Category Archives: Contests

Madonna Sissy Lingerie Contestants

Update: Ladies, the results are in. Judging this contest was no easy matter. Some girls got voted for multiple categories and Contestant #7 was unanimously voted as Best Vogue. Way to pose, girl! The Winners Are: Sluttiest: Contestant #1 Sexiest: … Continue reading

Posted in 2 Mistress Fun, Contests, Crossdressing, Erotic Humiliation, Exhibitionism, Feminization | Tagged , , , , , , , , | 3 Comments

Strike a Pose: Madonna Sissy Lingerie Contest

We had such a great time judging our Mistress Lillith’s Sissy Lingerie Contest that We’ve decided to run another one. We got so many sexy, slutty sissy girls entering that we almost couldn’t decide on the winners. Since every Mistress … Continue reading

Posted in 2 Mistress Fun, Contests, Erotic Humiliation, Exhibitionism, Feminization, Free Phonesex, Humiliation on Cam, Sissy | Tagged , , , , , , | 3 Comments

2 Mistress Fun: Small Penis Humiliation on Cam

I can’t tell you how much I’ve been looking forward to some Two Mistress Fun. My friend Olivia and I have so much fun humiliating men, that I figured she’d be a natural to join me on the phone. So … Continue reading

Posted in 2 Mistress Fun, Contests, Erotic Humiliation, Humiliation on Cam, Small Penis Humiliation, Stroking | Tagged , , , , , , | 2 Comments

The Jackoff Rides Again: Setting a Cockstroking Record

Today I’d like to talk about one of My more amusing pets simply known as The Jackoff. Jackoff is one of those pets that we Mistresses like to pass around and toy with. We just love edging him, hearing him … Continue reading

Posted in 2 Mistress Fun, Contests, Cum Drinking, Edging, Erotic Humiliation, Tease and Denial | Tagged , , , , , | 5 Comments