Dancing with Monique

You let out a big sigh as you stretched your back. You had been sitting behind your desk for hours today, revising for the upcoming exams. With just a few five-minute breaks, you managed to get through chapter after chapter. Your ability to concentrate had drastically improved in the past few months. You had still studied for a long time, so you decided that you could take the rest of the day off. As you stood up to go to the bathroom, you read on the clock on the wall that it was already four in the afternoon. You were again surprised by how time seemed to fly nowadays. As you thought back to the first few weeks after your mom had taken matters into her own hands, you noticed the drastic improvements you had made. During those first days, it was hard to keep your mind on anything productive, let alone school related subjects.

In the bathroom, you pulled down your pants and sat down on the toilet, hunching over onto your knees completely. You had already missed the toilet bowl completely multiple times, so you weren't taking any risks anymore. You couldn't deny that your situation had some benefits, but you still missed the days that you could pee standing up. As you relaxed, a powerful stream of pee started hitting the toilet. You were embarrassed to admit that you sounded exactly like a girl would if she'd use the restroom. When you were finished, you shook your ass up and down in your awkward position in an attempt to dry your crotch. This didn't do much, though, so you had to resort to drying it off with some toilet paper. This was how it always went, but old habits die hard.

Before getting dressed again, you opened your mom's drawer, looking for her sanitary wipes. When you pulled your pants down, you had already felt how wet and sticky your current one was. You knew your mom wouldn't mind you leaking a bit into your underwear, but you still tried to keep them dry as much as possible. After you found what you were looking for, you retrieved the dirty one from your underwear and threw it in the bin. At first, you were scared your dad would find out it wasn't his wife using the sanitary wipes, but your mom assured you he wouldn't. Skeptical as you had been at first, she turned out to be completely right. Nowadays, you get rid of them without a second thought.

You carefully put the layer of protection between your crotch and your underwear in its place and pulled up your pants. You checked another time to make sure you wouldn't leak next to it and buckled your belt. Finally, you stood in front of the sink to take another look at your crotch in your jeans. There wasn't even a hint of a bulge showing in your pants. You would be able to go out and nobody would know that you were wearing a chastity cage. You had been adverse to the idea of wearing such a small cage, but you had to acknowledge its upsides. And it was not like you had had any choice in the matter anyway.

Your biggest fear had been that someone would catch on, especially if you were at campus. The shrinking of your crotch had definitely decreased your stress while wearing your cage outside. It had protruded more obviously in your pants when you wore your bigger cage. Not that much, but just enough that some people might look twice. The only reason people might get suspicious these days would be by the distinct lack of bulge in your jeans. Even in loose shorts, there wouldn't be a hint of a bump in your pants.

While you were walking back to your room, you decided to play some games until dinner. As you sat back down behind your desk, you felt something leaking out of your penis already. It was hard to hold back, so you just let it flow into the sanitary wipe. You were almost continuously leaking these days, as your last time had been about a month ago. Your heart skipped a beat when you realized this. Every month, Mom would take care of your problem downstairs. She deviated from this with a few days sometimes, depending on your father's schedule. He naturally couldn't be home at those moments. You had no idea if today would be the day, so you could only hope. With a ragged breath and beating heart, you booted up your computer to play some games. You had to do something to keep yourself from getting too excited.

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You looked up from your PC as you heard your mom's voice coming through your door. "Honey," she called. "It's time for your milking, Sweetie. I'll be waiting for you in our bedroom."

"Yes Mom, I'm coming", you shouted back, making sure she heard you. It hadn't even been on for over ten minutes, but you would gladly turn off your PC again for this. You had been waiting for ages to be milked again. Your excitement started rising and rising. You almost sprinted out of your room towards your parents' bedroom.

