink. You will be caned for these two offences and I have to say that I’m not sure about the rest of your story either Isabella’ Miss Prince says.

‘Yes I accept that I should not have been buying Isabella drinks this afternoon and if you feel that I should be caned also then I will accept that’ I say trying to take the focus off of Isabella for a moment or two.

‘Well I suppose caning you will apply a more direct sanction that might make you think twice about doing something similar in the future and it will certainly be more enjoyable for me and all the other girls than reporting you to the General Manager of the hotel because if I am going to cane you both then I might as well make a proper example of you to try and deter any similar behaviour throughout the remainder of the holiday’ Miss Prince says and I’m surprised at the fact that the punishment will be given in public and it appears that it has also surprised Isabella as well to judge from the look on her face.

‘Now you two will come with me’ Miss Prince says and we leave our drinks on the table and I see the look of shock on the face of the barmaid who is working and who will have heard every word that has been said. We follow Miss Prince to her room where she interrogates us on what has actually happened this afternoon and as Isabella had said it wasn’t long before Miss Prince had us contradicting ourselves and each other until eventually Isabella admits the truth.

‘It is true to say that I have seen Ken working in the bar in the evenings when you have allowed us to have a drink and it is also true to say that I’d heard him talking about downhill racing on the mountain bike which is something I really want to do and know you won’t let us do but that wasn’t the main reason why I lied and stayed in the hotel this afternoon. I thought from the first time that I saw Ken that he was really attractive and I wanted to get to know him better without the other girls around so I made up the story about being unwell to give me the chance to do this. We had one drink and then went back to Ken’s room where we have played with each other but that is it’.

‘Is this true Ken?’ Miss Prince asks.

‘Yes it is true Miss Prince and I accept full responsibility for my actions and will accept whatever punishment is deemed appropriate’ I answer calmly.

‘Isabella you know very well that having any form of physical contact with men is against the school rules and even though you have left the school you clearly agreed, as did everyone, that while we are not at the school this trip would take place under the normal rules of the school so this is a very serious act of deliberate disobedience. Since you have left you will receive a more severe caning than normal in front of the rest of the girls and it will be explained to them that if you had been remaining at school you would have been expelled. Ken you would not have known about the school rules but I am sure that you could have guessed that what you and Isabella were doing this afternoon would not be permitted for a girl from this particular school so I am going to consider that you have broken the rules as well. Your punishment will be even more severe because I intend to ensure that you think twice before doing anything similar with other school parties that are in the hotel and because I’m sure that Isabella is not the only girl in this party who would have been tempted to do the same thing with you. As with Isabella your punishment will be administered in front of all the girls. Both punishments will take place in thirty minutes time in the kit room. Isabella you will receive eighteen strokes of the cane on your bare bottom and Ken you will receive twenty four strokes of the cane on the bare bottom. You will both go to the kit room and strip completely naked in readiness for your punishment’ Miss Prince says calmly.

Calm certainly wasn’t how Isabella and I were feeling as we made our way down to the kit room which is a large room set aside for the storage and drying of outdoor kit at the back of the hotel. As the room is designed for kit drying and kit preparation there are lots of tables and very sturdy clothes horses in the room but there is also a large empty space at the front of the room. Not wishing to anger Miss Prince any more as we were sure that she would have no hesitation in increasing our punishment still further we stripped completely naked and folded our clothes neatly at the front of the room. We stood facing the wall at the front of the room awaiting the arrival of everyone else and soon enough we heard the chatter of voices approaching the kit room. When each person entered the room there was an audible gasp when they saw us standing naked at the front of the room, suggesting that they hadn’t been told we were going to be punished and presumably then the reason why we were being punished was also unknown to them. When they all saw Isabella and a man they guessed the nature of the offences but this was about to be spelt out to them.

‘Isabella, Ken you will turn round and face the audience’ Miss Prince commands and we obey with a blush on our cheeks.

