t was the hottest day on record for mid-May when Greg came crashing through the door into his house. He had just finished a tennis match that ran later than it should have by about an hour and was dripping with sweat. He could hear his mother saying something to him as he came in, but couldn't make it out.
"I'm home! Going to take a quick shower" he called out as he raced up the steps. He couldn't wait to rinse off, but also needed a release. He had spent the first half of his school day conjuring up fantasies of how Ms. Edmonds would hold him after class to ask his opinion on what was an acceptable amount of cleavage in school.
He spent the second half of the day staring at Danielle Ryder's butt, of which little was left to the imagination through the combination her taut leggings and her gymnast body. Just the slight recap in his mind was enough to stir his penis again as he made his way from his room to the shower.
He stripped off his wet shorts, his cock bouncing out from underneath the corded waist, and slid the opaque glass door to the shower open, and was greeted by perfectly warm water. He got an initial soak, and then quickly his hand made it down to his throbbing cock where he started pumping, now thinking about Ms. Edmonds heavy tits again. His wet buttocks felt the cold damp tile as he leant against the wall and pumped harder and harder.
Greg was on the verge of ecstacy when he could hear a familiar creak. The bathroom door-
"I'll just be a second! I'm sorry, I know, I know, but I have to tinkle so bad" his mother called out predicting the angry protests of her son in the shower.
Greg quickly tried to conceal his erection. He was just about to finish though, and his cock was hard, red, and dripping pre-cum. He wasn't sure how much he could do to hide the current situation. He was both angry and mortified. Through the fogged slightly clear glass door he could see his mother rush by. She had a habit of wearing her underwear around the house, and this time was in her leggings and nude bra.
Cassandra was forty-four years old, but she never lost her baby face. She still looked 24 years from the neck up, and pretty much everywhere else to boot. She had a slight tummy, but it rarely ever went noticed positioned under her large 34 DDD breasts which were typically the focus of much attention, especially around Greg's friends.
She was now sitting on the toilet and Greg got a front row view of these massive melons pressed together as she quickly tried to do her business before more protests erupted from the shower. Greg's cock which had only just begun to fall came alive again at the sight.
His mom's bright red hair fell just below her shoulders onto the pale white skin of her chest which was laden with freckles and sunspots.
"Mom.. can you please hurry up and get out?" Greg asked flatly from the refuge of the shower.
"What do you think I'm doing, GREG? I'm going as fast as I possibly can. What am I keep you from? Important meeting going on in there?" she snickered.
"You shouldn't be in here at all" he growled growing frustrated! "I'm too old for you to be in here while I shower". He prayed internally that she had no idea he was masturbating when she walked in.
"I know Greg, and when the other bathroom is finally fixed I won't be, but until then it's going to happen from time to time. Don't worry I never look." she teased again. This was true. She was a bit more carefree than her son, but she respected his privacy, and hadn't seen him indecent since he was a young man. She had always been curious how he had made out...physically in his older age, but respected his privacy none the less.
As Cassandra wrapped up and cleaned herself, in her crouching over her eyes drifted to the opaque shower, and a spot in which the fog had cleared. In that slight instant she could make out the outline of Greg's slightly flacid, but still engorged penis. Her eyes went wide. She quickly averted them before Greg could possibly notice but the image was engrained.
Greg having reached his breaking point slid the glass door open about six inches and mockingly whispered "in your own time". As she stood up and pulled her leggings back to appropriate height her giant orbs flopped, and this sight sent Greg all the way to high-noon. All the blood immediately returned and before he knew it his cock was exiting the shower in full view of his mother.
Cassandra couldn't ignore it this time. As her son stood there the full length of his cock also rose and now extended out of the shower. She was shocked. It had to be at least 7 inches long and was girthy. It's not that she didn't think Greg would have a big penis, but on his hundred and fifty pound five foot ten frame it seemed giant. The veins bulged running up the thick shaft to a large shiny head. Good for him she thought briefly. "I hope that's not for me" she jested hoping to lighten the mood.
