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Jill would always remember the first time she saw her son masturbating.

It happened months ago. Tim had just turned 19. She wanted to surprise him on the midnight of his birthday with a gift while he was still watching tv in the living room.

Jill gently and quietly opened her bedroom door with her present in hand, and softly walked towards the living room without making a sound- and what she saw left her stunned: Her son was watching softcore porn on cable. As she quietly stepped closer to the couch, she could see that he was masturbating.

Her heart pounded. She couldn't believe that her wholesome young man could do something so brazen in their living room. Sure, she knew that all boys were especially horny at that age, but this? In the same house while he thought his mother was sleeping?

But above anything else, she couldn't believe how she felt about seeing him pleasure himself so explicitly. Jill had only been with one man her entire life, and that was her ex-husband. Her favorite fantasy was to watch him masturbate while looking at her, but her ex-husband always laughed it off and was reluctant to do it because of how ridiculous he thought it was.

Now there she was, the middle of her legs becoming wet, watching her son pleasure himself. She was aroused and she knew it. She quietly tiptoed back to her room before she could get caught, and she later did something she NEVER thought she would EVER do- she fantasized about her son for the very first time in her life.

Please.. Let me watch…

"This looks good," Tim said as he went to the kitchen for breakfast.

She smiled, "Thanks. I was supposed to meet some clients this morning, but I got a message last night that they had to cancel. My boss said I could finish my report at home, so I figured I might as well do some cooking and catch up on chores while I had the extra time."

"Lucky," he replied while eating. "I've got an exam today and it's a real pain in the ass. But seriously mom, you work too hard and you should try relaxing a little."

"If I relaxed during my free time, then who would cook and clean for my college boy? It certainly wouldn't be you," she replied jokingly.

"Good point. In that case, just work the amount that you need and don't tire yourself out too much."

She playfully slapped him on the arm. "Very funny. You know, if I didn't love you so much, I'd force you to do your own laundry and to clean your own room."

He grabbed the rest of his food and got up to give her a kiss. "Then I guess I'm really lucky to have such an awesome mother. I wish I could stay and eat, but I have to meet some friends for some last minute studying. It's the only way I can be as smart as you, right?"

"I'm glad we agree on that," she replied as he smiled and left.

***

After cleaning the dishes and vacuuming the carpet, Jill went to her son's room to do his laundry. She pulled off the pillow case on his bed, and when she grabbed the blanket, she saw something that left her as speechless as the day she caught her son masturbating months ago: There was a photo of her underneath his blanket.

'What's this doing here?' she thought to herself.

It was a photo of her in a one-piece bathing suit from a summer vacation they had two years ago. The picture itself was from a photo album which she kept in the closet in the hallway. But what was it doing in his bed?

A realization had suddenly come over her. When she vacuumed his room a moment earlier, she had picked a few pieces of used tissue paper off the floor and threw it in his trash.

'Oh god,' she gasped. 'Was my own son thinking about me?'

Jill felt torn. On the one hand, she felt disgusted and betrayed that her own son could do such a thing with her picture. But on the other hand, she couldn't be mad at him because just a few months ago, she had watched him masturbate and then she fantasized about him afterwards. The thought of her son masturbating to her picture made her feel inexplicably naughty, but in a good way. She even felt a little flattered by it.

Almost without thinking, Jill walked to her room to grab an even more private photo of herself which she had hid in a drawer. It was a picture of one of the rare moments in her life that she had ever worn a small bikini while at a private pool party with her close friends.

She went back to her son's room and tucked it neatly under his blanket for him to 'use' later.

***

The rest of the day was as usual. She did her work, cooked, had dinner with son, and watched a little tv before calling it a night. Also as usual, Jill ended her day by washing up and putting on her flannel pajamas before heading to bed. But when she exited her bathroom, she saw her son walking down the hallway and towards her bedroom. And by the look on his face, he had something important to say.

"Mom...Were you...did you clean my room today?" he asked uncomfortably, standing in her room.

"Of course I did," she replied casually, as if nothing was out of the ordinary. "Your room didn't just clean itself, you know."

"Well I know that. But my bed...did you..."

