Meeting the Maddisons Ch. 07

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I help Chris and his mum with sex education.
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Part 7 of the 9 part series

Updated 10/30/2022
Created 12/14/2011
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Two days the phone rang. I picked it up. It was John.

"Hi Jim. Thanks again for a great night. Your family is incredible and it did wonders for Chris's confidence."

I wasn't surprised. Having one beautiful woman lick your ass and caress your balls while you're fucking another beautiful woman will tend to do that.

"That's good," I said, wondering where this was going.

"Jim, I've talked with Joanne about helping Chris build his confidence further and learn how to be with women. She feels he still needs more help as he is very shy. Well, we'd like to invite you all over for dinner. Maybe you can talk to Chris, explain to him how to get on with women. He doesn't listen to me, and, well, Joanne has certain standards and, er, doesn't want to overstep the boundaries in going too far in educating him."

"I don't see how I could help beyond what he's already been part of. You know my mum is open to sex of all sorts, but if Chris doesn't want to stand up for himself then even she can't make him."

"No, no, that's not what I mean. Joanne really wants to help Chris, but she's reluctant to go any further in helping him personally with his sex education. Jim, Chris has always looked up to you. Joanne was thinking you might be able to demonstrate things for Chris, show him what to do."

"What, you mean with your wife?"

"Well, yes, with Joanne or with your own mother. Could you come over for dinner tonight?"

"I'll have a talk with mum and dad and ring you back."

I wasn't too keen about this. I am all for sex and having a good time, but I didn't see myself going into sex education. Chris was a bit of a drag, and I didn't really feel like putting myself out for him, let alone presenting him my mother to fuck. Dad wasn't home so I decided to talk it over with mum.

"Jim, aren't you being a bit selfish about this?" she said. "You were a bit of an innocent before the Maddisons took you into their family fun and games. I mean you weren't a virgin and shy, and you got on well with girls. But it sounds like Chris needs help. If I'd noticed he was so shy that night I would have tried to help him get over his shyness. But as you know I was a bit preoccupied with so many men that night. Sally and Jennifer certainly looked after him, but sometimes men need other men to lead by example."

I thought about it for a while. Joanne certainly was hot when she helped out at school, and John seemed keen for me to 'demonstrate' sex with her, whatever that meant. Mum said she couldn't go to dinner that night as she and dad had some important corporate function to go to. Since she'd started sexing up her work clothes she'd been invited to a lot more corporate functions. This one was important as another firm was keen on getting her to join them, and a promotion was in the wind.

"Why don't you go by yourself? It'll show Chris a young man of 18 can function on his own, without his parents being there. Besides, I remember Joanne from school functions, and she was quite a hottie."

I rang John back and said I'd come, but mum and dad couldn't make it. He seemed happy with that, and said he'd pick me up at 7.

I watched mum getting dressed for her corporate function. The office clothes she wore nowadays were all quite sexy. But they were carefully selected so that they weren't overly revealing. They showed off her curves and hinted at her sexual availability. She showed a touch of cleavage and her tight skirt fell to just above the knee. When she sat down it rode up to 'accidentally' reveal much of her shapely thigh. As she'd worked hard to shape her body into a spectacular hourglass figure, she'd bought tighter jackets and skirts. She was usually in a see through shirt under the jacket, with a lacy bra. When she took the jacket off she was a knockout. She said nobody at work knew of her new sexual freedom. It wasn't that she was ashamed of it, but she didn't think they'd understand. A few men had tried flirting with her at work, but she'd reacted coldly to them, keeping it professional. I thought it probably only made them more determined.

Mum and dad had already left when John arrived at 7 to pick me up. He was alone in the car.

"Chris seems to suspect something might happen tonight with his mother and he was too nervous to drive over with me. Joanne and I are really worried about him. The truth is Jim, I hope you can help Chris become a man and show him how to take the initiative. The good thing is Joanne is prepared to help, but I'm not sure how far she'll go."

"Well let's see how it goes John. Maybe you are just pushing him too hard. Sometimes it's best to let things develop naturally."

I didn't really like John. He was clearly pushing his son too hard, and he seemed to expect his wife to perform for him and do what he wanted, more than having any real concern about Chris's manhood. I wasn't keen on being part of all that. I much preferred the Maddisons who were all very much into sex and had no hang ups about it.

