A Caring Motherbytompayne1809©
This story is a prequel to the encounters between Joanne, John and Chris and Chris's former schoolmate Jim and his family in Chapters 6 and 7 of my earlier work, Meeting the Maddisons. The two stories stand alone, but I wanted to explore the relationship between shy Chris and his parents who want to do everything they can to help him. I may take the story of Joanne and Chris further but I am working on the final chapters of Meeting the Maddisons when they finally get to the Sex Olympics. We shall see. Hope you enjoy A Caring Mother.
Joanne had been worried about her son Chris for some time. Several years actually. Right through school he'd never had a date. He just seemed incredibly shy around girls. When it came time to find a date for the prom he locked himself in his room and no matter how hard Joanne tried to get him to ask a girl to go with him, he'd just run away and hide.
"Maybe he's gay," said his father John, an ex-military man who regarded getting a woman in bed as similar to storming the beaches of Normandy. Just put your head down and go for it.
"No, I don't think so," said Joanne. "I'm not picking that vibe up at all. I think he's just incredibly shy."
"Maybe he just needs a bit of help. Why don't you line up a date for him. What about that nice girl down the street, the Robinson's daughter, what's her name?"
"Emily? No I think it would be even worse if I fixed him up with a date. He'd not say a word and she'd think him a total dork and the situation would be even worse. No John, this is something Chris has to do on his own. I just wish I knew how I could help him."
Truth was Joanne knew very well that Chris wasn't gay. She'd found Playboy magazines stuck under his bed. One time she'd gone into his room to pick up his washing thinking he was out, and he was at his desk with his back to her. Over his shoulder she saw that he was looking at porn on the computer. It had only been a flash of a second before Chris managed to close the lid, but she'd seen over his shoulder it was definitely a photo of a woman sucking off a man's cock, not a man doing it to a man.
She'd closed the door quickly and apologized to him through the door. She couldn't be sure as she only saw him from behind, but she was sure Chris had been masturbating as he looked at the photo. She knocked on the door and Chris had said to come in. He looked very embarrassed. Joanne said sorry, but she thought he was out and only wanted to collect his washing. Chris didn't get up and Joanne realized it must be because he had an erection. She picked up the washing and quickly left the room. Chris was obviously embarrassed and didn't say a word.
"John, I know he's not gay because I recently caught him looking at porn on his computer and it certainly wasn't gay porn."
"Really – what happened?" John said, sounding almost excited.
Joanne explained what had happened.
"Was he embarrassed that you caught him?"
"Yes, he didn't say anything, but I could tell."
"Did you say anything to him about it?"
"No, I just pretended I hadn't seen anything and left."
"Maybe that was the wrong thing to do. We have to get through to him that masturbating is healthy. I tell you once he gets more confident about sex he'll get up the courage to ask a girl out."
"Oh, John, if you talk to him about that sort of thing you know he'll freak out."
Her husband thought for a second.
"You're right Jo, that's why it has to be you who has to talk to him. Perhaps you should go in and have a quiet word with him that it's OK to masturbate to images of girls having sex."
Joanne thought about it all day. She wasn't prudish or hung up about sex. In fact she dressed pretty provocatively most of the time. She had a good figure and even though she was 39 she looked ten years younger. She guessed Chris had seen her undressed around the house once or twice but didn't think much about it. She was proud of her body and knew she attracted men with her blonde hair cut in a neat bob that framed her angelic looking face. Her big blue eyes drew in everybody to look at her.
Over the years Chris was at school she frequently visited the school wearing tight jumpers with stretch jeans tucked into knee high boots. She helped out around the school, serving food at the canteen and helping out on sports days. She had good sized boobs, a slim waist, flat stomach and shapely legs. In summer she generally wore dresses that showed off her shapely legs and had a generous cleavage. She knew the teenage boys ogled her, and she quite liked the attention. Some of the other moms glanced at her disapprovingly, but she didn't care. She knew she was what is known as a "hot soccer mom". What she didn't know was that the teenage boys in her son's soccer team called her a MILF – a Mother I'd Like to Fuck.
