Mom Then and Now – Chapter One
(FMM, MM, bi, voy, ehib, inc)
It was a warm Sunday afternoon in June. Josh strolled through his making his way home from his summer job. He waved to neighbours washing their cars, mowing their lawns and basically doing all their various weekend chores. He and his mom had lived in the neighbourhood for as long as he could remember and he knew most of these people by name.
Judith Avers, his mom, was a successful realtor with her own branch office in the area. She was well respected in their neighbourhood as well as in the business community. She had raised Josh on her own, somehow completing her own education while raising a young boy to manhood.
She and her ex-husband had divorced shortly after Josh was born so Josh never really knew him. He rarely, if ever visited, and the only consistent contact was a birthday present—delivered by messenger every June 25th. It had been a long time since he even looked at one those gifts, he usually tossed them straight into the garbage. They were typically something pretty inappropriate, like toys or games—things for a much younger child. He had written-off his father and rarely gave him much thought.
Arriving home, Josh scooped up the evening paper at the door before entering. He called out to his mom but there was no response. He pulled his tee-shirt over his head and dabbed the sweat off his torso. Bounding down the stairs to the basement to use the only computer in the house, he stopped at the laundry room to deposit his sweaty garment. As he opened the door his eyes caught a flash of skin, two long shapely legs and a generous full round ass.
“Oh my God, Josh!” His mom called out, “What are you doing sneaking up on me.”
“I called out when I got home,” he said. “What are you doing dressed like that down here?”
Judith was wearing the skimpiest of outfits with shorts that were more like French-cut underwear. Most of her ass was showing and Josh was very impressed at how firm and round she was. She turned partially toward him and he saw her fine full breast pushing out against the thin translucent fabric of her top. He was treated to the outline of her areola in profile, plus an enormous protruding nipple.
“Get out of here and stop ogling me, young man,” she ordered, “I'll explain after I've changed again.”
Josh shrugged, but couldn't resist taking one more peak before leaving. He thought to himself how funny it was that even though he knew his mom was sexy, just seeing that bit of extra skin, made it all he could think about. He loved his mom and thought she was the most perfect woman alive. He had never seen her naked but often wished he had. She was a spectacular beauty with long flowing black hair and sparkling hazel eyes—her hourglass figure was accentuated by her large 'D' cup breasts. She was the very definition of a MILF.
When he got to the computer he opened his email account and checked for messages. There was one from his best friend Colin and he opened it. 'Dude, you need to check this out' was all it said. He clicked on the link and a new window filled with the images of beautiful young naked women. It looked as though Colin had built a blog and filled it with his favorites.
“I can't wait until you get your own computer Josh,” he heard his mom's voice behind him.
He spun around in his chair. “Well, hopefully there'll be enough from my earnings this summer for college books and a computer,” he said. “I think this is another of Colin's attempts to become a porn magnate,” he laughed.
“Very funny,” she said. “Maybe if he was a little more like you, he'd have a scholarship as well. Then he wouldn't be wasting time surfing porn.”
“Colin is just fine the way he is,” Josh defended his life-long friend. “Much as I hate to admit it, I surf porn too. Colin and I balance each other off, I keep him in check and he keeps me from being boring.”
“Hm, and how's that plan working for you? I haven't seen many girls around in a while, maybe you could use a new co-host?” his mom chucked.
“So what was with that sexy little outfit?” Josh asked, deflecting her comment. “I've never seen you in anything like that before. Believe me I would have remembered. You sure beat anything on Colin's page.”
“Why thank you,” she said, “I think that was a complement—that is if I ever wanted to look like those skinny little girls. I was washing a bunch of old clothes to give to charity and I tried something on to see if it still fit.”
“Pretty risqué for a charity and that goes double for you. Did you wear a lot of stuff like that at one time? Not that I'm criticizing, you looked seriously hot.”
“Alright, now THAT was a complement, and a nice one,” she kissed him on the top of the head. “Yes, well I guess I've have had my wilder days, but they're far, far behind me now.”
“That's too bad,” he snickered. “Behind you, was looking pretty good a few minutes ago.”
“Over the line, young man. Watch that mouth of yours.”
“Oh come on mom,” he said, “I'll be eighteen this week. Isn't it time you start treating me more like an adult. I'm old enough to enlist and die for my country, I can vote, I can have sexual relations and even get married.”
“You're right about all of that,” she admitted, “but until you add self sufficient and independent to that list, you've still got a boss, me. Don't worry, I'll let you know when you're a man.”
That stung but he just couldn't be angry with her, she was an unbelievable mom, always had been. He wanted for nothing and she was always there for him. He watched her as she tidied up around the basement. She was wearing tight stretchy capri slacks with an oversized black tee-shirt. As she bent over, her ass stretched out the material with smooth clean lines. 'Hm, she's wearing a thong,' he thought to himself 'or maybe nothing at all'.
