Category Archives: Sissy Outting

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 😉

Exposed Sissy Crossdressor

Having been a sissy creator for as long as I can remember, and having done it professionally for a number of years now – I always find it fascination when I see some sissies, and expose some sissy crossdressor

exposed sissy christinaBy day they walk around, A-type personalities, rough and rugged. They have deep booming voices and strong macho type personalities.

You could almost say that they are the masters of disguise – or perhaps sissies of disguise.

I say sissies of disguise because their outward appearance is just a façade. Their day to day actions are the real disguise.
The minute they get home and undo that tie – they slip into something a little sexier. A little more feminine.

That burly man you work next too, or you see at the store…is really a sissy crossdresser. Just like Christina here. You can see that masculine mustache but is anything about what she wears masculine? HAHA absolutely not.

sissy bimbo slut exposedIt is fun to reveal and expose not-so-manly, manly, sissies.

Just like Christina stated:

The secret I would like to reveal is that I am a sissy crossdresser. Not this super manly man everyone thinks I am. I love high heels, makeup, nylons and other girly things.

I am a sissy boy who likes to dress up as a bimbo.

And Christina certainly isn’t the exception to the rule. The longer I train sissies, the sissies I expose and uncover – the more I realize this is the NORM. ~or not…normal is so vastly underrated anyway.

Seasonal Sissy: It’s time to come out

Winter is fleeting and Summer is Coming. The flowers are starting to bloom and the weather is warming up. The short shorts are coming out and those itsy, bitsy, teenie-weenie, little polka-dot bikinis.  Suddenly you are getting that all too familiar itch.

You can’t walk through a department store without gazing over to the swimsuits and bikinis, or drooling over the cute, floral summer dresses, and then of course, there is the lingerie section.

Spring is the time of the sissy, to begin her feminization journey once again…and summer time is when you really get to revel in it.

I can just picture your palms starting to get sweaty, your heart starts to race, and that little clitty of yours starts to leak. It’s your favorite time of year.

During the winter, you think you can just box up your feelings. Sweaters and jeans help you to conceal your sissy desires – but now it’s too warm for sweaters, and the legs are begging to come out…and guess what? SO ARE YOU!

Your desires find you rushing through the store, back to your care to drive home as quickly as possible—hoping no one is home – all so you can rush to her panty drawer grab several, put them up to your nose and inhale deeply.

You fall back onto your bed, panties thrown all over your face as you sniff them and close your eyes picturing the days of summer

It’s time to get back to your sissy self, time to go shopping, time for a makeover…It’s time to come out!

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 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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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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