SexStory2 » Nanny Jane

Behind the iron railings the large private garden used exclusively by the residents of Wellington Square was awash with colour, immaculately mown lawns bordered flower beds containing all sort of exotic flowers.  The gardens were overlooked on three sides of the square by imposing late Victorian town houses, from the first floor bedroom of one of these houses Mrs. Frost a plump middle-age housekeeper glanced down into the gardens.   The sight that greeted her was at first glance not unusual, a nanny pushing a pram, a second look and she could see it was the strikingly pretty, but stern faced young lady who was nanny to the baby at No 3.   The housekeeper frowned; the girl was too pretty by half in her opinion, the dress of her crisp blue uniform was not only too tight showing off the girls spectacularly curvaceous figure, but far too short displaying rather too much shapely nylon covered legs.  As the housekeeper mused over the nanny she suddenly froze unable for a moment to believe what she was seeing, the older boy from No 3, now in his mid teens,  was also walking with the nanny, he had been hidden by a tree when she had first looked, but now she could see him clearly.  Shock soon turned to amusement as she observed the lad was dressed in a ridiculous outfit; tall and good looking the boy was wearing a childish sailor suit, in fact the whole outfit was seemingly put together to ridicule the boy, from the short trousers that fitted him like a glove, to the silly sailor hat perched on his head he looked absurd!  As the nanny pushed the pram nearer Mrs. Frost could now see that in her right hand she held black leather leashed the other end which was tied around the lads left wrist.  Shaking her head she looked away, wondering what the boys step-mother was thinking of dressing him like that, or for that matter letting him be treated in such a way.

Two houses away from Mrs. Frost someone else was observing the group in the park with interest. Through the lace curtains of No.8 a tall thin angular lady licked her dry lips; she was hardly able to keep her eyes of young Master Brown in his sailor suit.  Number 8 Wellington Square was the home of Miss Emily Mason and also where her small very private and extremely strict school was located.  Miss Mason a forthright spinster in her 40s was not one of the most popular residents of the square, with a hard narrow face, round spectacles and her brown hair tied tightly in a bun at the back of her neck, she struck terror into the hearts of her pupils. She usually tutored one boy boarder at a time, the boys step-mother or guardian would send a difficult or sissy boy for a six or some times eight month stay, Miss Masons blend of cold baths, hard bare bottom canings and regular purges always broke the lad.  The last boy, a good looking well built lad had suffered greatly, Miss Mason had thoroughly enjoyed breaking him, his going away present had been a caning so severe that he would not sit for several weeks. Now Miss Mason was without a boy, she had observed Simon Brown on several occasions, or more correctly his pert girlish bum cheeks, it was her fervent wish  that she be given a free hand in dealing with young Simon, he could expect  frequent special treatment behind the locked door of her study . Suddenly she made a decision she put on her coat and leaving her house strolled across to the small private garden, to her relief the nanny had decided to take a second walk around the garden.  Approaching the young woman with her charges Miss Mason smiled and purred…

“What a lovely morning for a walk”

Then making out that shed only just notice the boy she exclaimed.

“Why Simon I didnt notice you there…you look quite sweet dressed like that…and what have you got tied to your wrist?”

The nanny grinned as the boy blushed deep red.

The boy stared at the ground and Miss Mason was sure she saw the glint of tears in the lads eyes as he hung his head.  The nanny giggled and in a soft well modulated voice spoke for the first time.

“I told Simon that he looked adorable dressed in his little suit, although it could do with being a bit tighter around his bum..”

Miss Mason observed how the thin cotton hugged the boys buttocks and wondered if the girl was joking, the girls face started to turn pink as she was obviously regretting what she had said.

“Er..what I meant was that…..I was only joking”

Miss Mason very much doubted that, and smiled. It had given her an insight into this misss mind.  Trying to move on the girl blurted out.

“Simons step-mother insisted he wear a leash so he didnt wander off, although he keeps pulling and wont do as hes told”

Miss Mason smiled then quipped.

“Perhaps it needs to be attached to a rather more tender part of his anatomy; I find this usually works with my boys.  Then if he still pulls perhaps a bare bottom smacking over your knee as soon as you get home would cure the problem”

Both Simon and the nanny blushed yet again, although Miss Mason did notice the girl was rather bight eyed and after meeting her eyes rather breathlessly murmured.