When you opened the door, your mom was already sitting on the bed, playing with her tablet. You couldn't help but stand in the doorway, gazing at her. Her smooth black hair that would normally drape over her shoulders was put into a quick bun. You had inherited your hair from your father, as it was more thick and brown. You kept it relatively short to combat the curls that would start to show if it grew longer. You shared her pale white skin and light-blue eyes. Even though you had the same eyes, you could stare into hers for ages. Even so, the reason that you were staring at her was for another reason. She was wearing nothing but her underwear, leaving scarcely anything for the imagination. Her large breasts almost seemed to tear out of her purple lace bra. Her bare crossed legs and thick thighs were in full display for you to see, slim panties of the same dark purple hiding her crotch.

You gulped as your excitement went through the roof. You finally closed the door behind you, and your mom looked up from her tablet. She swiftly put it away and gave you a scrutinizing look. "I see that someone here is getting excited," she noted nonchalantly.

"I'm sorry, Mom", you said sincerely. One of the reasons that you were put in chastity was because you couldn't keep your eyes off her. It had been ages since you first started noticing her in a different light. You snuck glances at her in the living room, during dinner, or in the pool when you were on vacation. Since you started going to college, this had only gotten worse and worse. During a weekend that your dad went on a trip with his colleagues, your mom had come up with the solution.

Even though she was sitting here in some quite revealing underwear, you didn't intend to stare at her. "Oh no, I didn't mean to reprimand you, Sweetie," she said. You looked up in surprise. It wasn't unusual for her to scold you for giving her inappropriate looks, although the frequency drastically lowered when you were put into your cage. "I decided to show a bit more skin around the house," she said. "And I don't mind if you take a look now and then, if you keep it reasonable."

Your mouth almost hung wide open. Your mom chuckled as a sly smile played on her lips. "I hope you don't mind, do you?" she asked innocently.

As if woken up from a dream, you tried to mutter a response: "Ehm... N-no, I don't mind, Mom."

"Great!", she said with a beaming smile. She patted the empty spot on the bed to her side. "Don't keep standing there, come sit next to me", she urged you. It had felt like your feet had been glued to the floor, but you managed to hop onto the bed. As you sat next to her, you were still trying to not look at her, but it was almost unavoidable by how close you guys were. After the past few months, you still got anxious every time your eyes fell onto her cleavage. She had mostly worn conservative clothing, yet your eyes still felt like they were pulled on by a magnet. This was at least a hundred times worse in the outfit she was wearing right now.

"You've been such a good boy the past month," your mom started in a soft voice. She looked you straight into your eyes. "Now that you're locked up, Mommy can be sure nothing weird will happen during the day." She had a mischievous smile on her lips. You nervously licked yours, at a loss for words. "I don't mind you looking at me when you're in your little cage," she said, as she put her hand on your thigh. "But keep a minimum when your father is home. You wouldn't want him to see you ogling your mother." Her expression was deadly serious now. You nodded expressively. "Good boy," she said again, as her smile reappeared.

"Now," she said, voice louder again. "Let's get you milked before I have to start making dinner. Get those pants off for me, will you, Hun?"

"Yes, Mommy," you said. You startled right after the words came out of your mouth. After she had used the word before, you had now also called her "Mommy" by accident. You had no idea if she would allow it and instinctively kept your head down.

"Very good, Baby," she said affectionately. You let out a breath of air, relieved she didn't mind. That she was glad about it, even. Without thinking about it longer, you started undressing. You started with your sweater and t-shirt, after which you got naked completely by pulling down your jeans and underwear in one fell swoop.

It had taken months before you didn't feel embarrassed anymore to get naked in front of your mom. If you had been told beforehand that you didn't feel a thing anymore after a while, you wouldn't have believed it. You eventually got used to it after the weekly cleanups and the monthly milkings. At the moment, the only thing you felt was immense excitement. You usually were if you were getting milked, but your mom's change of heart had escalated it even further. Now that you were completely naked, you were getting ready to get on all fours. That was how you would usually be milked.

