A young woman is caught in a difficult situation. 

By Julie Baker

Author’s note: this is a fictional story but the first part is based on actual events that involved me many years ago. When I first moved to London, aged 19, there was a young lad who worked in the office. He was 16 and not allowed to go out on photo shoots, but he would often question me about relationships. I helped him as best I could but I have often wondered whether I acted in his best interests. Please email me or message me via Twitter if you have a view having read the account below.

My name is Georgina Stanbury but I have always been known as Georgy. I was born in London in March 1993 which means that I am now 25 years old. I am a trainee corporate lawyer working for one of the large law firms in London. I am still single but I’m on a good salary and enjoy a fabulous life. However, it could have worked out very differently for me had I not got away with what I now consider to be, a serious error of judgment 5 years ago. The origins of this situation date back a little bit further in time.

When I was 13 years old my parents sent me away to a top girls’ boarding school in Dorset. I loved it. I made lots of friends for life, I had access to the sea for canoeing and sailing and they pushed me academically so that by the time I left I had a place at Durham University to read law. Anything to do with boats has always been my main passion but I enjoy all outdoor activities including horse riding and hiking. I am a slim but reasonably strong girl so I was good at athletics and was one of the few girls who actually enjoyed cross country running!

I have black hair and olive coloured skin. I’m reasonably tall with long legs, slender waist and small but firm breasts. I take a size ten dress and I was told that I was one of the prettiest girls at my school. However I was also born with a voracious sexual appetite. I love the excitement of a sexual encounter and I’ve had many partners over the years. The trouble is that I’m easily bored in this area and this leads me towards short term relationships and currently I have no desire for a long term partner.

Hopefully this gives you enough background information for you to understand the events that took place in June 2013 at my old school. I must also make clear at this stage that I have changed all names and locations to protect the identities of those involved.

You may have worked out from the dates that I left school in the summer of 2012 after my A Levels and I started at Durham in that autumn. My school for many years has run outdoor courses during the summer holidays to make best use of their outdoor facilities and on-site accommodation. The school is unusual in that it has an equestrian centre as well as the normal sports facilities, plus a fully equipped sailing school with access to safe waters. It attracts a wide variety of groups ranging from school parties to corporate training companies.

In my final year at school I took a course to become a sailing instructor with the idea that I would be able to return during my university summer holidays to work at the sailing centre. This worked perfectly and even now I usually return for a couple of weeks sailing in August. During my first university summer I had just over two months off and I started work at the sailing centre at the end of June. After a few days of planning and settling in, our first group arrived in the first week of July.

It was a group of 40 boys from a large and very famous boarding school located just to the north of London. They were mostly aged 16 and had just completed their GCSEs. They were a joy to work with; high spirited but polite and enthusiastic about the activities on offer. They were there for a fortnight which was great as it gave you time to develop their skills and really get to know them. There was one boy in particular called John, who came from a farming family in Hampshire, who I particularly liked and spent quite a bit of time with.

John was a typical 16 year old boy. He thought about mainly sex and a bit about sport. We fell into the habit of sitting together after supper each evening chatting over a range of subjects but the conversation would always return to the same one topic and it wasn’t sport! He had little access to girls and couldn’t believe his luck that I was both knowledgeable, from his perspective, and willing to discuss these matters. He said that he had a girlfriend back in Hampshire and it was clear that he would love the relationship to be sexual. However he had no idea what to do next to achieve this goal.

I advised him to take it slowly and be guided by what she wanted but I could tell that this wasn’t what he wanted to hear. He was 16 and desperate to find out about the world of lovemaking. Every evening he would bombard me with questions. I helped as best I could, responding truthfully if I knew the answers and making it up if I didn’t. In his eyes I was the expert on all matters sexual. I liked him and he was also very good looking. I was 19 and he was 16. That was a significant gap in terms of maturity at those ages but it was still only three years in my mind.