“Thats what Mrs. Brown suggested…”

Glancing down at Simon she continued in a firmer voice.

“I suspect that is the traditional sort of nursery discipline your mother had a mind Simon”.

Miss Mason smiled to the young woman.

“Perhaps you would like to come in and have a cup of tea”

Jane glanced at her watch and murmured.

“Mrs. Brown is shortly off to America for 6 months taking young Emma with her, I will however, be free later then perhaps I can look over your establishment I heard all about it. Maybe you can then recommend a suitable cane as Mrs. Brown has asked me to introduce a much hasher disciplinary regime for Simon, a smacking over my knee is alright for minor offences but if hes really naughty I want something that leaves him unable to sit for a few days. Miss Mason looked thoughtful and murmured.

“Indeed my dear…I shall look forward to seeing you later”

Jane smiled as she watch the older woman walk away,   she had for several days tried to get Miss Masons attention, now she had succeed beyond her expectations.

It was barely an hour after Mrs. Brown had left No.3 Wellington Square with her new baby, on route to Southampton to catch the boat to America, than Nanny Hawkins and a very unhappy Simon were making their way to along the square to Miss Masons establishment. Although Jane had lived only a short time at Wellington Square she had head much about the Governess at No.8. Stories were legend amongst the maids about the indignities she made her boys suffer, rather than sympathize with the young men the girls seemed to think their treatment not only justified but quite amusing!

Although intrigued at what went on behind the door of No.8 Jane was also surprisingly nervous, however, glancing at Simon she could see she wasnt anything like as nervous as the boy, who knew maybe he had cause to be, certainly in the back of Janes mind was an idea that maybe a short stay with Miss Mason might do the boy good, his step-mother had certainly given her carte blanc to deal with the lad in any way she saw fit. As Jane knocked on the door of No.8 these thoughts were in her mind, the door was quickly opened and to her surprise Jane found herself faced not by Miss Mason, but a tall, handsome well built middle-age woman dressed in a nurses uniform.  Unsmiling the womans eyes quickly left Janes face and alighted on Simon, a look almost of excitement crossed the womans face, hard faced with her brown hair tied behind her head in a bun the woman she seemed a frightening epitome of a strict Governess with swishing cane.   Jane coughed and hurriedly explained that Miss Mason had invited her to visit, the womans attitude changed and her face broke into a smile, showing even white teeth she replied in a heavy Scottish brogue.

“I see…I thought you were bringing the wee lad for training. Im Nurse Fraser and I help Miss Mason run this establishment”

The disappointment could be heard in the womans voice as she stood back to allow the couple to enter the hallway.    The hallway was cold and gloomy, dark painted walls gave the impression of a hospital or some similar institution, leading the way to a doorway Nurse Fraser stopped Simon and pointed to a corner of the hallway.

“You wait there laddie and Ill not have a sound from you…or else”

As Jane turned to watch Simon push his nose in a corner she was surprised to see Nurse Fraser squeeze one of the boys buttock cheeks none too gently,   then she whispered in his ear.   This had the immediate effect of Simon putting his hands on his head and pushing out his bottom most provocatively, Jane smiled. She had to admit that the ultra tight short trousers the boy was wearing did make his bum cheeks look very smackable. Seeing Jane smile Nurse Fraser quipped.

“Thats the position new lads find themselves, only they are bare arsed and waiting for their first taste of the Mistresses cane…..then up to bed and I introduce them to the leather...”

Jane nodded,   and turned back to the door, from behind her she heard a sharp smack and Miss Fraser in a loud whisper proclaim.

“I told you to keep it out lad………youre a disobedient boy. You need to feel cane and leather long, hard and often. Id keep you on your toes boy”

As Jane entered what turned out to be Miss Masons study she wondered how Simon would fare in the hallway. Miss Mason rose from her desk and greeted her.

“I heard Miss Mason scolding your boy, like me shes very frustrated at not having a boy in residence. When we eventually get one he can expect a scorching welcome.”

