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It was a boring Saturday, the same as the day before. A seemingly endless thunderstorm had canceled Charlotte Lunaire’s weekend plans of going to the beach with her friends, and so she was stuck inside. Even worse, she was stuck studying. That was because Ilya, her manservant, was tasked with making sure she did well in school. And because they were both in the same class at their college, Ilya knew she had plenty of studying to do.
So it was the second day in the row of Ilya making Charlotte catch up with her schoolwork while the rain drizzled down the window panes of the Lunaire manor.
“I’ll be right back, keep working.” Ilya said. He set down his phone. Charlotte looked up at him and couldn’t hold back a giggle on seeing his face. Charlotte had convinced Ilya to let her do his makeup today to pass the time, and it amused her how cute she had made him look. While Charlotte did feel like time took forever when she was cooped up in the mansion, it was entertaining to mess with Ilya.
An expensive set of deep red lipstick, dark but subtle eyeliner drawing out his pretty eyes, sparkling pink and white earrings to match his hair ornaments, and even a choker collar that Charlotte had convinced Ilya would look adorable. And indeed he did, but Charlotte wanted to push him further. Charlotte was thinking about what outfit to make Ilya try instead of his usual comfy hoodie, shorts, and leggings. Charlotte wondered to herself how Ilya would look in a skimpy nightgown, and laughed at the mental image.
Ilya ignored Charlotte’s stare and left for the bathroom. As soon as Ilya left, his phone buzzed. Charlotte couldn’t help but glance at the screen, and saw the message displayed.
From: Melissa
Heyyy, do you think you can still make it tonight? ;) Or is that sleepyhead brat causing problems again
Charlotte huffed in annoyance. She knew Melissa from their 9AM class on Tuesdays. Charlotte was always so groggy having to attend class so early, and Melissa always seemed so bright and cheerful. Charlotte resented Melissa’s ability to be so alert so early in the day. Even more, Charlotte resented that Melissa was so friendly and chatty with Ilya.
Charlotte rolled her eyes as she wondered what Ilya saw in a girl like Melissa, a coffee-charged 9AM flirting floozy. Charlotte doubted Ilya and Melissa were dating, since she always presumed that Ilya was single. Plus, Charlotte expected Ilya to have better taste than to choose Melissa. Still, Charlotte wasn’t absolutely sure. In a petty move, Charlotte removed the notification after opening the text, making sure that Ilya would leave her on read.
Charlotte’s bored mood changed to annoyance. And when Ilya returned, he noticed that Charlotte was now tapping her foot with her arms crossed, glaring at him with a new look. “What? Did I miss something?” Ilya said, wondering if he did something to upset her.
Charlotte had been thinking about how to deal with Melissa texting Ilya, and had come up with a plan. But first, she had to goad Ilya into agreeing. “I was just thinking. Men need women to manage them, because they can’t keep their dick in their pants.” Charlotte said the statement like she firmly believed it, planning to try to bait Ilya a bit. Of course, she didn’t truly believe something like that applied to all men, but she knew it would goad Ilya into responding.
Ilya was caught off guard by the sudden topic. “I don’t agree with that. Men don’t need women.” He suddenly thought about the words he said, and hastily added more. “Not that I don’t value women- I just don’t agree that men can’t function without women. You understand what I mean, right?”
Charlotte kept a straight face, making sure not to show her joy at Ilya reacting exactly as she expected. Because Ilya took her bait, she carefully laid more for him. “No way. All men just think about sex all the time, and nothing else.” She chose her words carefully, her entire plan depending on Ilya falling for her taunting. “In fact, I bet you wouldn’t last one month without sex or masturbation.”
Ilya coughed and turned a bit red suddenly in response. Charlotte had made sure to single him out instead of just men in general, and she watched with glee as he became flustered as the topic changed to his masturbation habits. “I- who said that I even masturbate that often?” Ilya tried to deflect it, and Charlotte pounced on the opportunity. She also had some smug satisfaction as he subtly confirmed that he was in fact single and not having sex.
“Don’t act like I don’t know- all you men are animals, I hear you do it every day, multiple times a day.” Charlotte tried to sound as innocent as she could. Of course she was not about to reveal how often she masturbated, but it was entertaining to her to tease Ilya about it.
Ilya shook his head no, blushing even more. “N-no! I don’t do that! You’re totally wrong, and I could definitely survive without… masturbation.”
Charlotte immediately responded. “So prove it. Go one month without masturbating or having sex.” This was Charlotte’s plan, her entire goal. While she would never in a million years admit to it, she was bothered by Ilya texting another girl and wanted to make sure he wasn’t just having sex with her.
