I was running a property management course for prospective landlords at a hotel recently. Sitting in the front row were three very pretty girls, about twenty-five to thirty years-old. They were dressed smartly and looked as if they were related, all with shapely figures and shoulder-length brown hair. During the day I got to talk to them in the coffee breaks and over lunch. It turned out they were sisters, Susan aged twenty-three, Katie, twenty-five and Olivia, the oldest at twenty-nine-years-old. They were hoping to start their own property business so were very interested in what I had to say and, also, the management information packs that I was selling. However, Susan did comment that at £750 the pack was very expensive. I paid no mind to this comment because people often moan about the cost, but this is my living, so I think it’s fair.

At the end of the seminar I went back to my room to change and hit the hotel gym for a quick workout before dinner. When I got to the gym, I was surprised to see the three sisters there as well. Apparently, they were staying on for another couple of nights to do a pamper spa weekend. I wished them well and hoped that they would enjoy the weekend.

I then started out on the running machine, but my eyes were constantly drawn to the girls and their own workouts. All three were in typical gym gear of close fitting Lycra which really left nothing to the imagination. Susan looked the cutest of them all, with a superb bum that I could have ridden all night long. Olivia was the tallest, with Katie having the largest breasts of all three. It certainly made my run more interesting having them to look at. After about twenty minutes I noticed that Susan had left the gym, leaving the other two behind. I thought nothing of it and finished my workout and then headed back to my room.

As I turned the corner in the hotel corridor towards my room I could see my door was ajar. Initially, I thought it was housekeeping cleaning my room, but as I entered the room I saw Susan by my suitcase with a couple of copies of the management information packs from the day's seminar. It was clear she was trying to steal them. I confronted her with the theft and she tried to make up some story about wanting to see if they were worth the money. It was rubbish and I told her so and that I was going to call the police, but she then began to cry and beg me to let her off.

I still wasn’t moved, and then my room door opened again and as I was standing behind the door swing whoever came in couldn’t initially see me. It was Katie and Olivia coming to see what was taking Susan so long, and as the door swung shut they both turned and saw me standing there looking very stern. It quickly dawned on them that their sister had been caught red-handed, and they had just dropped themselves in it as well.

I repeated my intention to call the police and have them all arrested. Katie looked devastated, but Olivia seemed to take this in her stride and asked if there was anything they could do to make me reconsider my decision.

I could see where this was heading, but to be sure I offered them the chance of paying £1,500 for the two stolen copies or taking an unofficial punishment from me. Olivia smiled and said that I should give them the reports for free as it was my word against the three of them and that they would tell the police I had sexually assaulted them and I would be blamed.

Well, this ain’t my first rodeo. I pointed to the laptop in one corner of the room and explained that I’d had a laptop stolen recently and as a precaution, I’d installed an anti-theft tracking package that was motion activated and recorded sound and vision so everything she’d said about blackmailing me and Susan’s theft was all safely recorded and stored in the cloud. The smile fell from her face as she realised they were bang to rights and she’d made it worse with the threat of blackmail. So, I repeated my offer of £1500 or all three take a punishment from me. What choice did they have? Each one in turn agreed to taking my punishment.

They were easy meat as they hadn’t even asked what the punishment was and now it was time to tell them. From my golf bag I produced a thin cane, about thirty-six inches long and just under half an inch thick. Amongst other things I used it to help look for lost golf balls in the rough, but today it would be used to remind three young women the error of their ways.

I flexed it between my hands before making a few practice strokes in the air. The cane made a delightful swishing sound. I told them they would all have to strip naked and bend over the armchair in the room in turn for a caning. Olivia would get nine strokes for trying to blackmail me. Katie would get just six because she’d played a minor role in the affair. Susan, being the youngest would also get six, but because she was the actual thief, in addition to these six strokes I would also fuck her. I moved the armchair into the middle of the room in readiness and then told them to strip.

