The Cruel Step-Mother Ch. 03

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Both Bob and Timmy are used again and again.
6k words
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Part 3 of the 3 part series

Updated 06/08/2023
Created 08/09/2017
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Croony
Croony
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'Good morning Timmy, how are you today? Did you sleep well?' asked Joanna, his step-mother as he walked into the kitchen.

Timmy felt like telling her he would have slept a lot better if her mother had let him sleep. Joanna's mother Jean had been to his room after they had all gone to bed complaining she was horny and needed Timmy to do something about it.

He did.

Just then his Nan walked in and said good morning to her daughter. She turned to Timmy and said, 'Good morning stud!'

'Ha ha. I thought he looked a little tired. Did you wear him out Mum?'

Jean just smiled at her daughter and thought she should change the subject.

'Is Bob up yet?'

Joanna laughed and said something about him being tied up at the moment.

Jean excused herself and said she'd left something in the bedroom that she needed.

Timmy looked over at his step-mother and he could feel his cock start to stir. She was wearing a long silver silk dressing gown over her obviously naked body as he could see her erect nipples were poking through the tight shiny garment. On her feet were a pair of silver high heel slippers.

'What do you fancy Timmy?'

The question brought him out of his daydream but he just stared at her.

'Earth to Timmy, I asked what you fancied for breakfast.'

'Oh. Oh sorry. I'm not with it this morning.' he replied.

She walked towards him and held open her arms to hug him. He groaned as her huge breasts wobbled making his cock even harder.

'Was Nanny too much for you last night, darling?'

Just then she took hold of him and brought him to her for a close hug. Being taller than him his head was at the level of her breasts.

As she pulled his face into her cleavage she moved her hips towards his crotch.

'Oh Timmy, you are a naughty boy,' she cheekily scolded him.

He tried to move back from her but she placed a hand on his shorts covered buttocks and held him tight so his cock rubbed against her pussy that was now starting to get moist.

Upstairs Jean had found Bob as she had expected to, tied to the bed with a vibrating butt plug shoved up his arse and his stiff cock leaking pre cum.

'Well well son-in-law, isn't that a sight for sore eyes?'

Bob squirmed as his mother-in-law walked towards him shrugging off her robe to reveal a black see through baby doll nightie.

'Just what I need for breakfast,' she added.

'But Jean, what about Joanna? She'll be up in a minute.'

'Oh I wouldn't worry about her. She's in the kitchen with Timmy and by the look in her eyes and the bulge in his shorts she may be a while.'

Bob groaned at the thought of what his sexy wife would be doing to his son.

Jean bent over the bed and took Bob's hard cock into her mouth.

'Mmmm I think it's already hard enough for me!' she said as she climbed onto the bed and straddled his thighs.

She took his cock in her hand and rubbed it between her soaking wet pussy lips before slowly sinking down on it savouring every inch as it slid in.

'Oh my God Jean,' he groaned.

'Now you just relax and let me fuck you,' said his sixty one year old mother-in-law as she humped his cock before starting to ride him.

'Oh Bob, I love your cock. It's just as nice as your son's was last night.'

Bob groaned when he realised that he and his son were just sexual playthings to them and their family as he remembered what her other daughter and her granddaughter had done to them when they stayed a couple of months ago.

Jean could feel her orgasm brewing so she rode him faster and faster.

Bob knew he wasn't far off as the butt plug vibrated away in his arse.

'Oh God yes. I'm cumming Bob. I'm cumming!' she shrieked as she convulsed taking him over the edge as the both came together.

Downstairs Joanna had her step-son naked on his back and was sitting on his face just having enjoyed her second orgasm.

'I need you to fuck me now darling,' she told him as she climbed off his face and laid down on her back.

Timmy knew there was no way he could have argued with her so he assumed his position between her thighs and waited for his step-mother to grab his erect cock and guide him into her sopping wet cunt.

'Oh fuck!' he cried as he slid all the way in to her.

Joanna wrapped her legs over his back and ordered him to fuck her hard.

They rutted on the kitchen floor until both felt their orgasms building.

'So close baby. Keep on fucking Mummy. That's it baby boy make Mummy cum. Oh God yes. Give it to me. Fill Mummy up with your young seed. Yes!'

This made Timmy lose control and as he grunted he spurted ropes and ropes of hot cum into her grasping pussy.

Joanna got up, washed her hands, put on her gown and was just about to go back upstairs when her mother re-entered the kitchen.

'Did you find what you needed?' Joanna asked her mother.

