The Babysitter - Beth

"What could you have done wrong in your bedroom some days ago?" I asked.

"I came without your permission," he spat out.

"So true, pet," I agreed. "It's not how I want to deal with you, but disobedience must be penalized. I guess you think so, too. It's up to you how long it takes to be an obedient, submissive boy."

His cheeks turned red, and I saw the doubt.

"I can't force you to wear it, but I would like you to. If you want to be trained correctly, you have to show trust and give in to my demands. Wearing this chastity device would signify you want to belong to me. What do you think, boy? Oh, and I would like to add, wearing this would make me incredibly aroused." He gulped down his doubt.

"Yes, Miss," he whispered obediently.

That was a better answer than I had hoped.

"I'm so happy to hear that, pet, but there is one problem." I massaged his raging hard-on. "Can you make this big defiant tool soft for me?"

"I don't think so."

I shook my head.

"Boy, boy, what should I do with you? You have such a lack of willpower. Sure, you can do it! Jerk off!" I ordered, nearly bursting with amusement.

I released his cock as he reluctantly stroked it. He was visibly uncomfortable doing it while I observed.

"Come on, boy," I hissed. "I'm sure you can do better. I am not going to do it for you. It's not about pleasure; it's about getting you soft. Stroke faster."

He increased his speed.

"You act like you never have wanked before. I expected you would have considerable experience with this." I rolled my eyes.

"You know how to do this! Massage your balls with your other hand. Can you even not get off by yourself? Rub as fast you can, slut." I added, hoping the humiliation might help.

"Think of the cage. Do it for me. Think of me locking you up. Think of the hard metal surrounding your cock. Think of you being unable to get an erection because of the hard metal. Stroke harder, boy. Arousal will be painful in the future, and I will permanently arouse you because you are my slut, and I love to hurt my sluts. Faster boy. Cum now!" He exploded.

"Finally!" I sighed in relief.

Reluctantly, his penis softened. It would only be a matter of time before he became hard again, so I fastened the cock cage on him quickly. I grabbed his hair, bent his head back and kissed him. My tongue invaded his mouth; I was the conqueror, and he was my prey. I would have liked to have him hard again, but the cage prohibited that. His whimpering and groaning were enough to prove his arousal. I broke away from him.

"Thank you, Mistress." He whispered desperately and humbly after I released him from the kiss.

Mistress! My heart seemed to explode in bliss. He was so much fun and a perfect pet.

The Next Week

I accepted it as a challenge to tease him to discomfort regularly while wearing the chastity device.

I texted him periodically with messages such as, "I'm thinking of you while taking a shower and having great fun with the steamy water of the shower head, massaging myself.", "You can imagine how I'll fuck the brains out of you when you get free of the cage."

I emailed him pictures, such as one of me wearing a tight shirt, teasing my nipples. In another, he could only see me licking my lips. I ordered him to reply with how he reacted, looking at them. I phoned him and made him describe how he felt wearing the device. What are sluts for if they don't prove your power over them?

In amazement, I told my girlfriend and slave, Kate, about my putting Sam into chastity. Kate and Sam were very different. Sam tried to be my obedient slut and hated failing. Kate was submissive to me, too, but much more on the masochistic side. She earned my wrath by purposely making mistakes or speaking without thinking first. She could be such a brat and was always like a wild horse that I enjoyed having to tame repeatedly.

It didn't surprise me that Kate thought I was joking with her about Sam, but as her domme, I had never lied to her; I was slightly annoyed at her disbelief, but I wanted to play with her at the same time. Proving her wrong seemed an excellent opportunity to embarrass her, but in typical Kate fashion, she would soon forget her transgression.

I sighed.

"Do you think it's hot that I can do this to a much older man?" I asked her. "What would you do to a man in a chastity cage?"

Kate had a slutty mind and a sadistic side.

So I said, "I see it's hard for you to believe me, but I'll prove it to you. He will be at home tomorrow morning without his kids. You can do whatever you want to him, except be too cruel. Come to my place afterwards, slut."

Kate Meets Sam

It made me horny as hell to know Kate visited Sam that morning, and I couldn't wait for her to come back. When she finally arrived, I ordered her to strip and kneel. I put one finger between her inner labia and slid it slowly up and down while awaiting her report. She was immediately very wet.

"I... I visited him and proved with a grab of his crotch that he was really in chastity. Oh, it's a shame I didn't believe you, but on the other hand, would you have let me visit him if I had? I don't know. As I felt the chastity device, I... I got a fit of laughter, took his collar, and pulled him to the middle of the floor. I pushed him on his chest. He stumbled through the hallway in the direction of the living room. The door was open, and I pushed further until he fell backwards onto the couch, where he landed in a sitting position. It was so incredible! He had no idea how to handle the situation. I stripped naked, mounted him, and then began to ride him. I rode up and down his cock cage. It was so hot. I... I..."

She had a massive problem continuing her report because of her rising horniness. I increased the pace of my finger gliding up and down, and in addition, I teased her clit with every upstroke. "Tell me more," I ordered.