Ilya rolled his eyes. “I don’t need to prove anything to you. Besides, how would I even prove that?”
Charlotte grinned. “I have a way to make sure. But sure, how about we make it a bet instead. If you go a month without masturbating or having sex, or asking me for permission to do so, then you win… Well, I’ll give you a one week vacation, paid.” Charlotte saw Ilya’s eyes light up at the thought of a paid vacation, and she thought about what she wanted most from Ilya. After all, she was absolutely certain that Ilya would lose. “If I’m right and you can’t last a month, then you let me spend one week choosing every single outfit you wear and dressing you up as my doll.” Charlotte giggled, excited already as she thought of all the adorable outfits she could make Ilya wear.
Ilya blushed a bit at the thought of letting Charlotte dress him up more, but he couldn’t imagine losing this bet. So to Ilya, it was just a free vacation along with the chance to prove to Charlotte that she was wrong. “Alright, I accept. This will be so simple, and I can’t wait to see your face when I say I told you so.” He then paused. “Wait, but how will you make sure?”
Charlotte smiled, and walked over to Ilya. “Oh, it will be very simple. But for this to work, you will need to obey my orders and let me make sure you aren’t cheating.” She waited for Ilya to nod in agreement, and she grabbed a small bag from a closet. “First of all, put this on.” She handed Ilya a blindfold, made of leather and clearly meant for no light to reach his eyes.
He looked at the blindfold, and then looked at Charlotte with suspicion. “What does this have to do with our bet?” Ilya asked. He had been fooled by Charlotte many times before, and he wasn’t excited about being toyed with again.
Charlotte flashed her most innocent smile at Ilya. “Don’t worry. I just don’t want to spoil the method to make sure you can’t cheat, or else you might figure out a way to worm your way out of this bet.” She giggled. “And you did agree to obey my orders for this bet, after all. So if you are going back on your word, then I’ll have to declare myself the winner of this bet…” Charlotte of course took no time using the bet as power over Ilya, knowing that he would hate to lose both his vacation and bragging rights.
Ilya frowned, but he eventually pulled the blindfold up and over his face. “Alright, fine.”
Charlotte continued her instructions. “Alright, hands behind your back, and keep them there.” She then crouched down in front of Ilya, making sure he was totally unable to see by waving her hand in front of his face. Ilya obeyed, standing in a submissive pose with his hands crossed behind him.
Charlotte was satisfied he was blind, and pulled the custom made metal chastity device from the small bag. Without warning, Charlotte took hold of his shorts and leggings from the side, and tugged them down to his knees. Ilya squeaked in surprise, and reached to grab his shorts. “Hey!” Ilya exclaimed. “What are you doing that for?”
Charlotte snatched Ilya’s wrists and with practiced ease clicked handcuffs around each wrist, trapping his hands behind him. His hands grasped at thin air, not able to grip his shorts and pull it up. “Don’t be silly, and behave. I specifically told you to keep your hands behind your back.” Charlotte patted Ilya on his cute butt as though to comfort him. “I need to do this to make sure you don’t cheat. It’s not the first time I’ve seen you naked.” Charlotte did her best not to giggle looking at Ilya’s now slightly hardening penis in front of her. As much as it amused her that he was getting excited from her attention, she had to work before it got hard.
So starting with the ring, she worked it over Ilya’s balls and then pulling the shaft through. He grimaced at the cold feeling. “Hey- what are you doing touching down there?” Unable to see, he didn’t understand what she was planning. Charlotte didn’t respond, now taking the other part of the cage and squishing it over Ilya’s dick, squeezing it in place and trapping it inside the unyielding metal. It was designed to fit him exactly, so it was fairly simple for her to trap Ilya inside the chastity device. Then with a click, she locked the device’s internal lock and tucked the key away for safekeeping.
Ilya felt the squeezing embrace of the chastity cage, and was suddenly very worried. “Hey, I’m not sure I agreed to this…” He said, as his excitement made him ache slightly from the squeezing embrace of the cage keeping him from getting hard.
Charlotte explained to him. “This is a chastity device, Ilya. It will make sure you can’t cheat, even if you want to. So for you to win this bet, you will have to wear this for one whole month. And if you ever ask me to remove it, I’ll assume you give up and that I win the bet.” Charlotte grinned as she pulled Ilya’s shorts back up, covering up his now trapped dick and balls. This was her true plan, to lock Ilya up and keep him under her control. This way, he couldn’t go and flirt with anyone without her permission. Of course, not that she would ever admit that it bothered her if he was attracted to other women.