'Oh yes!' she answered with a satisfied smile.

When Joanna entered her bedroom the smell of sex laboured in the air and the sight of Bob's limp cock lolling on his thigh proved that indeed her mother had found what she needed.

At dinner that night Jean looked over at Timmy.

'Darling I was talking to Judith this afternoon on the phone and she wanted to know if you would like to go up to Southwold to stay for a week. It's a lovely cottage, a couple of minutes walk from the sea and as it's your Summer holidays she thought you would like to visit. Joanna doesn't mind and I'm sure your Dad wouldn't. What do you say?'

Timmy looked over at his Dad who just nodded.

'I'll drive you up on Saturday morning darling. It only about a two and a half hour journey so I can come back home later that afternoon,' added his step-mother.

Timmy thought about seeing Zoe again and readily agreed.

On Saturday morning as Timmy was getting ready and his Dad was helping him pack Joanna and her mother were talking in the kitchen.

'I'm thinking about asking your cousin Julia to come and stay while Timmy is away. What do you think?' asked Jean.

'Will she bring Francis?'

'Oh yes. That would be half the fun, don't you think?' answered Jean.

Francis was Julia's young twenty two year old son who was at best camp if not a downright sissy. He was though bi-sexual and both Jean and Joanna had fucked him, as well as his own mother.

That afternoon Timmy found himself on his own with Judith.

'Zoe should be here by about six o'clock. She's out with some friends shopping in Lowestoft. Would you like to put your stuff away?'

Judith led him upstairs and into her bedroom.

'Where's my room?' asked Timmy.

'Oh, didn't you know? We only have two bedrooms here. I have one and Zoe has the other. We decided that can be in here with me one night and Zoe the next. You're going to need to keep your strength up.' she added with a giggle.

Zoe came home in time for a light dinner and gave Timmy a big hug and kiss.

Dinner was a quiet affair with Zoe telling them what she had bought in the shops.

'But I did by something special for Timmy's pleasure but I'll keep those a secret for now!'

When it was time for bed Zoe kissed Timmy on the cheek as she pinched his bottom whispering, 'Save some energy for me for tomorrow as you're going to need it.'

Timmy went for a shower and had just pulled on his bed shorts when he heard Judith shout she was going to have a quick shower too. Timmy climbed into bed and waited under the thin quilt for his step-mother's sister to join him. He was already hard.

Timmy gasped as Judith walked naked into the bedroom then climbed into bed.

'Timmy, what on Earth are you wearing? Take those silly shorts off at once. I need easy access to that cock this week.'

Timmy did as he was told and threw them towards a bedside chair.

'Oh good boy,' she said as she moved closer to him, putting her arm around his neck as she pulled him in for a passionate kiss while her other hand grasped his throbbing cock.

'Oh you are ready aren't you? But first I want you under the duvet.'

With that she pushed down on Timmy's shoulders and his head disappeared knowing full well what was required of him.

'Oh God, Timmy yes. Just there. Oh fuck. My sister and mother must have taught you well. Nearly there Timmy. Oh shit!' she chanted as she came all over his face.

After thirty seconds she ordered him up and on top as she opened her legs while searching for his cock.

Timmy slipped inside her with ease as she kicked off the duvet and wrapped her bare legs around his waist.

Timmy fucked her through three more orgasms before he came hard inside of her convulsing pussy.

On Sunday Jean looked out of the window when she heard a car door slam outside.

'Joanna, they're here!'

Bob sighed and made his way into the lounge to greet his guests. He heard a commotion of hugs and kisses in the hallway before footsteps coming nearer.

Jean entered first closely followed by whom he could only guess would be his wife's cousin Julia. They looked so much alike they could have been sisters. Tall, dark hair and a full figure

Behind her was her son, Francis. Bob almost looked twice to see if it wasn't a girl. He had shiny long black hair that fell down the side of his face and over his shoulders. He was tall and slim with the most beautiful face Bob had ever seen on a male. Francis had bright blue eyes, high cheek bones, a pert nose and the most sensual mouth he'd ever seen on a young man.

Bob had to make himself stop staring.

'Bob, this is my cousin Julia.'

'Hello Bob, nice to meet you,' Julia said as she reached in so Bob could kiss her cheek. 'This is my son Francis or Fran as he likes to be called.'

Fran stepped forward and held his limp hand for Bob to shake. Bob saw Fran's mouth open and his eyes go wide as he looked Bob up and down.

Bob felt a little nervous but he also felt his cock twitch.