‘Girls, some of you will no doubt recognise this young man from the hotel bar and I can imagine that some of you may find him rather attractive. Well Isabella certainly found him attractive and this prompted her to lie earlier in the day when she told us that she was unwell and wanted to remain in the hotel instead of going riding. Well instead of recuperating Isabella went straight to the hotel bar and shared a drink with Ken and the pair of them then went to Ken’s room for the afternoon’ which brought a titter from some of the audience although some of them also looked a little nervous as if thinking it could so easily have been them in this position in the past. ‘Well such flagrant disobedience and lying will not be tolerated and Isabella will receive eighteen strokes of the cane on her bare bottom and Ken has accepted his share of the responsibility and will receive twenty four strokes of the cane on his bare bottom. Both of these punishments are being carried out in front of you all to act as a deterrent both for the remainder of this trip and for the rest of your time at the school. It is only because Isabella has already left that she is not being expelled with immediate effect anyone else caught in a similar position will be expelled. Isabella you will bend over the table with your bare bottom facing the audience so that they can clearly see the physical consequences that will happen to them should any of them be stupid enough to try similar behaviour’ Miss Prince says while looking round at the other pupils focussing her attention on some of the senior pupils in particular as if she knew that some of them had been doing the same thing but hadn’t been caught yet.

Miss Prince took a cane from the hands of one of her colleagues who’d been holding it and I watched Miss Prince flex it through the air and then bend it into an almost perfect arc both of which did nothing to ease my fear. Miss Prince tapped the cane a couple of times across Isabella’s bottom and then she drew the cane away before swinging it down at pace into the defenceless target in front of her. It landed with a loud crack and I saw Isabella tense her hands against the table and screw her eyes tightly closed. There was a rhythm to the punishment and it was soon being accompanied by vocal reactions from Isabella and I was just glad that I couldn’t see her bottom although seeing the pain on her face was pretty bad. As Isabella’s caning was coming to an end I realised that my own appointment with it was coming up and the fear started to grip at every part of my body and I tried to remember back to some of the punishments I’d received at school a few years ago but the only memories that remained were of the phenomenal pain that they had caused. By the final few strokes of Isabella’s caning her cries were impassioned and the tears were dripping off the end of her nose onto the floor.

‘Stand up Isabella’ Miss Prince ordered and it was with great difficulty that she did so and she turned to face Miss Prince on instruction which allowed the audience to see the tears streaming down her face but it also allowed me to see the heavily wealed state of her bum and some of them seemed to be leaking a little bit of blood where they had crossed the ones from a couple of days ago.

‘I hope that this has provided a sufficient lesson for you Isabella but rest assured it will be repeated if necessary. You will now go with Miss Innes who will take you to your room. Ken you will take Isabella’s place over the table for your caning’ Miss Prince says and I walk forward slowly.

‘I would advise you not to try my patience Ken because I will simply add a tawsing to your caning and I’ve no doubt being a good Scottish boy you will have experienced this in the past’ Miss Prince barks so I hurry up and place myself over the table feeling the warmth from Isabella’s body on the smooth wood. Because of my greater height I had to stretch my legs back a bit to get flat down over the table which didn’t really please Miss Prince.

‘Stand up Ken’ Miss Prince commanded. She spots a tightly rolled up sleeping bag in the room and she places on the table and then instructs me to bend over this. This puts a stretch on my legs and then forces me to dip my chest down steeply making my bottom the most prominent part of my anatomy by some distance and it also made it very tight strengthening my feelings of vulnerability. Miss Prince tapped the cane on my bottom just as she had done with Isabella and this felt bad enough but then I heard it swishing down and knew that I was about to receive my first ever cane stroke. All I felt to begin with was the impact but then milliseconds later the wave of pain flowed through my body and I gripped the table very tightly to stop myself from leaping up. This pain continued to build and seemingly when it was at its peak Miss Prince delivered the second stroke just below the first one. Somehow I’d remained silent and then the third stroke arrived and this was much lower on my bottom and it was much sharper bringing a yelp from me. I felt like I’d sat down in a patch of stinging nettles by the time we were even a quarter of the way through the caning. Somehow though I realised that I could see where Isabella was coming from when she said that all of the senior girls wore the marks as a badge of honour and I would certainly feel the same way and when I was working with Anne later in the evening I’m sure she would want to know what had happened and I’d show her the marks.

