Trouble for Toby

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.'

'Er...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 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 precum. 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 dug her sharp fingernails into 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 television 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.

'Come on boy, fuck me!'

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

Margaret moaned and immediately wrapped her stocking 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 10pm 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 so I've decided I'm going to punish you tomorrow.'

She then peeled down her top and bared her breasts. All she said was, 'suck,' as she offered Toby one of 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 nights 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 ordered him to go 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 latex corset that came to 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 er.. Well.. Auntie I..'

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

'Yes Aun..er 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 hid 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 said with a giggle.

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 noooo...'

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. Precum 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,' Nooo, 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 leaned into him, kissing him hard on the mouth as he felt her cool latex 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. 'What, 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 is a real cock or I'll whip you some more.'

Toby opened his mouth to accept the phallus.

'That's it suck it slave.'

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 gave out a long moan as his aunt pushed the cock deep into his bottom.

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 precum 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 yessss', she cried as her juices exploded out between her pussy lips. 'Cum slave, cum for your mistress,' she chanted as she fucked and wanked him harder, her orgasm still pouring out of her.

'Oh god', Toby cried 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 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 aunt's 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 two 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.'