'Are we in the same rooms as last time? I need to get cleaned up and deal with Francis as he was quite naughty on the way over. Bob, would you please bring up the bags and you can stay to watch the naughty boy's punishment.'

Bob did as he was told carrying the two cases up the stairs behind Julia and Fran. He admired the older woman's firm bottom but Fran's arse clad in tight shorts mesmerised him as the boy exaggerated the sway of his hips as he walked.

Bob deposited their bags and was about to leave when he was stopped.

'No, please stay. I want to show you what this little pervert does when I spank him. Also I saw how he looked at you when you were introduced. He should be more discreet and needs to learn some manners.'

'Strip!' was all his mother said and Bob marveled at the naked slim young man standing with his arms at his side waiting for his mother's next command. He could also see Fran's erect cock sticking out with an unusually large bulbous head. His cock seemed about six inches long but it wasn't particularly thick.

His mother sat on the side of he bed and pulled up the knee length grey skirt she was wearing to her waist then beckoned her son to go over her knee for his spanking. Bob's cock grew as her white suspender straps came into view holding up her grey stockings.

Bob then just stared at Fran's perfect white plump arse as it poised awaiting its punishment.

The spanks were rapid and were meted out on every inch of her son's alabaster skin. Bob was surprised that Fran wasn't screaming or shouting out for mercy. It seemed as if he was groaning and humping his mother's nylon covered thighs.

Suddenly Fran went stiff and let out a huge long groan as his cock erupted and shot rope after rope of cum along his mother's thighs.

'You dirty, disgusting little brat!' his mother chided then pushed him off her thighs. 'Crawl and apologise to Bob for being rude to him before!'

Bob froze as Fran came towards him on his knees then as he looked up at Bob he began to undo the belt on his jeans.

Soon Bob's jeans and underwear were round his ankles and Fran was stroking his thickening cock.

'I said apologise properly.' ordered his mother as Fran leaned in and took Bob's cock deep into his mouth.

Bob gasped as the young man's mouth worked wonders on him. He thought it felt like it had been slipped into a velvet plug socket.

Fran's soft lips went up and down on its length while his tongue swirled around its exposed head.

Bob didn't think he would last very long so when he looked over at Julia and saw her with three fingers sawing in and out of her pussy he lost it. He pulled Fran's face tight against his groin and erupted down the young man's throat.

He hurriedly pulled up his pants and jeans before making his way to the door. He paused to say something to Julia and was surprised to see Fran between his mother's thighs licking his cum from her stockings.

Julia looked at Bob. 'Don't worry dear. I'll be having your head between my thighs servicing me soon!' With that she pulled Fran's face into her pussy and groaned.

Bob made his way candidly downstairs.

That night in bed with his wife Joanna began quizzing him about Julia and Francis.

'What do you mean?' asked Bob trying to sound innocent

'Isn't Fran the most gorgeous young man you've ever seen?'

Bob said that we was quite charming, effeminate but charming.

'You do know he likes to fuck men as well as women, don't you?'

Bob replied that he didn't know what he did sexually, then remembered the fantastic blow job he'd had earlier that day from him.

'Bob? Is that your hard cock I can feel digging in my thigh?'

Bob kept quiet.

'Oh Bob, you'd better fuck me quick before he turns you.' she giggled.

Bob fucked his wife as hard as he had done for a long time but didn't know why he was so turned on. Joanna did.

In Southwold it was Timmy's turn to service Zoe. They'd had a nice day in the country with lunch at a quaint inn by a duck pond and spent the rest of the day relaxing in the garden then watching television until it was time for bed.

Zoe wasted no time in stripping him then mounting his hard cock. She came twice with her on top then they both came to shattering climaxes with Timmy pounding her from above.

She made him fuck her doggy style in the morning before they got up and showered.

Back in London the two guests with Joanna and Jean had gone sight-seeing leaving Bob at home. He tended to his chores and spent a lazy day in the back garden reading until it was time to make dinner.

Their guests were shattered by the time they got back so after dinner they decided to have an early night. Soon Jean said she was going up to read leaving Bob with his wife.

Yawning, Joanna told Bob she too was going to retire so Bob said he'd go along too.

Monday evening after a day out by the sea Timmy was in with Judith again.

This time when he came back from the bathroom she was lying on top of the bed wearing nothing other than a pair of black hold up nylon stockings and her black high heels.

'Oh Timmy, I'm feeling wanton tonight. Just come here and fuck me.'

