Head and Tail - Part 3
By
The Master of Discipline

In Part 2 they explored their sexuality as June Brown teaches James the pleasure of spanking and being spanked. Part 3 takes James into new worlds of pleasure.

By now the meetings of Headmistress June Brown and James had an established routine but this time he arrived for dinner with the 'dessert' promised as an enjoyable but as yet unknown quantity.
James arrived with his head still full of their previous meetings and wondering what was in store this time.
As on previous visits they had their dinner and were drinking coffee in the lounge before anything was said. June looked at James.
"Would you like to go further this time?"
James didn't really understand what she meant but up to now everything had been so pleasurable that he was willing to try anything. She warned him
"This will mean more pain but more pleasure than before. Do you think that you are ready for it?
Again James was unsure what she meant but was prepared to see what happened.
She explained.

"This time James we are going to use the hand, heavy strap and the cane. These will be used stronger than we have before but I promise you that in the end it will be worth it.
She took his silence for assent and said,"Right James, we will start with the hand spanking to warm your bottom so undress and across my knee."
James took off his clothes and lay across her lap where she gave him a good hand-spanking to warm him up. After about thirty she massaged his bum and then continued for another ten minutes until his bottom had a warm tingling glow.
"Now James it's your turn to deal with me." She stood up and slipped her skirt and blouse off so that he saw her superb body hardly covered by the flimsy bra, belt and panties. She draped herself across him and waited for him to start
"Splatttt", "Splatttt"
his firm hand came down and gave both cheeks equal measure. After fifty spanks James slipped her knickers down below her thighs and continued, at the same time massaging her between her legs to ensure that her vagina was warming up nicely. The juices were beginning to make the inside wet and he continued for the next ten minutes until, like James's her buttocks had a rosy hue to them.
Taking the initiative again June said,
"Enough for now James because we are moving upstairs where we can get prepared for the rest of the evening."
She slid off James's lap and the two of them moved up the stairs into her bedroom where she had the other instruments laid out.
"Now James I am going to use the strap first, and then the cane. I will not do anything to you that I do not want you to give me in return. OK!"
James agreed and June told him that she wanted him laid out flat on the bed with a cushion underneath his buttocks. James complied and she took up her position at the side. She raised her arm and brought it down with a firm movement.
"Splat t t t",
James was shocked at the power of the blow as he felt it sink into the cheeks of both of his buttocks. This was more of a thump and his buttocks driven in than the sharp pain of the paddle or hand. It was more intense than anything he had had before but he had no time to think as June continued
"Splat t t t","Splat t t t","Splat t t t",
the blows rained down until he had counted thirty. By now his buttocks were beginning to feel sore but between his legs his errant cock was thickening and straightening out as his sexual urges took over making if difficult for him to adjust his position to a more comforatable one. June took a short rest and then said
"Twenty more".
James was not sure that he had heard right but waited for the blows "Splat t t t","Splat t t t","Splat t t t". She had reached twenty and her arm was still working like a machine,
"Splat t t t","Splat t t t","Splat t t t",
" I am, now going to give you the last ten really hard"
and the strap hit with such force that it raised welts on his buttocks and he cried out
"Ow, those hurt."
"Trust me James",
she answered.
"Now it is your turn. You saw the strength that I used and I want you to hit me just as hard. Do not be gentle."
She took his place on the bed and James, taking a firm grip on the stap, raised it
"Splat t t t", "Splat t t t",
it sliced down making June grunt as her head burrowed into the pillow.
"Splat t t t","Splat t t t","Splat t t t",
he kept going and saw the white ridges that were being formed on her buttocks by the edge of the strap.
"Splat t t t","Splat t t t", "Splat t t t","Splat t t t", "Splat t t t","Splat t t t", "Splat t t t","Splat t t t","Splat t t t",
he now aimed lower, almost across the top of her thighs. Still he continued until twenty strokes. She gasped
"Last ten James and really make me feel them."
"Splat t t t","Splat t t t","Splat t t t", "Splat t t t","Splat t t t", "Splat t t t","Splat t t t", "Splat t t t","Splat t t t", "Splat t t t","Splat t t t",
James brought the strap down with even more effort and counted out the last ten making sure that the final two really hurt.
