Making the Grade

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Young man enjoys older lady.
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KEaster46
KEaster46
398 Followers

Grace Brazil & Keaster46

Christopher stepped out of the shower toweled off then peered into the semi darkness of the bedroom. The female figure was out lined by the street light as she lay sleeping. Chris wanted to go to her and gather her up in his arms and kiss her again and again. He may not have loved her but what ever it was that he was feeling at this moment it sure had him feeling good. Chris picked up his clothing and walked out into the night.

As he walked down the back alley to his home only a block away he wondered why these encounters were done mostly at night. He would be happy to have walked down to Linda's house in broad daylight if she had allowed it. This was the third such encounter and their time together kept getting better with each time they... they what. Chris wanted to say "Made love. Fucked their brains out. Went crazy in the nakedness of seeing one another." Just what was it they were doing and where if any where was this going to lead. He turned at his back gate paused to sat on the swing and think before going in the house. It was now after midnight the moon was full and it was nearly as bright as day. There was no one about in this small town. No one saw him coming from Linda's house or going for that matter. But he knew that sooner or later someone would know what he was doing with this older lady and it was not just her helping him with his math skills.

He knew that some people can simply look at a man or woman and know they have been making love or getting fucked. Some people had a glow about them that is like a bill board sign telling the world what they have been doing. Chris was not sure if it was he or Linda that would glow first but he knew keeping a secret in this town was not possible. He stood and entered his house.


He smiled to himself as he thought Linda was about the same age as his mother. He had let his mind run down that path after the first time he had come home from Linda's. He had gone to bed thinking Linda was a lot like his mother. They both were small women, both had full round breasts for their slight frames. Both were happy people with a smile on there pretty faces all the time. But the big difference was that when Chris stood close to Linda both felt this strange sensation between then.

Some one at school had said Linda Blair was available to tutor students in math. Chris had approached Linda and from that first moment he knew and she knew it was going to be much more than a simple hour of math instruction. Their eyes met and they both were pulled into a spider web stronger than steel. It tied them together and quickly bound them into one strange bundle of flesh. The older lady had not only allowed Chris free roam of her body but Linda was the one that guided the sessions and instructed Chris how to do what she liked but also it was Linda that gave Chris the first taste of her many charms.

Linda had been married before and she knew just about every thing two lovers could do to and for one another. Linda showed Chris how to excite a lady with his tongue, is fingers and of course his manly erection. Linda had told Chris that he was every bit a man in the male erection department. Linda had touched Chris that first time she had held his erection in both hands mouthing the words telling him how much she needed him and how lovely his cock was.

After that first time Linda had cried and rolled away from him. He asked what was wrong all Linda could say was she was so ashamed. Yet when Chris rolled her back over to face him she once again grabbed his cock as he kissed her. Later as Linda sat upon him with his cock pushed way up inside her with Chris looking up at her face she told him to take her breasts in his hands and squeeze as she bounced up and down.

Linda never seemed to be embarrassed again after that. Chris was so stunned that first time he never had time to be embarrassed. Linda had told him he had a very manly cock and so he relished in the glory of her words and let her touch him, take him into her mouth when ever she wanted and Chris let her mount him in any position she desired. Linda seemed to like it when Chris got behind her and did her from the back like a dog. In fact Linda had called it doggie style once.

Chris did not say how excited he got doing it that way. Chris did not tell Linda how aroused he got watching his cock going into her while his eyes looked at the tiny tanned and puckered hole just above her pussy. Chris did not say he was fascinated by looking at her tiny ass hole.

That first time when he came home he remembered looking at Linda's beautiful ass and thinking how much he wanted to put his cock in her little puckered hole. He had heard of such things and that was when he remembered seeing his mother bent over naked and how he had seen his mother's tiny butt hole. He remembered how hard his cock had gotten when that happened.