It was the Wednesday evening of his second week and once again our conversation had turned to sex. He kept on asking me what it was like to have ‘proper’ sex compared to ‘doing it himself’. Although I was prepared to ad lib on most subjects I told him that I really couldn’t help him on that one. I knew how it felt for me but there was no way I could tell him how it was for the boys. He got that but still looked disappointed and frustrated. Then I had an idea.

“You could do it with me if you want.”

John looked shocked and a bit taken aback.

“Pardon, Georgy? What did you say?”

“You could do it with me, John. That’s what I said.” I felt the need to spell it out to him. “Have sex with me, if you want to.”

“Wow! Do you really mean it, Georgy? You and me having sex? That would be brilliant, but you’re teasing me, aren’t you?”

He was leaning forwards in his chair and he had a somewhat desperate expression on his face. I could see that he could hardly believe his good fortune if my offer was serious. I had to think fast of how I could execute my plan.

“I wouldn’t tease you on something like this, John,” I replied. “It’s a genuine offer but you will have to do as I say and follow my rules. No negotiation. First of all, I want to make it clear that we are not in a relationship. We like each other but we don’t love each other. I’m therefore not offering you any kissing or cuddling, only sex.

“You will need to go into town tomorrow and buy a condom. We will need to do it in the little kitchen at the back of the boathouse after tomorrow’s sailing lesson. The lesson finishes at 4.00 pm and you should volunteer to help me put the boats away, so that I know you are still interested, and then go back to your room to get changed. Please come back to the boathouse at precisely 5.00 pm. Not a minute before and not a minute after. Come through to the kitchen and I will be ready for you.

“I will have my normal instructor’s kit on (this consisted of white polo shirt and pleated navy skirt) but I will remove my underwear and sand shoes before you arrive. When you come in I will bend over the end of the dining table, raise the back of my skirt and spread my legs. You can get undressed to whatever extent you want, put on the condom and enter me from the rear. The rest is up to you, but afterwards you should get dressed and go back to school. I’m trusting you to not discuss this with anyone. This is, and must always be, our private secret. Have I made myself clear, John, and do you want to accept?”

“Thanks, Georgy,” John replied in a barely audible voice. “I’d love to accept.”

“OK, John. We have a deal. Now, off to bed and I’ll see you tomorrow.”

At the time I convinced myself that this was a selfless act to help out a young lad I liked, with little or no cost to me. I thought it might give him a bit more confidence for when he was back with his girlfriend. Looking back, though, I realise now that my motives were, in fact, partly or mostly selfish. The theatre of the set up and my control over John were two massive turn-ons for me. Given John’s lack of previous experience, I realised that the actual act itself was likely to be fairly quick and mechanical. However, I had a plan so that I would also enjoy the encounter. I have a gift for achieving quick and easy orgasms and this is why I gave John such precise instructions for when he should arrive at the boathouse.

All went according to plan the next day. The sun shone, it was red hot and we had a great two hour session on the water with about 20 boys. John helped me put away the equipment after 4.00 pm as arranged and then he disappeared back to the boarding house. By half past four, I had finished my duties. I closed the front doors of the boating house and walked back through the storage area and into the old kitchen at the back. I made myself a cup of tea and sat at the dining room table alone with my thoughts. I could feel my heart pounding against my ribs.

The room has probably changed little in the last 50 years. The floor is made up of old oak planks and the walls consist of dark wood panelling with school team sailing photos and honours boards for decoration. The basic cooking area is reasonably modern but the dining table and chairs look as old as the boathouse itself. There are no full windows in this room, only a row of small opening windows high up on the back wall behind the kitchen cupboards. It was stiflingly hot and they were all open that day.

At a quarter to five, I began to get myself ready for John. I took off my sand shoes and then removed my white cotton panties from underneath my skirt, placing them on the table; a flash of white against the dark wood. I had given him a precise time so that I had the opportunity to get myself stimulated to that tipping point when you can stop and remain in control but any more puts you into that world of ecstasy. I was there when John gently knocked to the kitchen door and walked in.