But when we arrived and I saw Joanne for the first time since school, all that moral concern went out the window. She was stunning. A true MILF. Straw blonde hair cut into a neat bob, green eyes and a pretty face that defied her being in her late 30s. She had a long lean firm body with flat belly topped off with sizeable breasts. Her tits were pushing against a tight cotton shirt tucked into jeans that looked as though they'd been painted on. I couldn't wait to get something going with her.

She shook my hand nervously, then kissed me on the cheek.

"Nice to see you again Jim. You probably don't remember me, but I saw you a lot at school when I volunteered in the canteen and on sports days."

"Oh yes, I remember you very well. You lit up the school on the days you were there."

Oh you charmer, I thought. Joanne beamed at that compliment, and looked at John and Chris to make sure they'd noticed how a young man could charm an older woman.

"My Jim, you have grown into a handsome young man with great charm. Come and sit with me over here on the couch."

I sat next to her. Chis took a nearby armchair.

"Can I get you a drink Jim? Wine, beer, soft drink?" asked John.

"Rum and coke would be great thanks."

"Wine for me dear," said Joanne.

John raised an eyebrow to Joanne, and he asked Chris to help him to get the drinks. While they were out of the room Joanne turned to me and put her hand on my thigh.

"Now Jim, John and Chris have told me about the amazing night they had at your house with your mum and dad. I want you to know I was happy Chris finally got to lose his virginity, but I'm concerned about the relationship you have with your mother. I remember her from school and I'm surprised she'd be involved in anything like that. I was hoping she'd come along tonight so I could talk with her, but I must admit I am quite shocked."

She hadn't mentioned anything about her husband fucking my mother in the ass. Maybe John hadn't told her the whole story.

"My mum makes her own decisions and she decided to embark on this new liberated life," I told her. "She is doing it willingly, and she wants me and dad to be part of it."

Joanne started asking me the most detailed questions of what I had done with my mum and dad. She was keen on knowing how far we had gone. She was clearly very excited at the thought of a son having sex with his mother. Her face and hands were getting sweaty. Drips of perspiration ran down her chest and into her cleavage.

"I worry about Chris and how he is with women. He's very shy and clumsy and I really want to help him. But I don't think I can do what you do with your mother. That's incest, and I just can't bring myself to do that. I've helped Chris with masturbation, you know, jerking him off. I know John is keen for me to go further with Chris, but I just feel it would be wrong. What do you think Jim, am I wrong?"

"Well I don't think anybody should be pressured to do anything they don't want to. Everything we do in my family is by consent. It's our way of expressing our love for each other. But if you don't want to go further with Chris then you shouldn't."

"I'm glad you said that Jim. John can be a bit fanatical about things. But I still want to help Chris learn about women. Now, John and I have talked about this and we agree it wouldn't be incest if I had sex with you in front of Chris to show him what to do. Would you...would you be prepared to do that Jim? I hope I'm not pushing myself on to you."

"No, er yes, of course....you are a spectacular beautiful woman and I'd love to make love with you...."

Is she kidding? I'd give anything to fuck this beautiful woman even if the whole city was watching. It would even add a bit of spice. Since the Maddisons and mum's party I'd become quite partial to screwing in front of others and watching others do it in front of me.

At that point John and Chris came in with the drinks. I suspected they had dawdled to give Joanne more time to talk with me.

"Good news John, Jim is prepared to help out with demonstrating to Chris what to do with a woman."

"Oh that's great, thanks Jim. Chris, this will be something really special. I hope you learn something from it."

"Yes dad, er thanks Jim," said an embarrassed Chris.

"But we ought to eat and drink first," said Joanne. "We invited Jim over for dinner and I know teenagers are always hungry."

Dinner was bizarre. Even though we all knew in a very short time I would be fucking Joanne in front of them, we talked of me starting architecture at university. Chris hadn't yet decided what course he wanted to do. His dad was pushing him to do accountancy because he'd make lots of money. His mum wanted him to do psychology. I thought with parents like these if he did psychology he'd probably end up being his own best client. But I held my tongue. Joanne's shapely body was beckoning to me across the dining table.

