Trouble for Toby Pt. 03

Toby lay in bed thinking of what had happened to him at the hands of his cruel mature Aunt. He'd been tied in bondage, flogged, buggered by her strap on and finally pissed on and fucked. It was getting all too much for him and he could see no way of stopping the abuse other than running away but he had no where else to go.

Subconsciously he began playing with his cock as he thought about his Aunt peeing on him and began to get hard. Had he loved being fucked by her fake cock? He thought he had.

Just then his Aunt breezed into his bedroom for his nightly milking.

She was wearing her shiny silver dressing gown and mules. He instantly noticed she was wearing her tight shiny latex opera gloves and his cock got even harder.

'Right darling, Auntie is back to take good care of you. Let's get you naked and back on the bed.'

A naked Toby watched as his aunt dripped baby oil on her gloves and came over to seize his manhood. 'Hmmm, nice size. Have you been thinking naughty thoughts or were you just remembering what we did today,' she giggled.

Toby just blushed and moaned as she expertly brought him to orgasm a little quicker than normal, catching his cum in a towel that she used to clean her gloves.

'Oh, I think you needed that! Don't worry we'll be doing a lot of things like that soon. In fact I might need to see you in my bathroom first thing in the morning, darling. If you know what I mean? Sleep well little one.'

She kissed him and helped him back into bed before she disappeared into her own room.

The next morning Toby felt a tinge of disappointment when his Aunt came in to wake him up and milk him. Deep down he would have liked his mature Aunt to urinate on him again but it was a school morning and he had to get ready.

He wondered who would be taking care of him at lunchtime.

Soon it was noon and Mrs Atkinson, the school Secretary, came over to him and told him the Headmistress wanted to see him.

He was led to her office and shown in. The Headmistress locked the door.

'Well Toby, how did you enjoy your weekend? I believe it was extremely entertaining.' asked the headmistress.

Toby just hung his head and blushed.

'We need to see to your milking don't we young man?'

With that she ordered Toby to strip. As he undressed the headmistress unzipped her pencil skirt and tugged it down over her hips and off. She placed it on a chair before taking off her black silk panties. She was standing in her cream silk blouse, black stockings and suspenders and her black high heeled shoes.

When Toby was naked she knelt before him and took his cock deep into her mouth and sucked and licked his length until he was at full mast.

'We must put that to good use boy,' she said as she leaned forwards over her desk. Reaching out behind her she beckoned for him to come closer. Taking hold of his hard cock she placed it over the entrance to her pussy.

'Slide it all the way in boy and fuck me!'

Toby fucked her through two orgasms before filling her pussy with his cream.

The Headmistress rang for Mrs Atkinson, the school secretary, to come and take him back so he could have his lunch.

Mrs Atkinson smirked when she saw him and again Toby blushed as he knew she was aware of what had happened.

'Everything ok Toby?'

Toby nodded.

The rest of the week followed a similar procedure. His Aunt milked him in the mornings, either the Headmistress or the Matron used him at lunchtimes how they saw fit and his Aunt fucked him before dinner and sometimes at bed time.

At lunchtime it was supposed to be the Headmistresses turn to milk him but she was at a meeting with the Board of Governors so he was taken to Matron.

'Lock the door Toby. I'll be with you in a second,' said Matron from behind a screen. 'Take a seat.'

Toby sat on one of the hard backed chairs.

'Oh, and take off all your clothes first, that's a dear boy.'

Matron walked back out from behind the screen dressed only in her white hold up stockings and her white stilettos. He breasts swayed as she walked towards the sitting Toby. In her hand was a bottle of lube and a vibrator.

Toby looked aghast at what she might do to him but he was in for a greater shock.

Matron opened the lube and poured a good quantity on Toby's cock and stroked it until it was hard. She then turned her back on him and straddled his thighs. Taking hold of his cock she started to rub it over her puckered hole.

'Don't move Toby, let me do this or you'll split me in two,' she said.

She slowly sank her bottom down on his cock and after a little bit of effort on her part the head of Toby's dick slipped past her sphincter.

Even more slowly she sank down until all of his cock was fully lodged in her arse. 'Don't move, let me get used to it,' she asked.

Toby just sat there with his throbbing cock lodged tight.

She took hold of Toby's hands and placed them over her breasts.

'Play with my nipples please dear.'

She then took the vibrator that had at its base a vibrating cock ring and switched both on. She then slid the plastic cock deep in her pussy.

Toby could feel the vibrator throbbing through the walls of Matron's pussy and he moaned. 'You like that?' Matron asked as she pulled and pushed the phallus in and out of her pussy.

With one push she embedded it deep inside her so that the vibrating cock ring was tight against her clitoris. Toby could feel the tip of the vibrator pulsing against the head of his cock. His hips started to move.

