Trouble for Toby Pt. 05

Oh you are so lucky Margaret,' said Julia Johnson, Toby's headmistress. 'You have Toby at your beck and call to do whatever you want and to act out all of your deviant fantasies whenever you want. I, on the other hand, haven't even enjoyed a dalliance at lunch break with him with all these new meetings and extra curricular activities I have to attend to.'

'Well actually,' intoned Aunt Margaret, 'Toby is growing up fast. He has new friends he hangs out with these days and I have to take my chances with him. I'm as frustrated as you these days.'

'Where is he now?' asked Julia hopefully. 'Oh he's out with his new friend,' answered Margaret. 'They like to hang around the town centre looking for girls. They do it every Saturday afternoon.'

At tea time Toby sauntered in with another young man in tow.

'This is my friend Saul,' said Toby introducing the boy to his aunt.

Margaret managed to hide her excitement as standing before her was the cutest thing she had seen in ages.

'Saul goes to St Cuthbert's on the other side of town,' he explained. 'He's a friend of a friend really but we like to hang out.'

Margaret found out that Saul was half British on his father's side and half Filipino on his mothers. 'That would explain his cute exotic look,' thought Margaret. Suddenly a plan was beginning to form.

Toby asked if Saul could stay for tea but Margaret made him phone his mother to tell her where he was saying she would run him home later.

Throughout the tea Margaret had a suspicion Saul was ogling her as she moved around. As usual she was wearing a tight shiny blouse that hugged her large chest, the top three buttons undone to reveal her magnificent cleavage, a tight dark grey pencil skirt and shiny sheer black nylons held up by a black satin girdle. Even in the house she wore shiny black high heel shoes. She'd caught him looking a couple of times which made him blush delightfully.

After tea Margaret asked Toby to tidy up and wash the dishes while she took Saul back home. On the drive she deliberately let her skirt ride up her thighs so that her suspender clasp and an inch of creamy white thigh were showing. She gleaned that Saul had just turned eighteen and lived with his mother after his dad had left when he was five.

Margaret pulled up outside his house and turned towards him, placing a hand on his thigh. 'I do hope to see you again. Please feel free to come for tea more often,' she said. Saul looked at the formidable older woman then dropped his gaze one last time to her stocking thighs and stammered out a thank you. Margaret could have sworn she saw an outline of an erection in his jeans.

Saul had been round for tea a couple of more times since that first Saturday. On the last occasion Aunt Margaret had managed to almost bump into him as he left the upstairs bathroom. The fact that she was only wearing a shiny black half cup silk bra that pushed her breasts up, a black satin girdle with four suspenders on each thigh holding up shiny black silk stockings and her shiny black high heeled shoes may not have been a coincidence. 'Oh, sorry darling. I didn't think anyone was in there,' she apologised to a stunned young man.

Margaret decided that she would make a move on him when she drove him home that night.

Toby was again told to tidy up and get himself ready for bed. She smiled at him sweetly and Toby knew what that meant. Aunt Margaret also knew she was going to be horny as hell when she got back from dropping Saul off.

A mile before his home Margaret pulled over in a quiet lane. It was dark.

She turned towards a nervous Saul who thought he was going to be admonished for looking at her in her underwear.

'Did you like what you saw earlier?' she asked the young boy. Saul just sat frozen and remained silent. Margaret took hold of his face and looked him straight in the eyes. 'Well did you?' she asked again.

Saul very slightly nodded his head. 'Good.' said Margaret as she leaned forward and gently kissed him on the mouth.

'So you like mature women in their sexy underwear, do you? asked Margaret as she placed her hand on Saul's crotch and found his cock hard. 'Maybe next time I'll let you see my naked breasts.' As she said this she gently rubbed the length of his cock through his jeans. Saul began to shake and pant. Margaret knew he was about to cum.

'Maybe you like dominant older women in sexy underwear? She said as she rubbed faster and harder. 'Maybe I should take you in hand!'

As she said this Saul came and flooded his pants with his cum.

'Toby is going camping at the weekend with his school. Meet me at eleven o'clock on Saturday outside Boots on the High Street. When I pull up jump in the car. Do you understand?

Saul stammered out a feeble 'ye...yes.'

'If you don't show up you'll never know what a dominant mature woman will do to you.'

When finally she pulled up at his house she smiled and reminded him to be there on Saturday morning. Saul just said 'yes,' and walked away.

Margaret drove home quickly. She was so horny and she intended to fuck Toby hard and long.

