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Trouble for Toby - 1
by Croony (albert2er@yahoo.co.uk)

***

Fourteen year old Toby is orphaned and has to go to live 
with his spinster Aunt Margaret. (FF/m-teen, ped, d/s, 
reluc, inc, toys, 1st)

***

PART 1

Toby Jones was a 14 year old boy, who recently orphaned, 
had just moved into his Aunt Margret's huge house in 
Rottingdean near Brighton. His parents had been killed 
in a car crash just over a month ago and 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 young boys, especially those of Toby's 
age.

Toby was a cute boy. 5'4” tall, slim with wavy blonde 
hair, bright blue eyes and pouting red lips. He'd just 
become interested in girls but because of his small 
stature and feminine looks girls weren't interested in 
him. If they had know 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 recently discovered 
the joys of masturbation and also recently he began to 
fantasize about 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 the 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.

Little known to Toby but 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 keen on young 
boys too.

After hearing what his aunt had to say Julia said there 
might be a way Margaret could have what she desired but 
only if she was willing to share Toby. After what Julia 
told her what her plan was Margaret readily accepted her 
offer.

The next day Aunt Margret went out and bought some 
liquid Viagra from a friend of hers and proceeded to 
lace Toby's bedtime and morning drinks.

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 young 
boys in the 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 busty redhead. Not as tall as Mrs. Atkinson or even 
the headmistress but her breasts outweighed her lack of 
height. Even at 5'4” she was still taller 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 eye line.

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 stockinged-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 but 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 as he was 
then 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 and Toby was 
loving it. 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 pre-cum 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 pre-cum 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 he could 
tell her 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 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 
boys 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.

'Oh miss. Please stop. Please, I think I'm going to... 
oh noooo!'

Toby came all over his headmistresses thighs.

'I...I-I'm so sorry miss.'

The head mistress pushed him off her lap and on to the 
floor as a long line of spunk clung to her thigh and the 
end of his cock.

'Matron, take him to get dressed while I tidy myself up. 
Toby meet me back here after school. I'm going to take 
you home and have words with your aunt and discuss what 
we need to do with you,'

Toby just nodded in mortification as he followed the 
matron to her room.

At 3.30pm Toby was sitting on a chair outside the 
headmistresses off when Mrs. Atkinson walked by.

'Ooh. Have you been a naughty little boy Toby?'

He just nodded.

'Can I help you with anything?' she said in a low sexy 
voice.

Toby shook his head.

Mrs. Atkinson crouched down next to him and put her hand 
in his lap to steady herself. 'Well if I can, you just 
let me know' she said as she squeezed his cock through 
his trousers.

Toby groaned.

Just then the headmistresses door opened but Mrs. 
Atkinson was up and heading back down the corridor.

'Right Toby. Let's be on our way.'

Toby was not looking forward to this.


Aunt Margaret was home as planned when Toby and Julia 
got there.

The headmistress went on to explain what had happened 
and Margaret managed to glare at him and tut tut in all 
the right places whilst at the same time feeling 
incredibly turned on.

'The thing is,' said Julia, 'matron thinks he is 
suffering from Priabatism which is a condition where the 
male is forever sporting and erection and producing a 
great amount of semen.'

Aunt Margaret knew this to be a made up diagnosis but 
played along with it. 

'What can be done?'

'Well matron says Toby will have to be milked regularly 
on a daily basis. Once in the morning, once at 
lunchtime, once when he returns from school and once 
before he goes to sleep.'

'Oh dear, how do you propose I do that?' asked Margaret 
feigning shock.

'We'll, that is matron and I, will take turns with the 
lunchtime milking if you can manage the others.'

'B-but how do I ...err... milk him?'

'You can use your hand or even your mouth and for a 
change you could milk him vaginally.'

'Oh my goodness. Won't that be incest?'

'Nonsense Margaret, this is purely medicinal.'

Poor Toby was aghast at what he was hearing.

