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The Deal 5 — The Art of the Deal

“Oh my God, that is disgusting” Diana stopped in her tracks staring into her son’s room.

On the computer screen in front of her son a video was playing of her pushing a dildo in and out of her ass.

Diana walked into the room and sat on Matt’s bed her mouth open.

“Did you have to use so much zoom? Wait a minute; I have a birth mark there?” Diana swiveled around to stare at her real naked ass.

Silently mother and son watched the video until the dildo oozed out of her pulsing ass, rolled down her body and flopped on the bed.

“Oh yuck, that is so gross,” Diana stamped her feet on the ground and covered her eyes but peeked through the spread fingers.

Matt laughed,” Just like when we watch horror movies together; you are such a faker.”

“Hey people should not watch other people getting ripped apart; and they definitely should never see me screwing my own ass with a dildo,” Diana threw a pillow at her son and pointed a finger at him.

“I swear, so help me God, that if anyone ever, EVER, sees that tape I will kill you. And then I will dig up your body, bring you back to life and kill you again.”

“Alright Miss Prissy. I will shut it off”

Matt leaned over, clicked a button and closed his media player.

Diana squeaked.

“Oh my God, you have a naked picture of me for your background? You little shit. What if Craig or Chip comes over? Now I know no one will ever see that video because I am going to kill you now.”

“Relax mom. I have two user accounts one for private time and one for public viewing.”

Diana spluttered. She looked at the picture of her ass filling most of the screen with half the rubber penis sticking out of her anus with her head just visible over her shoulder in the background.

“And why that picture? I look so, so, so … huge assed.”

“Well it’s not like I have that many to pick from. I’d be happy to take more for a wider range of selection.” Matt grabbed at the web cam on top of his monitor.

“Oh, no, no. I see the trouble that last session has gotten me into, Buster. It’s a good thing you worked your ass off that afternoon.”

“Well of course I worked my ass off considering what you did to your ass for me.”

“Ha, ha. I can see now what a bad move that was.”

“Seriously Mom, this tape is the hottest thing I have ever seen.”

“Are you kidding, I feel like I just watched a corny old porno. The only thing missing was the cheesy background music.”

“If you want I could dub in one of your old CDs.”

“You are so not scoring any points with me today, Buster.”

Diana looked up at the screen again and shuddered, “Ugh, that picture is so gross. How can you look at it?”

“Mom, I know you’re over forty, but you are still gorgeous. You have great tits, a cute face and an ass to die for.”

“Awww, that is so sweet in such a sick, perverted way.” Diana laughed. She caught the image on the screen again and still shuddered. “I’m sorry; that picture has to go.”

Matt waved the web cam smirking.

“No, no, no, no, no. Look, you got me out of my pants permanently; you’ve seen waaaay more of me than is healthy; apparently, you got me to star in a sick, kinky porno…”

“Hey, you brought up the video idea. I was just taking pictures.”

“Still not scoring any points Matthew.”

“Alright Missy I think thou doth protest too much,”

“Shakespeare? I’ve seen your English grades, who are you fooling?”

“Now that was just plain mean. Okay, I was going to let you off easy but not now. You insulted my intelligence. The background stays.”

“It goes.”



“What are you offering to get me to take it down?”

“What? Again? You conniving little shit!”

“Hey you threw the first low blow.”

“I don’t believe this. Okay mister pervert, what do you want?”

“Lots of pictures”

“Pictures; not lots.”

“You forget – I like my background; lots.”

“That’s not a fair trade – one picture for lots,” Diana tried her best whiny voice for sympathy points.

“Oh, that fake voice is so mature and effective – not.”

“Well, what else is in it for me?”


“Oh come on Mr. Negotiator, you can do better than that!”

“Uh, what else can I give you?”

Diana remembered back to the time she caught Matt with his pants down. She looked up at Matt with an evil smirk.

“Oh I don’t like that look” Matt gulped.

“Welcome to my world.”

Still smirking, Diana pointed a finger at her son “You want lots of pictures – you replace that picture with one I approve of and…”

Matt stared at her.

“You give me a Full Monty show with climax.”

“What?!? No way!”

“Going once, …”

“Wait. You give me lots of pictures and a new video.”

“Don’t you ever quit? I don’t trust your twisted mind. What sort of video Mr. Kinky?”

