Mother’s Helping Hand Ch. 17

Anal

The usual disclaimers apply, the story contains incest and sexual scenes so if you are likely to be offended by this please don’t read any further. The characters are over 18, the persons and events described are entirely fictional. The author reserves all rights to the story and its reproduction with the exception of Literotica. All feedback is appreciated and if you like the story, please rate it in the comments section.

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After they had cleaned up, Bobby and Alison were so tired they went back to bed. Alison fell asleep quickly with the effects of the alcohol; and Bobby lay awake thinking about what had happened. Twice in one morning he had slid his cock into his mother’s tight pussy, first by accident…and then by design. The image of his mother lowering herself onto him inch by inch, before he buried himself to the hilt, replayed in his mind, the feeling of her warm wet pussy cumming on his cock vivid, as if he was experiencing it again. He could feel himself getting hard, and sensed that a boundary had been crossed. Surely, now that she had climbed on him once, she wouldn’t deny him a repeat performance? She couldn’t deny she wanted it as well. Her arousal was obvious, her orgasm while he was buried inside her proof enough of that. The thought of fucking her and watching her cum seemed almost too exciting to bear, he imagined pounding her while her big tits swung around as he drifted off to sleep.

The morning’s excitement had taken its toll on them both; and they sleep through ’till the afternoon. Bobby awoke first and looked over at his beautiful mother. She had pushed the sheets off and lay with her back to him. He looked at her curvy peach-like bottom and felt a rush of excitement; as he could make out her puffy pussy lips peeking through. His cock lurched as he remembered the feeling of being buried inside her, and her pussy spasming on him as she came. What would she think if he slid into her now, he wondered?

God, how good it would feel to slip back inside that wonderfully tight, slippery tunnel. How would she react? Would she freak out, or would she surrender to the pleasure? Would she push back onto him, encouraging him to feed her more of his cock, greedily consuming his huge shaft? Would she start gently rocking on him as she had before; and if he responded by gently sliding in and out, would she complain or allow him to continue, until he was sliding a few inches, and finally the whole length, in and out of her? His dick spasmed again; and he idly reached down and stroked his cock, as he imagined his hard dick slamming in and out of his beautiful mother. God, that would feel so good. He wondered how long he could keep from cumming. And when he needed to, then what? Would she push him away, tell him to shoot his load over her ass, or would she want him to carry on, to fill her with his seed?

He stroked his cock as he imagined pumping his load into her, and felt a dribble of pre-cum run down the head. His thoughts were interrupted as he felt his mother begin to stir.

“Mmmmmfff, oh dear, what time is it?” She yawned as she rolled over and stretched, her big tits thrusting out as she did.

“Um, nearly 6pm, you were out for a while.”

“Six?? Goodness, I’ve slept the whole day away!”

“Well, I guess you were tired.”

“Mmmm, well, gin and tonics for breakfast didn’t really help,” she remarked ruefully.

“How long have you been up?” She glanced at his cock, which was throbbing, peering back at her with its evil eye, and flushed. “I mean awake.”

“Not long, just a little before you. How are you?”

“A little sleepy. That’s all.”

“No I mean, after… this morning?”

“Oh…that.” She paused, remembering the events and considering. “Well, aside from feeling like some of my internal organs have been moved about, the sky hasn’t fallen in; and we’ve not been struck down by lightning… so I suppose I’m ok.”

His dick jumped. If she was ok, did that mean a repeat performance was in the cards?

“Bobby, this trip… I wanted it to be closure. I wanted us to be able to get back to some kind of normality again.”

Uh oh, where was this going? Every time she started talking about being normal, it led to a set of blue balls for Bobby.

“I’m not sure what normal even is anymore; but do you think we can we just try to be like mother and son for an evening?”

This wasn’t sounding good; but he figured it was best not to force things.

“Sure, I’m always your son, you know that.”

“I know but…” She looked down at her and Bobby, lying naked in bed with Bobby’s erection glaring back her. How could she have been so stupid as to get herself into this.

“Look, can we go out to dinner, at one of the restaurants in the non- nude zones? I just want to have an evening with my son without having everyone staring at us.”

“Staring at us?”

“Well, at… that.” She regarded his cock.

“Oh, do they?”

“Bobby, don’t play dumb. Of course they do, they could hardly miss it, especially when it seems to be permanently erect.”

“Well I thought halkalı bdsm escort they were looking at you, I mean you’re not exactly hard on the eyes Mom.”

“If you mean men staring at my boobs, I’m used to that. I’ve had to put up with it all my life practically.”