When dinner was over, John told Chris to go into their bedroom and wait for us. John issued us his instructions: "Now Jim, I want you to go slowly, showing Chris exactly what you are doing with Joanne. I want you to lick her, kiss her, caress her exactly as a man should in foreplay with a woman. Then when you have sex and insert yourself inside Joanne, I want you to demonstrate several positions before you are ready to cum. But don't cum inside her. I want you to cum over her body and face so that Chris can see how a woman enjoys a man's sperm."

He turned his attention to Joanne.

"Joanne, it's important you demonstrate to Chris that a woman enjoys a man's penis. Show him how a woman responds to proper stimulation. I want you to cry out and have as many orgasms as you can. When Jim ejaculates over your body and your face I want you to show how much you want it and like it. Is that understood?"

What an asshole he is, I thought. Dad had told me John had served time in the army, and here he was still ordering people around. But I really wanted to fuck Joanne, and if she was happy to go along with this circus then who was I to complain.

"Oh and one more thing," John said firmly. "No anal, definitely no anal sex. Joanne, your ass is off limits tonight."

That proved to me John was a real prick. He'd happily fucked my mother in the ass, but now he was banning me from doing the same with his wife.

"Right honey, no anal," said Joanne, but when John wasn't looking she winked at me. Maybe Joanne wasn't the obedient little wife after all.

We went into the bedroom. Chris was sitting on a chair positioned next to the bed. One side of the room was a giant mirror so he could see both sides of whoever was in the bed. I looked up and there was even a mirror on the ceiling. John certainly liked the scenic route.

"Now Chris, I want you to sit quietly and take note of what happens here tonight, John said. "I want you to remember how to treat a lady, how to make love to her, how to care for her, how to worship her body and pay proper respect to her wishes. You can't be a real man until you learn these things. Your mother wants you to learn, and she's doing this demonstration just for you."

I stood there beside Joanne feeling rather stupid, but I was turned on at the prospect of screwing this attractive woman, even if it was in front of her dickhead husband.

Joanne turned to me and put her arms around my neck. "Just pretend no one else is here Jim," she whispered. "Just make like it's only you and me."

I nodded and she leaned in to kiss me on the lips. She opened her lips and slipped her tongue inside my mouth. My hands were on her hips, and I pulled her in close. Our groins were grinding into each other as our kiss went on and on.

"That's always a good way to start Chris," John commented to his son. "Kissing is quite arousing and then you feel the woman's body through her clothes, your hands asking if you can go further. You don't actually say it, but if she stops you then you know she doesn't want to go any further. Mind you, you don't stop there, but keep on trying, go for a feel of her breast or hump up against her so she can tell you have an erection."

Holy shit, was this dickhead going to give a running commentary all the way? I wanted to tell him to shut up and piss off.

Joanne whispered softly in my ear: "Ignore him Jim, just pretend he's not there." She kissed my ear and ran her tongue around my ear lobe as she ground her pelvis into my hard erection. She started undoing my shirt, kissing my chest as the buttons came undone. I reached around and grabbed her ass, pulling her in closer to me. The buttons were all undone, and she pulled the shirt off my chest and down my arms. I moved to do the same for her. I undid the buttons to the bottom of her cleavage, and leaned down to kiss the mounds of breasts that were exposed.

I could hear John in the background going on to Chris what a real man did with a woman. I managed to shut out his voice as I undid two more buttons of Joanne's tight shirt down to her navel. I pulled her shirt apart to reveal her very respectable breasts bursting out from her black lacy bra. I removed her shirt and bent to kiss all that I could see. Joanne ran her hands through my hair, pulling me in closer to her.

Her hands reached down and undid the buckle on my trouser belt, then the button holding them together. She tugged down the zip, opening my pants.

My dick was sticking straight up under my briefs. Ever so gently and softly, Joanne stroked her fingers along my erection, circling the head so softly I could barely feel it. It made the cock head jump. I looked down at her hand working its magic. The gold wedding ring on her finger gleamed in the soft light of the bedroom.

"I think we need to get more comfortable," she whispered. She sat on the bed facing me and gripped my pants at the hips, pulling them all the way down. I kicked off my shoes and stepped out of my pants. I reached down and ripped off my socks. There's nothing worse than making love with your socks on. I put my hands on Joanne's shoulders to have her lie down on her back. She had long boots on over her tight jeans. I unzipped her boots and took them off with a flourish. Then her socks which I threw to John. Joanne giggled. I undid the top button on her tight jeans and unzipped them. To get them off I had to stand and tug while she wriggled. Bit by bit they slipped down her legs. We both laughed at the ludicrousness of the moment. John wasn't happy about that and grumbled quietly. He wanted it all to be deadly serious.