As Jane looked around the huge wood paneled room Miss Mason made her way to a glass fronted display case situated by the window, looking back at Jane she murmured.

“You mentioned you wanted a cane for your charge?”

Jane nodded, and opening the case Miss Mason extracted three fearsome looking canes, one of which she handed to the younger woman.

“This cane I think you will find most suitable, effective on the bare and will also bite through the thickest trousers leaving quite a nasty stripe”

Jane gave a nervous laugh.

“I guess that is if you dont want to be bothered to take a boys trousers down for a caning”

Miss Mason looked surprised.

“Oh no…my boys are kept bare bottomed…”

Jane blushed. Seeing the confusion the Governess laughed.

“They wear short, and I mean short kilts.  In your case with lady guests and female staff you will want to cane the boy in front of them but not offend them, thats what I mean”

Picking up the long and heavy cane Jane asked.

“Is this the lightest one you have?”

Miss Mason frowned.

“My dear the boy is what 16 or 17, hes got to feel the rod or its not effective”

Smiling Jane sighed.

“Yes, you are right I will borrow this cane if I might, until I purchase a selection of my own”

From outside the door the women could hear a periodic slap, Jane was sure it sounded like a palm on bare skin but couldnt be sure.   Miss Mason now seemed keen to show Jane the rest of the house, on coming back into the hallway Simon was still in position with Miss Mason standing beside him but she noticed that he was quietly sobbing.  Like the hallway the rest of the house seemed dark and dreary, Jane shivered as they made there way up uncarpeted stairs. On the top floor was a  tiny attic box room used as a bedroom for the boys Jane noticed that on the narrow iron bed was an orange rubber sheet, seeing the young womans gaze the Governess explained.

“Thats if they wet the bed saves us changing the sheet, they still get a good hard leathering straight away from Nurse Fraser and a caning later from me.   Most boys cant control their bladders,   so they start the day with a sore rump”

Jane could well imagine being locked in this room for the night would make you lose control of your bladder.  The small window was not only barred but whitewashed from outside so nothing could be seen from it, a small battered wardrobe was the only piece of furniture in the room, opening up the top drawer Miss Mason pulled out a small leather tube made of hard leather and handed it to Jane, after inspecting it and the small brass padlock and key which hung from a leather strap.  Mystified she looked at Miss Mason, who chuckled.

“Thats a penis restraint……….no Governess or Nanny in charge of a boy should be without one.  Thats a spare so please take it.  I only use one for night time of when Im taking a boy out, other I insist he controls himself, Nurse Fraser and I regularly check him and if his little chap is misbehaving then it gets a hard smacking from my ruler”

Jane grinned, then Miss Mason looked earnestly at her.

“Jane..I can call you Jane cant I, now regarding the boy Simon, I would be very happy to take the boy off your hands for a while so you can have a rest. He obviously needs very severe treatment to control his bad behaviour”

Jane gave a smile and allowed herself to be shown the special discipline features of the house, the walled yard, punishment room with its caning horse and lastly the schoolroom. This was very traditional with a nice display of canes and straps…………..

As Jane strutted from Miss Masons house, with the click of her high heeled stilettos on the pavement, she felt a new confidence.  A week earlier she wouldnt have dared wear such a revealing outfit, but now she was proud to display her womanly attributes and didnt care who knew it. She grinned at the thought of poor Simon trailing behind her still dressed in his sailor suit looking very dejected, unable to keep his eyes off the long, pliable school cane she gripped in her right hand. He knew that when they got home she had promised him a sharp caning, and she was looking forward administering to it. Although she made no effort to hide the cane from the prying eyes of neighbours she also didnt deliberately display it.  Outside No 3 she noticed to her dismay Sir Charles Hodge a good friend of her mistress alighting from a taxi, a very good looking playboy in his early 20s he was rumored to be incredibly rich.  Jane found the young man extremely attractive and usually found herself tongue tied in his presence , however, on sight of the cane carried in Janes hand the young man seemed badly flustered, licking his lips he seemed unable to take his eyes off the rod.  Without thinking Jane turned to Simon handed him the cane she was carrying and curtly snapped at him.