"I rode him until I... I had a massive..." she stammered. She was close to another orgasm, so I removed my hand before she came. I wanted to deny her. "... orgasm... " she squeaked in disappointment. Kate's whole body shivered. "Beth, please, please, I..."

"I want to deny you," I replied coolly. "I will bring you close to an orgasm many times, but I will not let you cum."

"Beth!" she shouted angrily, protesting in wild fury, but that was all she could do, and she pouted. It wasn't long before she was on the brink again.

"You stopped reporting, and that will definitely not help you," I noted.

Kate shivered in a mixture of arousal and anger. "... massively. Oh, it was so hot to feel the hard metal of the cage under my..."

I stopped teasing her. "No, Beth, please, let me, make me... " Kate pleaded.

"Go on!" I said.

"... massive orgasm, and I put my clothes on and left him sitting on the..."

I laughed. "Go on, don't stop now."

"I'm, I'm, I'm going to..." she gasped.

"You are not." I removed my hand again.

"And... and then I left him, his pants full of the smear of my... Aaargh..." I teased her further.

"... pussy on his pants and... left... " I only teased her clit now.

"...left... left the flat. He is such a... uuuuh... wimp."

I gave her a brief respite from relating her story but probed her later about Sam often, sometimes asking for more details. I brought her to the edge several times but never gave her release. I had forbidden her to masturbate for the next while, knowing that would bring out the wild horse in her, and that is what I wanted. In Kate's case, it was better she not wear a chastity belt. I knew I could trust her; if she weren't allowed to orgasm, she wouldn't. I also knew she was very impulsive and frequently touched herself without realizing it. I was certain my demand made her life more difficult.

The Day Of The Slut Contest

The great day came when I would remove the cock cage permanently—maybe. Beth and Sam were in a fantastic mood and horny as hell from being denied any sexual activity for days. I let her strip at the beginning of our meeting because merely seeing her beautiful naked body would cause pain to Sam's cock. I hadn't told Kate what this meeting was about, but she did a strip tease as if she were on a stage. Sam sighed and growled during the exhibition.

When she finished her sexy performance, I stripped, too. I'm not a classic beauty, but Sam and Kate admired my defined, athletic body. "Now, put on a good show for Sam," I ordered.

I strolled over to Kate and teased her clit and cunt while kissing her passionately. As I expected, she was wet before I touched her. With slow circling strokes, I took her to the brink of an orgasm. Kate did everything she could to give Sam a good time. Of course, I didn't make her cum; I stopped teasing her shortly before that. I wondered what she thought about it. Perhaps she couldn't think because her intense horniness restricted her thought processes.

"Beth!" She shouted with outrage. "You are such a beast!"

I loved how she couldn't control her tongue. I laughed out loud, grabbed her hair and moved her mouth to my clit. "It's your turn to make me cum, slut, and time you learned your place."

She was always obedient and would put all her energy into making me cum as intensely and satisfyingly as possible. It wasn't long until I experienced a massive climax; it was very good indeed! I had to cum, to calm myself down a bit. I didn't want to be distracted by my passion while sitting in the driver's seat of this session. I was quite happy no one could forbid me an orgasm. If I don't cum at least every other day, I get irritable, and that is no fun for anyone, I can guarantee.

I drew her head back by her hair. "Good slut! You performed very well."

After catching my breath, I explained a game I had devised. "Sam, I will remove the chastity belt, and you will both participate in a contest. Sam, your goal is not to cum. Kate, your challenge is to make Sam cum, but you also may not cum. If you can make Sam cum, you will get a reward. Sam, you will let Kate do whatever she needs to succeed. Don't push her away. If you fail, Sam, you will wear this belt much longer."

I laughed in the thrill of anticipation. It wasn't easy to remove the chastity belt. Sam's member was already swollen, and as soon as his dick was free, it immediately swelled to its full majestic length and girth.

"No problem, Beth!" Kate said, licking her lips as she observed the cock. Sam's facial expression was one of hopelessness. Kate's following comment didn't make Sam's situation any more optimistic. "Do you remember when I rode you on our first visit? You do not have the slightest chance of winning. Let the games begin!"

I had to suppress a chuckle as Sam's erection grew larger. Kate could not contain her giggling. To start, Kate blew air about his cock, and it twitched like it was on a string. I couldn't imagine Sam would stand it for long. Kate then surrounded the tip of his cock with her tongue. Sam's face showed desperation. Kate's confidence and expertise were amazing and a big turn-on. I fingered myself vigorously because I had no rules to follow. Sam refused to cum despite the repeated stimulation. I didn't know some men were able to control themselves with this much encouragement. Kate brought him close many times, but it was a miracle he managed to restrain himself and even calm down.

Kate was not in a hurry. She carried on as if it would only be a matter of time before she would win, and every time he got close, his resistance wore down. I thought Kate may be right in her assumptions, but she would lose concentration due to her desire for orgasm. The prospect of being rewarded allowed her to dismiss distractions, and she became a skilled expert who shoved away barriers like a bulldozer. It is unfathomable how Sam survived this expert teasing; his desperation increased every moment. After teasing him for a while with her lips and tongue, Kate slowly and effortlessly took his whole cock in her mouth.

