The Deal

"Hey Matt, how is my favorite horny eighteen–year-old this morning?" Diana came up behind her son and wrapped her arms around him hugging him close as he was reaching up to pull the cereal from the closet. Her nipples pushed into his back. He was tall enough for her to rest her head on his shoulder.

"Well a bit more horny now thanks to you," Matt placed the box on the counter and rested his hands on either side next to it.

Diana looked down at her chest pressed against her son's back and jumped back. "Oops, what can I tell you, the girls have a mind of their own some times."

Matt turned to look at Diana's full breasts with their pink nipples. "So I keep hearing. You just got up; why are they hard already?"

"Oh just some creative toweling after my shower."

She rubbed her palms across her nipples.

"You are in a grand mood this early in the morning; what's up?"

"Hey it's a beautiful day, and I have a list of things for us to do around the house to gear up for spring which should be coming before we know it."

Diana was a sun bunny and had always loved anything to do with the sun and generally hibernated through the winter.

Matt gave a mock groan "Yeah like in a month and a half. How big a list?"

"Just some tightening, hammering, wiping, storing away and ..." Diana trailed off as she watched the growing look of desperation on Matt's face.

"Well, did you have any other plans today?"

Hesitantly came the "No not really."

"Well alright then how about I let you assign the jobs between us, that way you can give me the jobs with the maximum wiggle potential?" to emphasize her point Diana shook her shoulders which caused a side to side sway of the rounded orbs on her chest.

"Hey the more you wiggle the less you can blame me for not getting anything done, remember" Matt pointed an accusing finger at the swaying breasts.

"So what will get me the most work out of you?" Diana asked exasperated.

"You expect me to think on an empty stomach? You do have spring fever – it's clouded your judgment."

Diana reached around and grabbed the cereal box and put it back in the cupboard. Again a breast pushed into Matt, the nipple poking his side.

"Tell you what; I'll make pancakes so you can get a preview of the wiggle to come."

Matt laughed and sat at the table "Wiggle away oh naked one."

While Diana bent down to get the griddle out of the bottom cabinet she shook her butt as she said "wiggle, wiggle."

Later, after much flipping and wiggling, the two sat to a hearty Sunday breakfast.

"So oh mighty muscular man of the house are you willing to help your poor old naked mother?"

"You know how a naked girl motivates me."

Matt smiled at the sexy chuckle that came from his mother's lips.

"So did you parade around the house naked for dad?"

"Not like this, but after certain bouts, one of which created you of course, we would dispense with getting redressed for the evening, or afternoon, or morning." Diana smiled at the memory.

"So you guys were pretty wild huh?"

"I don't think we were that outlandish. No worse than the rest of the neighborhood back then. We were in love, open-minded and loved to have fun."

"So anal sex, masturbation performances, and talk of threesomes are pretty normal" Matt smirked as he held up his fingers and counted off, "am I missing any thing?"

Diana pointed a finger at her son, "Hey, the threesome was strictly fantasy material. I couldn't help it if your father was an ass man. And besides, you are waaaaay too familiar with your mother's ancient sex life, Buster. And Mr. Smarty pants, you forgot the quick surprise public flashes, creative use of the girls, and the photography sessions besides other things that I am not the kind of girl to dabble in and tell about, especially to a horny eighteen-year-old." She stuck her tongue out at her son.

Matt's eyes lit up as he pondered the new found knowledge.

"I know what will motivate me for a day of cruel slave labor."

"Oh I can hardly wait to hear this one."

"Now don't get mad at me..."

Diana cut him off "You know you say that a lot lately."

"Hey I'm horny; you're naked; what do you expect?"

"Good point. So what form of debauchery has your twisted mind come up with that will stay within the boundaries?"

"Well, apparently, it's nothing that you haven't already done and only a little stretch past what we've done but yet, yes, it is still within the boundaries, oh cruel law enforcement officer."

"Alright I'll be daring. If I've done it and it stays within the boundaries I'll do it. Oh crap, I don't like the way your eyes just lit up."

"Well, remember how I said not to get mad and remember how I am always horny and even though I have as you say a twisted mind you have enlightened me to things I never even knew where possible. And now I am going nuts with curiosity!"