I become aware of a strange sense of enjoyment coming through me as the caning continues but this disappears when Miss Prince is handed a second cane for the final six strokes of my caning and as soon as she taps this across my bottom I realise that it is much thicker and heavier. I try to prepare myself for its impact but can’t do it and give a yell when it crashes down into my bottom with a deep, penetrating thump rather than the sharp sting of the first cane. In many ways it reminded me of the heaviest tawse that had been used at our school. Each of the remaining strokes is followed by the same yell of pain from me and I could feel the tears forming at the edges of my eyes when Miss Prince delivered her final stroke.

‘Girls you will all step forward and have a close look at this bottom. Should any of you pursue an interest in Ken, or any other boy, then this is how your bottom will end up looking’ Miss Prince says and one or two of the more confident girls put their hands down onto my cheeks and this seems to be allowed and certainly tells me how hot and sore my bottom is. It was only after all of the girls and teachers had left that Miss Prince allowed me to stand up and face her.

‘Ken as I said I can see where the temptation for Isabella and some of the other girls has come from but should I receive any further reports that inappropriate behaviour has taken place then you can rest assured that your punishment will increase dramatically’ Miss Prince says before turning and striding out of the room. The second entrance to the kit room opened as soon as Miss Prince had left and it was Anne that stepped into the room.

‘I’ve swapped shifts with Marijka because as soon as I heard what that woman was going to do to you I wanted to hear it happening so I followed the girls down to this room and have been listening outside in the back corridor. It was a horny experience eavesdropping on both of your canings and I’m here to offer my assistance in cooling your bottom down but first I’ve always wanted to get my hands and mouth on your cock because Marijka says it’s very tasty’ Anne says kneeling down in front of me.

The club

When I am meeting a prospective client as part of my job for the first time I always try and do it in as informal a fashion as possible so that I can build a relationship with the client before selling them the benefits of my consultancy services at future meetings. At the initial meetings I try to avoid talking business if at all possible and this proved remarkably easy when I went for a prospective client meeting with Miss Chloe Jacobs. This was to be an evening meeting because it was the most suitable time for Miss Jacobs and I knew that as I operated in a service industry I should fit in with the requirements of the client as opposed to the client having to alter their schedule to fit in with the needs of my company. I had booked a table in my normal restaurant for evening meetings because it was quite a small and private place with a reputation for excellent food and service.

Miss Jacobs, or Chloe, as she insisted I called her from the start of the meeting had a wonderfully relaxed personality and she seemed to have a real ability to open me up and in the end I talked far more than she did. This was actually a very interesting experience for me because it was a complete role reversal as I normally used the exact same process with the clients. After a number of twists and turns the conversation came round to the subject of corporal punishment as a result of a story that had been appearing in the press recently surrounding the sentencing of a British nurse to flogging in Saudi Arabia for alcohol offences. I found it very easy to admit to Chloe that I could see some benefits to this as a strategy for dealing with some crimes and that I had wondered what it would be like to be on the receiving end of such a punishment.

From here Chloe moved the conversation back a stage by asking me ‘did you receive corporal punishment at school?’

‘Yes I did receive corporal punishment at school both in the classroom and on regular visits to the Headmistress. It had always been the tawse that was used in the classroom but whenever I visited the Headmistress I knew I was going to get the cane on the bare bottom’. I openly admitted.

‘How did that make you feel?’ Chloe asked.

‘It was very painful but I was aware of a certain enjoyment in it by the time I was in secondary school and it certainly didn’t stop me from doing things that I knew meant I would be punished in this way if I was caught’.

‘Did you examine the marks afterwards Ken?’ Chloe asked.

‘Yes it was the first thing I did when I got home and whenever I’d been caned my bum was decorated with very vivid stripes’ Chloe was listening avidly and this helped me to carry on. ‘Seeing these stripes was a real turn-on for me and that was probably what I enjoyed most about the punishments and why it didn’t stop me from going back for more’.

‘Have you done anything about these desires since you left school Ken?’

