By Monday morning the cane marks had started to fade, although the memories of the weekend were still fresh in my mind. I found myself constantly thinking over the last seventy-two hours. I had been caned for the first time and witnessed the caning of a virtual stranger.
At work on Monday, I resolved to put into practice all that I had discussed with Anita. I felt more confident than at any time since starting in the role. On Wednesday I finally managed to close my first piece of business, my boss was delighted and as soon as I got home, I rushed to tell Anita the news.
She was pleased and invited me over later that evening to celebrate with a glass or two of wine. By eight o’clock I found myself on the sofa with Anita and a large glass of red wine in my hand. I told her all about the new client.
“So, the new regime is working?” Anita queried.
“It looks like it is yes. Thank you for helping me out.”
“We are only just beginning, you are a very smart woman, you just have not tried to reach your potential yet.”
“I am pleased you think so.” I paused. The wine had gone to my head. “The six strokes were worth it.”
“That is only a beginning too. Can you still see the marks?”
“No, they are faded now but I used to check every morning.”
“How did they make you feel?”
“It is strange, I know I deserved the punishment you gave me, but I was also proud of them. Does that make sense?”
“Yes, when I was last caned, I checked my bottom every day until the stripes had gone.”
“When were you last caned?”
“More recently than you may think, but I will say no more for now. I do have something for you though.” With this curious answer, she left the room to return holding a cane. “Now the stripes have faded this will help you remember to be good. Hang it on the back of your bedroom door.”
She handed me the cane.
I took hold of it like I was holding a snake. It was very thin and very flexible and as I knew from experience, very capable of imparting a sting. I am not sure if I was emboldened by the wine but I asked, “Do you enjoy caning people?”
Anita smiled, “You are very nosy tonight. If I am totally honest yes, I do. I enjoy the power it brings; I am not cruel and would never push someone beyond their limits. But I also feel corporal punishment works. Look at the change it has helped to bring for you.”
“Are you a lesbian?” The question had escaped my mouth before I had thought it through. I had always been curious but had not been previously brave enough to ask. The wine effect I suppose.
“You are being direct,” again she smiled, “but a fair question. Let us say I have strong tendencies that way. Can I ask the same question of you?”
I felt myself blush. “I have had boyfriends, but in the first year of university I had a relationship with a girl that ended badly but I loved her very much, it hurt a lot at the time.”
“Interesting,” was all Anita said.
The conversation drifted onto more mundane matters and just after ten o’clock, Anita stood. “I need to get to bed, remember I will see you for your weekly reckoning tomorrow. See you at eight o’clock.” With that, we both retired to our separate bedrooms.
I had another successful day at work on Thursday and my boss told me that he had seen an improvement. I thought the reckoning would go well.
At eight o’clock we both sat at the kitchen table with coffee this time. It was easy to list all the good points of the week. I was then asked, “Is there anything else we should discuss?”
“Well, I forgot to mention a store card last week, that is also on its credit limit.”
“Anything else?”
“No, I think that is it, it has been a really good week.”
“It has been a good week, but I thought you said you would start to get fit. Have you done anything about that?”
“Well, no not yet.”
“I also thought you would remember that you forgot to shave properly. Had you forgotten?”
“I thought you would remember.” I blushed at the memory of having stray hairs around my anus.
“So, you have even more debt, you have not started to get fit, and you forgot to mention something you had been specifically told to remember. Is that right?”
I took a swallow. “Yes.”
Anita looked at me. “Tomorrow you will receive nine strokes of the cane. It will help to maintain your great progress.”
I could not think of what to say. Nine strokes seemed so many.
“Do you agree it would be beneficial?”
“Yes,” I stammered.
“You saw how I was dressed when I punished Peter last week, would you like me to dress in the same way for you?”
I did not expect this question, but a shiver of excitement passed through me at the suggestion.
“Yes, please.”
“Then you should also call me Mistress whilst I am dressed for you. Do you have stockings and suspenders you could wear? They would make you look very sexy.”
“No, I have some at my mother’s house, but I did not bring them here.”
“If I give you some money, would you buy some tomorrow?”
I was being paid to dress for my punishment and the thought excited me.
“Yes, if you want me to.”
“Punishment is a very intimate thing; I feel you should look your best. Choose as if you were going on an important date.” She paused and looked at me. “One other thing, if you deserve any extras, I will be using this strap,” she took a short leather strap from the drawer. “It is called a groove strap.”
“Where is that used?”
“When you are bent over you hold your buttocks apart and this is used to punish the exposed flesh inside your bottom groove.”
My heart pounded in my chest. “However, if you deserve no extras, I will reward you with my tongue.”