"This lead up doesn't bode well."

"Okay here goes," Matt's eyes dropped to the table and he rushed on "I really want to see what anal sex looks like."

Diana squeaked.

"WHAT!?! And just how is that not completely breaking the boundaries? You'd be touching me in places no son should ever touch."

"No, no. Not with me," Matt scrambled to explain.

Diana squeaked again, "What do you want me to do - grab some guy off the street – 'excuse me sir will you have anal sex with me so I can satisfy my son's curiosity'?!?"

"What? No, no. With your penis thing."

"My penis thing? Oh that. With you watching? Why don't you use the damned Internet like everyone else instead of your own mother?"

"Internet porn? That's so phony."

"I can't believe you want to watch me use my vibrator on my own butt."

"Actually, uh I'd really like to uh take some pictures."

Diana's mouth dropped wide open and she spluttered.

"Hey, you've done it with Dad; I'm not touching you; don't hit me!"

Diana's eyes were glazed as she shook her head "I've created a sex fiend. I don't know what to think. Sure, it's kind of within the boundaries but wow are we crossing some huge territory. If I say I have to think about it do I lose my work mate for the day?"

Matt figured it was time to get out of the room while he was still alive. "Even when you say no of course I'll help you. I am actually relieved that you didn't throw a plate at me or something. Just call me when you're ready to work."

Matt got up to fire up his computer for some quick play before his day was shot.

As Diana got up to think and clean up the kitchen once again the butterflies were swirling in her now full stomach.

When she finished she went into her room and sat on her bed still thinking. Shoving a seven-inch rubber penis into her own ass was not something a normal mother should do in front of her own son. Let alone the added element of him talking pictures as a record of the event. Diana wasn't worried about what he would do with the photos. His honesty and discretion with the deal had earned her trust. The act however was practically full bore extremely kinky sex regardless of his lack of physical participation.

She really didn't want to upset him. So what could she offer as a worthy substitute that stayed within the boundaries and didn't simulate sex. Use the girls on him – too much contact. Let him take posed pictures sans dildo – surely not equal enough for his apparently twisted tastes. She had already masturbated in front of him, twice actually and even once with the dildo.

So much for no simulated sex she realized. She even had stuck her own finger in her ass during the last session. No wonder he was becoming an anal freak. She thought back to that very morning when she got the griddle out of the cabinet wiggling her ass at Matt. Way to pour some gasoline on that fire girl. She thought she had heard him groan. Boy was he just like his father.

She thought about all the anal bouts with David and felt a tingling in her backside.

She also thought about when Matt watched her have one of the most intense orgasms of her life. She remembered with a twinge of guilt that it was Matt's name not David's that came out of her lips.

While she really didn't believe she was substituting Matt for his father, she had to admit the sexual buzz around the house since she dropped her clothes was a lot like her incredible time with David. And she now realized that she had missed that a lot.

She could think back to intimate times with David now without getting choked up. Crazy times. Wonderful times.

David hated to shop. So to make the experience bearable for him they had invented a simple game; while shopping David would challenge Diana to do five things and if she wouldn't do one David won. If she did them all or couldn't do one then she won. Sex forfeits were always the prize.

"Gee Di, if you're so cold in the freezer section, maybe you should warm it up. Put your bra in the freezer," David smirked waving a hand at the frozen dinner section. Diana pressed behind her through her cotton shirt to unsnap the bra and pulled it through an arm hole and then the other one. As David held the door open Diana tossed the garment in.

"You owe me a new bra, babe," she turned and started to walk away.

"Mmm, mmm. Look at those hot buns. I think the panties need to go in the bakery department next."

Diana stopped and looked over her shoulder, her long pony tail waved across the bottom of her spine "Is that a request or a challenge, sir?"

"What, worried the bakery is a little exposed for your exposure? Oh, it is a challenge babe."

Diana stared at him eyes aglow as a smirk spread on her face.

"I'm sorry sir. This establishment only serves the freshest goods open to the fresh air." As she walked away she flipped her short skirt up to reveal her panty-less ass. "Game, set, match to me lover boy," Di called as she wiggled her butt before dropping the skirt and skipping around the corner of the aisle.

