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Jake's Perversions

By: aishagrey



Jake was an 18year old boy that like most teenagers his age battled with raging hormones all the time. It seemed he was always horny and just the gentle breezes blowing his way was often enough to make his dick stand and salute. When not otherwise engaged in school or sports he thought of sex 24 hours a day 7 days a week. He was always looking for new ways to indulge in his passion and quench his thirst for the release he needed. Although he masturbated at least 3 times a day he never lost the urge to do it again. Only the social activities of life prevented him from masturbating more often.

At school he was often dreaming about the girls in his class, walking across campus or sitting in the library. He had sexual thoughts for some of his neighbors and even strangers in the street. If it was female he took the time to at least look and if she was well endowed then he might stare and follow her for as long as he could. He was always looking for a way to catch a glimpse of a girls cleavage if she bent over, 'accidentally' bump and maybe cop a feel of a girl coming in or out of class. Even some of his friends called him "The Perv" for his obvious actions.

So when one morning as he woke up to get ready for school his mother walked in to make sure he was up. Unfortunately he was 'up' and it was pretty obvious looking at the tent in the blankets. He saw his mother's eyes glance at the blanket and then tell him to get up and pee if he needed. Embarrassed, he yelled to his mom.

"I need a little privacy and I am awake, just leave!"

With a little giggle his mother left him to change and get ready for school. She told him breakfast was ready and it would only get cold if he dilly-dallied. 

At least it was Friday. He got ready quickly and headed to the kitchen to eat. As he ate he looked his mom over, he'd always had a thing for a thing for his mom but could never admit to anyone, much less to himself. Still he found ways to observe her without her noticing. At 42 she was still a good-looking woman, her firm breasts, he learned by rummaging the laundry were a 42 D and she was slim, had a waistline a teenage girl would die for. Jake thought that her best asset was just that, her ass. It was it a full ass but firm and together with the rest of her body she was the "MOM" all his friends called a MILF. (Mother I'd Love to Fuck). When she went to work all the young guys and older men would stare as she walked past.

This morning Jake woke up extra horny. He already had masturbated once and he still was semi erect. Watching how his mother's ass looked under her nightgown was not the type of activity that would allow his cock to go soft, in fact it had the opposite effect. He was able to see how each cheek of her ass came together and the panty line just above her ass helped define the area. His thought was interrupted when his mother said.

"Honey, it's time to go, or you'll be late for school."

As he realized he was going to be late, Jake ran out of the house. He was wearing sweatpants, loose boxer shorts and a t-shirt since he had gym today. He had to hurry to make the public bus to get to college. It was rush hour so as he made his way to the bus stop he knew it was going to be full of people going to work or school etc. His mind was already thinking of how this could be an advantage to him. Then he noticed her. She was going to be his victim for the day. She was older probably the same age range as his mom. She was wearing a long skirt that hugged her body tight and he could see the dips and curves of her ass. As she waited for the bus, Jake positioned himself to follow her onto the bus. It didn't take long before the bus had come and everyone rushed in to climb in. No one wanted to be left behind for fear that they would be late to there jobs or appointments. Jake made sure to work himself to where he was right behind the woman on the bus. As people kept pushing their way in he took advantage of his position behind her allowing himself to be squeezed closer and closer to her.

He was in heaven as the crush of passengers had him so close to her that his semi-erect cock was nestled in the middle of her round firm ass cheeks. Although she didn't look back it was obvious she could feel him. As she shifted a bit he knew she felt his cock growing hard in his pants. Jake acted as if nothing was happening and he stared out the windows just like everyone else. If asked he could always say it was just a casual bumping of the two bodies on a crowded bus, he could not control it! 

As he glimpsed down he saw his crotch pressed into her ass. He had gotten braver and he was now taking every opportunity he could find to push his cock into her ass. Each time the bus started or stopped the force of the change in motion he would not only allow his body to push into her, but he also pushed as well just to make sure he was as impacted in her crack as he could get. He thought he could notice some signs of discomfort as she glanced back at him and try to squirm away from him to no avail. Whenever she looked back at him, Jake would play it off by looking the other way. When she wasn't looking he would stare down again and see how his hard cock was almost encased between her ass cheeks.

