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November 2018
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Pushing The Orgasm Challenge

Mistress Cassandra 1-800-730-7164

Pushing the challenge for fuckie fag boi may be in order. So far over 3 months chaste and up a whole cup size is quite a feat, but I think she can do better. Sissies need strict observance and training. Orgasm denial is simply not enough. Time will tell, and we will see. Maybe a little sissy outing assignment may warm me up to allowing a nice little release. Lately I have been testing my ability to give ruined orgasms. I seem to have them down by listening to a boy’s breath.

135 Days And Counting

Sissy donna ,135 days and counting, only 15 days to go and it will be 5 months in chastity, longest ever. Preparation for the big day is simply be prepared and to expect the unexpected. Normally I would send her out crossdressed to do some assignments, but her brother is staying with her indefinitely. The problem is her brother sits and watches tv 24/7 and donna cannot get past him dressed in sissy. TV is the great controller. Frank Zappa called it “the slime from the video”. If you sit too long viewing your addiction, you will notice that your back tends to hurt (unless it’s “Breaking Bad” or “The Walking Dead” that is). So if you think you can slip past him, donna, let me know!

To Ruin An Orgasm

Speaking of ruined orgasms, what is required for the best possible experience, have a web cam for viewing and observance, do not mute your phone, and be willing to talk about it for a few minutes before hanging up. One disappointing call I did awhile back was a boy muting his phone during training. How could I tell? My psychic abilities are not finely tuned to if a boy has orgasmed or not. Heavy breathing does not offend me. Do not mute!

Chastity Mistress Cassandra 1-800-730-7164

10 comments to Pushing The Orgasm Challenge

  • susie

    135 Days. That is commitment and devotion. Both Mistress and sissy should be very proud.

  • I love hearing about your chastity pets Ms Cassandra! sissy donna’s chastity torment makes me smile! That sissy DOES have the attention of The Dicktator! hahahahhaha Oh and I just wanted to second your comment about muting the phone. Awwww. For me, hearing the moans and gasps and begging and so much more on any phone sex call is why I love this! I’m visual, yes, but there’s something about hearing a man in chastity whimper that just gets me going. Oh and you’re right….combine a phone sex call with being on cam ~swoons~ OH MY!

  • vanessa

    hurray for fuckie fag boy and sissy donna! Most awesome the records you two put up! And, hears to Mistress Cassandra for being the awesome Mistress she is, giving you two the inspiration to put up such records!

    As for me, since having my sissy prissy pierced, i still haven’t been able to wear a cage for more than a couple of days with out experiencing pain indicating a possible tear or infection! If i’d only known about the Manhood Academiy’s Komiiti 8 before getting pierced!
    As for my noogleberry training, i’m getting large enough, it’s just a short matter of time, before my breasts are so big that they are undeniable! My nipples have gotten very sensitive and in a t-shirt with a brisk breeze, I’m excited to say that, i’m been nipping out! They should be very noticeable very soon, at this rate! Hopefully some cute girls will take notice and be blatantly laughing at me soon!

  • 135 days? Well done, Ms. Cassandra!I know you have put this sissy Donna through her pretty pink paces. A nice ruined orgasm is always a good outcome. You are right, sissies need strict training. This one creates some problems with the whole couch potato brother, but she can be discreet. But I am still in favor of a ruined O because, O why not!

  • oh yes, Mistress, any form of release would be welcome, even better if it involved a slutty sissy assignment whatever you say!


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