It had been a year ago. Chris was going out to pay ball with his friends but had gone back home to get something. He had gone down the basement stairs and watched his mother with out her seeing him. He watched as she bent over removed her shorts to put them in the washing machine. He was sure she believed she was alone in the house. But he had seen her bare ass and that tiny spot between her ass cheeks. Now a year later he was seeing such a spot up close and he had even touched it. Every time he saw Linda's tiny ass hole Chris thought of his mother. He could not tell Linda what he was thinking but on the other hand he could not stop himself from thinking of his mother's sweet ass hole.

Chris climbed the stairs to his bedroom still thinking of his mother and how sexy she was.


Chris was thinking of his mother much more than a young man should and of course he knew all too well how wrong it was for a boy to think of his mother in this way. But he liked to think of his mother naked lying on her bed with her legs spread waiting for him to mount her. Waiting for him to press down on her so she could feel his cock fill her pussy. Chris missed a step and nearly fell back down the stairs. He smiled and thought if I break my neck I'll never get to fuck my mother.

Chris passed his mother's bedroom door. It was ajar he paused and pushed it open far enough so he could get his head in. He wanted to just get a peak of his mother as she slept. He wanted to see her shape as he had left Linda. He thought of the out line and shadows cast by the street light. There were no street lights here but there was that night light his mother kept on near the bathroom door.

Chris's eyes were well adjusted to the dim light as he focused on the bed. Shirley was naked sleeping on top of the sheets. She was on her side facing away from the bedroom door. Chris smiled as the dim light shinned like a beacon reflecting off the twin globes of her firm ass. He could not see that tiny spot he lusted for but he knew where it was and what it looked like.

Even at this distance he could smell the scented soap his mother used in her nightly bath. Chris moved into the room kneeling at the side of the bed. His face just inches from his mother's round ass. He took a deep breath taking in the smell of her and thinking he would love to lick her little puckered hole. He was so excited his cock ached to be free on his confining jeans.

He stood dropping his jeans to the floor. He wanted so very much to wake his mother show her his manly cock and tell her he wanted to fuck her. His mind was doing all kinds of crazy thing and he was shaking all over while he jerked on his hard cock.

Thoughtless of anything else he placed his face close to his mother's sweet smelling behind. He pushed his tongue between the plump ass cheeks and touched the tiny puckered hole. For God's sake he was licking his mother ass hole. Was he crazy? What if she woke how would he ever explain his crazy behavior.

He was about to pull back when his mother let out a soft moan. He froze in position his tongue sill touching the sweet tightly squeezed hole. His mother moaned again and this time it was different it was more of a deeper more sexual sound more like when Linda was getting ready to climax. Mother was making the same deep guttural sound.

Chris titillated her anus with his tongue. His face was now pressed into the sweetly scented crack of her ass his tongue licking the anus. He could not stop now. What if she woke, what would he do. Maybe she's having a dream; maybe tomorrow she'd think it was a dream. Maybe she'll not remember it at all. Maybe, maybe, maybe and maybe she'll wake up and kill him.

Christopher was not thinking now he was moving on instinct. He had never done this to Linda. He was going crazy and he knew it but he did not care he had gone too far to stop.

Chris slipped his middle finger up under his chin and was applying pressure to that tiny space between his mother's pussy and her sweet ass hole. Chris felt the wetness of her dribbling out. His mother was very wet. He placed the wet tip of his finger to the wet tiny hole he had been licking. He applied an ever so light pressure. The tiny hole relaxed the tip of his finger passed easily into his mother rectum.

Chris was so scared she thought "Now what?" if he stopped his mother would surely awaken. He was dead no matter what he did. He pushed his finger tip deeper into her ass. His ring finger touched her wet pussy.


He thought "Oh shit." Then pushed that finger into her pussy. Not all the way but just between the wet lips.

He was fucked, he was dead he'd be in jail before morning. He was molesting his sleeping mother. Surely there was a law against that. "Oh fuck." He was so screwed. What the fuck had he gotten himself into? Chris pulled his fingers out of both holes and move back slowly. Shirley moaned but did not move. Chris grabbed his jeans and ran from the room as quietly as he could. Once back in his room he felt so sick he placed his head in the toilet he did not toss his guts but he sure felt like it.