As Judith tidied up, she realized the ogling wasn't over yet. A strange feeling came over her as she placed her hands on her hips, tightening her tee-shirt and emphasizing her full 'D' cupped breasts. It had the desired effect as his eyes darted to the fresh new target. 'Enough of this,' she thought as she shook off the feelings and continued tidying.
The next morning began as usual with the two of them scurrying around, preparing for work. Both of them started at 10:00 so breakfast was always around 8:30.
“What are your shifts this week?” Judith asked.
“Good,” he answered, “all full days except for Wednesday, I have my day off then.”
“Great,” his mom said, “you've got your birthday off, can we celebrate together? Or would you rather do something special, like a party?”
“No, just you and I would be special enough, but then again, maybe you could wear that little outfit again. That would be a great present.”
“Careful, Josh,” she raised an eyebrow at him. 'He's still thinking about it,' she thought to herself.
After breakfast, they both headed out at the same time with little pecks on the cheek and a smile. The week passed quickly and soon it was Wednesday morning. Josh awoke with a start to the sound of the front doorbell. He tripped his way down the stairs, still half asleep. It was a deliveryman with a parcel and he immediately knew what it was. After signing for it, Josh held the package in his hands sensing the size and weight of its contents.
He detached an envelope that was stuck to the top and read the message inside. It was from his father.
Happy Birthday, Josh,
I'm especially sorry I can't be there again this year. I'm working overseas now for the next two years and travel options will be limited. This is a big year for you, son, graduating school with honors and starting college. I'm very proud of you.
I hope this gift will be just what you need for your new life as a college student. I know you'll succeed and make your mom and I proud. Good luck son. Love, John.
He looked at the box again, it seemed too small to hold a brief case, although what on earth would he need one of those for? He tore off the wrapping and to his amazement there was an apple logo on the box. 'A computer,' he thought, 'he's bought me a MacBook.' He opened the box and slid out the sleek silver unit, placing it on the table. He opened it up and hit the power button—the signature chime sounded as the computer came to life. It was beautiful and he couldn't believe Dad, his dad, had bought it for him.
Judith came down the stairs and stood behind him. She wrapped her arms around him hugging his chest as she kissed the side of his head. He reveled in the feeling of her luscious breasts pressing against his back.
“Happy Birthday sweetie,” his mom said as she squeezed him one more time, intensifying the feeling behind him. “Is that from John?”
“Yeah, I'm shocked, I was expecting a video game at best. This is pretty awesome.”
“He called me to ask what you needed. I told him you could use a computer for college,” she said. “He just got a bonus for going overseas and he blew a lot of it on that unit. It's the top of the line.”
“Wow, I never knew you still spoke to him?” Josh said. “Well, this is one gift I think I'll hang on to. Say, why aren't you dressed for work?”
“Well we're both pretty busy these days and I thought I'd take advantage of your day off and take one off myself. Do you mind if I spend the day with you on your birthday?”
“Are you kidding?” He said. “That would be the best present of all. What were you thinking about doing?
Her heart warmed at the thought of her son being so happy to be with her. “I was thinking that, after a special breakfast, we could go out and shop for some new clothes for college.”
“Sounds great, I could use a few new sweats and jeans.”
“After that, we can come home for lunch and then maybe lounge around the pool and spend time together.”
“I'm in with that, as long as we're together,” he said with a smile.
They had a great time shopping and Josh was happy with all the new clothes. While walking through one of the stores, Josh stopped and leered at a mannequin sporting a beautiful but brief bikini. Josh looked at his mom and smiled and they continued on shopping. They were back home by noon and dropped arm-loads of new clothes on the sofa. Judith went out back to start up the barbeque and make hamburgers for lunch. They gobbled everything down like they were starving and then they sat back in their chairs.
“Whew, I'm stuffed,” Judith said. “Let's put on our suits and go lay down by the pool?
They went to their rooms to get changed but Judith had a little surprise planned for Josh. While he was trying on clothes at the store, she had doubled back to purchase the bikini he had noticed. She had a good Idea what he was thinking about when he looked back at her and smiled. She hadn't had time to try it on, but now, holding it in her hand… 'No wonder the little bugger liked this' she thought.
She put it on and checked herself in the full-length mirror. The bottom was a very sexy high-cut 'V' in the front, but still presentable, but the back was basically a string thong. Between her legs there was just the tiniest strip of material and it teased at her clit and hardly covered her labia at all. If she were to bend over her pussy would be in plain view. The top supported her ample 38D breasts and even pushed them nicely together, but her cleavage was completely open with only another little string holding the cups together. The bra just barely covered her large areolas and the too much movement would show some of the deep pink.
