by Sissyville | Jul 12, 2017 | Cuckold, Hot Wife, Sissy Assignments
So, This Sissy had a Visitor Well, really it was the Hot Wife of said sissy who had the visitor. And no, not one of her usual Bulls. It was one of her girlfriends and she stayed for the weekend. That’s not to say there wasn’t any cuckolding going on! Those two...
by Sissyville | Jun 8, 2016 | Sissy Assignments, Sissy Boys
I’ve been doing a lot of thinking about my favorite kind of sissy. The first type would have to be obedient, but aside from that, each kind of femboi holds a certain level of appeal to me. At the end of the day though, I like the kind who aren’t afraid to...
by Sissyville | May 18, 2016 | Sissy Assignments, Sissy Crossdressers
Uh oh! You lost a bet with me, and now you have to do whatever I tell you to do. Too bad I know all of your secrets! Oh you don’t know I am aware of your sneaking around while I’m out with friends, putting on my panties, my bra, my stockings, and my high...
by Sissyville | May 10, 2016 | Feminization, Sissy Assignments
Feel more like a sissy by wearing a prom dress. Buying a prom dress, of course, signifies that you are going to go out on a hot to trot date with some super smokin’ boy. Well, that may, or may not, be the case for you, but you can always get dressed up and have...
by Sissyville | Oct 31, 2007 | Sissy Assignments
Sissy Dress Up Going out dressed as a sissy can be terrifying, exhilarating, and liberating (or a mixture of all three). We think you’ll have a lot of fun with this mini sissy assignment collection from Mistress Heather. She loves to play sissy dress up and is...
