The Apprentice

"You have completed your apprenticeship, well done."

I was so pleased when my aunt told me, I could not find any words; I could only nod with a silly grin on my face. It had been a long, and sometimes painful, journey to this point, but I was so proud of myself. What a team we would make.

I was sure that under my aunt's mentorship, I would continue my journey of transformation.

Six Months Earlier...

I sat on the train, staring moodily out of the window, my mother's words still ringing in my ears. She had warned me this was my last chance; my aunt had agreed to take me in over the summer. I was to be given a chance to sort myself out and get back on track.

If I were honest, I had badly screwed up, I had been thrown out of university at the end of the Christmas term after failing all my exams. As I had done no work the previous term, it was not surprising. I had then been fired from the local supermarket for arguing with a customer. The last straw for my mother was an official police warning for possession of a small amount of soft drugs. My mother had run out of patience and had called her sister-in-law to ask for help.

I did not know my aunt well, she was always a remote person. She was loving to me, but we did not enjoy a close relationship. I did not even know what she did for a living, but she did live in a nice property in Brighton, so she must have been doing something right. I knew she was in her mid-forties, she always looked fantastic for her age and confidence seemed to shine from her.

In my heart of hearts, I knew I was failing, I was bright when I applied myself. When I tried, I could engage well with people. Although I was never going to win any beauty contests, I was an attractive woman. I needed direction, and then I needed to apply myself. The problem was that I had not yet found anything that appealed to me as a career. Like my mother, I hoped a change of scene would prove an inspiration.

My aunt was waiting for me on the station platform and met me with a big hug and kiss on the cheek. We chatted all the way back to her house in the taxi. I was shown up to the spare room in the attic when we arrived. I was left to unpack and was promised a nice meal that evening at a local restaurant. I felt relaxed and knew that coming here had been a good decision. I was envious in a good way of my aunt, she seemed to have her life sorted out.

The dinner was lovely, with fresh fish that had been caught that morning. The conversation and the wine flowed, and I wondered why I had not spent more time with my aunt. She was interesting; she seemed to have a great life and was great company. While waiting for dessert to arrive, I asked. "What do you do to make a living?"

There was a long pause, and my aunt seemed to struggle with her answer. Then she seemed to reach some sort of decision. "I have two jobs, in the day, I am a website designer, and in the evening, I provide discipline services."

"Sorry, I didn't quite catch that."

She smiled and repeated. "Discipline services."

My mind went into a spin, I tried to think of a logical explanation of what this could mean, but I failed. "What does that mean?"

"I discipline clients for money."

"What, smack them?" I asked.

She smiled and said, "There is a lot more to it than that. I help people fulfil a need they have in their lives, for some, it is discipline, for others, it is a need they have, for others it is motivation. My job is to meet that need. Yes, I do smack some bottoms, more often, I use a tawse or a cane."

I was stunned.

"Many people use my services, and I also enjoy it." Again, there was that smile.

"Does my mother know?" I had the start of a suspicion that this had been arranged.

"Yes, she does."

"Does she approve?"

"Not only does she approve, but I also once disciplined her."

"What you smacked my mother," I asked. I was amazed by this revelation.

"Yes, I caned her, when your father was alive, he was very strict with her. His death left a massive hole in her life. She did a fantastic job of rebuilding and making sure you had a good upbringing, but she did miss the discipline. I helped her fill that gap."

My father died when I was seven years old, he is a very distant memory to me. I never imagined this about my parent's relationship. "Is this why Mother wanted me to stay with you?"

My aunt paused. "Yes, partly. She is worried you are going off the rails. You have so much potential, but you are wasting your opportunities. Dropping out of university and getting caught up with the police. She is terrified for your future and asked if I could help."

"Are you going to smack me?" I could not believe I had just said that.

"I will do nothing against your will. But I do believe you need discipline and direction, and I do think a good smacked bottom, although old-fashioned, is exactly what you need."

