Halloween With Mom

Everyone in the story is over 18 years old. Any similarity to persons living or dead is purely coincidental. This story is fiction, and at no time and in no way does this story intend to portray real life, actual circumstances, actual persons or situations, places, or actions. This story is the product of the author's imagination. This story includes scenes of graphic sex needed to further the plot, and should NOT be read by minors or anyone that might be offended by such filth.

This story is copyrighted by 49greg under United States Copyright law and the Bern Convention and may not be copied or posted anywhere other than Literotica.com without written permission from 49greg.

XXXXXX

"Hello, are you there, I'm a little late."

Mary felt a rush of relief to see the text pop up on her screen, and quickly typed an answer.

"Yes, I'm here, I was worried that you were going to stand me up, everything OK?"

She hit send, then worried that she sounded too eager. Not for the first time she felt a little embarrassed at the screen ID she had chosen It was the name of a girl she knew in High School and Mary had secretly admired the way that her friend had so easily flirted, and more, with boys. At least it was better than the 'Titts1000' she had originally planned to use.

"Sorry about that, running a little late." came the reply from the man she only knew as 'CaptFlint'.

That name sounded piratical and easy going at the same time. He was a terrible flirt and had gotten Mary to reveal too many secret feelings in the two weeks they had been flirting at first in the open chat room before quickly moving to Private Messages, then to their private chat room.

"We're here now, that's what matters, how was your day?" She typed.

At once feeling foolish, formal, and fumbling. She wanted to be more forward and flirty. She knew that Captain Flint was younger than she was, and didn't want to sound like a boring old lady.

"It was boring and time seemed to have slowed down. And nothing perk me up, no messages, no pictures, nothing ... sigh."

Mary gave a shiver, she felt sexy, there was nothing but words on the screen, but she felt her nipples erect, she wanted nothing more than to touch herself. But she was wearing bluejeans, thick, stiff, new, bluejeans. And plain cotton underwear. She didn't understand why she had put them on instead of a silky robe with nothing under. That's what the Captain had asked her to wear.

"I'm sorry, I chickened out, and was really too busy to send it, from the time I got up, late, until I got home." she whined.

And it did seem whiney, she thought.

"But then you did take one, or more?" Captain Flint answered.

She could tell he was a fast typist. She liked that he sent full messages. Some of the men she had chatted with were awful spellers or used abbreviations she didn't understand. Perhaps a student, his language and spelling also told her he was educated. Perhaps a grad student?

He had mentioned living in Northern Iowa, and went to a University, and that's just where Woodston was, and since they had added a Masters program to Woodston College, it now called itself a University. Of course there was a State University of Norther Iowa as well as several other private schools, and a two year Community College.

Mary hesitated.

"You did take them, didn't you?" asked Captain Flint.

She trembled, unbuckled her belt, unbuttoned the waistband.

"Yes, I was terrified and excited." she typed and sent.

"Are they sexy? Describe them? What are you wearing now?" was the demanding answer.

Mary stood, pulled the jeans down and off, pulled off her panties, ripped off the blouse as she turned and headed for her closet. Her bra came next, and the silky robe floated around her naked body, untied as she returned to the seat. She snatched a fluffy towel she had gotten earlier from the bathroom and dropped it on her chair before sitting down.

She briefly wondered what he son would think of her if he knew what she was doing, what she planned on doing.

"Just a satin robe, a red one, that's all." she typed.

"Did you wear it in any pics?"

"Yes, untied and open." she slashed out, trembling as she sent it before she could stop herself.

"How about your costume, did you wear that too, in the pics?"

"Yes, but just one pic of that. I only took a few altogether, I'm worried about that costume, wearing it in public would scare me." she typed back.

There was a long wait. One hand started to cup and squeeze her breast, edging for her nipple, the other slid down past her tummy. She hoped it would be another of the 'fun' nights that she had come to enjoy so much.

XXXXX

John Walker paused, he was laying in bed with his laptop, chatting with a woman. He didn't want to push her to fast or too far. And it was fun, flirting, playing, talking sexy to a strange woman. He was sure it was a woman now, older than him, maybe as old as his mom.

