I don't own 8 Simple Rules. This a fantasy, not reality and the writer doesn't condone real life fucking with underage boys. It's good to read though...

If you like this story please e-mail me at [email protected]

8 Simple Rules: Cate's Dates Part 1 - Back On The Saddle With Josh (Fb)
by Neenah

Cate Hennessy looked in the mirror, brushing back a strand of dark hair. She looked better than a woman of forty-eight should, retaining her slender figure and with less excess fat than many of her contemporaries. Her face had not yet begun to line too much and neither her ass or boobs were sagging so much that some exercise and staying away from sugary drinks couldn't keep under control. She looked at her clothes, a pair of jeans tighter than they should be and a tight orange top which fitted snugly over her large boobs. She was made up as well, her lips red and her eyes highlighted.

She looked sexy she knew, it felt wrong. She took a step away from her mirror and turned round to take off the sweater and go for something more baggy.

Her daughter Bridget knew exactly what her Mom was doing, "Don't even think of changing, you look fab."

"I'm not sure, is it appropriate?" Cate said worriedly.

"You're going on a date, it's appropriate to look fab," Bridget smiled.

"Is it appropriate to be going on a date though?" Cate asked.

Her daughter sighed, "Yes, Dad's been dead six months, you need to get back on the horse and ride again and start going on dates. Anyway you were the one flirting."

"I wasn't flirting, I was talking to him. He delivers our paper every morning. I was just been polite," Cate said defensively.

"Half-naked under your robe, whilst twisting a finger sexily in your hair and giggling like a teen schoolgirl and I should know, I am one."

"I wasn't to know you were going to get his number," Cate said.

"If I didn't you weren't," Bridget beamed, knowing she was right.

"I would have... sometime," her Mom blushed, knowing it was probably true. It had taken all Bridget's pleading, supported by her other daughter and son for Cate to pick up the phone. "I still think something else."

"Too late," Bridget said as the doorbell rang. "He's here."

For a second Cate felt a moment of brief panic, it had been so long since she'd be on a date. She fought it down, it was too late for nerves. She gave one last look in the mirror, just to confirm her daughter's opinion that she looked fab. She went down the stairs and took a deep breath, before exhaling and opening the door with a smile.

Her date, Josh, was standing there a big bunch of flowers in his hands, looking almost as nervous as she felt. Somehow they made her feel better. He was in smart slacks and shirt, the top button unbuttoned, with his dark hair less shaggy than when she'd seen him last, but still half way down his collar. He gave a nervous smile, showing a small gap between otherwise perfect teeth and held out the flowers, "For you," he nearly stammered.

Cate took them and looked at the woman behind Josh. The family resemblance was obvious. She held the flowers in one hand whilst holding out the hand to Josh's Mom, "You must be Mrs Jennings."

"Please call me Marcia," the woman said smiling cheerfully as she shook Cate's hand. If she was a little plumper and older than Cate had imagined she sounded exactly as she had on the phone, whilst it was no-longer illegal for older woman to date twelve year old boys (or even younger) not all Moms were relaxed about their sons being with women their own age or even older and once she'd ascertained that Josh would love going out on a date with her she'd wanted to speak to Marcia Jennings to make sure his Mom was happy. Marcia was. She was a divorcee herself and as she'd told Cate had had a number of much younger lovers since she and her husband had split.

"Come in a moment, let me put these in water," said Cate. She gestured to her daughter Bridget half hanging over the banister in interest. "This my daughter, Bridget."

"Hi," said Josh shyly, whilst his Mom said the same more confidently.

"I'll just put these in a vase. I've got one in the kitchen," Cate said.

Marcia Jennings looked at her son, "Why don't you wait here a moment, whilst I have word with Cate."

The two older women went into the kitchen. "Are you sure you don't want to chaperone on the first date?" Cate knew that some Moms liked to come along on the first date to make sure their sons weren't going to be kidnapped and sold into slavery.

Marcia shook her head, "No, I wouldn't want to be a third wheel. I'd just spoil your fun."

Cate was still nervous and would have welcomed the other woman along, but she just smiled like she was relieved.

Marcia carried on, "I'd like him home by nine, like we agreed." Then she smiled, "Though if the dates gone well he doesn't have to come home alone, if you know what I mean."

Cate put the flowers in the vase and smiled, "Yes."

"Well I better get going, I've left my younger son in the car. You two have fun and I'll see you later." Marcia went into the main room, kissed her son tenderly on the head, said goodbye to Bridget and left.