Just then, the desserts arrived. I was thankful for the break in the conversation.

While demolishing my Eton mess, my head was trying to digest what I had just been told. Part of me was horrified. How could anyone benefit from being spanked? There was a part of me that knew I had been out of line for some time, and maybe this was what I needed.

My aunt looked at me. "I do not know you well, but from what I understand, you are never going to lead a normal life, you crave the different and unusual. Am I right?"

I nodded, I looked at the lives my friends were leading and almost felt pity for them. I did not want the relationship, career, and buying my own home that were most people's ambitions. I did not know what I wanted, but it was not that.

"I am looking for an apprentice, I have lots of clients, and many others are interested in my services."

Just when I thought this conversation could not get any stranger. Here, I was being offered a job.

"You think I would be interested?"

"I don't know, are you?"

I am a great believer in going with your gut instincts, and I could not deny there was excitement about what we had talked about. But it was so much to take in for me, I still could not get over my aunt caning my mother. "I don't know it is certainly out there as an idea."

"Sleep on it, let's talk in the morning."

We walked home in relative silence, and I was deeply wrapped in my thoughts. I got a brief good night kiss from my aunt and went upstairs to bed. Sleep was hard to come by, and I kept having thoughts of my mother being caned. I then wondered what I would feel like if I were punished. Despite myself, the idea was not horrific in fact, I felt a warm glow down below. Sleep eventually came, but it was certainly not a long, restful night.

As I went down for breakfast, my aunt was returning from a morning run. She looked slim in Lycia, and I could not help but notice her trim figure. As she bent to feed the cat, I gazed at her bottom. My mind was filled with erotic thoughts as I imagined that bottom being punished. I was surprised by my thoughts.

As it was Saturday, we walked into town and did the touristy things. We visited the lanes, browsed the small shops, had ice cream on the pier, we had a lovely time. Once again, I found my aunt easy company and fun to be with.

At lunchtime, we found a nice cocktail bar and sat outside. On our second cocktail, I found the courage to ask. "Could you tell me more about the punishment services you offer?"

"Of course, what do you want to know?"

"I'm not sure everything, I guess."

"Wow, that is not an easy question to answer, but let me try to explain. My clients come for all sorts of different reasons; I probably could not explain to you why some people use my services. They need to submit to some sort of punishment. Sometimes I dress up and act in role-play, so for instance, I may dress as a headmistress and dispense a caning to a naughty young man. Other times I will go for the fetish or dominatrix look, each client is different, and I try to meet their needs."

"Do you have sex with them?"

"No, not in the sense you mean. I will simulate some clients with my fingers. Or use a strap-on to provide relief, but that is as far as it goes. I draw the line at having any sort of intercourse."

She looked into my eyes and asked, "Are you shocked?"

"A little yes if I am honest, intrigued as well as shocked."

"Are you interested in getting involved?"

This was the question I still did not know the answer to. I sat to consider my answer. Before I replied, my aunt said, "I have a client visiting tonight. I think I could ask him if you could watch, would that help you to decide?"

I felt a rush of genuine excitement. "Yes definitely. That would be great."

"Let me check. I will leave you to wander on your own and see you later back at the house."

I spent a very pleasant couple of hours wandering the streets of Brighton. There was a relaxed atmosphere and the feeling that anything goes. It has a different feel from any other British city. All the while, I could not help but wonder what the evening would bring. I arrived back at the house at five o'clock and met my aunt in the kitchen, "it is all set for this evening, you can watch your first punishment. Do you want coffee?"

"Er, yes, please," I could not believe how much this seemed like a normal conversation. We went through to the lounge and watched some rubbish on the TV for an hour or so. Then my aunt said we had better get ready.

