The Babysitter

On her next babysitting job for me, with the children upstairs, she grabbed my ass while greeting me, and I got instantly erect.

"See you later, sweetie!" She said with a seductive smile, closing the door behind me.

This time, I wasn't late. I arrived home as expected, and Beth looked pleased. She slowly walked over to me and whispered, her breath hot on my neck. "Let's go to your bedroom." She led, and I followed. She locked the door in case one of the children woke and came looking for me. "We don't want them accidentally walking in, do we?" She said in a soft, sultry voice.

I stood against a wall, observing her. Beth sat down on the bed. "Over here. Now. I have a gift for you." I stood before her as she stripped off my pants and shorts. Naturally, my manhood hardened in anticipation of what she had planned.

She reached into a bag she had carried in with her and produced a metal object that looked like it was made of iron. There was a big ring with a padlock on one side with a hinge on the other. It was firmly connected to a smaller tube. The tube was opened on top and ended with a small hole. She let it dangle on one finger while showing it to me.

I had seen such things on the internet. It was a chastity cage for men. The penis is placed into the tube, and the big ring is closed tightly around the scrotum to prevent movement. The penis tube was formed in a downward curve, so erection is impossible when closed and locked. I knew of these devices theoretically but never even considered wearing something like that myself. I had always believed chastity was a choice and practiced without needing equipment.

"It's a chastity device," she said smugly. "Do you know why you earned it?" She answered her question before I had the chance. "Think what you were doing in your bed a few days ago. You came without permission," she admonished. "The time it takes to learn to obey is all up to you, little boy."

I blushed. Why was I allowing her to humiliate me like this? Why didn't I end this and throw her out of the house?

"I can't force you to wear it, of course," she taunted, "but you like my games, don't you? If you want me to continue your training, you have to prove that you trust me and willingly give your power over to me. Wearing this chastity device and letting me have the key is proof. What do you think? I should add that wearing this, well... I would find that incredibly hot!"

The answer to my previous questions was simple. I didn't throw her out because I loved these mind games she played.

The idea of forced chastity piqued my curiosity and turned me on. I had no idea what it meant to wear a cock cage. As I said, I hadn't been sexually active since my wife's passing, and equipment was never needed or an issue. It couldn't be any worse than the self-denial Beth wretchedly shamed me into with her text messages.

"Yes," I said almost in a whisper.

"I'm so glad to hear that, little boy," she purred. "Can you make your cock soft for me?" Beth asked, making me feel like a child with her tone of voice.

I shook my head, unable to speak. How was I supposed to do that with this incredibly hot woman sitting before me?

She shook her head and rolled her eyes in exasperation. "Of course, you can, little boy! Masturbate!" She ordered.

I had never been asked to rub one out in front of a woman before. Okay, the jerking off in the bedroom didn't count. It was a hot fantasy, and I had no idea she could hear me.

I start stroking myself reluctantly.

"Don't think I'll give you a hand job if you can't properly do it yourself," she chastised. "Stroke faster!" she commanded. I complied, deeply embarrassed.

"That's it. Now massage your balls with the other hand." I could hear the impatience in her voice. "Rub as fast you can, with a strong grip. It shouldn't take long, and remember, this isn't about getting yourself off for enjoyment; it's about making your cock soft."

Shortly after her last demand, I exploded in a massive orgasm.

"Finally!" Beth sighed in relief.

Indeed, my penis seemed reluctantly flaccid.

With a few quick movements, she installed the chastity belt. It felt tight and uncomfortable at first, but as she commented, smiling with satisfaction, it would fit well.

She kissed me passionately, and I immediately discovered how effectively the device worked as I began to get hard again. The tightness of the steel pushing against my cock aroused me, too, but my manhood soon filled the space. The tube's curve made it feel like my penis would break if it became more erect. Beth's kiss was sweet and painful, but she already knew that. I began to whimper softly, and she broke away from me.

"Thank you, Miss," I whispered with my head down submissively. Had I just thanked her because she stopped teasing me? I thought.

