Out of the three scenarios, which do you prefer? Listening to them close the lock on the cage, locking the cage yourself, or a surprise key in the mail/locked pic?
Well, I prefer personally locking. It’s so much more exciting and fun to do it in person. Plus the boy is so conflicted about having me so close to his little buddy, but only to lock it away from him.
I like making a game out of the locking ceremony. I remember one boy who was really cocky. The overly-competitive gamer type, you know? I told him to put his hands on his head and close his eyes while I got everything set up. I offered him a chance to avoid chastity if he was fast enough. I told him if he could get his hands on the lock (while keeping his eyes closed) before I locked it then he wouldn’t have to undergo chastity. His hands darted from his head straight for his groin but I already had the lock in place and my fingers were pushing the hasp down. Snap!
I do enjoy watching boys lock up over skype. I’m not sure I’ve ever listened on the phone. I should try that.
I’m sure I would enjoy getting keys in the mail. But, you see, that’s not how I operate. I send out the locks and retain the keys. When a boy accumulates enough locks he’ll mail them back to me and we can reuse them.
making him fuck your hand as a "trial run" before you even let him see your pussy
Jennifer Love Hewitt
Of your three “regular” babysitters, she was undoubtedly the nicest. She at least did the least to humiliate or tease you.
One babysitter used her time with you to let out her inner Domme. She was exceedingly strict and any disobedience, even if it was a miscommunication, resulted in punishment. And she was extremely creative with punishments.
Your other babysitter loved nothing more to tease and humiliate you. Whether it was inviting her friends over to taunt the “diaper boy,” or just spending the entire night in Gryffindor-colored bra and panties, with thigh-high Gryffindor socks, making you wish you were a man, she left you would be positively aching down there with insatiable arousal.
But she was different. She wasn’t mean. She didn’t tease you. And, for some reason, you weren’t sure if that made her the worst.
If someone made an audio recording of her time with you, they would be convinced she was babysitting a toddler. It drove you crazy. It was one thing to be bossed around or teased. At least those babysitters acknowledged you were an adult, even if you were just a diaper boy.
But not her. Nothing she did, nothing she said, ever made it seem like she knew you were an adult. It was so convincing, so authentic that you honestly weren’t sure if it was an act.
She had never broken character once in the last five years. You tried everything you could think of to prove you were an adult, to force her to recognize—even for a second—that you were actually an adult.
Your attempts rolled off her like water on a duck. As far as you could tell, you were a toddler to her. She never let you out of her sight, except for your naps and sleepy time of course.
You had absolutely no dignity around her. She dressed you as she wished, checked you when she wished, and changed you when she wished. She blew raspberries on your tummy like it was completely normal.
You watched educational baby cartoons on a non-stop loop. And she always, always encouraged you to answer along and was just so proud of you for getting the right answers.
And nothing entertained her more than having you sing along with her to your “favorite” songs. You could never convince her you didn’t love singing and dancing to Baby Shark in nothing but a short T-shirt and soggy diaper.
All this because your bladder stopped working like it used to. All this because your girlfriend couldn’t handle your diapers but couldn’t break up with you.
But as you hear “The Wheels on the Bus” play for the 100th time, you know you need to start dancing…
Never ever princess.
dangerousangleofadream.tumblr.com/archive dangerousangleofadream.tumblr.com/random
9K posts