(This story is completely fictional. I wrote it just for fun so the events and characters in this story are not real.)
**[Part 1] (https://www.reddit.com/r/Erotica/comments/yucllv/fictionalf26m26fpovchastity_becoming_a_keyholder/)** / **[Part 2](https://www.reddit.com/r/Erotica/comments/yucmm4/fictionalf26m26fpovchastity_becoming_a_keyholder/)**
This part of the story takes place around a month after my last entry. The reason for skipping ahead is because the weeks that followed were fairly similar to what had previously happened and there is no need to repeat myself, though I’ll give you a rundown of what happened.
Owen was in chastity again for a week. In identical fashion, it was a Friday to Friday wait for him in his cage while being able to look at whatever lewd and/or pornographic content he liked and we chatted on a near daily basis to maintain flow and connection with each other. I was still sending him selfies and daily outfits, the compliments from him still overflowing with flattery and underlying desperation for release, which brought a devilish smile to my face. Of course, when Friday rolled around he had earned his freedom and we would meet and I would provide him with the key for him to trot off to his room by himself and relieve himself of his backed up week’s worth. He’d then return to me to confirm his re-locking and we’d wait another week.
You can see how repetitive this was over the next 30 or so days so it was easier to just summarise it. Don’t get me wrong however, it wasn’t repetitive or dull for us. We were both having a fantastic time! For me, it was an amazing self discovery of a new kink and exploring it both with Owen and online had opened up a whole new world to me and for Owen, he had what he had always wanted, which was a keyholder. He was persistent to remind me how thankful he was and how much he was enjoying the week’s wait each time. We became each other’s obsession and a message from the other was never long left unread or responded to.
Anyway, you’re probably wondering what was the next big step or did it just continue like this or even what’s this post about? Well let’s get into that! I let Owen celebrate the month together (the 4th week of weekly chastity) with a whole 30 minutes instead of the usual 15 minutes I gave him, which he used around 20 minutes or so of. The reason for doubling his allowed time was because we had discussed what the next time length would be and it would be quite the increase in waiting. A whole month. 31 days of locked frustration and denial. So you can understand why I let him enjoy himself a little longer than usual before his big imprisonment.
“Are you nervous?” I asked him as he placed my necklace, with his key still attached to it, back into my hand. His cock now locked for the month ahead.
“Yeah.” He nervously chuckled. “I’ve never done that long before but I am excited to see if I can do it.”
“Just keep being good and you’ll be fine.”
The exchange went a little like that and it was a pretty big deal for us. A big jump in time, dedication and passion for us. We had discussed the original rules we laid out before and decided to change them slightly to relate from the jump to a month from a week. The rules for the month were akin to the previous rules for when he was in chastity for a week, though they had changed slightly.
1. Chastity would last a month instead of a week.
2. The rule stating either of us could end the chastity at any time and the keys would return to Owen, **remained the same** as we still very much cared for each other and took consent and enjoyment very seriously. So that rule was unaffected.
3. There was no longer a necessity to talk everyday as we were more comfortable with the setting, though we would go on to talk nearly every day anyway.
4. For the lewd/pornographic content consumption, I gave Owen the choice. He could either look at porn for the first 2 weeks or the last 2 weeks of the month. He chose the first 2 weeks. After that, he wasn’t supposed to look at anything lewd and/or pornographic. (I had no way of actively monitoring what he was looking at nor would I even if I could. I understand it’s possible he looked at it anyway, but there was a built trust between us and I trusted him to conform and even now I believe he did so.)
We still met every weekend, either on Friday or Saturday, just to keep up tradition and to spend time with one another. Instead of going to Owen’s apartment (as we normally would for his release) we would go for a coffee or take a walk together. Something outdoorsy or more public. They were cute little dates and something for us both to look forward to throughout the week and they were always a good time. Though Owen would feel the strain a little more each time as the weeks passed because I always made sure to wear the key necklace and have it on show around him. A very simple reminder that I owned his orgasm privilege and there was more waiting to be done before the end of the month.
For the first few weeks, Owen had done surprisingly well, at least from my perspective. He didn’t really show any cracks of pressure or signs of wanting to give up on the month. He was… Just Owen. Naturally he was still flirty and complimentative towards me, but not much on top of that until the last week of the month. It was around this time that he mentioned to me he couldn’t wait for Friday (release day) and it was starting to itch at him. I questioned him a little just to further tease and see how deep he was in his hormonal torment.
“I just really need to jerk off haha I have to stop myself from touching because I just strain against the cage. Don’t worry, I’m not looking at porn even though I want to so badly and I can definitely wait it out till Friday.” His message read a little like that.
Obviously, this message had me grinning like mad. His loyalty and service to me was undeniable and unbreakable. I was a lucky Mistress to have such a devoted sub who I could trust wholeheartedly and trusted me the same. So what was my gut instinct at this point to reward such duty? Give him a few days off of his month for being so good? Hell no, he was so close and he said he could wait! As a substitute I upped the ante just a little bit with my selfies to him. The next time I had a shower, I took a headshot of myself with the camera just stopping before my boobs. So it was bare face and bare shoulders with wet hair fresh out of the shower, how lewd I know! Although probably not the sexiest photo one could receive, it was the most skin I had shown him thus far and I can imagine when you are just over 3 weeks without orgasm, that sort of imagery is salacious.