'That's it Toby, fuck my arse.' Toby couldn't do anything but. The vibrator was playing on his cock and the tight walls of Matron's arse was so inviting.

'My nipples Toby, harder. Pinch my nipples harder,' she begged.

She was sitting on Toby's cock as he flexed his hips and she squirmed while pulling and pushing the vibrator in and out of her pussy.

'Oh my god, I'm cummmming.' she screamed. She pushed the fake cock deeper into her pussy which made Toby's cock expand as it vibrated on the crown.

As Matron came her pussy and arse constricted causing Toby to moan. 'Miss, Miss I'm going to...Oh god,' groaned Toby as he shot his load deep into Matron's bowels.

As Toby came Matron grabbed his head and leaned back pulling his face to hers and she kissed him deep on the mouth as they both shuddered to an almighty orgasm.

They sat there for a while until Matron sat up and pulled herself up from Toby's wilting penis.

'Right, er..Toby. You'd better get dressed and have your lunch. I'll see you again next week,' she said as she disappeared behind the curtain.

Life got back to normal for Toby. His aunt would milk him in the morning, his headmistress or the matron at lunchtime and his aunt would have her fun with him when he got home and before he went to sleep.

A week later the telephone rang in Aunt Margaret's house and as Toby was passing by it he answered.

'Ah, Toby, how is my favourite little slut?' asked Julia, his headmistress. Before Toby could say anything she said, 'Be a good boy and get me your aunt will you?'

Toby ran into the kitchen to get Aunt Margaret, who was busy making lunch.

'Hello? Margaret said down the phone.

'Hello darling, answered Julia. 'We've been invited to a party at the Brown's house next Sunday.'

'Who are the Browns? countered Margaret.

'You remember, you met them once at school. He is Chairman of the Board of Governors,' replied Julia. Margaret did remember them, mid fifties couple and she thought they were a bit full on at the time.

'We'll have to go of course, they've asked for Toby especially,' Julia carried on. 'I believe Bruce Jones and his wife Heather will be there and they are bringing the twins.'

The twins? asked Margaret. 'Yes they have a nephew and a niece that are twins,' replied Julia. 'They've looked after them for the last year as Heather's sister can't manage. It suits the Jones as the children are very submissive and I believe they don't stop fucking them. They've just turned nineteen. Bruce and Heather are about the same age as the Browns.'

'Oh do we have to go?' groaned Margaret.

'I'm afraid we do,' said Julia. 'Got to keep the Browns happy. Besides I quite fancy a pop at that young nephew.'

The following Sunday afternoon Julia called round to pick up Margaret and young Toby to take the party. 'Do we have to stay long? asked Margaret.

'Let's just play it by ear...or cock,' giggled Julia.

Julia pulled up the drive of an imposing detached house, parked and got out of the car. Before they could ring the bell the front door was opened by Mrs Brown.

'Do come in, everyone is here and so we can start the party.'

They were shown into the sitting room where Mr Brown was standing by the fireplace with a glass of whisky talking to Mr and Mrs Jones who were sitting on a sofa with their nephew and niece standing by the side.

'Ah Toby, nice to see you again. Ladies!' he said by way of a greeting.

Julia and Margaret accepted a glass of sherry and as the adults conversed the younger ones looked at each other appraisingly.

Suddenly Mr Brown spoke, 'right why don't we get things started?' Julia, Margaret why don't you take Tony upstairs,' he said nodding at the nephew. Bruce and I will take Clare which leaves my dear wife and Heather with Toby. Shall we meet back here in say two hours?'

Toby groaned inwardly on hearing he was going to be sexually abused by the two women for a couple of hours at least. He looked at the women who were about to use him more closely as they finished their drinks. Mrs Brown was plump with a huge chest and broad hips. She wore a tight fitting black leather skirt and a white silk blouse. Mrs Jones was a tall slim woman with short grey hair and a nice face dressed in a short black woolen dress.

Suddenly he was grabbed by the hand and dragged towards the stairs, the rest having left a few minutes earlier.

As they passed the first bedroom Toby could hear sounds of flesh on flesh. 'Ouch, no please uncle..ouch.' The next slap only produced a muffled complaint as if something had been stuffed in her mouth, then a groan from Mr Brown.

The next bedroom elicited moans and groans and he wondered what his aunt was doing or making the boy do to her.

The ladies took Toby into what looked like Mrs Brown's bedroom. It had a large wrought iron bed on which was a shiny black rubber cover.

'You undress him Heather while I get changed,' said Mrs Brown as she walked towards her en-suite bathroom and closed the door.

'Come here little boy,' said Mrs Bruce as she walked towards Toby and started to undress him.

When Toby was naked she pushed him back onto the bed, the black rubber sheets felt cold on his body. Heather then started to stroke his cock which soon became hard and throbbing. 'Oh my, we're going to have some fun with this,' she exclaimed as her hand worked up and down his shaft.