Susan was the first to start, pulling her top off before pushing down her sweatpants. She was wearing a sports bra and a simple pair of knickers. The other two seeing no option also began to undress. As Katie unclasped her bra I watched her superb breasts tumbled into view. I almost missed seeing Olivia push down a black lacy thong she’d been wearing. Before long all three were standing naked in front of me.

Each had their own charms. Olivia looked toned and sporty, Katie had the classic hourglass figure, while Susan had a look of innocence about her that belied a very submissive nature. I told them all to turn around so I could see who had the best bottom. As I suspected Susan was the best of the lot, I was really looking forward to having some fun with her.

As I was checking them out Olivia called me a pervert and asked if I was enjoying the view. I thought she would be a problem so decided I needed to deal with her first to stop the other two getting out of line. With that in mind, I told Olivia to bend over the armchair and the others to stand against the wall and watch as I caned their eldest sister. I had positioned the chair so that Olivia was facing her sisters so they could see the reaction on her face.

Once everyone was in position I took my place beside Olivia and swished the cane again. This made them all flinch as the realisation of what was about to happen sank in. Then without further ado, I delivered the first crisp stroke right to the centre of Olivia’s upturned bottom. It landed with a satisfying crack and for a moment she was silent before the real sting became apparent and then did she wail! She jumped up with both hands grabbing her bum and turned towards me with a look of total surprise on her face.

I had to smile to myself as one stroke had made her realise this was no joke. I told her to get over the chair again and not to move. Reluctantly Olivia bent over again, but I could see from the way she did it that she was less confident. She managed to take the next two strokes without too much complaining, but number four, which landed slightly lower, had her on her feet again frantically rubbing the area. I had no sympathy, getting her quickly back over again before giving her the next two, which I made harder in the same lower place. She had to learn there was going to be no respite. Her two sisters looked on concerned as their previously strong big sister was reduced to tears by the cane.

She only had three more to come, so I subtly shifted my position so they would land at an angle across the first six. I also made them harder. By the eighth stroke, Olivia’s bottom was criss-crossed with red cane marks. As is traditional I made the last stroke the hardest, whipping it in with full force right in the centre of her bum. It landed with a lovely crack and as the cane bounced away I could see the tramline appear almost immediately. I was pleased to see it had nearly broken the skin, having landed on top of an earlier mark. This was a caning the girl would remember for a very, very long time. It was clear I wasn’t going to get any more backchat from this one as I dismissed her to stand with the others against the wall.

Olivia walked rather carefully to her sisters who embraced her trying to comfort her whilst also seeing close up the state of her welted bottom. I gave them a few moments before calling Katie over to the chair for her turn.

Rather than have her bend right over the back of the chair, I made her stand slightly further away so when she bent over she could just reach the edge of the chair for support. This meant her superb breasts were able to fall freely towards the floor.

I told Katie not to move from that position or else she’d get more strokes added to the six she was due. Then, just as I had with Olivia, I whipped the first one home nice and hard dead centre of her bottom. As I had hoped this made her lurch forward making her breasts swing back and forth.

I waited for her to settle before giving her the second, nice and low, just on the bum-leg crease. This made her breasts wobble again in the most delightful way as well as causing significant discomfort to her behind. I continued the caning in this way spacing the strokes over the whole of her bottom. I gave her sufficient time between each stroke to steady herself before landing the next. This also gave me maximum time to watch her breasts swing about with a mind of their own.

I made number six nice and hard, again at a slight angle, to give the classic five-bar gate pattern. After letting the sting of the last stroke subside I told Katie to get up and join her sisters. There then followed the group hug and inspection of Katie’s bum in comparison to Olivia’s.

Then, without being asked, Susan walked towards me saying that she was ready for her caning. Her demeanour was very contrite and she kept her head down. Her two sisters seemed to be ignoring her completely, being too wrapped up in their own sisterly embrace.

Normally I would have enjoyed the show, but I had Susan to cane and then fuck. I was really going to enjoy this and take my time with her. I began by carefully flicking her nipples with my cane. This had the desired effect, making then stand proud from her now reddened breasts. I then put the cane down and opened the wardrobe. As is typical in hotels, they had the coat hanger with the dry-cleaning bag. What was great about this hanger was the two bulldog-type clips it had which were supposed to allow you to hang trousers from the hem, but they also doubled as a pair of nipple clamps. I carefully attached the clips to Susan’s nipples making her gasp as the clips bit into her sensitive flesh and the weight of the hanger pulled painfully on her nipples.