He knew how hot his mom was, all the guys in high school certainly said she was. And his older Sister, Susan was just as hot. But she was down in Iowa City working on her Masters. He brushed the erection that probed upwards from under his boxers, pressing up against his sweats.

John had broken up with his girlfriend recently, well not too recently. Too tell the truth she had dumped him. He felt like she would be available next semester, but he was having too much fun on line with this woman to miss her. His only fear was that his Mom would find out. Dad wouldn't care, and a part of him wondered what it would be like living with his Dad.

It would be odd. Dad lived down in Ames, and he could live there and go to the University there, but he liked Woodston, and mom had agreed not to 'bug' him about when he would be home or when he went to bed. As far as she was concerned he was studying now. And if he was going to a big University, he wanted it to be in Iowa City.

His mind wandered a bit, thinking about his ex girl friend Peggy, Peggy Blackett. They had known each other since the third grade, she was a great girl, nice, pretty, studious. Not like her sister Ruth. She was one of the "Bad Girls", getting drunk, dating boys and leaving them.

He remembered a conversation with Ruth on the school bus when they were in fourth grade, She said she was thinking of going by her middle name, because she wanted to be a pirate, and pirates were 'Ruthless". It didn't make sense to him at the time, but he had always remembered it.

While Peggy was a 'good' girl, Ruth was wild, and he didn't understand what Peggy said when she broke up with him. She said that Ruth was more his style. He wondered what she meant by that. Had he gone too fast for Peg? Well no sense worrying about it now, all over and done.

He knew his mom wanted him to be a model student, model citizen, model everything, and dating a wild girl like Ruth would not fit in, as far as his mom was concerned. His mom was so uptight, so, 'upstanding in the community' as she put it.

She would be shocked at the things he was doing with another mature woman on the internet. She had no idea what could go on through a computer. The only thing she knew about was word processors to read her students assignments with, spreadsheets to record grades on, and emails to send grades in to the office. Oh yeah, and to send him email reminders to 'dress for success' and 'eat a real lunch.'

XXXX

Mary was slowly working herself up, Captain Flint was taking a little time again. Obviously he was a little upset she hadn't sent any pics to him. She told herself that it would be OK to let him see them. She wasn't identifiable.

She had tacked a white bedsheet over the wall, pinning it to the cheap but dark crown molding in the basement room they used as a guest bedroom. Her daughter and then her son used to have sleepovers with their friends in that room.

It could have been anywhere, it was a blank background. She had dressed in what she had always thought was a scandalous outfit. But when it was on, she felt good, sexy, empowered. The panties were barely there. She had to shave a shocking amount of skin so as not show any stray hairs. She felt good about herself. She looked good.

Trembling she opened her file manager. Clicked on 'view' and clicked on 'hidden items' so she could find the folder, and files she had hidden. Her cursor slid over the third one she took. She took a breath, let it out, and went back to the chat room, clicked on the paperclip symbol then browsed through and found her pics that way. She took a deep breath.

XXXXX

John was lost in thought, not paying attention to the pc screen. He was thinking about his mom, working downstairs in the room they called the 'office'. When he was little she made him do his homework and studying there.

She was down there now, probably making some undergrad miserable. When he was in one of her classes she certainly didn't let him get away with anything but the best work. Luckily there were two other profs in her department at Woodston and he got away with only taking one class from her.

He wondered about her. She dated some, after Dad divorced her, once or twice she didn't get back till late, and he had been surprised to see her hair a little frazzled and her dress rumpled once. He thought back and decided that was when he started thinking of her as a good looking woman. But still his Mom.

Suddenly he saw Vicky100's message.

"What do you think?"

He clicked on the icon and downloaded the pic. It came up fast. She didn't have a super high definition, but the pic showed everything.

She had turned her face away with a hand up covering it just in case. Her body was partly sideways, the brilliant red hair was obviously a wig, the robe was practically transparent, the other hand was holding it behind her back. One leg, the one farthest away, was raised, he couldn't see what it was resting on, the pic didn't go all the way.