Mom would use a toy to stimulate your prostate. As you were on all fours, Mom would circle it gently around your prostate, giving you a careful stimulation. Soon you would start leaking, like you had done for the past few days already. This would ramp up to get increasingly faster, until the floodgates were completely open. While she stimulated your ass, Mom made sure she didn't give you too much stimulation. You would never get over the edge, so your milking never reduced the amount of excitement you felt beforehand. It would just increase it, leaving you hot and bothered when you were empty.

It had been tough to release for the first time. That was because it felt like you were slowly but steadily peeing, so to just simply let it go on top your parents' bed had proven to be hard for you. It had taken long for you to finally release the pressure you had built up for that month. These days, you would be flowing intensely in just minutes. Your only worries were that you had to restrain yourself from throwing your ass back into the prostate massager to get extra stimulation, and to stifle your moans, as you weren't supposed to enjoy being milked.

You felt a hand on your knee as you were turning around to get in position. "Not this time, Sweetie. Mommy has planned something else today." You looked at her quizzically, but lay back down on the bed. "Stay there," she said commandingly, although in a teasing kind of way. She got up from her spot next to you and crawled around over the bed. She did this in a painstakingly slow manner. As she crawled to the end of the bed, her swaying hips were presented right before your eyes. You had long admired your mom's behind, sneaking glances at it when you could. Her broad hips looked great in tight jeans, and her big ass was mesmerizing for you to look at. Her purple panties dug between those huge white globes, just barely hiding her vagina from your gaze. You imagined holding her ass into your hands, digging into it and kneading it. Your mom didn't have one as tight as some younger girls would have, but you loved it exactly as it was. This was the first time you had seen so much of it, even more than when she wore a swimsuit in the pool or at the beach. As you burned this sight onto your retina, your penis started pressing against its tiny prison even harder than it had already been doing.

You were slightly disappointed when your mom arrived at her destination and turned her ass away from your eyes. As she sat down onto her knees behind your feet, she frowned. "I said to not overdo it, Honey," she said, faking disappointment.

"I'm sorry, Mommy", you apologized again. "You just look so stunning", you carefully added. Your heart started beating even more intensely, this being the first time you were this daring. "Thank you Baby," she said with a motherly smile, as if I had complimented her cooking during dinner. "You also look rather handsome," she said while grabbing your package with her hand. The provocative tone in her voice had completely returned once more.

You couldn't respond to her, as you were too stunned at that moment. She would rarely touch you directly, if she had done it once at all. Only when she unlocked your cage would she come even close, but she would never put her hand on it like this. The tiny key that could set you free from your prison was safely kept on a necklace, which she always wore. It was normally hidden in her cleavage, in order for your father not to notice. At the moment, it was in proud display between her breasts, as if provoking you. You loved that she kept the key near her, and it was even greater to now be able to see it at its hiding spot.

She pulled her hand from your crotch to uncover your tiny cage. "Pull your legs behind you for Mommy, Baby," she said encouragingly. She guided your legs and arms in position, until you kept your knees close to you and your legs spread wide. This was an even more embarrassing pose than being on all fours. You couldn't put your cage on display more proudly than this. Mom bent down and looked at it intently, caressing it with a finger.

Your last cage had been less than two inches in size, already very small. It had been a tight fit, especially if you got even a tiny bit excited. When you were erect, you were almost six inches long. You were generally pretty content with that, although every man would wish for an extra inch. The problem, however, was your length when you were flaccid. You were only just a few centimeters long. That meant that if you weren't excited, you wouldn't even fill out your already small chastity cage. You hadn't been keen on telling that to your mom, not wanting her to know about your small penis. She'd had a hunch, though. Back when you were still in that cage, she had released you and allowed you to masturbate. You had imagined that that had been for good behavior, but it had been for another reason.

After she had locked you up again, you were good to go back to your room. You sat down on your bed in bliss and watched some videos on your phone for a while. Soon, you were surprised by your mom suddenly entering your room without knocking. She abruptly ordered you to pull down your pants. Slow to catch on, you did as she said. This is how you laid your actual size bare. When locked up for a while, you would normally permanently fill out your container, but now that you had had a real orgasm, your penis had shrunk to its original flaccid size. It barely filled out half of the small cage.

