The Deal Ch. 09

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Diana doesn't play fair but Matt doesn't complain.
2.5k words
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Part 9 of the 33 part series

Updated 06/08/2023
Created 01/14/2017
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litfan10
litfan10
1,305 Followers

The Deal 9 -- Consolation Prize

"Yes!" Diana whooped and danced in a circle waving the Wii remote over her head. Her sweat covered breasts flipped up and down with each step.

Her son Matthew flopped down onto the black couch behind them. He looked just like the avatar on the big screen with its head down holding a tennis racket with "You lose" across the middle.

Diana bent over touching her toes flexing her stomach muscles. Behind her Matthew was given the view of her ass cheeks pulling the light blue panties taut. He dropped his remote on the seat next to him and rested his head on the top of the couch.

Diana leaned back and sunk onto the couch next to her son.

"What's going on? You're not even paying attention to my ass."

"Oh, I'm just annoyed with myself."

Diana turned to look at her son with concern "Why?"

"Honestly?"

"Of course, honey," Diana rested her arm on Matthew's shoulder.

"I am so excited that we are going to Jamaica on Spring break next week with Craig and Chip, but I am also upset that they are going which I know is wrong on several different levels."

Every day Diana was getting more and more impressed with how mature and open her son was becoming. Creating the deal whereby she was completely nude in the house with him was turning out to be the best thing she ever did.

"How so?"

"Well, you're my mom, and I am having so much fun with you. But this isn't forever. While I am in no hurry; some day we each are going to get people our own ages for the kind of relationship we ultimately want as no matter what happens between us - you're my mom and I'm your son not husband or wife or like that. So I fight the feeling that my friends will be in my way with you on the vacation."

"Were you planning on seducing me next week?"

"No, I respect the boundaries you set up on the deal. It's just that no touching or telling friends can be so hard. It is so hard to be the luckiest guy in the world and not be able to share it with any one. Even though Mrs. Lynn knows now, she is your friend not so much mine."

Matthew looked his mother in the eyes, "Now don't get mad at me, but I picked Jamaica because I found out it has clothing optional beaches and I was hoping to get you naked on the beach where I wouldn't have to hide how lucky I am."

"Why you little sneak," Diana smirked at him. "Just because I drop my pants easily here doesn't mean I would out on a crowded beach. This body has seen a lot of miles and isn't all that it used to be."

"Oh give it a rest. You are gorgeous. I see people staring at you all the time. I knew it would take some work, but that would be half the fun. I knew the hotel room would be easy in any case," Matt smirked back. "That is until Craig and Chip were able to work it out to join us."

"Do you want me to cancel with them honey?" Diana asked hesitantly because he was right in that they shouldn't become such a private couple.

"No; that would make me such a jerk to them and take us to a level that is probably wrong. I am just going to have to suck it up and, gasp, try to have a good time in sunny Jamaica with my three favorite people. I will just have to remind myself of that every time I start to feel that they are getting in the way."

For a while both stared at each other silently.

"So did you enjoy the game of cards last night? Gee, you now have the experience of two live naked girls."

"Yeah that one I didn't see coming. Do you think Mrs. Lynn will really want a rematch?"

Diana punched her son in the arm while laughing. "Oh Mr. Horny Teenager didn't get enough last night huh?"

Matt grinned sheepishly.

"I am just worried about Craig. Yesterday was out of nowhere but today; I am kind of feel guilty about Craig." Matt said this while looking down at his feet.

"You and Sue need to figure things out because it does suck to keep things from somebody. People usually end up hurt and angry. It's not like you're cheating on him, but there are still deep secrets developing. Sue is the elder. Give her a little bit of time to figure things out. I believe that she will approach him first on her own. You just need to be ready for any reaction. Who knows he might end up grateful for my little push last night."

"Cards or more with both of you and Craig." Matt grinned. "Other than seeing Craig naked that would be kinda cool."

"I believe Sue is going through a reawakening like me so I think more naked fun is definitely in the future, you lucky boy."

"What was she talking about swapping partners and that she had seen you naked lots of times?"

"Well, some groups get together for sexually parties. They're called swingers, Matt."

"Oh I've heard of them, but I didn't believe that they were really true."

"Oh they really do exist. We used to get together every couple of weeks for ... let's just call it adult fun and leave it at that."

"'We' as in you and dad with the Lynns?"