The background was pure white, the black panties where skimpy in front and as he looked closer and zoomed in, he could see a definite camel toe and the shadow of her trimmed pubic hair. Her tummy wasn't gaunt and her hip bones didn't jut, and her boobs where wonderful, the bra held them out for anyone to see, or touch or suck, the robe being pulled away from her shoulder. He could see part of one butt, a nipple, and guessed the panties were a thong. He was fully hard.

"Wow, that is hot!" he typed.

"You think so? I'm not a young girl you know, actually I'm a housewife, just not a wife, if you can understand that," she typed back.

"So you're divorced?" he typed.

"Yup, that's the word," she answered.

"That's great," he typed. Not completely sure why. He wanted more pics, but didn't want to get pushy.

"Do you really want to see my costume?" she typed back.

"You know it, and if we are to meet at that party in Riverton, It would help to know what to look for," he answered.

There was a long wait. John though she might have left, except that her name still showed in the private chat room. He clicked on her profile again. It didn't have much more than she was 'over 18', she was 'curious', 'looking for friends', and that she 'enjoyed reading sexy stories, wanted to explore meeting people on line for fun chatting, maybe more."

It was the 'maybe more' that John had been pushing her toward for the last few weeks. The charity Halloween party in Riverton was in a hotel, he urged her to get a room so she could enjoy drinking and not worry about driving home. He himself was one year short of the drinking age of twenty one, and anyway, he wanted to keep his wits about him. He was hoping that a happy and tipsy Vicky1000 would be willing to spend the night. With him.

XXXXXX

Mary had to stop touching herself, and finally sent the pic of her in costume. She wore the orange wig again, and a mask. She felt her heart pounding and tried to talk herself out of being worried.

First of all, it didn't show her face, there was a mask and wig, second, she had showed more of her body in the previous pic. Still she was nervous, sending the pic gave, in a way, her promise to go to the party. Well she had her ticket to the annual charity Halloween ball. He had assured her he was over eighteen, she had insisted on that when she heard he was a student, only being relieved when he confirmed he was a college student.

She wondered what the mother of CaptFlint would think if she knew her son was flirting with a mother in her early forties. A divorced mother. Living with her son. She thought about her own son. She loved her own son, well not "that" way, but worried. She had to give him "the talk" when he hit puberty, and years later made sure he knew what a condom was and how important it was to use it. She even supplied him with a box of them.

It wasn't hard to decide to do that. She knew how early people were having sex now, and how the abstinence programs the schools had were utter failures. To her it was the next step in growing up. She thought of it at the time the same way she thought when she bought and gave to him a dozen hand towels. She knew what he was doing, not only with the towels in the bathroom, but his socks, and there had even been the occasional spot of cum on her sexier panties.

So she gave him the towels not long after "the talk", told him they were his alone and he could keep them in his room, and to just put them in the laundry hamper when he was done. She was careful not to mention what she expected him to do with them. She had to smile at how red his face got.

She assumed her son was sexually active now, and commiserated with him when he broke up with his latest flame, or more accurately, when Peggy broke up with him. Since then he spent more and more time on the internet. She knew he could find porn, and meet people, but hoped that he knew the dangers. Well, he was in his junior year, and all of twenty years old. She smiled, and nearly laughed, what if he was on line right now, maybe with a young girl, talking her to send pics. She suddenly grimaced. What if he was talking to some other lonely old woman, buttering her up. She put that thought out of her head.

XXXXXX

John watched the pic unfold. It was sexy. The dress was red, thin, and short. It had a ragged hem and while some of the ragged hem was knee length, lots of leg was on display. She was once again not facing him head on, but slightly turned. One hand on her hip, the other at her side. It was a sexy female devil mask, and she had short horns and a tail peeked over her shoulder. He got up and carried his laptop to his bed.

The side facing him more closely, her right side, had a tear or rip that went up to her hip, he could see the top of her red stocking, and an inch of white skin, and the clasp of a garter. He shivered. He pushed his sweats down and off, pulling his boxers to his ankles as he did. Then pulled the bedclothes up to his waist.

He reached for the hand towel he had placed on the bed, pulling it under the covers. He was rock hard. Her next message popped up on the screen.

