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Trouble for Toby - 2
by Croony (albert2er@yahoo.co.uk)
quick edit by JasperSmithers

***

The further exploits of Toby at the hands of his 
spinster Aunt Margaret. (Fdom/m, ped, nc, inc, bd, ws)

***

PART TWO

That night Toby had a fitful sleep remembering what his 
mature Aunt and his even more mature Headmistress had 
done to him. He was permanently turned on and his cocked 
throbbed. He had never felt like this before and he 
wondered why.

He still hadn’t realised that his Aunt Margaret had been 
lacing his drinks with liquid Viagra.

He didn’t hear his aunt come into his bedroom the 
following morning and only noticed when he felt the bed 
sink under her weight as she sat down.

She stroked his face tenderly. "Good morning Toby," she 
cooed. Toby looked up to see his aunt dressed in a pink 
see through baby-doll nightie with her large breasts 
visible under the sheer negligee.

"Did you sleep well darling?"

"Err, yes thank you Aunt Margaret," Toby replied.

"Well, we know what we have to do now don’t we? So why 
don’t you slip those pajama bottoms down and I’ll give 
you your morning milking?"

Toby eagerly peeled down his night time shorts as his 
aunt pulled back the duvet. He was already hard at 
staring at his aunt’s breasts.

"Mmmm," murmured Margaret as she took hold of his 
throbbing cock with her right hand and cradled his balls 
in her other.

She slowly began to peel the foreskin over the shiny 
head of his prick that was wet from pre-cum. She wanked 
him, listening to his moans and watching the motion of 
his young slim hips. She could feel he was ready to 
ejaculate so she took her left hand and used her sharp 
nails on his balls making him gasp and spurt ropes of 
cum out of his slick cock.

"There’s a good boy. Why don’t you have a shower and 
come down for your breakfast. I’m going out this 
afternoon shopping but I’ll take care of you before I 
go." Aunt Margaret got up and went back to her own room 
to get ready.

***

The morning passed quietly with Toby watching the tv and 
Margaret doing housework. 

After a light lunch she did indeed take care of Toby by 
giving him an exquisite blow job and receiving a 
mouthful of cum for her pains.

The rest of the day was spent playing games on his iPad 
until his Aunt came bustling in laden with boxes and 
bags at 5pm.

"Toby, go to your room right now. I want you to be 
standing by your bed naked. I’ll be there in fifteen 
minutes."

She seemed excited and out of breath. Toby did as he was 
told and was standing naked by the bed when his aunt 
finally entered.

She was only wearing a black satin girdle with dark grey 
sheer stockings and her shiny black high heels. She 
walked past Toby and lay down on the bed with her knees 
up and her legs wide open. "Get up on the bed and stroke 
your cock until it is hard."

Toby did as he was told and knelt between her splayed 
thighs stroking his cock to hardness as he watched his 
magnificent mature Aunt finger her bald pussy until it 
was squelching with her juice.

"C'mon boy, fuck me!"

Toby moved between his Aunt’s thighs and pushed himself 
home with one thrust.

Margaret moaned and immediately wrapped her stockinged-
thighs round his back and met his thrusts with her own. 
Several times she stuck her high heels in his buttocks 
to spur him on, telling him not to cum until she said he 
could.

After her third orgasm that Toby could feel dripping on 
his crotch and balls she ordered him to cum. He sped up 
and could feel his cock expanding, ready to spill it’s 
load in his Aunt’s tight hole. 

"Now Toby, now!" said Aunt Margaret as she succumbed to 
yet another orgasm. Her pussy gripped Toby’s cock 
tightly and milked him once again.

They lay side by side panting for breath after such a 
frantic fuck.

"Wait until you see what I’ve bought today darling," 
said Margaret when she got her breath back. "We’re going 
to have a play day tomorrow." 

Toby didn’t dare ask what was in store but he knew it 
just had to be something sexual.

***

After dinner Toby got ready for bed and waited while 
reading, for his Aunt to come in and give him his 
nightly milking.

Just after ten pm his Aunt appeared in a tiny black see 
through baby doll with a black silk g-string. She told 
Toby to get up so she could sit back on the bed. "Come 
and lie down dear with your head in my lap."

Toby did as he was told and his Aunt took hold of his 
rapidly hardening cock and began to masturbate him. "You 
are a very naughty boy Toby for making Auntie so very 
horny all the time by sporting a big hard erection that 
tomorrow I’ve decided I’m going to punish you."

She then peeled down her top and bared her breasts. All 
she said was, "Suck!" as she offered Toby her long hard 
nipples.

She began to wank him harder telling him what a naughty 
boy he was and how he was going to pay for it. He soon 
felt his balls tingle and his cock growing. All he could 
do is moan around the nipple in his mouth as he came all 
over his Aunt’s fingers. "Get cleaned up and try to have 
a good night's sleep," his Aunt said as she left the 
room. Just as she was closing the door she said with a 
smile, "You’re going to need it!"

