Head and Tail - Part 1
By
The Master of Discipline

June Brown was in her early thirties and had been the headmistress of the local high school for three years when her husband died. No great death. He was killed in a car accident when hit by a drunken driver but, for June, it was as though the bottom of her world had fallen out. They had been a very loving couple in every sense and they had explored the limits of sensuality in their experiences together.
This was what June found so hard. She could put up with the loneliness when she arrived home from school and cooked dinner, marked books or watched television but it was the nights which seemed so long and absence of sex and the other erotic experiences which hurt so much. She knew that she had to fill this void but it would have to be done with extreme caution and thought as to who the person should be. She did not want to get involved with any married men - these would eventually tell their wives the guilty secret and she would lose not only her reputation but her job as well. The macho singles in the town were also out, as these would just consider her another 'scalp on their belt' - and boast of it. No, she needed somebody who was available for her to speak to cautiously without arousing any suspicion.

It was a Friday afternoon when the perfect chance appeared. James Fasconi was sent to her for punishment for hitting a girl. before he arrived she looked up his file and found that throughout his school life he had been a loner who rebelled against authority with great frequency. His home life was bad with a drunken father and mother who had left home. The boy was now virtually a recluse. At the end of school James arrived at her door and was shown in by her secretary. She remembered that he was a handsome boy with permanent sullen expression on his face.
"Well James, back to see me again. What was the problem this time?"
James stared at the floor and said nothing.
"Come on James I want a reason?"
He said, "She called me a wimp because I would not take her to the dance." Mrs Brown said,"I am afraid that that is no reason for hitting the girl and you will have to be caned. Have you anything to say before I deal with you?"
He shook his head.
"Very well then let us get this over with. Trousers down, and your underpants and then over the back of the chair. I will give you six hard strokes for this behaviour."
James undid his belt, stepped out of his trousers and lowered his underpants. He then bent over the chair with his bum cheeks standing proud from his body. Mrs Brown lifted the shirt tail, whipped the cane through the air two or three times and then lined up.
"CRAAAK K! ! !" the first stroke landed across the centre of the buttocks and James grunted. "CRAAAK K! ! !","CRAAAK K! ! !",the second and third followed in quick succession raising reddened weals on his buttocks. Mrs Brown then took the cane back and "CRAAAK K! ! !" the fourth made him squirm as it landed between the first two making the whole area smart. "CRAAAK K! ! !", "CRAAAK K! ! !". The final two again came in quick succession and while James was getting his breath back Mrs Brown told him to stand up and get dressed.
"What will you do when you get home, when you give your father the note about the caning?"
James looked at her and said quietly, "I shall not be able to give him the note."
"Why?"
"Because he was sent abroad for two months on business."
"Does this mean that you are on your own? she queried.
He nodded.
She thought for a moment. "What will you do with yourself?"
"Oh I will find something."
She took a deep breath. James would you like to come to my house and have some supper. I normally eat on my own but there is always enough for two."
He stammered you "But.. you've . just caned me."
She explained."That was punishing you IN school for a misdemeanour. It has nothing to do with inviting you to dinner."
He looked surprised but nodded his head.
"Right, you know where I live I will expect you there at seven thirty."
When she arrived home June gave a lot of thought to how she would dress and act. She must not frighten him off by appearing to devour him but she must get him to agree to all that she intended. After putting the dinner on to cook he had a long bath sinking into the perfumed water and dreamed of what might happen. As she dried herself her fingers sought the petals of her vagina. God she needed. It was now more than a year since her husband's death and only her fingers and a vibrator had consoled her since then. She decided to put on a white lace bra, panties a suspender belt and black stockings. She would wear a knee length dress which could easily ride up her thighs. When she was dressed she looked, and thought, that she appeared like the school mistress inviting the star pupil to dinner on top BUT underneath ..............!
The doorbell rang and James was standing there looking tidy for a boy living on his own.
"I hope you were expecting me?" he said diffidently.
"Come in James, dinner is nearly ready. Put you coat on the chair and then go into the lounge."
James went into the lounge and found that there were places set for two at the table. Mrs Brown brought in the dinners and they spent the next forty five minutes in desultory conversation as they ate. Mrs Brown discovered that James was an only child. he did not mix with his peers preferring to be alone. His father had been sent to prison for thirty day was a habitual drunkard and they found it very difficult to communicate. James was also bright and had a good mind.
After they had finished Mrs Brown said "We will just put the plates in the kitchen and then have our coffee in here."
She sat down in one armchair and suggested he took the other as she was sure that his bottom was still sore from the punishment that afternoon. James sat and she continued,
"Would you like me to put some ointment on your bottom to soothe it?
James looked shocked but nodded unable to speak.
Mrs Brown stood up and went to a large container on the side which she took to the settee.
"Come here James, take your trousers and pants down and lie across my legs."