I followed her upstairs, and she led me to her bedroom. It was beautifully decorated and perfectly tidy. Everything about her life seemed ordered. "Right, our client, Mr. Evans, is very much a breast man. So, it is best to show a bit of cleavage. As you know, the customer is always right." As she was saying this, she was undressing and soon stood naked before me. I could not help but notice her very trim figure, she had a small stripe of pubic hair just above her pubis. She turned and opened a drawer and soon found a pair of black satin knickers, which she pulled on. This was followed by a pair of black stockings supported by a black suspender belt. She looked ravishing. She quickly dressed in a formal grey skirt and light blue blouse, she left one too many buttons undone on the blouse, and you could not help noticing her cleavage. "That should do the trick." She said she was giving a quick twirl and a smile. "Now, what are you going to wear?"

"I have no idea, what do you think?"

"I don't suppose you packed an old school uniform, did you?"

"No, silly me, I nearly did." We both laughed.

"Do you have any formal skirts or blouses with you?"

"No, not really."

"Let's see if I can find you anything." With this, she opened the wardrobe and began sorting through her clothes. "Strip down to your underwear, and you might want to take your bra off."

I could not believe I was doing this, but I stripped down to my knickers and stood there feeling very self-conscious.

My aunt held out two hangers, one with a sensible skirt and the other with a blouse.

"You are a very attractive woman, you know." This felt like high praise. I quickly dressed, and although this was not a look I would usually go for, I did look very smart.

"You may wish to undo another button," said my aunt with a smile.

I don't have a very large bust, but undoing the next button was very revealing.

We went back downstairs, and went into her office. "If you sit over there, you should get a good view of the action." She left me on my own. As I waited, I looked around the room, which was dominated by an old-fashioned desk, which reminded me of the desk my old headmaster had. On two of the walls were bookcases, and behind the desk was a large mirror, which seemed out of place. Before I could think further about this, the doorbell rang. I was excited to see what would happen next.

I sat and waited. I could hear a muffled conversation outside before the door opened, and a very nervous-looking man entered the room. I would guess he was in his early forties, a little under six feet in height, and seemingly in good physical shape.

"James, this is Miss Penny, who will be watching your punishment this evening."

"Hello, Miss Penny."

I returned the greeting; I was starting to become excited by the events unfolding.

"Let's get on with it then, James you may get undressed."

My aunt said this as if it were the most natural thing in the world. James, if anything, looked more embarrassed, but he did start to unbutton his shirt, then dropped his trousers and underpants. He carefully placed his clothes on the side and stood naked in the centre of the room with his hands covering his private parts.

"Hands on your head."

He did as requested and revealed his erect penis, which was an impressive size.

"As you can see, Miss Penny, even though he is going to be severely punished, this is exciting for him." As my aunt said this, she took hold of his penis and gently masturbated him. James sighed with pleasure.

"Miss Penny, could you bring that chair from the corner and place it here."

My aunt was in command of the situation, and I took the chair she indicated and placed it as required. It looked like a dining room chair with no arms and looked oddly out of place in this study.

My aunt smiled and said, "As men do tend to leak from here," with this, she tugged his penis. "It is necessary to remove my skirt to avoid it getting stained. With this, he reached behind herself and once unzipped, she stepped out of her skirt. She looked stunning in her heels, black stockings, and suspenders.

She sat and patted her lap, "Over you go, let's get this bottom punished."

James obediently got himself into position over my aunt's lap. "Miss Penny, in the middle drawer of the desk, you will find a pair of gloves and a hairbrush. Could you please bring them here." I rushed to do her bidding. As I handed her the items, she added, "Behind the door, you will find a cane, could you please place it on the desk, I will need that shortly."

I took the cane and could not help flexing it between my hands. The tingle of excitement increased.

My aunt placed the brush on James's back and proceeded to put on her gloves, taking her time to make sure they were comfortable. They were black and made of a latex material that extended halfway to her elbow. When she was satisfied, she picked up the brush and rubbed it gently on his bottom.

"I like to warm a bottom up with the hairbrush before a caning, it does make the bottom far more receptive to punishment."