“Well, can you at least take off these handcuffs, please? I don’t- mmph!” Ilya was cut off by a rubber penis being suddenly shoved into his open mouth. Charlotte buckled a few straps around his head, forcing Ilya to take the whole penis gag in his mouth and bite down on it, silencing his complaint.
Charlotte gently pushed down on Ilya’s shoulders, forcing him to kneel in place. “Oh, no no no. Why would I do that when you would just make me study more tonight? No, I think I’ll have some fun teasing you and seeing how you react to being locked up in chastity…” Charlotte giggled, excited to tease her friend even more.
Charlotte bent over and snapped another pair of handcuffs around the chain between his handcuffs, and closed the other end around the leg of the table they were studying at. With that, Ilya was very simply chained in place, helpless to escape and try to find Melia. After all, Charlotte didn’t want anyone to interrupt her fun. This was the most exciting thing to happen all weekend.
Then without warning, Charlotte laid down next to Ilya, placing her head in Ilya’s lap. She rested her head right on top of his locked dick and giggled as she stroked his thigh, feeling how he squirmed underneath her. “There there, calm down. I’ll cuddle up with you, doesn’t it feel nice to be so close?” Charlotte purred in the most seductive voice she could, trying to get a rise out of Ilya.
Of course, Ilya only moaned in response. Blindfolded, gagged, and bound, he was extremely aware of Charlotte so close to him. Every move that she did so close to his crotch made him react a little, and Charlotte was extremely amused by how on edge he was. She nuzzled a little closer with her head, and let out a long breath. “Oh my, the things I could do to you if you weren’t in that cage right now… I bet you’re imagining them right now, aren’t you?” Charlotte teased Ilya, trying to make his imagination work against him. Charlotte knew that Ilya was easy to tease, and expected that keeping him in chastity was going to be so much fun.
Ilya whimpered, his dick unable to even get hard as she kept pressing her warm body against him. He felt her press her breasts against his leg, and Charlotte smiled at his squeak. “Ah, too bad I cuffed your hands, you don’t get to touch my head, grab my hair, and do all those dirty things you’re thinking of… Oh wait! You’re locked up anyway, you can’t.” Charlotte laughed, ready for a fun month of teasing Ilya for being trapped.
Charlotte made the most of her bet with Ilya for the next few weeks. Multiple times a day, she would interrupt whatever Ilya was doing and require that he prove that he was still locked in the chastity device. Of course, Charlotte had the key tucked away safely on a necklace that she never took off, but she enjoyed the power to at any time make Ilya humiliate himself by showing her his caged penis. And after Ilya once took too long fumbling to undo his shorts to prove his part of the deal, Charlotte had all of Ilya’s work clothes temporarily locked in her closet, replaced with a maid uniform. Charlotte claimed it was to be able to flip up his skirt for an inspection, but she also got to enjoy how adorable Ilya looked as a maid.
But after the fourth week, Charlotte noticed that Ilya had a smug look on his face every time she inspected his cage. Charlotte’s face soured when she noticed it, as she looked forward to Ilya feeling shame during inspections. She immediately had to know why he was acting like he was in control. “What made you so happy?” Charlotte snapped at him, crossing her legs as Ilya lowered the skirt on his maid outfit. As always, the inspection concluded with nothing Charlotte could use to claim he violated the bet.
Ilya’s grin broadened. “Well, I only have two more days until I win the bet. And I am really looking forward to that vacation.”
Charlotte’s eyes bulged momentarily, and Ilya caught a glimpse of Charlotte’s unmasked emotions. Charlotte suddenly realized that she was both going to lose the bet and unlock Ilya at this rate. And she was excited about neither of those things. She had grown to love this control over Ilya’s manhood, and was not about to give it up.
So Charlotte quickly excused herself to set up a plan. After an hour of brainstorming and prepping, she decided she had a simple and foolproof plan to make sure Ilya couldn’t win the bet.
“Ilya?” Charlotte called out to him loudly from her bedroom. “Please come in here now.” She used the tone of voice she took on as his employer, the way she talked to him as a servant. “My bedsheets need fixing, did you forget to do it?”
After a moment, she heard Ilya’s footsteps approaching, and he came inside. “I’m pretty sure I already made your bed, Charlotte.” Ilya said, a slightly confused look on his face. He glanced at the bed and saw that the covers were a bit jumbled still, like they always were after Charlotte groggily woke up in the morning. He sighed and accepted that his memory must have been wrong. Ilya stepped forward and pulled the top cover off of the bed, planning to go layer by layer.