The next days

Wearing a chastity cage was a permanent turn-on. I couldn't forget it was there because the metal permanently teased my manhood. That led to even the slightest view or thought of anything sensual or erotic, causing an erection. The touch of the bare metal prompted immediate sexual thoughts to pop into my head most of the time. Eventually, it became an irritant that forced me to suppress tiny cries of pain. I managed to deal with it, but it was agony.

Everything set me off; seeing a female colleague's enticing lips bright with lipstick, a woman's stockings, the way women smiled at me or seeing how their breasts stretched the material of their shirts. Even if they wore long skirts or slacks, I tried to determine the shape of their legs covertly. I was permanently in dull pain, and the pain worked against my arousal. After a few days, it wasn't easy to function, and it took a tremendous mental effort to carry out my everyday tasks.

Beth made it worse by texting me lewd messages during the day. "I'm thinking of putting your big cock in my mouth. I can do it easily and suck you to unknown heights of pleasure." And, "I'm going to shower. Wanna join me? I'm going to have some fun with the massaging shower head!" Along with, "Can you imagine how hard I will make you cum if I release you from that restricting tool?" Yet another text, "When I close my eyes, I fantasize your tongue on my clit"

Soon I was conflicted between wearing the device with pride and profoundly regretting my decision to allow her to put it on me. As the days wore on, it was regret that won out.

A visit

While I worked from home, my children spent a few days visiting their cousins at my sister's. I was disturbed while working on a project by the doorbell. I got up to open it, and there was a stunningly beautiful blonde woman in front of me. She brushed by like she owned the place, and I was too surprised to protest. I closed the door, and she was suddenly invading my personal space. Feeling overwhelmed, I stepped back.

"Hi, my name is Kate," she said, "and I'm a friend of Beth's." I was stunned by her bold behavior. "She told me something hard to believe, yet I've never known Beth to lie about anything. I may be her slut, but I had to verify her story."

Kate came forward again; I stumbled backward until I felt a wall behind me. Kate leaned against me and grabbed my crotch with one hand. She could not miss feeling the metal of the chastity device.

"It's true!" Kate said, amazed. "She did put you in chastity! That is so hot! How could I have doubted her? I only hope she will forgive me for my distrust of her!"

She used one hand to grab me by my collar to pull me away from the wall while pushing me with her other hand flat against my chest. She forced me in the direction of the open door of the living room, and I had trouble maintaining my balance as I attempted to keep up with her.

Kate kept up her monologue. "Beth is such an incredibly hot woman. That she coerced you into doing this makes me so wet. I guess this is proof she can do anything she wants. Don't you agree? She is so convincing. Beth said I could do anything I wanted to you, even though she was pissed off at me for wanting to come here and prove she wasn't lying. Anyway, I know what I want to do with you."

Her eyes were shining at me with lust. She pushed me again, and I stumbled backwards into a sitting position on the couch.

Kate wasted no time getting down to business and quickly stripped herself naked. She was a beauty; her skin was tanned, her legs well formed and long, she was slender, her belly flat, and she had nice firm breasts that proudly defied gravity. Her ass was pretty sexy, too; not overly big but firm. A slim, sporty, and female form. A total bombshell.

I was still totally shocked by her actions. Despite being aroused by her exceptional beauty, I felt a tingle of fear in anticipation of what was to follow.

She placed her knees on either side of my body and began riding the cage with her crotch like she would ride sluttishly on a cock.

"Oh, fuck! This massive hard metal is making me crazy hot," she moaned.

Slowly I sensed the wetness of her cunt soaking through the fabric of my pants.

Her movements become faster and faster. She slid up and down over the iron cage and began to pant rhythmically. I was on fire and in pain simultaneously, but it was an incredible turn-on. I only regretted that she could ride the device instead of me. I was brought out of my misery by the pain in my crotch. I got harder than I thought would be possible wearing the cage.

Kate steadied herself with her hands firmly planted on my shoulders while increasing her speed and force at the same time.

