So You Love Being In A Cage?
Orgasm Denial Again????
A wonderful pass the penis session for the pool boy’s 77th day of denial. Mistresses Mandy and Constance teased and denied pool boy with his fleshlight until he came to me for the final decision. As you remember, the deal was 100 days. I felt a great deal of compassion for this boy because he had gotten sick again, had several ruined orgasms with his girlfriend, and has had such a heavy work schedule. A deal is a deal though, 100 days we have decided. He has lost the weight however, but he can do much better. In the end after a stimulating conversation and stroke session, pool boy was given an anti-climactic ruined orgasm, and ordered back in the cage for the 100th day. This will be great. He will be away that whole week for in cage training, pass the penis, and perhaps an orgasm. Pool boy, I give you the challenge to lose 7 more lbs until then. That will certainly up your chances.
Cassandraville
Permanent Chastity?
Permanent chastity? I get this now and then. In fantasy or real time relationship, definitely. With online training, unlikely. A lifestyle permanent chastity agreement has a high success rate because of the close partnership of Domme and sub. Even in a real time situation, a Mistress will take her cock out for a little exercise and examination. A male does not need to cum on a regular basis to keep a healthy prostate. Prostate milking is mostly a humiliation exercise. Online permanent chastity training is a huge challenge that lies in the court of the chastised. Do you want to be in permanent chastity? Are you willing to acquiesce all control to a Mistress you love. With knowing you can remove the cage whenever you desire, will you resist? What does it take? Extreme intent! Can you imagine permanence? Nothing in these great universes are permanent. Boring!
Chastity Mistress Cassandra 1-800-730-7164
Thank You Ms Constance, Ms Mandy for the wonderful warmups for Mistress Cassandra’s evil ways. After 77 days stroking and a ruined orgasm was definitely better than a long tease and being locked up immediately. Thank You again. This session was worth the wait. Oh yes, challenge accepted.
counting down to 100 days! pool boy
I can imagine the immense release your chastity slave felt at having his long awaited release. I love that Ms Constance and Ms Mandy worked him into a lather, and then sent him back to you. Love it! Clearly, your guidance is working as he is dropping weight and being such an obedient boy. Is he considering permanent chastity? That is a big step, but one that thrills me like little else. *grin*
OMG Ms Cassandra, 100 days is what this boy needs to drop even more lbs and to stay happy. I know he is happy after having three Mistresses torment him today. I suppose he was hoping for a happy ending…wellllllll, I say it was very happy.Kudos to you and to him and his acceptance of a ruined o!
100 and counting maybe Ms B?
Mistress Cassandra, I didn’t realize how fun that Pass the Penis game really is! It sounds very tempting especially with all sorts of toys that inflict fun things upon the user. Tying a boy’s chastity to losing weight seems devilishly effective, too; maybe I should inquire about that as weight loss is definitely one of my own goals.
I’ve never tried prostate milking – definitely on my to-do list for the future. Thank you for this blog post, Mistress.
Youre so welcome daniel!
OMG Permanent Chasity is sooooo mean! I absolutely adore you. I don’t think I could do it because I like to hear the men cum and scream in My ear too much. I think it’s amazing both your control and your subs. 100 days is such a long time for a sub. Do you recall what the longest is that a submissive has gone for you?
To recall that is to love it, 456 days! Thank you Ms Simone 🙂
So he’s been dropping those pounds? Excellent! I love hearing positive reports of progress. That is truly a testament to how devoted he is and how revered YOU are. It must feel good to know that you are such an inspiration to pool boy on his journey. I’m sure he was worn out after that last game of pass the penis.
LOL, well he got a ruined orgasm, always fun Ms Alexis, thank you!