“Right, I have told you before, open your legs. I was not going to punish you there today, but I will now. Three of each thigh. Stay in position.”
She looked very nervous, but she did open her legs for me. I quickly delivered her punishment, and she jumped at each impact. Her thighs bore the red marks of the ruler.
“Now I wish you to stand up and bend over again.” She rushed to obey. “Part your buttocks for me.” This was done with more reluctance. I ran my fingers down the crease between her buttocks. “I may choose to punish you here. I could use my hand, ruler, or hairbrush. When you deserve a thoroughly spanked bottom, you will be punished here.”
“Yes, Mistress.”
My finger now circled her anus. “This is, as you will be learning, extremely sensitive, it can give great pleasure or pain. If I am angry, I will use the ruler to punish this.” I pushed against her anus.
“I will do anything to avoid that.”
“We will see. That is the end of the lesson. Your training will be an experience for you.”
“Yes, Mistress.”
“Before we change for dinner, I will deal with your continued disobedience today. Please pass me your hairbrush.”
“It is upstairs.”
“Fetch it for me.”
She hurried off, and when she returned, I was sitting on the chair she had so recently occupied, and I indicated she should get over my knees. Once in position, I looked down at her pale bottom. I rubbed the brush on each buttock in turn.
“Are you ready?”
“Yes, Mistress.”
The first smack landed, and Lucy jumped on my lap. I quickly landed the second stroke on her other buttock. I then proceeded to punish her whole bottom and the tops of her thighs. She cried out and wriggled throughout. When her bottom was a uniform red colour, I stopped and gently rubbed her bottom. Sniffles were coming from Lucy.
“All over now.”
“Thank you.”
“Open your legs for me.”
She did as I asked, and I gently rubbed her pussy, and my fingers were soon working their magic on her clitoris. Lucy was pushed back onto my hand.
“Training is not all punishment, much of the time, if you obey, it will be pleasurable.”
“Thank you. I want to be good for you.”
“Excellent. After dinner, we will continue your training. We will eat in forty-five minutes, I am going to shower and change. I suggest you do the same. Please wear your new uniform.” I gently slapped her bottom. We both went to get ready for the evening.
As Lucy would be dressed in her school uniform, I was going to dress as I would imagine a strict headmistress looked. I got ready quickly, and made sure everything was ready for our meal when it was delivered. I opened a bottle of wine and waited for Lucy.
After forty-five minutes, she came downstairs, she looked like the classic naughty schoolgirl. Her skirt was too short and showed her stocking tops, her blouse was too tight, and her boobs were trying to escape. She looked exactly as I had imagined.
“Do you like your uniform?” I asked.
“I think I would be expelled from any school in the land.” Lucy laughed. “But it does make you want to play.” She twirled around and showed she had chosen to wear the traditional blue serge knickers.
“Let’s eat,” We sat down and enjoyed a lovely meal, the wine flowed as did the conversation.
I asked, “Why did you persuade your husband to send you for training?”
Lucy thought and replied. “Lots of reasons, as you know, I am bored in my marriage. I enjoy being controlled–not all the time, but sometimes I like someone else to take charge. I do not like being punished; it hurts, but the thought of it and the feelings afterward are worth the pain. It was a risk, but one I wanted to take.”
“Are you pleased you took the chance?”
She smiled, “Yes.”
“Even though I am going to cane you later?”
She gulped, “Yes, even then.”
Lucy asked about why I wanted her in uniform.
“It helps to take you out of yourself; it allows you to imagine a different person. Different uniforms almost create different personas.”
“Do you dress up?”
“Yes, some people I have trained like me to dress differently for them. I have been a riding mistress, I have a headmistress’s black cape. If you are really naughty, I can go the full dominatrix look.”
“Wow, that does sound exciting.”
After dinner, we tidied up.
“I need to get a couple of things from upstairs. I want you to stand in the corner with your hands on your head and await your punishment.”
Lucy walked to the corner, once her hands were in position, her skirt rose even further, it was a delightful sight.
Upstairs, I placed three pillows in the middle of the bed and added a little surprise for later. I then collected my cane and prepared for Lucy’s punishment. In the lounge, I swished the cane several times, and Lucy started to look around.
“Stay in position.”
She quickly obeyed.
“You will receive twelve strokes. I see you chose the bigger knickers, if you thought they would lessen the impact of the cane, you were mistaken. Your panties will be coming down. Bend over in the middle of the room, let’s get this over with.”
Lucy bent over, and what sight to behold. I flipped up her skirt and pulled her knickers down to the top of her stockings.