“I didn’t mean just that, I mean you are beautiful.”

She smiled and blushed.

“Oh Bobby, just like your father.”

They looked at one another for a moment; and he knew he would never love another woman the way he loved Alison. If she wanted a normal meal she would have one. His hard on would just have to wait.

They showered and dressed, Bobby wearing his suit that he knew his mother liked; and she wore a white dress that showed off the tan she had started to get. It was relatively modest; but Alison’s figure still made it look sexy. The neckline was low enough to show some eye-catching cleavage.

They made their way downstairs, heading off to one of the resort’s non-nude areas. There was a selection of shops, bars and restaurants, for guests who wanted a more conservative experience, or just a break from the hedonism that prevailed elsewhere. The restaurant was still fairly quiet; and they chatted and ate like old times. Alison seemed to relax and enjoyed her evening, helped by a bottle of Merlot that was soon joined by a second.

Bobby smiled and chatted, cracking jokes and making his mother laugh. This was partly because he loved to see her happy; but the fact that it also made her tits wobble like two plates of jello didn’t hurt either. He couldn’t help but let his mind wander to the memory of his naked mom, astride his dick as she came earlier in the day. He imagined her riding his cock, her tits bouncing up and down on her chest as she slid up and down him, taking them both closer and closer to orgasm. His cock throbbed painfully in his pants, but he sensed it would be worth the wait.

“Are you even listening?”

“What?…Yes…of course I am.”

“Really, because you’ve just been staring at my boobs for the last 5 minutes; and I don’t think you heard a word I said.”

“Errr, sorry, I was just struck by how lovely you’re looking tonight.”

“Hmmmm… well it would be nice if you looked at my face once in a while as well.”

“Um… sorry. Wow, this wine is really nice…Cheers!” he raised his glass to toast her and she responded with a wry smile at his changing the subject.

After they finished the meal, they decided to check out some of the other night spots since it was still early. They wandered into a Hawaiian themed bar called “Aloha”. The waitresses were wearing grass skirts and bikini tops, which would have been positively overdressed for the rest of the resort, but looked quite sexy in the more conservative atmosphere of the clothed section. Overall it was quite cheesy but fun; and Alison ordered some cocktails that came in over-the-top pineapple containers with fruit and umbrellas. Bobby was having to keep one hand in his pocket to restrain his cock; and was thinking of suggesting they sit down so he could get some relief, when he noticed a brunette in a black dress waving at them. She made her way over and Bobby nudged Alison.

“Hey, look! It’s Cynthia.”

“What, oh no…”

“What’s the problem, I thought you liked her?”

“It was you that liked her as I recall; and anyway, I didn’t say I don’t like her, I just wanted us to have a normal evening, whatever normal is these days.”

Bobby didn’t have a chance to respond by the time Cynthia arrived.

“Hi you two! Wow, you look great!”

“Thanks, so do you.”

“Well, even we dykes like to glam it up once in a while. You know Pamela, right?”

Bobby recognised the curvy blonde with the pageboy haircut next to Cynthia. They were both wearing quite revealing dresses, Cynthia’s was a strappy top that just covered her breasts while Pamela was wearing a white dress with a plunging neckline and a push up bra, that made her boobs look like they were going to explode out of her dress.

“That’s the same dress you had isn’t it, Alison?” Bobby indicated Cynthia’s revealing black number.

“Um, it’s quite similar, yes.”

“You wore a dress like this?? Wow! With my little titties, I can get away with it; but you must have been falling out of it! Sorry, but…I mean…that must have looked pretty hot.”

Alison flushed at the memory of her night with the investors. “Yes, it was a little…revealing.”

“Can I get you guys a drink?” Bobby flashed his trademark smile; and Alison could see even Pam and Cynthia weren’t immune to Bobby’s charm.

“Sure, ok.”

Bobby fetched the girls some cocktails and handed them to Cyn and Pamela, forgetting that with his hands full his cock was unrestrained.

“Thanks! Wow, you really are pleased to see us,” Cynthia remarked, eyeing the tent in Bobby’s pants.

“Um, sorry.”

“Don’t be. That tool of yours is earning us a lot of cash, and keeping Pam very happy at night as well.”

“Excuse me??” Alison interjected.

“I halkalı elit escort mean the mold we took. I brought one of the toys on holiday with us; and Pamela loves it when I use it on her. You’re lucky you have the real thing.”

“Oh I see, um, yes, I suppose I am.”

