Toby Jones was 18 years old when his parents were killed in a car crash and he had just moved into his Aunt Margaret's huge house in Rottingdean near Brighton.
His parents had left a will asking Margaret, his father's sister, to look after him until Toby was able to access the trust fund his parents had set up when he reached the age of 25.
As Margaret didn't need to work due to a huge inheritance and some excellent investments over the years it was thought it right and proper that she should look after her young nephew.
Margaret, a 47 year old spinster had no end of male admirers as she was a very striking woman of 5'10" in her stockinged feet and a fine hour glass figure with certainly impressive breasts. However she wasn't interested in dating men her own age as she had a predilection for younger men,
Toby was a cute boy. 5'6" tall, slim with wavy blonde hair, bright blue eyes and pouting red lips. He was interested in girls but because of his small stature and feminine looks girls weren't interested in him. If they had known he had a thick 8" cock when erect they may have changed their minds.
It was all new to Toby, a new place to live, a new house and a new school where he hadn't yet been able to make any new friends. All he did was go to school, do his homework at night and wank.
Toby had discovered the joys of masturbation many years ago but recently he began to fantasize about his Aunt Margaret. It could have been the tight pencil skirts she wore or the tight blouses with her gleaming white pearls around her neck. Maybe it was the seamed stockings and high heels that got him so excited. Whatever it was he wanked his cock dry most nights thinking about her.
Margaret also thought about her nephew and at nights dreamed about how she could snare him and make him her sexual plaything.
She began leaving her underwear drying in the main bathroom that Toby used, stockings, panties and once one of her satin corsets. She was sure that Toby would notice them and notice them he did.
One evening after school he went into the bathroom to freshen up before dinner and he noticed a pair of his aunts shiny black silk panties lying half out of the dirty linen basket. Toby was drawn to these sexy knickers. He sniffed them and groaned. The scent of his aunts mature pussy wafted up his nostrils and his prick pulsed with excitement.
He debated whether to sneak them back to his room but he felt that was too dangerous as his aunt might notice them missing so he kicked off his school trousers and underpants and sat on the edge of the bath and wanked furiously all the while taking in the aroma of the used panties.
What Toby didn't know was that his aunt was sneakily looking through the bathroom keyhole and saw everything as it unfolded. When Toby kicked off his underwear she nearly gasped out loud at the size of his huge young cock.
It was at that moment that she realised that she not only wanted him as her lover but that she wanted to own him and possess him entirely.
Later that night after Toby was tucked up in bed she made a phone call to Julia Johnson who just happened to be not only Toby's headmistress but also Margaret's best friend.
After hearing what his aunt had to say Julia told her that there might be a way Margaret could have what she desired but only if she was willing to share Toby. After Julia told her what her plan was Margaret readily accepted her offer.
The next day Aunt Margaret went out and bought some liquid Viagra from a a chemist friend of hers who didn't ask any questions and proceeded to lace Toby's bedtime and morning drinks with it.
On Friday Toby was feeling horny all the time and when Mrs Atkinson the school secretary called him out of class towards the end of the morning lessons his cock started to grow even harder. She told him he had to go to see matron and to follow her.
Mrs Atkinson was a 32 year old, tall, slim blonde with long legs that today were accentuated by black high heels. She was the wank fantasy for most of the boys in school. Toby's eyes were glued to Mrs Atkinson's swaying bottom as she walked a little in front of him and he felt his cock swell.
Matron, or Mrs Jackson as she was also referred to, was a 40 year old busty redhead. Not as tall as Mrs Atkinson or even the headmistress but her breasts outweighed her lack of height. Even at 5'5" she was still taller than him in her cream high heels which today looked even higher than normal. As she walked passed him and locked the door her uniform seemed a lot tighter and shorter too. Her front fastening zip seemed to be lower as her large breasts seemed to burst out and drew Toby's eyeline.
There were two high backed chairs at an angle to each other and Toby was asked to take a seat in one. Matron then proceeded to bend over to retrieve a file from the bottom drawer of a cabinet and as she did so her uniform crept up showing Tony not only her white stocking tops but the white thong she was wearing. His cock got even harder.