Cate smiled at her date, sitting nervously on the sofa and picked up her purse, "Are you ready to go now?"

Josh nodded and stood up, smoothing his pants nervously. Cate reached out to take his hand. He seemed a little surprised and nervous.

"Have a good time," called Bridget as Cate led Josh to the car.

"I thought we'd eat first," said Cate as the young boy got in and put on his seatbelt, a little unsure about sitting in the front seat until Cate opened the door.

"OK," he nodded, "Where?"

Cate had thought long and hard about this. She knew lots of lovely eateries, with secluded tables and romantic candles on the table. But that was great if she'd be going on a date with a man her age, she didn't think a twelve year old would appreciate it so much. "I thought Besty Burgers, if that's OK with you."

Josh nodded and smiled happily, "I love burgers."

"That's good, order what you want and after we can have an ice-cream as well."

Josh smiled happily, "Great." He looked out the window for a second and then turned to Cate, looking anxious again, "This is my first date."

No wonder he had butterflies. She gave him a reassuring smile, "It's been a long time for me, so long this is almost like a first date. So let's both just relax and enjoy it."


He still sounded nervous so Cate led with an easy question about school and by the time they parked in the Mall Parking Lot, he was much more relaxed. When Cate offered her hand he took it without hesitation and they entered the Mall, walking along hand in hand, like other dating couples and then up to the Burger joint. Standing in the queue Cate looked down at Josh, "What would you like?"

"I'd like a whopper and fries," he said.

"I'd like a whopper as well," she looked down at him and blushed as he giggled when they both realized what she'd said. He squeezed her hand, which she did think was promising. She squeezed it back, running a thumb gently over the back of it. She looked at the board again, "What do you want to drink?"

"Strawberry Milk Shake," he said.

"Shall we make it a King Size and we can share?" she asked and he nodded, as she ordered it and two straws. Then they ordered a couple of small tubs of ice-cream.

They found a little booth and sat down opposite each other. Josh had got over his nerves and happily told Cate about his favorite TV programs and computer games as they ate their burgers. She waited until he put his straw into the drink to lean forward and do the same, so their faces were just inches away from each other. He giggled and smiled through the straw and Cate beamed back, thinking he was even cuter close up.

They continued to talk, Josh telling her his favorite joke and her doing the same back, before very briefly talking about her marriage before moving on to talk about his last vacation and what he had planned for the next one. As he opened his ice-cream his foot moved and gently brushed against Cate's inner calve, it could have been an accident but she hoped not. She opened the ice-cream. "Want to try some of mine?" she cooed sexily, taking a lump on the plastic spoon.

"Only if you try some of mine," he replied back, spooning out a chunk.

They both smiled and giggled as they slid the spoon into each other's mouths and then did it again, several times so that they ate as much of the other's ice-cream as their own. The date was going well thought Cate as she put the empty wrappers and cartons on a tray and stood up. "I thought I'd give you a choice, for where we go next, we can either go the new gallery across town and see some paintings," she paused as his face momentarily fell. "or we can go and play laser-tag."

"Laser-tag," he laughed and it was he who held out his hand for her to take.

They entered the laser tag arena and kitted up. Cate had never played before, but had taken some hints from her son, Rory. Soon she was running around in partnership with Josh, shouting 'Cover me' and 'Behind you' as they zapped other teams. It wasn't really her thing, but it was fun enough, especially when she was behind Josh and could see his buns under his slacks; they were cute and sexy and she wondered what they'd be like to grip when his pants were off. She shot another young girl and followed Josh round a block. He had dropped down behind it and she followed him, dropping down on the floor beside him and stretching her legs out as she got her breath back.

It took her a few seconds to do so, it was exhausting. When she had she turned his head towards him to look into his eyes. "Having fun?" she asked.

"He nodded, "Yes, fab fun."

There was a pause as across the room the other taggers shouted and hooted and shot each other, as Cate and Josh sat in comparative peace in the corner. They leaned together for a moment and their lips met, briefly moving against each other as their mouths opened. Then there was the sound of running footsteps coming towards them and the moment passed as both Cate and Josh stood up to take a shot. The kiss might have been brief but to Cate it was confirmation of how well the date was going and as she ran for a new piece of cover, she was hoping that Josh was enjoying the view of her buns as much as she had enjoyed his.

They played a few more games of tag, but didn't get another opportunity like it. Though as Josh seemed to have enjoyed it Cate didn't think the time was wasted. She looked at her watch, "We've got time for a Cotton Candy before I take you home if you want?"

