Chastity Keyholding Play Becoming Reality, Mistress F, Part 1

Mistress F, Keyholding Play Becoming Reality, Part 1

Preface: This is a real story, unfolding in real time, with personal details withheld, we are currently on Day 8, and this story will be updated to eventually reach the present day. User feedback, especially ideas both for pleasure and discipline, are strongly encouraged. We need ideas for enforcing staying locked and not breaking free, as no cage is full proof, and I’m pretty crafty to get a cage off if I wanted. Both the chaste and Mistress will be reading the comments. Mistress F notes that methods of punishment for if the chaste breaks free to pleasure himself are especially wanted.

Day 1.

For as long as I can remember, I’ve had a problem with chronic masturbation. Every time there was a twitch or even small urge in my dick, I’d pleasure myself whenever I was next alone. With the exception of a few relationships with various women over the years, my predominant way of cumming since I was a wee lad was from masturbation. This evolved over the years to incorporate edging, online porn, gooning, and in recent years I realized Reddit was an amazing platform for kinks. I can edge for hours, with a quick/average session having 5-10 edges, a longer hour long one maybe 20 or so edges, and if I have time and break out some toys(namely butt plugs, cock straps & ball straps, and I love having my balls tightly bound and stretched when I stroke. I once could only cum for a year or more if my balls were bound tightly with one specific elastic ring I that I rather like), I can edge for hours, with about 100 edges being my record. Porn, pot, coconut oil, and my headphones and I’m in heaven. I’ve hit 100 three-ish times, it’s really hard to know at that point, you’re so gooned out it’s difficult to keep track of the count and the time. There’s a chance I hit around 150 once, but honestly I don’t know, so I play it safe at 100, it was definitely 100, with lots of holding my edges too, like 2 minutes sometimes. I have amazing control with myself. I can say confidently that this turned into an addiction, and became a daily habit. When I edge to porn I’m mostly rock hard for hours, but I’m human and it’ll occasionally need a break then get hard again with relative ease for another round. Firm, gentle, and steady twisting strokes usually do the trick. As a result of this constant stroking and edging my dick, day after day, the keyholding, chastity, and femdom related forums started to dominate my interests. Because I have no will power to stop myself from jacking off, the fantasy of not having that option, of being forcefully/mechanically restrained from being able to jack off, or even the ability to touch yourself, has appealed to my kinky side.

I was single during most of this period, with an occasional hookup, but no relationships longer than a few weeks or months. I always preferred jacking off and edging to porn vs real women, they just couldn’t make me feel the way I could make me feel myself. I tried to get kinky with a few of them, but they weren’t into it. So I never really got to explore any of my kinks, other than pretty much vanilla sex and the occasional rough fuck.

But then I met the women of my dreams through work, and we lined up a date after she asked me out one day. I was too shy to ask her out, but was insanely attracted to her from the first time we met. She had red hair, an amazing figure, and dressed in a shabby sheik kind of way, usually wearing well fitting tops, high heals, and her tops generally had high shoulder frillies or shoulder pads, hinting she may have a dominant side. After working with her for about a year now, I’d noticed she had a commanding presence, and if she wasn’t a domme, she’d make one hell of one to some lucky subby one day. It’s hard to describe, but more than anything it’s the look in her eyes, they’re sexy, commanding, with gorgeous colors but you can see a bit of mischievousness in there, and when she gets mad her eyes get like sexy/evil which makes my cock twitch. We had dinner, it was amazing just to get to know her outside of work. We came back to my place afterwards, and if I wanted to I could have fucked her right then and there on my couch. I’d edged my brains out the days prior just thinking about the possibilities of dating my dream woman, and didn’t think I’d be able to get hard. Plus it had been over two years since I’d last had sex, I really had performance anxiety. So I cooled down the situation, she left an hour or so later, and I regretted having edged and cum so much the days prior. Over the next several months our relationship grew into something special, and after about six months or so we started exploring our kinky side, and I kept poking her to be more dominant with me. I’d slowed down a little month by month on how often I’d have an edging session, how long, using different lubes to break the pattern, etc, but the problem was still there, I just couldn’t kick it entirely. And I know it was having an effect on our lovemaking, I can make myself feel pretty damn amazing, and it’s a very different feeling for my dick receiving oral/vaginal/handjobs, so sometimes I just can’t feel it or the sensations/lube isn’t enough to keep my dick interested, and I lose my erections.

I’d occasionally break out the chastity cage, surprise her with it and hand her the keys. I was trying to top her from the bottom, get her to hold the keys and prevent me from masturbating. But she didn’t seem to be into it, she’d usually keep it on me a few hours then give me the keys, not really understanding what it is or what it’s for, it just looked painful and weird to her. But 8 days ago, well 8 days ago everything changed.

I spent the night at her house, and that night before bed we fucked pretty hard. I came before she did, and she was left frustrated that night, not having the orgasm she deserved. That morning we woke up, my cock was a little sore from the night before, and when she started working my cock over with her amazing mouth and later hands, pleasing me in ways only she knows how, making me feel things I can’t make myself feel(and I’d like to think I’m rather skilled at pleasuring myself. Like expert level), I wasn’t performing, I’d only get like semi hard. She was frustrated, and I offered her the chastity cage to keep my cock from me, and prevent me from jacking off. Much to my surprise, she enthusiastically said yes.