Diana smiled in memory and nodded, "Yes, with the Lynns, but also the Hamiltons and the Brocks."

Matt's eyes glazed over, "All you guys at once?"

Diana blushed lightly, "Usually all of us together."

"Wow, are you guys going to do that again?"

Diana laughed, "Oh I highly doubt it will be like the old days. Life has moved on for all of us and none of us are as young as we used to be. I think you will just see stuff like last night and what you and I do."

"What about Mrs. Hamilton?"

Diana laughed again, "Two just aren't enough for you? Kim has settled down into a lifestyle that she is very happy with so I doubt she will follow in Sue and my example. Now Sue and Jeff did swap partners pretty easily. What would you do if she came on to you? Would you go for it?"

"Huh. Me and Mrs. Lynn? Wow, I don't know. Craig would kill me."

"I'm curious; if Craig was out of the equation would you go for it? Knowing Sue, it just might come up."

"You really think so? I don't know; it seems so weird. I mean she is really nice but that is just so weird. I just don't know. Would you get upset about it?"

"Good question. I wouldn't be jealous; that's for sure. I really intend to wait until the right man comes into my life. Since you are still a virgin it would be nice if it was your future wife who became your first and only. That is such an incredible sense of shared intimacy. That is one of the reasons why your father and I never got into any of the swapping even though he wasn't my first, while he was alive he was my only. But no, Sue is a good person, if you wanted to go for it I wouldn't stop you or mind. Not that I'm green lighting you hitting on her, young man. Remember that she is married and is the mother of your best friend. Also remember, Craig actually needs to be a part of the equation if you want to have a true friendship"

"Well that certainly poured cold water on my head."

"Matthew, I am so impressed with how much older you've become. I don't think many people could do what we do without it getting all screwed up."

Diana reached over and pulled her son into her for a hug.

After a firm clasp from both parties, Matt gave an exaggerated groan and pushed Diana away.

Diana looked at him questioningly.

"Hey. I am only human. I can only take so much contact with those soft pillows that you call your girls before I need a cold shower."

Diana laughed and looked down at her sweat covered breasts. While she wasn't huge, her breasts were pleasantly full and nicely rounded. Her pink nipples were sharp pebbles that probably had poked Matt pretty hard. She sneaked a glance at the bulge in Matt's shorts that wasn't there a minute ago.

"And they are for your exclusive viewing pleasure so why would you ever want to share them with the masses of Jamaica?" Diana brought her hands down to cup around her breasts pulling them out toward Matt.

"Ha, good point. I'll try to remember that too when I get frustrated at lost opportunities in the sun next week."

Matt continued, "So now that your 'girls' have got me out of my funk how about another game?"

Di jumped off the couch which brought a very pleasant bounce to her girls. "You are on horny one."

Both jumped back and forth slicing their white remotes back and forth trading volleys.

Matt kept losing points as his eyes kept wandering toward Diana's sweat covered bouncing breasts. Di was very aware of his loss of concentration and took every opportunity to emphasize the swing of her breasts.

Finally it came down to the third set thirty to forty in favor of Diana. After a well placed shot Di waited until Matt was ready to swing his remote to send the ball back when she called his name spun around and pulled her panties off her ass calling "wiggle, wiggle."

She looked over her shoulder to watch the ball bounce past Matt's avatar untouched.

"Yes!" She called and jumped into Matt's arms. "Beat you again sucker!"

"Augh, again with the breasts! Now if you don't mind, it seems that you have done such a good job cheering me up that I need some private time so to speak."

"Matt, wait." Diana put a hand on her son's chest holding him in place.

"Look, I often forget how hard," at which her eyes were drawn again to Matt's shorts, "it is for my constantly horny-eighteen-year-old to restrain himself because you are doing it so well keeping to the boundaries. And I can't tell you how impressed I am with how you are handling these situations so maturely."

Diana looked carefully at her son before continuing, "I just got the idea for a special reward that is technically not breaking any boundaries we set but sure pushes the limit. Could you do your "private time" here with me inspiring you?" Diana got up to stand before her son putting her hands on her hips before swiveling her body down then back up in an erotic gyration.

Matt groaned and brought his hand to his groin. Looking at his mother's whirling body he slowly rubbed his hard flesh.

