This Sissy LOVES Red Lipstick

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:
red lipstickI 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.
photo (9)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.

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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Sissy Damsel and a Coerced Encounter

Have you ever pictured yourself as being that ‘damsel in distress’…that helpless little sissy girl looking for the ‘protection’ of a dominant mistress?

Perhaps you have come to my domicile for a day of pampering and sissifying. You are seeking a certain type of protection from your mistress…protection from REAL men who only want one thing from you.

After dinner is done, and you have done your sissy maid duties, you go to get ready for a nice slumber. Your mistress has allowed you the privilege of sleeping in a comfortable bed covered in satin sheets and comforter.

You put on your slinky little chemise, the one your mistress has laid out and you decide to forego the panties she has laid out. You start to remove your make up, but you look just like a porcelain doll and don’t wish to remove it all…you leave your eye makeup and your lipstick.

You climb into bed and close your eyes for some much needed sissy beauty rest.

A few hours pass and all of a sudden you are awoken. You hear footsteps in the room and realize you are not alone.

You try not to become slightly scared but then a tremendous amount of weight is on you, and you realize a man is in the room with you and is now on top of you.

You try to yell out, but the minute you open your mouth a big giant cock is shoved into the back of your throat. You put up a fight for a moment only to give in to ‘get it over with’.

You look over at the door to see your mistress standing in the door way, glaring at you with a wicked smile…she is, after all, the one orchestrating this whole thing…

This is far, far from over…your mouth isn’t the only thing getting fucked tonight.

 

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Sissy Tracy Needs Pimping

I found yet another victim that gets her little sissy clitty wet when she thinks of getting attention after being whored out by her mistress.

maidFor Tracy’s beginners outting (for those sissies not yet ready for a serious sissy outting), I asked her to send me a few pictures and answer a few questions.  I know she said that she DOESN’T want to be outted…but she read the PPV activity, and agreed to it by her simple response…now Tracy’s fate is in MY hands…and I want to share her with the world! Time to pimp this little sissy whore out!!

Tracy has been dressing since before puberty, dressing in her sister’s and mother’s clothing until she was old enough to go to thrift stores and shop on her own, with her owntracy money.

According to Tracy, going into these stores was a HUMILIATING experience. But, as humiliating as it was, it was a turn on for this little sissy in training.
Tracy lives in Atlantic City, New Jersey. Apparently she likes to send pictures to other people and having the control out of her hands. Makes me wonder just how many pictures are truly out there? and based on how many COULD be out there…is outting her on my blog REALLY that big of a step? I mean…once its out there…its out there forever.

tracy2And once I tweet this blog and a few of her pictures to my 1500+ twitter followers, her pictures will be immortalized in the world wide web.

Oh! And I should mention that this naughty little slut has fantasies of getting dressed up and sucking cock of several random men. She wants to become a cum guzzling, cock sucking sissy slut. (Maybe she will be my next sissy bimbo in a box

Don’t worry your little bimbo heart Tracy, with me…that fantasy will one day turn into a reality. There will be no backing out.

Look at you Tracy! You are now a star~ Now…let’s see what kind of fun I can have over on craigslist with your pictures and desire to suck cock~

Are you a sissy that wants to be outted? How much can you handle?!

Sissy Outting for Beginners: 

Sissy Outting the Next Step: 

Ultimate Sissy Outting: 

 

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Sissy in a Box

I want to play a game with you.

I want you to get dressed up in your sluttiest sissy attire – Head to toe. Get your hair done, put on your make up and make sure to choose the deepest red lipstick you can find. Make your eyes all dark and shadowy.

Your outfit should be short and revelaling. Maybe even putting on some crotchless panties and having a skirt/dress so short it reveals ALL.

That little sissy clit of yours needs to be wrapped up with a pretty, satin pink ribbon that is tied in a bow at the top.

Put on those sexy thigh high, nylons and your highest fuck me pumps.

Im going to treat you like the little sissy whore you are tonight and you need to look the part.

I will be placing you in a box. A box with several holes on the sides and top.

I will invite the big black men with their huge mandingo dicks to slide their cocks into any hole they desire…and it is YOUR job to please EACH and EVERY one. Suck and fuck inside this glory hole box – there will be mulitple cocks at a time, are you nimble enough to bend and contort your body to please each one?

You can back that sissy ass up to one, while your lips are on another…and both of your hands stretched out rubbing two others.

This is going to be a fun game of sissy in a box. You will go in looking like a slut…and come out looking like a cum covered sissy slut.

Doesn’t this sound like a nice cum filled/fun filled evening?