“Oh my… You’re so beautiful Mistress. I’m going to have to try and not look at this too much haha.” He responded. Such a commendation. He couldn’t stroke his cock so he stroked my ego instead, I allowed it while biting my lip knowing the effect I had on him.
Throughout the remainder of the week, I’d send him similarly vain selfies. Nothing too exploit or lewd, but always something for him to gawk at such as my shoulders or legs if I was wearing shorts. I am sure he was counting the minutes, maybe even seconds till Friday night. With the passage of time, Friday night did come indeed and we met in our routine fashion outside so we could walk together back to his place. As you can imagine, Owen was in very high spirits straight upon meeting. His hug to me was tight and his smile was ever present as we walked back to his apartment. He explained on the walk that he had already had a really good day at work and the day had flown by, since he was worried today would feel like the longest day of his life. I giggled and smiled at the appropriate times, it was cute he was so elated and with what I had planned, he would not be disappointed.
Entering his consistent looking apartment, we dined, drank a little and socialised our usual amount and as the evening beckoned, Owen’s anxiety was filling the room as he waited for when would be the time I handed over the key, his foot tapped a lot or in a specific rhythm when he was anxious and learning this helped me know how much longer I could make him wait or not at all depending on my mood. Nevertheless, I didn’t keep him waiting too long once I spotted his eagerness and stood up unannounced, his eyes instantly fixated on me and joined me in standing. I walked over to him and I could almost see his hand lifting to accept the key. Instead, I spoke. “Get naked. Either here or in another room and come back. Get some towels and tissues as well.”
Owen rightfully looked confused as this was a curveball he did not expect. His lips went to speak, but a flick of my eyebrow towards the hallway was enough to stop him and he did just as I asked. At the beginning of this journey, I mentioned a big hurdle for us doing this was seeing Owen’s penis, we were just friends after all, but after the various weeks I had grown accustomed to seeing and inspecting it. I had never seen it hard though, semi grown at most so his naked form no longer bothered me. After a few minutes of Owen going back and forth, there were now 3 towels laid out on the living room space following my directions (we moved some of the seats and coffee table to make room) and Owen was now naked standing on the edge of this line of towels, still locked in his cage. The TV was now off so silence lay around us as I did a few final surveying before continuing. While he was organising the room, I had pulled out a box of clear disposable rubber gloves from my handbag and placed them on the table. I then put on a pair of these gloves, they were skin tight with very little looseness. Just how I wanted them.
I kneeled down onto the towels, Owen sharply inhaling with his mind clearly going to the naughtiest places. His locked shaft was now in front of my face and I brought up the key from my necklace and unlocked him. He let out an exhale of relief realising he would be allowed release today but I held the cage in place as I went on to speak.
“I want your hands behind your back at all times. I do not want any cum to touch or land on me. If any of your cum lands on me, you will go back in your cage for a very long time. If you must cum, you are to aim it away from me at all costs. Understood?” I spoke with power and strictly.
“Yes Mistress.” he responded after a gulp at my authority. I also had him repeat what I had asked. No cum to land on me and his hands went behind his back.
I nodded acknowledging his agreement and removed his cage to notice it was already semi hard. I heard another exhale from him, though my eyes were on his cock. I casually looked it up and down, not for any real reason besides my own curiosity. It was a nice penis and I mentioned to him before that I wanted him to keep the clean look so he regularly shaved it and it was clear he had shaved it earlier today. After a few moments of my gawking, I slowly lifted my right hand and with the outside of my index finger, I ever so gently began to stroke the underside of his shaft with it. His cock instinctively twitched at the foreign touch and I sustained the slow back and forth of my finger making sure to reach the bottom and top with each rub. I did this till he was fully hard, which didn’t take long, and uncontrollably I did my usual tell of biting my lip at it. It was quite attractive and knowing I had control over it drove my mind wild.
During this stage, my goal was to lightly tease and touch around his cock. I rubbed with the outside of my fingers under his shaft and poked and stroked at his frenulum, eventually giving way to some soft moans from Owen though I can tell he was trying to be quiet while I worked. I occasionally would glance up with a smile at him but most of the time my attention was directly ahead of me. Obviously, the gloves were numbing some of the usual skin to skin sensation one would experience here and that was on purpose to ensure he didn’t finish too quickly though pre-cum had started to form at his tip.
I gingerly chuckled to myself seeing this erotic gleam and moved my face about an inch away from his tip, my eyes beamed up at him and my finger still stroking his frenulum. “I bet you’re dying for a blowjob right now… My wet, warm mouth… I’m sure if you felt the back of my throat you’d probably just cum instantly.” I whispered warmly and deeply up at him.
“Mistress…” Is all he could muster back at me as he looked up at the ceiling for some assistance to hold on.