It didn't help Greg. He realized what had happened as the air temperature changed around his penis and instantly some of the blood went back from his penis to his face as he blushed crimson. "HA-HA! Very funny" he called out as his mother left the room all smiles. He couldn't finish now. She had ruined his moment of solace.
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Cassandra returned to her room both amused, upset with herself, and in awe. As she got ready to put a top on she caught her reflection in the standing mirror positioned in the corner of the bedroom. She ran her hands down her chest and over her large breasts as the cups of the bra fell down and her large pink nipples became exposed. She could feel herself getting progressively more and more wet, and finally gave into her primal urges realizing she would need to take care of herself before leaving the room.
Why now, though? What set it off? Could it really be the sight of her own son's cock doing this to her? It was just so perfect. She grew angry with herself at even the thought. Her hand reached to her night stand drawer where she kept her favorite toy. It clipped on to her fingers and began magically vibrating and pulsing.
She stripped off what remained of her bra and her enormous tits were free. She began to wiggle out of her leggings to give her access to herself and proceeded to massage what was now her soaking wet pussy while one hand was used to massage her breast. She kept trying to conjure up her usual imagery, but Greg and his stiff hard cock flashed to the forefront of her mind no matter how hard she tried...
She entered the bathroom so many times like she had prior. She heard the shower going for the last five minutes so she knew Greg must be in there. She'd pop in and out in a flash. When the door swung open, though, Greg was standing near the sink looking in the mirror as he pumped his glistening hard cock. She smiled at him as he turned to face her. "I keep trying mommy, but it's just not working"
"Let me try" she whispers back and for the first time feels her son's meaty cock in her hand-
"No!" she literally exclaimed out loud and shut off her toy. That's a sick thought, and we're not going down that road Cassandra. Cassandra finished her mental reprimand, and raised herself out of bed to continue to dress.
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It was now evening time and Cassandra stood over the stove slowly mixing together pasta and tomato sauce. She called out to Greg "Dinner will be ready in five". The response was delayed, but she received a verbal acknowledgement from Greg, and six minutes later he was rushing down the steps.
He came around the corner from the living room into the kitchen at break-neck speed. "Hey mom, I don't mean to eat and run, but some of the guys wanted to play ball tonight, so do you mind if I run down to the courts when I'm done?"
He sat in front of a plate laid out for him and began stuffing his face with garlic bread while the other unconsciously shoveled spoonful's of noodles towards his mouth. "You just got cleaned Greg. You're going to go get dirty and have to shower again?" his mother questioned.
These were the moments she would have loved to have a partner there supporting her and playing the bad guy, but no. Ever since Greg's father passed five years ago she had to play father, mother, friend, bad guy, and good guy; though it rarely felt like she got to play the good guy any more. She could see the frustration growing in Greg already.
"Fine. I guess it's fair since I did interrupt your shower earlier. You can get a proper and PRIVATE cleaning tonight" and she chuckled at the last part. "I just thought maybe we could hang out in the air conditioning tonight and watch a flick like we used to."
"How about tomorrow night, mom? I'm sorry but a full group is going to be up there and we rarely get to play five on five. I just don't want to miss out" he said truthfully.
"It's okay Greggy, but I'm still watching a movie, so if you get home early enough and want to partake just grab a seat. And don't be any later than nine tonight, please?"
"You got it" he replied and winked as he returned to the food on his plate.
Cassandra grew a bit sheepish now, but thought it was best to get most things out in the open "Do you want to talk about earlier?" she asked. Greg was dreading the shower incident coming up in conversation and his face grew white. Cassandra sensed this and quickly added "you have nothing to be ashamed of. Masturbation is completely normal and necessary. Your dad did it, I do it, everyone does it. I'm sorry that I interrupted that time and caused you any embarrassment." The words were right, but she wasn't sure it helped.
"Mom... it's fine can we just forget about it for now?" and Cassandra nodded her head in agreement.