Soon her stocking clad thighs were around his waist while the heels were digging into his arse, urging him to go faster and deeper.

Tuesday was a similar day for Timmy. A day by the sea and into bed with Zoe at night.

He thought he would be glad to get home for a rest.

Bob was once again left alone as the ladies and Fran went into town shopping.

That night because it was so warm they ate a salad for dinner. Nothing untoward occurred that evening either.

The next day Bob had to go along to his mini-mart to oversee a delivery. He arrived home late morning. After putting away the groceries he'd brought back with him he went into the lounge to see if anyone was around.

Sitting reading the daily newspaper was Julia.

'Everyone else gone out?' Bob asked.

'No, they've taken Fran upstairs for a bit of fun.' replied Julia standing up.

'Come along, let's go and see what they are up to!' she said.

She led Bob upstairs by the hand, Bob ogling his wife's cousin's arse in her tight black pencil skirt as she walked.

They stopped outside of Bob and Joanna's bedroom where the door was ajar. Peeping in Bob could see the young man, naked on his back with his wife sitting on his face and his mother-in-law stroking his cock.

'He can fuck you first, then by the time he's licked me to orgasm he'll have recovered enough to fuck me!' he heard his mother-in-law say. His cock was starting to get hard.

'Come along Bob. Let's go to my room. I do need a decent fat cock in me!'

She dragged Bob up to her room where she wasted no time in stripping him and then ordered him onto the bed where he stared at her as she removed her skirt to reveal a broad black satin suspender belt holding up her black nylons. Then she removed her blouse showing Bob her large breasts in a black satin bra which she quickly peeled off. Finally she stepped out of her black heels and peeled down her black satin panties before kicking them away.

Julia climbed onto the bed and pulled Bob towards her, cradling him her arms, his face inches from her breasts.

'Go on Bob, suckle on my large nipples. I love them being sucked'

Bob slurped and sucked on her large teats as his cock became even harder.

'Bob, Is that your cock I can feel digging in my thigh?'

Bob didn't answer but kept sucking as he nodded his head.

'In that case I think it's time you fucked me.' she said as she pushed Bob away from her and laid back with her legs open.

Bob was so turned on he quickly climbed between them and slid his cock in deep.

He kept up a steady pace as Julia writhed beneath him, her large breasts heaving with every thrust.

'Harder Bob, I'm close.'

Bob was pleased as he was close too and pounded her even harder.

'Oh fuck Bob, yes. That's it. Don't stop! For fucks sake don't stop!'

Bob could start to feel his balls tingling and he hoped she would cum quickly when he heard, 'Oh God yes!' as she stiffened under him and then he tensed before he flooded her pussy with his cum.

On Wednesday Timmy was resigned to fucking his step-mother's sister again that night and he didn't disappoint her either. Going down on her and bringing her to a quick orgasm he took her from behind before shooting his load into her squelching cunt.

Thursday was Julia and Fran's last full day before they left for home on Friday morning.

They all went out for a pub lunch then sat in the sun in the garden with a glass of wine.

Joanna excused herself and was away for ten minutes before rejoining everyone.

Then Julia and Fran disappeared but only Julia returned. Bob just sat in his lounger drinking his wine and having a snooze.

Suddenly his wife shook him and told him she needed him.

Bob followed her into the house then upstairs to their bedroom where Joanna proceeded to undress her him.

'Jo..Joanna, what are you doing?'

'Oh shush Darling. We're just going to have a bit of fun, that's all.'

Soon Bob was on his back and tied spreadeagled on their bed. Joanna masturbated him until he was hard and his cock was standing up straight.

'Won't be a moment Darling.' she told him as she opened the bedroom door before closing it and going up to her sister's room where Fran was waiting.

His mother had transformed him into a slut. He was wearing light blue eye shadow and pink lipstick with a leather mini skirt and a tight pink t-shirt. Oh his feet he wore pink heels and his legs were bare but oiled.

'Give me a couple of minutes to go downstairs and you can go in.' Joanna told him.

As she walked into the lounge the TV was already on.

'Is everything set up?' asked her mother.

'Yes, just let me get it on to the correct channel,' said her daughter just as the screen flickered to life and they saw the door to the bedroom slowly open.

'Hello Uncle Bob. Fancy finding you here!'

'Fran! What's going on? Where's Joanna?'

Fran sat down on the side of the bed facing Bob and crossed his legs. 'I thought I would pop in and see you as we're going home tomorrow.' Fran took hold of Bob's cock and slowly stroked it.

Croony
Croony
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