Jimmy's Mom

Story Info
His friends help mom recover from a bad Halloween date.
14.9k words
4.47
284.6k
507

Part 1 of the 2 part series

Updated 06/08/2023
Created 10/17/2016
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
SexyBeast
SexyBeast
2,529 Followers

(Author's Note: This story could easily have been in the Group Sex section, but since it does involve incest at one point, I put it here so no one was shocked when that moment comes. But it is not pure incest. There's also an element of Nonconsent as well. If I'm inspired, there may be a follow up. -- SB)

The boys were hanging out at Jimmy's house, getting high, drinking a little, and playing Xbox One. Jimmy's mom was out at a Halloween party with her new boyfriend, so they knew they had the house to themselves for the evening. She'd told Jimmy she'd be very late.

"Pass that thing over here," Wyatt said, reaching out for the vape. He sucked in a lungful of hash oil goodness, and then passed it on. "Dude, there's a sniper up in that tower."

Wyatt wasn't playing at the moment. The others all had controllers and were trying to sweep a town of terrorists. He wasn't as into the shooter games as his friends, so he didn't mind letting his friends play while he watched. But he was disappointed that Jimmy's mom wasn't around. Mrs. O had been his main crush from the moment he'd realized girls weren't yucky.

The group of four guys had been friends since grade school. Even now that they'd graduated high school, they were still thick as thieves. Two of them, Jimmy and Tanner, were going to college locally, while Wyatt and Parker had gone right to work after school. Wyatt made good money working construction. A year out of school, he had just about enough save to get his own place. They all still lived at home, and Wyatt knew as soon as he got an apartment the guys would always want to hang out there. He preferred hanging out where he could mack on Jimmy's mom. They all called Mrs. Owens by the affectionate nickname, Mrs. O. Wyatt always thought of it another way. Mrs. Oh-god-she's-hot.

Mrs. O's hotness was something all the guys agreed on. Wyatt suspected that even Jimmy thought his mom was hot, based on some of the things he'd let slip over the years. Sure, it was weird if Jimmy was into his mom like that, but Wyatt couldn't blame them. She was the sexiest mom out of their group by far. And it was a common topic of conversation among the guys. Jimmy tried to discourage it, but that just made them go at it harder.

It wasn't always easy to pick out her hotness. When they were younger, Mrs. O was very much the typical suburban mom. Obviously, she was a pretty blonde—her glasses somehow made her sexier—but she always dressed like a mom, which meant lots of khakis and loose sweaters, things like that. Sometimes she'd wear a dress that showed off some cleavage and clung to her body when Mr. O was taking her out, but the boys really had to look and speculate to see what kind of body she was hiding under there. Wyatt clearly remembered the first time he saw her in a bathing suit. It was a one-piece tank suit—not a bikini or anything—but it gave him a clear look at her body, and Wyatt had to either stay in the pool or keep a towel in his lap to hide his wood.

She wasn't built like a centerfold. The fact that she looked like a real woman somehow made her sexier. She wasn't heavy, like a lot of the other mothers, but she was curvy for sure. Her ass was on the plump side, but her tits were incredible. They were nice and round, and they still seemed to sit up there in that bathing suit like they were perky. Wyatt would have given anything to see her naked tits. He watched the way her tits moved in the bathing suit, memorizing every jiggle and bounce for his spank bank.

When Jimmy told them his parents were getting a divorce, Wyatt couldn't believe it. Mr. O wasn't anything special, as far as Wyatt could see, and he didn't think Jimmy's old man was going to do any better than Mrs. O. If Wyatt had a woman like that, he'd never let her go. Hell, he'd never let her out of bed.

At first, Mrs. O was depressed and sulky. Whenever Wyatt saw her, he always tried to be encouraging and flattered her relentlessly. The other guys did the same, but Wyatt always went the extra mile, even going so far as telling her how a beautiful woman like her wouldn't be alone for long. She blushed at that, and for a second he felt like there was a vibe between them. He bragged about it to the guys, but they told him he was crazy. Jimmy told him, "If you think you're going to work your way into her panties you're insane." Wyatt would always hold out hope.

Mrs. O snapped out of her post-divorce depression, which turned out to be a positive for everyone. Her confidence returned and she acquired a new attitude. She signed up for online dating and with the new attitude came a new wardrobe. Out went unflattering khakis and baggy sweaters, in came clingy tops and shorter skirts. Wyatt found every excuse he could to stop over Jimmy's to see what Mrs. O might be wearing. Whenever he saw an opening, Wyatt even flirted with her. She always told him he was crazy and blushed, but Wyatt was sure she liked the attention.