‘I have visited a couple of different professional Mistresses to receive corporal punishment and while they were absolutely excellent sessions there was something missing from them in my mind. I have also been buying a range of films to watch and equipment in the hope of finding someone who will be prepared to use them on me one day’. I answer and notice that Chloe is smiling at this response.

‘You recently purchased a film called ‘Revenge’ which was made by a small club here in Edinburgh although you wouldn’t know that when you bought it. I am the Secretary of the club and we are looking to invest the membership fees from the club and other income for the benefit of all club members. I saw that you had ordered the film and know all about your services as my company has used them in the past so I saw the chance to kill two birds with one stone by having you manage the account but also to see if you would be interested in joining the club’ Chloe said with her eyes looking into mine with a real intensity.

‘Yes I would love to join the club and would be happy to take on the investment account as well. How much is membership of the club?’ I ask.

‘Membership is fifty pounds per month and it is payable after full membership status is granted which follows approval by the Club Secretary and Club President at the end of one of the regular meetings of the club. The next meeting will take place this Thursday evening in Edinburgh and the address will be given to you on that day. Normally the meetings start with something to eat and lots of discussion before people play as little or as much as they want but occasionally ‘formal’ punishment sessions are set up for the enjoyment of all’.

Thursday night was two nights away and I was really looking forward to it. On the Thursday itself I found that I spent all of the day really keyed up with nervousness mixing freely with excitement. During the afternoon Chloe rang me to confirm the address for the evening and to tell me that I should arrive at 7.30pm. I left work at my normal time of 6pm and went home to shower and get changed into a more casual suit for the evening because I knew that it still looked pretty smart. As I was showering I couldn’t help but wonder what state my bum would be in by the end of the night as I expected some form of ‘initiation test’ to take place as Chloe now knew that my interests were in receiving punishment. I was exactly on time having walked the fairly short distance from my flat to the address that Chloe had given me and Chloe herself opened the door at my first knock.

Chloe had on the outfit of a prefect from one of the local schools and she looked utterly believable in it. I was led through to the lounge of the house where a few people were already enjoying a lovely buffet and my natural social skills came to the fore as I was able to talk to everyone and they all made me feel very welcome. I was happy to see that as more people arrived there was an even split between males and females with the total being 8 of each in the end. Chloe stepped forward and introduced me to the group as a new member and indicated that I was also going to be responsible for investing all of the club income. A second lady then stepped forward and introduced herself to me as Suzanne, the Club President.

‘Before we grant you full membership status we have to check that you are suitable and as you have indicated to the Club Secretary that your interests are in receiving punishment then this is done by allowing each person in attendance this evening a chance to punish you’.

This was more or less what I would have expected and I wondered just how it would happen but Suzanne hadn’t finished her explanation.

‘They each get to give you twelve strokes with their favourite punishment implements or two minutes of spanking if that is their preference. Do you wish to accept this test?’ I was asked.

‘Yes Suzanne I do wish to accept the test’ I responded quickly and definitely.

Chloe and Suzanne took a hand each and they led me through to a large back room in the house where two walls were covered with almost every conceivable type of punishment implement and two large vases full of canes were in one corner of the room as well. A large punishment bench was in the centre of the floor and as such it acted as the real focal point for the room. I was led towards this and I knelt on the lower ledge of the horse before my trousers were lowered to my knees. I lowered my torso down along the top of the bench and waited for the fun to begin because I expected this to be hard but good fun at the same time. Those who wanted to spank me went first and Chloe herself led off. She gently lowered my boxer shorts before starting to spank me quite hard with her surprisingly heavy hand. As one hand was spanking me the other was resting in the small of my back but there was no way that I was going to be making any attempt to escape her attention.