I could not believe what had just been said. I felt a surge of both fear and excitement at the same time.
“I will see you tomorrow, do not be late.”
That night I struggled to sleep. Did I want to be seduced by this woman? Did I want this strict regime? Did I want a relationship with her? The answer to all these questions was yes. I finally fell asleep in the small hours, and in the morning the first thing I saw was the cane hanging behind my door, the cane that would be visiting my naked bottom at least nine times tonight. I hoped that the groove strap Anita showed me would not be used, I was really scared of that.
Friday lunchtime found me lingerie shopping, I was not sure what lingerie was best when you were getting your bottom caned, and I did not think I could really ask one of the shop assistants. I finally decided on black, black suspender belt, with a black bra and black stockings. I completed my outfit with black satin panties. They looked very high class. A month ago, I would not have believed I would be shopping for lingerie in advance of a caning, not only that but enjoying doing so.
Later in the bath, I very carefully shaved I did not want extras for stray hairs. When I was sure I was totally smooth I dressed in my little black dress and new lingerie. Looking in the mirror I was pleased with the result. I bent over and looked at my bottom framed by my suspenders and covered in black satin panties, it looked very sexy. I trembled when I imagined what it would look like very soon. I took hold of the cane from behind my door and went to receive my punishment.
Anita was still dressed in her formal clothes she looked like she had just come in from the office.
“I am glad you are on time. Stand here.”
I stood in the middle of the room and Anita walked around me, I was being inspected, and thoroughly inspected at that.
“You look lovely,” I was told. “Now remove your dress and let me see what lingerie you chose.
I took my dress off and stood in the middle of the room again. Once again, I was inspected.
“You have great taste in lingerie, you look stunning.”
I was glowing with this praise. I felt absurdly pleased that I had passed her inspection.
“I have been looking forward to this all day,” Anita said.
I had been both dreading and looking forward to this, dread was currently winning.
“Let’s have you in the corner, whilst I go and change.”
Anita pointed to the far corner, I walked over followed by Anita. “Face the wall, hands-on head.”
I could not believe what I heard. She wanted me to stand like a naughty schoolgirl. But I did as I had been requested. I felt Anita’s hands at the top of my panties, and she pulled them down to the tops of my stockings. “You have a beautiful bottom, it almost seems a shame to punish it, but as you have been naughty punish it I shall. Remain as you are still I return.”
I stood facing the wall with my naked bottom on display and my mind in turmoil.
Although I was nervous, I was starting to feel dampness creep into my pussy, this situation was also exciting, but in a scary way. After a few minutes, I heard the sound of heels coming down the wooden staircase, my waiting was nearly over.
“Turn round,” I was instructed. What a sight greeted my eyes. Again, she was wearing a black latex basque, black gloves, stockings, and suspenders with knee-length black boots. This time however she wore no panties her naked, shaved pussy was on show. She looked stunning and very sexy. “Let us have you mount this chair for your punishment.”
She pointed to a leather armchair, “I want you to face away from the seat with a knee placed on each arm. Then lean forwards and push your bottom right out.”
I mounted the chair as requested.
“Dip your back and push your bottom right back.”
I was in a most lewd position there was nothing hidden. I also found a part of this surrender exciting.
“That is better, I need to inspect if you have shaved properly. She knelt behind me. I could feel her face close to my pussy. Then she ran her fingers over my groove she could not fail to notice my excitement. “You are looking forward to this I see.” Her finger trailed along the crack of my bottom which was fully exposed in this position. She lightly pressed onto my anus. I pushed back. “What a naughty girl you are. Pleasure comes after punishment if you are a good girl. You have shaved properly. Well Done.”
Again, I was pleased with the praise.
“You are definitely good enough to eat, but first you need to be caned. How many strokes did we agree on?”
Even though I know she knew the answer I replied with a slight catch in my voice, “nine strokes.”
“Ask me properly,” Anita had raised her voice.
I was frantic then remembered. “Please Mistress, give me nine strokes of the cane.”
“That is better,” if you forget again, it will be extras. “I will take my time punishing you, I will give you one stroke each minute, you will count and thank me. Please keep still and keep your bottom pushed out for me.”
This was it. I wanted to be brave, but I did not feel at all confident of not letting myself down. I heard the cane being swished behind me and my buttocks tensed. “Keep your bottom relaxed.” I was firmly told. It is very hard keeping your bottom relaxed for the cane.
I felt the cane being laid across my bottom then a couple of gentle taps and then the first stroke arrived. I shouted out, I had forgotten just how much the cane hurts. I struggled to absorb the sting.