He nodded, "Yes please. Let's share it."

They walked to the outside of the Mall to where the small trailer was parked which sold the Candy and Cate got a large one for them to share. They sat at one of the tables outside, in the warmth of the evening, and ate the Candy - one handed, as there other hands were stretched against the table holding each other's as they talked and ate. Josh's foot was stroking Cate's leg and she knew it wasn't an accident. He was so cute.

She held off going as long as she could, but she didn't want to be late - not if she wanted Marcia to let her have another date with Josh. She was pleased that when he said they had to go he gave a long drawn out 'Aaaawww' and looked as disappointed as she was.

They arrived outside his house a few minutes before 9. Marcia was looking out the curtains, seeing Cate pull into the drive she waved and them closed them to allow them some privacy for the remaining few minutes. Cate unclipped her seatbelt and Josh did the same, both half-turning to face each other. "I had a great time," Cate said and she wasn't lying, it had been such a fun date she wondered why she had been nervous.

"I have as well, the best," Josh said.

They leaned together again, their mouths opening as their lips pressed. This time there was no interruptions and Cate allowed herself to wallow in the kiss, her mouth up and down over her dates, as her tongue joined in. Her hands moved down, one to stroke his side, the other onto his thigh. As they carried on kissing, Cate's second hand went up the thigh until she got to his nether regions. She was pleasantly surprised by the size of the mound she encountered, her hand moving over the lump, rubbing it with her palm, sensing the tremble of what seemed to be a mighty python. She kept her hand there for the remainder of the kiss, until they pulled back. The time on her car clock was 21:05.

"This has been a great date," she repeated again.

Josh smiled at her, "It doesn't have to end yet, you could come up and take a look at my bedroom."

Cate hoped that was an euphemism , but even if it wasn't it was a way of prolonging the fantastic date. "I'd like that."

They held hands as they entered the house. Josh's younger brother briefly turned from the TV as they entered before returning to it. Marcia was up and smiling. "I can see you had a good time."

"The best," Josh said and looked at Cate with a look that melted her heart with lust. His hand went to her ass, resting on the round butts and gently stroking his fingers down and across it. "I was just going to show Cate my bedroom."

His Mom smiled, knowing exactly what was going on, "Would you like some milk and cookies? I'll leave them outside, I wouldn't want to interrupt you."

Josh looked at Cate and she nodded, so he said to his Mom, "That would be great."

"I might see you later," Marcia smiled as Josh guided Cate towards the stairs.

"We'll see," grinned Josh and Cate just smiled knowingly.

Josh's room was the final one on the landing. A huge poster of a skull and crossbones emblazoned the door with a red 'Keep Out' underneath. Josh saw her looking at and gave a small smile, "I'll make an exception for you."

He opened the door and Cate wiggled in, swinging her ass seductively. It was a typical boy's room, even with some clothes strewn on the floor from when he'd changed before their date. Posters of cars and planes adorned the wall, leaving hardly a spare space, model aircraft hung down on slender wires and Star Wars models, Transformers and dinosaurs covered every spare space on his shelves and cupboards; the only surface they didn't cover was his desk with the computer and monitor on it. Cate walked over to his bed, a quilt of Superman covering it and sat down. "I like your room, very you."

Josh sat down next to her, "Mom says it could do with a tidy."

"OK, I shouldn't contradict your Mom. But then she's looking at you as a son, to me you're a hot date, so I want to flatter you," she smiled seductively.

"You don't have to. I mean you can, but you don't have to," his hand went to her leg and he rubbed his palm over it, the denim so tight that she could feel the tingle of it as he slid up and down.

They began to kiss again, mouths opening and closing together, tongues slipping against each other. They rolled properly onto the bed, so they were lying down, half across and half opposite each other, their legs wrapping together and their hands sliding up and down each other's bodies. Cate unbuttoned a couple of his shirt buttons and slid her hand inside to stroke his smooth boyish skin. She didn't want to go too fast for Josh or push him further than he wanted to go, but at the same time she did want to make clear that she was happy for it to do so. He took the hint and his small, young hand came up and began to grope a boob under her orange sweater. Her mouth continued on his and her hand rubbed his chest for a few more moments, before undoing the rest of his shirt. All the time his hand was playing with her tit.

"If I take off my top, will you take of yours," she said.

"Deal," Josh replied.

Cate sat up and pulled her sweater over her head. Her large tits were free and bouncy. An equally topless Josh, his chest smooth and hairless, looked at them lustfully. "Shall we carry on kissing?" he said.

