Feminine Cruelty

Men are like grass, born to be stepped on. Since people keep asking: Yes, I do online keyholding. Msg for pricing [CURRENTLY FULL. WILL POST WHEN NEW SLOTS ARE AVAILABLE]. Yes, I rate dick-pics. It's a $5 flat fee. Not in this for the money, but I need some way to filter all these requests. For everyone else, enjoy the pics/captions! 

Last update
2022-03-12 07:03:43

    “Look who’s finally home. Didn’t I tell you to be here right after work, today? You’re half an hour late. What do you mean ‘the boss kept me late’? I’m sorry, does someone other than me have the keys to your chastity cage? No? Just me? Then I guess that means I’m your boss, doesn’t it? Your only boss -- and you’ve just wasted your boss’ time. 

    Do you have any idea how valuable my time is? Every minute of my time is worth a day of yours. See where I’m going with this? You wasted 30 minutes of my time, so I’m adding 30 days to your chastity sentence. That seems fair, don’t you think? Now come suck my toes and tell me how sorry you are.”

    “Awww, it’s so cute when you get upset. Are you gunna cry? I can tell you’re about to cry. Your little weenie always shrinks up to the size of a button when you’re about to cry. It’s okay baby, let it out. Life is so unfair, isn’t it? All you want to do is cum, but your mean ol’ girlfriend won’t give you back the key to your cage. Well sorry babe, I told you this chastity sentence would be longer than the last one, but I never said I was going to tell you how much longer it would be. Isn’t not knowing more fun, though? Honestly I envy you. It’d be way more fun for me if I didn’t already know how many more months you have to go.

    Oops, I guess I just dropped a pretty big hint, didn’t I?” 

    The ‘feminization’ process was almost complete. After intensive training and over a year in chastity, your muscle mass had reduced 30% and your penis size had reduced to barely an inch. In addition, your many months engaging in marathon strap-on sessions had completely removed your gag-reflex and conditioned you to only orgasm through direct prostate-stimulation. You were no longer a man, but now it was time for you to be made into a woman -- 

    As your Mistress firmly held you in place, you saw an approaching figure. You could only see him from the waist down, but it was enough for you to see he was armed with the largest cock you’d ever seen in your life. It had been weeks since your last orgasm, but was the pain this man would surely bring be worth it? Either way, your Mistress demanded it, and whatever she wants, she gets.  

    “No, I wasn’t joking when I told you your chastity cage was permanent. Still don’t believe me? Check the keyhole on your padlock. I filled it with superglue while you were sleeping weeks ago, so even if I still had the key it wouldn't’ do you any good. 

    Of course, the cage is only permanent so long as those big blue balls of yours keep you from being able to slide the cage off, isn’t that right? Oh look, I left the door to my display case open. So tell me babe, how badly do you REALLY want that thing off?” 

    “Oh you’re back. Well, how was your first day at work now that you’re my chastity-bitch? It’s a rhetorical question, babe. I don’t actually give a fuck. You can start by making the bed and then go cook me something for dinner. Yeah, I know you already made the bed this morning. So what? You can see that it’s a mess again, can’t you? Make the bed and toss any used condoms you find. 

    You heard me. You did realize me fucking other men is part of this whole chastity thing, right? Well, you know it know. If you have a problem cleaning up another man’s used condoms, I can always let him hit it raw tomorrow. Either way you’ll be spending your evenings eating me out, so you should probably decide now whether you prefer the taste of latex or dick.” 

    “Alright loser, now that you’ve got that Humbler on, you have 30 seconds to crawl all the way to the end of the field while I pelt your nut-sack with this paintball-gun. There’s no reward for succeeding, but if you don’t make it in time you’ll be crawling all the way home wearing that thing. It’s about 100ft to the other end, so I’d get going if I were you. Time starts now.”

    “I have to say, I really appreciate that you wear that chastity cage for me. It makes me feel so much better about our friendship knowing that you really are spending time with me for me, and not because you’re trying to get into my pants or something. I could never be alone with another guy like this without it turning into something sexual, so it means a lot to me that we’re able to keep the ‘innocence’ of our friendship, like back when we were kids. I’m sure one day when you meet the right person, you’ll make her the happiest woman in the world -- just as long as she’s cool with our special ‘arrangement,’ of course.”  

    “You sure about this, babe? This is a big step. I mean, you’ve seen the dick pics he’s sent me, right? He's enormous. Even if I let you fuck me again one day, I don’t think I’d even be able to feel you after he’s done stretching me out. You sure it’s worth it? You sure you’d rather let another man fuck me than have your chastity sentence extended 3 months? Well, okay. Wait here. This shouldn’t take more than an hour or two.”

    “Babe I’ve been thinking -- You know how we have a semi-open relationship where I can see other men but you have to stay exclusive to me? Well, I’ve decided I want you to start wearing this chastity cage, too. The thing is, you aren’t really being ‘exclusive’ to me if you can just choose to ‘have sex’ with yourself anytime you want, right? Exclusive means exclusive, so show me how much you love me and put this on. Make it quick though, I’m already late for a dick-appointment.” 

    Your wife introduced her sister to chastity-play, and she took to it quite eagerly. She even came up with a ‘fun little idea’ for you and her husband. Every time one of you gets a release day, the other sub has to eat his cum. When you get a release day, he has to eat your cum, and when he gets a release day, you have to eat his.

    The only problem is that your sister-in-law is a far more ‘generous’ domme than your wife. While you stay locked every day except for your birthday, she gives her husband weekly releases, and loves to treat him to blowjobs. Now every Sunday you’re having them over for dinner, with a hot load of cum being your weekly dessert. You hate every second of it, but on the bright side, only 40 more weeks until it’s your turn!