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As Diane walked away from the asshole's car, toward her house, he yelled through the window after her, "Call me?"
"Yeah, right," she muttered, and kept on walking to her front door, her heels clacking on the long sidewalk. The asshole's car rolled away into the night, and Diane breathed a sigh of relief. Dating was much harder than she remembered.
As she approached the townhouse that was her main consolation prize after the divorce, Diane wondered not for the first time how it had come to this -- how after twenty-five years of marriage, she found herself dating at age 42. Some days, she felt as if she'd been sleeping for the past two decades, dreaming of an ideal life, and now that she was awake, she could see it was all just a lie. But like Rip Van Winkle, when she woke up, she found she was no longer young. Her prime years were behind her.
Diane unlocked the front door, stepped into the foyer, and eased the door shut behind her. She heard the television blaring in the next room, and glanced up at the clock. Just past midnight. She dropped her keys in the basket, and made her way into the living room. As expected, there was Alan, her sixteen year-old son, reclining on the couch with his feet up on the ottoman, his laptop computer balanced precariously on his legs. And he was fast asleep. Of course. Diane shook her head. How the computer hadn't slipped off his legs and crashed to the floor she had no idea, but she'd threatened more than once that the day it did, he wouldn't be getting a new one. Because that's the kind of thing a mother says, even if she never means it.
She already knew from past experience that it wasn't worth it to try and wake him. Alan slept like a rock, and at a lanky six feet tall, there was no picking him up and carrying him to bed anymore like the old days. Especially when she maxed out at about five-five without the heels on. So instead she grabbed the laptop, and carried it with her over to the kitchen counter, where it would be safer. Like Alan, it was asleep when she picked it up, the screen black. But at some point on the way, she must have bumped one of the keys, because as she set it down on the counter, it sprang back to life. And what Diane saw immediately got her attention.
The website was called "Busty MILFs" and seemed to feature a variety of older looking women, all of them big-chested, some of them topless or downright naked, and some engaged in sex acts with what appeared to be younger guys. Diane blushed a bit, but still made herself scroll down the page to get the full picture. Then she navigated over to the next tab on the web browser, which was a YouTube knock-off site in which all of the videos were porn clips. The clip open at the moment was called "Busty MILF Titfuck" and when she hit the play button, she could see that it pretty much lived up to that description, and turned it off after only a few seconds.
The remaining tab on the browser was some kind of shoddy-looking chat room site. Nothings as slick looking as the chat rooms AOL used to have, back in the day when she used to have an AOL account. But it was the same basic concept. There seemed to be dozens of users in the room, and the mostly idiotic and/or untranslatable chatter scrolled up from the bottom at a fast pace. Not surprisingly, based on the other two websites, Alan's nickname here was "Lookn4MILF". Chuckling to herself, she guessed that "Lookn4BustyMILF" had been too many letters. Oh well. Boys will be boys.
Diane made a note of the chat room site, and decided she'd do some research on it later, just to make sure it didn't have a reputation for being Pedophile Central. Although she suspected Alan was too smart to be fooled by somebody with that kind of agenda. Then she closed down the web browser and the computer, left it there on the counter, and went up to her bedroom.
As she changed out of her dress, Diane took a moment to consider herself in the mirror. Five foot five. Blonde hair that only needed a little help every few months staying blonde. Not as thin as she used to be, but she still had an hourglass figure, her hips nicely balanced by 36DD breasts, which despite birthing two kids, had only begun to sag a little in the past few years. Her ass ... well she could always use a smaller ass, but again, she'd seen far worse, and the time she spent on the treadmill every day seemed to be helping to tighten up both it and her legs.
All in all, Diane wasn't one of those women who was overly-critical of how she looked. How she lived ... that was another matter entirely. Dating assholes like the one she'd been dumb enough to let her boss set her up with tonight wasn't the solution to happiness, and she'd known it even as she'd agreed to it. But the fact was, she was lonely, and realized she had been for a long time, even before the divorce. And she was constantly horny. That needed to change somehow.
The next day was Saturday, and Diane spent most of it doing housework. Alan slept till after ten, having moved to his bed at some point in the middle of the night, then after a quick Pop Tart, bolted out the door, yelling something about going to the mall with Marty and Frank. Which was just as well. It gave her a chance to clean the living room without him plopped in the middle of it playing video games and getting chips all over the floor.
As she was vacuuming, Diane found something odd. Although maybe not so odd, considering what she'd found on Alan's laptop the night before. There was a bottle of hand lotion on the floor, just under the couch. Combined with the box of tissues on the ottoman, she could piece together what had probably happened. In a word: masturbation. One of Alan's favorite pastimes these days, if the number of times he locked himself in his bedroom in a week was any indication. Apparently, he'd moved his venue to the living room last night, and when he fell asleep, the lotion had fallen to the floor. Once she'd figure this out, she made a point of looking around for any "used" tissues, but didn't find any.