She sat on the bed trying to decide if she should go through with it. Then she remembered the look on his face when he caught her in the laundry room, especially when he looked back for that second peek. She recalled how it made her feel so sexy, something she hadn't experienced in a long time. She would do it. She got up and marched downstairs and out the door to the yard.
Josh was already at the pool, skimming for leaves and debris. She approached with the confident gate of a runway model and Josh's jaw dropped when he saw her. She stood at the edge of the pool and spoke to him as he stared at her from the side.
“Well, I see this old bod still has some street value,” she laughed. “I bought this after I saw you look at it in the store. When you looked at me and smiled, my thought was that you wanted to see me wearing it. Was I wrong?”
Josh's eyes couldn't seem to stay focused. He looked first here, then there, then like a laser he fixed on her tits. She looked down and both areolas were half exposed. Quickly, she tucked them back in and gave him a shy smile, shrugging her shoulders. She turned around and gave him a look behind and his audible gasp made her shiver with excitement.
“I… I'm speechless,” he said, “Mom, you're so hot it's killing me. I probably shouldn't be feeling like this but I can't help it, you're so incredibly sexy. You were right, I did want to see you in that suit, I knew you'd look unbelievable, but I never dreamed you'd do it.”
His swim trunks strained at the pressure of his swollen cock and Judith chuckled at the sight. She wished she could see more of it—it looked as though he had quite a nice package there.
“Oh dear,” she said, “you're going to give me a swollen head. I just wanted to do something special for you since you seemed to enjoy that old outfit so much. You're probably seeing less now than you did then. I should go back and change into something more modest now though?”
“Oh God no,” he begged, “Please, can I just look at you a little longer, it's my birthday, please?”
“All right then, but just a few minutes more. This IS very inappropriate your know, but it's your birthday and you are eighteen.”
The little strip between her legs was driving her crazy as it rubbed her clit and labia. Every time she moved, even a little, she felt small shocks of pleasure. She was becoming very horny and she needed to get the suit off before it got her in trouble. She was wearing platform sandals and a mischievous thought came to her.
“You know I think I like the suit better bare footed. What do you think Josh?” And she slipped off her sandals.
“You're right, looks even sexier,” he said.
“Good,” She bent over and picked up the sandals giving him a nice flash of her pussy.
“Shit,” she heard him whisper behind her and that sent another shiver up her spine.
“All right,” she finally said, “that's it for now. I'm beginning to feel pretty self-conscious. Maybe I'll put it on for you again some other day, that's if you're a good boy.”
She marched back to the house, deliberately swaying her ass all she went. Half way there she pulled the ties on the bottom and gathered it in her left hand. As she continued to walk away her right hand reach behind her back and undid the top. She gathered that as well with her other hand. Josh watched her naked backside in wonder at but then he held his breath as she approached the large glass patio doors. There was a full frontal reflection of her beauty and she smiled widely as she slid open the doors and walked in.
When she got back to her room she couldn't believe what she'd done. 'What's wrong with me,' she thought, “what kind of mother am I, parading myself in front of my young horny son?'
She lay on the bed as her hand quickly found its way between her legs. In no time she was rolling side to side on the bed in the grips of a powerful orgasm. She went to the washroom and cleaned up before putting on a more demure two-piece swimsuit. When she got back outside Josh still couldn't stop looking at her.
“What are you looking at now? She said. Everything's pretty much covered up, you've seen me in this suit plenty of times.”
“I know,” Josh answered, “but I can't un-see what I've seen. It doesn't matter what you're wearing now, all I see is that amazing ass and those big beautiful tits pushed up together. Not to mention the pretty 'V' down there that I never knew about. Sorry Mom, it's all burned into my memory now.”
“Imagine what you want, just please don't talk to me like that. I'm your mother not some tramp you picked up, treat me with more respect. I put on something daring for your enjoyment because I felt you were old enough to deal with it like and adult, don't make me rethink that decision.”
But deep down she liked the language he had used. She wanted to hear more but she dare not act on it. This had already gone much too far. They both lay by the pool together all afternoon talking until dinner. Judith ordered sushi from Josh's favorite restaurant and they had some sake with it.
“So tell me, Josh, why aren't you and Colin dating more girls these days? There used to be lots of them hanging around.”
“No reason really, we both had finals and I was tutoring Colin. It was a great way for me to study as well. Even though I finished in the top ten, Colin did very well himself.”
“That's nice, I didn't know that. You're such a good boy and a really good friend as well.”
At the end of the evening they both went up to bed and Judith wished him a happy birthday before kissing him goodnight. Josh entered his room and immediately called Colin to tell him about his day.
“No fucking way,” Colin shouted, “Your mom's a real MILF, I can't believe you saw so much. What do you think it means? Do you think she'll show you more?”
“I don't know,” Josh said, “I'm so horny right now, I wish you were here sleeping over so I could get some relief. I'm going to have to take care of myself tonight.”