They drank some more cocktails and the mood began to relax. Alison was clearly a little peeved at having their evening interrupted; but Pam and Cynthia proved to be really good company, and eventually she began to relax as well. By now the bar was filling up and getting pretty noisy, making it hard to talk. Alison surprised Bobby by suggesting they all go back to their suite and order up some drinks from room service.

When they arrived in the room, Cynthia and Pam were impressed by the palatial suite, and headed out to the balcony while Bobby ordered up some champagne.

“Wow, this room is amazing! And look at this view! It’s incredible!”

The champagne arrived and Bobby served it, playing the consummate host, but not bothering to try to cover his straining hard-on any more. The mood was getting looser and looser; and he figured that things were getting more interesting. Alison had put some music on; and Pam and Cynthia were slow dancing together, while Alison sat next to Bobby sipping her champagne. The mood was obviously getting romantic; and Alison leant across to kiss Bobby.

“I love you Bobby Stevens. I hope you know that.”

“I love you too, I wish this holiday would never end.”

“Mmm, I’ll drink to that.” Alison sipped the last of her glass and Bobby lifted the bottle out of the ice bucket to refill it, but realized it was empty.

“Oops, looks like I’d better order another bottle.”

Bobby called down to room service to get another bottle; and when he returned he noticed Cynthia and Pamela were in a major lip lock. Seeing the two girls making out was making him hornier; and he was contemplating pulling his cock out to stroke it when Cynthia remarked: “You know, it is really too warm to keep all these clothes on. Would anyone mind if I take my dress off?”

Bobby glanced at Alison, who looked a little taken aback, but didn’t say anything, so he replied: “I don’t mind, in fact, I was just thinking the same thing.”

“Cool!” Cynthia slipped out of her dress.

“I think I’ll join you. Would you unzip me?” Pam asked, turning so Cynthia could undo her dress before slipping it off with a shimmy, and striking a Marilyn Monroe pose. She had a curvy figure, with a big pair of boobs that contrasted with her page boy haircut; and Bobby couldn’t help admiring her as she resumed her sexy dancing with Cynthia.

“Fuck it, I’ve had blue balls long enough,” thought Bobby. “Let’s get this party started.”

“Hope you don’t mind if I join you?”

“We don’t mind, do we?” replied Pamela; and Cynthia smiled her approval. Bobby didn’t need any more encouragement, and slipped off his jacked and shirt before removing his trousers, letting his erection wave about in the air.

“Wow the famous Penis de Milo. Doesn’t it ever go down?” asked Pam.

“Not with three beautiful women around,” he smiled. He heard a knock from the main door and realized that room service had arrived with the wine. He went and let in the waitress, a cute little Mexican girl who seemed quite shy. She glanced nervously at Bobby’s cock, before setting the wine down on the table and scurrying off, not even waiting for a tip.

“Bobby, you frightened the poor girl off.” laughed Cynthia, breaking off from kissing Pam. Bobby said nothing; but admired the two naked girls as they sensuously rubbed their bodies against one another, Pam’s pale curves contrasting with Cynthia’s taught body and olive coloured skin.

Bobby opened the wine and poured his mom a glass, noticing she was glaring at him.

“What’s wrong?”

“Enjoying the view?” she whispered, so that Pam and Cyn didn’t hear.

“I’d enjoy it a lot more if you were naked as well.”

“I didn’t think you’d notice.”??”Are you kidding?”

“Well you are obviously very…excited…” She regarded his hard-on, “…about them.” She glanced at the girls who were making out naked.

“I’ve had this,” he gestured at his erection, “…all day long thinking about you, and only you. And you were the one who invited them up here. Why did you ask them if you didn’t want them here?”

“I know, I’m sorry, they’re just, well young and…”

“Stop with the ‘young’, will you?! You’re young and beautiful, and look better than women half your age. Now why don’t you slip out of these clothes, and let me see your beautiful body again?”

“I don’t know…”

“C’mon, they’ve already seen us naked on the beach, and you have nothing to be embarrassed about. In fact, your huge knockers will probably intimidate the hell out of ’em!”

“Bobby!” Alison admonished him but couldn’t help smiling bashfully and after a moment’s thought nodded her assent.

Bobby helped his mom to her feet, and tenderly slipped her dress off her shoulders, letting it fall halkalı escort to the floor. They stood naked facing one another; and he lifted her chin so he could look at her and kiss her tenderly on the lips.

“Oh good, more champagne, I was getting thirsty,” announced Cynthia, as she and Pam made their way over to the table to join Bobby and Alison. He refiled all the glasses and raised his for a toast. “Here’s to happy times!” They clinked glasses and drank.

