Gear up for one of my favorite sissy fantasies. The school girl! Enjoy 🙂
The school girl sissy dressed in a school girl uniform is one of my favorite looks and fantasies.
The jumpers should be plaid, preferably in sissy pink. A crisp white shirt with long or short sleeves depending on the season and a pink ribbon around the neck is so sweet.
The outfit absolutely must have white cable knit knee socks with flat pink mary jane shoes in patent leather, or simply just leather.
Underneath it all, a white lacy training bra with white full cut panties to match makes it most authentic. Pink is fine for theatrics, especially if sissy has a little pink chastity device ordered by Mistress. I DO mean little! I imagine a new chastity device manufacturer devoted to little dicks, geared to sissy humiliation.
The wig can be any color, but it must be a long bob with bangs, long enough to accommodate ribbons for pig tails. These are just the basics. The school girl can be a slut as well. She could be a heavily made up trollop or a sweet innocent makeupless waif. The slut would have high heels and thigh high stockings instead of socks and mary janes. Her uni may be red plaid to match her red lipstick. The slut would have big DD breast forms with shirt unbuttoned to the bra with no sweet ribbon.
Her uni will be shorter and hair ribbons are not an option. The slut would most likely be a little cocksucker for Mistress. Her nails would be long, red, and her fingers would be wrapped around a big hard cock.
Sound like you sissy?
Mistress Cassandra 1-800-730-7164




Oh yes, sounds like me Mistress
Oh Cassandra, you mentioned pigtails! I love pigtails.
Okay, I am not transgender and I am not gay, I am a heterosexual submissive to women, but I love feminizing emasculating sissy role plays.
When I am her maid, my preference is for a sexy maid outfit, and I am the eye candy for her and her female guests, the feminization is for feminine enjoyment.
Sometimes however I like the role where Mistress is using me as a sexualized submissive for the eye candy pleasure of men in her life.
When in that role, I put up with being sexualized and objectified by the men in her life because Mistress wants it and I am ensnared by Mistress, and enjoy doing it because I am doing it for her, my Mistress, and she wants me to do it, so I want to put my full heart into it and be the best sexualized object for the men in her life that I can be, I trust Mistress will never allow them to treat me badly but will protect me.
That’s the state of subspace I am in when I like the schoolgirl sissy role play.
Normally I see myself in black mary janes, but I know you like pink so yes, for you it would be pink.
And my hair would be in pigtails, because when on my knees giving a blowjob to the men in your life, I would want them to have the best sissy blowjob they ever had.
Psychology note. I like Mistress to get the cock she needs to feel satiated, the skill in bed she needs to feel satiated. I do not however like to visualizing Mistress sucking his cock. Whether she does or not of course is her choice, if she enjoys it, that’s her prerogative. Guys like having their cock sucked, so maybe if I do that, I’ll meet that desire for her man and she won’t feel the need to do it herself as often or maybe at all.
When I as a man fantasize about getting a blowjob from a schoolgirl, I fantasize about holding her pigtails as handles. So when I am the schoolgirl sucking cock for Mistress, I need to have pigtails for the men (or Mistress if she has a strapon) to hold on to.
I do not crave cock in my mouth, but I want the men in her life to believe I do, because even though I crave Mistress and wish that I could have her, I want to make it very clear to any man she has over that I am not their competition and I accept that and even embrace that, because that is what Mistress wants, and showing my devotion to her is the most important thing to me when I am in subspace.
And oh how I do crave to be in subspace.
Does this make sense? It doesn’t need to, because it is fun, and that’s what really matters.
Your input and insight is always appreciated Alice Wonder!