I never met a sissy who did not like butt plug training. If you are the exception to the rule, perhaps I could convince you otherwise. Give a listen:
I think it’s time for some intense butt plug training for sissies who have had it a bit too easy.
First we will have to purchase the product or products in mind. A butt plug kit, small, medium, and large. You are done with your skinny little fingers and vibrating dildos that are small dick specials. You are now ready for the big league. There will be no ordering online. You will go to the sex shop dressed enfemme, and you will ask the pretty, kinky, and dominant woman behind the counter to help you choose the set I have ordered you to get. Do not get it in pink. Black will be your only option. Just do it , sissy!!
While you are there, I want you to check out the kinky wear and buy a little French Maid uniform in any color available. Ask the Domme in a faggy little limp wristed voice “Oh Mistress…don’t you have pink for a little sissy like meeeeee”? 🙂
Here we go, try it on and model it for her. Ask her is she has any locking panties that sissy’s chastity mistress would approve of.
Now that you are totally humiliated, I want you to go home and begin your work starting with the small plug. You will wear it for a week. After that week while in complete orgasm denial, you will wear the medium plug for 2 weeks. Still no orgasm.
For the next 3 weeks you wear the large plug. Do you now deserve the orgasm? Hmmmmmm, let me see if I can get an even bigger plug, which of course, I can…then we will see!
Mistress Cassandra 1-800-730-7164




hi mistress cassandra!!! you seem like such a super sissy teacher youre so awsome!!!! ok i like keep seeing these cute pink butt plugs but i dont know if i should get one or just get a dildo instead *humpf* 🙠what do you think mistress casandra?!?
butt plug training first, dildos second!
When it Comes to ButPlugs i think i am a well trained DOGG when it comes to the subject cause i’m 32 years old now and i’ve been using anal toys on myself since I was 16 Years old.
So for me to make it’s more interesting is to use Anal Toys During a Guided Masturbation Session, hvat i Have is an inflatable ButtPlug so what do you think??
I think you need to use it, and OFTEN!
All sissies need to be well-acquainted with buttplugs for the sole purpose of being ‘ready’ at all times. Ready for what, they better not ask? =)
Ready for a fat strap-on at the hands of a Mistress and her friends or ready for a thick cock for real, just because they strike someone’s fancy. Maybe it’s the shifty Alpha at the naughty video store or the guy that’s taking care of their wife. Sissies and cuckolds alike need to be strrrreetched on a regular basis! Glad to see you cracking that whip as always, Miss Cassandra!
Cracking my whip and restraining the dick…that’s me Ms Amber 🙂
Oh Mistress Cassandra-
I love how you imitate the high pitched fag voice of the sissy.
The next time I phone for you I will try to maintain my femme faggy sissy tone of voice for our entire conversation. My most recent purchase from an eagerly helpful woman toy consultant at Lion’s Den is a butt plug that I can pump to expand my sissy hole wider. She also recommended a 24-hour lip stain by Maybelline that she assured me wouldn’t wear off while I suck cock.
Inflatable butt plugs are for pros like you, my dear, and of course you would utilize lip stain….Dick Breath jayMe 🙂
Mistress Cassandra You know how to handle us sissies!
I certainly know how to handle you. I feel you getting very frustrated…oh yes!