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 knows you can never have too many shoes or too much sexy lingerie, We’ve decided to challenge our sissy girls with a new contest: Sissy Girl Madonna Contest. Madonna has showcased so many different looks over the years, that you’ll have plenty of vogue styles to choose from. Start with her video collection on You Tube if you need a little inspiration choosing your favorite look.

In fact, that’s a great way to get inspired. I can picture My slutty girls already, prancing around the house in your hot pants while your sissy clitties swell as you dance to this Madonna Dance Groove Megamix.



Enter our Madonna Sissy Lingerie Contest

  1. Get all dressed up for Us.
  2. Put on your sexiest, sluttiest Madonna look. We want to see pointed bras, lace gloves and diva style.
  3. Send your pics to any of the judges via e-email to have your entry submitted before June 23rd.
  4. Check back here to see your fellow Material Girls get posted on my blog.
  5. We’ll be announcing the winners on June 26th.

Categories are for Sexiest, Most Authentic, Sluttiest and Best Vogue Pose. Winners will receive 10 free minutes with the Phonesex Mistress Judge of their choice or a free feminization audio.

Here’s a video for Madonna’s Blond Ambition Tour Makeup Tutorial for those of you who need a little extra help getting girly for Us.

Still not sure what to wear? Give us a call on Niteflirt and get on cam to show us the outfits you have in mind. We love a good sissy fashion show. You can even enter twice if you happen to have two fabulous popstar icon looks. Bonus points if you can deepthroat an Evian bottle for us a la Truth or Dare.

The Judges

Mistress Lillith-Evil Goth Mistress who loves to play with and out her sissies. Famous for Sissy Training Camp and her own addiction to humiliating you.

Click to hear her voice sample

Call Mistress Lillith for phone sex on Niteflirt.com

Sintellectual Jane-

You have a penis; she has a brain. Thus is the most accurate description of the sintellectually devious Miss Jane. Her peer-less expertease at dominating men from the top down helps to ease the age-old dilemma of which head controls a man … the answer is simple: Ms Jane controls them both! Her sharp wit and enticing voice will soon have you ensnared and you won’t be able to stop coming back for more. Be sure to check for her “Sintellectual Sunday” series on her blog for a weekly wrap-up of all things sintellectual.

Click to hear Her voice sample
Call Sintellectual Jane for phone sex on Niteflirt.com
Mistress Fernanda-Beautiful, but evil. A cruel humiliatrix with a silky voice. There’s no yelling here, but she will chew you up & spit you out. She’ll tease and torment you all the while listening for the sound of your desperate pleas. Of course since She really enjoys that sound, there’s not much chance She’ll be letting you cum anytime soon.

Click to hear Her voice sample

Call Mistress Fernanda for phone sex on Niteflirt.com

Olivia’s Naughty-When you call Olivia you get sassiness, sensuality, intelligence and soothing eroticism all in one. She can control your mind and ensnare your senses while turning you into a very naughty toy for Her pleasure. Her specialties include mind-blowing roleplay, small penis humiliation, guided masturbation and erotic hypnosis.

Click to hear Her voice sample

Call Naughty Olivia for phone sex on Niteflirt.com

Mistress Reaghan-Mistress Reaghan – with 20+ years experience perfecting the art of teasing, training and tormenting men into giving up their deepest desires – is many things. Just the right blend of gruelling sensuality and seductive cruelty, she specializes in helping men to realize their places in her world. And it is ALWAYS “Her” world you play in.

Click to hear Her voice sample
Call MissReaghan for phone sex on Niteflirt.com


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This entry was posted in 2 Mistress Fun, Contests, Erotic Humiliation, Exhibitionism, Feminization, Free Phonesex, Humiliation on Cam, Sissy and tagged , , , , , , . Bookmark the permalink.

3 Responses to Strike a Pose: Madonna Sissy Lingerie Contest

  1. Pingback: Madonna Sissy Lingerie Contestants » Wicked Phone Mistress

  2. Pingback: Shopping List for Sissies » Olivia's Naughty

  3. Pingback: Cindy, My Pet with a Slave Contract » Olivia's Naughty

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