Hearing a commotion David turned to see a glaze-eyed smiling elderly gentleman getting punched in the arm by an angry looking old woman. David was stunned; Di had to have known that they were there. David sheepishly smiled, waved and ran pushing the half full cart after the sound of his wife's laughter.

Diana smiled as she smoothed the folds on the comforter on her bed.

Eight years with no sex and I awaken a deranged sex fiend myself she thought. She never realized before how much she had changed since David's death.

Well, David was a great, normal guy even with an anal obsession; it probably wouldn't kill Matthew.

She decided to stop thinking so much and get back to living life to the fullest. Sadly, David's death proved you never knew how long you had.

Shaking her head, she went into her bathroom and got a bottle of lotion. Next she went over to her dresser and found the digital camera in her purse and reached into her underwear drawer where right on the top lay her old rubber little friend that she had been getting reacquainted with quite often lately truth to be told.

She sat on her bed and thought about the whiskey bottle in the kitchen cabinet before deciding to forget it.

"I'm ready for you Matt."

"Give me a second" came his answer.

She felt the pounding of her heart in her chest as she heard his door open and momentarily he stepped into her open door.

"What's first on the list, oh cruel slave laborer?"

"Here, catch" Diana tossed him her camera as she scooted up onto the bed.

"First, you tell me how you want me." Diana waved the lotion and penis at him.

"What? What do you mean?" Matt's eyes bulged out.

"Lying on my back or on my hands and knees for example."

"You mean there's more than one way?"

"Oh no; I seem to get in trouble when I share my knowledge with you. On my back." Diana laid flat, raised her legs to her chest, pushed her butt off the bed and opened her legs in a very unmotherly way. "Or on my hands and knees" Diana rolled over and got on her hands and knees. She looked over her shoulder at him. A little of her auburn hair from her short pixie hairstyle covered her eye giving her an even more sexy look to the excited teenager.

"Ah that way is fine." Matt looked down at the small red camera in his hands. Not believing his luck he added "Now when we're done I can download these to my computer, right?"

She kept her hair covered eye on him as her hand started to open the lotion, and she squeezed some onto her other hand, "Do I need to go over the rules for the very existence of those pictures."

"Trust me, no one else will ever even know they exist."

She ran her lotion covered hands around the penis. "You know that there really is no attractive way to do this right?"

"That's what makes it so cool."

"So says the one not getting anything shoved up his butt. Look, stuff like this is great between people who love each other and respect and trust each other. Which in a twisted, bizarre way is why it works for us I guess. But you need to remember that women are not pieces of meat or objects solely for your sexual gratification. We are emotional beings with feelings of our own. Always respect that and pay attention to that," she dropped the dildo and squirted lotion back onto her hand.

"Stop, Mom. Look if you're saying that you're not comfortable doing this in any way. Please don't do it. I never want you to do anything that you don't want; no matter how much I think it is cool."

"Thanks Matt. But I really am okay with this, God help me. You know, your hormones didn't fall far from the tree because I am actually getting pretty worked up over this in a very, very good way." The last almost purred out from Diana.

Matt could see that her face was turning a vibrant shade of scarlet. Again a hair covered eye peeked out at him as she spoke "Normally, the guy helps with the lubrication process; but that is so not happening buster. So that means your mother is about to stick her own fingers into her butt in order to spread lotion around – this is so not attractive or ladylike."

"Does it help if I say that I promise to still respect you in the morning?"

Diana snorted a chuckle.

Matt watched as Diana indeed brought her hand around her back and slowly pushed a finger into her anus. She moved it around before bringing her other hand with the bottle up to the base of her spine squirting more lotion onto her fingers as she pushed a second finger in. Slowly a third was added before all four fingers were sawing back and forth making a lot of squishy sounds.

"Doesn't that feel weird or hurt?" Matt asked.

Diana shook her head, her hair waving back and forth close to her face. "Anal is really a matter of preference mostly. It's really hard to describe. When you first experience it, it can hurt and a lot if not done carefully. When you have your own girlfriend and if she is inexperienced you need to progress slowly and with precautions like lots of lotion.'

She smiled at the sight of her eager son nodding his head vigorously from over her bare shoulder.