Chris had heard these comments about his mom, and tried to fight the boys who said it to defend his mother. But it only made things worse, and they openly spoke in front of him how they would like to feel her tits, stick their fingers in her cunt and take her up the ass.
Truth was Chris had often thought the same thing, and he was deeply ashamed of those thoughts. He knew his mom was smoking hot. The previous day she'd almost caught him beating off as he looked at porn on his computer. God that was almost so embarrassing. But she hadn't said anything so maybe he'd got away with it. Chris looked out the back window from his bedroom and saw his mother on a deckchair below wearing a tiny black bikini working on a summer tan. She was lying on her front and couldn't see him as he gazed down on her. Chris was stunned at the vision below. He picked up a pair of binoculars to get an even closer look at her body as she lay on the deckchair. He could see the pores of her skin sweating and the light down of hair on her ass. She had pulled the sides of her bikini bottom into the crack of her ass so her cheeks could get a good tan. She'd undone the straps of her top so her back was clear. As Chris watched he saw his mother slip her fingers under the material of her bikini bottom to press them even tighter into her ass crack.
Watching through the binoculars Chris's heart pounded hard, so hard he was sure his mother could hear it down below. Then he couldn't believe his eyes as he watched her lift the material clear of her ass crack and for a tantalizing moment he had a close up view through the binoculars of his mother's asshole. It was pink and hairless. Chris didn't know if his mother shaved off all her pubic hair like the women did in the porn films he'd seen on the internet. He sure hoped so. He thought it made them look completely naked and open, with absolutely nothing to hide. But would his own mother do that too? Surely not. She's no porn star. But he became determined to find out.
He watched her for a long time, his eyes gazing intently at her back, her hips, her ass cheeks and her long legs. After a while his mother moved to turn over and Chris ducked his head back inside the window. He sneaked a peek and saw she had her dark glasses on so he couldn't be sure if her eyes were closed or not. Damn. But he decided she wouldn't lie there with her eyes open all the time so he risked taking a longer look from the side of the window. He was glad he did. Her top was off and her breasts lay open to the sun and his gaze. They were a good size and flopped to the side of her chest. Chris thought that was different from many of the women he's seen on porn films whose tits stood straight up when they lay on their back. Maybe that meant his mom's tits were real. He got the binoculars out and trained them on his mom's breasts, watching them rise and fall with her steady breathing. Her pink nipples were flat and not erect like little thimbles. He liked that. He shifted the binoculars over her chest and admired the ripples of her rib cage before he reached the hard flat stomach. Her bikini was cut very low, so low that it barely covered her pubic mound. Chris couldn't see any pubic hair sticking out, but he was dying to know if she was shaved all the way. He'd have to try and catch her in the shower and make like it was an accident.
Chris didn't know it, but lying on the deckchair below Joanne had noticed a shadow at the window above her. She'd only narrowly opened her eyes and she couldn't be sure without moving. But she felt someone was watching her. John was away for the day, and the only one at home that it could be was Chris.
Joanne didn't move. She was luxuriating in the sun and felt dreamy. Heck. If Chris wanted to look at her topless maybe it's a good thing. In fact it gave her quite a thrill to know her shy 18 year old son who showed no interest in girls his own age was gazing at her nearly naked body. She reached for the suntan oil and applied a large amount to her breasts and chest. She saw the shadow in the window move. He was watching!
Well, I'll give him a show, she thought, and squirted the oil over her flat stomach. She worked the oil in, slipping her fingers under the sides of the bikini to spread the shiny liquid over her hips and thighs.
Should she be even more daring? She slipped the tips of her fingers under the bikini above her pubic mound and moved them around spreading the slippery oil. She had shaved that morning, leaving only a little triangle of hair above her clitoris. She heard a sharp intake of breath above her and knew Chris was watching closely. She had him hooked. She poured a dollop of oil into her right hand and then slid her entire hand under the material, spreading the oil all over her pubis. With her left hand she lifted the material clear and down so Chris would be able to get a flash of this forbidden part of her body.