“Go up to your bedroom, hang this cane on the hook behind the door, and remove your shorts and underpants. I will be up to deal with your shortly”

Dismayed at what she had said, with the obvious implication that Simon was to receive a caning on his bare buttocks, Jane turned to face Sir Charles.  Incredibly the young man seemed even more nervous than before and his face was scarlet.  Jane was curious at the mans behaviour and certainly wanted to know more, the sight of the cane added to hearing that Simon was to be beaten had obviously unnerved him.  As he stood there mute Jane purred.

“Im afraid Mrs. Brown is away Sir Charles but you are welcome to come it…”

The man unexpectedly blushed again and mumbled.

“Oh please you dont have to call me Sir Charles….”

Feeling that she was quickly getting the measure of the young man Jane quipped.

“Perhaps I should call you Hodge…or even boy?”

This caused the young man to stutter.

“Y..yes maybe”

Elated that she had guessed right Jane quickly added in a sharper tone.

“And you will address me as Miss Hawkins or Maam, but only when you are spoken to”

Sir Charles now unable to meet Janes stare whispered.

“You know dont you?”

Jane just sniffed, turned on her heel and walked into the house. Opening the drawing room door she strolled in, seating herself in a large leather armchair she crossed her long shapely legs seemingly oblivious to the fact that the short black skirt rode up her thighs exposing not only her stocking tops and suspenders, but the tiny vee of her tight black knickers. Sir Charles followed her into the room and slumped into an easy chair.  In an icy voice Jane snapped.

“I cant remember giving you permission to sit boy!”

Ashen faced the young man leapt to his feet, pointing to a spot in the centre Jane hissed.

“Stand there where I can see you, and stand up straight”

Beginning to enjoy her power Jane scowled at Sir Charles, he nervously coughed and said.

“Miss Frost has obviously told you that I was a pupil of hers…..”

In fact Jane was amazed at this revelation;   although she was only 20 she had thought Sir Charles was much older.   She suspected that the boy was still in awe of Miss Frost, and was perhaps fearful of being sent but for a refresher.   Jane waited and the young man continued.

“….I would not want Miss Frost to learn about my attitude towards you…”

Unsure if this was a game he was playing Jane decided to call his bluff, glaring at him she snapped.

“Well Hodge if leering at my legs is any indication of your manners, I would think a word with Miss Frost would indeed be in order”

Unexpectedly the young man gave a deep sob. Jane trying not to show her excitement licked her lips then purred almost cat like.

“Very well I will deal with the matter myself, and no mention needs to be made to Miss Frost”

A relieved look cross Sir Charles face although this turned to worry as Jane reached for a small bell on a side table, after ringing the bell they waited a few seconds before the door opened and Anna one of the maids appeared.  In her early 20s tall, well built and leggy the girls brief tight fitting black and white maids uniform showed off her figure spectacularly.  Surprised that she had been summoned by the nanny she started, her pretty face framed by curly blonde locks was even more surprised to see Sir Charles standing in the middle of the room. Jane smiled at the girl.

“Anna dear, would you please go up to master Simons room, on the hook behind his bedroom door you will find a cane…”

The girl frowned so Jane continued.

“……a yellow school cane with a crooked handle…..I have use for it here”

As Jane finished the conversation she glared at Sir Charles, this was not lost on the maid who gave the nanny a knowing look.  With a click of heels the maid closed the door and could be heard tapping up the stairs. Jane glanced at Sir Charles and said in a matter of fact way.

“Get yourself ready boy….”

The young man looking shocked didnt move for a split second, then stuttered a single word


Jane trying to look stern and at the same time not laugh quipped.

“Yes, the maid will see your bare bottom ready to be beaten, if you are not ready by the time she returns she will also observe you being caned”

As the horror of the situation struck the young man he started to rip his trousers off, these were followed by his underpants. The nanny pointed a finger at the chaise lounge.

“Kneel on there and push your bottom up nice and tight for me”

As Sir Charles made his way across the room trying to cover his genitals, there was a knock on the door and Anna the maid entered carry the cane, Jane smiled and took the rod from her. The girl stifled a laugh at the sight of the young man who was now kneeling on the chaise lounge with his bare buttocks high in the air.  Glancing at the young man Jane pointedly said to the maid.