'Why don't we start now?' asked the headmistress. 'You 
can practice Margaret while I supervise'


'Toby strip.' Toby didn't move. 'Matron says he responds 
sexually to anal penetration and I know he enjoys being 
spanked, of course.'

'Toby, do as Julia has asked and quickly!'

Toby slowly peeled off his clothes to the delight of his 
aunt. When he was naked he was ordered by his 
headmistress to put his hands by his side. His cock 
started to grow almost of its own free will. Little did 
Toby know that the liquid Viagra was complicit in his 
hardness.

'See what I mean, Margaret. The naughty little boy can't 
keep it down.'

'Yes Julia, he does seem to have a problem. What do you 
suggest we do?'

'We milk him, of course!'

Aunt Margaret took a long look at her nephews hard cock 
before standing up from her chair and walking over to 
him. She reached out and began to lightly stroke his 
straining cock. Toby moaned at his mature aunt's touch.

'Be careful Margaret. His cum really flies out. I would 
take off your blouse if you don't want it stained with 
his cum.'

'Yes, good idea Julia.' Aunt Margaret said as she stood 
in front of the mesmerised young boy and started to 
unbutton her tight satin blouse. She went one further 
and unzipped her skirt and let it fall to the floor.

Toby gaped at his statuesque aunt clad only in her black 
satin girdle that had black seamed stockings attached. 
Her black silk bra held up her magnificent breasts and 
in her black shiny high heeled ankle boots she towered 
over him.

She knelt down in front of him and taking hold of his 
ever harder cock she asked, 'right where we?' She began 
a slow teasing stroke that soon had Toby groaning and 
after only a little while he automatically began by 
moving his hips faster to fuck his aunt's fist. 'Oh you 
are keen, aren't you darling boy?'

'Please Aunty, faster. I need...'

'Yes Toby, what do you need?'

'Oh God, I need to cum.'


Aunt Margaret took pity on her nephew and pumped her 
fist faster up and down his huge cock. 'You will owe me 
for this young man?' 

'Yes, yes, oohh anything Aunty! Aaarrrgghh!' 

His first rope of cum hit his aunt full on her chest, 
splattering her boobs and splashing over her silky bra. 
The next hit her in the face as she pulled his cock to 
her mouth and she managed to take the rest down her 
throat as her ruby red lips milked the rest of his cream 
from his deflating cock.

''Quick lie down, get down on your back.'

Toby did as he was told and watched as his aunt sipped 
her panties down her thighs and completely off. He was 
still wondering what was going on when she straddled his 
head and sunk her streaming pussy over his face.

'Lick me boy, lick my pussy until I cum.'

Toby extended his tongue as his aunt began to fuck his 
face. She could feel Toby's nose rubbing at her clit as 
his tongue flicked in and out of her slit.

Soon she was ready to cum as she lifted his head in her 
hands and jammed his face in her gushing cunt. 'Drink 
it, drink it all', she said as she squirted her juices 
into his mouth. 

Eventually she got off him only for Toby to see Julia 
sitting in her chair, her panties hanging from one ankle 
and her legs hanging over the arms of the chair.

'Come here boy, you haven't finished yet.'

With a groan Toby got to his knees and crawled over to 
his Headmistresses open thighs.

'Pleasure me' she ordered. Once again Toby felt his face 
between a mature lady's thighs. She pulled his face onto 
her sex and Toby set to work. 
Aunt Margaret marvelled at the way Toby set about 
wetting her friends pussy. She had replaced her skirt 
and blouse but left off her panties.

Soon Julia was in the throes of passion calling Toby 
names and cumming on his face.
When her orgasm subsided she pushed Toby away only to 
declare, 'Oh my god, he's hard again!'

Aunt Margaret stared at her nephew and asked, 'what do 
we do now?'

'We take him upstairs.'

'Now!' exclaimed Margaret.

'Why not, he has to lose it sometime.'

Margaret smiled, helped Toby up and taking hold of his 
hand and led him up to his bedroom. Toby was in 
bewilderment. His heart was pounding and he was weak 
from two almighty cums. Surely they weren't going to... 
No he couldn't think about that.

