Poor Sissy….Clueless and Dickless!!
Hapless Sissy
So I get this call from a clueless little sissy who is trying to figure things out. I have to dig in the deepest depths of this poor little sissies head to figure out why her brain is so ditzie, girlie, and clueless. She has a cute little name, sissy jayme and from our conversation she certainly knows how to put on lip gloss. I wonder how I would have reacted if I were one of the girls she ran in to who helped her with her lip gloss.
Lip Gloss For The Gurl
I would have reacted this way: Oh hello….you are a sissy? Yes? Show me how you put your lip gloss on. Then, no matter how good she was at it, I would find one little thing to torture her about. She would have no need to ask me if she is a sissy, she would know it after she got top shelf humiliation from me.
Yes You Are A Sissy…Yes!
More questions come in like does this mean I am a sissy? Does this mean I am a little faggot because I suck cock and eat cum? Do you think my mother knows because I steal her makeup? The answer is YES…a big fat yes! Perhaps she is happy because you don’t steal her panties like other sissies would. Poor poor little sissy jayme. Such a little bimbo!
9 Days??? Is That All You Got????
I answered a comment in Cassandra’s Playground from a boy who said he couldn’t last nine days in chastity. Nine days is a start and will lead to nine months. I have fuckie now chaste for 6 months, sissy donna is somewhere close. On weekly reports I insist on the ticker…how long. I can certainly look it up but I prefer the boy to. This way it makes him think about how lucky a boy he is. Pool boy has been sick withthe flu, so on hiatus. Looking toward a lively spring!
Chastity Mistress Cassandra 1-800-730-7164
I think that we are all the poor lost souls of many sissies. I think that it is actually cute when they email us or call us telling us their most darkest secrets. Or when they confide in us telling us they do not understand their urges. Poor things, they have no idea what big sissies they are. I just feel so much better when i have a rescue a sissy from further embarrassment.
They definitely achieve catharsis with us Ms Gia
Oh yes, how easily nine days can turn into nine months! What is the absolute longest you have ever had a little sub in chastity, Ms. Cassandra? I am so curious! I have one sissy who is going on four years. She has actually crossed that place where her regular orgasms are anti-climactic and she prefers prostate milking!
5 years with fuckie fag boi Ms C!
My, my, my, Ms Cassandra. You have quite an impressive catalog of male chastity sluts. I hope they DO realize how lucky they are to serve a queen like you, as made further evident in that awesome photo. I did have to giggle when I read 9 days though. Ahh, they always THINK they know what they want until they are locked down in chastity. Then there’s no turning back.
Imagine that Alexis…9 measley days!! Wimpy wimpy!
Oh Mistress Cassandra, it’s so thrilling to read about our phone session.
Yes, lipgloss is my favorite article of makeup, close behind eyeliner.
But I don’t steal from my mother, I just borrow a sample when she gets a new lipstick.
She has dozens so she wouldn’t miss one little lipstick. Besides, we use the same razor
and shaving gel for our legs.
I enjoy being a gurl.
Oh right …she knows youre a little sissy faggot…my apologies 🙂
believe me i’d rather not be sick. this really really sucks …