Just a day later, you were wearing a new cage, the one you were still wearing to this day. It was not even an inch in length. Even your penis had to be flattened to fit into that. Your balls were now more prominent in your package than your tiny cock was. As punishment for not telling Mom that your cage had been too big, she had chosen a bright pink model. As your mom was now caressing the edges of the cage, the tip of your cock was showing through the pee hole coming straight out the front of the cage. She purposely avoided touching it, as it was one of the few spots where you would get actual stimulation.

"You look great, Sweetie. There are no signs of irritation I can see. Does it also feel okay for you, Baby?" she asked sweetly while keeping her eyes on your cage. This had been the first time she had actually asked your opinion on the matter, previous times only to ascertain you weren't in pain.

"I-I usually don't even notice that I'm wearing it anymore", you did your best to respond. "That's fantastic to hear, Sweetheart," she said as she looked back at you. When she met your eyes, she saw how much trouble you were in trying to hold back your hips from grinding against her finger. "Oh, Baby," she said caringly. "Have I teased you a bit too much? Shall we start your milking?" You could only nod, silently begging her to start.

Mom got up from the bed and swiftly took out a few items from her drawer as you were lying on the bed, legs spread wide. She returned and said: "Get ready and relax, Honey." You let out a sigh as a lubed finger met your sphincter. The touch retracted soon after, but the feeling of the lubed massager took its place. You looked at your mom as she was sitting in between your legs, busy with your ass. Your eyes drowned in her cleavage while her gaze was fixated on your bottoms. In one press, the massager disappeared into your ass. You were not concentrating on holding back, so you accidentally let out a soft moan. You abruptly shot a frightened look at your mother. She had been very adamant the last couple of months on you not enjoying the milking, so you definitely should not be moaning during it.

She had once even given you a spanking, which you had felt for days. Instead of doing that, however, she responded differently this time. "Just relax, Baby. Let it all out for Mommy," she softly said with a caring look. It was as if a weight fell off your shoulders, and moans immediately started coming out of your mouth as the massager circled around your prostate. Your tiny penis immediately responded by starting its stream of sperm. Your mom took out a towel and put it on your belly to catch most of it. She kept circling around the massager in your ass, stimulating the prostate skillfully. It was completely different to be allowed to enjoy it, but that was not the only thing that was different. The massager somehow felt weird, something you couldn't quite put your finger on. It felt just as good as normal, but it wasn't the same. The other thing was that your mom was bringing you much closer to the edge than she normally would. Usually, she wouldn't even bring you close to the edge, just to be sure you wouldn't get any enjoyment out of it. This time, she was walking the edge like a tightrope, bringing you frighteningly close.

She did this for a few minutes. Meanwhile, a tiny but steady stream of sperm was leaking out of your little prick onto the towel. You hadn't started leaking as much as you could, but that wouldn't take long. As you were waiting for the moment where you had to let go completely, your mom seemed to have other ideas. The circling motion around your prostate increased in intensity and additional motions were added. Her light-blue eyes stared into your increasingly panicked ones.

"Mommy, I... I-", you whimpered. Your mom bent down over you, one hand still busy with your ass. She put a finger on your lips.

"Don't worry, Baby. Let it all go for your Mommy," she whispered in your ear. She inched lower, until her lips started gently kissing your neck. You would never have been able to handle this, let alone after months of being locked up tightly. Added to all this, was a sudden shock you felt throughout your entire body. Deep in your ass, something had started vibrating. The sudden stimulation onto your prostate was too intense. You made an audible gasp. You heard a chuckle between her kisses on your neck and shoulders. "An extra surprise for my good locked-up boy," she whispered.

You were now fully throwing your ass back into the vibrator, all sensibilities you had learned the past few months thrown out of the window. You were still dutifully keeping your legs back, so it came to be a pitiful motion. "M-Mommy, I-I'm really cumming!" you cried out.