“Same as last time but on your back.”

“You really are an anal freak, literally.”

“Hey canlı bahis it’s your fault; you had to show me that gorgeous naked ass.”

“Again, sweet but sick.”

“Well, I, ah, jerk off in front of you, let you pick a new background and you give me a new anal video and pose for lots of pictures.”

“Define ‘lots’.”

“Until I’m tired of taking them.”

“Like that will ever happen.”

“Hey, eighteen and horny.”

“Alright, I will again assault my own ass while you video tape the twisted scene and be your own personal on demand Playboy centerfold model for probably the rest of my life or at least until gravity catches up to my girls and ass and grosses you out. But first you thrill your mom with a fully nude show. And, you clean up the mess.”

“I’ll need some inspiration, you give me the video first and I just want to drop my pants.”

“Too damn bad! Video first fine but full nude.”

“Alright full nude but we go on vacation during spring break to some sunny island. I am so sick of the winter and it’s my senior year besides”

“What? Just how many gears do you have running in your head and how come you never used them for school until I dropped my pants and started this whole mess?”

“You were the one who said “see my ass to get you off yours.”

“Yeah but I’m the one whose ass keeps getting screwed. Literally, mind you!”

Matt started counting off with his fingers “Well let’s see nude, jerk, clean, and new desktop, for preliminary anal video, lifetime supply of pictures and island vacation… and a willing participant in future videos.”

“You have got to be joking. Have you thought of running for politics? You would be very good.”

“Eww. No. Nude, jerk, clean, desktop, for video, pictures, vacation, at least two more mother approved videos – going once.”

“This sucks.”

“Going twice.”

“Seriously, I’m sick of anal!”

Matt swiveled his monitor to face his mother directly. “You are such a liar.”

Diana looked again at the seventeen-inch photo of her dildo filled ass and shuddered.

“Alright, deal.”

Mother and son stared at each other. Matt’s eyes were lit up with anticipation. Diana shook her head. “Well, I believe an ‘on my back dildo in ass video’ is the first order of business. But then your gloriously naked ass is mine.”

Diana and Matt stood up. Matt put his arm around her shoulder as they walked out the door. “Now I was thinking that maybe we could shoot the film in the living room for the better lighting and your naked skin would look sooooo good on the black couch.”

“Still not scoring points.”

“It would be easier for me to clean the couch besides.”

“I really hate you.” Diana punched Matt in the arm.

“Yeah well that is what sons are for. I gave you a sporty chance to out deal me.”

He paused with his eyes lit up.

“Oh shit, now what?”

“Sporty? Hey do we still have that high quality video camera you bought to tape me playing sports?”

“High quality ass shots? I think not.”

“So you want your ass to look all old school corny porno? You might as well give me some of your old CDs to complete the picture.”

“It’s amazing the depths of hatred that I have for you right now.”

“So crappy ass or sharp, gorgeous ass?”

“Why don’t I put on makeup and oil my body up and wear high heels while we are at it.”

“That would be so cool, Mom.”

“I was kidding, you little shit.”

“That’s at least the third time you called me that even though I’m almost a foot taller than you.”

“You — Are- A — Little — Shit.” Diana rose up on her toes and pushed her breasts out at him finger pushing into his chest with each word.

“Not even remotely intimidating. But anyways about the makeup, oil and heels don’t forget that it is going to take me some time to find and set up the camera. Think about how great you would look. If not I might as well just keep the yucky, gross background that I have on my screen now.”

“Fine — makeup, oil and heels but I expect an academy award winning performance that would do Chippendale’s proud. And no firing off in two seconds crap either! I want blisters on those hands!”

Diana turned around and walked toward her bedroom as Matt stood and tried to remember the last place he saw the camera.

“Hey Matt.”

Matt turned to see his mother in her doorway with her back to him, her legs together knees bent, both hands folded in her hair. She pushed her naked ass out at him and gyrated it “Wiggle, wiggle.” She laughed and pranced into her room shutting the door.

“And you call me the perverted one!” Matt called after her.

Matt smiled; it was going to be a very fun afternoon.

After her shower, Diana sat on her bed toweling herself. Mostly she was excited by the exchange that she had had with Matt but a smidgeon of her was annoyed with his rather arrogant attitude. It was time to teach the boy a lesson. He needed to learn that playing with fire can lead to burned fingers.