But to his surprise, Ilya found no sheets or blankets underneath the cover. Instead, there were four horizontal leather straps running across the bed with various smaller straps and buckles attached to them. Ilya struggled to process what they were, and Charlotte took advantage of his confusion to push him onto the bed from behind.
Ilya fell with a grunt, and Charlotte quickly pounced on him. Flipping him around and trying to grab his wrists to gain control, Charlotte maneuvred Ilya into position. Each of Ilya’s wrists were fed into waiting padded leather cuffs at his waist, which were pulled tight, buckled, then locked shut with padlocks. Without wasting any time, Charlotte then secured his ankles into matching cuffs attached to the strap at the foot of the bed.
With just those four cuffs, Ilya was bound lying face up on the bed, his arms restrained right next to his waist and his legs spread slightly. “Hey, get me out of this! You’ve been messing with me enough, let me go!” Ilya struggled a bit against the cuffs, but with his weight now on top of the straps around the bed, it was impossible to pull his arms up or away from the bed.
Charlotte then wrapped cuffs attached to the top-most strap around Ilya’s upper arms, making him unable to even move around his elbow to struggle. Then after that, the last pair of cuffs went just above Ilya’s knees, pinning his legs just as securely. Charlotte then pulled four waiting straps from under the bed, and fed them over Ilya’s body. One over his shoulders, one over his waist and arms, one over his thighs, and one over his calves. Each strap was buckled shut and pulled tight, and along with the cuffs holding down his limbs, Ilya was now pinned to the bed.
Charlotte took a breath and grinned. “Well, it’s very simple.” She took a web of leathery straps and got onto the bed right on top of Ilya, pressing her body down against her pretty captive maid boy. “I know you have been using some cheap strategy or something to win this bet, so I’m making sure to even the tables a little bit. I’m going to spend some quality time with you tonight, and remind you just how much you want to ask me to remove that cage you’re wearing…” Charlotte winked at Ilya, bringing the large ball attached to the web of leather towards his mouth.
Ilya shook his head. “I haven’t cheated at-” And then Charlotte cut him off by pushing the ball of the gag into his mouth and past his teeth. It was one of her favorite toys, perfect for reminding Ilya that she decided when he was allowed to speak. The leather straps of the attached head harness were wrapped around his head and pulled shut so he couldn’t spit out the gag, and with each strap tightened Ilya’s mouth was forced closed around the firm silicone. Ilya squeaked quietly, but it wasn’t quite as muffled as she wanted.
“Now, to make you even cuter and helpless in that gag…” Charlotte took a shiny latex mask, and put it over Ilya’s face. The stretchy material covered his face from below his eyes, and helped push the ball of his gag further into his mouth and prevent him from forcing it out. She then fed the four latex straps through the straps of the harness gag and behind his head, pulling off paper strips to reveal glue tabs on each strap and attaching them to the matching part behind his head as tight as she could. When she was satisfied, Ilya’s face was muzzled and masked by a tight latex mask and the straps of the harness, but the ball of the gag and his lips were sealed away. He whimpered, and it was just as cute as Charlotte wanted.
Charlotte then pressed her full body down against Ilya’s like a lover would, and she whispered in his ear. “If you really think you deserve to win this bet, you’ll just always shake your head no when I ask if you want me to remove your cage.” She giggled, and gave him a tiny teasing nibble on his earlobe. “But, if you say yes, I promise I’ll make you feel amazing…” Charlotte rubbed her body against Ilya’s, feeling him weakly move his hand in a feeble attempt to struggle and squirm.
Charlotte stood up, and walked over to the side of the bed. In full view of Ilya, she bent over and wiggled her butt as much as she could as she pulled her pantyhose down her legs bit by bit, trying to put on as much of a show as she could. When she glanced back, she saw Ilya was blushing bright red, and she giggled at the effect she was having on her prisoner.
Then after the pantyhose was removed, she returned to the bed. Now sitting down on Ilya’s chest, she made sure to adjust her skirt so her panty-clad ass was resting directly on Ilya’s maid uniform. She leaned over and pulled the warm pantyhose over Ilya’s eyes and looped it around the back of his head, wrapping it around him twice before tying it off. It didn’t totally blind Ilya, but she hoped the knowledge that she had just been wearing those pantyhose would excite him.
With Ilya partially blinded, Charlotte was bold enough to adjust so her knees were on either side of Ilya’s head, and she was facing his body. She put her hands right next to his and leaned forward. Without a blindfold, Ilya would be enjoying an upskirt view, but instead he could only just make out her shape without the details. And from the groan she heard from Ilya, Charlotte knew that he wished he could see more.