Without a pause, she lifted the brush and brought it down with a firm crack onto his left buttock. The sound of the impact filled the room along with a sob from James. The stroke was repeated on the other buttock again, followed by a sob. She then got into the rhythm of the strokes. With James crying out after each one and his bottom and legs jerking with the impact, this went on for several minutes before the final smack landed. The silence of the room was only broken by the very heavy breathing coming from James. I was getting distinctly wet from what I had witnessed.

After a minute or so, my aunt took control again. "Miss Penny, come and see the effect a hairbrush can have when applied properly." I stood and looked at the bottom, still draped over my aunt's knee; it was red with some very dark patches along with some lighter areas. The lower half of his bottom looked particularly sore.

"Now that he is ready for his caning, James, please present yourself over the desk."

James levered himself upright and gave me a rueful smile as he walked to the desk. He laid himself over with his red bottom sticking out. I realised if he looked up, he could see my aunt behind him, so he could watch his punishment. Now the mirror made sense.

My aunt picked up the cane and swished it through the air. Even though I knew the cane was not meant for me, my buttocks tightened in fear at the sound.

"James, I will give you a choice, I will give you nine strokes of the cane. Or, if you wish, I can remove my blouse so you can see my breasts, but in that case, I will increase that number to twelve. What shall it be?"

"Twelve, please, Mistress," he replied without hesitation. It was the first time I had heard my aunt referred to as Mistress, and another shiver of excitement followed.

"You do say the nicest things." With this, she slowly removed her blouse, and I now understood why she had not worn a bra. She was naked except for her heels, panties, stockings, and suspenders.

James watched in the mirror as she flexed the cane in her hands. I could only imagine what was going through his mind. "Legs further apart, up on your tip toes, and push your bottom out."

James complied, and from my seat, I could see his bottom perfectly placed for the cane to do its worst. Nothing was left to the imagination in this position.

The cane was placed low on his bottom and tapped a couple of times. The silence was broken by the swish and crack of the cane landing, James shook his bottom and called out. I watched his bottom dance around, and a line of pain was drawn over his red bottom.

"Back in position." James complied.

The second stroke produced a similar reaction, but if anything, a louder cry of pain. I watched my aunt's breasts swing with each stroke, and the lines appearing on James's bottom. It was a very erotic scene.

After the eighth stroke, James was struggling to stay in position. Almost conversationally, my aunt asked, "James, would you like Miss Penny to hold your arms in position for you?"

"Oh, yes, please." I was so excited.

"James, I think if you ask nicely, Miss Penny would remove her blouse for you, and then you would be very close to her naked breasts. Sadly, that would add three more strokes to your punishment."

I could not believe what I had just heard, but I was undeniably excited at the prospect.

"Miss Penny, would you please help me take my punishment, and please, Miss Penny, would you allow me to see your naked breasts."

I blushed, "As you asked so nicely, I will allow it this once." I removed my blouse and came around the desk to hold his arms. Once in position, he looked at me longingly. I bent further over, so my erect nipples were very close to his face.

"Let's continue, shall we? Seven strokes to go," she said, raising the cane and bringing it sharply down on his bottom. James jumped and struggled, but he seemed to take comfort in watching me. The remainder of the punishment continued in this manner. After the fifteenth stroke, James looked very sorry for himself, tears were streaming down his face, and I could now only imagine the state of his bottom.

I did not have to imagine for long, "Miss Penny, will you come and inspect James's bottom."

I did as I had been asked and knelt behind James, I ran my fingers along a couple of the red stripes and could feel the heat coming from his bottom. I also noticed his erection was returning. My panties were soaked with excitement.

"We will leave James to dress and retire to the lounge." Still in our state of undress, we went into the lounge, where my aunt poured me a large gin and tonic. When settled, I was asked. "Would you like to be my apprentice?"

"Yes, please."

The End

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