by Sissyville | Jan 19, 2025 | Sissy Assignments, Sissy Humiliation
A few years ago, I posted a pillow-humping blog where I described my first orgasm and how a pillow was the winning climax. That got me to thinking about dakimakura pillows, and how much fun it would be to have a sissy hump one for me under my guidance…. What the...
by Sissyville | Oct 9, 2017 | Feminization, Sissy Assignments, Sissy Humiliation
I love the power I hold over a man sissy when she’s in a CFNM CFNS situation, but I have to admit, I never allow my sissies to be completely naked! It’s far more humiliating when a sissy is wearing something slutty that makes her more naked than naked....
by Sissyville | Jun 16, 2017 | Cum Eating, Sissy Assignments, Sissy Humiliation
I had written about my naughty little sissy cum dumpster never being satisfied with her assignments, no matter how dirty they were. She sucked cock on cam, she spread her legs and got fucked like a little whore while I watched, she pranced around in public wearing her...
by Sissyville | Nov 28, 2016 | Sissy Assignments, Sissy Humiliation, Sissy Maids
Masked sissy humiliation parties during the holidays are fun! What is better during the holidays then a masked humiliation party made just for the not so shy sissies. Now, granted humiliation is not for everyone, and parties are not for everyone either. But, for...
by Sissyville | Jul 22, 2016 | Sissy Assignments, Sissy Humiliation
Sissy, some of you long to be exposed. I know this from almost six years of training you, encouraging you, helping you to accept your nature, to form your sissy style, and yes, also through putting you in your place via humiliation. Countless numbers of you have told...
by Sissyville | Jun 22, 2015 | Crossdressing, Sissy Humiliation
I love to humiliate my pets by requiring them to wear women’s clothes and taunt them about what would happen if they are caught crossdressing. I never expect them to actually get caught crossdressing, of course, but I can’t be held responsible for dumb...
