Category Archives: Sissy Contest

Season of the Sissy

Spring is in full swing and before we know it…it will be summer! I always say that the summer is the season of the sissy.

Summer time is when you get to see the tiny little shorts, the pretty sun dresses, the sexy little bikinis. There is such a variety for sissies and fembois to look at during the summer that they feel a surge of the urge. The inner sissy becomes overbearing and you will feel that all too familiar sense of femininity.

What would you give to sit poolside in a slinky little bikini sipping on long island ice teas just sprawling out in the sun while real men gather around you for some…extra fun in the sun…and defining Sex on the Beach.

You can feel the urge, and now it is time to feed the need. Giving in is the only way to calm it. Although, it is a double-edged sword. Feeding the need grows it…but ignoring it makes it stronger as well. Best to feel some relief while you grow the urge to be feminized and sissified. Your Sissy Trainer Mistress will help urge you…FORCE FEMINIZE you if necessary. It is absolutely what is best for you.

Why not go and get that mani/pedi, go paint your nails and shave your legs. Go prep yourself for the most fem-chic season of the year.

Have you been feeling a little extra feminine lately? Have you bought a new shade of lipstick or a new outfit? Show it off below and I’ll be sure to tweet it out!

  • Post your picture in the comments below and tell me how much you love the season of the sissy. Include your twitter tag where available, and if you added to your collection or pulled out an old favorite let me know 😉
  • *Must include a sign that clearly states Summer Sissy fun @Mistresslillith .  Without the sign your post will not be acknowledged. A face picture is great but not necessary 😉 *
  • Don’t send me a link to a website with a slew of pictures. Only new/current ones that follow the rules above. Deadline is the end of the summer season 😉

Sissy Lingerie Contestants

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. 😉

 

Sissy Lingerie Competition

Lingerie Competition - Sissy Dressing Contests - Mistress Lillith - www.sissydiaries.comI 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 30th with the winner announced May 7th.

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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