Another couple of people chose to spank me and this warmed up the entire surface of my bottom before a couple of paddles were applied to my bottom. The first of these was leather and the second was a heavy wooden affair and as soon as I felt it touching my bottom I knew this was going to be pretty hard to take and I was proved perfectly correct. Despite this I was making no sound during the punishment and was really enjoying it as it felt so good to be in this position with people who were clearly enjoying what they were doing to me. A range of tawses were used next and these increased in weight as each person stepped forward until the fifth person used something I’d never experienced before which was a very heavy rubber tawse. This had a really heavy impact just like the wooden paddle but also seemed to sting more being narrower. Although I didn’t make a sound with this I did screw my eyes closed with each of the twelve strokes and gave a clench of my bottom. Chloe would see my eyes being screwed shut as she was standing at the head of the bench looking at my face. At the end of this she bent down beside me and asked, ‘are you okay?’ ‘Yes I’m brilliant’ I replied and she must have nodded as the next person stepped forward.

It was a range of canes next and again each of these increased in severity and by now I had lost count of how many people were left to punish me but then Suzanne stepped in front of me holding a wonderful looking birch.

‘This will be the final twelve strokes of your test’ she said and as she moved the birch in front of me I craned my neck to give it a kiss a gesture that was not lost on either Chloe or Suzanne who were probably the only people to see it properly.

Suzanne promptly walked behind me and tapped the birch against my bottom before delivering the first of her strokes which I could only describe as blissful agony and made me moan with a combination of pain and pleasure. There was a real feeling to the birching that Suzanne was giving to me and this was what I had been craving for a long time so I was in absolute heaven and didn’t want it to end. When the twelfth stroke had been delivered Suzanne herself stepped forward and asked me, ‘are you okay?’

‘Yes I am brilliant Suzanne. Will you please carry on with the birching’ I said hoping that this was not being too greedy.

‘Yes Ken it would be my pleasure to carry on birching you. You have a great bottom to punish and are taking it absolutely amazingly. I think we have found our next male film star’.

As Suzanne returned to her position behind me I was aware of a range of other punishments were starting to take place around us but all of my attention was taken by the regular and very hard lashes of the birch that were landing on my bottom and the fact that these were taking me further and further into ecstasy. Eventually Suzanne did stop and say to me, ‘I think that is enough for the moment Ken’ and the heat in my bottom was brought home to me when she rested her very cool hands on the toasted flesh of my bum.

‘Do you want some cold cream rubbed in’ Chloe asked but I declined as I wanted to savour the heat and discomfort for a while. Suzanne pulled me to my feet and took me out of this room and back into the lounge where she sat me down, noticing with a smile that I did so quite gingerly, and we started chatting.

‘That was amazing Ken. I don’t think I’ve ever seen anyone take one of the initiations as well as that and I got the feeling that I could have carried on and on punishing you and you wouldn’t have been taken to a point where you said stop. Would you be prepared to take punishment on film because we have not done a film with a male victim for a long time?’

‘Thank you Suzanne. It was brilliant to be on the receiving end because there was a real feeling of enjoyment coming from everyone punishing me and yes I would have loved you to carry on punishing me but it was probably sensible to stop at that point. I would be happy to be filmed during a punishment if you think it would there would be a market for it’.

‘There is certainly a market for it particularly as hard as you would get it and just so you know it would be Chloe and I that would be administering the punishment. Can you give punishment as well?’ Suzanne asked.

‘I don’t know. I’ve never tried but I will certainly give it a go if you want?’ I replied honestly.

Suzanne nodded and she led me back through to the other room where I noticed that almost everyone was engaged in some form of punishment. There was a spare chair in one corner of the room and on the way there Suzanne picked up a solid little wooden paddle which she handed to me. I placed this at my feet as Suzanne lowered herself down over my lap as I started to spank her. I was very tentative to begin with but soon got into the swing of it and was landing some very crisp smacks across Suzanne’s skirt. It was Suzanne herself that used a hand to start to raise her skirt indicating that she wanted to move on to the next level so I took the hint and raised the skirt completely off of her bottom seeing a lovely pair of black panties covering a wonderful bottom. I carried on the spanking over the panties and then picked up the paddle and this was very easy to use and quickly Suzanne was squirming on my lap.

I was finding it a lot easier to punish Suzanne than I would have thought it would be and I was also enjoying it a lot more than I thought I would which probably contributed to the length of paddling that Suzanne received and by the end of it her bottom was a very pretty crimson all over but Suzanne wasn’t quite finished just yet. I watched Suzanne go to one of the vases in the corner of the room and return with a cane which she handed to me.