"If you're referring to the picture left under your blanket, then don't worry, it wasn't a ghost that put it there- I did," she said with a soft smile.

"Am I missing something?" he asked. "I mean, shouldn't you be mad at me? Aren't you upset at all?"

"I'll answer your question on one condition," she replied.

"What's that?"

"I want you to tell me why you were using my picture. And I want an honest answer."

"Is this really necessary?"

She nodded. "It's necessary if you want me to answer your question. Don't worry, I'm not judging you for this. Answer truthfully."

"I don't know. There's nothing else to use around here."

"Wrong answer. We have cable tv and the internet. Now tell me why you were using my picture."

He paused for a moment. "Fine. Being completely honest here, I've always thought of you as being my ideal woman. You're smart, classy, caring, and you're really, really sexy. I know you're my mom and everything, but that's just how I feel."

"That's very sweet of you to say," she replied, feeling genuinely touched by his words.

"Now it's your turn. Why did you leave your bikini picture in my room?"

She sighed, "Since you were so open and honest, here it goes; I've always been excited by the thought of a man pleasuring himself. Don't ask me why, but it just gets me going. It's the only kink I have. Your father rarely ever let me watch him masturbate, and on the rare occasions he did, it would only be for a quick few seconds and he would laugh it off before stopping. Then a few months ago, I saw you... you know..."

"You caught me jerking off?

She nodded, "In the living room late at night. I saw you masturbating, and truthfully, a big part of me was very aroused. And when I saw my picture in your bed today, I was flattered by it. In fact, it turned me on in a strangely erotic way."

"All I can say is--- wow! You always were a cool mom, but when it came to the magic s-word, I've always thought you were a real prude because of how conservative you always act," he said, referring to sex.

She smiled, "It's getting late and I have to wake up early Tomorrow for work. We better get to sleep."

"I guess so. But, um, do you think we can finish this conversation another time? It's a pretty important topic if you ask me."

"Sure. But only if I get to ask you one last personal question?"

"Anything," he replied.

"Do you plan on using my picture before you go to bed?" she asked as if it were nothing out of the ordinary. "Do you plan on masturbating with it?"

"Jeez, mom, you've really put me on the spot here..."

"I'll take that as a yes," she smiled. "So would you rather see the real thing, or do you prefer the picture?"

"Are you asking what I think you're asking?" he asked in a state of disbelief.

Jill nodded to her son. "I am. But only if you promise not to tell anyone. I don't even want to think about what people would say about me as a parent. I'd be the talk of the town, and not in a flattering way."

"Mom, you know that there's no way I'll ever be stupid enough to ruin what I think you're offering me right now. And you know I would never hurt you like that."

She grinned, "Good. Now you can start by pulling down your shorts and having a seat on my bed."

"Me?" he asked with a confused look on his face. "But I thought... I thought you were the one who was going to show..."

"I am. I want to watch you masturbate in front of me. And in exchange, I'll show you my breasts. That's our deal. We both get what we want out of this. Sound fair?"

His hands slowly made its way around the waistband of his shorts and he gave it a gentle tug downwards.

"It does sound fair," he said. "God, this is going to be embarrassing. But it's worth it to finally see those breasts of yours."

With one swift motion, Tim bent down to pull his shorts and underwear off, leaving him naked from the waist down.

"Oh my, you've grown," she told him, with a sense of approval over his manhood.

He smiled at his mother. "Thanks. Now where do you want me to do it?"

"On my bed with your back against the wall. I'm sure that would be comfortable for you."

He did as he was asked, sitting on her bed pressing his back against the wall.

Jill's eyes lit up as she saw her son growing and becoming erect. "Looks like you don't need me to show you any skin. You're aroused enough just being an exhibitionist to your mother."

"I'll admit that it's really hot being naked in front of you. And it's even hotter knowing that you enjoy it. But of course, I do need to see something. A deal is a deal, remember?"

Her hands casually started unbuttoning the top of her pajamas. "You're right. A deal is a deal."

Just when enough buttons were undone, she spread open the material covering her chest, and she exposed herself to her son.