“Hi, John,” I said. “Are you OK and ready for this?”

“Yes, Georgy, all good with me.”

I could see that he was incredibly nervous. He was dressed in a tee shirt, rugby shorts and flip flops. I guessed that this was to facilitate a quick and easy strip off.

“I’ll get myself into position John, then it’s over to you.”

As I went over to the end of the table, I could see John getting himself totally undressed. No half measures here! I turned my back on him, trusting that he knew what to do with the condom, and lowered my upper body onto the hard table surface. I then reached behind with both hands and raised the back of my skirt exposing my bottom. I widened my stance slightly and waited for John to do the rest.

He wasn’t rushing. I sensed he was taking in the view of my naked bottom, but I was resolutely staring straight ahead, avoiding any eye contact. I was aching for him to start and, a few moments later, I felt him slip deep inside me. I caught my breath as I once again felt a move towards that magic moment. He was quite slow and rhythmical in his thrusts and it was me who climaxed first. I’m quite noisy at these times and before I could regain control I was shrieking with joy as my whole body was convulsed in that moment of exquisite pleasure. I was shouting at him to keep going and then I heard him groan as he couldn’t hold back any longer.

For a moment he was lying on top of me and I could feel his hot breath on my neck. Then he was up and dressed in a flash.

“Thank you, Georgy. That was an unbelievable experience. I can’t thank you enough.”

And with that he was gone. I was left lying on the table still buzzing from the thrill of what had just taken place. When I’d calmed down, I stood up and decided that I would make another pot of tea. I put the kettle on and had just placed my bare bottom back onto one of the wooden chairs when the door opened and in walked Mr Phillips, my old head of PE from my school days and now my boss as director of outdoor courses. My eyes shot from him to my panties, which were still at the end of the table, and I knew that my face had turned bright red.

Mr Phillips was probably in his mid-forties at the time, married with two children who had also attended the school whilst I was a pupil. He is a good looking chap who has a natural air of authority that commands respect. I knew him well and liked him.

“So, what’s going on here, Georgy?” He ventured.

“Oh, just tidying up after the days activities,” I offered. “It’s hot in here so I removed some clothing to help me cool down.”

I know it sounds pathetic but what else could I say? It was worth a try and hopefully he would not pay me much attention and get on with the rest of his day.

“Nice try, Georgy, but I have a different version as to what has been going on in here.”

My heart sank.

He went on. “A few minutes ago, I was walking along the narrow path that goes in front of the Equestrian Centre and along the back of this building. The kitchen windows here were open and there was the unmistakable sound of a girl having on orgasm coming from within. I stood on the bins and looked in through the window to see you having intercourse with your young friend, John. John is a school boy in your care. He might be over 16, and therefore legally able to give his consent, but you are in a position of authority and responsibility and, in my opinion, you have abused your position by doing what you have done. What have you got to say for yourself?”

Suddenly the enormity of what I had done struck home. I had taken this young lad’s virginity and had taught him nothing about love and respect. I had done this for my own entertainment and I was now in a position where Mr Phillips could significantly impact my life and possibly finish any legal career that I might want to follow in the future. I looked at the floor and couldn’t find the right words to express how I was feeling.

“I’m so sorry, Mr P. It was a spur of the moment thing that just happened,” I said, not entirely truthfully.

“You put me in a very difficult position, Georgy,” he replied.

I felt very bleak at that moment but suddenly, out of nowhere, I was thrown a life line. Mr Phillips’ own sexual weaknesses came to my rescue.

“I should report you to the Board of Governors so that they can notify the boy’s parents and decide what course of action should be taken with regard to your behaviour. Alternatively, we can deal with this matter here and now if you accept a penalty involving corporal punishment. The choice is yours.”

I could see that my position, whilst still weak, was improving as now I had something to bargain with; access to my body in exchange for his silence. I knew I could trust him and whatever we agreed between us would be stuck to. He was, and is, that type of person. Also, I knew that this was a very irregular arrangement that could jeopardise his position if the wrong people found out. Suddenly I felt a bit more confident.