"Your dad was very much an anal freak so it became a very regular routine of our fun. I honestly quite grew to love it myself. It feels full in an odd, pleasant kind of way. Knowing it brought him so much joy it added to my own pleasure quite a lot. That's how love between close couples works. It is very mental as well."

"I love you and knowing it brings you so much pleasure like it did for your father just adds to the positive feeling for me. Trust me, I'm going to enjoy this every bit as much as you. So enough talking, it's show time."

Diana pulled her fingers out and brought her hand in front of her to grab the dildo, her thumb flicking the switch on the base. Matt could see her ass still open as a black hole in the middle of a small area of brown next to her soft white skin.

Diana held the tip against the opening. She looked up at her son who stood gaping open mouthed behind her, hands to his side. "Ah excuse me, Mr. De Mille, I'm ready for my close up."

"What?"

"Just use the damn camera Sherlock."

Diana waited until Matt had the camera at his face before she slowly pushed the seven inch shaft into her anus.

"Ung. I am so out of practice. Remember what I told you, when you have anal sex with a girl for the first time, you need to go slowly when you do this as it does feel uncomfortable at first," Diana said this through clinched teeth. "Without lubrication, it can hurt like hell."

She paused with half the shaft sticking out of her butt. She could hear the soft click of the camera. She slowly pushed in again until only the black base stuck out.

"We're going to unh let that sit for a moment." She wiggled her butt at Matt. She looked at him and watched him as he moved around clicking the camera that remained pointed at her backside.

Finally, her hand pulled then pushed the dildo slowly back and forth. The clicks of the camera came more often now.

"So, enjoying the show, my son with the incredibly perverted imagination?"

"Are you kidding me?"

"Yeah, well back in the day, your father and I had to use a bigger camera that only took still shots, no video. Don't even ask how we got the pictures developed until we could afford a Polaroid camera," Diana said all this as she slowly increased the speed of the plunging fake penis in her ass.

"Video? Shit."

Diana laughed her throaty laugh as she watched her son fumble with the camera. She laid her head down and started to strongly push the vibrator into her ass. Her breathing started to get raspy and Matt watched as more and more spasms coursed through her body.

"Oh, oh, oh, oh FUCK" Diana screamed and fell onto the bed her whole body shaking. She brought her hands up to rest on either side of her head. As she lay prone the muscles of her ass slowly pushed the dildo up until it oozed out of her ass and rolled off her onto the bed. Matt could see his mother's flushed asshole clench and open repeatedly.

"Cool," Matt cooed switching to a zoom setting.

Diana figured what he was excited about "Yuck, Gross." But the newly released unbridled exhibitionist in her caused her to drag her knees up and push her butt up and spread wide before Matt and the camera. A throaty "Wiggle, wiggle" came from the mass of hair that was all that was visible of her head. After one final wiggle she curled over onto her side, her arm spread across her scarlet breasts, smiling as he switched the camera back to stills and took one final picture.

Her sweat stained face smirked up at her son "You so owe me an entire day of complaint-free work Buster."

His rapidly retreating form yelled back "Sure Mom, after I finish ahh downloading the pictures."

She stretched her body out on the bed. Good, that means she could relax a while before another shower and work time.

She saw the humming vibrator next to her. She reached out and grabbed it and held it up flicking it off.

She stared at the fake penis.

She saw herself looking up into the eyes of David above her. Her hands held onto his shoulders as he pushed himself into her, the insides of her legs pressed against the outside of his. She felt the spark of electricity course through her body making her sob, "Oh David." He held still waiting for her. Finally he gently rolled his hips again moving inside her. She knew instantly what he wanted when he pulled back and out of her leaving a cool flush of air to gush into the void. He held still again as she compressed her stomach rolling her backside toward him. She reached her hand down to guide his hard flesh into her smaller hole before him. With a hissing sigh he glided his flesh into her ass. She wrapped her legs around his ass and her arms around his back and neck drawing herself off the bed and into his very flesh. They both lost all sense of where one stopped and the other began. He pushed and pulled through her body; jabs of tingling electricity again soared through her body crashing into her heart. Push; pull; push; pull. She felt the tremble start in his stomach and race through the rest of his body as his penis spasmed inside of her.