Mary stiffened at his suggestion, but he had put the proposal in such a way she knew she couldn't refuse to take Isabella's punishment, so she nodded silently.

He gave her a small slap on the bottom. "You know the rules Mary, ask me properly."

Isabella whispered in her ear and Mary blushed and then stood back slightly from them and dropped her eyes. She was about to commit herself completely to him.

"I...I need to be punished M...Master," a little fizz of excitement went through her as she addressed him as Master for the first time. "W...W...With the cane Master. I need to be caned."

He put a hand on her cheek. "Then you will be caned, Slave." Her breasts shook as a little tremor went through her at being addressed as Slave.

He took both their hands and led them into the bedroom where he told Isabella to pile the pillows up in the middle. Once she had finished he led Mary forwards and laid her on top of the pillows so her backside was high in the air.

He put the cane just in front of her head and began to caress and squeeze her backside; his fingers teased her pussy but never penetrated, he probed at her anus making wriggle. A caning and a being buggered in the same night, that was pushing it a bit too far. But one day he would use her tightest hole, another education for the good judge.

He got off the bed, picked up the cane and swished it through the air a couple of times. Mary, thinking he was going to strike, closed her eyes and waited for the first strike. But instead he sat down on a chair and said, "Issi, warm this slave up."

Isabella knelt on the bed and began to rub Mary's bottom, her fingers slid easily into her moist tunnel, then she deposited a small kiss either side and began to spank her with rapid fast slaps.

Mary felt the heat in her backside begin to build and her legs opened up wider as Isabella worked the whole area available to her. Every so often she stopped and rubbed at the sore flesh and then began to spank her with renewed vigour.

Mary was giving out little moans of discomfort by the time she finished and her bum felt like to was on fire. She felt someone take her hands in a solid grip and opened her tear filled eyes to see Isabella smiling at her.

Then she felt the cane tapping on her sore bottom and she looked back over her shoulder to see Alan, no, her Master, standing above her with the cane in his hand. Spell bound she watched as he lifted it and then, with as flick of his wrist he delivered the first stroke.

A whole new pain exploded across her backside. She expelled all the air from her lungs with a drawn out, "Arrrrrrghhhhh!"

Now she knew why Isabella was holding her hands so firmly, without her she would have leapt up from the bed and her hands would have gone to rub at the sudden searing pain.

She was just about to say, 'No more', when there was another three taps and the second stroke hit home. Tears ran from her eyes as she tried to say something, but he lined up another stroke and it landed just below the other red tramlines that had appeared on her backside, and then without warning he put another two strokes on her glowing buttocks.

Mary found her voice and wailed. "Oh God that hurts, no more please."

He put his hand on her red hot bottom and squeezed the flesh hard. "I'm not finished yet slave, one more."

"No, no, please Alan, that's enough." Mary gave another wail as he landed a hard sharp smack on her backside.

"Alan? Alan? That's going to cost you another six slave."

"No! No! Please No! You are my Master. I can't take another six Master." Mary's brain was fogged with the stinging throbbing pain he had brought to her.

"Well maybe another three then. You need to be punished don't you Mary?" He continued pulling and squeezing her fleshy backside as he pushed her into the necessary asking for her punishment.

"Noooo, please, I will do whatever you want Master." Mary had slipped into complete submission; she just wanted to please this powerful man.

He inserted three fingers into her wet pussy and then put all three into her anus. "I need an answer slave, three or six, tell me what you need!"

Mary sobbed, "Three Master I n...n...n...need three Master."

Another explosion of pain across her nether regions, "Owwww! Owww!"

Back to three light taps and then, Swish! Five fell across the other strokes making her rear up and her mouth open and a silent scream came out. The last stroke fell on the, as yet, unmarked area where her buttocks met her thighs. Every time she sat down for the next few days she would feel that one as a reminder.

After the last stroke fell Mary went limp on the bed, but then felt her thighs gripped and she was twisted over onto her back. Her legs were lifted up and he pushed his hard tool inside her, making her gasp as his rough pubic hair rubbed up against the last sore tramline.

With her legs on his shoulders he said to Isabella. "Work on her tits girl," and then began to fuck her.

Isabella took both of Mary's breasts in her hands and began to squeeze them while sucking on her hard nipples. Mary gave a squeal as this double assault made her orgasm. The Headmaster began to fuck her with long powerful strokes, making her moan as he banged up against her tortured flesh.

On the second orgasm Mary just burbled as Isabella had stuck her tongue down her throat. As he unloaded inside the crying, moaning, once sophisticated judge she came for the last time. As she reached her peak Isabella pulled painfully on her nipples and she went limp.

He pulled out and her legs dropped to the bed, splayed wide, He pushed Isabella between her legs and she began to lick his come out of Mary.

"Oh no not again," she murmured, but spread her legs even wider to give her fellow slave easier access. Again as she climaxed he made sure she felt more, tingling, stinging pain as he pulled on her nipples with his teeth. Once Isabella had finished she sighed, and closed her eyes.

Isabella came and sat on her Master's lap and rested her head on his shoulder. He slipped a hand between her legs and gently masturbated her. "So, do you think she's a convert, Issi?"

"Oh, oh, oh, Yesssss!" Isabella sighed a she reached a much wanted climax. "I think she is going to be another member of your harem."

"Well I'm spent for the moment so go and make love to her. It's about time she brought you off with her tongue." He popped another blue pill and settled own to watch his two girls at work.

Isabella crawled onto the bed where Mary laid, her eyes closed and regaining here breath. She kissed her all over her face and then worked her way down her body until she reached her pussy. Swinging one leg over her she pulled Mary's legs up and inserted her tongue as far as she could down her wet tunnel.

Mary's eyes opened to find Isabella's dripping pussy hovering just inches above her face. The Headmaster shoved a pillow under her head, bringing her so close she could smell the girl's excitement.

As she felt Isabella locate her clitoris and flick it with her tongue, making a shiver go through her body, the Headmaster said in her ear. "It's time for you to reward your fellow slave with an orgasm Mary."

She put her tongue on the lips of the pussy in front of her and scraped it across the soft lips, tasting Isabella's essence. Hesitatingly she delved inside and was rewarded with finding the hard nub of Issi's clitoris. Mary began to flick it and soon Isabella's body was shaking with an orgasm, followed by her own orgasm washing over her body.

She went to stop but he told her that he would tell her when she was finished and he watched as they brought each other to orgasm two more times before coming up behind Isabella he entered her pussy and his balls hung down over Mary's mouth. Gently she licked at them as he fucked the girl on top of her, Isabella, well trained, continued to lick Mary until her master had finished and then all three lay on the bed, exhausted and soon fell asleep.