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Want to be an OUTTED sissy?

Are you one of those attention whore sissies?  I would actually be surprised if you weren’t—after all, my stable of sissies – sissy maids, sissy bimbos, girlfriend sissies and all the rest—seem to LOVE getting attention.

There are a few that shy away and only break out those sexy high heels , lipstick and lingerie in the privacy of their own room and locked doors.

But…what if you were outted?

What if your dirty little secret was released to the world? It could be something as simple as someone tweeting your name, or something as elaborate as posting on different social networking sites and contacting those closest to you.

Does that tickle your fancy and have your clitty leaking?

Do you think your family, friends and co-workers would humiliate you and laugh and point..or would they snicker behind your back…or would they just go on about their day to day because all you did was admit to something they all already knew. (perhaps your secret of being a femboy isn’t much of a secret at all)

These are just things that my sissies ponder and I LOVE having the option in my finger tips of outting you. I want people to know. I WANT to show you off.

Sissy Outting for Beginners:

Sissy Outting the Next Step:

Ultimate Sissy Outting:

While Id rather you joined me in outting yourself, I don’t mind forcing it upon you and putting you in situations that will likely leave you blushing and fumbling for the right words to say.

Could you imagine sitting at lunch with a girlfriend or group of ‘guy pals’ and I walk in…sit at the table, and just place a pair of panties on top. Ones that you KNEW belonged to you. I would quickly introduce myself as Lillith, and say I was a close friend of yours and then explain that the panties weren’t mine. Id follow up with the fact that YOU knew who they belonged to and sitting right there, we’d all await your response.

Let’s not forget, I’ll correct you if you stumble and try to fib, and id bring out the pictures I had take to show you in the same panties I placed on the table.

After outting you, Id giggle finish my drink and head out – of course Id be looking forward to hearing about your experience and the conversation that followed.

Have you been outted before my sissy? Is it something that you fantasize about? Leave a comment below, I want to know how you would picture this little rendezvous going down.

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Sissy Lingerie Winners

After much deliberation the mistresses and I have finally determined our winners for the first of our sissy summer series 🙂

For our sissy lingerie competition the winners were as follows:

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In the CUTEST LINGERIE category, the winner is Sissy Mandy with the cutest blue tutu weve ever seen. Loved the smile. I can just picture you twirling around singing Im a little teapot with that little tutu on. Now you just need a teapot and have yourself a cute little sissy tea party!

contestant1-3Tania was determined to be the sexiest of the sissies in the lingerie competition. This one was a stiff one, it was hard to determine just ONE winner in the sexiest category. Lots of sexy sissies running around in lingerie out there. There are a few I want to ask “where did you get THAT from” — may have to add to my own mistress lingerie collection 😉

The Sluttiest Sissy Lingerie was another difficult category and in fact THIS category had a TIE between to naughty sissy sluts! Congrats to BOTH Penelope and Danise for acting like the perfect little sluts when it came to your lingerie! (and there are a LOT of sissy sluts out there, we adored you all! )

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Now being mistresses you know we can change our minds at any given time and with so many entries we decided to add in a different category.

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Congratulations to the Glamorous Sissy Chelsea (won most glamorous sissy lingerie) — Gotta LOVE her sense of style and that pose speaks volumes. G-L-A-M-O-R-O-U-S

Then we had the Overall and Runner up for the sissy lingerie contest. The Overall Sissy Lingerie title goes to that naughty sissy Tania  and the cute, sexy, and slutty runner up sissy juli! (aka pp julie ;)) contestants8contestant1-1

Thanks to ALL of the sissies that entered. It was a ton of fun and I cant wait for more little sissy competitions to follow this one. Be sure to check out this blog or any of the mistress judges’ blogs

 

 

And of course if you get a chance stop by and thank the mistress judges for taking the time to get their sissies involved, and for being involved with the judging. 😉 We all love a little goddess worship and to be thanked for all we do for you all.

These were your judges:

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Have a wonderful day Sissies! And Congrats and thank you to all of our sissy lingerie participants!

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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Sissy Bimbo Slut Training

It’s that time of year sissy sluts and bimbos!

When the sweaters and pants are being put away and the shorty shorts are coming out, the sun dresses, the low cut cowl neck dresses and every other piece of clothing that covers the least amount of skin.

It’s the season of the sissy bimbo slut!

You need to know how to walk the walk, and talk the talk—not to mention look the look.

I would love you in a pair of wedge heel strappy sandals, in a nice floral halter top dress serving my Mistress friends and myself –

It would be perfect to take out my 8 and half inch red strap on and shove it into that sissy ass stretching it for the next REAL man to have plenty of room.