Again she heard the intake of breath above her. Is he masturbating as he sees this? Oh I hope so, Joanne thought devilishly. She moved her right hand around her pubic mound and even slipped a finger over her clitoris and into her vagina. Maybe this will show Chris that there's nothing wrong with masturbation and he can see that women do it too. She heard heavy breathing above her and the sounds of regular movement. She increased the speed of her finger rubbing on her well lubricated clitoris, and her breathing got heavier and heavier.
She was really into it now. She could feel it rising, her muscles tensed, she threw her head back and as it rushed to a climax she let out a low guttural cry.
Joanne's fingers flew over her clitoris. Her left hand tugging down her bikini bottom shifted to insert two fingers deep into her vagina. She heard another loud gasp from the upstairs window, but she was beyond caring. She knew there could be a dozen strangers standing around watching her and she couldn't stop. That thought flashing across her mind even spurred her on. She wanted a second climax. She knew it was coming. Her muscles clenched hard. Her fingers were trapped in her tightening vagina. Her nipples were painfully hard. Sweat was pouring off her body. Then all of a sudden, like a giant wave crashing against a cliff, the orgasm hit her.
Liquid spurted from her vagina as she came, soaking her left hand and drenching her bikini bottom. All the muscles in her body stretched hard as wave after wave of orgasm wracked through her body. Never had she had such an intensive orgasm from masturbation. Was it because she knew her son was watching her that made it so intense? She didn't care. As she slowly came down from the peak she'd just climbed, she heard a cry from above. Was her son was coming too?
Upstairs, Chris couldn't believe his eyes. His mom was fingering herself to orgasm in the deckchair below him and he was watching every movement in extreme close up through the binoculars. He could see her fingers moving underneath the bikini bottom, and his heart leaped when she used her other hand to lift the material free of her pubic area.
"Holy Shit!" he almost cried out as he saw that she was mostly bare down there. He thought he saw a little bit of hair, but now he knew his mother took the care to shave off almost all of her pubic hair. He was so proud of her.
She was going further, dipping her fingers into her cunt with one hand while rubbing her clit with the other. Chris couldn't believe his eyes. He reached one hand down to grab his cock and started whacking himself off while he watched his mom through the binoculars held in the other hand. He saw her body shudder and she threw her head back, mouth wide open and an ecstatic cry come out of her mouth.
"Fuck, she's coming!" Chris muttered to himself. His hand flew faster over his dick as he watched his mother intently. Then just as his mother's cries subsided Chris knew he was coming too. With a muffled cry sperm spurted from his cock, splashing on the wall and windowsill. His knees buckled with the force of his ejaculation and he lost his balance. His grip on the binoculars loosened and then he realized with horror that he was dropping them. He dived for them but the heavy binoculars bounced once on the windowsill and then, to his terror, they fell right out the window. He heard them crash on the stone floor below, just yards from where his mother lay on her deckchair. Horrified, Chris pulled his head in away from the window. He heard a shocked cry of surprise from below, but he didn't dare look out.
"What's that," he heard his startled mother cry. He heard her get up out of her deckchair and go over to see what had fallen on the floor and smashed.
"Jim, did you drop something?" she called out.
Chris felt like hiding under his bed or running from his room to pretend he wasn't there. But he was frozen to the spot in fear and kept his mouth firmly shut.
"Chris, it's your binoculars! Did you drop them?"
Chris didn't dare say anything. She'd know he'd been watching her through those binoculars.
"Come on Chris, I know you're there. It's only me and you home. Binoculars don't fly out of windows by themselves. Please come to the window."
Chris realized he was trapped and there was no escape. With the blood drained from his face he edged his way to the window and looked down at his mother. She was standing there still topless, but holding the incriminating broken binoculars.
"Er hi mum. Oh what's that? My binoculars? Oh, they must have fallen from the windowsill. I'm, er, rearranging my room and put them on the windowsill and must have knocked them out through the window."
"Hmmm," Joanne said as she looked at the binoculars. They were clearly broken. One lens was broken and plastic rings had been smashed in the fall.
"I'm afraid they're broken, dear. I'll bring them up."
Joanne didn't believe him for one second. But if he'd been using the binoculars he would have got the most incredible close up view of what she had just been doing. Somehow that thought excited her.