Her heart was pounding as she watched her son's eyes grow along with his cock. Her breasts were completely exposed for him. It was sinfully arousing for her to see her own son slowly start to masturbate in front of her, while his eyes were locked onto her bare medium sized breasts, with her pink nipples becoming stiff.

"You seem like you're enjoying yourself," she asked, breaking the slight awkwardness in the room.

"I am," he said while masturbating. "This is so hot. You have such an amazing body mom."

"Thank you. I'm enjoying this as well. Do you need any extra stimulation?"

She didn't wait for her son to answer before she started softly cupping the round botTims her breasts and played with her hard pink nipples using her fingers. She found herself inadvertently becoming even more aroused, as her breasts and nipples have always been very sensitive, and it was clear to her that her son was enjoying the show as his breathing and stroking became harder.

"Oh god. Keep playing with those tits mom. I can't believe this is happening," he groaned.

Watching a guy masturbate up close was one thing, but seeing her own son do it while looking at her bare breasts drove her absolutely wild. Her secret masturbation fantasy had finally come true, along with the added taboo of i****t to make things ever hotter for the demure woman. She held in her emotions and excitement as she continued to fondle herself for him.

It wasn't long before he exhibited all of the tell tale signs of having an orgasm; a sight she hadn't seen from a man since she became a single woman.

"Cum for me," she said innocently. "I want to see you cum."

His hands stroked faster and his moans became louder. His back suddenly arched, his muscles stiffened, and a flurry of his sperm shot up in the air and all over his stomach. He didn't stop stroking until he was completely drained, with his eyes never leaving his mother's body. Then when it was over, he collapsed and went completely limp.

She smiled, "That was an impressive amount of fluids you released. Looks like you've inherited more than just your father's good looks and charm."

Tim didn't reply, he just laid there, recovering, while Jill closed her top and reached over to grab a few pieces of tissue paper from her bedside table to toss on her son's stomach.

"Thanks," he replied, using the tissue to clean himself. "I haven't felt anything like that in a really long time. I mean... actually doing that in front of you and seeing you touch yourself was almost better than hooking-up with any of my classmates. It just... you know..."

"I know exactly what you mean Tim. The taboo of mother/son i****t can be quite thrilling to some people, and it looks like we fall under that category. Just don't ask for it again. Not anytime soon. This might be a one-time thing okay? I don't want things to get out of hand between us-- no pun intended."

"I guess so," he complained. "But I'm glad I got to experience this."

With that said, the two of them said their 'good nights' and each headed to bed.

***

The next morning. Jill sat at the breakfast table looking like her prim and proper self. Her hair and make-up were perfectly done, and she had on one of her more expensive pant suits in anticipation for an important meeting in just over an hour.

"Good morning sweetheart," she said with a loving smile as her son came down.

Tim smiled back and gave his mother a kiss on the forehead before sitting down to eat.

"Morning mom! I must say, you look extra wonderful this morning. And thank you for making me this wonderful breakfast for me. Did I ever tell you that you're my favorite person in the world?"

"Well aren't you cheerful today," she skeptically noted. "I don't think you've ever thanked me for anything. Please don't tell me that you've been possessed."

"I'm in a great mood, especially after last night."

"Oh, of course. That. It was a pretty outrageous night, I'll admit. And we both certainly got what we wanted out of it, no matter how taboo it was."

"Does that mean you pleasured yourself afterwards?" he asked with a smile.

"I guess there's no point in denying it. Yes, I masturbated after you left, and it was great. I know it isn't something that a mother should ever do with her son, but it's our little secret, right?"

"You bet it is. And speaking of which, can we do it again really quick? I couldn't stop thinking about you all night, or all morning after I woke up. I could really use the relief before I go to class."

"Didn't I say to not ask me about it again?" she asked in a peeved tone. "Besides, you looked like you released a healthy amount of sperm last night, so I refuse to believe that you need any type of 'relief' so soon."

Tim gave his mother a serious look. "Mom, the amount that I shot last night is what I consider to be normal. I usually cum that much once or twice a day if I have to. After what we did last night, my body is practically on overdrive. I won't be able to concentrate at school today if I can't get off the way I need to."

"Well then just masturbate the way you normally do. It's not exactly rocket science."