Half an hour later Matt bahis siteleri was putting the finishing touches on his makeshift film set. He had put two floor lamps on either side of the couch with the shades tilted to shine the maximum amount of light on the center of the black leather couch. Two feet in front of the couch was the video camera on a tripod. He was peering through the view finder tilting the lens when he heard his mother’s door open. He turned to watch as she entered the room.

“Holy shit!”

She had washed her hair which in short, wavy curls fanned out around her face. Matt had never seen her eyes so dark with mascara which made her eyes glow. Her lips between her blushed cheeks were painted a vibrant candy apple red which matched the five-inch heels strapped onto her feet. He had never seen either before on her in his entire life. Her entire body glistened with a deep layer of baby oil. Her body looked deliciously smooth. Her deeply tanned skin shone form the oil as her pale breasts and pelvic area sparkled in the light. In her right hand she was holding the familiar seven-inch dildo which she was rubbing across her lips.

Diana took in the scene before her, “Is all this for little old me?” She whispered in a sultry voice that Matt had never heard before.

For the first time that she could remember, her son was speechless. She strolled by him swinging her free hand out to run her fingers across his chest gently before turning to face him the backs of her legs just touching the couch.

“I want you to know that since you are cleaning up anyways I plan on making this really, really, really messy.”

She backed herself down to the couch and squished her oily butt into the seat. Slowly she brought one foot up leg bent away from her body and dug her heel point into the edge of the couch before repeating with the other limb. Her sex was splayed out in front of him.

His breath caught in his throat as he saw for the first time that she had shaved off all her pubic hair making her more naked than he had ever seen. The folds of her vagina and hole of her ass stuck out crisp and fully exposed. They practically glowed from the reflection of the light off the layer of oil.

Looking her son full in the face she brought her hand with the dildo down to her juncture and paused.

“Don’t blame me if you forget to “roll film.” Now presenting ‘Assault on Poor Mother’s Ass Volume Two — the blu-ray version'” and with that she rammed the dildo completely in her oiled ass right up to the base. Puddles of oil gushed out and dripped down the front of the couch.

Matt dove for the camera and zoomed the lens in to catch the movement of her hand. He wet his lips as he watched the hand twist in a grinding circular motion rather than a back and forth motion he had seen before.

Diana smiled at the groan that escaped his lips.

“By the way Matt, don’t stop the tape and leave so quickly this time and you might catch the part where I stick the penis in my mouth to clean it off like I did last time.”

Matt’s mouth dropped open.

Diana slowly pulled the dildo out of her ass and brought it up to her face.

“Like this.” She stuck the entire piece into her mouth and swirled it around sucking loudly.

Matt felt the pulses and then spasms as his cock erupted in his pants.

“Oh Fuck.” He shouted grabbing his groin.

Diana laughed as she pulled the dildo out with a loud plop before bringing it back down to stick deeply in her ass again. She sawed it back and forth while speaking.

“Good thing you’re young because I expect you to paint the ceiling before you’re finished for me.”

After a few obscenely squishy sounding minutes, Diana kicked her legs up and brought her knees to her chest thrusting her ass out toward Matt and the camera as she brought her other hand down and used both hands to drive the dildo back and forth harder and harder. Her heels kicked wildly with each thrust.

Matt felt his groin stir again. He knew he would have no problem filling her request later.

“Unh, unh, unh, unh. AHHHHHHH” She shrieked and held her hands in place; she paused then pushed the dildo as hard as she could up her nether passage digging in deep. Her legs and hips rocked. Finally she stopped shaking. She dropped her legs down on the ground, heels spread.

She brought the oil slimed dildo out of her ass and up to her mouth and as promised, again bathed it with her tongue before swallowing it up to the base. She slowly swirled it around, pulled it out and tossed it on couch.

“Oops, I made a mess.”

“You’re evil, you know that?”

Diana laughed. “Go ahead; mess with me to get your way!”

She looked around her before pushing herself off the couch to gingerly walk over to Matt.

“Well, Mr. Negotiator, have I successfully completed my first obligation?”

Matt’s eyes were still glazed as he nodded.

“Oh gee that’s too bad because I was up for a second take just to be sure. Your loss. I guess that means it’s my turn. Here’s some inspiration to bahis şirketleri make sure you’re up for your part.”