"Yes," giggled Cate, lying down and rolling over towards him. Her hand moved to his chest as before and his to hers. Except this time there was no sweater in the way and his hand could paw her boob direct, squeezing and groping it, his fingers digging into the massive mammary as his palm grazed over her solid nub. Cate kissed him hungrily, enjoying not just his hand but his mouth and tongue as well, for a boy on his first date he was a gifted amateur.

She moved her hand from his chest and down below to his naughty bit. There was a major lump there and she ran her hand over it seductively, Josh carried on kissing her, not put off by her fondling his dick. She decided to chance her arm and her fingers found the button of his slack and unbuttoned it. His reaction was to move his hand from her breast and move it down to the top of her jeans and pop open her button. Cate giggled and stop kissing to look him in the eye as she found his zip and slowly pulled it down. He smiled back at her, his fingers working down her jean buttons undoing them one by one. Her hand slid into his flap and her fingers stroked the massive schlong underneath. He returned the favor, slipping under her panties and running a finger over her waiting hole.

"Do you want to take our pants off now?" he said.

"Do you want too?" Cate tittered sexily.

"Yes," he said strongly.

"Me too," Cate said.

The two of them stood up and reached for the top of their pants. Cate bending over as she pulled hers down and temporarily Josh went out of her eyesight. When she straightened she saw he'd not only got rid of his slacks but his underwear as well and was standing there in just his socks with one of the biggest erections that Cate had ever seen. Ten inches of throbbing muscle as thick as his wrist. He smiled, "I thought I'd take off my boxers as well."

"I feel overdressed," tittered Cate and removed her own panties to show her pussy to her date as he quickly sat down and removed his socks, jumping onto the bed to lie on his side facing her. She did the same, so they were both totally naked, then she got on the bed opposite him.

They began to kiss again, even more intense than before, Josh half rolling onto Cate so that he was on top of her, one boyish hand playing with a boob, the other stroking down at her funhole. Cate stroked his cock in return, it was so big and hard, and the thought of it in her was exciting and made her cunt slick with lustful thoughts and desires. Josh moved further onto her, his mouth on hers and his small, smooth chest resting across her tits as his large schlong stroked her thigh. Unable to grip the dick properly Cate, began to stroke her pussy in time with Josh, her other hand down his back to touch his bottom.

He lifted his mouth from hers and looked into her eyes, "Can I have sex with you?" for a moment his nervousness had returned

"Yes, stick that big boy in me," Cate said enthusiastically.

He entered her and for the first time she had a twelve year old boy in her, even if he was one with a whopper men twice his age would have envied. It was so big and weighty it stretched her and she could feel it moving down her wet hole. She groaned and reached round his back, grabbing his shoulders as her rose and holding on. He slammed down, his schlong shooting into her hole and his head falling between his massive, jumping, titty-mounds. He placed his hands either side of her and ratcheted up and down, his oversized prong pounding down. She gasped in bliss as he filled her with dickly joy, the huge schlong going deeper into her that any member she could remember. His head fell between her tits again, his hair brushing at the melons. She squeaked and squealed, her legs crushing at his sides as he moved in.

"Oh, oh, oh," Cate cried out, her body filled with sensations of bliss. He went fast and deep, humping at her and sending his meat far into her juicy pussy. She held him, tight and close, encouraging his more than manly thrusts. More bliss boiled in her as he went down, his slim body banging against her older one. Her boobs bounced and swung as his head dipped between them, beads of sweat coming from him as he went faster and further.

"Oohhh, ooohh," she cried, even more loudly, so the whole house could hear her cum. "OOohh, ooohhh," the orgasm was intense and powerful. "OOoooohhhh."

He groaned as well, "I'm going to cum."

"Shoot it in me, baby," Cate grunted.

His back straightened and his eyes widened and his mouth opened as he unloaded his cum into her pussy, exploding what seemed like buckets of the sticky white semen into her hole, flooding it with cum, so it dribbled out as his cock slipped out.

"Oh," Cate moaned lying back, "That was fantastic."

"I know, you're so sexy, it was brilliant, banging you," Josh nodded, sitting up and wiping a strand of hair from his sweaty forehead. He stood up, his cock swinging - it was large even when limp and stretched, "I wonder if Mom brought up the milk and cookies? Do you want a snack?"

"Yes," Cate dragged herself to sit up and lean against the wall as he date padded across the room and opened his bedroom door. There was a tray with the milk and cookies outside, Marcia Jennings must have dropped it off when her son was boning her, as Cate hadn't heard her. The boy picked it up and brought it in, laying it on the bed and then getting on it and crossing his legs.