Wyatt had hoped to see Mrs. O before she left for the party that night, but she was already gone when the guys arrived. Jimmy explained she was changing at her boyfriend's.

"Do you like that guy?" Wyatt asked.

"I dunno. It's weird to have your mom dating. I see her get ready to go out and she's all done up. I mean, I guess she's a single woman, but it's hard to see your mom that way."

"She's sexing it up because she needs to get laid, man," Tanner said, cracking open a beer.

"Knock it off," Jimmy protested.

"Your mom's not an old lady. She's like what, 40 or something? I bet she still needs it," Parker chimed in.

"She's 45, and I don't know if she needs it. I don't want to know," Jimmy said.

"Have you heard her screwing yet? Is she loud?" Wyatt asked. The other guys laughed.

"What the fuck?" Jimmy said.

"She's been seeing this guy for over a month. They've got to be fucking by now. She doesn't seem like a prude to me. And this isn't the first boyfriend. She's brought other guys home, right?" Wyatt pressed.

"You make it sound like she's bring a different guy home every night," Jimmy said.

"Hey man, Karen needs it," Tanner said. The boys often referred to Mrs. O as Karen when they were talking about her sexually.

"Fuck, I'll give it to her. Karen needs a young man to get the job done," Parker said confidently.

"You'll have to line up behind Wyatt. He wants her bad," Tanner said.

"She's sexy as hell, of course I want her. I'd have to be gay if I didn't. You never answered, Jimmy. Have you ever heard Karen doing the deed? This house isn't that big. You'd have to hear something."

"No, I do not listen to my mom having sex. You guys are sick. How would you like it if I talking about fucking your mom, Parker?"

"You're welcome to her. I don't think my old man has touched her in years."

Wyatt noted that Jimmy did not explicitly say he hadn't heard his mom in the bedroom with men. He was jealous. He would have loved to overhear Mrs. O going at it. Jimmy probably didn't want to admit it because he sat in his room jerking off while listening to his mother coming.

It was past midnight when Wyatt heard the key in the deadbolt. The guys were so caught up in what they were doing they didn't realize they were about to be busted until the front door swung open and Mrs. O came into the room. Wyatt could see right away that she was drunk by the way she half-staggered into the room. The boys all turned to look at her, frozen in place. Beer cans and the vape pen sat out on the coffee table, waiting to be discovered. Mrs. O was cool, but she would not be cool with a bunch of underage boys getting high and drunk in her house. They were all 19 or 20. But a big smile spread across her pretty lips when she saw the boys.

"Hey guys, it's a Saturday night. Shouldn't you be out somewhere having fun?" she asked, leaning back against the door for support.

"Looks like you've been having enough fun for all of us," Wyatt said, staring at her.

Wyatt wasn't staring because she was drunk, but because of her costume. He had never seen Mrs. O look hotter. He guessed she was supposed to be a witch, based on the pointy black hat on her head. Her long blonde hair had streaks of black in it, and her makeup had her look sultry and sexy—not a middle aged mom at all. The rest of the costume was not a flowy witches gown, though. Mrs. O wore a tiny little black dress that clung to her figure and stopped well above her knees. It was a strapless bustier, with ornamental silver buckles down the front and a subtle, inlaid pattern that shimmered in the light. The dress, at least the top of it, almost looked more like lingerie than a dress. The outfit was completed with a choker at her neck, black fishnet stockings and very high heels that had her swaying as she stood at the door. She looked so incredible—so different—that Wyatt might not have recognized her on the street. She looked at least ten years younger with the makeup and that dress. And Wyatt wasn't the only one who noticed. All the guys were staring.

Jimmy was the first to move, hoping off the couch and standing in front of the coffee table to try and block her view. "Hey mom, what are you doing home. You said you'd be really late."

Mrs. O pulled her phone out of a little clutch purse he carried and looked at the time. "12:47 is late for me, but I know what you mean. Things did not go a planned. Sorry for ruining your evening."

"You're not ruining anything," Wyatt said. "Come on in and join us."

"I really should go up to bed. I've got to get out of this get-up," she replied, looking down at herself. She wore the outfit will, but it was obvious she was not used to being dressed like that.

"That's an awesome costume. Where did you get it?" Parker asked. His eyes were glowed to her chest, where her tits were spilling out of the dress. None of them had ever seen that much of her body on display.

"Thanks, Park. I put it together myself. I thought I'd embrace the spirit of letting go for Halloween."

Jimmy saw how his friends were looking at his mom. "Here, let me help you upstairs, Mom," he insisted.