Margaret and Julia certainly were.

In the bedroom Julia asked Margaret to fetch her four 
silk scarves which she duly did. Soon Toby was spread-
eagled naked on his bed and could only watch as the two 
mature ladies undressed to their underwear. Margaret 
took off her black silky bra this time and Toby 
marvelled at her massive breasts with hard erect 
nipples. Julia has undressed just leaving on her black 
stockings and her matching suspenders. Her breasts 
bounced as she walked over to the prone Toby.

She knelt on the floor beside his head and taking hold 
of his cock she leaned in and whispered, 'We're going to 
fuck you little boy,' and with that she squeezed his 
dick hard causing him to groan.

'You can have the honours,' she said to Margaret.

Margaret walked over to Toby and stroked his face. 'Be a 
good little boy for Aunty, won't you?' Toby could only 
nod his head as he watched his aunt straddle his thighs 
then take his cock in her left hand and line it up to 
the entrance of her pussy.


'Say goodbye to your virginity young man' as she plunged 
down onto his hard meat causing Toby to gasp then moan 
at the pleasure of his aunts tight sleeve slipping 
around him.

'Oh fuck Julia, that is so good.'

She began to slowly ride her nephew. She would raise up 
until his cock was once again at her entrance before 
thrusting back down as her meaty thighs slapped against 
his. Soon her motions were getting faster as she fucked 
him relentlessly. Julia couldn't tell who was moaning 
the most.

Soon Margaret could feel her young nephews cock grow in 
girth and knew he was about to cum inside her. This 
pushed her over the top and her orgasm started, gripping 
Toby's tool and milking him of his cum as they both 
shouted out their release.

Aunt Margaret rolled off her nephew and law on her side 
stroking his smooth young body as he lay still, 
breathing heavy. 'That was fantastic darling, I think we 
may be doing a lot more than that in the future.'

Margaret, why don't you get cleaned up and pop 
downstairs and I'll join you as soon as I've had my turn 
on that wonderful cock. Margaret nodded in agreement and 
after gathering her clothes she left the room.

'Just you and I now little boy. I'm going to get you 
hard and show you how to fuck a real woman. When I've 
finished with you you'll be able to service all my 
friends, even Mrs. Atkinson that you've fantasised about 
since you arrived at the school.' Toby was hard 
instantly on hearing this. 'Looks like you're looking 
forward to something. I hope it's me,' as she took his 
rapidly hardening cock in her mouth. 'Oh Miss' groaned 
Toby.

An hour later Julia Johnson walked back into the sitting 
room where Margaret was reading a book.

'He's all yours for the evening Margaret, I bet he still 
has a few good fucks in him before he falls asleep.'

'How have you left him?' asked Margaret.

'Still tied to the bed but I forced a vibrating butt 
plug up his arse and left him moaning and writhing with 
another erection.' 

When Julia had left Margaret went back to the bedroom to 
find Toby with Julia's panties stuffed in his mouth and 
his huge erection spilling pre-cum all over his groin. 
She removed the panties and Toby begged to be untied.

Margaret took hold of his cock and began to stroke it. 
'Well, you seem to enjoy things up your arse Toby. Maybe 
I should buy a strap-on and fuck you properly?' At 
hearing that Toby erupted all over his aunt's hand. 
'Mmmm, that seals it. I'll go on line tomorrow and order 
one.'

She went along to the bathroom to wash her hands before 
freeing Toby. On her return she could see that he hadn't 
lost his erection at all.

'Oh, well, it's a shame to waste it.'

She rode Toby and had four orgasms before he finally 
came deep inside her.

'This is going to work out perfectly,' she thought.

To be continued...

*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*
The author does not condone child abuse, this story is 
meant as an erotic fantasy not depicting anything in 
real life. Anyone acting out such scenarios in "real 
life" can look forward to many unproductive years 
getting it up the butt by a fellow convict in their 
local prison system.
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Kristen's collection - Directory 83