“What have you forgotten?”
Again, I was frantic and then said, “One, Thank You, Mistress.”
“That is better.”
I waited for the next stroke, and it was delivered just below the first. I cried out again and shook my bottom trying to relieve the sting.
“Two, Thank you, Mistress.”
After the third stroke. Mistress said, “Take your bra off and get back into position.”
I did as I was asked and once back in position, I pushed my bottom out. My boobs hung down and Anita gently cupped my right breast. “These are beautiful too.” Even though I was suffering I was pleased with the compliment. Anita then teased my nipple which stood erect as a result. “They are so sensitive to my touch. But let us carry on.”
I would have preferred her to carry on playing with my breasts but sadly this was not going to happen. The cane was placed for the fourth stroke, and this was delivered with the usual force. I cried out again and my hand reached behind to soothe myself. Then I remembered and counted the stroke.
I struggled through the next two strokes. Then I heard.
“Reach behind and hold your buttocks open for me.”
I knew I had not managed to keep my dignity and feared I would get extras. I was so scared as I reached behind. I dreaded the groove strap it sounded so painful.
“You deserve at least four extras, and you still have three strokes to go.” Whilst Anita was saying this, she was trailing the groove strap along its intended target. “I know you are at the beginning of your training, but you need to do better.”
“It hurts so much,” I complained.
“It has to hurt to have any effect,” she paused and ran her finger along one of my stripes. “Your bottom looks lovely, just like a naughty bottom should. I am going to be kind. I will not give you the extras you deserve, and I will defer the three strokes owing. On Sunday I have one of my clients visiting for a caning, I will complete your punishment then. If you fail to take that punishment properly you will be getting the groove strap.”
“Thank you,” I could not believe how grateful I was to avoid any further punishment tonight. I then had the thought I would be naked on Sunday in front of a stranger and not only naked but bent over for the cane.
“Go to bed, I will see you tomorrow.”
I was disappointed with myself; I had wanted to be brave and had failed and Mistress had dismissed me. I was hoping she would lavish attention on me but that did not happen. I walked holding my cane to bed and eventually went to sleep on my tummy.
The next morning, Anita visited me and again rubbed cream into my bottom, this time she did focus on my pussy. She teased me with her fingers, if I tried to push against her she withdrew.
“You did not masturbate last night?” I was asked.
“No, I was disappointed in myself. I so wanted to be good during my punishment.”
“You are still early in your training. Do not be too hard on yourself.” This was the second time she had used the word training and I was intrigued by its use. Before I could think much more Anita’s finger finally found my clitoris and teased me. I was already wet from her earlier attentions, but this caused a flood in my pussy. “You are beautiful.” The teasing was short-lived, but I was thrilled with the attention.
“I may need your help tomorrow. Hayley is coming for the cane; she has earned herself twelve strokes. She has never had that many before you may need to help her through her punishment.”
Firstly, I was relieved it was a woman who was to see me punished. “Of course. What can I do?”
“Just be there for her. You might need to help her to keep still during her punishment. If you are interested Hayley does have lesbian tendencies.”
I got a thrill that I was asked to help someone through a caning.
Anita then left me. “I will see you tomorrow Hayley coming over at seven tomorrow evening. Arrive just before.”
The weekend dragged until I had a bath and dressed once again in lingerie for my Sunday evening. I had thought of this as my punishment uniform, previously I had hand-washed my panties as they had been close to my wet pussy on Friday. I took my cane and made my way to Anita’s lounge.
I was greeted with. “Sit there holding the cane on your lap and wait for Hayley.” I sat as requested. It is hard to remain calm when you are holding the cane that will shortly be paying a painful visit to your bottom. I heard a car and saw a taxi pull up outside the house.
A good-looking woman in her early forties stepped out of the car and knocked on the front door. Anita ushered her into the lounge. Hayley’s eyes widened when she saw me sitting there with the cane on my lap.
“Hayley, this is Amanda, she is to be punished tonight as well. She had a six-stroke caning on Friday and has three more strokes to come tonight. She has also agreed to help you through your punishment tonight.”
Hayley said, “Hello. Nice to meet you.” She smiled a very nervous smile.
Before I had a chance to reply Anita said, “Right ladies, strip down to your underwear and face the wall.” She pointed to the opposite wall. “I want your hands on your heads and silence.”
I rushed to comply and saw Hayley do the same. I glanced and saw that Hayley had a large bottom that filled her white panties. I did feel sorry for her imagining what she must be feeling with a twelve-stroke caning ahead of her.
“I will go and change, I expect complete silence whilst I am gone.”
