Category Archives: Lingerie Contest

Attention Whore Sissy, Lingerie Contest, Mistress Lillith, Sissy Humiliation, Sissy Outting, Sissy Stories

This Sissy LOVES Red Lipstick

August 27, 2014 Lillith 5 Comments

How many of you sissies enjoy slathering on that smooth, creamy, lipstick. For some of you that is your absolute FAVORITE part of getting all femmed up.

For my sissy, Jessica Michaels, red lipstick is her absolute favorite.

While so many girls and sissy girls clamor over the 50 shades of grey…THIS sissy falls over 50 shades of RED. This is what she had to say about her red lipstick:

I really love putting on and wearing women’s lipstick. It feels so smooth and sexy on my lips. The way is glides across them creating a slippery, shiny coating. It can never be a light shade, it always has to be a dark slutty color. The kind that stains my lips when I’m wearing it so I might not be able to hide it the next day.

It makes me feel sexy and at the same time, completely humiliated.

To be a man wearing tons of bright red lipstick is embarrassing and exhilarating. But the feeling of it on my lips, the smell, the taste. Makes my heart pound in my chest.

The latest one, a color called “Tempt” is long-lasting, but also has some lip plumper in it. It makes my lips tingle as they become more pouty and the color sets into my skin.

Mistress Lillith loves making me put on tons and tons of it, making me ask repeatedly for more and more until I can not take it anymore. Then she makes me add more still.

I love that she is turning me into a helpless sissy lipstick addict for her amusement. I can’t resist the feeling when she tells me to “put on LOTS more”.

I fear my future as a lipstick slut, but I also can’t help but love the idea of having constantly red and shiny lips for everyone to see what a naughty little lipstick slut I have become for Mistress Lillith.

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So now I ask all of you sissies…what color lipstick is YOUR favorite? What is your favorite part of dressing up?

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Attention Whore Sissy, Lingerie Contest, Sissy Contest

Sissy Lingerie Contestants

May 5, 2013 Lillith 4 Comments

Hey there sissy girls!

I have collected and sorted all of the the sexy, slutty and cute lingerie photos that all you sissies have sent in. I think the sissy trainers and I are going to have quite a bit of fun judging and deciding who looks the best in what out fit.

There are 3 categories: Sexy, Slutty and Cute — each sissy chose their own category and/or submitted a couple of different shots for a couple of different categories. I think we may throw in an OVERALL and maybe even a viewers choice 😉

Look at all of these sexy sissies below and leave a comment on whom your favorite is !

Here are all of the CUTE SISSY LINGERIE OUTFITS:

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Here are all of the SEXY SISSY LINGERIE OUTFITS:

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Here are all of the SLUTTIEST SISSY LINGERIE OUTFITS:

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AND here is our Glamorous Sissy ~

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The Fergie song G-L-A-M-O-R-O-U-S is now stuck in my head. 😉

I also put all of these entries on my twitter for the world to see. Nothing like outting a sissy! (One of my favorite pastimes)

and lets not forget to give a shout out to the judging mistresses:

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Good luck sissies! We all know you did a fantastic job getting on your lingerie and taking some pictures or even having us take the pictures during sissy training sessions while we watched you on cam. 😉

Lingerie Contest, Sissy Contest, Sissy Training

Sissy Lingerie Competition

April 16, 2013 Lillith 2 Comments

I love sending my sissies through my sissy training camp. Being able to aid you in your fem chic journey is something that excites me and puts a smile on my face.

If there is one thing I know about my sissies, is that they LOOOOVE competitions—they love the attention from it, and the idea of being crowned TOP SISSY and the adoration of other sissies and mistresses alike.

This little competition will be fun and sexy, just like some of my best bimbo sissy sluts like!

So what kind of online sissy competition is this one?

~This round will be a Sissy Lingerie Competition~

Grab your sexiest, sluttiest, or cutest lingerie get all dressed up like you are dressed to impress (impressing the mistress judges, or like you are dressing to impress that sexy big black man with his delicious big black dick)

Get a few snap shots or show of your sexy sissy self on cam for myself or any of the judging mistresses.

How Do I enter the Sissy Lingerie Competition?

There are a couple of ways

(1) You dress in your favorite lingerie. Panties, bras, chemise, high heels, nylons – the works, and whatever you chose to wear—take a few snap shots and send them to me in a message either a message on Niteflirt or via my yahoo messanger. Include in the message that it’s for the Sissy Lingerie competition.

(2) You can call one of the judges, show yourself on cam, and allow us to take a couple of snap shots.

**You do NOT have to show your face in the images, but know that the images may be placed on our blog as we decide the winner of this particular competition.**

Show us what you got! The images will be judged by category – sluttiest, cutest, and sexiest

Who are the Mistress Judges?

Each of us sissy trainers loves to have our sissies competing…not just for the sissy crown but for our adoration as well (What is more pleasing than pleasing your mistress?)

In this round we have 4 judging mistresses–Myself, Mistress Fernanda, Mistress Reaghan and Mistress Olivia. Here are our head shots that link to our blogs, as well as a call button if you want to get to know each of us a bit better.

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Competition starts NOW

It starts NOW and I will be accepting submissions until midnight eastern, April 30^th with the winner announced May 7^th.

This is sure to be just the first leg of our summer time sissy competition series, so enter them all because at some point, we will have the overall completion to crown the queen sissy!

So maybe it’s time for you to go out and get some NEW lingerie? Hell what girl (born or sissy-made) doesn’t want new lingerie?

Have fun and good luck!

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