Headline
Message text
In the proceeding days I did become more accustomed to wearing a dress in the office. Although, I'm not sure if I'll ever be fully comfortable.
I even used the ladies room. Joanne, bless her adventurous spirit, coaxed me in by insisting we 'freshen up' before lunch. She made the oddest thing feel perfectly natural.
Yet, even as I was fully engrossed in femininity, Karen continued to deny me a place in her bed for fear of my little vestige of manhood popping out. Meanwhile, she still ordered me not to play with myself.
I was denied my reward for emasculation, and still unable to get release. By Friday evening, I was a bit stir crazy. Per usual, I had given her an orgasm with my dutiful oral service. However, my cock strained from its tucked position, untouched.
As she sent me to my bedroom, I practically whimpered in despair. This only served to convince her that she was right to deny me bedroom access.
Laying in bed, the panties rubbed against my penis. At last released from its tucked position, I reached a full erection, such as it is.
I rested my hand on my inner thigh, delightfully rubbing the smooth skin. This technically wasn't breaking the rules. Although, I knew I was being bad. 'Stop it!' I chastised myself. Yet, I didn't stop caressing my inner thighs.
My wrist brushed against my penis, sending a jolt of excitement throughout my body. Oh goddess, it had been so long. The silk panties only heightened the sensation.
'Stop it Christine! Touching yourself is not permitted. You'll be punished for this!'
I continued to caress my thighs, with my wrist 'accidentally' rubbing my little penis. I wasn't touching myself. I wasn't breaking the rules.
My stroking intensified. My hand reaching higher, closer and closer.
Then my hand cupped my balls, pressing against the sensitive skin at the base of my cock. I muffled a moan, fearing that I would be heard. There was no denying my disobedience now.
Once the Rubicon had been crossed, I reached into my panties, and wrapped my hand around my penis. Even in my dainty hand, it was small.
I began to stroke it in earnest. I learned my head to the side, biting a pillow, doing anything to stop from moaning. I prayed that my movements weren't creating any creaking or rustling noise from the bed.
In my desperate state it wasn't long before my body tensed, and quivered.
Knowing this was wrong only fed my excitement. Before I could stop myself, I was shooting my load over my stomach, staining the panties, and the hem of my night slip.
I glanced down in shame and humiliation. My cum quickly becoming cold and sticky. Not only had I disobeyed her, but I only had this pathetic dribble to show for it. I had relief, but no pleasure.
Reluctantly, I stood up, and made my way to the washroom as quietly as possible. There was no noise from Karen's room, so I prayed that I hadn't awakened her. Once safely inside, I removed my slip and panties.
I wanted to take a shower to wash my sins away, literally and figuratively. Yet, I knew that would definitely wake Karen. I settled for a wet towel.
Once I was clean, I turned my attention to the soiled panties and slip. The stains were clearly visible. Fortunately, I reasoned, I did the laundry. There was no reason for Karen to know anything about this. It sounded reasonable in theory, but instinctively I knew I was only deluding myself. Nevertheless, I gave them a quick wash in the sink. At the very least, I needed to ensure the stains could be removed at some future point.
Naked, I creeped back across the hall into my room. I placed my dirty undergarments at the bottom of the laundry hamper, hiding them from the naked eye.
I settled into bed, and with time was able to drift into restless sleep.
* * *
The next morning I was on edge. True, my frustration and blue balls were relieved. Yet, those feelings had been replaced with guilt, and a fear of Karen discovering my deceit. I was supposed to have blue balls.
I washed up, dressed, and made my way down to the kitchen. I hoped my usual routine would mask my shame.
Per usual for a Saturday, Karen was enjoying her morning swim. And like always, she was a true vision of beauty when she entered the kitchen wearing only her bikini. Yet, rather than taking in the view of this goddess, I shifted awkwardly.
She sensed something amiss, but let it go. She went upstairs to change, leaving me to prepare breakfast.
We ate in relative silence, once again out of character.
With some chores to do, and not much to do that day, I thought I had escaped Karen's scrutiny. Yet, as I was washing the dishes, Karen reached under my dress, and grabbed my penis. I gasped in shock, nearly dropping my dish. What I didn't do was stiffen.
"I knew it! You cheated, didn't you?! You played with your little dickie without permission!"
I looked at her, prepared to deny it. "I'm sorry," I muttered, looking down.
She still held my dick, gripping it in a menacing fashion. Her eyes were equally fierce.
Eventually she released me, and backed away. "What am I going to do with you?"
"I'm sorry, I didn't mean to."
That only angered her further. "Didn't mean to! How do you rub yourself accidentally?" She shook her head dismissively.
I stood motionless, still averting my eyes. I didn't answer her. What could I say?
She walked out of the room, and up the stairs. For a moment, I thought I might have a reprieve. Not forgiveness exactly, but perhaps an acceptance that I was only human. A male human, and this was only natural.