"Well done James, I didn't think that you had it in you. Feel between my legs the juices are running. Quickly I need that cock. Take me from behind this time." And she bent over the bed so that the lips of her cunt were exposed between her legs. The buttocks were fiery and turning purple and streaked with long lines where the edges of the strap had connected but they looked 'O 'so inviting as James took his cock in his hand and thrust up into the warm interior which was waiting for him.head_and_tail3d.jpg - 6425 Bytes
"Hard now James" she said and he started pumping away listening to the slap slap of his belly on her buttocks as his thrusts pierced her almost to the heart. She moved in time with him fondling his balls and calling out ,
"More, More, Harder"
until finally he felt the moment arrive for both of them. The lips of her vagina started squeezing him with a rhythmical action and he felt his cum welling up as her vagina contracted around his cock squeezing it in a vice and the contractions forcing him to spurt into her in great jets.
James collapsed on her back with the exhilaration and exhaustion of his efforts and June flopped forward onto the bed so that she could leave his softened penis in its nest for a few moments. Meanwhile James's mind was in a whirl. He could not believe such erotic experiences could possibly be happening to him and he wanted the evening to go on for ever.
June eased herself from under him.
"OK James I must visit the bathroom but we have one more experience to go before the day has ended."
James was not sure that he could take any more but was willing to try anything when led by this lovely lady.
When June returned they relaxed in each other's arms just cuddling, kissing and gently playing with each other for a half an hour before June said
"Are you game to try the cane James?"
Remembering his experiences at school James was not sure that he wanted to but, if June was to have the same then he couldn't chicken out.
This time June moved a chair into the middle of the room and told James that she was going to cane him whilst he was bending over it. Because James had not tried this before she would only give him ten strokes. She in her turn would receive twenty.
"Ready James, bend over the chair, legs to the sides of the back legs of the chair and stretch your arms down to hold the bottom bar. Do NOT stand up until I have finished."
James felt great trepidation as he bent over but prepared himself and
"CRA A C C K",
the cane whistled down and took the breath out of him as he felt a searing line across his buttocks
"CRA A C C K","CRA A C C K",
the next two followed and they were just above the first one making the whole area painful. He wanted to shout out as the pain rose. He could feel the weals rising and hardening. He was not sure that he could stand the rest but he could feel that his cock was already beginning to react so waited in position
"CRA A C C K",
four, then five. June adjusted her grip then
"CRA A C C K","CRA A C C K",
the sixth and seventh whistled in. He steeled himself for the rest
"CRA A C C K", "CRA A C C K",
this next one must be the last
"CRA A C C K",
it came down with extra force and he cried out as it burned a line across the previous one. His buttocks now felt as though they were on fire and he could hardly stand up when June said,
"Finished now James, I hope you didn't think I was too hard but you now its your turn. I want you to cane me as hard as you can but before you start I want head_and_tail3f.jpg - 8169 Bytesyou to tie me to the chair so that I cannot move. You will find some cords on the dresser."
June bent herself over the chair with her glorious buttocks standing high over the crossbar of the chair. She stretched her legs to the sides and her arms as far down as they could go redy for James to tie her. Diffidently James tied her up. The white cords anchoring her feet to the legs of the chair were followed by her arms being fastened to the front chair legs and a single cord around her waist held her tight to the back of the chair.
"Right James, listen carefully. I want you to give me TWENTY strokes of the cane. I want you to really cane me hard and even when I cry for you to stop you carry on until the twenty are finished. Is that clear?"
James said that he understood but he was worried about hurting her.
"Don't worry I promise you it will be OK."
James took up his stance on her left side, raised the cane and
"Swish. . .Whack!
The first stroke landed dead centre on June's buttocks and left a livid line across them as it sunk into the flesh.
"Swish. . .Whack!
The second stroke was about three inches below the first and left a second livid line.
"Keep going James you are doing fine"
"Swish. . .Whack!
The third stroke was above the first two and left a line parallel to the others which were now beginning to turn purple.