On Saturday after Aunt Margaret had seen Toby off on his trip to camp she began to get ready to drive into town and see if Saul would be there. 'It would b a shame if he had cold feet,' she thought.

She'd already telephoned Julia to tell her she had found a playmate for her and to expect her before noon.

She looked in her drawers and wardrobe for something suitably dominant and sexy. She found a red rubber corset with suspenders for her red fishnet stockings. She decided not to wear a bra or panties and shimmied into a tight red dress that matched her red high heels. She looked conservative and smart.

It was a minute to eleven and she was pleasantly surprised to see Saul standing waiting for her all by himself.

She stopped and he jumped in the car.

'Hello darling,' she purred. 'Are you looking forward to your day?' Saul just nodded.

'Er...where are we going?' he asked when he noticed she wasn't driving in the direction of her home.

'We're going to meet a friend of mine. She's been looking for a young man of her own to play with. I think you'll like her,' said Margaret. Saul looked nervous.

'Don't worry darling, you'll love it. If you don't want to go back you don't have to.'

Margaret pulled up outside Julia's home just before noon. Julia looked out of the window when she heard the car and opened the front door, standing behind it. Margaret went in first closely followed by Saul. When she closed the door Saul could see what this other mature lady was wearing.

Julia was squeezed into a skin tight shiny black latex dress that came to just below her knees. She had on shiny black silk hold-up stockings and shiny black high heeled shoes. Her make up was immaculate and her bright red lips looked incredibly sexy.

'Hello,' she said holding her hand out for Saul to shake which he did gently. 'Oh I think we're going to have fun with you.'

Saul felt faint.

'Let's go into the sitting room at the back. It's more private there,' said Julia.

Saul watched as Julia led the way to the back room, her sexy arse wiggled in her tight latex dress.

Saul was followed by Margaret. Once in the room Saul was told to sit on the large sofa. 'No, not there, In the middle,' ordered Julia. Saul could see her hard nipples pressing an outline in her dress.

'Let's undress him shall we Margaret?' 'You take the top and I'll relieve him of his jeans.' Saul sat still as they took off his clothes. When he was naked he covered his genitals with his hands. Margaret slipped out of her dress to reveal her red rubber corset, fishnets and a very wet shaved pussy. Saul gasped. Both women sat either side of the boy and removed his hands from his now hard cock.

Taking his cock in her hand Julia began to slowly masturbate the boy. 'You like the thought of a mature woman dominating you, don't you?' she said.

Saul looked at her and was amazed how beautiful and dominant she looked. He could see her hard nipples pressing against the shiny fabric of her dress.

'Oh I think he loves mature dominant women, don't you Saul?' replied Margaret taking his cute young balls in her hand. He looked at Margaret with her large breasts on display and her sexy rubber corset.

He just sat there, not moving but grunting as the two older women abused him.

'Why don't we put him over our knees and spank him before we take him upstairs and rape him?' Margaret asked Julia as she plunged her nails into Saul's balls.

'Uurrrgghh' groaned Saul as his cum erupted and dripped down both ladies hands.

'Mmmm, I think he likes that idea,' said Julia. 'Get on your knees boy. It's time you learned how to eat pussy,'

Julia stood up and pulled Saul to his knees and forced his face between Margaret's spread thighs. 'Now lick where Margaret tells you and make her cum!'

Saul was educated on how to make older women orgasm by using his tongue. After Margaret was satisfied Julia pulled her tight latex dress up over her thighs to reveal a freshly shaved pussy. 'My turn,' she purred.

When both women were happy with his administrations Julia said, 'Why don't we take him upstairs and fuck him?'asked Julia.

'Actually,' said Margaret 'I brought him over for you. I must be going. Could you be a darling and run him home when you're done with him?'

Yes, yes of course,' replied a delighted Julia.

'Now be a good boy for Julia and I'll see you next week when you come over for tea,' said Margaret nonchalantly as she slipped back into her dress.

'Wait here,' ordered Julia as she said her goodbyes to Margaret.

'Right, what shall we do with you?' asked Julia on her return. 'Okay, follow me!' As she led him up to her bedroom.

'Lie down.' she ordered. She took four silk scarves and tied him spread eagle to the bed. She sat on the bed bedside him. Saul looked nervous.

'Do you know what I'm going to do to you?' Saul shook his head.

'I'm going to break you. I'm going to lash your cock then when it's nice and hard I'm going to fuck you. Then I will lash your balls until you are hard again and I'm going to teach you how to fuck me.'