“Sorry about that kiddo,” Colin replied, “I'd love to help you out with that but it would look a little weird me showing up so late at night for a sleepover.”
“Yeah I know, well, see you at work tomorrow then.”
Colin and Josh were no strangers to each other's bodies. As children they explored each other discovering the nature of their sexual parts. They had played with each other for years, graduating from handjobs to blowjobs and even anal a few times. They were both very bisexual now and saw no shame in helping each other out sexually. They both craved pussy even more, but a nice juicy cock was fun too. Long ago, they had discovered it was the easiest way to get relief when they needed it. No questions asked, easy as pie. Why should girls have all the fun, they thought.
During finals, they were studying day and night and there was just no time for girls. Whenever they got horny, they were happy to take care of each other, no talking, no foreplay, no involvements, just relief.
Back at Josh's place, the next morning things were back to normal. Judith and Josh bustled around, then had breakfast and left. At work, Josh and Colin talked about things in the stock room.
“So what do you think will happen with your mom next?” Colin asked.
“Probably nothing,” Josh said. “She was just having some fun with me on my birthday. I can't see why she'd do any more.”
“Yeah but she did say she might put the suit on again for you, but only if you were a good boy. Do you think she meant anything special by that?”
“I don't really know. Say, what if I let her see me naked, you know, by accident. Maybe she'll reciprocate.” Josh said.
“Maybe,” Colin agreed, “Can I go back to your place after work and stay the night?”
“Sure, if you want, at least tonight I'll be able to get some help if I need it.”
Josh called his mom and she said it would be fine with her. She told him to fix his own dinner because she had a few showings and wouldn't be home before nine. When the boys arrived at seven, they ate some frozen dinners before going out to the pool.
“Say Josh,” Colin said, “leave the lights out in the pool and we can go skinny dipping, what do you say?
“Okay,” Josh said, “sounds like fun,” he started for the pool with his suit on.
“No, man,” Colin said, “Take it off here and leave it, it's more exciting that way.”
Josh smiled and stripped off his suit. The two of them walked out naked in the setting daylight to the pool. They splashed around for hours thoroughly enjoying the experience. Now and then they would fondle each other to hardness as they sat on the edge of the pool catching their breath. They continued to play and pleasure each other, unaware that Judith had come home early and was watching from the window.
She squinted, trying to make out what they were doing and why the lights were out. Then it came to her. 'My god they're naked and playing with each other's peckers,' she thought, 'my sons gay.' The thought didn't upset her as much as surprise her. After all he did get an erection looking at her the day before. What to do next, she wondered. She decided to start by ruining their little party.
The two boys were on the edge of the pool stroking each other when suddenly, all the lights went on. Surprised, they both immediately slid into the water. They looked toward the house and saw Judith stroll to pool as if nothing was wrong.
“Good evening boys, how's the water?”
“Great they both said hugging the edge of the pool.”
“Why aren't you swimming then? She asked.
“Oh, just tired, we've been in here a while.”
“Alright, so hop out and we can have hot drinks in the house, you must be chilled from being in the water so long.”
“No we're fine,” Colin said, “We're just fine in here.”
“WELL I'M NOT FINE, now both of you get those bare asses out of the pool and back to the house, RIGHT NOW!”
Colin and Josh didn't dare answer back, she obviously knew they were naked and what they were up to. They each climbed out and stood, covering their genitals. Judith pointed them to the house with her upraised arm.
She was right behind them as they walked in and tried to grab their swimsuits.
“Leave those suits where they are,” Judith warned as she sat in a chair facing them. She stared at them both for a long time. “Alright, hands at your sides. If you want to be little exhibitionists then act the part. Come on, you should be enjoying this,” she said. “Let me see those boy cocks.”
But instead she was shocked to see anything but boy cocks. Even chilled from the cold air, they were both still pretty impressive. These were full-grown man cocks and balls, especially Josh's.
“Well I take it back, no little boy cocks here,” she said. “You boys are pretty remarkable for your age, but then you're both eighteen, I keep forgetting that. Now tell me the whole story, are you both gay? I mean I did see you both playing with each other out there. What gives, believe me I won't be upset.”
“We're not gay Mom, although we do enjoy taking care of each other. We've been doing it since we were kids. It's just easier to get relief when we need it. We both love to fuck girls as well, even more, so don't worry,” Josh pleaded.
“Oh really? You've both had girls have you? How many?”
“Two,” Josh said, staring at the floor.”
“FIVE,” Colin said proudly, looking Judith straight in the eye.”
“And how often?” She pressed, tying to make them slip up.
“As often as we could, are you kidding?” Colin snapped back.
“Oh, listen to Casanova over there. So that's it? You've just been scratching each other's itch, really?”