"You can't cum no matter what I do, but I can feel your arousal and pain," she smiled sadistically. "I can do whatever I want to you. I... I..." and with a yell, she came. My pants were soaked wet with her fluids. She broke into an uncontrollable fit of laughter, making me feel more degraded and humiliated than I already was.

After she got over it, she managed to speak. "That was marvelous. Thank you."

She stood up, dressed and left, leaving me bewildered and immobile on the couch. Finally, I pulled myself together and needed to find a way to suppress my painful arousal. I made my way up to the bathroom and took a cold shower. That helped for the moment - at least as long I felt cold. Sadly, the release of the pain was only temporary, but there was nothing else I could do.

Soon my cock filled the cage again as I allowed my imagination to override my logical brain center. I recalled the hot blonde Kate riding me, which led to lewd fantasies.

A threesome

Beth scheduled another date, when my children would be away visiting their aunt and cousins, to remove the chastity belt... eventually. She said she wanted to see if I had learned to behave myself.

Beth and Kate entered the house when I opened the door to their knock. Once inside, Beth ordered Kate to strip, and Kate obeyed while making a sexy performance out of the task, which started a whole new episode of pain in my groin.

Beth then stripped, and while watching, I admired her defined, athletic body. She strolled to Kate, reaching over to finger her clit and cunt while kissing her. Kate became instantly aroused.

"You like this, don't you slut?" Beth teased Kate. "Show me that you're a good slut. Put on a good show for him; I want my little boy to see how much in heat you are." Beth coaxed.

Kate was visibly on the verge of an orgasm. Instead of making her cum, Beth grabbed Kate's hair roughly, pulling her down to her knees in front of her slit.

"Now it's time for my pleasure," Beth growled at the trapped woman.

Kate squeaked in protest. "No! I was so close! You can't! You can't!" Kate cried out in frustration. "Oh you can, but it isn't fair!"

Beth ignored her. "Lick me and make it good slut. You know I'm not nice to sluts when they disobey, especially when they don't do a good job."

Kate put all her energy into licking Beth, ensuring she enjoyed the effort, and Beth was soon on edge.

"Make me cum slut," Beth ordered, looking into her eyes. Seconds later, Beth shivered and moaned in her orgasm. "Good slut! You performed very well." Beth commended Kate while trying to catch her breath.

Still a little breathless, Beth managed to speak. "Now to the main attraction! I will remove the chastity belt so we can have a little contest. Kate, you must try and make Sam cum while Sam, you must resist orgasm as long as you can. Whoever succeeds wins and will be rewarded."

Beth stripped me naked, finally opened the padlock, and pulled the tube from my cock. She needed to exert force because my member had already popped up into a boner.

Kate decided to aggravate the situation by stimulating my imagination while licking her full cherry-red lips, "Sam, do you remember when I rode you when I came to visit? You don't stand a chance against your fantasies, Sam - or me! Let the games begin!"

It seemed impossible that my erection could get harder, but that is precisely what happened. Kate giggled as she took notice. It wasn't fair, but what the hell is fair in this situation? I knew she was right that I didn't stand a chance against either, but I was willing to do my best to resist and think of mundane things. Only a miracle could save me.

Kate came over and expertly began her duties, her confidence and expertise evident. She found fun in blowing some air over my rod, making it twitch into craving an orgasm. That was the last thing I wanted, considering Beth's forbidding it.

Kate continued her ministrations to my penis, licking me and sliding her wet mouth up and down my organ. I was close several times, but I managed not to shoot my load. I had no idea how much more of the cage I could take. The prospect of more time locked in it was enough to force me to keep control of my body and my thoughts.

Kate was able to put my whole cock into her mouth. The way she made it so easy and natural for herself only served to arouse me further. I hoped she would make gagging sounds which would be distracting. Instead of that, however, I heard her soft giggle while sucking me.

After a while, she stopped. Surprised, I looked at her; that was a mistake as I met her sparkling eyes. She licked her lips in the thrill of anticipation, totally confident that she would win and force me to orgasm. I lost all hope, convinced I would be condemned to continue wearing the damned device.