She joined Toby on the next chair, asked him some routine heath questions then told him it was time for his physical and to take off all his clothes Toby didn't move. He couldn't, his cock was rock hard from the site of her stocking clad legs and thong, not to mention her large jutting breasts. 'Come on now Toby, place them neatly on the back of his chair.' Toby still hesitated.
Matron told him firmly once more to undress and this time he complied.
When he was naked he stood before matron with his hands cupped over his growing erection with little success.
She ordered him to put his hands by his side and when she saw his cock she almost salivated. She weighed him, measured his height and even took his inside leg measurements just so she could kneel and let her long red hair tickle his dick.
Suddenly Toby heard a snap of a latex glove being pulled on and as he looked over he saw matron reach for a tube of lube. Toby thought he was going to faint when was ordered to lean over the examining couch at the back of the room and open his legs with his bottom pushed out.
He walked over hesitantly and lay with his chest on the bed and his bottom up for his examination. First he felt the cold lube being rubbed around his anal ring and then the pressure of matrons finger penetrating his hole ever so slowly.
He groaned at the insertion and even more so when she pushed her finger the full length to find his prostate. Matron was now finger fucking Toby's arse. Suddenly she stopped but only to apply more lube and insert an additional finger. Toby gasped as the two fingers worked on him. By the time three of matrons fingers were working in and out of his arse Toby's cock was leaking copious amounts of precum onto the floor and matron sensed he was about to erupt. Swiftly pulling her fingers out she took Toby back to the middle of the room where she knelt in front of him to examine his penis. She made sure the skin wasn't too tight around the head by taking his cock in her fist and moving it up and down several times quickly. Then when she peeled the foreskin back she coated her finger in his precum and spread it over the crown of his cock.
This proved too much. He could only moan and shake as the first rope of cum hit matron on her chin, the second on her throat and the third spurted all over her cleavage. The rest dribbled over her starched white uniform as she gasped in amazement at the amount he produced.
'Jones!'
'Sorry Miss.'
'That is disgusting young man' Matron tried to sound annoyed but practically orgasmed as his fluids dripped from her face onto her heaving bosom.
'Right, we need to go to see the headmistress about your disgusting behaviour.'
'Please Miss, I'm sorry Miss, I didn't mean to Miss.'
She pulled him by his still stiff cock to the side door that led into the headmistresses office. She knocked and heard the headmistress beckoning her in. She dragged Toby inside and pushed him in front of the headmistress before locking the door and recounting the incident.
Julia Johnson had made sure she was looking particularly sexy for this. Her black suit skirt was shorter than normal and she was wearing the jacket without a blouse but with a black push up bra that pushed her 34DD tits up to maximum effect. Like Toby's Aunt Margaret she often wore her shoulder length black hair in a bun and today was no exception. She looked dominant but extremely sexy.
'Well young man I think you need to be punished, don't you? What do you have to say for yourself?'
Toby was so appalled at what had happened that all he could was how sorry he was and that he didn't mean to. He told her he'd been feeling strange for a couple of days and that he didn't know what was happening to him.
The headmistress walked over to a sofa at the side of the room and asked Toby to go over. To Toby's surprise she pulled up her tight black skirt up over her thighs and ordered him across her knees.
At the sight of his headmistresses stocking tops held up by suspenders his cock was once again rock hard. As he settled over her lap she opened her legs and trapped his cock between her warm naked thighs and the rough tops of her stockings.
She began to spank him, telling him what a dirty little boy he was. This just made Toby more horny. She ordered him to open his legs and when she spanked lower her fingers would catch Toby's balls making him moan even more.
Julia then moved forward slightly which caused his cock to rub against her suspender clasp. The quicker she spanked the quicker his cocked rubbed between flesh, stocking and clasp.
All of a sudden Toby could feel his cock start to expand and he knew he was about to cum. Julia also noticed his cock growing and spanked harder.