This hope disappeared when Karen reappeared with a wooden hair brush. The manner in which she patted the palm of her hand with the brush left little doubt as to its intended use.
I hastily rinsed the plate in my hand, and turned to face her. The brush terrifying me.
" I didn't want our day to start like this. And I'm not sure if this will even correct your behavior. But you must understand that disobedience has consequences."
Part of me wanted to plead for forgiveness, and to promise I wouldn't do it again. Yet, I knew that this would only inflame her anger. So, I did not utter any resistance.
She led me by the hand to her chair in the living room like I was a recalcitrant child. She sat down, and patted her lap. Although she had only spanked me once before, it was a signal I was all too familiar with. I obediently bent over her lap.
She raised my dress to expose my behind. "I truly don't like having to punish you like this. But you need to understand that I decide when you may or may not cum. And to think, you wanted a place in my bed! Imagine, having you lying next to me with your little thing twitching excitedly. Disgusting!"
She rubbed the brush along my bare skin, eliciting excitement and terror. "I think 25 is a good number."
The first blow landed, and I yelped in surprise. The wooden brush had some real force, reddening my behind immediately.
"I'm doing this for your own good. So, I better hear some thank you."
"Yes, thank you."
A second blow landed. "Is that how you address me?" The third blow immediately followed.
I gasped in pain. "Sorry mistress. Thank you mistress."
"That's better." A fourth blow landed.
"Thank you mistress."
"I want you to count them, and thank me for each strike."
The next blow landed.
"Five. Thank you mistress."
"Five? Are you sure? It seems like someone is trying to get out of the full punishment they deserve."
"No mistress, I swear!"
"Ok then. Do you stand by the number 5, or should I start over, just to be certain?"
I understood the trap. She is so smart. I could stand by my rational thinking, or I could trust that a woman knows best. For me, there was no choice. And as I was coming to understand, there never really was.
"Please start over mistress. You know what's best."
Bent over, facing the floor, there was no way to be certain. Yet, I could swear that she smiled.
The brush struck once more.
"One, thank you mistress."
Blow after blow. Unrelenting. "2, 3, 4, 5... Thank you mistress." I was a blubbering mess by the end. Tears streaming down my face.
I knelt before her once it was over. I rubbed my aching backside. She presented the brush before me, and I dutifully kissed it.
"Good boy. I hope that's the end of that behaviour."
Her tone suggested that she didn't think it was.
For the rest of the day we forgot about it. She met up with a friend for coffee, while I did the grocery shopping, and some other errands.
Perhaps I thought all was forgiven when she allowed me to service her that evening. Yet it was clear that night, when we went to our separate bedrooms, that she still did not trust me.
I didn't dare touch myself this time. My ass still ached from the punishment I received. Yet, more than that, I was ashamed and lonely. I had to find a way to earn Karen's trust.
My sleep was rather fitful that night. However, I awoke with a sudden resolve. I knew how to earn my mistress' trust. Although, I was not looking forward to this solution.
I must have appeared on edge that morning. Or perhaps she was simply establishing a new routine. For whatever reason, she reached under my dress and stroked my panty-bound penis.
This time, my little appendage jerked up to attention, and I moaned. The desired result. A sissy desperate for release.
She slowly caressed my sissy clit, eliciting more moans. My legs shivered, but I dared not move.
The immense pleasure was torture. I knew she would not bring me to release. Likewise, I knew her touch was not a reward, but a test of my loyalty. My only saving grace was that I passed.
When she pulled her hand back, I whimpered in despair. I had to resist the temptation to stroke myself over that edge. I turned to look at her with pleading eyes.
She stroked my hair. "Good boy, good boy."
I continued to plead with my eyes, but said nothing. Don't good boys get rewarded?
She walked out of the kitchen, satisfied that yesterday's 'correction' still had effect.
The remainder of the day was somewhat routine. We did have some time to enjoy a local festival, for a couple hours. It was still somewhat unnerving to be fully feminized in a crowd of people, but I quickly adjusted. It was endearing to see Karen delighting in the simple things: street music, hot dogs, and children running around with face painting. As ever, she was a goddess strolling amongst the people.
My nervous energy returned that night. She stretched out on the sofa watching a documentary. I knelt obediently at her side. As per her habit, she occasionally stroked my hair like a beloved pet, but otherwise ignored me.
I could barely concentrate on the program. My thoughts were consumed by that night. She would once again dismiss me to my separate bedroom, and I would once more be frustrated and alone.
My earlier resolve returned. There was no other way. Without a word, I got up, and went to my bedroom. I knew where to find what I was looking for amongst the boxes I had moved from my place.
I found it along with the note from my mother. It had been snuck in with my things when I left home. I had often wondered why I never threw it out. I suppose part of me believed this was inevitable. I hadn't read the note in years, but I practically had it memorized.
"Dear Christine" (Oh, how I had hated when she called me that).
"I am still holding out hope that you will find the right woman. You will know you found her when she holds the key.
Love, Mother."