***

Surprisingly Toby slept well and didn’t wake until his 
Aunt knocked on this door at ten the next morning.

She popped her head round the door. Good morning 
darling. Get washed and dressed then come down for your 
breakfast when you’re ready.

Toby thought it odd that she hadn’t milked him but then 
remembered her threat to punish him. That played on his 
mind as he showered and dressed.

Aunt Margaret was busy in the kitchen when Toby 
eventually came downstairs. She was dressed in a full 
length silver silk dressing gown and fluffy pink mules. 
She’d made him a coffee and put extra drops of liquid 
Viagra in as she felt he might need it today.

"I’m going to be busy in my room this morning dear so if 
you don’t mind amusing yourself I’ll see you down here 
for lunch at noon, is that ok?"

Toby nodded and said, "Yes Aunt Margaret."

She walked over to him and kissed him full on his mouth, 
her tongue pushing into his mouth as she hugged him. She 
broke the kiss and pulled his head onto her chest. Toby 
could feel her naked breasts beneath the cool silk gown. 

"I hope you will be a good boy for me today, Toby."

Toby again nodded but didn’t say anything, he was 
starting to get concerned as to what she had planned.

***

Lunch was just a ham sandwich and the obligatory Viagra 
laced orange squash.

"Right darling, I want you to come up to my room in 
exactly one hour, knock on my door and wait. I expect 
you to be naked." Aunt Margaret proceeded to walk 
upstairs leaving Toby to clean away the dishes and 
contemplate what was in store for him.

***

Exactly one hour later a naked Toby knocked on his 
Aunt’s bedroom door. A few seconds later it opened. His 
Aunt was standing behind the door and said, "Come in." 
She closed the door, locked it and stood with her arms 
on her hips.

"Well, do you like my new outfit?"

Toby could only look on in amazement. His aunt was 
dressed in a tight shiny black pvc corset that came just 
below her naked breasts. It held up shiny black 
stockings with four suspenders on each leg. She wasn’t 
wearing panties and her naked sex was glossy, her pussy 
lips wet with her juices.

She wore extremely high shiny black heels and on her 
hands and arms were shiny black latex opera gloves that 
came up to her elbows.

"Well little boy? What do you have to say?"

"I err... Well... Auntie I..."

"No Toby. Not Auntie in here. In here you will refer to 
me as Mistress. Do you understand?"

"Yes Aun... err... Mistress."

"Good boy now why don’t you come over here and I’ll show 
you what else I bought yesterday?"

Toby walked over to the centre of her room and stood 
before her large four poster bed. She walked up to him 
and fastened cuffs to each of his wrists then rope which 
was attached to a pulley above his head that Toby hadn’t 
noticed.

Soon his arms were stretched high above his head and 
locked into place as he was forced to stand on tiptoes.

She fastened a three foot spreader bar to his ankles 
making it awkward for him to move. "We’re going to have 
an afternoon of pain and pleasure. Your pain and my 
pleasure slave." She reached into a box and pulled out a 
black leather flogger.

"Look slave, let’s see how this feels." She brought it 
hard down on Toby’s bare buttocks. 

Toby let out a squeal as the strands of leather bit into 
his bottom leaving pink marks where they landed. 
"Please! NO!" Another blow landed this time in a 
different place on this bum.

"Quiet slave or I’ll whip you harder!"

Toby tried to suffer in silence as more blows rained 
down on his now reddening arse. He whimpered as his 
bottom began to sting more and more. He hung his head 
and was astonished to see his cock was harder than it 
had ever been and pulsating as his rear end was being 
attacked.

The next blow was lower and some of the strands whipped 
round his thigh and landed on his balls. Toby groaned in 
pain and excitement. His Mistress Aunt realised this and 
continued whipping his thighs and balls.

She whipped up between his legs and caught his cock and 
balls together. Toby gasped in surprise and groaned deep 
and hard. Pre-cum was dripping out of his throbbing 
cock. She walked round to face him. She was breathing 
heavily with excitement and took his cock in her shiny 
black latex glove.

"Maybe I should whip this naughty cock of yours, she 
said squeezing it."

Toby moaned and pleaded, "No please Mistress, not that. 
Please let me down."

Aunt Margaret just laughed and said, "Soon."

Another fifteen minutes of punishment to his bottom, 
thighs, cock and balls left Toby groaning and begging 
her to stop. This turned Margaret on even more. She put 
the flogger down and stood in front of him, stroking his 
cock. She leant into him, kissing him hard on the mouth 
as he felt her cool pvc corset and her naked breasts 
push into his torso.

"Maybe I should put something on your poor little hot 
bottom to soothe the pain away." She lowered the rope 
and untied his hands but left on the cuffs and ankle 
spreader bar. This made it difficult for Toby to walk as 
his aunt led him over to a small leather padded bench 
about three feet tall. 

