By Josephine, on July 29th, 2010%
Be my Stripper Sissy
Ok girls it’s time for another exciting assignment to challenge your inner girl. If you have time over a weekend then take this sissy challenge and make me proud! Of course I expect you to post all the dirty little details here for ALL to see. If you have . . . → Read More: Sissy Assignment – Plugged Stripper Sissy
By Josephine, on June 10th, 2010%

Ask me ANY Question
Dear Goddess Josephine,
Should all sissies wear a chastity device and if so, what is good model that you’d recommend?
Also, how should a sissy be punished if he’s misbehaved – are self spankings given at a mistresses direction and with her watching (possibly via webcam) appropriate?
Thank you,
Sissy Brad
Dear Sissy Brad,
Yes, I absolutely think that an owned sissy slave should wear a chastity device. This keeps the sissy focused and mindful of his place. He should never be permitted to touch his little clitty without permission. He should also be kept in a perpetual state of arousal making his service more enthusiastic.
Continue reading Sissy Advice: should all sissies wear a chastity device?
By Josephine, on September 28th, 2009%

I know you want to feel like a sweet little prissy girl, however the reality is that you need to be trained to serve ALL of your Mistress’s needs. If you’re going to act like a girl then you need to do EVERYTHING girls do. Of course most girls don’t get any special training when it comes to fucking. Hopefully she won’t encounter a monster cock her first time when she loses her virginity. Lucky sissy at least gets to “train” to accept things inside of his “sissy pussy” or “nasty little whore hole”. (Humiliation and erotic embarrassment are important for sissy training )
This lesson is preparing and making sure that when mistress (or one of mistress’s friends) wants to fuck you, you’ll be able to take it without a problem.
Continue reading Preparing Your Pussy for Fucking
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