"Just keep in mind who pays the water bill. Some of these activities can be done in the privacy of your room" she zinged him. Quickly, Greg stood up collected his used dishware and dispensed it in the sync while adding over his shoulder "noted. Alright I'm gonna get changed and head to the courts".
By the time he returned to the living room in his basketball shorts and tank top Cassandra had already changed in her blue silk robe, poured a glass of wine, and was making camp in front of the television on their sectional sofa. "I'll see you later, mom" Greg said opening and shutting the door behind him just as quick.
"Your loss" Cassandra muttered as she finished her first glass of wine.
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It was ten past nine when Greg reached the front door and he placed his hand on the front handle, hoping that his mother wouldn't give him any grief for being a tad late. As the door opened slowly he could hear the sounds of the television from the living room, but no greeting from Cassandra. He rounded the corner, and as he did his eyes became fixed to the TV. He wasn't sure what movie she had decided on, but currently on the screen a man and woman were having what appeared to be a passionate sex scene.
Greg got caught up in the display on the TV for a moment. He watched as the actresses breasts swayed up and down with each movement, and instantly knew he had inspiration for his second shower of the day. His eyes drifted to his mother who was positioned in the corner of the sectional. An empty bottle and glass of wine sat on the end table. Meanwhile, his mother was now passed out with her robe giving up trying to contain her massive breasts. Her whole left breast was exposed having fallen out of the bra and robe. Greg could see his mothers erect long nipple from where he stood.
His cock jumped to life nearly hitting him in his belly button. It felt like it was trying to break free of his basketball shorts altogether. He quickly made his way up the stairs to the bathroom. Typically he would have visited his room first, but he had more urgent matters to attend to. He couldn't even wait for the solace of the warm shower this time. He needed a release.
As Greg's foot planted on the top step Cassandra began to stir downstairs. As she did so she heard the familiar sound of the shower being turned on and knew Greg must be back. She felt cold and quickly realized that she had fallen out of her bra. She shoved herself back inside, now as covered as she possibly could be in the outfit, and was hit with an all too familiar sensation. Too much wine had led to her needing to urgently access the bathroom.
She quickly tip toed up the steps and made her way to the bathroom. The water had been on several minutes so she knew Greg must be inside. He'd be upset this was happening for the second time today, but he would have to deal with it. She knocked softly and opened the door barely waiting a moment for the knock to register.
Greg was standing at the back of the bathroom stroking his rigid cock. His filled balls swayed back and forth with each pump. His eyes were closed and Cassandra could make out as he whispered to himself "fuck yeah mom. Your tits are so big. I wanna cum on them so bad". Cassandra immediately went crimson, and the sensation to pee somehow passed. What did she do in this moment. If she tried to leave surely it would alert him and grab his attention, but if she stayed any longer he'd also notice and probably be mortified.
She stood there for a moment watching her son go to town on himself, and to her it appeared his exploits were being fueled with imagery of her. She didn't want to, but grew more aroused by every passing millisecond. Maybe this was the wine talking. She wasn't sure, but in the moment right now didn't care. She had needs to, and watching this young hard cock be pumped away to the thought of her was fueling her own desires. How best to handle the situation though..
"Greg" she muttered, and instantly Greg recoiled at the end of the bathroom attempting to cover himself from his mothers view which was entirely impossible at this point. He was about to yell when he interrupted him. "I'm sorry I needed to pee and it was an emergency. I apologize this is happening a second time today. Hop in the shower get cleaned off and then come and see me, so we can talk about this" she said seriously as she left the room.
Greg was beyond mortified. Had she heard him? How loud had he been muttering about his mom while he jerked off? As she left the room he disappointedly dragged himself and his limp cock into the shower where he soaked and lathered for as long as he could not wanting to have to go confront his mother after this.
When he could delay no longer he hopped out through the sliding glass door and began to dry himself. He went to his room where he found a fresh pair of mesh shorts and a sports tee. He put them on much like an inmate on death-row might don the final prison uniform before his execution. It felt like he was walking the green-mile as he made his way to his mother's bedroom door. He knocked softly.