Sam watched in disbelief, and his face paled as she giggled while gulping and massaging his cock with her mouth and throat, then she suddenly released it. Surprised, he looked to see her licking her lips in nearly bored confidence to win this game, and I wondered why he hadn't come from watching her. Although he didn't, it was evident all his resistance was blown away.

"Now to the grand finale!" I laughed.

Sam had resigned himself to more days or weeks wearing the cock cage, with the rationale, If I am going to lose, I should enjoy it as much as I can. His whole body shivered, sweat running all over him. I was sure this would be over in seconds.

"Stop!" I ordered. Kate set Sam's twitching cock free.

As I expected, Kate protested immediately and loudly. "He was so close! You knew he couldn't hold back much longer," she whined.

"Shhh, shhh, shhhh, Kate," I responded. "I know that. You are a fantastic slut. But what do you think? Has Sam proven his stamina?"

Kate pouted in disappointment. "Yes," she replied, then added, "For a man! I was so close to winning this game; it's unfair to stop now."

I chuckled. "I know. I saw that, and you didn't lose. But Sam didn't lose either."

"I will be rewarded?" Kate asked excitedly.

"Soon!" I replied and squeezed Sam's nipples, forcing him to scream.

"Cum!" I ordered, and he exploded in a massive orgasm.

I relentlessly teased his nipples again, and his cock hardened again. I ordered Kate to fuck him, which she did furiously, making herself cum while I teased her nipples and breasts. Finally, Sam roared, came once more and nearly passed out. I declared it a very successful evening.

The Spanking... And More

Sam wasn't a masochist. He was submissive, which was why he tried to endure the pain I caused him. I also have a sadistic side but have always been good to my slaves. They were trusting, loving people, so I never exceeded their hard limits or injured them. I take care of what is mine. Since Sam was not a masochist, he didn't have the ability to transform the pain into sexual arousal but tolerated it to be obedient. I was happy and proud to have two such wonderful sluts.

The children were away from the house when I next visited Sam to discuss a spanking session, which he agreed upon. I handcuffed him to the bedpost in an uncomfortable position. He had to kneel to lay his upper body on the bed so I could effectively spank him. I brought different instruments and began with a carpet beater. It made a lot of sound but didn't inflict much discomfort, but he twitched with every clap, knowing this would only be a warm-up. Later on, I switched to more beastly and effective tools. I used a paddle, then a leather whip with seven strings and hard knots at the end, that inflicted measurable pain.

He took the paddle well, but after a few strokes of the whip, he began sobbing but never complained, knowing it gave me pleasure. Having his trust and obedience was such a rush. I announced 50 beats and let him count. He missed a count twice, so I started at the beginning. I gradually put more force into every lash. He sobbed like a child between counting; he was so adorably sweet. This time, he managed to endure the pain to the end. Afterwards, his upper body fell onto the bed, and he cried nearly uncontrollably. I carefully removed the handcuffs, sat down beside him, and placed his head in my lap. I caressed him and whispered how proud I was of him, how strong he was and how I enjoyed his submission.

I sent a text message to Kate, who arrived a half-hour later. Sam, naked, opened the door to her and turned to present his red-striped back. I decided to let Kate live out her sadism with Sam. I suspected Kate secretly wanted to be my only slut. It's not that she didn't like him, but I was sure if she could inflict pain on him, she would enjoy it. She wanted him to give up so she could be mine exclusively. This was another side of Kate I found exciting, so I often played with them at the same time.

It was a joy to let her express herself with Sam, but I always kept her in check. As I said, I never wanted my sluts seriously injured. Although Sam was not trained in anal, I decided it was time he had the experience. I gave her a medium-sized strap-on, which I thought Sam could take, perhaps not easily or painlessly, but he could do it. I made Sam suck on the strap-on's phallus first. It was such an arousing sight; Kate, my proud and sadistic slut in her full naked beauty, looked amused while my sobbing slut Sam sucked on her cock. It reminded me of my fantasy of him sucking a pacifier.

Sam put a considerable amount of lube onto the tool. I laid my upper body comfortably on the bed and spread my legs wide so that Sam could insert his cock easily into my cunt. I ordered Kate to fuck Sam with the strap-on and had to remind her to slow down a few times. Of course, she didn't care much about Sam, but after a while, she fucked his ass at a steady pace, and with each thrust, he pushed his cock into my pussy.

I controlled them both. Sam wasn't allowed to move autonomously; his job was to match Kate's fucking thrusts and to fuck me, like she fucked him. I dictated the pace and felt Sam's sweating body behind me while inhaling the gorgeous Kate's scent. She had trouble going slower as I directed but tried to fulfill my wishes. Ultimately, I increased the speed, started a countdown from twenty to zero, and we all orgasmed simultaneously. It was such a rush.

I ensured both were well and Kate hadn't hurt Sam. It was also a fun challenge for me, and I enjoyed engaging with my beautiful slaves. My mind raced with so many new and creative ideas for future activities I thought my head would explode. Life couldn't be better.