Dressed in jeans and a t-shirt Chris approached the kitchen. He heard his mother on the phone. She was saying "I know we talked about transference of affections Doctor and I thought that was all past." Pause "No it was a dream and I'm still dreaming of my son. The sex was so real I was so very close to a climax I was all wet with a discharge this morning. We have to talk." Pause "Well alright I can wait until then. I can make that appointment. But this dream was so real. I still don't understand why I'm having sex dreams of my own son. I'm not seeing any one and no I don't want to have sex indiscriminately with just any one. I have no idea why my dreams are of sex with my son. I really don't know if he is sexually active or not. I don't see why that would make any difference anyway. Yes I will see you then. Thank you goodbye."

Chris turned back away from the kitchen door to let his mind take in what he had heard. His mother was having dreams of him and sex. Or was it sex with him. "God all mighty." this was too fucking weird.

He stepped into the kitchen and smiling said "Morning Mom great day."

He noticed his mother was visibly shaken and not her normal self. So he said "Are you alright Mom you don't look well?"

Shirley said "I'm fine I just did not sleep too well. What time did you get in?"

"I'm sorry but Ned and I got to playing that new game and I kind of ran a little late. I heard you moaning when I came in. Were you having a bad dream?"

Shirley sat down with a cup of coffee and hung her head. "It was not a bad dream just not one I want to repeat."

Chris smiled to himself and said "I've had a couple of those. But you know we can not control our dreams. I once dreamed of something I would have been so ashamed of if anyone could ever read my dreams. It was not a bad dream either it was just not something most people would consider immoral and against normal thinking. I've had it a few times and I never know when or why I have this dream. Silly I know but I kind of like the idea of it now. I guess dreams kind of change your way of thinking. Was your dream kind of like that?"

Shirley was looking at her son with a funny crazy mixed up graze over the eyes. She said "Would you tell me about your dream Chris? I'd really like to know about it."

Chris said "It was kind of outlandish but I'll tell you my dream if you promise to tell me yours."

Shirley looked at her son and thought "Chris is old enough now to under stand feelings about sex. Maybe it would do me good to get it out in the open and be honest about it."

Shirley said "If you're totally honest with me I will be with you. I think you're old enough to understand how a widow feels and that a woman my age has needs. So yes I'll tell you my crazy dreams if you tell me yours. Okay."

Chris said "I guess I have to start by telling you I'm not a virgin any more. I know you may think I'm too young for sex but it happened so let's not go there okay."

Shirley nodded in agreement and waited for Chris to proceed.

Chris poured himself a cup of coffee and looked his mother in the eye. "My first dream of this kind was shortly after Dad died. I had sex for the first time about that time. I was pretty well mixed up about sex and what to do during sex.

Jerry Becker had one of those sex movies and we watched it and I got very aroused and all that I saw started creeping into my dreams. I guess I really liked the part about oral sex. I did not do that when I lost my virginity. But the movie really gave me a lot to think about. But what was so weird was that I was now screwing every one I knew, in my dreams of course. Then one night I was really horny and I was in my bed with a hard-on and you came into my dream."

Chris paused and let his mother get the picture in her mind then went on. "I know boys are not supposed to think about their mother's in that way but it was only a dream and of course I could not control it. You came into my room and stood by the bed looking at my cock. I was so scared and I wanted to hide it but you took my cock in your hand and jerked me off.

I woke with cum all over me and the bed. I later looked this up in the library and found that most boys do fantasized about their mother and this was perfectly normal. So after that I kind of liked the idea of dreaming of us having sex. I know I was looking at you in a different way for a long time. Then I met a lady and started having sex with her and kind of forgot about dreaming about you. I leaned a lot from this lady and them after I stopped seeing her I started dreaming about you again. The only difference is now I know so much more and I've had sex in so many different ways. I was and am still dreaming of having sex with you Mom in every way I know. I've come to enjoy the thought of us having sex and I'm thrilled when ever I fuck you or you suck my cock. I've even dreamed of licking you pussy until you have a climax and I really do enjoy that.


I'm sorry about the language but its the way we talk in my dreams. I like it when you talk sexy to me. I hope you understand these are only dreams."