"I'm not an old woman, Jimmy. I can get around on my own." She stepped forward and teetered on her heels. They didn't look easy to walk in if she'd been sober.

Wyatt moved to intercept Mrs. O before Jimmy could get to her. He steered her toward the couch, where Tanner quickly scooted aside, crushing Parker against the arm rest. She dropped heavily to the couch and sank in, causing her dress to ride up on her thighs. She seemed not to notice and did not adjust the hem. Wyatt's head nearly exploded when he saw the garter straps holding up her black thigh high stockings. He had never seen a real, live woman wearing stockings, they were just something he saw in pictures on the internet. He'd always thought they were hot, but girls his age just didn't wear that sort of thing. He was lucky if the girls he'd been with dressed up for him at all. Hooking up was just a casual thing for them.

He had been sitting in the arm chair to the right of the couch, but now he squeezed in on her other side, shoving the others over. Even with Parker being forced off the couch, Wyatt, Mrs. O and Tanner were still squeezed together. The television went right off as the boys focused on their friend's mom. Jimmy stared down at them, fuming.

"What happened to Steve? Why didn't he come in?" Jimmy asked.

"I took an Uber home. Excuse my language, but he's an asshole," she replied. The guys all laughed, and it looked like she enjoyed being the center of attention. "I need to get what I left at his place, but I don't think you'll be seeing him around again."

"If he let a babe like you get away, he is an asshole," Wyatt said, staring down at the strip of exposed, pale flesh above her stocking tops. He barely snapped his eyes up in time to meet her pretty blues when she turned to him. She patted him on the knee and left her hand there.

"Thanks, Wyatt. You've always been so sweet."

"So what did that asshole do?" asked Tanner, on her other side.

"I really shouldn't get into it with your boys. I don't know if it's appropriate."

"You're probably right, Mom," Jimmy said.

"We're really not boys anymore, Mrs. O. We all date. We've all been with chicks. We know the score," Parker said. He didn't look happy to be excluded from the cuddle up on the couch.

"I guess you're not just boys anymore, are you? But you'll probably always be that way to me. Let's just say we had a difference of opinion."

"About what?" Wyatt pressed. He saw sympathizing as a way to suck up to her.

"Fine. I just found out tonight that Steve is the jealous type, and I don't like that. I had enough of that with Jimmy's father. Steve went outside to smoke and when while he was gone another gentleman started talking to me. Steve found us talking when he came back and accused me of flirting and got really angry. I tried to calm him down, but that seemed to make it worse. He said some very nasty things."

"What nasty things? We can go out and kick the shit out of him," Tanner said.

"That's sweet, I guess," she replied, putting her other hand on Tanner's leg. He beamed. "But it's not necessary. I can take care of myself. He said some terrible things about my costume. He called me a slut and accused me of flirting with other men all night, which is not true. I can't help it if guys come over to me, can I?"

"Of course not," Wyatt replied with heavy sincerity. He placed his hand over hers and gave it a squeeze, which caused her to squeeze his knee. He felt a twitch in his crotch. "It's not your fault you're so pretty. And tonight, well, of course guys were coming up to you. I mean, he had to expect it, right?"

Mrs. O turned deep red. "Oh my, Wyatt. You need to stop. You're so sweet, but really, I'm literally old enough to be your mother. You shouldn't say things like that."

"He's right, Mrs. O. You look hot as hell. If Steve can't handle that, it's his loss," Parker chimed in. "He needs to be able to handle his business."

She laughed. "You boys are laying it on thick now. The ego boost is nice, but really, I don't need it. And I am nobody's business. I'm my own woman, and I can handle myself."

"No doubt," Tanner said, nodding.

"We're not just laying it on. If I had a girlfriend who looked like that, I'd be proud to show her off. I'd want other guys to want her." Wyatt let his words hang out there, wondering if he'd gone too far.

"Wyatt..." she said sternly.

At that moment, she finally took notice of the cans on the coffee table. Her eyes went from the table to each of the boys in turn, landing on Jimmy. "It looks like you boys were having a party of your own. Do you think that was a good idea?"

"Sorry, Mom. I thought you'd be out all night."

"You know that's not the point, young man."

"None of us were going to drive," Tanner said.

"And we figured we could stay the night. It's not so bad if we stay in, is it? It's not even illegal."

"That's if you have my permission. And what's this? I think this is illegal no matter what."