"Are you excited?"

"Yes, are you?"

XXXXX

Mary was very excited, so excited she felt able to come at any time. She decided to move to the bed, last time she chatted with CaptFlint he had admitted to laying in bed with his laptop. She again thought of her son laying on, or in his bed, playing with himself as he chatted with the college girls he knew, or looked at porn. She wondered how many hand towels she would find in the laundry this week.

"Yes, I am very excited, turned on, hold on a few minutes, I want to get in bed," she typed and sent.

She got up, dropped the robe she had just gotten on, then put the laptop on her night stand, pushing the trashy romance novel off to the floor. She pulled the sheets and comforter back and placed her towel on the bed, before laying down with the laptop. She pulled the covers up and adjusted the pillows, trying to keep the laptop from falling off.

She ended up sitting up, pillows behind her against the headboard. Her laptop over the covers resting on her drawn up knees and the covers barely covering her lap. She felt conspicuous with her bare breasts, she wished she had turned up the thermostat earlier. It was getting cold in the evenings now.

"Are you naked, in bed yet," came from CaptFlint as she finally looked at the laptop.

"Yes, yes, and sitting up, my naked breasts are out in the room, my nipples are so hard, my pussy so wet," she typed, embarrassed at her words, so forward, so explicit, but she knew the man she was chatting with would love it.

CaptFlint loved it, this older woman, naked, her breasts exposed, obviously with a finger in her wet pussy, all because of him. He was nearly ready to blow just thinking about it, he stopped stroking long enough to type.

"I am too, well almost, I'm in bed, but I'm wearing a T-shirt. It's chilly, too chilly here. I'd like to turn the thermostat warmer, but the people I share the house with like it cooler," he typed and sent, not wanting to pin down just how many or few people lived in his house.

"I like sleeping in cold weather, and it's late, when we finish up tonight I'll just turn off the lights and go to bed," she typed back.

"I'd like to cuddle up to you, after we finished up," he typed.

"Are you typing one handed," she typed.

"No, I take my hand off to type, if I didn't I'd explode," he said.

She was shocked and excited that he admitted that. They had never explicitly mentioned what they were doing, she decided to raise the tempo. She felt guilty, and yet wanted more.

"My heart is pounding so hard that my nipples, my hard nipples, would probably jerk in time, if I left them alone enough to watch. When I'm not typing I'm sliding fingers in my wet pussy, and pinching my nipples, my laptop keeps threatening to slide off, I'm ready, and I don't even have my 'friend' from my nightstand drawer inside me buzzing away." she typed, then went back to playing with herself.

She stopped again, then selected another photo, the most blatant one, and sent it. Then went back to touching herself, while looking at the pic on her screen.

XXXXX

John had to stop. He had his hand towel ready, draped from his knees ready to grab. Then the pic unfolded.

It showed her, her face turned to the side one hand covering it, leaning against the white wall, that was now obviously a bed sheet hung on the wall. Her legs were spread and bent slightly. She was wearing the garter belt and stockings and bra, her exposed nipples were erect, and she had no panties on.

Her other hand was between her legs, showing the upper part of a strip of pubic hair, she clearly had two fingers inside herself, he could see a glint of wetness on her fingers.

He shot, just getting the hand towel over himself in time. His back arched and he savored the orgasm as it hit, trying to make it last as long as possible. He finally relaxed and looked at the screen again. She had sent another message.

"I have three fingers in me right now, and my thumb alongside my clit, my fat, big clit, and I came, came hard, with aftershocks still hitting." she had typed.

Mary lay back, pushed the laptop to her side, pushed her fingers in again and pushed her clit again, and more shocks hit. Her nipples were too sensitive to touch, and she knew her clit would be as well in a second.

XXXXX

John looked at her pic, and felt drained, but he had one more thing to do. He found the pic he had taken. It showed nothing of his face, other than his mouth with the fake mustache, He started to send it and something stopped him. Instead he just typed.

"Darling Viki, I just came, a lot, I'm wiped out. I hope you don't mind, but I have to force myself up and get to studying. I had a great time. The party starts at six thirty this Saturday and I'll be there at sevenish.