“Please wait outside the room Anna; if I need you I will call you”

Obviously disappointed the maid left the room with a last lingering look at the bare male rump.  Jane stride over to the young man who was visibly shaking, gently running her palm over the tight milk white bottom she whispered.

“You are going to behave arent you boy, Im not going to have to call the maid to help restrain you?”

A muffled voice replied.

“No miss”

After wiping her damp palm down her dress Jane gripped the cane and measured it across the shaking male rump, exactly as Miss Frost had demonstrated earlier. Then raising the rod high in the air she brought it down with a fearful swish across the centre of his buttock cheeks. As the hard rattan smacked against the bare skin leaving an ugly red stripe, Jane grinned in the knowledge that Anna the maid outside the door couldnt fail to hear the thrashing.  The boy frantically clenched and unclench his buttock cheeks trying to lesson the sting, with mock anger Jane gave his bare rump a hard open handed smack. Raising her voice so that Anna could hear her Jane scolded the boy.

“Dont you dare clench your bottom cheeks boy; I know this isnt your first caning so you will get that cut again”

The second stroke of the cane Jane applied much harder wrapping the rod around his tender thighs,  as the cane cut into the soft skin the boy bellowed like hed been badly hurt.   For a moment she thought he was going to clutch his sore bottom but at the last moment he controlled himself. Sighing Jane hissed.

“If you dare cover your bottom you will receive an extra six cuts and three cuts across the palm of each hand”

She next delivered three hard stokes of the cane with her full strength, as the cane lashed down badly marking the smooth white skin of Sir Charles bum cheeks Jane almost felt sorry for the man. He was now whimpering and his buttocks cheeks were doing an obscene dance as the cane decorated his rump.  Originally Jane had decided to administer a dozen cuts but as he was obviously feeling the caning she decided to finish him off. The last cut sliced into the back of his thighs leaving a bleeding red raw weal, Sir Charles sobbed uncontrollably and Jane was satisfied.  Going to the door she found Anna bright eyed and grinning handing her the cane Jane whispered.

“Please return the cane to master Simons room, he can go the bed now, I will deal with him in the morning. He will wait for me standing by his bed with his hands on his head”

The maid curtsied and clenching the cane went upstairs.

Turning to Sir Charles who had not moved Jane spoke in a soft tone.

“I hope you now know Im not a lady to be trifled with. Dont redress yet go to the corner and put your nose to the wall and your hands on your head”

To Janes annoyance Sir Charles whispered.

“Please Maam can I leave now….”

To hear such impertinence spurred Jane on  to carry her plan through, smacking each of his now well caned striped buttock cheeks hard with her palm she snapped.

“No you may not leave, you will come with me as I have use for you”

Taking his ear spitefully with her thumb and forefinger she led him out of the drawing room and along a corridor to her room, once there she turned to face him.

“Strip boy”

Jane noticed that his bottom lip was quivering and he seemed in a sweat, it suddenly dawned on her that because of his playboy image she had assumed that he was sexually experienced. However, if he had been in the hands of Governesses such as Miss Frost most of his life the opportunities for sexual liaisons would have been very limited indeed.

As Jane slipped off her bra and let her heavy breasts swing free she was pleased to see that Sir Charles was now naked and awaiting her, pointing to the bed she murmured.

“On your back lad, now you can please me”

As the young man lay on the bed Jane noticed his penis thickening, no sooner than he was on the bed she straddled him; impaling herself on his rigid cock she rode it until she was completely spent. Feeling sore and exhausted Jane flopped down on the bed beside him completely spent.

Early next morning Jane was awake early, looking at the sleeping young man beside her she knew she wanted to keep him, she wasnt worried if she was his lover or his mistresses but have him she would. Hurriedly dressing she glanced at her watch, to her dismay it was already 9.0.clock, leaving her bedroom she bumped into Anna the maid.  Slightly breathless Jane explained quickly.

“I have to take Simon along to Miss Frost shortly, in 10 minutes go into my bedroom and clean the room as normal, Sir Charles in still in bed but tell him that I have given you instruction to clean and make the bed. There is no need for you to leave the room while he dresses; I have left a little present for him.”