‘What had you got in mind, Mr P?” I asked.

“Well I haven’t really come equipped for this situation but I suggest a slippering would be in order; 12 strokes on your bottom with your sand shoe might be appropriate.”

I had no previous experience of corporal punishment but that sounded like a lot to me. However, if it was administered over my skirt and panties then it might not be too bad, I reasoned.

“Would I be fully clothed, Mr P?” I asked.

“Not fully clothed, Georgy,” he replied. “You can keep your polo shirt on but you would need to remove your skirt and underwear.”

This confirmed my worst fears but also demonstrated that this process was more to do with his personal satisfaction rather than any attempt to make me behave differently in future.

“Would you consider fewer strokes, Mr P, if I agreed to take this form of punishment?”

“I’m not sure that you are in a strong position to negotiate with me, Georgy,” he shot back.

There was a short pause in the exchange and I could see that he was thinking about his next move.

“I could reduce it to six, but I would be using a riding crop from the Equestrian Centre next door, rather than your sand shoe. And please be warned, I would be using the crop like a traditional cane rather than striking you with the leather flap only. I want you to be clear about what is involved.”

I liked the reduction in the number but I could see that the riding crop might be more painful than my sand shoe and would probably leave marks on my skin for longer. One thing that I had learned over time is that in any negotiation you should look for something of low value to you that you can give your opponent which they might value more highly. I have always been very proud of my body and, under the right circumstances, I have never been reticent about showing it off to others, so letting Mr Philips see me partially naked wasn’t a big deal for me. It was on this basis that I made my decision. I felt as though I had negotiated a decent concession, but I couldn’t risk over playing my hand.

“OK, Mr P, I’ll take six with the riding crop,” I said, looking at him square into his eyes.

“That’s a deal then, Georgy. We’ll do it now and we must both agree that this whole episode including your encounter with John and the punishment agreed between us remains totally confidential between you and me. Have we got a deal?”

“Yes, Mr P, we are in agreement,” I replied.

“OK, I’ll go and get a riding crop from next door and you get yourself ready.”

With that he was gone.

My head was spinning. What an afternoon! My undies were still resting on the table but I decided to completely remove my skirt to make the whole process easier. With this done I then perched on the end of the table facing the door waiting for Mr Phillips to return. He wasn’t long. When he came back in, he was carrying a riding crop which, on first impressions, was a little longer than I expected. The sight of a semi-naked nineteen year old did not appear to faze him in any way. He spoke to me as if this situation was completely normal.

“Thanks for getting yourself prepared, Georgy. Shall we get on with it?”

“Can I first have a look at the riding crop before you use it on me, Mr P?” I replied.

Without saying anything, he handed the crop to me. My heart sank. This looked like a truly terrifying piece of equipment. It had a moulded black plastic handle which fitted snugly in the user’s hand, and a long slender shaft which, judging by its flexibility, was probably made of carbon fibre or some sort of similar material. It was tightly encased in a thin, shiny layer of dark grey rubber and finished with a small black leather flap at the end. This bit seemed to be the most innocuous part of the overall setup but Mr Phillips had already warned me that he would not be using the crop in this way. I was in for a caning with the long shaft on my bare bottom, and suddenly the enormity of what was about to happen to me struck home.

It was too late, though, for any change of plan. I placed the crop onto the table and, without being asked, turned my back towards Mr Phillips. My polo shirt barely came down to my hips and I knew that I was giving him his first look at my naked bottom.

“Thank you, Georgy,” said Mr Phillips. “Please now bend over the end of the table with your arms above your head so that I can give you your punishment.”

The irony of this did not escape me. 20 minutes ago I was in a very similar position to have sex with John and now I was again over the table with a bare bottom, but this time to receive a caning. Quite a difference! A minor change was that I didn’t have my skirt on and also I kept my legs firmly clasped together this time. This preserved my modesty a bit but I also felt that my bottom was more compact and would cope with the cane strokes better. My soft breasts were squashed onto the hard surface of the table and I reached forward with my arms so that they cradled my head.