‘Please give me six strokes with this’ she said before bending herself over and taking hold of the seat. I gave the cane a swing and the swish it made excited me and I tapped it against Suzanne’s bottom lining up where I wanted the stroke to go. My golf and tennis swings then came into their own as I was able to swing the cane with perfect control and accuracy landing it exactly where I wanted to because I had concentrated my eyes on that spot as I had used to do when lining up tackles on the rugby pitch. I didn’t use as long a swing as I could have because this was so new to me and the last thing I wanted to do was to seriously hurt Suzanne but I did raise some lovely stripes on her bottom and they were all distinct so that she could count them when she made her way to a mirror.

‘Are you sure that you’ve never done this before’ Suzanne asked with some shock in her voice.

‘No Suzanne that genuinely was the first time that I have punished anyone but I do play a lot of golf and tennis so I imagine that helps the swing and I also used to play rugby so can concentrate on a spot and hit it’,

‘Yes that probably helps you and it was very good throughout for a first timer. Now can you prove to me that your hands can also be gentle’ Suzanne said as she was handing me a large tub of cooling cream. As I was massaging in the cream I think we both knew that we had found our soul mates and at the end of the evening we agreed to meet for dinner the following night and from here we did start to go out with each other and Chloe in particular was delighted for us and from then on we regularly provided centrepiece events during the Club meetings.

Quiz show

Our Junior Common Room committee are always looking for interesting ways to raise money for charity and they come up with the idea of copying one of the popular game shows from television with all of the winnings going to our designated charity for the year. They seek, and get, permission to run a version of “The Weakest Link” within the college. Sponsorship and prize money would be coming from the brewery that supplies our college bar but this would be topped up by entrance fees and sponsorship money from the participants. As the winner of the game wouldn’t be getting the prize money the brewery was supplying them with a year’s supply of beer or wine and the pay off for them was a lot of free publicity throughout the university and the local community as we’ve gone for a local charity this year. As sponsors the brewery have also asked to supply the quiz mistress and this has been agreed.

I know all about these plans because one of my housemates is on the committee and has been heavily involved in organising the event which is going to take place in our college bar which is a big space. Zoe has been trying to persuade half of our house to put ourselves forward for the quiz but in the end I am the only one that does and I’m not sure who else has put themselves forward as we will not know until shortly before the quiz starts so that no-one can plan a strategy to co-operate. We are introduced to the quiz mistress and our fellow contestants about ten minutes before the quiz starts and I discover that half of my flat from the first year have put themselves forward which will be good fun for us and the audience as we always had a lot of banter. Ms Wilkie is undertaking the role of quiz mistress and the sarcasm she displays very quickly reminds me of one of my former teachers who was never slow in making sarcastic comments about his charges which I’d always loved.

The team had consisted of five women and four men at the start of the game but three of the men were voted off the team in the first three rounds leaving me feeling very isolated and vulnerable as it seemed like the girls were ganging up on the boys. As fate had it the voting in the next round was tied between three of us but I had to make the choice as I was the strongest in the round. It was a straight choice between Susan and Gwen, both of whom had been flatmates of mine in the first year and we are still good friends so I know that I am going to be upsetting one of them. My original choice had been Susan and I decided to stay with this choice. As Susan walked past me she shot me a really evil glare that definitely fitted into the ‘if looks could kill’ category.

Ms Wilkie had been demonstrating her acerbic tongue throughout the quiz but this decision to get rid of Susan who was actually the next strongest after me whereas Gwen had been the weakest was met with particular derision. Whether this decision not to get rid of Gwen had any bearing on her or not I’m not sure but she certainly never voted for me throughout the rest of the quiz and we ended up in the final together playing for a nice sum for the local charity. It was a close final but Gwen won in the end and she went off with her prizes for a minute or two leaving me talking to Ms Wilkie who was in the marketing team for the brewery.

I headed towards the bar to get myself a drink but I didn’t get too far before someone put an arm around my shoulder and directed me into a quiet, dark corner of the room.