Her reaction said it all. She seemed desperate, disgusted and annoyed. She would keep looking for someplace to move but this only made Jake more excited because every time she would move, even slightly, he could feel her ass clinch around his cock. This made him push his crotch area more into her ass, very softly each time, but when the bus jerked violently or bounced he would do it vigorously. It wasn't long before his stop so as he made his way to the door of the bus he gave her one last poke just to feel her ass cheeks squeeze his cock one last time. She looked back in amazement at his impertinence. Although she was certainly glad that he was getting off she was still disgusted be what he had been doing to her. She refused to believe that is was just accidental, she knew she had felt him deliberately push his cock into her.

As he walked off the bus, he tried to hide the huge erection making a tent in his pants. He ran to the gym and straight to the bathroom and he jacked off furiously releasing a blast of semen all over the floor.

The remainder of the school day was uneventful he couldn't wait to go home and enjoy his weekend. He took a shower as soon as he got home and when he was finished he went to the kitchen to warm up some food for dinner. 

Later when his mother came home from work she asked Jake how his day was but Jake was too caught up in his mothers breasts. They were popping out the front of her blouse and his eyes were popping out of his head staring at them. She told him good night since she had to go to work early tomorrow. She said she would take a quick shower and hit the sack early. 

Jake said good night to his mom and told her he was going to watch some TV for a while longer. Well minutes later Jake was laying on the couch, his eyes were glued to the TV watching a program, but his mind wondered away. It was back on his Mother's firm ass. He could not help thinking it was his Mother's ass he had rubbed against on the bus that morning. Combine those images with the sight of her melons popping out of her blouse earlier and Jake was aroused again.

He was stiff as an iron rod. He could not stop imagining all that stuff. Eventually it hit him. Mom is a heavy sleeper! Why not go grab a peek while she sleeps. So he did. He was already stroking his cock as he peeked through the crack door of his mother bedroom room. She was fast asleep wearing her small nightgown and lying on her side with her back facing the door. He wasn't positive that she was completely asleep so he waited another a half an hour. This time she was lying face down and he could see she was deep asleep. He slowly crept into the room this time so exited he could feel the pounding of his heart. He stroked his cock harder as he admired how beautiful mother's body was. Her nightgown was so short it pulled up a little letting him see the bottom of her ass cheeks and how they filled her panties. 

He couldn't help himself he started to slowly lift his mother nightgown exposing her firm silk pantied covered butt. Oh my god he whispered to himself as he continued stroking his cock harder and faster as his heart raced. He was quickly reaching a point where his release would be soon. He hoped she didn't wake up because he had no explanation for this insanity. But her ass was driving him crazy. He had never ever considered doing something like this but his hormones were ruling his brain and lust was blinding him. He crept closer and got up on the bed all the time telling himself not to push it this far. 

Now he was stroking his cock frantically while watching her ass and hoping that his mother wouldn't wake up. He was at the point of orgasm, he couldn't hold it anymore and he started shooting and spraying streaks and streaks of cum all over his mother ass and panties. His body jerked with each explosion as globs and globs of semen were forced from his cock forming pools on his mother ass. He was in ecstasy and his body shook and he closed his eyes in pure pleasure as he watching his own man juice covering his mother ass.

Jake's Perversions Ch. 02



Jake realized that he could not leave his cum there and he got a washcloth and wet it with warm water and a dry towel. He gently wiped his mother's ass cleaning it as best he could then he dried her with the towel. He was amazed at how erotic just cleaning his cum from her ass was and what a rush the whole adventure had been. By the time he returned to his bed he was hard and needed to masturbate again. At least he already had the towel.

When Jake got up the next morning he was still thinking about the event with his Mom and he had to go to the bathroom and jerk off again before going down to the kitchen for breakfast. He walked into the kitchen in his boxers and a t-shirt to see his Mom was already at the stove making some eggs. She was dressed only in her short nightgown she did not expect to see Jake up so early. She normally would have covered herself with her robe but it was still in the bedroom. She decided that it was only her son and discounted any notion that he would even notice.