I felt the crop gently tapping on my bottom a few times and then it came to rest against my skin for a few moments. I feared for what was about to happen. I felt very vulnerable and was acutely aware that I did not have control at that moment over what was happening to my own body. I thought about my soft and smooth skinned bottom that I had granted John access to a short time before. That was my choice. That was the case 20 minutes ago with John, but now, with Mr Phillips, I was not making the decisions.

Time stood still as I waited for him to make the next move.  I was conscious that my bottom was utterly defenceless and I knew it was perfectly positioned and presented to receive the cane when he was ready. Mr Phillips was in no rush though. Eventually he spoke.

“Are you ready, Georgy?”

“Yes sir,” I replied.

Nothing could have prepared me for that first stroke. I heard the crop whistle through the air and then it landed with full force into my bottom. The explosion of pain was, and still is, indescribable. I let out a loud yelp as I bolted upright. My hands instinctively went behind me to massage my painful skin and protect myself from any further blows. That crop was every bit as bad as I thought it would be when I first held it in my hands a few moments before.

“Christ, Mr P,” I said. “You’ll have to go easy on me. This is my first time!”

Mr Phillips looked unmoved. “You have five more strokes to come, Georgy, and from now onwards I will repeat any strokes that are followed by you not staying in position. Is that clear?”

“Yes, sorry sir. It took me by surprise,” I replied, and once more I bent over the edge of the table.

The same routine was followed a further five times. The caning was much slower than I expected, with each cane stroke standing on its own ‘merits’. I could sense that he was placing them in different areas of my bottom and one arrived just as the effect of the previous one was starting to ease off. I was crying after a couple of the strokes and the only way that I could cope with the pain was to shriek out after each one. I couldn’t believe how difficult it was to manage myself through to the end.

“That’s it, Georgy. Your punishment is complete,” I heard Mr Phillips say. “You can put your skirt and knickers back on and go back to the house. I suggest you talk to John to make sure that he is OK, and please be a lot more careful in future. You are a lovely girl but you made an error of judgment today that could have had serious consequences for you in the long run. Hopefully, it’s a lesson learned for you. I’ll lock up and see you tomorrow as normal.”

By the end of this little speech I was back on my feet, although tears were still streaming down my face. I carefully pulled up my panties over my sore and throbbing bottom before refastening my skirt and putting on my shoes. I was out of there as fast as humanly possible. The sea shore was deserted and I went for a short walk up and down the front to recover my composure. I then went back to the house and straight to my room.

I took my skirt and panties off again and inspected the damage to my poor bottom. There was a general reddish glow to my skin, but the stand-out features were my six livid, red cane marks. I had these for over a week and they were perfectly spaced on my small bottom from just above the top of my legs to just below my back. The bruising took almost two weeks to totally disappear. There was no doubt I’d taken a thorough thrashing.

John was due to go home the next day and I made sure that we had a brief chat before he went. Maybe he’ll view this episode differently in a few years time but it was clear on that day that he was thrilled with the experience and incredibly grateful to me for presenting him with the opportunity. I have never seen or heard from him since that last day, so in my mind I’m as comfortable as I can be that there was no lasting damage inflicted on him. He seemed like a confident, able boy who would take what he could out of the events in the boathouse and move on.

For me it was a massive lesson in life. Bad decisions might turn out alright but the chances are that they won’t. I got lucky with both John and Mr Phillips that day, but it might not have worked out that way. Since then I have been a lot more careful and now make a conscious effort to think through all possible scenarios and consequences when it comes to any major decisions or judgments. Ultimately I got a painful lesson from Mr Phillips, but it’s one that I now value very highly.

The End

© Julie Baker 2019

Julie welcomes contact from her readers. Email at: julie.baker_cane@mail.com   or Julie’s Twitter address is: @JulieBaker_cane