‘Sorry’ I said because when I looked round I saw that it was Susan that had directed me in this way and the look on her face told me that she was still furious with me for having voted her off.

‘You are coming with me’ Susan said as she had put the stiletto heels of her boots on my toes and was putting an increasing amount of pressure through them. It appeared that I wasn’t going to be able to placate Susan and in truth I was quite glad of this because I’ve always had a strong preference for very dominant girls although I’ve never really made it too obvious in the college. With her arm still around my shoulder Susan led me out of the bar in the direction of her room on campus as she’d moved back for her final year. Susan locked the outer door of the flat behind her and then she locked the door to her own room as soon as we are inside this. I was looking directly at Susan and saw her pulling out a riding crop from the wardrobe.

‘You are going to pay a heavy price for getting rid of me and not Gwen’ Susan said angrily.

‘Strip’ was Susan’s command and I hesitated for a fraction of a second.

‘If you don’t strip then I will rip your clothes off and it would be a shame to destroy such a nice outfit’ Susan continues. I start to strip all the time watching Susan piling all of her pillows and cushions into the middle of the bed. I am a little scared of where this seems to be leading and Susan can obviously sense this within me.

‘You are right to be scared Ken’ she says as I am now standing naked in front of her. There is another feeling within me and that is arousal but it is buried very deep down inside me going even deeper when Susan shoves me face down over the pillows. Without a second to gather my thoughts the crop is lashing down onto my bottom and I squealed with a mixture of shock and pain.

‘We can’t have that noise alerting the whole college to the thrashing I’m about to give you I’ll have to gag you’ Susan says and I see her reaching into her laundry bag and pulling out a pair of her knickers, ‘there that should keep you a bit quieter’ she continues after shoving them forcefully into my mouth. Knowing what to expect from the crop removed the surprise element but the pain of every stroke remained very real but as the strokes got harder and my bum got hotter I was amazed to find that my cock was beginning to stir as well. Susan dropped the crop onto the bed beside me and returned to her wardrobe returning with a flogger and it was at this point that I realised that I’d been captured by a truly kinky kitten. Susan started to flog my bum but also mixed in some lashes to my shoulders which did absolutely nothing to lessen my arousal. Eventually Susan rolled me over onto my back and she started to flog my chest but more interestingly my very hard cock and balls.

‘So you are a submissive then Ken’ Susan comments and I nod my head in response.

‘You kept that very well hidden from me and I will punish you for it later on but for now you are going to worship your new Mistress’ feet and this will tell me just how much more training you are going to need to become my slave’ Susan concludes.

The cheeky little minx

I have worked for one of the big breweries since I graduated and even though I am only in my mid twenties they have recently given me a village pub to manage and turn round. Running a pub has long been a dream of mine and it is even better in reality although there is no doubt that it is hard work. I grew up in a village where the pub was at the heart of the community and I was trying to bring this about with the pub that I’m managing. One of the most successful parts of that pub had been the food so I’ve re-opened the kitchen in my pub and am doing a wide range of food and getting some good reviews as well. Where I can I’ve employed people who live in the local area so that the staff and the customers know each other and the other thing that I’ve done is to put in good facilities for children of different ages so that families can enjoy the pub together. There is a second bar in the pub with its own room and I use this as a function room and this proves popular with birthday parties and the like.

Lauren, one of the local teenagers, holds her eighteenth birthday party in the pub and as she is one of the youngest in her group almost all of the people at the party are able to drink and it is a somewhat riotous night but great fun. Lauren has been a regular in the pub for the past year and even without a drink she is a very cheeky little minx so it was no surprise when she was worse at her birthday party. Lauren is a very skilled horsewoman and can regularly be seen in the pub in her riding gear looking very sexy it has to be said. One very wet Sunday afternoon a few weeks after Lauren’s birthday party she is sitting in the bar in her jodhpurs and raincoat with her helmet and crop sitting on the bar having been out for a ride in the morning. Because it was such a filthy day the pub was much quieter than normal so I had more time to talk to Lauren and she was flirting outrageously with me while toying with her riding crop in what could have been an absent minded way but I knew that it wasn’t.