As she walked away Jane smiled, the little present was something supplied for Simon by Miss Frost, however, now the boy was going to stay with the lady the item might as well be put to good use on Sir Charles.  On reaching Simons bedroom Jane was pleased to find the boy awaiting for her in his night gown with his hands on his head, however, she was less pleased with a distinctive smell which reached her nostrils. Pulling back the bed covers she quickly found a damp patch on the bottom sheet, without a word she snatched the cane from its hook on the back of the door, then gripping a handful of hair on Simons head she forced his head down towards the fouled sheet.  Forcing him to kneel on the bed with his nose pressed against the damp sheet had ideally presented his bare bottom for the cane; Jane noted with interest his bottom still bore red finger prints courtesy of Nurse Frasers smacking. While she gripped the lad so he couldnt move Jane whipped the cane across Simons bottom six times leaving six parallel raised red cane stripes.  The boy on his release howled and frantically rubbed his now stinging rear end; however, Jane was not finished with him yet. Pointing to the sheet she hissed.

“You will take this sheet downstairs to Mrs. Searle the housekeeper; apologize for what you have done, explain that I have punished you and show her your bottom.  Before you go take off that night gown, perhaps a little embarrassment will reinforce the punishment.”

As the full horror of what he was being told to do struck Simon the boy began to cry, however, he didnt protest as he was very aware that Jane had yet to return the cane to its hook. Seemingly as an afterthought, but in actual fact Jane wanted to find out how effective the caning had been to cower the boy, she added.

“Also ask Anna to give you a bath……tell her to please use the hard bristled bath brush. Any misbehavior on your part then she has my permission to use the back on your bottom.  Dont forget to tell her this as I will be checking with her.”

The boy looked crestfallen but didnt protest, Jane smiled and was beginning to find her new responsibilities extremely exciting.   Poor Simon was soon going to find out that a lot worse things would happen to a naughty boy at Miss Frosts.

It had been a few short hours since Simons step-mother had gone to America taking his baby step-sister with her, since then his life had had gone from bad to worse.  It was supposedly because of his childish behaviour that hes been put in charge of Nanny Hawkins,   but he knew that the real reason was that his step-mother had always hated him, once his father had gone off with one of the maids the woman had made his life hell. Just before shed gone to America his step-mother had moved him into a tiny box bedroom, shed also told him that in future he would be in the charge of Nanny Hawkins, and nanny had been told introduce a strict disciplinary regime.

Now completely naked and his bottom stinging from the vivid cane stripes Simon made his way down to the housekeepers room, holding the damp sheets in front of him he was relieved to find that she was on her own, on his arrival she looked up and raised her eyebrows.  Shaking like a leaf Simon managed to blurt out.

“Nanny Hawkins has told me to bring this sheet I urinated on to you Mrs.Searle, and to say she has punished me and to show you my bottom”

Blushing crimson Simon quickly turned and pushed his bare bottom out for Mrs.Searles inspection,  as he turned back to face her she grabbed the sheet with one hand and gave him a hard slap across his face with the other.

“And thats from me you dirty little brat, if I had my way youd wash the sheet as well. Now get out of my sight before I lose my temper and take a belt to you backside”.

Shocked at his treatment Simon scurried out of the room rubbing his stinging cheek and almost ran up the stairs crying with shame, it seemed that new of the new regime had filtered through to the staff. He now waited naked in his room for Anna to come with a clean sheet and make his bed, she was not long in arriving having obviously heard about his accident.  Of the entire maids he hated being seen like this by her, she was by far the most attractive and he found her sexy.  As she entered the room he could tell straight away by her curt manner that he was not going too treated leniently.   Glaring at the boy she scowled.

“Youve made extra work for me you brat, Im glad Miss Jane tanned your arse”

Standing naked before her with his hands positioned over his genitals he was loathed to pass on Nanny Hawkins message, but he knew he must.

“Please maam nanny Hawkins has asked if you would bath me……”

The young woman looked daggers at him and gritted her teeth.

“Doesnt that little madam think Ive got enough to do without bathing you, your old enough to do it myself…

Simon sighed and continued.