Shirley was sobbing and holding back her tears the best she could but not doing a very good job of it.

Chris said "Wow, Mom I'm so sorry. But you wanted to know about my dreams I did not what to hurt you in any way. I'm so sorry."

"Oh Christopher; Christopher I'm not crying because of what you've said. Its just that your dreams are the mirror image of my own. I've been so up set because of my dreams and the consequences of them have been driving me crazy. I think now that we're talking open about it I'll understand this thing the doctor calls transference of affection. I don't think it will up set me so bad any more. I really do think I'll feel much better now. I also don't think I need to see the doctor many more."

Chris looked at his mother and asked "But you promised to tell me what your dreams were about. I want to know what you dreamed."

Shirley looked at her son and said "My dreams were the same as yours."

Chris said "So tell me. You promised."

Shirley understood then that Chris wanted her to tell him the intimate details of her dreams. She heard his words all over again how he wanted to make love to her and his reaction when he thought of her. These was what some doctors say is normal when boys start to think of sex they first think of having sex with their mothers. But her dreams had come about after the sudden death of her husband and the shock of loosing a loved one.

Shirley knew all the words and had used them in the throws of passion. She knew what her son wanted to hear and she knew all too well that it would cause him to become aroused.

Shirley had talked dirty many years ago to the first boy that had taken her virginity. She liked it them and talking dirty had aroused her too. Her husband had also enjoyed the sexy words during sex. So why should it be any different with her son. He was nearly a grown man. He was still in school even though he was eighteen because of the year of school he lost after the accident he was in when his father lost his life. He had just admitted he was having sex with an older lady and he knew a lot about sex. But Shirley felt that for Chris it was more than just words she got the feeling Chris was really serious about having sex with her.

For one second she allowed herself to remember the dreams she had early on just after the death of her husband. They seemed so real and she remembered in detail how aroused she had become. All the crazy dreams flashed though her mind as she looked at the broad shoulders of her son and knew he was all man. He had been with more than one lady. She had a flash vision of her son deep between some woman's legs.

Shirley said "Oh, all right I did promise. First would you tell me who the lady is that you've having sex with?'

Chris smiled and said "Later Mom later. Now get on with your dreams."

Shirley poured another cup of coffee and after she took a sip she smiled and said "The first dreams I started having were just a few months after Father died. You were still in that body cast and needed help getting to the bathroom. At first helping you was simply a job a loving mother was doing for her son. But then the dreams started and each time I took you penis in my hand I got aroused then later I would have a dream of having sex with you."

Chris said "Tell me about the sex. What kind of sex?"

Shirley said "At first it was just mildly arousing with me touching you. Then one night I dreamed of having oral sex with you and I climaxed in my dream. That was when I started seeing Doctor Bruck. He said it was all normal and I should not worry about it too much. But for awhile they got pretty intents. I got to wanting to dream and I let myself enjoy having the dreams." Shirley looked at her son and knew he wanted more details so she said "I dreamed of us making love all over the house. Sometimes it was with the cast on and sometimes with it off. Mostly when I dreamed of you in the cast we would have oral sex.' Shirley smiled and said "I enjoyed sucking you cock and I liked you coming in my mouth."

This seemed to brighten Chris's eyes and a smiled formed across his wide mouth.

Shirley felt a pang of sexual desire shoot through her like a bolt of lightening. But she pulled herself together and went on.

I'm only guessing here but about the same time as when you started becoming sexually active my dreams seemed to subside. I think somehow I knew you were having sex and I no longer had the dreams. I talked to the doctor and he said they were passing normally.

Then here lately I started again with more vivid dreams and I've started masturbating during the day. I had a dream that was so vivid I woke up all wet and I think I had a climax in my sleep."

Chris said "Mom did you dreams I was licking you? I mean did you dream I was licking your anus. Was I licking your ass and fingering your cunt at the same time? I've wanted to do that for so long. Mom I have wanted to fuck and lick your pussy and ass. It drives me nut wanting you so much."

KEaster46
KEaster46
398 Followers
12