On a hunch, she went upstairs, and found in his hamper the pair of jeans he'd been wearing the day before, and sure enough, there in the left pocket was a still somewhat damp and musky smelling wad of tissues. And likewise in the right pocket. So he'd gone for a double-header. And this solved the mystery of why, every so often, she'd find pieces of a shredded tissue in the clothes dryer. She'd assumed it was because Alan tended to blow his nose a lot because of his hay fever. But as far as she knew, those tissues always made it to the garbage can.
Diane shook her head. Teenagers were a constant source of mystery to her. Her daughter Amanda, now in college, had been a bit easier to figure out, perhaps because she was a girl, and so they had something in common. But Alan just seemed to surprise her at least once a week. Compared to some other kids, he was relatively maintenance-free. He got excellent grades, and was even kind of a geek. He never got in trouble, and never challenged her the way Amanda had. But every once in a while, he'd do something like this, which showed that hormones were a huge influence on his life these days.
After the cleaning was done, Diane had put in her time on the treadmill, took a shower, then sat down and got caught up with her soaps on the TiVo. Alan got home just in time for dinner -- he was always good about that -- and as they ate while watching one of his sci-fi shows, she considered whether she should lecture him about either the laptop or the tissues. But she realized that both conversations could lead them into an awkward discussion, and it was one that she wasn't up for right now.
"So," she asked. "What are your big plans for tonight?"
He shrugged. "Nothing much. I have a paper due for history on Monday. I might start working on that."
"You might start working on it? Alan, it's Saturday."
A smile crept onto face. "Jeez, gullible much, Mom?"
Diane shook her head, "You're an idiot," then threw a green bean at him, smiling herself.
"I do have to work on my history paper, though. I did the outline and most of the research the other day, but I need to find a few more sources and actually write it. Mrs. Reese is a dick about having enough sources."
"Well ... whatever you're doing, you always get A's. So far be it from me to question your methods. It's not like I got the grades you get when I was in high school."
"What are you doing tonight? Got another big date?" he asked.
"No. Not tonight. I was out later than I wanted to be last night. Tonight, I plan to just veg out. Maybe do some online shopping."
"Sounds like fun," Alan said, and carried both his and her dishes to the sink, rinsed them off, and put them in the dishwasher. Then cleaned up the pots and pans. That was their arrangement -- she cooked the meal, he cleaned up after it. At times like this, with just the two of them in the house, it seemed as if they were more of an old married couple than a mother and a son -- each set in their ways, each with their role, moving around each other like comfortable clockwork.
After this, Alan disappeared up to his room with the laptop. Diane watched another couple of TV shows, then wandered upstairs with a bowl of ice cream. Alan's bedroom was right at the top of the stairs, and the door was closed. Which made her wonder what he was up to in there. Possibly just paper research, as he said ... or possibly something else. But she wasn't going to bang on the door to find out. He'd never given her a reason to violate his privacy, and as this thought passed through her mind, she felt a little guilty about having looked at his laptop the night before. Which gave her an idea...
Continuing down the hall, past the bathroom, past her own bedroom, she entered the guest bedroom, which they usually referred to as "the office" -- because it had the computer in it. Alan rarely used it, probably because his laptop was newer and faster -- his father had bought it for him for Christmas. This computer was almost five years old now, and for no more than Diane used it, she hadn't been able to justify replacing it yet. It was a little slow, but overall, seemed to work just fine. She booted it up, knowing that this would take a good ten minutes, then went to her room and changed into a tanktop and sweatpants, removing her bra, which had been digging into her sides all afternoon. She really needed to buy some new ones.
By the time she got back to the computer, the computer was finally warmed up. Diane checked her email -- nothing but junk -- then pulled up the web browser, and typed in the URL for the chat room site that Alan had been on the night before. After thinking for a few minutes about what nickname to create, she finally settled on "FunnyMomma" and entered the room. She wasn't sure why she was even doing it. On the surface, she told herself she wanted to make sure the site was safe for her son to be using. But under the surface, Diane knew better -- she wanted to eavesdrop on her son, and see what he was up to.
As with the night before, the chatter on the main chat room was fast and furious, most of it idiotic. As she suspected, Diane found Alan's nickname -- "Lookn4MILF" -- on the main list, and was sorely tempted to message him saying, "I thought you were working on your history paper, you big liar!" But that would defeat the whole purpose of eavesdropping on him. So she sat and waited instead, to see if he would say anything in the room. And after a few minutes, he did: "any busty moms out there?" Smiling, Diane was tempted to respond. After all, she was a busty mom. But she was pretty sure what he was after, and decided against it.
A few minutes later, he posted the same thing. But a few minutes after that, Diane was surprised when a personal IM box popped onto her screen, from Lookn4MILF, saying, "hi r u really a mom?"