“You will keep your bottom properly presented throughout.”
“Yes, Mistress.”
I tapped her bottom before delivering the first stroke. Lucy cried out and reached around to protect her bottom.
“Lucy, that stroke does not count. Present yourself properly. We do have all night; it could be a very painful evening for you. Let’s start again.”
I caned her a second time, although with less force. I wanted this to be memorable, but not for all the wrong reasons. This time she stayed in position. I continued her punishment until the seventh stroke. “Lucy, you have six strokes remaining. I wish you to count the remaining strokes and thank me for each. Is that clear?”
“Yes Mistress, thank you, Mistress.”
“Here comes the first.”
I landed my cane once again on her already sore-looking bottom.
“One, thank you.”
I took my time, but eventually we got to. “Five, thank you.”
“Do you know the tradition of the last stroke?”
“No Mistress.”
“It is always the hardest.”
“Please, no, my bottom is so sore.”
I delivered the final stroke, in reality, it was no harder than the previous ones, but it was delivered at the junction of her bottom and thighs.
Lucy cried out loudly but did remember to say. “Six, thank you.”
She started to rise. Until. “Lucy, you should stay in position until permitted to move. Bend over, please.”
She resumed her previous stance, and I gently rubbed her bottom. “Lucy, you are to be sent to bed early, like the naughty girl you are. However you have a choice, you can go to your own room, and I will see you in the morning. Or you can go to my room, and I will rub some cream into your bottom and kiss it all better.”
Without hesitation. “Your room, please, Mistress.”
I smiled. Right off you go. There are some pillows on the bed. Remove your skirt, blouse, and kickers and lay over them and wait for me. She rushed from the room.
I collected another bottle of wine and two glasses and followed Lucy. In the bedroom, she was positioned as requested.
“Open your legs for me.”
She did so immediately.
“Would you like some cold cream on your poor bottom?”
“Yes, please, Mistress, it is very sore.”
I had some cream ready, which I applied to her bottom, and I smoothed it into her punished skin. Soon my fingers found her pussy which was dripping wet.
“Are you enjoying your Mistress’s attention?”
“Oh, yes, it is wonderful.”
“Hold your buttocks open for me there is one more thing I want you to learn.”
More reluctantly, she did as she had been told.
I applied more cream to the newly revealed area and then circled her anus again with my finger.
“This can give you so much pleasure, you just need to relax.”
“I’ll try.”
I circled her opening and teased her. She started to respond and push back on my finger. I gently pushed at her opening, and with little resistance, I found my finger inside her. I continued my teasing while playing with her clit using my other hand.
“Is that nice?”
“Yes, Mistress, naughty but nice.”
“The best things often are.” I withdrew my finger. “We will explore more in the future. Now I have a surprise for you under my skirt, would you like to see it?”
Lucy rolled on her side. “Yes please.”
I stood and slowly undid my skirt and showed her the surprise. I was wearing a strap-on penis, it was bright red, six inches long, with a wide girth. Lucy stared; excitement was written over her face.
“Do you like your surprise?”
“Oh, yes.”
“Unlike the male version, this does not leak or go soft on you.”
“That’s an improvement.”
“I have three different sizes, this one–an eight-inch version and a smaller one for dark deeds.”
“This one looks good to me, the smaller one sounds scary.”
“That is for another time. Do you want to try this one?”
“Oh yes, it is nearly twice the size I am used to.” She said with a smile.
“Roll back onto your tummy.” I knelt behind her and positioned the phallus at the entrance to her pussy. I slowly entered her. I looked down to see my penis embedded in her pussy with her red-striped bottom on show. I was in heaven.
This was the start of a very long night, eventually, we both fell into an exhausted sleep, both of us with sore pussy’s from all the action. One of us with a sore bottom.
Sunday morning was bright and clear. I asked if Lucy wanted to take the horses out for a ride.
report “Oh, yes, it has been a long time, but I love to ride.”
We headed to the stables. I was disappointed to find the tack we would use was tangled and had been left in a mess.
“Peter, the stable lad will find himself over the saddle next week.” I pointed to an old leather saddle that was placed over an A-frame.
“You are going to punish him,” Lucy asked.
“Yes, he does need a regular reminder. It looks like his next one is due. He will be laid over that saddle with my crop applied to his bare bottom.”
Lucy smiled. “That sounds exciting, and that saddle looks comfy.”
“It was ready to be thrown out. Peter has spent hours restoring it. It was his labour of love. So far, he is the only person using it. Although that might change.” I looked at Lucy, and she blushed red.
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