"Bend over slave so I can deal with your bottom." Toby 
did as he was told and was surprised when his aunt 
attached his cuffs to clamps on the front legs and then 
his ankles to the rear legs of the bench.

He felt her cool latex gloved hand lovingly stroke his 
bottom. She slid her hand under the bench and fondled 
his balls. Toby gasped and then moaned as she wrapped 
her latex covered fingers encircle his hard throbbing 
cock.

Aunt Margaret leaned forward and whispered in his ear, 
"I think you’ll like what’s going to happen next my 
little slave."

He felt cool gel soothing his hot bottom and moaned in 
relief as it was spread all over. He felt her fingers 
sliding down between the cheeks of his bottom and over 
his hole. He shuddered. Then more gel was squeezed onto 
her shiny gloved fingers and he felt his bottom being 
penetrated by at first one then two and finally three 
fingers pushing gel deep inside of him. 

He moaned as his Mistress finger fucked him. "W-what are 
you doing?!" he pleaded.

"Just making you nice and slick slave. You’ll see."

He heard the door to the en suite open and close and a 
few minutes later Aunt Margaret came back in and stood 
before him. At head height he could see the black 
lifelike strap on cock she was wearing around her waist. 

"Oh god, no please Aunt Margaret! Not that!"

"Oh yes slave, and for not calling me Mistress, I’m 
going to fuck that sweet little arse of yours even 
harder. Now open your mouth and suck it like it was a 
real cock or I’ll whip you some more."

Toby opened his mouth to accept the phallus.

"That’s it suck it slave. Get used to it, you’ll be 
sucking a real one real pretty soon." Toby groaned and 
tried to put the thought out of his mind but he 
couldn’t. Who will I be sucking, will I be fucked, he 
wondred.

"Oh yes young man, there's a couple that have asked if 
you can stay with them on Friday night and I’ve agreed. 
I’m going to break you in for them and have fun doing 
it."

She pulled the cock out of his mouth and walked behind 
him where she rubbed the end of it up and down the crack 
of his arse to get it covered in gel. His aunt then 
placed it at his opening. She pushed gently but forcibly 
into him. Toby let out a gasp as it penetrated his 
sphincter and a long moan as his aunt pushed the cock 
deep into his arse.

She held it there to let her nephew get used to it then 
pulled it out almost to the end and pushed it back into 
him a little faster this time. Toby grunted.

She started to fuck him telling him what a naughty boy 
he was and she would keep on fucking him until she came. 
The other end of the cock was rubbing hard on her clit 
as she fucked him and she had to suppress a moan when 
her first orgasm hit her.

She continued pounding his arse as Toby groaned, moaned 
and grunted as the cock slid in and out of him. His cock 
was leaking pre-cum by the gallon as the cock rubbed 
over his prostate. Margaret could feel her orgasm 
building and was just about to scream when she took hold 
of Toby’s slick cock and began to wank him as she rode 
him to orgasm. 

"Oh yesss!" she cried, as her juices exploded out 
between her pussy lips. Cum slave, cum for your 
mistress, as she fucked and wanked him harder, her 
orgasm still pouring out of her.

"Oh god!" Toby cried out, as he shot ropes and ropes of 
spunk over his aunts hand and carpet. 

After they had calmed down his aunt pulled out of him 
slowly, standing up she unbuckled the harness then set 
about setting Toby free. She helped him stand up and 
taking hold of his cock she led him into her bathroom. 
Taking him into the large walk-in shower she ordered him 
to lie down on his back. He winced as the cold tiles 
come into contact with his body.

His aunt stood over him, tall and statuesque clad in 
shiny black pvc and latex. She parted her pussy lips 
with her fingers and looked down on her prone nephew. 
No, she can’t, he thought but by the look on his aunts 
face and her concentration he just knew what was about 
to happen. 

The first dribble of pee landed on his thighs then more 
rained down over his cock. Suddenly a deluge cascaded 
down over his chest and up towards his face. "Drink it 
slave! Play with your cock."

Toby stroked his cock and spluttered as the golden 
shower hit him full in the face. He opened his mouth to 
breathe as his aunts piss landed in his mouth and he was 
forced to swallow it. "Good little slave," she said as 
she continued to soak him.

Toby’s cock was huge and hard by the time his aunt had 
finished and seeing it in all its glory she sank down on 
it, his cock sliding easily between her wet pussy lips. 

She rode him to a further three orgasms before he 
exploded inside her. She leaned into him and kissed him 
deep on the mouth.

"Mmmmm I think we’ll have a lot more play days like this 
in the future."

To be continued?

--------------------------------------------------------
This story was written as an adult fantasy. The author
does not condone the described behavior in real life in 
any way, shape or form. Anyone tempted to act out any of 
the scenarios in this story should seriously consider 
seeking professional help.
--------------------------------------------------------
Kristen's collection - Directory 83