"I know that, but you've really raised the bar after showing me your breasts. I've wanted to see that for a really long time. Simply using my imagination or looking at pictures just won't cut it for the time being."

She sighed and gave her son a playful smile. "You've made your case. I guess this is partly my fault for starting this whole thing. But make it quick since I have an important meeting to attend soon."

Jill stood up and placed her hands around the lining of her jacket, preparing to take it off. But just as she did that, she stopped.

"You know, it would take too much time for me to remove my entire top and put it back on afterwards. Plus I don't want to get any wrinkles on them. Do you mind if show you my lower region instead? Would that work for you?"

Tim's eyes lit up at his mother's counter-offer. "Hmm...That's not a bad idea. That would definitely work, sure."

Her hands moved down to the top button of her pants. She undid the button, pulled her zipper down, and let her pants fall to her ankles.

"Good," she said. "Then it should help you to finish faster. As I've said, I have an important business meeting this morning which I can't be late for."

Jill brought her fingers to the top of her panties and yanked them down, letting them fall to her ankles as well, exposing her cleanly shaven crotch along with her bare vagina.

"Like what you see?" she asked proudly.

"Oh god mom. I love it," he replied gushingly. "You look sexier than any of the college girls I've been seeing lately."

She smiled, "Thank you for the nice compliment. Now start stroking. I'm a busy woman and I haven't got all day here."

Tim got the message and swiftly pulled his shorts down to free his raging hard cock. He leaned back on his chair and started stroking himself for both his own pleasure, and his mother's. Jill then pressed her rear-end against the table and spread her pussy lips slightly apart for her son to get a better look. She loved teasing him and having that power over him. And it worked, his eyes were glued to her womanhood and wetness as he stroked himself even harder.

"That looks like fun" she said, licking her lips at her horny son.

"You bet it is," he replied, staring at his mother's open cunt. "Do you want to try it? You know, stroke it for me?"

"I can't. That would be crossing the line. Watching is one thing, but actually touching..."

He stopped his mother mid-sentence. "No one has to know, remember? Isn't that what you said to me? It'll be our little secret mom. Trust me."

Jill gave him a skeptical, yet excited look. It was a look which said, 'Why the heck not?'

"Okay," she replied softly. "You only live once, right?"

She reached down and took her son's throbbing penis in her hand. Her heart raced as she crossed 'that line' for the very first time. Tim's heart raced as well. It was the first time in her life that she had ever given a guy a handjob, and it was with her very own son at that. It was an i****tUOUS handjob.

"God that feels so good," he moaned. "Stroke it harder mom, faster."

She heeded her son's words and gave him exactly what he wanted; what he needed to feel in order to cum. She gripped him tighter and stroked him. She loved how his eyes went from being glued to her open vagina, to being closed shut because of the i****tuous pleasure he was receiving from her. And most of all, she loved having complete and utter sexual control over her own son.

"God... I'm going to cum... faster mom... harder..."

Jill did the cruel thing and instead slowed down.

"What are you doing mom?!" he panted. "I need to cum sooo bad."

She smiled and stroked him even slower. "I kind of like torturing you. It's fun watching you suffer."

"Please!" he begged. "I'll do the dishes for a week! I'll do your laundry! Just let me cum already!"

"That's not a bad deal. I accept."

Jill's hand went in full motion and she furiously jerked him off. She quickly found that Tim wasn't joking when he said that he really needed to cum, and that he often produces large amounts of sperm, as his orgasm shot wildly in the air and onto her hand and on his clothes.

"Oh god!!!" he yelled.

She didn't stop stroking until every last drop of his 19 year old cum was drained from his body. And she loved every second of it.

"Feel better now?" she asked rhetorically.

"God, I feel like a new man," he panted. "I feel like I'm swimming in the ocean."

She laughed and pulled her pants up. "Well, you're certainly swimming in something right now, but it's definitely not water."

"Oh...right..." he replied, looking down at his own mess. "Did you at least like doing it for me?"
"It's not a bad way to start my morning."

Before she left, Jill looked her son straight in the eyes and licked her fingers clean, eating his cum. She savored it and rolled it around in her mouth while Tim watched in delight as his sophisticated mother ate his cum.