Instinctively, Diane blushed, and only after the fact did she realize what a strange reaction that was. He couldn't see her, didn't know who she was. She considered what to type, then settled on, "yes i am"
He responded immediately, "kewl. asl?"
Diane chuckled quietly to herself. She hadn't seen those letters -- "asl" -- in a few years, since she stopped using AOL. "well i hope my sex is female if i'm a mom!" she typed.
"lol true ... sorry," he replied. "AL then?"
She decided to make herself younger: "38, near NY." The second part wasn't a lie. They lived in Connecticut, which was near New York. "and you?"
"16 m ct." So at least he was being honest. "u come here alot?" he asked.
"no it's my first time. is it fun here?"
"yah i think so."
"what do you do here?" she asked, and decided to draw attention to the 300 pound gorilla in the room. "you know, other than look for busty moms?"
His response was quick. "LOL u saw that in the room right?"
"yup."
"okay so now i have to ask."
"ask what?" she said, knowing full well what he meant.
"r u busty?" And Diane blushed again.
"i don't know. is 36dd busty?"
"hellz yes! damn thats hyuge!!!" Diane shook her head, grinning.
"i guess it's not small," she replied.
"not small at all. how old r yr kids?" The question didn't seem to follow from the sentence before it, which left Diane a bit confused. But she answered anyway, lying of course.
"just one. he's 14."
"damn he must have a boner all the time lookin at you."
Diane really blushed at this. "what??? how, if i'm his mom?"
"so what? big boobs are big boobs. i look at my moms all the time."
"you do???"
"yah, shes pretty big." Well. This was certainly enlightening, she thought.
"does she know you look at her like that?"
"probly not. but i dont know for sure. sumtimes i think mebbe."
"why do u think that?" she asked, very curious to hear the answer.
"cuz sumtimes she walks around w no bra on an they get all jiggly."
"maybe the bra just isn't comfortable. mine gets that way."
"yah mebbe. but its really hot anyway. gives me a huge boner."
"what??? you get a boner looking at your mom's boobs?" Diane couldn't believe she was typing those words, but knew that she had to clarify that Alan was saying exactly what she thought he was saying.
"totally. like rock hard. diamond hard. like it is right now. ;)"
More blushing. "why is it hard now?" Again, words she couldn't believe she was typing.
"thinkin of my moms boobs. and yours."
"well i'm sure she'd be very flattered if she knew, lol."
"u think so?"
"well i was kidding. i don't really know." Which was a lie, of course. She knew.
"r u flattered?" he asked, cutting right to the chase.
"to be honest ... kind of." And that was not a lie. Which nobody was more surprised about than Diane herself.
"good, cuz its so hard for u. its out and im touchin it."
"you are not. really?"
"hellz yeah. im strokin it for u, mommy."
Diane nearly jumped away from the computer at this, and looked over her shoulder, to make sure Alan wasn't standing right there. Then she realized what he must be doing, and typed: "stroking it for me? or for your real mom?"
"right now for u. will u be my mommy?" Okay. So it was role playing he was after.
"um. i guess so. what do i need to do?" she asked.
"let me see your boobs."
"i guess that couldn't hurt."
"then stroke my boner for me."
"oh i see, you need a hand with it eh?" Diane felt equal parts excited and disgusted with herself for this, but by now, had decided to play the role to its full extent, and see just how far Alan would go with it.
"mmm yes mommy."
"okay i take my top off and you see my big 36dd tits. then i gently stroke your young hard cock."
"ohhh mommy i love u so much!"
"do you want to suck mommy's tits? like you did when you were a baby?"
"mmm yes pls."
"okay you take my nipple in your mouth, while i stroke your cock faster."
"mmm yes yes. im so close!"
"thats it baby, cum for mommy."
"mmmmmmmm"
"cum all over mommy's big tits baby. show her how much you love her."
"ohhhhhhhhhh mommmmyyyyyy cummmmmmnnnnn"
And just then, Diane heard a noise from the direction of Alan's room. As if he had knocked something onto the floor. She hoped it was a bottle of lotion, and not the laptop. Regardless, the noise brought her back to the reality of what she'd done. She'd just had cyber sex with her son. She'd helped him get off. What kind of freakish mother did that make her? Even worse than this, though, Diane had enjoyed it. She knew, because her panties were soaked beneath the sweatpants.
After a few moments, Alan IM'd her again, "oh mommy that wuz the best ever."
Glad to know it wasn't the laptop he'd dropped, Diane replied, "was it really?"
"yah. i came so hard. so messy. i never came that hard before."
"well im glad i could help." And the weird thing was, this was true. She was glad.
"i wish u were my real mommy," he said, and Diane almost cried for some reason.
"awww, you're too sweet. but who knows, maybe your real mommy is even better."
"lol true mebbe. but i could never ask her."
"no? why not?" she asked, somewhat teasingly.
Marisol
- 05.09.2020
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