"Come in" he heard in response through the door, and with that he slowly began to open it. As the door opened he could see his mother standing at the end of her bed still in her robe, which was now more secured. "I really am sorry that I caught you like that, Greg".
"Why can't I have any privacy at all" he exclaimed! Growing angrier and possibly trying to go on the offensive because of his embarrassment.
"I know, I know. It's not fair" Cassandra quickly responded. She knew it wasn't. He was a growing boy and his hormones were probably all over the place driving him nuts. The last thing a growing boy would want just happened to him and it was her job to fix it now she thought to herself. "I saw you in a compromising position, and I figure the only way we can make it even is for you to see me in the same way" and with that she untied her robe and it fell gently to the ground almost like a parachute.
Greg was about to yell again when before he could his mother's robe fell to the floor. She had removed her underwear so that underneath the robe she was completely bare. She stood in front of him naked. His eyes left her eye contact and started taking in the entire sight. Her read hair rested gently on her chest where her huge breasts were now both completely exposed. Her areolas had slight bumps on them and her nipples were long and erect almost pointing at him. They must hang a little lower than when they did when Cassandra was younger, but the perfect shape was still there. His gaze continued and reached the slight tummy she had, but then met with a perfect landing strip of tightly cropped red hair. It guided a path directly to her womanhood.
The silence was deafening and you could hear a pin drop from any room in the house at the moment. Greg felt an all too familiar feeling as as a tent formed in his clean mesh shorts. It was so rapid that the head of his cock actually felt as though it was protruding from the left leg.
Cassandra couldn't believe what she was doing herself. She could almost see herself from outside of her own body. Her eyes sensed movement and drifted to the source. Her eyes locked on the bottom of her son's shorts where his cock was now trying, and succeeding, at escaping. The pulsing head of his cock stuck out of the bottom of the left leg of his shorts. There was a long pause.
Finally Greg broke the silence "Mom, I appreciate what you are trying to do, but now I'm just in the same situation. I'm not sure how this helps!"
"I know you feel embarrassed Greg, but you shouldn't. I carried you, took care of you, I've seen you in nearly every way a person can see another person. Maybe if we get rid of the mystery there will be nothing to be embarrassed about anymore. Why don't you take those off so we can deal with it and be done. Move on."
"You want me to get naked!?" Greg was shocked at the thought.
"Five minutes ago I saw you in all your glory" the thought made her tingle. "I don't see the big deal."
"I think this is kind of crazy, but you're right I guess. The damage is done" and with that he pulled his shorts down. His cock jumped out now completely erect at the sight of his mother and her huge melons swaying with every slight movement she made.
Cassandra knew her body shouldn't be having the reaction it was having, but her wetness between her legs grew. She joked "I guess it was for me, huh"?
Greg's frustration reached it's boiling point. He started pacing in circles but closer to his mother. "I can't help it! I'm always horny and then you walk in wearing basically nothing, and yeah so things happen.."
Cassandra could see how upset Greg was. She moved closer and put her hand on his shoulder. "It's okay honey. There's honestly nothing to be upset about. I take it as a compliment that your old run down mother can even give a guy as young as you erections still" she joked. When she stepped in Greg's large cock head brushed against her tummy. She could feel it's warmth on her skin and she shuddered.
Greg began to calm "You're not run-down at all mom. Stop. Your body is perfect and that's part of the problem." He was also aware that his cock had now touched his mothers bare skin. The sensation of his tip dragging on her bare abdomen was almost enough to make him finish right then and there. "You have the body of a twenty year old, and your tits are so big and perfect" as he said this he immediately felt self-conscious, but his cock twitched again. Now the under part of the shaft rested on her abdomen with his tip pointing towards her breasts he had just mentioned.
Cassandra began to blush while simultaneously the area between her legs grew more and more slick. "You don't mean that honey your just trying to be nice" she said smiling back at her son."No it's true unfortunately. All my friends have noticed. They spent the entire last summer coming to our pool hoping to catch a glimpse of you in a bikini" he laughed.