The bathroom door opened and Toby gasped at what Mrs Brown was wearing.

She was naked from the waist up allowing her huge breasts with extremely large nipples to wobble as she walked towards the bed. She was wearing a cream latex girdle that held up cream latex stockings and on her hands were elbow length cream latex gloves.

'Get yourself comfortable while I play with him,' she told Mrs Bruce.

Toby inhaled sharply as the cool rubber of her gloves wrapped around his cock. Out of the corner of his eye Toby could see Mrs Bruce slip out of her dress. She was naked underneath save for a pair of grey hold up stockings and high heels.

'Why don't you fuck him first Heather?' asked Mrs Brown. 'I want to sit on that cute face.'

Toby groaned as Heather Bruce straddled him and took his throbbing cock in her hand and rubbed it between her pussy lips before sinking down on it.

Mrs Brown climbed onto the bed and knelt beside his head. She took hold of his face and rubbed it onto her shiny latex girdle. 'Don't you just love the smell of the rubber?' she asked. 'You're going to love the smell of the inside when it is mixed with my pussy juices.'

She then straddled his face and he thought she was right, the smell was intoxicating.

Mrs Brown began to ride Toby's face as Mrs Bruce rode his cock. Soon all three were moaning in unison. 'Lick me boy!,' ordered Mrs Brown as she pushed her soaking wet pussy hard onto his face. Mrs Bruce was now on the soles of her feet riding him like a jockey, his cock almost coming out of her before she plunged back down.

'Oh shit!' exclaimed Mrs Brown, 'I'm coming.' Toby stuck his tongue deep into her pussy sending screams of ecstasy all through her body as she gave in to her orgasm. She climbed off Toby and watched on as Mrs Bruce rode him hard. 'Oh God,' she cried as her pussy gripped Toby's cock as her orgasm built. The tightness around the head of his cock sent a signal to Toby's loins and his prick swelled inside Mrs Bruce which pushed her over the edge and they both came together.

'I'm going to have a shower,' declared Mrs Bruce. 'I need to get rid of all this spunk that's in me.'

Toby laid back and watched as Mrs Brown approached him with a couple of silk scarves that she quickly wrapped round his wrists and tied them to the bed. She then reached over and squirted a large dollop of gel in her hands and with her left hand she took hold of his still hard cock and with the middle finger of her right hand she slipped it gently up his arse.

Mrs Brown slowly and teasingly masturbated the young boy as she tenderly finger fucked his arse with her latex gloved finger.

Soon Toby was bucking and trying to fuck Mrs Brown's fist to get relief but she just loosened her grip on his cock causing him to groan in frustration.

'Please...Mrs Brown, let me cum!' he begged. 'Oh you will cum soon when you're fucking me but not before.' she responded.

'Oh poor boy,' said Mrs Bruce as she entered the room and heard Toby begging.

Mrs Bruce went over to Toby and started to play with his nipples which made Toby moan and beg more. She bent down and kissed him on the lips, her tongue forcing its way into his mouth.

'I think he's hard enough now,' said Mrs Brown as Toby's cock was throbbing in her hand. Mrs Bruce untied his wrists as Mrs Brown laid back on the large bed with her legs open ready to receive a fucking from the horny young boy.

Further down the corridor if Toby had been able to look he would have seen young Clare astride Mr Brown who had his cock lodged in her pussy and her uncle kneeling behind her fucking her arse. She was moaning and groaning as she'd already had three orgasms so far thanks to the little blue pills the men had taken and she was on the verge of yet another.

In the other bedroom Tony, having serviced both of the older ladies twice with his mouth and cock, was lying face down and tied spreadeagled on the bed with Aunt Margaret whipping his bare bottom with a belt while being unable to cry out as his mouth was stuffed with the women's wet panties.

Julia, the headmistress was lubing up a seven inch strap-on and getting it ready to use on the unsuspecting boy.

'Come on then Toby, come and fuck me.' ordered Mrs Brown. Toby slid between the mature lady's thighs and groaned as he saw her lying there in her shiny latex outfit.

He slid his cock deep into her love hole while Mrs Brown wrapped her latex clad legs around his back.

Mrs Bruce laid beside them playing with her pussy. 'My turn next Toby. Save some of your cum for me, won't you dear?' she said as Toby started to fuck Mrs Brown in earnest.

After the two hours were over the well fucked ladies returned to the sitting room followed by the men and the youngsters who were all looking worn out.

Later that evening after they'd showered and eaten Aunt Margaret was sitting on her sofa while Toby sat in a chair as they watched the television.

'Is everything alright Toby,' his Aunt asked. 'Yes thank you Aunt Margaret,' replied Toby.

'Not too tired are you dear?' she said.

'No Auntie, not for you.' he sighed.

'Good boy,' she said as she headed up to her bedroom. 'Come along then!'