"Swish. . .Whack! "Swish. . .Whack! "Swish. . .Whack!
The next three lashed in filling in the area which was so far untouched. The whole area was now a livid red streaked with white slashes which were changing colour and swelling as he watched.
James hesitated before he raised the cane again but remembered his instructions
"Swish. . .Whack! "Swish. . .Whack! "Swish. . .Whack! "Swish. . .Whack! "Swish. . .Whack!
The blows continued to stripe June's bottom and now she was beginning to react. She was making small whimpering noises in her throat and her backside was wriggling as if trying to avoid the cane but "Swish. . .Whack! "Swish. . .Whack! "Swish. . .Whack! "Swish. . .Whack!
To James it seemed that June's bottom was covered in bruises and could not take any more but she urged him on.
"Keep going James make these last five really tell.
James rubbed the sweat from his hands and taking careful aim lashed the cane down
"Swish. . .Whack!"
June screamed. James hesitated.
"Swish. . .Whack! "That's enough James! I've had enough"
But James remembered what she had said at the beginning and took a pace back before stepping in to strike
"Swish. .Whack!"
"Owww!"
June cried out for mercy but James finished off with the three hardest strokes that he could deliver while June was screaming in her agony.
"Swish. . .Whack!
"Swish. . Stop for God's sake stop I can't take any more!
"Swish. . .James Please stop I don't want any more! Please!
The final stroke came in diagonally crossinghead_and_tailf.jpg - 3958 Bytes all the previous bruises and leaving her bottom almost raw as June cried and cried.
She lay across the back of the chair sobbing gently until James walked over to her and untied her. She fell into his arms saying
"Thank you James, I needed that. Will you get the cream from the side and soothe my bottom before we make love again."
James reached down the cream and started to massage it into her bottom working it all over the buttocks, between her legs and around her vagina as his fingers soothed the pain of the beating. June relaxed and let his fingers ease the appalling stripes that were now turning a definite purple and were standing out on her swollen bottom. Gradually the erotic sensuality of the soothing hands took over and she in turn slid her hands up and down James's rampant cock. She bent over him and kissed the tip before rolling her tongue around the end and up and down the sides. Her fingers caressed his ball sack and before long she was telling him that she wanted it in her.
"Let me get a pillow to go under my buttocks and then we will fuck."
She rested herself on the cushion and opened her legs wide. He saw the coral lips parted and the mucus of her spend oozing out of the engorged lips of her vagina. He knelt down and smelt her odour before settling on top of her and sliding his roused cock deep inside her.She said
"Now James fuck me as hard as you can and keep going however much I am in pain. I do not want you to stop for at least ten minutes".
She eased his cock until it was comfortable into her warm interior as James started to push.
He moved gingerly at first to avoid hurting her and trying to pace himself so that he would not come too early. As they fucked so his movements pressed her inflamed buttocks into the pillow but she said
"Don't be shy, let me have it all!"
Their motion got quicker and they worked with each other vying to see who could thrust the hardest. Sweat was pouring of their bodies and they were slippy with the effort. James stopped and turned her over the side of the bed to thrust in from behind. June cried out calling
"Don't stop"
and James continued to pound away their bodies slapping together in time with each other. They changed positions again and James withdrew as June said,
"Wait while I put my legs in the air"
as she lifted her legs and allowed him to see the cunt lips framed by her thighs.
James entered and went deeper than ever before as he thrust in and out for what seemed forever with heightened sexual tension in both of them. They panted and sweated towards their climax They both seemed to work faster and harder until with one final lunge he pushed his cock to the top of her womb while she in her sexual release wrapped her legs tightly around his back, arched her back and screamed. It was too much for James who also reached his climax and spurted his seed high into her womb.
Coming down from their high they subsided on the bed relaxing and kissing, their tongues touching and their hands sliding over each other's body before finally falling back exhausted and resting. Once she had gathered herself June left for the bathroom to get herself clean. James just laid back and wondered what their session next week would bring.
He joined June in the bathroom and they showered together. Nothing sexual as they were both exhausted but a pleasant ending to a perfect day.
The fourth and next part of this story will be available shortly