"Yum... You taste good. Now if you'll excuse me, I have to wash up and head to the office. Have a great day," she said as she left the kitchen with a huge grin on her face.

***

Her fantasy had finally come true. Not only did she get to watch a guy masturbate twice while admiring her body, but she got to masturbate him with her own hand. On top of that, the fact that it was her son who she did it with only made things that much more taboo, but in a good way. It was all she thought about while at work.

After a busy day in the office, Jill came home and immediately kicked off her shoes and breathed a sigh of relief. But just when she thought she was ready for a long break, her overly eager son came to greet her at the door.

"Hey mom!" he smiled. "Have a good day at work?"

"Hmmm... greeting me at the door and asking how my day went? I guess I should start giving you handjobs more often, maybe then you'll start helping with the household chores regularly."

"I hope you're being serious because I really like that arrangement," he said, flashing another smile. "Maybe we can start now? I'm feeling a little pent up again."

Jill looked shocked. "Again? After all you came last night and this morning?"

"Like I said, that's normal for me. I could really use your hand for another round of relief."

Tim didn't wait for his mother's reply before pulling down his shorts and underwear to reveal his semi-erect cock in their living room, while the late-afternoon sun was still shining through the windows.

"Jeez! Tim! Put that thing away before someone outside sees you."

He shrugged off her worries. "What's the big deal? We could just close the curtains and no one would know."

"What have I created?" she jokingly asked. "I had no idea anyone could be so sexually active; your father definitely wasn't."

"You haven't created anything," he playfully replied. "I've always been a horny little bastard. But what you did yesterday was kind of like giving alcohol to someone genetically predispositioned to be an alcoholic. It's the same equivalence. You got me hooked. So this is technically your fault mom."

She sighed, "I guess I'm finding out the downside of paying for that expensive education of yours, aren't I? You're becoming too smart for your own good young man."

"The way I see it see, we both have the same mutual-masturbation fetish anyway. So what's the harm?"

Jill paused and gave her son a stern motherly look. "Well, I guess there's no point in arguing anymore. Plus, I suppose it's not a bad way to unwind after a stressful day at work either. Close the curtains and I'll take care of that hard-on for you."

Before those last words could escape her lips, Tim ran over to the windows with his penis flopping around and quickly closed the curtains.

"Well that was fast," Jill noted.

Tim pulled off his t-shirt to get completely naked and he sat down on the couch. "This is way better than getting presents on Christmas. So why wouldn't I be fast?"

"Your youthful enthusiasm never gets old," she replied with a loving smile. "You know, I didn't expect things to happen the way that it has, or for this to happen as often as it is, but I suppose there's no harm in enjoying it."

Jill then put one hand on her business jacket, pinching the bottom button, and another hand on top of the zipper to her pants.

"Breasts or vagina? It's you're choice, and you can only pick one," she said to him.

"Can't I see both of them at the same time?"

"Nope, don't forget that I'm still your mother, not your girlfriend or your plaything. There's got to be boundaries here."

"Your pussy then," he replied. "And since you're showing only one thing, do you think you could at least throw in a little bonus for me? You set a really high bar this morning."

"Fine. I'll use my hand."

"I was thinking a little more than that. Maybe you could let me... go inside?"

"Excuse me?" she replied in a stunned tone of voice. "I most certainly will not have sex with you, young man. In spite of everything we've done, I am still your..."

"I know, I know mom. It doesn't exactly have to be sex. Just think of it as you giving me a handjob like earlier today, but instead of using your hand, it'll be with your vagina instead. Think about it. A handjob with your vagina."

She gave her son a puzzled, yet playful look, as she attempted to decode what he had just said.

"A handjob with my vagina, eh? That's new. And I thought I've heard it all..."

"Anything to have sex... uh... I mean... anything to make my mother feel good. This is more for you than it is for me. I hope you know that," he said with as much charm as he could muster.

Jill smiled and raised her eyebrow, "Really? This is more for me. If that's the case, then I better have a mind-blowing orgasm when this is over. If I do, you might get a little reward after."