‘If you don’t stop this behaviour I will be forced to take you upstairs and put that crop to good use on your bare backside’ I say after half an hour of Lauren’s teasing.

‘What am I doing?’ Lauren asks while trying to put an innocent expression on her face.

‘You are being a cheeky little madam and fine you know it’ I answer.

‘Who, me?’ is the reply said with a pout of her lips, ‘anyway I might enjoy your remedy’ was the concluding statement.

‘I can assure you that you wouldn’t’ I answer even though I am not at all sure that she wouldn’t enjoy it.

‘That sounds like a challenge Ken, you’d better prove that you’re man enough then’ Lauren retorts cheekily.

‘Get up to my flat and wait for me in the lounge. I will be up to deal with you shortly’ I say knowing that one of my staff is due to start in about twenty minutes. Lauren picks up all of her stuff and I let her through the bar before watching her lovely bottom going up the stairs to the flat. By the time I get upstairs Lauren has stripped down to her jodhpurs and boots and is using the tab of the crop to toy with her stiff nipples.

‘Well well what do we have here’ I comment when I see Lauren and she stands up from the sofa with a cheeky grin on her face.

‘You really are a cheeky little madam aren’t you? Sitting half naked in a man’s flat is an interesting choice for someone about to be punished and I guess that as you were playing with your nipples with the crop then you want them cropped as well’ I say and none of this changes the grin on Lauren’s face.

‘Hand me your crop and put your hands behind your head’ I command and Lauren does as she is told without any hesitation. This position means that her luscious breasts are prominent and vulnerable as I demonstrate by flicking the hard tab of the crop across the whole surface which brings a dusky pink colour to the skin. I have left the nipples alone but finally I deliver three firmer smacks of the tab to each nipple. Lauren closes her eyes with the first of them and her hands move from the back of her head for a moment but they don’t come down and get in the way. It was this reaction that made me stop at three on each nipple and not to go any harder because I did want Lauren to enjoy what I was doing to her. Lauren has kept her eyes closed so she doesn’t see me bending down but she feels me giving her left nipple a kiss before rolling my tongue around it and my hand goes down and sits on her crotch. Even through the jodhpurs I can feel the warmth and dampness emanating from Lauren’s pussy and she starts to squirm as my fingers work up and down over her pussy. Lauren’s own hands have come from behind her head and have made their way to my crotch and her touch soon brings about a bulge.

‘Bastard’ was Lauren’s reaction when I suddenly withdrew my touch as I sensed that she was very near her climax.

‘Drop your jodhpurs and bend over to touch your toes. For that outburst you will now get twelve instead of six with the crop on your bottom’ I say with as much sharpness as I can manage in my voice. As Lauren lowers her jodhpurs I see that she has no knickers on.

‘You really are a little tart aren’t you?’ I say.

‘I never ride with knickers on because it’s more comfortable’ Lauren answers.

‘No what you really mean is that it gives you more sexual pleasure’ I respond.

‘Maybe’ is Lauren’s cheeky answer.

When Lauren bends over her bum is full and round with plenty of padding although it’s all muscle to its lovely and firm when I stroke and spank it with my hand. I give her a few dozen smacks with my hand before delivering twelve moderate smacks with the crop.

‘Is that the best you’ve got?’ Lauren says cheekily before bending back over. I give her another twelve but this time they are much sharper and each is accompanied by a little yelp although Lauren stays bent over. Having seen the reaction my mouth and hand had gotten after I’d cropped her breasts I knelt down behind her and buried my face into her bum so that I could kiss and lick her pussy. I didn’t stop this time and after Lauren has climaxed she demands.

‘Fuck me’ and I lead her through to the bedroom for an energetic bout of sex.

‘I told you I would enjoy it’ Lauren says saucily as we are lying in the bed.

‘You are a kinky little madam aren’t you?’ I answer.

‘Yes but lovely with it wouldn’t you agree?’ was the response.

‘Yes I would agree’ I reply. Shortly after this Lauren becomes my girlfriend and she proves herself to be an intoxicating mixture of submissive angel and horny little vixen.