Well Jake couldn't stop watching his mother's ass and her massive breasts each time she moved. He would rub his cock under the table until he was hard as a rock. His mother kept chatting with him about this and that while at the stove. She was oblivious to his thoughts and to where his eyes stared. With out thinking he got up and approached her from behind and gave her a hug. He immediately positioned his hard cock between the crack of his Mom's ass. She clenched her but cheeks squeezing his cock in a reflex that occurred before she could even think about it. Quickly trying to gain control of the situation she asked Jake.

"Wow what was that big hug for?"

"Just because I love you Mom!"

Responded Jake. Then his Mom said

"Then she said well go pee or something before you hurt your self!" 

She still felt his stiffness poking her in the ass. He laughed and left the kitchen to get ready for his day. He had a lot to do and after he left the kitchen his mom reached around and pulled her panties out of her ass.

No matter what Jake did that day he spent most of his thoughts on his Mom. He kept seeing her in her nightgown and seeing his cock spurt his cum allover her ass the night before. He knew that he would be doing that again just as soon as he had the chance.

A week passed and the opportunity to jerk off on his Mom's ass did not happen. It was always something, either she had trouble falling asleep or something would come up that would prevent him from going to her room. His patience finally paid off as his Mom began to put in longer and longer days at her job. Combined with the fact that her boyfriend was out of town on business for a couple of months, his Mom started to come home, eat and go to bed. She was working so hard she was exhausted and though she would always try to spend at least an hour on the phone with her boyfriend and some time with Jake, she was conked out early just about every night.

It was not long after this routine started that Jake once again walked into his Mom's room after she had been in bed for a while. He whispered her name and asked if she was awake but she was so deeply asleep that she never stirred. She just took a shower and was so tired that she didn't even bother to put on her nightgown. She was still wrapped in her bath towel.

Jake tried to wake her, he tapped her shoulder and jiggled the bed but she was out cold. There was not response to anything he did to wake her. Her heavy breathing told him she was in dreamland. He was so excited he felt as though his body was shaking. His cock was at full attention already pushing out the front of his boxers. As his mother gently snored he got up on the bed and slowly pulled down the top of the towel that was covering her huge breasts. They sprung free as soon as he moved the towel. They were firm but still lie on each side of her body because of their weight. He started squeezing them gently. He took one in each hand while paying attention to her face to see if there was any signal that she was waking up. There was no indication that his Mom felt anything that he was doing. Her breasts were beautiful. The nipples were dark pink and the breast itself was without blemishes. He couldn't hold back and started sucking on each of her nipples them while he stroked hard his cock with his hand. After a few minutes of doing this he got up and pulled his boxers off completely. This time he wanted to see how far he could go. Still shaking he stood up above her both of his legs on outside of her legs. The he sat knelt gently positioning his cock right between his mother breasts. Oh yes it was a great feeling as he moved his cock gently up and down the valley between her breasts while pressing both of them together. When his mother let out a soft moan it scared the shit out of Jake. He was frozen thinking she was waking up. He stayed as still as he could and she never opened her eyes or anything.  She just moved her head to the other side and kept breathing deep still in a deep sleep.

Jake was relieved. He kept thrusting slowly up and down while squeezing her breasts together. OMG he was in heaven. It didn't take long for him cum. He started shooting his load all over his mother chin and neck. He struggled not to get any on her but it was a hopeless cause as his cock spewed semen all over her. He found that it just turned him on more to see all his thick white semen on her chin and chest. 

He got up and hurried to get a warm cloth so he could clean her before she woke up. As he was cleaning her he realized she had a bottle of pills by the side of the bed. He saw that they were to help her sleep. He now knew why she was in such a deep sleep.

The next morning he told her he had gone into her room and saw the pills and asked if she was sick. She told him she was healthy and that she takes them now and then to help her sleep. She did not need them every night. So Jake knew for sure that his Mom was oblivious to all of what happened the night before.

Jake stopped in to see his Mom as she dressed for work and as usual came up behind her and gave her a big hug. He made sure his cock was pressing between her ass checks. Because she was wearing a dress skirt she did not notice his cock like she did the other day. As Jake unwrapped his arms from his Mom he copped a feel of her breast. She moved quickly away and busied herself with dressing. When she thought of what Jake had done she discarded it as youthful play.