They drank the milk, slightly warm and ate the cookies, delicious, talking as they did so and getting to know each other better as was the norm on dates.

Finished he put the tray on a bedside cabinet, pushing aside some Star Wars models to fit it on. Cate looked at the clock, it was getting late, "I should be going soon," she said.

"Don't you want to stay for a little longer," he said uncrossing his legs and straightening them. His hand slid to his dick and he rubbed it, bringing it slowly to life as she watched.

Cate giggled, "Don't you have school tomorrow?"

"Yes, but I'm not tired yet," he smiled charmingly.

Cate looked at the clock again, she had to admit her own funhole was aching for some huge dong and Josh could supply it. She smiled and pushed him onto his back, "OK, I can stay a little longer, but if you're tired tomorrow don't blame me."

"I won't be," he grinned.

"Well to help you keep your energy, I'll do the work this time," tittered Cate. She moved to straddle him, taking his huge whopper in her hand and guiding it into her waiting tunnel. It pushed up, exciting her with its girth. She pushed down, enjoying the feel of the huge member penetrating her, throbbing as it went up her slick, slippery tunnel. "Oh," she moaned with feeling as she came all the way down.

"You're so hot," he breathed lying back his hands lying out by his side.

"You're so cute," Cate breathed back, she placed her hands beside him using them to lever herself up and down the humongous dong. She started slow and then began to go faster, her boobs bouncing over his face as she jumped. He looked at the huge swinging mammaries with admiration, licking his lips and placing his hands on hers. Cate smiled back down at his, admiring his cute, slim, sexy body, his cute boy like features, but most of all his massive man sized meat, which she hammered down.

She went faster, zooming up and down the huge schlong, driving herself and it to new heights of excitement. "Ohhh," she moaned loudly, her body belting down. The bed banged and squeaked and her moans were even louder, filling the room and probably the ones nearby. "Oooohhh."

Below her Josh was panting even though he wasn't putting in nearly as much effort as her. She swung herself down hard, pounding his cock. Perspiration slid down her and her breath came in starts and stops. But she didn't care, all she wanted was prick and his member was fulfilling that need. She drove herself faster and faster, cumming loudly and continuing.

Until Josh's eyes widened and his mouth opened, he let out a series of guttural grunts and for the second time flooded Cate's cunt with cum, the goo exploding upwards and then leaking downwards over her lips and dripping down from her funhole as she lifted herself.

"That was as good as before," Josh grinned.

"Maybe even better," Cate said. She glanced at the clock, regretfully deciding she really did have to leave if she wanted to remain in his Mom's good graces and allow him some time to sleep. "I better go" she said and stood up. His eyes followed her as she wandered naked round the room, picking up her clothes before positioning herself where he could easily see her as she got dressed.

Once dressed she leant over him and gave him a long, slow kiss. "I really enjoyed our date."

"Me too," he smiled.

"I'll give you a call if you want to do it again."

He nodded, "Yes."

Marcia was just tidying up the kitchen when Cate came downstairs. Josh's Mom smiled at Cate, "It sounded like the two of you were having fun."

"Josh's has got a great collection of toy spacemen," Cate giggled. Then she put on a more serious face, "I hope we weren't too loud and disturb your other boy or you."

Marcia shook her head, "I've had younger lovers myself, I know what they do to you."

"Josh certainly made me cum," Cate said. "I was hoping to give a ring and set up another date, as we so enjoyed this one."

"You should do, I'm sure Josh would love another date," Marcia said.

* * *

The lights were on when she got home and she opened the door three expectant faces looked at her.

"You're late," said Bridget so innocently she didn't mean it.

"How did the date with Josh go?" asked Kerry

"Did you follow my suggestion and take him to laser tag?" Rory asked.

"The date went well, I took him to laser tag and I'm late because after I took him home he wanted to show me his bedroom," she smiled as her three children gave small whoops of admiration, all three were very supportive of her dating again, which was good, otherwise she doubted she would have the courage to call Josh the first time.

"He showed you his room on the first date? Naughty Mom," said Kerry smiling to show she got the euphemism.

"So how many times?" grinned Bridget, also understanding the euphemism.

Cate held up two fingers, "Twice."

"Way to go Mom," Rory grinned, "So you seeing him again?"

"We'll see," said Cate, her mind going back to her date's hot swinging python. She smiled, "We'll see."


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