I then bent her over the chair in the same position as Katie so that her breasts could swing freely, pulled by the improvised clamps. As I took up my caning position I glanced across to see Olivia and Katie still embracing lovingly.

After checking my aim by repeatedly tapping the cane on my target I delivered the first hard stroke. It landed with a loud crack, which, together with a yelp from Susan, finally got the attention of her two sisters. They looked aghast seeing their younger sister bent over submissively with the improvised nipple clamp pulling painfully on her swinging breasts.

Whilst I had their attention I whipped home the second stroke nice and hard on the lower crease of Susan’s bottom. Of course, she gasped at the pain, but her two sisters now seemed more resigned to the fact it was just her turn to be caned. They returned to their own embrace, leaving me free to continue the punishment.

I didn’t want Susan to get used to the cadence of the strokes so I gave her three and four in quick succession. I paused to carefully check the marks and take the opportunity to slip my hand between her legs and gently stroke her pussy. Susan slightly shifted her legs wider apart to give me better access, and it was clear from how damp she was that she liked this better than the caning. Nevertheless, I gave her the last two strokes with full force, leaving vivid red lines on her otherwise perfect bottom. I was about to put the cane down and fuck her when she turned to me and asked for more. I was very surprised, but Susan said she deserved at least as many strokes as Olivia because she was the actual thief.

I was delighted by the request and duly obliged. I carefully spread the extra three strokes across her bottom, but from a slight angle so they made a painful pattern. Using the cane at this angle meant the tip could just bite into the tops of her right leg, creating deep red ends to each stroke.

Finally, the caning was over and I took off the coat hanger-nipple clamp. I was pleased to see it had done its job well, keeping her nipples under constant tension, engorging them, and making them stand proud of her pert breasts. I put her fully over the chair now so her bottom was uppermost because I wanted to take her from behind. She submissively stayed in this position as I quickly dropped my trousers and pants and pulled on a condom.

Carefully shuffling up behind her I slipped the tip of my cock into her. Then, without warning, I took hold of her hips and pulled myself right into her in one go. She let out a surprised moan as I fully impaled her on my hard cock. I can’t claim to have a cock like a porn star, but by taking her so quickly I was able to make the most of things. I settled into a steady rhythm of long hard thrusts, which had Susan whimpering quietly.

I looked across and saw that both Olivia and Katie were watching me fuck their sister. So, I leant forward and grabbing a handful of Susan’s hair, pulling her head up from the seat of the chair so she could see she was being watched.

This seemed to spur her on and she began to enthusiastically push back onto me. In reply, I began to spank her welted bottom between my thrusts. This turned any unmarked flesh a bright red colour and I could feel the heat coming from her well thrashed bottom. This, combined with her pushing back and her sisters watching tipped me over the edge. I felt I was coming for ages as I pumped load after load into the condom. I was lost in the moment, and I’ve no idea if Susan came, and I didn’t care. This was my recompense for three little sneak-thieves trying to steal from me.

Eventually, I pulled out of Susan and turned to face Olivia and Katie. I carefully pulled the full condom off so they could see the load I had shot into their sister. I then dressed myself quickly and picked up the cane again. I used it to point at them each in turn, telling them to get dressed and leave. I also reminded them of the video recording I had of the whole event and their agreement to being caned. I wanted to make sure what happened in this room stayed in this room.

All three of them began to get dressed, carefully pulling up knickers and sweatpants over very sore bottoms. It was funny to see the skimpy thong Olivia wore did nothing to cover the ravaged state of her bum.

Finally, when they were all dressed I ushered them out of my room. Somehow, I doubted they’d stay for their spa weekend now. After all, who’d want to have a massage or relax around the hotel pool in a bikini with a well-caned backside on display?