As he arrived she hitched her dress up so that as he laid down he could just see the stocking tops with the white thigh above. He then felt the soothing hands and coldness of the cream as she gently applied it to his buttocks. What he had not bargained on was the effect that it was having on him. He moved restlessly as his cock started to stiffen between her legs. He tried to adjust it to avoid touching her but the more he did so the stiffer it became and the more the dress rode up off her legs until he could feel the cool flesh above the stockings.
Mrs Brown said, "Don't worry James. I am sure that we can make you more comfortable. I am just gently going to spank you as I massage your bottom. This will not hurt but help to relax you."head_and_tail1.jpg - 6737 Bytes
James blurted out, "I am sorry but you know what is happening."
"Of course", she replied, "There is nothing to be ashamed or embarrassed about.It is quite natural. Why don't you take the rest of your clothes off while I get more comfortable."
James stood up trying to cover his cock which was standing out like a flagpole. He took off his shirt and shoes and socks until he stood there naked except for his underpants. These tented out as his rigid cock stretched them. Mrs Brown meanwhile had stood up and stepped out of her dress so that he could see her superb figure in its white lingerie. The lacy brassiere which cupped her firm breasts, the flimsy pants which hardly covered the black bush between her legs and certainly did not in any way conceal the superb cheeks of her arse. The suspender belt around her waist held up two black stockings which whose tops seemed almost to slide into her crutch.
He looked goggle eyed.
"Do you like what you see James"? she enquired.
"You're ......beautiful Miss!" he exclaimed.
You needn't call me Miss here James, June will do. Now tell me what do you know about ladies?"
"Nothing Miss .. er.. June. I don't have a girlfriend, I can't seem to get on with the girls at school".
"Let's start from the beginning James. What would you like to do?"
He thought for am moment and then said, "Can I feel you all?
"Of course. Shall I take my clothes off or would you like to help me?
James eagerly, "Can I help"?
She turned with her back to him and said over her shoulder, "Brassiere first, there are two hooks which hold it".
James, hands trembling, felt the back of the brassiere fumbling with the clasps until it fell away and the beautiful breasts stood there proud and free on their own. He looked in awe as she gently caressed them lifting them up and massaging them.
"Touch them James they will not hurt you".
His hands moved to her breasts touching each one in turn. He moved his hands over the silky flesh and his fingers stroked the nipples which became engorged at his touch. June's breathing became heavier at his touch and her feelings stronger as memories of earlier times raced through her mind

"Take the nipples in your mouth and kiss them."
James did so all the while stroking her body his hands never still as he explored the wonders before him. His hands began to roam further down until they reached the waist of her panties and the suspender belt. First he wriggled one finger under the elastic top gradually sliding down until he pulled up short as he touched the black hair which was just below.
"Just a moment James I think that you should take these off first don't you? Why don't you remove the suspenders and stockings first. Undo the suspenders and slide that and the stockings down my legs. That's right. Now wait a moment and you will see what you will see."
James watched as she slid her knickers below her thighs and knelthead_and_tail3.jpg - 12587 Bytes in the armchair looking over her shoulder at him. Now slide the panties off and then the suspender belt. There now you can see everything.
"How do I look?"
James stood struck dumb he had never seen anything so beautiful in his whole life. A naked woman, a beautiful naked woman posing just for him. She stood stood up and posed before him with her hands at her sides exulting in his admiration. A beautiful woman she had long legs which seemed to go on for ever before ending in the nest of black hair at her groin. Her buttocks were full and were ripe for fondling, Her stomach was flat and her breasts stood proud from her body, while on her face was a gentle smile as she saw James's reactions.
She gently eased off his underpants and caressed his cock which was standing erect from his body.
There was a pause
"Well my dear, I am waiting what would you like to do next?"
James said,"Can we go up to your bedroom so that I can see everything properly?"
"Off course. Just follow me", and she led him on an erotic walk up the stairs with the cheeks of her arse bouncing just in front of his face as he followed her. They entered the bedroom where the curtains were drawn and a soft light already glowed. June took him by the hand and led him to the bed. "Now I am yours to do with whatever you wish!"
She lay down on her back stretched out on the bed.head_and_taila.jpg - 6430 Bytes James sat back before he started exploring with his eyes and fingers. His fingers whispered across her body as his hands seemed likes snakes, everywhere at once. She luxuriated in the feel of his fingers exploring her most private parts and his gentle touch all over her body. He kissed her on the mouth and she gently parted her lips sliding her tongue into his mouth. Then his hands caressed her breasts before sliding down to nestle in her pubic hair. He seemed unsure what to do now and June put her hand down and guided his fingers into her as she parted her legs. His fingers began a voyage of exploration up into the humid depths. First one finger and then two as she she spread her legs wider made hersalf available to his eager fingers. He was beginning to arouse her to fever pitch now and she took his cock into her hand gently massaging it. James shuddered with pleasure but he took his fingers out of her to slide down and down and see what magic was between her legs
"Wait James we can get more comfotable than this and I can deal with your cock. Turn round so that we are head to tail - it is called 'sixty nine position' then while you explore me I can play with your cock."