Julia took out a small flogger and flicked it over his cock. 'Ooooh,' exclaimed Saul. The pain was slight but the excitement immense.

Julia kept lashing his cock and she could see it getting harder as his moans were getting louder. When it was really hard she straddled the young boy and sank down on his seven inch penis. The sight before her nearly made her cum. Saul looked so young and innocent as she rode him harder and harder to orgasm.

She untied him and got him on his hands and knees on the bed with his legs open so she could kneel behind him and lash his balls. His squeals really turned her on and she was soon on her back with her latex dress around her waist and her black silk stockings wrapped around Saul's back as she guided him to fuck her. For the next couple of hours they rutted. Saul came at least twice and Julia lost count at five.

They both showered and dressed, Julia pulling on some jogging bottoms and a t-shirt along with trainers.

On the drive to drop Saul off she quizzed him on how he was feeling. Not getting much return on her questions she thought that maybe it was a one off until he turned to her and asked if he could see her again. Julia was delighted and told him to arrange it through Margaret.

Margaret had Toby all to herself now and enjoyed her weekends when Saul wasn't there so she could play dress up in her PVC outfits and abuse her young nephew.

It was all going well until one day just after Julia had picked Saul up from their prearranged meeting place there was a knock on her door. Leaving Saul on the sofa in her sitting room she answered the door. Suddenly a woman pushed past her into the house.

'Where is he?' the women demanded. Julia recognised the dark haired woman as Saul's mother from the photos he'd shown her on his phone.

'Hello Lin,' said Julia calmly, 'So nice of you to pop by,'

'Where is my son you peadophile? I'm going to call the police.' said Saul's mother.

'Oh I wouldn't do that just yet. Come on in to the sitting room,' said Julia.

When his mother entered the room Saul just stared at his feet, not knowing what to do.

'Sit down.' ordered Julia and she was surprised when the woman sat on the sofa next to her son.

Julia took a good look at her. She was a petite women with dark straight hair to her shoulders. About five feet tall wearing a t-shirt and incredibly tight jeans with high heeled shoes. She was very attractive thought Julia, Big eyes, olive skin and pouting lips. 'Now I know where her son gets his looks from,' thought Julia.

'What have you done to my son?' Lin demanded. 'I'm calling the police.......'

'No you won't!' barked Julia back. Lin stared at the taller, older women as she stood over her, her hands on her hips.

Julia was dressed in a shiny tight black leather pencil skirt with a crisp white blouse that was just see through enough to show her black half cut bra. Shiny black stockings and shiny black high heeled shoes completed the outfit Lin began to get nervous.

'Who do you think you are coming into my house and shouting the odds. I know you won't want the police involved. I may have to tell them what I already know about you my dear lady!' stated Julia calmly.

Lin gulped and hung her head.

'It's not Lin Tomkins is it?' asked Julia. 'You never married Saul's father.'

'I thought you might try something like this. Maybe a spot of blackmail so I had a journalist friend look into your background. He has a fairly meaty file on you darling,' Julia went on. 'You are here in this country illegally aren't you?'

Lin tried to say something but she was cut off by Julia. 'You bought a false wedding certificate and applied for a National Insurance Number to allow you to work and claim single parent benefits. All illegal because you are an illegal immigrant. You would be jailed for fraud then deported if the police were to hear about you. That is why you won't be going to the police but you will do as you are told. Is that clear?'

A very subdued Lin meekly nodded her head. 'Stand up!' ordered Julia as she reached for her riding crop.

Slowly Lin got to her feet.

'Strip!

Lin looked aghast at Julia then to her son. 'No, I won't do that. I can't do....aarrgghh!' she cried as Julia brought the whip down on her plump denim clad bottom. 'Do it,' said Julia quietly but with menace.

Not looking at her son Lin slowly undressed. First she pulled off her t-shirt to show off her naked breasts. Her nipples were starting to harden thought Julia. Next she slipped off her shoes before unbuttoning her jeans and sliding them down and off. She stood wearing only a little pink silk thong. Julia was practically drooling at her near naked captive.

'Saul, take off your clothes please,' asked Julia.

Saul immediately obeyed. 'No, please. Don't make him.....aaarrgghh,' shrieked Lin as Julia's crop lashed out at her near naked bottom. 'Quiet!' hissed Julia.

'Saul, remove your mother's thong.'

As Saul took hold of his mother's panties Lin was too scared to say anything.

