The Cuckold: The complete series 1-3: Femdom Chastity Humiliation

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His Keyholder may not be entirely aware of the heightened emotions swirling around inside the head of Her caged-up male.

cruise ship art] When a sissy and her wife decide to take a cruise, sissy things she will get a week on the ship to be a man again. Then ride him till he cums, then pick one or more of the punishments on this list to punish or humiliate him with.I would not tell him in advance but he would learn the identity of his key holder when he saw the key. When I have enough oral and want penetration, David puts on this 9″ sheath over his chastity cage and fucks me with it. Ask him what he thinks his size is, then get a tape measure and measure up, once you find out the size, tell him the truth, tell him how much size matters and that you wish he had a bigger dick, the kind you could tell your friends about, but instead, he has just a little clit. Using anal plugs, starting with small ones and working your way up are a great way to get used to the feeling of having things penetrate your anus and stretch it out a bit to eventually allow dildos or even penises if desired. I set how much cum I need him to create from one load, he can try it as much as he likes, but inevitably every time he cums less is created, and longer is needed between tries.

This is super hot because you can grind your ass into his chastity cage to make his frustration that much more of a torture! Follow this, once you’re done, by asking him to tell you why he messed up to make sure he understands. As noted earlier, his orgasms (if allowed) are always of the humiliating variety and primarily for Her amusement.As I was leaving the den to get the hors d’oevres, Nina said, “wait a second mister” and put up her hand in a stop sign.

Mistress has told sissy that she would get to go to a game day party, but did not tell sissy that she was going to serve the party, and that the guests would be hosted by sissy's ex-wife, who can't wait to humiliate her ex husband in front of her friends. Obviously, he was turned on by the idea; it seemed fair for me to play along — at least a little; for the sake of marital peace. Betty picked Tina up and the two entered the house–I offered them drinks and Nina showed them to the den and started gossiping about some neighbors who were getting divorced. There were giggles, gasps and talking between them “Oh my god-it’s steel” and “that thing looks so tiny” and “I can’t believe he agreed to wear that”, among other choice insults. There’s nothing like the power (and humiliation) of having some kinky fun in public where everyone is walking by.

If he can hold the coin either against himself or the wall for 1 minute he gets to cum, if not, the cage goes back on for 3 more days and he must thank you.

Do little inch markings on a really long dildo, he gets no reward until he can take (either orally or anally) all of the inches from the markings that you made. I almost screamed, scared to look at her, hoping that if we didn’t make eye contact, this didn’t really happen.When others in the home or school environment are fully clothes with long skirts or pants, this is particularly humiliating. I was balls-deep inside her and she came so hard on the first stroke down, I thought she’d pass out. We knew that she and her husband had a happy sexually fulfilling marriage — thanks to the common walls. She screamed, gasped and bared down and after some effort, I managed to get the head in when Tina came the first time. He had to wear the device anytime that I was going on a date regardless of what his key holder allowed.