I ran out to my car, grabbed it from my backpack(again, I’m into it, I would always bring it on the offshoot chance she wanted to play). She held it in her hands, looked a it with a bewildered look even though she’s seen it before, and she started to put it on me. It took a while, she poked and pulled and grabbed at my balls, which were tender and frustrated from wanting to cum that morning but not being able to, and finally got the base ring in a good position. My balls hurt a little from being manhandled into the cage so to speak, but I’m a bit of a masochist and enjoyed the aches she caused. She then remembered the dick pinch thing I taught her earlier, and pulled my foreskin up and pushed my dick down inside, slid the cage on quickly, put the key in right away, turned the lock, and I was officially her chastity boy for what felt like the first time, despite having lightly played with this cage before. We used the FYJENNICC HT V4 chastity cage, the one we started with was purple, with the medium base ring and small tube. My dick is girthy and 6”-7” when fully erect, but I’m a grower not a shower, so it’s small when flaccid. We had previously used the cage for a few sixish hour long sessions, and I used it a few days prior to this story’s beginning for a 48 hour stint without issue.

I then offered to go down on her, and she accepted, knowing that I absolutely love licking her sweet pussy. I started slowly, lapping at her juices, darting my tongue in and out of her, and sucking up every drop of her pussy juices. After a while, I moved up to her clit, starting lightly flicking it with my tongue, worked two fingers into her wet and crazy tight hole, and would then finger her for a bit, pull out and lick my fingers, lick her pussy lips clean, then start again, building her up for the next wave. Closer and closer to orgasm I pushed her, pausing to cool that pussy down, then building it up a little higher than before. I love to edge her, she hates it, but it does give her strong orgasms.

I eventually hooked my index and middle finger back, and started to bang her g-spot over and over like you see in those squirting videos. I attacked her clit with my tongue, sucking on it and working it over in a random pattern back and forth and up and down, which was brining her to an inevitable orgasm. She knows she can’t hold back from me, she knows I will make her cum. She finally screamed out not to stop and keep doing exactly what I was doing. I was working her g-spot and cute little clit firmly now, she came hard, but just before her orgasm hit I locked onto her clit with my lips and teeth like a pitbull, lightly pinching it between my teeth like she likes. I aggressively sucked and tongued her swollen and super sensitive clit and hood while slowly but firmly rubbing her g spot.

She was in heaven, thrashing around for what seemed like forever, gushing juices on my face and hand, until she finally lay there absolutely exhausted while she firmly pushed my head away and said ‘enough pet.’ I sat there gently kissing her inner thighs for a few minutes while she calmed down. I love kissing her thighs after she cums. My face is always covered in her pussy juices, her thighs are covered, her pussy is glistening red and swollen, and it’s so sensitive she won’t even let me breathe on it at first. But eventually I’ll be rewarded by being allowed to gently lick her pussy clean, after it’s calmed down of course. Sometimes this excites her, and I start all over again until she has another orgasm or two. She knows how much power that pussy has over me, and she enjoys fucking with me from time to time. She’s grown to expect me clean her up after I orally please her. And I do. I can guarantee you that her pussy is spit clean afterwards. Every. Single. Time. I pride myself on my oral skills. But with my dick locked in a cage, knowing I wouldn’t be cumming that morning, and knowing I couldn’t go back home and jack off, I was more passionate than normal while going down on her, I knew my only sexual release that day and probably for the next seven days would be from pleasing her.

I remember the noises my mouth was making slurping and sucking away at her that morning, it just sounded sloppy and dirty, I felt like a slut which made my cock start twitching then throbbing. Then my balls started aching getting pulled and pinched from trying to get hard. I feared with horny delight that she might take notice of my additional enthusiasm the cage was causing, and exploit this someday.

It felt real, it felt like I didn’t have the ability to jack off or touch my dick. I suggested I draft up a contract, outline some general rules and ideas, and she agreed. After leaving her house with a caged cock, and not having the keys to the cage, I wasn’t sure where this would lead.

Later that morning I put together a general outline, and sent her a text with the rules. The rules read:

Keyholding Contract

– Mistress F holds the keys for 31 days. The chaste is not to be unlocked for the first 7 days. At the end of the 31 days it is Mistress F’s sole discretion if the chaste stays locked or not. The chaste is not allowed input, unless asked, after Mistress F takes ownership of the keys. With the understanding medical, emergency, etc exceptions are obviously allowed.

– The chaste will be restrained before the cage is removed to prevent him from touching Mistress F’s cock.

– Mistress F will at a minimum of once per week restrain the chaste for cleaning/shaving/inspection.

– If the chaste asks to be unlocked, asks to cum, answers yes when asked if he wants to cum, or even talks about the cage, 7 days are automatically added to the term for each instance.

– It is Mistress F’s sole discretion how, when, and if the chaste is unlocked after the initial 7 days.

– It is Mistress F’s sole discretion how, when, and if the chaste can achieve pleasure or an orgasm.

– If the chaste cums without permission, it is Mistress F’s sole discretion for punishment.

– Chastity play will not intrude into Mistress F’s daily life or restrict her own sexual satisfaction.

– If any of Mistress F’s sexual advances or requests are not met promptly and with enthusiasm, it is Mistress F’s sole discretion for punishment. Mistress F is strongly encouraged to be very demanding sexually.

– Mistress F will make an effort to frequently tease and arouse the chaste.

– Mistress F can add any rules at any time as she sees fit.

She agreed, and said that she will be taking extra liberties with rule number 11. I read that with excitement. My dick started twitching in it’s purple cage, getting semi erect, but when it started to swell and pull my balls up, the ring cut in and it went down after several minutes. I was then mildly concerned that I may have created my worst nightmare; this woman knew all of my kinks, all of my desires, and she know I’m pretty freaky with very few limits. She knew she was now in a position to explore her own fantasies, her repressed kinks, and her darkest desires, on a very willing boy toy that she loved, who’s cock she now had locked in a cage. She was looking forward to the next 31 days…to be continued.

Source: reddit.com/r/eroticliterature/comments/via733/chastity_keyholding_play_becoming_reality