Pamela glanced at Bobby’s cock again, “I’m sorry I don’t mean to stare, but when Cynthia brought the rubber version home, I told her she must have stretched the mold to make it bigger.”

Bobby felt his cock swell at the compliment and pushed himself forward slightly. “Nope it’s all me.”

“Can I touch it?” Pam looked from Bobby to Alison and finally Cynthia. Bobby just grinned while Alison gave a forced smile and shrugged; and Cynthia simply laughed.

“You’re asking me? After I’ve blown him, I think the least your entitled to is to cop a feel. That’s if Alison doesn’t mind.”

Alison did mind. The prospect of these girls admiring her sons cock and wanting to paw it made her jealous as hell; but she forced herself to simply smile. “You wanted him to meet other women and get this out of his system, remember?” she reminded herself.

Pamela reached out and wrapped her fingers around the shaft and squeezed.

“Wow, it’s like a rock! The dildo is only rubber; but this thing feels like it’s carved out of granite.” She continued to explore his shaft, feeling up and down its length before exploring the plum-like head, running the velvety foreskin back and forwards over the glans. It wasn’t so much that she was playing with him, more just curious to explore his dick.

“The skin is so soft, you know if I was going to go straight for a night I think it would be with this.”

She finally released his cock and hefted his balls, surprised at their weight and size.

“So, do you believe me now?” asked Cynthia with a wry look.

“Ohh, you didn’t exaggerate. That’s a great cock you have Bobby!” She smiled, patting his dick on the head like a puppy. They all laughed at the sight; and even Alison felt herself smiling, even sensing a certain pride at her son’s oversized dick. They fell silent and Alison became aware of Pamela shyly looking at her boobs.

“And I wasn’t exaggerating about Alison either was I?” Cyn commented, noticing her girlfriends’ gaze.

“Sorry I didn’t mean to stare,” giggled Pamela. “I guess Cynthia told you I have a thing for big boobs. I suppose it’s ’cause I got some myself, not that I can compare to you.”

“Imagine how I feel! I look like a 12-year-old next to you two!” remarked Cynthia.

“Awww, but you got a great ass, and I told you, I like small perky ones too!” she smiled at Cyn before turning her attention to Alison again. “But yours are HUGE, you must be used to getting a lot of attention.”?

“Umm, well yes. I do get my share of glances.”

“I’m sorry, I just have to ask would you mind if I…?” Pamela glanced at Bobby and Alison’s breasts with a questioning look. It took Bobby a moment to work out she was asking for permission to touch them, to feel up his mother.

“Sure, go ahead, I mean that’s if you don’t mind?” Bobby looked at Alison.

“Well, I don’t know, I mean… “

“Well, Pamela’s already stroked me; so I guess it’s only fair.” He wasn’t sure what sort of logic was involved in that statement; but the prospect of seeing Alison and Pamela getting into a clinch was too good to pass up. Alison was obviously still a little unsure; but the alcohol was loosening her up and the attention was quite flattering.

“Well, I suppose it would be ok.”

She stood patiently while Pam approached her and gently cupped her knockers, lifting the huge mounds and weighing them.

“Wow, they are so heavy.”

“Tell me about it.”

“They’re just made for motor boating!”

“Motor boating?” Alison looked confused.

“Don’t tell me you’ve never been motor boated?!”

“No.”

“Well allow me to be the first.” Pam put her face between Alison’s boobs and shook them “Muummm umm umm umm umm umm!”

She withdrew her face and, smiling, looked at Alison as they all laughed. “That’s motor boating!!”

“Oh I see! Goodness, well that’s a first!” Alison laughed and the mood relaxed.

“Your nipples are so cute,” remarked Pamela as she ran her fingertips over the nubs and felt them harden, “Mmmmmmm, I’ve just got to.”

With that, Pamela moved closer and licked Alison’s nipples, gently tickling them with her tongue, feeling them harden even more, before taking one of them in her mouth and sucking on it. Alison couldn’t stifle a gasp as she felt the other girl’s tender lips and tongue gently working on her nipple. She relaxed and allowed Pamela to continue to gently squeeze and worship her tits, the gentle touch of another woman being so different, but very pleasurable.

“Do you mind if I join you?” asked Cynthia, moving in closer. “There’s obviously more than enough to go ’round. Pamela surrendered one of Alison’s breasts; and Cynthia cupped it in both hands and began sucking on the teat, while Pamela continued to work on its companion. Alison moaned in pleasure, the sensation of having two women sucking her tits simultaneously was a new one to her, and one she was very much enjoying.

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