When I have you making cocktails—I will be referring to more than just a fruity alcoholic beverage.

Start your Sissy Bimbo Training today, and share your sissy story.

Justen — Sissy and Tranny Fantasies

Affirmations are something that EVERY sissy should do. When I start my 12 step sissy school camp, they ALL start off with affirmations, but each one has a different SET of affirmations tailored to every sissy’s need. I have said this numerous times but I don’t believe in fitting anyone into a box. Perhaps you are a sissy slut that loves the frills and lace, or maybe you are just a man that enjoys wearing women’s panties but don’t refer to yourself as a sissy. While there may be CATEGORIES you fit into, you won’t fit in PERFECTLY because you have your own individual set of needs, wants and desires…THAT is what makes you perfect, not the box.

I have been enjoying the torment that Sissy Justen has been enduring as of late. Here are her latest sissy diary submissions:

7/15 I did my affirmations this morning when I woke up, when I closed my eyes I saw me putting on girlie clothes in front of a mirror. There were a few girls there, and they were helping me. Today I had a salad for lunch which I was good, there wasn’t anything special about it though. Honestly I was thinking if I was cool with people not knowing this side of me, and I found out that I am, the only person I’m cool with sharing this side of me is my partner whoever they may be a mistress or a girlfriend or wife, doesn’t matter who they just need to be able to accept me for me :)!

Mistress Commentary: It is always wonderful to have that person you can truely, honestly connect with. Be it a mistress, friend, or significant other. I also wanted to add, that perhaps this vision of putting on your finest sissy maids uniform or sexy negligee could in fact come true! I could find another sissy training mistress to watch you, perhaps for your graduation? 

7/16 Today I did my affirmations while my eyes were closed I saw myself as a maid servicing woman and trannies which turned me on a little ;).

I edge after that and didn’t cum. When I finished I took my shower and today I felt like I smelt really good. I went to school then went to a friend’s house and listened to her as she talked about her boyfriend and how he was coming back this week. I don’t like her boyfriend he is a dick but she likes him so I just listen. When I got back I was in the basement with my family watching a t.v. Show and I saw this woman, she looked so hot I wish I looked like her and had a girlfriend, mistress or whoever like her she was amazing :0.

Mistress Commentary: Ahhh A bit of a Tranny Fantasy Huh? We will be having some fun with this one. Nothing more exciting than being able to be with an Exotic woman. A girl with…Something EXTRA. 😉

7/17 today when I got up I saw that my parents were not home so I gathered a pair of panties a garter belt and stockings and went to the bath room. I shaved my legs half way before I took a shower. I hate shaving I am always worried I’m going to cut myself :(. After the shower I put on my panties and other stuff and walked into my room and started doing my homework. After a couple hours my parents came home and I put on some pants over my girl clothing. They left so I took off my pants then I did my sissy affirmations and saw myself as a sissy school girl with long black hair the outfit I saw myself wearing was hot!! I went downstairs after my affirmations and watched a little t.v, after that went up stairs and read a book. Today was a good day, kinda boring but I needed to stay home.

Mistress Commentary: Shaving is a hassle for boys and girls. Mistresses and Sissies. I am somewhat of a masochistic myself and LOVE getting them wax. One day I will go and get the laser hair removal on my legs but we’ll see. As far as nicking yourself…It will happen. It seems to happen LESS with me when I shave using hair conditioner or lotion and then right after putting baby oil on my legs. (there is a nice little sissy shaving tip for you all to enjoy)

7/18 this morning I took a nice long bath, it felt so good. I had my laptop in and had the mp3 for the affirmations and listened to it a couple times. I really enjoy listening to it.

While I listened I saw myself sucking a girls cock while other girls watched, I was wearing nothing but a bra and panties.

It made me get horny so I edged after the bath. After I edged I did a little yoga in my panties the put on pants and helped my parents move furniture so my mom can paint. I went out after and saw skyfall which was boring. I went home and them played a couple video games with my friend and talked to my other friend who went to basic training. Then I went to bed… I have school tomorrow 🙁 I wish I had it off!!

Mistress Commentary: To bad you cant compare notes…His Basic Training to your Sissy Training I bet they can be equally intense physically and mentally. 😉

That was the weekend of Justen and Next week I’ll post her next sissy diary submissions. She seems to be enjoying the training and slowly but surely seeping into this new lifestyle and way of life.

There still is the issue of NAMING my sissy~ I think we have narrowed it down, and the naming ceremony will commence very soon! 🙂