“Nanny also said that could you use the stiff bristled bath brush…….”

Anna stopped what she was doing and looked at the boy with interest..

In a quiet voice Simon added.

“And she said that if I misbehave you are to use the back of the brush on my bottom…”

At this the young womans eyes widened and she gave a small smile, laughing she chirped.

“You are going to be a sore little boy by the time Ive finish with you”

Ten minutes later Simon was standing in a metal bath half full of lukewarm water, as instructed he had his hands on his head.  Anna had disappeared only to return carrying a heavy long handled wooden bath brush,   soaping the brush she proceeded to spitefully scrub between Simons thighss, in a few seconds his genitals had been scoured by the hard bristles leaving him sore and tearful.   Feigning anger she dragged him out of the bath, and then seating herself on the bath stool she belaboured his already striped bottom with the back of the brush as hard as she could. For the next hour Simon was painfully scrubbed on every inch of his body, this was interspersed with sessions across Annas shapely thighs. He was soon sobbing uncontrollably his whole body red and sore, however, from the top of his buttocks to the back of his knees was a mass of nasty red blisters.   Anna put her hands on her hips and observed the sobbing boy kneeling at her feet, she smiled at the sight of his swollen buttocks,  also badly swollen was his penis which she had given special attention with the hard bristled brush.  As she ushered the boy back to his bedroom she curtly ordered him to change into his sailor suit as he was going to stay at Miss Frosts for a while, knowing the lady he would not be wearing the suit for long,   sissy Simon could expect a long hard session with Miss Frosts cane tonight especially as she hadnt had a boy in residence for some time…

Down in Janes bedroom Sir Charles was being rudely awakened by Mary, although the younger of the maids she was feisty and took no nonsense from anybody.  Drawing back the heavy drape curtains so the sunlight flooded the room she waited for the man in the bed to wake,   Sir Charles sore all over his body awoke with a start and glared at the elfin figure in a maids uniform standing looking at him.  Shaking his head he sighed.

“Alright if you give me a minute Ill dressed and get out of your way”

The girl grinned.

“Nanny Hawkins said I was to stay here while you dressed…and .if I was you I wouldnt keep her waiting or shes likely to tan your arse again”

Frightened Sir Charles leapt from the bed, to his dismay he felt something tightly secured around his genitals, looking down he could see his penis was encased in a tight brown leather sleeve, he could just see a small brass padlock which obviously secured it to leather straps around his testicles.  Panicking he tried to pull it off only to hear the girl chime in…

“I wouldnt do that Charlie boy, Nanny Hawkins fitted that on you, and shed be very upset if you took it off.”

Incredulous the man looked at it in horror, he knew exactly what it was and he had worn one for 6 months while a pupil of Miss Frost.

Jane was now anxious to deliver Simon into Miss Frosts not so tender care,   and propelled the boy along the street once again to No.8, if last time the boy had been nervous this time he was literally terrified.   No sooner had they reached Miss Frosts house than the door opened wide, standing there smirking stood Nurse Fraser, as Jane pushed Simon forward the woman pointed to the corner of the hallway, before the door closed Jane just had time to see Nurse Fraser insert her thumbs into the waistband of Simons short trousers and slip them down his thighs to around his ankles leaving his bottom completely bare!

Exactly one minute from the door closing onto the street and Nanny Hawkins disappearing 16 year old Simon Browns buttocks were completely bare.  A further five minutes later and these same well rounded cheeks had acquired a further 12 vivid and very painful cane weals to add to those given to him earlier by Nanny Hawkins.  However, poor Simons evening had only just begin; Nurse Fraser had been savoring the moment for weeks when she could introduce a new lad to her new leather strap, it was in fact a tawse given to her by her Scottish teacher sister but to the boy it would be pain.

Standing bare bottomed in the hallway Simon had no time to get his wits together,  feeling Nurse Frasers cold fingers in the waist band of his short trousers almost caused him to wet himself,  however, soon her hard palm was smacking out a tattoo on his bare cheeks.  The sting of the womans hand was to his horror almost unbearable, after a dozen slaps he was taken by the ear into Miss Frosts study.

Categories SexStory2 Date 15/03/2011