I walked back downstairs, and knelt before Karen, facing her. I only did that when I wanted her attention.
She scrutinized me for a moment. Her attention being drawn away from her program. She wasn't annoyed, but curious.
"What's up Christine?" She glanced at the box in my hands.
I averted my eyes, doing my best to keep my nerve. "Karen... Mistress... I know you have your doubts about me controlling myself. I understand. Truly, I do. Chastity is one of the principles for a Familiar in my mother's faith."
I paused to regain my nerve. I was a Familiar, despite my years of denial. My Goddess deserved nothing less.
"Perhaps I am too weak to control myself. Yet, I can give you control." I opened up the box, and raised it for her to see its contents.
She looked in the box, and then at me, questioning. She knew what it was, although I doubt she had ever seen one before. Had I presented this before now, she may have doubted my intentions. She picked it up and held it in the palm of her hand. She noticed how small the metal cage was.
"Are you sure?"
I was far from certain. Yet, I had given this a great deal of thought. How do I explain that this is more than a kinky fetish? Indeed, I was not relishing this. Yet, it had to be done.
I remembered the letter, and handed it to Karen. She read it slowly, absorbing its full meaning. Then, she looked at me. The device still rested in her open palm.
"You do love me, don't you?" It was more of a statement than a question.
I had a broad smile on my face. "More than anything."
She gently brushed my cheek. "I love you too sweetie. So, I guess that makes me the 'right woman'."
She looked at the chastity device and chuckled. "You know, I don't know how this goes on, or how it works."
I looked at her with a sheepish nod. "Don't worry, I do."
She laughed. "Oh Christine. Your mother trained you so well."
For so long, that would have been insulting, but now I saw it for what it was, a compliment. I stood up, and motioned to raise the hem of my dress. "May I?"
She nodded.
I proceeded to lift my dress, and pull down my panties. Even now, I was ashamed to expose my small penis. Although, it now had the advantage of keeping me soft and ready for the cage.
I bent down to retrieve the lubricant I had set down next to the sofa and straightened to once more expose my limp penis. "I better apply the lube. This won't work if I have an erection."
Karen nodded. She had no interest in touching me.
I applied a generous amount of lubricant, but was careful not to overly stimulate myself. Touching myself directly in front of her added to my humiliation.
"Ok, now place the ring over my penis, and behind the testacles."
I deliberately avoided the use of vulgar terms or slang to instruct her. I suppose I could have done this myself. Yet, it somehow felt like a violation of the rules. A mistress cages her sissy.
Karen followed my direction. Her fingers barely touched me as she slid it on.
"Now place the cage over my penis. Make sure the hole lines up with the tip of my penis to avoid any future messes. You will find that it connects with the ring."
Once more, she followed my instructions. This time her hand did hold my penis. Just this tiny contact made my cock stiffen, and was already constrained by the cage. I remembered this discomfort. It had been years, but it's not the type of thing one forgets.
"Now the lock mistress."
She smiled as she locked it in place and put the keys into her small handbag.
"Thank you mistress." I pulled my panties back up, lowered the dress, and knelt back down. I bowed my head, and kissed her feet. Already my subjugation was arousing me, leading to pain as my member could not grow even to its meager stature.
"It seems like it's a rather open cage. Doesn't that allow you to still touch yourself?"
It was a fair question from someone who didn't understand the true sinister nature of chastity devices.
"Yes and no. This is a top quality one, designed for permanent use, and easy cleaning." There was no need to elaborate on this embarrassing, but entirely natural function. "I can still technically touch myself. However, if I start to get hard, my penis presses into the stainless steel and cannot grow. Plus, it is very painful. Likewise, the ring pulls tightly on my testacles."
"So touching yourself...?"
"Is like torture." The function was clear. Not only were erections impossible, but any form of sexual gratification only led to pain and suffering. "Some mistresses will stroke their sissy, or even just whisper erotic things to them, just to torment them."
Why did I tell her things that could only lead to more suffering? Fortunately, Karen didn't seem to enjoy tormenting me.
She stared at me, smiling. The circle was complete. The cage naturally enforced the third principle of Familiars, chastity. Yet, by giving her much greater control, and a simple means to discipline me using her womanly charm, my obedience was reinforced. And while I could always remove the dress, Karen held the keys to my manhood, emasculating me. Chastity, obedience and feminization. The three principles of every Familiar. Every sissy.
My excitement fed my pain. Fortunately, I could see that it excited her as well, and this led to my reward.
She led me to her bedroom. This time I wasn't dismissed. This time, there was no manhood to disturb the sanctity of this room. This time I was allowed to worship her properly.
She lay back with her legs wide spread, receiving my devotion. Each time my penis pressed painfully against the cage, I intensified my licking. It was her right to receive pleasure. It was her right to orgasm.
My only pleasure now was in serving her.
You need to log in so that our AI can start recommending suitable works that you will definitely like.
There are no comments yet - be the first to add one!
Add new comment