"Now to the finale!" Beth laughed and continued her directions to Kate. This time, I was sure I could not resist. From Kate's stimulation of me, it got to the point that not even the thought of getting back into chastity bothered me. The only thing that mattered was my need to cum so desperately. My whole body needed this now, and I didn't care about the consequences. I was getting closer and knew I couldn't avoid orgasm much longer.

"Kate! Stop!" Beth ordered, and Kate's mouth abandoned my cock. Kate loudly complained to Beth she had spoiled the game. "He was so close! You knew he couldn't resist and I would win! He had no chance!" Kate whined.

"I know," Beth sympathized. "You are a good slut. What do you think? Has Sam proven he has stamina?"

Kate considered the question for a moment. "Yes, he does. I never really believed he could hold on so long, but I still know I was on the way to winning," she said in the tone of a sulking child.

Beth chuckled, "I'm the referee, and I think you both won. He's only a man; he couldn't hold out forever."

"So, will I be rewarded?" Kate asked hopefully.

Beth placed herself in front of me. I still felt like I was on the edge. She pinched my nipples and laughed. "These are your slut buttons, and they're directly connected to your cock."

I looked at her, and she winked as she manipulated my nipples again. The aura of her dominance was overwhelming, and my phallus jerked like it had a life of its own. I watched as my semen spurted into the air. I moaned loud out of pain, lust and fear. Happily, finally, I was allowed to cum; not that I would have been able to stop it anyway.

Afterwards, Beth took care of Kate's and my needs. That was fun!

I was glad I passed Beth's test and no longer had to wear the restricting device. As my goddess, it was her right to demand it from me. I was willing to behave so that I would never have to wear it again unless, I have to admit, Beth commanded it.

The restaurant

Sometime later, Beth ordered me to invite her to a restaurant. I submissively obeyed, just as I would obey every wish or command she made to me.

We arrived and sat at a table near a private room, allowing us some distance from other guests. We ordered wine, main dishes and desserts. After the waitress brought the entrees, Beth texted someone on her cell. Minutes later, Kate arrived and just as hastily disappeared under the table, hidden by the long tablecloths.

Beth commanded me to eat while below, Kate unfastened the button on my pants, opened the zipper and sucked my hardening cock into her ready, eager mouth. There were not many other guests in the restaurant, but Beth demanded I act completely normal. I shivered from Kate's attention under the table and accidentally let my fork drop onto the plate while Beth ate, conversing with me as if nothing unusual was happening. Small soft whimpers from Kate told me that Beth was somehow tending to her under the table.

Beth was thoroughly enjoying the situation. It didn't take long before I was on the verge of an orgasm. Kate had been ordered not to allow me to cum but repeatedly brought me close to it. It became increasingly difficult to eat and act like an average diner.

During dessert, Kate brought me to the edge again. Curiously and with delight, Beth watched me. She slowly dipped one finger into the whipped cream of her dessert while I watched in anticipation of what she had in mind.

"Lick my finger," she ordered.

I obediently licked it like it was a cock. Beth aggressively inserted the digit deep into my mouth and held it there as she ordered in a seductive whisper, "Cum."

She timed it well, as I was just about there. I wanted to clench my teeth while I came, but I couldn't without risking biting into her finger. So I concentrated on relaxing my mouth while Kate gulped every drop of my semen like the submissive slut she was.

"Good boy," Beth praised me. I was in heaven for having received her approval; at the same time, I was drained.

Kneeling on the floor

That was only one of the scenes I experienced with my babysitter/mistress. I had never considered being submissive before. Do I love Beth? I've thought about that, and I admit, at this point, I don't. I am drawn to her, though, like no one since my late wife. I enjoy every second with her, her incredible sexuality and creative mind.

Once more, my children are with my sister, and I am alone, kneeling on the floor, waiting for my goddess. I don't know what will happen, but I'm sure whatever it is, she will bring me to a new level of raw sexual excitement. Like a drug addict waiting nervously and hungrily for his next fix, I know I cannot stop now; I can only go deeper and deeper into submission with her, and I can't wait for the next adventure.