Category Archives: Sissy Outting

Exposed Sissy: Phyllis Laday

I’ve seen countless pictures of Phyllis Laday – she is a beautiful blonde sissy that looks FANTASTIC in red. You could never convince me that she was EVER a ‘Phil’ – There is not a bone in my body that would ever believe her to be Phil from Northern California.

She will always and forever be Phyllis Laday

The world needs to know of this Sassy, Slutty Sissy – Half would be in awe, the other half will be lining up to get their cocks sucked by her. Many truckers have wiped smeared lipstick off of their cocks from the cock gobbler, Phyllis Laday.


I’m a mature cross dressing sissy in Northern California that needs exposure. I try to pretend to be Phil a strait male in my vanilla life but the fact is I love to make myself pretty from head to toe and enjoy dating masculine men that are into sissies(can’t believe there are so many men into sissies) and having sex with them.

I started out by just posting a few pics of me on AOL and was amazed how many men commented on me and sent me phone numbers and emails and it excited me. There was one local guy I met in a chat room that wanted to meet me real time. I didn’t think I was gay at the time but thought it wouldn’t hurt to try it with a man one time…..wrong. To make a long story short I’ve kinda lost track on how many men have used me and I’ve become an excellent cock sucker and can even deep throat most men.

I’ve met men through craigslist ad, cross dressing and meet up sites.

One of my favorites is getting a hotel room near truck stop and dressing up like a slut and cruising and trying to get picked up by horny men.

I also love adult book stores with video arcades and glory holes.

This kinda scares me as people that know me wouldnt believe I such a faggot and has caused me to purge my things sometimes and try to be a man again but it doesn’t work. I was probably meant to be a Sissy as I have a very small cock and only one testicle and was never very good at pleasing a women anyway.

I’m married, she knows of my cross dressing and not supportive. She doesn’t know but suspects I may have been with men. We are friends, but our relationship is sexless as she is not a sexual person and I’m inadequate in the bedroom. A lot of this has to do with my brain being reprogrammed to my true self as a bottom sissy for men.

I feel I may have become totally gay now.

I only watch gay porn and Sissy hypno vids that are pushing me further.

I want to tell her but not sure how.

Maybe, if Mistress Lillith keeps exposing me I may get caught and have no choice. Most people would be shocked to know I do this and it shocks me also. The exposure scares me but excites me too.

There is no turning back once I’m exposed and I’m starting to see my pics all over the internet so much that it now has me thinking of how I’m going to explain myself.


I love to expose my sissies. It brings them attention and excitement. When I post it on my blog, it is forever. Phyllis Laday knows this, accepts this and is ready to take the next steps into exposure.

She may purge, she may toss her wig and cut up her thongs. She may attempt to erase all trace – and yet, it will always be…RIGHT HERE. Front and center, just like a cocksucking attention whore sissy needs.

Welcome to the spot light Phyllis, I know you love it – and I know you want more.

Exposing Sissy Tara

You may find that woman stunningly attractive. But you aren’t having images of wooing her. Are you? You aren’t picturing being that perfect man in her life. You would much rather walk up to her and strike up a conversation hoping that she notices your fresh set of nails you just had done earlier. You want her to ask you about your nails, ask you about the attire that you have on – did you get a new dress? Who did your hair today? That is a fantastic pair of shoes!

You want to have girlie girl conversations while looking and feeling like a girlie girl. You want to BE one of the girls.

This high that you get from wearing and looking like the perfect sissy – needs to be…permanent. That feeling that you get when women are asking about your mannerisms and about your clothing choices and about your overall sissy style, look and feel – needs to stay. Not just a ‘boring Friday night’ kind of feeling.

For Sissy Tara of Chicago, she is the epitome of what a sissy should be. Look at her poise, look at her grace. She takes time and actually walks the walk. She does live a double life. Wearing panties and thongs under her ‘man clothes’ during the work day and donning lipstick and playing with dildos at night.

On special occasions, she will get herself dolled up and go get profession photos done of herself. Living life as a sissy. Out in the open. Knowing that those pictures may not always stay a secret. Honestly, why keep them a secret? Sissy Tara is FANTASTIC and NEEDS THE SPOTLIGHT. She needs to put on her highest heels and scream from the roof tops that she is a fabulous sissy and loves

being a sissy.

You can tell in the photos how fantastic she feels. She really…opened her self up…in a few of them as she bounced up and down on a bright red dildo.

Sissy Tara is probably one of the most genuine sissies that I have had the pleasure of speaking with, and now the pleasure is all mine to shine that spotlight on her and give her the exposure she so rightfully deserves.

She is around twitter, I know I’ve seen and retweeted her pictures in the past. If you see her pop up, retweet it. Show her off and expose her. There will be no hiding in the shadows, not any more and certainly not for this sexy and fun little sissy.

Show yourself Tara, be a loud and proud sissy!

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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