I giggled again. “Or even if I just stroked you hard and fast, you’d erupt all over me. Covering me in your hot cum.” My finger wiggled quickly against his tip before he quickly pulled away from me and took a step to the side. He moaned in angst as he was clearly trying to hold his orgasm in but wasn’t sure if he would cum or not. He didn’t in the end, succeeding in his attempt before returning in front of me a few moments later, his hands still behind his back. I asked if he was ready to continue and he nodded.
I returned to my light hand work of teasing and light strokes with the outer parts of my hand and fingers, still sometimes using the pads of my fingertips to rub around his tip. The gloves themselves were now wet with precum where I used them most, creating a slipperier surface for his penis to glide on, making my job a little easier. I unceasingly teased him with further lines of dialogue as this went on. I told him to picture his favourite selfies I had sent him, what I looked like in the shower, how my body would feel against his. I realised as well since I was kneeling below him and the fact I usually wore lower cut shirts in his presence and today was no different, he had a good sight of my cleavage and I vocally gave him permission to stare at my tits. I explained how soft and squishy they were and if he kept being this good, maybe one day I would let him touch and play with them. All this taunting and tormenting made Owen’s toes curl and unfurl multiple times, his cock twitched and heaved with lust and he was either moaning, gasping in an attempt to hold in his orgasm or whispering ‘Mistress… Goddess…’
By this point, his penis was red and swollen from ever growing frustration. I’d never actually seen a penis get this agitated before, thick and bulbous was his tip dripping with precum and his shaft never softening even slightly. Owen mentioned with a fair amount of desperation that he was close and it would be soon. I guess he did this not so much out of the outlook of pleasure, but more because I was in the firing line and he did not want to risk a longer chastity sentence. I thought in that brief second whether or not I wanted to test his limits and remain in front of him, but in the end accepted I did not know the man’s limits yet and as much as I didn’t mind cum for the most part, I didn’t want to get blasted with jizz and enforce my ruling because I had miscalculated.
I decided to move for the first time since this started. I remained knelt but instead, moved to his left side so I could still be close but not in the splash zone. I ordered him to look at my chest, even pointing towards the top of my cleavage. He still had a good downwards angle to look at them and he had no reason to look at his penis, that was my concern. I then removed my right hand glove to reveal my nude hand (how scandalous!) Although I did not entirely plan on doing this, I was in the mood so I brought my right hand up to under his shaft and stroked in the same way as before (with the outside of my index finger) but a little faster this time. Owen moaned instantly at this development and it wasn’t long till I noticed he had gently started to rock his penis across my finger. The pre cum drooling out of his inflated tip landed on my finger and that created a lovely, silky platform for his frenulum to ride and it wasn’t long before I simply was just holding my finger in place as he thrusted against it.
“Ohh Mistress… Mistress.. Goddess… I’m cumming, I’m cumming, I’m cumming! Oh god, Mistre..!!” Was what Owen moaned into the room as his thrusts and breaths got deeper and it wasn’t too long before he achieved his month long wait.
I didn’t count at the time, but it was at least 4 ropes of cum that shot out of his throbbing cock all across the laid out towels. There was even more cum that dribbled out after the initial shots. It was the most cum I had ever seen in my life and without even knowing it, my left hand was between my legs lightly rubbing and my eyes could not leave the sight of his ejaculation. Owen moaned, groaned and his pleading turned to thankings as he finished himself against my finger. My last motions against him was to do a final squeeze against his tip, causing another dribble of warmth to slide down past my fingers and my still gloved left hand firmly squeezed his testicles to ensure they were empty. They were sure a lot emptier now than when they first looked.
After I was satisfied with the way he had been released I retracted both my hands from him. I know I sort of broke my own rule of allowing his cum to touch my bare skin after telling him not to get cum on me, but I allowed this small oversight for the sake of our enjoyment. My bare right hand sticky with the mix of cum and pre cum acting like thin webbed string between my fingers, which I calmly wiped off on the closest edge of a towel as Owen slowly came round post orgasm. His breath was still deep and heavy as I stood up and as I stood, I felt how sodden my own underwear had become. I hadn’t orgasmed that was clear, but I had worked myself up more than I thought and as I stepped around the living area, it was so apparent to myself that I had also thoroughly enjoyed this session.
“Thank you Mistress..” Owen smiled at me as he used a towel to clean a little more of himself up. “Please can I wait another month if we do that again?”
I told him I’d think about it as we cleaned up. Together (mostly Owen touching his cummy towels) we cleaned the living space up and recovered it to its original state and it came to the point where Owen needed to be locked up again. As usual, he locked it and I inspected it, as I observed to make sure it was locked to my liking, I thought about his request. It would mean another night like this was a whole month anyway, but this one was very much worth it and I hadn’t really given much thought on how long his next cycle would be. So I simply responded with a final tug on his cage.
“I’ll let you know.”
(Hope you enjoyed this part! So glad to see lots of you are enjoying my little stories with these 2! Any feedback, criticism or comments are welcome below or in DMs!)
Source: reddit.com/r/Erotica/comments/yuz3ag/fictionalf26m26fpovchastity_becoming_a_keyholder
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