She wrapped her arms around her fully clothed son and slammed her oil drenched body into his, raising her left leg to wrap it around his waist with her heel resting on the back of his knee. She wiggled and ground her body into him before pushing off to stare at him.

“Gee, now it looks like you have to wash your clothes as well.”

Matt groaned.

She clapped her hands together. “Alright my young stud, you have ten minutes to get ready to thrill your mother.”

She waited until he was entering the hall before she shouted “By the way I left the baby oil on your dresser for you.” She smirked as she heard his door close. It was going to be a very fun evening.

Matt sat on his bed dressed only in his boxers shaking. He was used to her being naked around him all the time, but he really wasn’t comfortable with the idea of walking around in front of her nude. He realized it was really one-sided and unfair, but he couldn’t help it. He remembered trying to get out of it and her “Too damn bad.” He had never seen her so wild before; it kind of scared him. He guessed that he had pushed her a little too far this time. She was definitely getting back at him.

He thought about all the fun they had been having lately. He had never gotten so close to her in a natural mother son way as he was now. He was growing to really love her, in a good way, and respect her more every day. And she was coming alive before his eyes which made him feel all that much better about everything. He was the luckiest kid in the world with this deal but truth be told mom was getting a lot of benefits as well. He thought about how far they had gone from that original day when he walked in to find her naked in the kitchen and all the Wii playing the rest of that weekend to now. He knew he had the most amazing mother in the world. And hey, if he could get her rocks off like this, who was he to stop it.

Grinning he stood up and pulled his boxers off and grabbed the bottle of lotion that had magically appeared on his dresser.

Diana sat on the couch reading. Based on the lack of noise coming from Matt’s room she figured he had chickened out. Chalk one up for the mother. Suddenly loud bass music pounded out from Matt’s room and the overhead light went out sweeping the room into darkness. Next, the nude form of a glistening man spun into the room with lights flickering around exposing then hiding pieces of the body. Diana’s face split into a grin, my God he was actually going to do it she thought.

Suddenly the twin lights stilled and shone on the enlarged penis that was obscenely poking out at her. She realized that he was holding two flashlights in his hands. He put the flashlights on the ground and actually did a handstand over to the floor light that was still next to the couch from the previous session and flicking it on tilting the shade up before spinning around to do the same with the other lamp. Finally he strutted back to the center of the room before his mother. He brought his right hand down to grasp his cock.

“Mom, I have no idea what I am doing!”

“Hey, don’t stop now you’re doing great.”

“Here it is mom, ready to thrill you.”

“Whoo hoo, go baby,” laughed Diana.

He bent his legs out and gripped his penis and slid his hand up and down the long stalk.

Diana’s eyes shone as she watched him tug his penis over and over until with a groan he stretched out his legs, curled his toes and held his penis out while it spasmed ropey blasts of cum that hit Diana’s legs, the couch next to her and the floor. He shook for a moment and then stood still. Finally he stumbled over, turned and collapsed next to his mother on the couch their bare legs touching. Sweat was glistening through the oil as he panted.

Diana clapped “Bravo, encore!”

Matt waved a hand “Don’t fear I’ll be staying all week.”

Matt and Diana looked at each other grinning.

“Mom, I’m sorry. I was a jerk and pushed things way too far today. I am really sorry.”

“Yeah you were quite the little shit today for real. But hey you realized it and were man enough to own up to it. I am proud of you. But I really think we should knock things back a notch or two.”

“No problem with me as long as we can keep our original deal; I’m cool with that.”

“Oh, I don’t mind a little improvisation now and again; just not at such a train wreck speed. So long as neither of us gets hurt.”

She reached over and put her arm around his shoulder and pulled him in for a sideways hug, their nude bodies pressed against each other.

“Shit mom we’re touching!” Matt said in a panic.

“Except for the lack of clothes this is exactly how a loving mother and son should be.”

They both looked down at their oily bodies.

“Mom you shaved; what made you do that.”

“Well I was trying to be all ‘in your face’ to get you to realize that you were being very pushy. I figured no hair would make things be all out there in a raunchy way. I was going for the freak you out look.”

Diana and Matt stared at her naked pubes. Both shook their heads saying “Nah, don’t like it” at the same time. Looking at each other they burst out laughing.

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