Category Archives: Sissy Humiliation

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 😉

Impregnating My Sissy

What could possibly be more humiliating than a sissy that was (1) forced into frilly feminine attire and (2) forced to service the big black cocks that mistress makes you suck and fuck and now you find out that you are a pregnant sissy.

Having to endure and go through the motions of a full on pregnancy.

This isn’t what you wanted is it sissy? But you didn’t have a choice.

I ushered you down into my play room and began your daily punishment rituals. I dressed you in shimmering outfits that took your ‘sluttyness levels’ up and beyond. I made you slather your body in baby oil for that smooth, sleek look and feel.

Pulled your hair back and out of your face and applied a deep shade of ruby red lipstick, then spritzed you with a floral/fruity perfume.

You had gotten ready like this before, but something different was in the air. You were getting a little nervous…weren’t you sissy?

Then the real men came in…12 of them. Quite a few for such a special occasion don’t you think?

They took their turns on you sissy. Each one pumping their delicious, thick load of cum inside of you. Riding you raw—

And Each Time I made you stay in the gay ostrich position I had taught you. (head down between your knees, ass up and cheeks spread with your finger tips)

Their cocks were huge, their cocks were thick, and their loads were unlike anything you had seen before.

When they were done, you were forced to remain in that position for several hours until I came back in—

3 weeks later — You know what that special little occasion was all about.

I wanted to impregnate my sissy and that is just what I did. Your belly will swell, your nipples will become sensitive and your tits will grow. MMM…this will be quite a journey for you my little sissy slut slave…You will walk around for a long time as my pregnant sissy.

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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