Mrs. O leaned forward and plucked the vape pen from the table. Wyatt was impressed that she even knew what it was. It appeared she was hipper than they gave her credit for. He also noticed that even Jimmy couldn't resist staring at his mom's tits when she leaned forward. It looked like she was going to fall out of that dress. Maybe he was going to jump on her and cover her.

"Boys, I'm very disappointed in you." Mrs. O adopted a stern look. "I'm going to have to call all your parents and have them come and pick you up."

She looked at all the boys, going from one to another, radiating parental disappointment. Wyatt knew his parents smoked pot, so he wasn't too worried, but he was concerned that this would make Mrs. O look at him differently. She held the look for almost a minute and then burst out laughing. Parker audibly sighed.

"Come one, guys. I know I'm not the cool mom, but I'm not going to report you to your parents. For one thing, I've had a few cocktails myself tonight, so I'd be a pretty big hypocrite to jump all over you for having few beers at home. And as Park said, you guys aren't kids anymore. You're all over 18 now. I guess that makes you men." She said the last word uncertainly, like she didn't quite believe it.

"We are men," Tanner said confidently.

"I've put band aids on all of your boo boos. That's a little hard for me to accept."

"What about the weed?" Parker asked.

"You boys shouldn't be doing that stuff either, but I honestly don't think it's any more dangerous than drinking. It's probably less dangerous. I never knew anyone who got high and got in fights or crashed their car. Mostly they just wanted to sit on the couch and listen to Pink Floyd, or giggle and fool around."

Wyatt could tell her reaction shocked Jimmy. Jimmy did not seem to like this looser, more fun version of his mother. He was shifting anxiously from foot to foot, like he was trying to find a way to get her out of there, but now that Mrs. O was planted on the couch she didn't seem to be inclined to go anywhere. Wyatt was sure Jimmy could see the way they were looking at her, and he understood why, but it wasn't fair that Jimmy got to keep his hot mom all to himself.

"So you're saying you've gotten high?" Tanner asked.

"I didn't say that. I admit nothing," she replied, looking to Tanner at her side with a sly smile.

"If your friends were doing it, I doubt you just stood around and watched," he countered.

"Yeah, it's not like your little angel Jimmy held out," Parker added.

"Dude," Jimmy said, exasperated.

Mrs. O gave her son a disapproving look then said, "I am not saying I've done pot, but if I did, it would have been a very long time ago. Long before any of you were even a twinkle in your daddies' eyes."

"The vape's not tapped yet. Why not take a hit for old time's sake?" Wyatt suggested.

"That's not a good idea," she replied, eyeing the vape warily.

Wyatt snatched the vape from the table and held it out for her. "It's easy. Just hold the button here and inhale. I'll show you."

He was still feeling the effects of his last hit, but he wanted to encourage her, so he did another. She watched as he sucked in the vapor, held it, and then blew out a huge cloud. She recoiled, like she expected to choke on the cloud, but she breathed it in fine. He offered her the vape pen again and she took it, but she did not partake.

"That's not like a smoke cloud at all," Mrs. O said. "I wish they had these things around back in the day."

"Then go ahead and try it now," Parker said.

"You don't have to, Mom. Guys, leave her alone."

"Thank you for the defense, honey, but I can take care of myself."

"I don't know," Jimmy mumbled.

"What was that?" she complained.

"Just, you're a little drunk, Mom. Maybe your judgement..."

"Jimmy, I have had a few drinks, but I still have my wits about me and I can make my own decisions."

Wyatt knew she had had more than a few drinks, but the way she held herself, the flush on her cheeks, and the way she kept smiling, but he was on her side. He wanted Mrs. O to party with them. If ever there was going to be a chance of closing the deal with his friend's mom, this was it. The more wrecked she was, the more likely it was to happen, he reasoned. But he did not want her getting so messed up that she passed out. He did not want to jump Mrs. O's unconscious body. He wanted her to want it too.

"Go ahead, show him," Wyatt encouraged.

Mrs. O gave Jimmy a hard glare and held the vape to her lips. The little blue light went on when she pressed the button and she sucked the tip, pulling the hash oil vapor deep into her lungs. She held the vape in one hand, and her grip on his leg tightened as she took it in. Wyatt couldn't believe what a deep drag she took. He never could have held it like that. He also knew she was going to be crazy stoned. Mrs. O had no idea how much strong pot had become in the last 20 years. Watching her suck that tip gave him visions of other things in her mouth, and Wyatt felt his cock hardening. Mrs. O held the vapor as long as she could, until her face turned red, and then she exhaled a huge cloud of vapor. All the guys—except Jimmy—cheered, and she beamed.

SexyBeast
SexyBeast
2,529 Followers