Joanne was now in panties and bra. I was in my underpants, my erection poking out like a tent pole. Joanne sat up and I reached behind her to undo her bra. The lacy thing fell forward and off her arms. I took hold of it and threw that to Chris. The poor kid looked more embarrassed than ever, but Joanne's breasts were absolutely perfect. They had just enough weight to hang slightly, pink nipples standing stiff. I massaged them, kissed them gently and sucked on her nipples. Joanne groaned, rubbing her hand through my hair and over my shoulders and back. I pushed her gently to lie on he back. I kissed my way down from her breasts to her chest and stomach. Joanne's breathing was getting quicker and deeper. I licked inside her navel and kept on going down. He panties were black lacy and semi-transparent. I saw she had a bit of pubic hair above the slit of her cunt. It had been a while since I'd seen pubic hair and I was curious to see more. I kissed all around her stomach, her hips and the tops of her thighs. I hooked my fingers into the top of her lace panties and pulled down slowly. A thin line of blonde pubic hair appeared as I pulled them further down. Wow! A genuine blonde! I pulled them right off down her legs and there she was, lying naked before me. She had what's known as a landing strip of pubic hair, a trimmed thin line of hair that stopped just above the start of her slit. The rest of her cunt was completely bare of hair. I looked up at her and smiled.

"Just the way I like it," I said.

"I'm sorry, I can't bring myself to shave it all off," she said. "I am a grown woman and women have pubic hair. If I take it all off I'll feel like a little girl, so I leave that strip."

"Believe me Joanne, no one could ever mistake you for a little girl. You look absolutely beautiful," I said as I lowered my head and licked her cunt from top to bottom.

"Jim, this isn't fair. Get those off," she said pointing to my underpants. I stripped them off in one motion, throwing them to John who had moved closer to the bed to get a better view. My underpants landed on his head, interrupting his massaging of his prick through his pants.

I didn't care how annoyed he was.

I returned to Joanne's cunt, spreading her legs wide, and slipping my tongue into her gash. I worked my way around her cunt for some time, sucking on her clitoris and jamming my tongue as deep into her vagina as I could. Joanne's breathing got heavier and heavier, until she let out a cry and closed her legs around my head. I had brought her to orgasm.

John was busy explaining to Chris what had happened, and how important it was to bring your woman to orgasm as many times as you could.

I felt a tap on the shoulder and looked behind me. It was John. He wanted me to move aside from Joanne's juicy cunt for a few seconds so Chris could get a good look. John pointed out to Chris his mother's clitoris, her pussy lips and the vagina opening.

"Right Jim, thanks for that. Carry on."

What a real dickhead this man was. I wanted to thump him, but Joanne reached down and pulled me up to kiss me.

"Forget him, it's just you and me here," she whispered. "Now it's my turn."

She worked her way down my chest, kissing and licking all the way. When she got to my cock sticking proudly up in the air she started at the base, licking it all over, sucking on my balls and then licking all the way up my cock to the head. She wasn't using her hands at all. Just her lips and tongue. She positioned herself over my cock and took me into her mouth. It was warm and wet and wonderful.

She looked up to her son.

"Chris, this is how a woman sucks cock," she told him before she took me into her mouth again. "You can masturbate while you watch me if you like."

Chris wasted no time dropping his pants and grabbing his cock, his eyes almost popping out of his head as he stared at his mother sucking my cock.

Joanne warmed to her task, forcing as much of me into her mouth and her throat as she could. She was taking it down to the last inch, working up a good lather of saliva as she went up and down. Her hand was massaging my balls. Occasionally she would let me leave her mouth and lower her head to lick and suck my balls. A couple of times her tongue slipped under my balls to lick that highly sensitive line between balls and asshole.

I was close to coming. I reached down and rolled over to lay Joanne on her back. She smiled at me as she spread her legs wide and put her arms around my neck. I lowered myself into her, entering her sopping wet vagina and into the warmth beyond. Joanne raised her hips to meet me, and began a slow undulation, meeting me as I made long deep thrusts into her.

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