Charlotte then flipped up Ilya’s skirt, revealing the chastity cage currently nestled in the black panties that Charlotte had insisted were part of a maid’s uniform. Charlotte ran one finger along the edges of the panties, knowing just the vibrations from her finger moving would tease him. Ilya tried to shift and squirm away, and in punishment Charlotte lightly slapped his thigh. “Behave.” She ordered.
Charlotte bent over more, and giggled out loud to make sure Ilya would hear it. “Have you ever had these removed by someone’s teeth, I wonder?” She took hold of the edge of his panties between her teeth and took her time pulling them down. After his panties were pulled down, Charlotte hovered with her mouth right above his caged dick, blowing on it softly. With every breath she felt Ilya quiver, shaking with excitement.
Just from this little bit of teasing, Charlotte could tell that all of Ilya’s earlier confidence was just bravado. “Does that feel good?” Charlotte exhaled a little harder, making Ilya twitch. “Well, can you imagine how good it would feel to be touched?” Charlotte loved the feeling of teasing him, and was confident that Ilya would overheat thinking of being touched by her.
In truth, Ilya was extraordinarily pent up, and the feeling of being in her control was getting to him. He would never admit it to her face, but he was so excited being restrained and underneath her. And so just the breathing was enough to tease him, and make him whine for more.
Charlotte glanced back at Ilya’s face, now fully red as he breathed faster. “Do you want me to remove your cage?” Charlotte asked seductively. She saw him hesitate for several seconds and quiver, but Ilya shook his head no. Charlotte wasn’t worried, since she had plenty of time to make him submit.
Charlotte then did one more long breath at his cage, before gently brushing her lips against the metal tip of the cage, but then no more. She stood up again and went to grab her preferred tool for tonight. “This is a special vibrator, it’s quite strong.” She brought the wand vibrator to the bed and laid down right next to Ilya, wiggling in close to his body. She turned the vibrator on, and the loud noise made Ilya jolt.
Charlotte ran her hand over his bare thigh, bringing the vibrator close. She left it in the air just far enough away, and watched as Ilya wiggled in place. She could tell that Ilya was quivering in anticipation, and maybe fear. Then with a gentle touch, she brought the vibrator against Ilya’s groin above the cage, pushing in a bit. Ilya arched his back as the vibrator brought him far more stimulation than he expected. It was an intense feeling despite not even touching his crotch. He moaned out loud as Charlotte moved the vibrator left and right, and then around and below his balls. Then with a grunt, he was surprised as she pulled the vibrator up, just a bit away from his balls.
Charlotte watched as Ilya gasped for breath and leaned his crotch forward to try to get just a little bit more stimulation. He was nowhere near an orgasm, but this was the most excitement he had felt in the entire time he was caged, and he was desperate for more.
Charlotte kept him straining to reach the vibrator for a moment, before straddling his hips once more. She pressed the vibrator against his cage again, now pinning the vibrator between their crotches, so that she felt the pleasurable vibrations through her panties as well. She leaned forward and rubbed her breasts against his chest, bringing her mouth to his ear. She asked him once more, her more excited whisper revealed she was enjoying this quite a bit as well.
“Do you want to remove your cage? Do you want to cum?”
Ilya groaned in response. The vibrator felt so good. Charlotte’s heat and smell around him were so close and intimate. He was so horny from not touching at all for nearly a month. And Ilya felt so good after being in Charlotte’s control for a month.
But Ilya also had so much pride. He would have to admit he lost to Charlotte. He would have to let her dictate his outfits for a whole week. He would lose the paid vacation he wanted so badly. And he was so close to making it the whole month.
But he was also so close to an orgasm.
Ilya strained against the bonds, and Charlotte pressed the vibrator tighter between them.
Charlotte’s breath was heavy on his ear. Ilya’s breath was fast through his nose.
Finally, Ilya came to his decision.
He nodded his head yes, submitting to Charlotte. He knew he would regret letting her win, but he needed to cum. And Charlotte giggled as she whispered in his ear. “Good boy.” She pushed the vibrator right over his cage, making Ilya squeal.
“I’m afraid I’m not going to take your cage off, though. But since you already lost our bet, I might as well make you cum in shame.” Charlotte laughed at Ilya, and the strict gag muffled his angry scream as he realized that Charlotte had tricked him. Even though Ilya had conceded defeat, she had never promised she would remove the cage.
Charlotte turned up the vibrator to max, and took full joy in watching the defeat in Ilya’s eyes while he came for the first time inside of a chastity cage.