I stood in silence facing the wall I was not even brave enough to look at Hayley. She did the same thing. There was a feeling of high tension in the room. Like on Friday I heard the high heels behind us before I heard Anita say.
“Turn around, panties down, both of you.”
It felt very strange. Here I was naked before a stranger I had met ten minutes previously.
“Hayley, mount the chair and push your bottom out.”
Hayley took up her position. She placed a knee on each arm of the chair and lent forward so her head rested over the back of the chair. She pushed her bottom into the room. I could not believe how exposed Hayley was in this position. I could see everything. Her shaven pussy was visible along with the brown ring of her anus, her bottom was perfectly positioned for the attention of the cane. I could also see that her pussy was glistening with her arousal. I was in the same state.
Anita placed the cane ready for the first stroke, “remember the count and remember to keep your bottom still. I will not have you avoiding the cane.”
“Yes, Mistress.”
I was stood behind Anita and watched in fascination as she drew back the cane and landed the first stroke. The sound seemed to fill the room. Hayley cried out and counted the stroke. A white line briefly appeared across her bottom, but this was soon replaced with a vivid red stripe. I could not take my eyes off the scene before me.
On the third stroke, Hayley nearly jumped up. She was starting to struggle. Anita turned to me and said, “Amanda remove your bra and go around and stand before Hayley’s head. I want you to lean over her back and ensure she does not move. Off you go.”
I did as I had been requested. I let my bra fall to the floor and leant over Hayley’s back and felt my naked breasts pushed into her.
I heard her whisper, “Thank you, that will help,” and I felt a lot better about this.
As I looked up, I could see Anita before me, cane in hand, and I was also close to Hayley’s bottom. I watched the cane drawn back for the fourth stroke and saw its impact just before me. I had a grandstand view and was fascinated. I managed to keep Hayley still and after the sixth stroke, Anita said.
“Right swap positions, Amanda you will receive your three strokes and Hayley will help you.”
I was expecting to be punished later, but the thought of Hayley being so close was a comfort. I mounted the chair and as I settled Hayley lay over my back. The cane delivered its three punishing strokes, and I did manage to keep my position.
“Final six strokes for Hayley, swap positions.”
I thanked her for her help, and I got a weak smile in response. Hayley pushed her bottom out again and I was treated to the wonderful sight of my mistress delivering a severe punishment. Hayley did struggle but eventually, she called out, “Twelve Thank You, Mistress.”
“Back facing the wall both of you.”
We resumed our previous positions, hands-on head facing the wall. Now however two striped bottoms faced the room.
I heard Mistress sit down and felt her eyes watching us both closely, I tried to stand perfectly still.
“Hayley, you need to get dressed your taxi will be here shortly, Amanda stay in position.”
I heard Hayley dressing, and a car pulled into the drive.
“Thank you for my punishment,” Hayley said as she left. A small kiss was exchanged.
When we were alone Anita stood behind me, “you did better this evening. Are you ready for your reward?”
I was so excited by this. “Yes please.”
“Follow me,” she headed towards the main staircase. On the stairs, her bottom was just in front of me. What a wonderful sight. We entered her bedroom. “Lie on the bed.”
I did as instructed and felt Anita push my legs open and then she had her head just in front of my pussy.
“I have wanted to do this for so long,” was the last thing she said before she started to kiss and lick my pussy. It was not long before she found my clitoris and had me quickly on the way to my orgasm. “Come for me darling,” I was told, and I was happy to oblige.
Anita lay next to me, and we cuddled for a few minutes whilst I was coming down from my high. “When I am dressed as your Mistress, I will be in charge in the bedroom, otherwise we will be lovers.”
This was more of a statement than a question, a statement I was happy to agree with.
“Yes, Mistress, I would like that very much.”
“I would like you to worship me, lie on your back.” With this statement, she positioned herself with her thighs on either side of my head and I looked up to see her pussy inches from my face.
“Ready?” I was asked.
“Yes.”
Anita lowered herself onto me and I tasted Mistress for the first time. I was in heaven I could taste and smell her, and she was beautiful. I found her clitoris and concentrated on giving pleasure, I was rewarded with Anita’s pussy pushing down on my face. My nipples were teased whilst I was busy, and I was taken to a new level of pleasure. Eventually, Mistress achieved her peak, and I was pleased I had helped. When she came down, we cuddled further.
“I have two strap-ons I will use with you. A large scarlet one for your pussy and a smaller pink one for your bottom.”
I felt a now-familiar pulse of excitement and fear, I had never had anything in my rear passage.
“That is for another day. Let’s sleep now.”
The End.