She undid the button and zipper of her expensive pants, and after she took them off, she neatly folded it and placed in on a nearby chair. She took a deep breath and did the same with her panties, leaving her completely bare from the waist down except for the pantyhose on her calves and feet. Before she walked over to her son, she posed and modeled for him, teasing him, making herself feel even more attractive and desired thanks to the look in his eyes.

"God, you're so fucking beautiful mom," he stated emphatically.

"Thanks darling," she said as she moved to hover over him. "I didn't want to tell you this earlier, but you're a lot bigger than your father is down there, and he's the only man I had ever slept with. So please be gentle with me..."

With that said, she placed both feet on opposite ends of the cushions on the couch, and slowly lowered herself to her son's massive hard-on. Her vagina was spread wide open and her son used his hands to make sure that his throbbing cock was pointed straight towards his mother's womanhood as it descended. Once her labia and pink insides touched the head of his cock, she paused for a moment, before continuing to lower herself, inch by inch, until the entire length of his cock was inside her vagina.

"Oh my... you're so big... It's been so long..." she moaned.

He reached around to grab her ass to pull her forward. "I can tell. You're so fucking tight and wet mom. I'm horny as hell right now."

Jill became wetter as she heard her own son strings those words together; 'tight, wet, and mom.' No matter how either of them tried to rationalize this, it finally struck her that they were actually having sex. He was inside her body stretching her vaginal walls. But she didn't care how bad it was, it felt good. It felt amazing. It felt right.

She slowly started rocking her hips while they looked each other straight in the eyes. With every gyrate she gave, she felt his raging hard cock go that much deeper inside of her body. As her dripping wet vagina began to loosen and relax, she began to thrust even harder. Their arms were wrapped tightly around each other and they felt each other's breath on one another's lips.

"Oh god mom... this feels so fucking good... I love this mom..."

"Just relax," she moaned. "Enjoy the moment. I want you to remember this for the rest of your life."

Their unholy mother/son coupling became even hotter and more intense. She remembered how it all started when she watched her son masturbate, now here she was, fucking him. Seeing him under her sexual control made her feel aroused in a way that she had never felt before, and it was taking its toll on both of them. Soon, she recognized the telltale signs she knew all too well from her ex-husband, his father, as well as a burning sensation between her own legs.

"Mom... I'm going to cum..."

"I know honey... I know... Just let it happen. There's nothing to be afraid of. I want your cum inside of me."

She watched his eyes roll back and felt his body arch. Soon, she felt a massive load of his cum fill deep inside of her vagina. Her own body gave a similar reaction to his, and she felt her muscles spasm, and her vagina having a strong burning sensation. It was the best orgasm she felt in years (if not the best orgasm she ever had). Fluids rushed down from deep inside her. Every inch of her body wanted her to scream out loud, but instead, she planted a big sloppy wet kiss on her son's mouth for the very first time. It was an i****tuous kiss that made every motherly kiss she had ever given him on the cheek or forehead absolutely pale in comparison.

"That was so amazing," she said in between kisses as they both calmed down. "I've never felt anything like that before in my life."

"I was about to say the same thing. I think I've already told you this before, but you're the coolest mom ever."

She gave him another kiss and got up, letting his flaccid penis just plop out of her body, leaving a trail of both of their orgasms dripping down her leg.

"Thanks. You're sweet. But I really need a hot shower right about now. Oh, and I almost forgot..."

She bent down and took his wet flaccid penis in her mouth and quickly sucked the fluids off. Her tongue quickly ran laps around the sensitive area of his head and around the length of the shaft.

"Oh fuck..." he panted as his mother finished using her mouth on his cock.

"There, now you don't have to go through the troubles of wiping anything off," she said with a wink.

"Next time we do something together, I want that! Your mouth feels as good as your pussy does."

She smiled, "Well, you'll have your chance sooner rather than later. Start packing some of your stuff and put them in my bedroom. With a cock like yours, you'll be sleeping in my bedroom from now on."

Tim watched as his classy mother turned away, still smiling, and picked up her pants and left. She was still naked from the waist down. His eyes were locked onto her rear-end as her luscious ass cheeks swayed from side to side as she headed up the stairs.