She put on her silk dressing gown and quickly went up the stairs with the broken binoculars. When she got to Chris's room he was in a frenzy of moving things around. He was trying to make it appear he really had been reorganizing his room. She giggled to herself.
"It's such a shame dear, I know how you love looking through these binoculars," she said mischievously, hinting she secretly knew he'd been using them to look at her fingering herself down below in the garden.
"It brings things so much closer, doesn't it dear," she said smiling as she handed the broken binoculars to her son.
"Oh, er, yes mum," Chris said nervously.
Joanne walked over to the window.
"Just how could they possibly fall out the window?" she said.
She made a point of looking around the windowsill, and with a start realized she was looking at puddles of her son's cum on the sill and dripping down the wall below it. She knew what had happened – he'd dropped them while he was ejaculating from watching her having her own orgasm down below.
What should she do? If she says anything would it embarrass him even further? Would he retreat into himself with shame that he'd been caught spying on his own mother? Or would it be best to confront him about it right now, get it out in the open?
She looked at her son. He was just about shivering with fear and shame. She decided this wasn't the right time.
"Don't worry Chris. We'll see if Santa will bring you another pair of binoculars. Now, you'd better finish off tidying up your room," she said and left Chris to recover by himself.
Chris didn't dare emerge from his room for the rest of the day. Joanne was worried about him. Would this embarrassment set him back even further? When John got back home that evening and Chris still didn't come out of his room, Joanne decided to ask her husband what she should do.
She told him she'd been sunbaking topless out in the back garden and she suspected Chris was quietly watching her from his bedroom window upstairs.
John wasn't upset at this, in fact he seemed a little excited.
"Oh, and what happened?" he asked.
"Well, I must admit I got a bit dreamy in the sun and with that oil on, and I started feeling myself."
"What, you felt yourself up while you suspected our son was watching you?"
"John, I wasn't certain that he was watching. Well not at first. It just sort of developed. It was so good in the sun and I must admit I felt a bit sexy thinking someone might be watching."
"Which bikini did you have on?" John asked.
"The black one."
"Isn't that the one that barely covers anything?"
"Yes, I suppose you could say that," Joanne smiled at him.
"Wow, no wonder he was spying on you. What happened next?"
"Well, I slipped my hand under the bottoms and well, you know, did what a girl sometimes has to do."
"And you didn't worry that Chris was watching you?"
"No, it sort of added to the sexiness of it all."
"Go on, did you use both hands like you usually do?"
"Yes, my right hand rubbed my clit while my left stuck the fingers in."
"Did you keep the bottoms on?"
"Yes, but I sort of pulled them out and aside to get my fingers in."
"You sure gave him a show didn't you? Lucky boy."
"But at the end, after I came, he dropped his binoculars out the window and they smashed right near me."
"Oh Jesus. You mean he knows you know that he was watching you?"
"I don't know. When I took the broken binoculars up to him in his room he pretended they just fell through the window while he was tidying up. But I saw he had ejaculated all over the windowsill and down the wall. He must have dropped them because he was masturbating while watching me."
John burst out laughing.
"Oh the poor kid. Now he's terrified of what he thinks going's to happen. You weren't angry with him where you?
"No, I just pretended I hadn't noticed and said to finish cleaning up his room. I think he knew that I knew. He looked terrified."
John thought for a minute. "Do you think I should go up and talk to him, tell him we're not angry?"
"Well, remember we decided this morning that it was me who should talk to him after I accidentally caught him masturbating to porn on his computer? John I think now we should go in together to see him. That way he'll know we are united on this and that we both think it's OK for him to masturbate. I don't mind he was watching me, and I'll tell him that. But maybe if you say you're OK with it too he'll come out of his shell. We just want him to open up more and start getting the confidence to ask girls out. He's 18 now and he should be out having fun."
"Alright dear, do you think we should go up now, or later?"
"I think after dinner when he's ready for bed. He'll be more relaxed then."
Dinner was a fairly quiet affair. Joanne and John kept the conversation neutral, asking Chris about how his search for a summer job was going and about a camping holiday the family was planning. It was tough getting two words out of Chris, but his parents did their best to keep the conversation cheerful.