"And you? Were you hoping to catch a glimpse?" she was now teasing her son. His cock was still firmly squished against her abdomen as she lightly massaged his shoulder and consoled him.
"I don't need to catch a glimpse. I see you around here in less than that every day I feel like." It was true. He did see her in a lot less on a daily basis, but it didn't mean that this past summer he was any less interested in seeing her bounce around in a tiny bikini if he was being honest with himself.
Cassandra had never really considered what a burden that could be on a growing young man. She wanted to ask a question, but knew she better not. It couldn't do any good in the moment they were currently in, but she was no longer thinking entirely with her head either at this point in time. "What... What were you thinking about when I walked into the bathroom just now?"
"Mom.. I don't want to talk about that" he stated exasperated by the question. How could he tell her that she saw her bare breasted on the couch and was so overcome that he had to run upstairs to furiously masturbate?
"Was it me" she inquired shocked? She shouldn't even be asking the question, but deep down Cassandra kind of knew that she wanted Greg to confirm it. Her hand fell from his shoulder and as it did the palm grazed the head of Greg's throbbing penis. He shuddered as the sensation of her soft hand on his cock head even briefly.
"Look, I came inside and you were passed out, and with the way you were sitting..." he paused "I could see your breasts" he finished and looked down again at the massive pair which were centimeters from touching him at this point. He somehow grew even harder, and his cock shifted further up her abdomen.
Cassandra was so wet at this point that if she were to walk she thought you'd hear her legs squeak. She caught herself for a moment "I'm sorry honey. I know this is tough on you, but I think this is the best thing we could have done given the situation. It's all out there.." she gestured down at his rock-hard member "... and clearly you have nothing to be embarrassed about" she smirked as she said this.
Her brief smile was electric. It was becoming too much for Greg to take. "I uh-I should go now" he could see pre-cum leaking from the tip of his cock onto his mothers tummy where it was nestled right below her massive tits. The imagery was out of a dream, and he could explode at any moment.
"If that's what needs tending to.." she gestured down again "you might as well take care of it here. It'll save you the trouble of having me walk in on you again at least" she mused. In this moment her head was losing the battle. She wanted to see him working it again. She wanted to see him finish, and now that she knew he was the inspiration she felt almost entitled.
"In front of you?" he asked incredulously.
"Yes, I don't see the big deal. It's out on the table. I knew long before now that you did that. I feel bad that I've kept you uncomfortable all day long. Let's just expedite this process while we're in the state we're in" her arm motion gestured to the fact that she was completely naked and he was half-so. "Lie down on the bed. There's some lotion on the table beside the bed that should work. But please take your shirt off so you're not walking around like Donald Duck." This made him laugh a bit. He took his shirt off revealing a firm lean muscular chest and arms to pair with it.
She put her hand on his back and guided him to the bed where he gingerly sat and reached for the lotion on the end table she had pointed out. She sat on the other side of the bed and waited.
"You're going to be here the whole time?" Greg asked.
"Honestly I thought it might help given the new information." and as she said this she giggled and squeezed her massive tits together. Her long erect nipples nearly crisscrossing in the air. Greg gave in and squeezed the bottle over his tip and let a generous amount of the fluid run over him before he slowly and unenthusiastically resumed his activities from the bathroom.
He pumped a few times, but defeatedly let out "I don't think I can mom. It's just too weird." He wanted nothing more than this release, but this was all too much for his mind. He couldn't focus on any one thing.
Cassandra grew bold, both because she wanted to, but also because she could tell her son was in pain and whether on purpose or not she was the root of the cause. Her hand cleared the space between her and her son and her soft hand wrapped around his hard pulsing cock. "Let me help" she implored. She slid the rest of her body over beside her son so that they were positioned next to each other. She took long slow strokes on his cock. Her eyes locked in on it for the first time with a different sort of intent.
"Oh my god, mom" came out of Greg with sharpened shortened breath. He couldn't believe what was happening.