"Hey, I've already seen the goods mister, so drop them shorts," Diana spun in three-sixties, hands caressing her shaking breasts or wobbling butt whichever was before Matt at the time.

Matt shook his head before pulling his shorts and underwear down and off his legs. His young cock snapped back and thumped against his stomach. He started to bring his hands back to his groin.

Diana's eyes glowed in appreciation of the firm flesh before her. She quickly dropped to her knees before him swatting away his hands.

"You, sir, are not the only sneak in the family. Now this is a special treat this once. The deal we made says that you cannot touch, but I never said I couldn't. Besides, 'look ma, no hands'," Diana smirked and leaned forward squeezing Matthew's upright penis between her breasts. She pushed and pulled her flesh around his cock, together or against each other rubbing and scraping her soft flesh against his throbbing hard flesh.

"Oh my God, shit," exclaimed Matthew his body jerking at the unexpected stimulus he was receiving; his fist pounded the couch next to him.

Diana's face was all a glow as she squeezed her breasts and slid them up and around her young son's cock. Again the area on her chest bone above her breasts flushed red. She heard Matthew's breath rasp and knew he was close already. Ah, to be so young. She pushed the sides of her breasts into his cock and slid up and down as hard and fast as she could. She felt his penis spasm and watched as pulse after pulse of semen erupted up and out. Some hit her hair and her cheek while the rest went all over the floor. The last few pulses oozed out across her heaving, pink breasts which were motionless but still holding the stalk firmly between them.

Diana reached her hands down to spread the cum into her skin while rubbing her nipples at the same time. When it was all spread thin she brought her hands up to her cheek and hair wiping the cum off onto her hands which she brought to her mouth to lick clean.

"Do you really like the taste of that, Mom?"

Diana looked at the still quivering penis lying on Matt's stomach. She smirked and with eyes aglow she quickly leaned down and ran her tongue across the head of his wet cock before sitting back up to look into Matt's glazed eyes.

"Well you are only the third man's I've ever tasted, but yes I like it just fine thank you very much."

Matt's cock jerked up and rehardened quickly from the surprise contact.

Finally she leaned back and watched Matt's cock stand up straight and twitch. She jumped up and leaned into him mashing her cum stained breasts into his shirt while giving him a soft kiss on the lips. She twirled around and padded toward the door with a saucy strut.

"I need to shower if I want to be presentable to the other girls tonight. I will leave you alone to deal with the reawakening beast," she said as she left the room without looking back.

Matt looked down with glazed eyes at the mess on his shirt, his penis throbbing madly.

He shook his head and reached down to start to pull on his hard penis. Crap, life was never boring with his mother.

*

Of course thanks for reading. I sincerely hoped you enjoyed the latest escapades of Matt and Diana. Please feel free to leave a comment or email and I'll get back to you. Until next week don't forget Peter Towers and all his great work including his spin-off (sort of) of the Deal called "Further Along a Strange Request."

litfan10
litfan10
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Foxterot7aFoxterot7aover 2 years ago

Mathew has a truly loving, experienced role model in his mother. The communication between mother and son is logical and believable. It is gratifying to see that the mother realizes her son is maturing and that he respects.

rightbankrightbankover 6 years ago
I know it's finished and published

so my wishes cannot alter the storyline. but

This started as a personal motivation attempt by a mother for her lethargic son. So far we have witnessed a slow, step by step, incremental progression and mutual awakening of the mismatched couple. Yet, occasionally a potential add-on slips in.

I hope this series remains the tale of Mat and Diana. If you must open it up to include the other mothers and sons, please do it in a new and separate series. Even then I think it would be fun to be an observer during the singularly individual family units.

Less is more?

litfan10litfan10almost 7 years agoAuthor
Response to Mgenette

Hi Mgenette:

My apologies to you (and to Peter!) I love his work but I can never seem to get that title quite right. Thank you so much for putting here.

I hope you enjoyed the story.

LF

Pope1944Pope1944almost 7 years ago
Peter Towers

I looked for his story and could not find it. It turns out the title is "Following on from a Strange Request "

litfan10litfan10almost 7 years agoAuthor
Response to prop69

Thanks again prop69 - as I mentioned before - I love Matt as a character, he is such a good and patient guy. I would never, ever have that much patience which is larger why it's him and not me!

Thanks

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The Deal Ch. 08 Previous Part
The Deal Series Info

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