James turned round and started to explore her vagina with his fingers again. He gazed into the warm wet interior with the glazed covering of her spend. As he opened her up he smelt that musky smell which only the aroused woman offers. He burrowed deeper putting his tongue in and pushing it up. He began to wriggle it around and as he was doing so he felt warmness on the sensitive top of his cock as June took it into her mouth and began to suck. She sucked and tongued it as he continued to tongue her opening the petals as he explored the central area. All the time he was looking she was writhing and telling him to keep exploring.
"Put your tongue on that knob at the end of my cunt and move it up and down."
As he experimented and he began to inspect the area his tongue flicked over her clitoris and she almost screamed with the sensations that were coursing through her. The area was getting wetter by the second and she was on the edge of a massive orgasm, the first for more than a year. She was pushing herself hard against his cock with her tongue sucking away.
She drew back and urgently said
"Now James quickly put this lovely cock inside me and fuck me."
He turned over on top of her and while her hand guided him his cock nudged its way up through the hairy bush into the soaking vagina until it was buried up to the hilt. He started to thrust into her and and she wrapped her legs around him so that he was squeezed in the vice of her thighs. Soon as she thrust back their movements became more and more urgent but all too quickly he spasmed, spurted his seed into her and collapsed on top of her gasping with pleasure while his cock sunk to its flaccid state and slid out from her body.
He was very apologetic.
"I am sorry I couldn't hold on any longer."
"Don't worry dear the first time is always like this for everybody. Give it a few minutes to recover and you will be ready for anything. Now I must just go to the bathroom for a minute and then we will try again. I have ways of making you stand again for me."
She slid off the bed and proudly walked naked out of the bedroom as James laid back exhausted. Even now he could not believe this had ever started and would continue. Would she let him visit her again? All these questions ran through his mind in the few minutes she was away. Then she walked back into the room and he knew that he had to have this lovely woman again and again. It would be their secret.
June said, "Now James there are ways that help to stimulate both of us and we shall start now. I shall spank you and then you will spank me. You will be surprised the effect that this has. Lay face down on the bed across my thighs and I will give you a good hand-spanking." She sat against the head of the bed and James stretched himself face down across her legs. He then felt her hand strike his right buttock with slight force. Then the left buttock and June continued to strike the buttocks gently but firmly so that his buttocks stung and gradually warmed up .Between strokes she stroked her other hand across them working from side to side and down between his legs tickling his balls and pubic hair so that he felt his cock beginning to rise again. Once it was firm June told him to do the same to her as he spanked her.
She knelt with her head towards the top of the bed and her glorious buttocks raised before him. head_and_tail4.jpg - 4326 BytesThe buttocks offered a magnificent target for his hand. For a moment he hesitated lifted his hand and brought it down very gently on the right buttock.
"A little harder James, then the other buttock and all the time stroke my bottom and between my legs."
James continued for several minutes until he felt her becoming restless and then he said
"Are you ready for another fuck?"
"I need some more spanking first. Now spank me harder."
James slapped the bottom twenty times more with greater force.
"Right James now I am more than ready! But I want to be on top this time.Lay back and leave everything to me."
James lay back on the bed and June raised herself above with one leg either side of his body. She bent over first of all taking his balls and cock into her mouth to wet and stimulate it. She then turned herself round to face him and squatted down guiding his cock so that her cunt slid down on to it. He felt the wartmth of the vagina as he slid in and waited for her to move. She rested there for a minute and then started to move.
"Don't you do anything", she said,"leave it all to me".
James watched as she moved up and down with her breasts rising and falling and looked in awe as his cock slid in and out of the vagina. This lady was all his and the delicious sensations which were washing over him were going to get better he knew. All the time he felt he was getting ready to explode as she speeded up and then slowed down before saying:
"Now James, thrust up into me as I come down".
He started to push up into her and very soon a warm glow suffused his body and he felt his cum beginning to rise again. He thrust harder and faster and as he thrust she called out.
"I'm ready".
And with one last squeeze of his balls with her hand they both came with a massive burst his cum pouring out into her while she cried out in ecstasy.
They fell into each other's arms with June exclaiming
"God I needed that.",
She hugged James.
He was speechless. This was something he would remember all his life and he was sure that this was only the first of many if he kept his head.
They lay together for what seemed an eternity before June said that they must move as James must return home. As they dressed she warned him that he must say nothing of what had happened for both their sakes and she was looking forward to the chance of developing their relationship further in the future.
She let James out of the back door and as he walked home he thought of the luck he had had with that caning this afternoon and what other excitement he and Mrs Brown would have. She meanwhile went to bed relaxed and thinking about the future.
She had her own 'toy boy' to play with. What times they would have as she introduced him to the spanking games she and her husband had so enjoyed.(

To find out read Part Two of this story)