"Does that feel good baby?" Cassandra whispered. She realized that she had crossed the line from motherly to something else in this moment, but went with it. Her son needed something else right now. He continued to expand in her hand reaching a full size she hadn't seen before when he was masturbating by himself.
Greg was starting to let loose himself. He couldn't help it. This was greatest feeling he had ever experienced. "It feels so good" he barely got out. Cassandras pace picked up as she began to stroke faster and faster with greater intent. Greg's eyes locked onto his mother's giant tits that bounced with each stroke. Her eyes met his.
"You can touch them you know" she said and added "if you think it will help". Who was she kidding? She wanted him to fondle her breasts. She wanted him to touch her all over right now. She could feel the sheets underneath her grow more and more saturated.
Greg immediately placed his palm on her right breast. He was gentle and apprehensive, but Cassandra used her other hand to guide his and make his touching a tad more forceful. Greg reactively started kneading her giant breast in his hand. He massaged it and allowed the hard nipple to get between his fingers and gently tugged.
"Mmmmm" Cassandra instinctively moaned. It had been a while since she had been touched, and even longer that she had gone without the raw passion that Greg was exhibiting for her in this moment. Confident that her son knew what he was doing now, her other hand drifted to meet her other on Greg's engorged cock. At full mass it was certainly large enough to justify two hands. Each worked its way up and down his slick cock twisting and turning as her hands met the tip. Greg moaned louder and louder. "You like when mommy uses two hands to stroke your big cock baby?" she almost couldn't believe herself as the words left her mouth, but it didn't deter her. She grew more and more into it. She began to bite her lip as she watched her hands mechanically move in perfect synchronization up and down the length of her son's meaty unit.
Greg had grown bolder himself and leaned over and took his mother's nipple in his mouth sucking on it furiously. "Oh yeah, mom" he responded back. He had never been this hard in his life.
Cassandra continued to stroke moving her head as close as she could to her son's cock while he sucked on her tit. She lightly breather on the head as her hands worked their way up nearly meeting her lips.
"Oh my god" Greg let out. "I'm going to cum, mom." His body began to twist and contort with pleasure.
Cassandra let out a devious smile "Good baby. Cum for mommy. Mommy wants you to cum so hard and good." She looked back at him in the eyes yearning for his finish. "Where do you want to finish baby? You want to cum on mom's big tits?" he gestured with one of her hands to the massive orbs jiggling back and forth.
"Oh my god, yes mom. Please. I've been thinking about it for so long" he let out. He was for a millisecond embarrassed by this admittance, but he had no control at this point. "It's happening" he cried!
Cassandra could feel the strain in his cock growing and the familiar feeling of an impending finale. She positioned herself so that her breasts lied on her sons thighs. The nipples perpendicular to the tip of his cock. Her stroke slowed, but her grip became more firm. She could almost feel the cum drifting up his long shaft. She took a few more purposeful strokes before his body spasmed and from the tip of his cock he shots an initial rope of cum all over her left nipple. She continued to stroke as Greg cried out, and more and more cum came shooting out covering the majority of her breasts. She maneuvered his cock rubbing it all over her breasts and in between. The cherry on top of the ten seconds she spent massaging his cock head on her erect nipples, and that elicited yet more cum from the young man. She had never seen an explosion like this with all her partners over the years. "Oh my god. You came so much baby. That's impressive" she said patting his chest.
Greg laid there in disbelief. What had just happened? What had he just done? What had she just done? And how would this change their relationship moving forward. He was about to say something if he could find any words at all, but before he could his mom pressed a finger to her lip.
"Shhhhh. Neither one of us is fit for this conversation right now. Why don't you go get some rest and we can talk about it in the morning." Greg nodded in agreement. He quickly collected his clothes and made his way to the door. He took one last glance back at his mother. She was sprawled out on her own bed, her big breasts currently adorned with his ejaculant. He'd probably have to masturbate again. With that, he closed the door and returned to his room.