Over the next couple of days Jake was not successful in taking advantage of his sleeping Mom. Either she was still awake when he fell asleep or she wasn't in that deep of a sleep. When he checked her one night he saw that she did take the pills. However she was not as deeply asleep as Jake liked and all he did was to caress her breast and suck on her nipples for a while. That night he shot his load on the floor. 

His frustration of not being able to find the right time to play with his Mom's body was making Jake bolder. He was also becoming impatient at the same time. Then the night he was waiting for came. It was a Tuesday night and his Mom had worked late. When she came in she was so tired that all she had time to do was shower and go to sleep. He was hoping she would go to sleep naked but he realized there was no chance of that. He walked to the bathroom when she called out his name and said.

"Jake, sweetie can you bring me two pain killers"

He answered.

"Sure mom, got a head ache?"

She replied yes as he open the medicine cabinet and saw the bottle of sleeping pills. He decided that instead of giving her the painkillers he would give his mom the sleeping pills. He hoped they would knock her out, put her in a deep sleep and also relieve the headache. The sleeping pill did the trick and it wasn't long before she was out. Her being so tired combined with the two pills left her sound asleep face down on the mattress. Jake could hear her heavy breathing as she lay there in her silk nightgown still on top of the covers.

As he looked in the door, his dick was rock hard. He immediately dropped his boxers on the floor and walked into the room. As always he started by whispering and calling her name to make sure she was deep asleep. He ever went as far as to lift her hand and let it drop. Now he was sure she was knocked out. He quickly got up on top of the bed and proceeded to pull her nightgown up and her panties down. He was shivering in ecstasy as he contemplated her two ass cheeks. They were perfect and firm. He started caressing them softly and kissing on them his dream had come through. The sweet aroma was driving him crazy as he started to mount her. He went slowly still a little scared that he would wake her. He placed his dick between her ass cheeks and started to grind gently. It felt so good he could not believe it. He stopped for a second to position his cock between her crack of her ass and down between her legs. In this position he could feel her moist pussy lips rubbing on the top of his cock. He arched himself on top of her and while kissing her neck he started pumping his hips. Oh it felt so good.

He started slowly but the tightness of her legs and moisture of her pussy was driving him crazy. Plus the feeling of her ass cheeks bouncing against his crotch area was just too much. He had to stop now and then to keep from cuming. Every now and then he would lift himself up just to see how his dick would get lost between those two mounds of firm meat. He kept spiting saliva in his hand and rubbing it all over his dick to keep it wet, as he would introduce it back between her ass crack. 

It felt so good that he speeded up his thrusts as he lay on her back humping away. It wasn't going to be long before he came. In one of those movements he clearly felt the head of his cock as it parted her pussy lips. He stopped to think about it but the lust and how great he was feeling did not let him think straight. He sat up and with one hand he parted her ass cheeks open and with the other hand he positioned his cock at the entrance to her pussy. As he started to penetrate her he could hear her let out a low sigh as his cock entered her cunt. As soon as he was all in he himself let out a loud Ahhh! 

It felt divine how her warm snatch would tightly grip his thick veined shaft. It was a good thing he was only 6 inches long any longer and he guessed would have waked her. As he lay there impaled in her hot wet pussy he checked her respiration to see if it changed. It didn't she continued to sleep soundly.

Man did it feel good to him he started to thrust in and out slowly but that didn't last long as he started to drill into her. Just watching her ass cheeks smack against him it was getting to be too much. Her body unconsciously responded to the pounding. Her ass checks clenched every time he would pull out and her vagina tightened as if she was cuming too. He was at the brink of cuming and he didn't care. He was in a high a high of pure pleasure and he just closed his eyes and pounded away. He did not realize that his mother was starting to wake up. 

She was groggy but getting her bearings quickly with all the jerking around. She turned her head and looked back in horror at her son as he buried himself balls deep into her. He was shooting his load all the way up in her and she screamed.

"Jake, what the hell are you doing?" 

As she screamed she clenched her ass cheeks tight not making the situation any better but just making him cum harder. He had one hand on her ass and the other keeping him up as both of them looked at each other in horror. Neither could believe what had happen.

THE END