'Kneel over there Saul,' said Julia pointing to a space a couple of feet away.

She then turned to to Lin who had one arm across her breasts and another covering her crotch.

Julia tapped at her arms with her crop and said, 'behind your back!'

Hesitantly Lin put her hands behind her back. Julia could see the younger woman in all her glory. Perky breasts, flat stomach and a cleanly shaved pussy. Julia liked what she saw.

She stroked the crop over Lin's now hard nipples causing her to moan. The fact she was naked in front of a dominant older woman turned her on like never before.

Julia started to run the whip over her thighs then on the front of them. Lin automatically opened her legs, an act that wasn't lost on Julia who proceeded to move the whip between her open thighs rubbing it against the younger woman's pussy lips.

Lin moaned even louder as the crop moved tantalisingly over her prominent clitoris.

'You are mine now!' stated Julia. 'I own you. Do you understand?'

Lin nodded. 'I asked you a question,' said Julia thrusting the crop hard against Lin's pussy lips. 'Ye..yes,' gasped Lin. 'You own me.'

'Good girl, now sit back down.'

Julia then walked behind the sofa and holding both ends of the riding crop she looped it over Lin's throat. 'Saul, show your mother what I have taught you.' Saul nervously crawled over to where his mother was sitting and put his hands on her knees and prised her legs open. Julia pulled on the crop slightly to encourage Lin to allow him.

'No. Please don't. Oh God,' she moaned as Saul went to work on his mother's pussy. 'It's..it's not right.' she groaned as Saul slowly worked his way towards her throbbing clitoris. 'Oh God. Oh fuck,' she cried as her son sucked greedily on her clit.

Lin could feel her orgasm building and suddenly she grabbed Saul's head and pulled him hard onto her pussy as she fucked her own son's face. With a loud scream she came hard flooding Saul's mouth with her orgasm.

'Well well,' said Julia. 'I think you needed that.' Then looking at Saul's hard seven inch cock she said, 'I think your son needs to cum too. Saul, fuck your mother!'

Lin tried to struggle but Julia held her firm with the crop at her throat. Saul lay between his mother's thighs and slowly pushed his cock deep into her.

'Oh God no. Please Saul don't. Oh God.' she screamed as her son fucked her harder. Soon her legs were crossed over her young son's body as she bucked back on his pounding cock.

Julia took away the crop and with one hand began to play with Lin's hard nipples causing her to shudder and groan as she was being fucked.

With her other hand she placed it on Lin's chin and lifted up her face so she could kiss her hard slipping her tongue into the young woman's mouth. Julia was pleasantly surprised when Lin returned the kiss.

'I..I'm going to cum Miss,' gasped Saul. 'Come in your mother then boy. Shoot your young juices deep into her pussy,' ordered Julia. Hearing that took Lin over the edge and as she orgasmed her tight pussy milked her son's cock as he fired off inside her.

'Now you two have had your fun I think it's my turn. Follow me.' said Julia as she led them up to her bedroom.

For the rest of the afternoon Saul fucked Julia who was in turn licked to orgasm by Lin. Julia fucked Lin doggy style with her strap-on while Lin sucked her son.

When Julia finally dropped them off at Lin's house Julia reminded Lin that whenever she wanted her Lin was to do as requested. Lin meekly agreed.

Over at Aunt Margaret's house she casually asked Toby if Saul was coming for tea. 'No, he said he had something to do,' replied Toby. 'Oh good,' remarked Aunt Margaret, 'I'm sure I can think of something nice for us to do as well.'

An hour later Aunt Margaret called down the stairs for Toby.

'Yes Aunt Margaret?' he asked.

'Come up to my room please darling,' she shouted.

Toby climbed the stairs not knowing what was to happen to him.

He knocked on his aunt's bedroom door and was told to enter.

Inside Toby's jaw dropped. His aunt was dressed in a tight white PVC nurses uniform with white hold up stockings and white high heels.

'Ah, you must be Toby my next patient,' Aunt Margaret said. 'Why don't you undress so I can examine you?' Toby stripped off his clothes.

'Right, now be a good boy and slip up on the bed will you?' Toby lay back naked on the large bed.

He watched as his aunt snapped on a pair of white latex gloves.

She then tied Toby's wrists to the headboard of the bed before pouring massage oil onto her gloves.

'Let's see how you respond to stimulation shall we?' she said. She took Toby's now hard cock in her oily hands and slowly masturbated him. Toby groaned as she teasingly worked on his shaft before moving on to the bulbous head.