Category Archives: Sissy Humiliation

Exposed Sissy: Roy Bourne aka Sissy Diane

One of the exciting things about being on sissy diaries and being exposed – is that it’s permanent. There was a time that I would take things down if asked nicely, but not anymore. You asked for exposure – and that is what you get exposure.

Now, we get to learn about Sissy Diane. We will be getting to know her together as we start HER sissy exposure journey, but – any sissy that wants to play in the sissy spotlight, is FUN by my standards. 😉


Roy Bourne - Sissy Diane

Roy Bourne is from Tavistock, Devon in the UK. Sissy Diane is her true identity. I always view the masculine name as the mask – with the sissy name being your TRUE self. It is interesting to me how many sissies are married to someone that doesn’t know, or acknowledge or accept their sissy lifestyles. In this instance, Sissy Diane says, her wife doesn’t know. Roy Bourne - Sissy Diane

“I have hidden away for years as a closet sissy I am on Internet.

I love exposure and humiliation

I want to be exposed by you so I cannot comeback and remove my exposure.

I love dressing and wearing make up. I am also into bdsm

I love bondage . Impact play . Forced feminisation .

I love sucking cocks and receiving anal which I have done a fair bit in past with fellow sissies and crossdressers .

I am totally submissive and a total bottom man.

Secrets I hide nobody really knows what I have done or do regards crossdressing at all other than people I have spoken to on various sissy sites i.e. Tumblr twitter etc.

I get a thrill from seeing my pics on internet .”

Roy Bourne - Sissy DianeThe internet is forever Diane. Even when posts and pictures are removed there is no telling who saw or if someone right clicked and saved. There are archives that save these pages as well and so nothing is fully removed.

Its fascinating how many exposed sissies there are on the internet. They hide in plain sight and yet are rarely seen by those closest to them.

Well, it’s out. You are exposed. No longer REALLY in the closet unless you view the internet as a giant closet. Someone could find it if they looked just a little 😉  This is just the beginning my dear.

 

Exposed Sissy : Paula Jones and her Sissy Journey

Exposing sissies is one of my favorite things to do. I adore reading their back stories and I love posting and furthering their exposure. To me it can start with the back story – but as any of my sissies know…I take it sooo much further than that.

Say Hi to Sissy Paula – she submitted a diary entry to be posted.


Hi my sissy name is Paula Jones real name Paul Greenwell.

My sissy journey started late in life, I was a happy married guy- my wife was good looking successful and we had a great sex life until I was away on business and I was in my motel room looking at porn on my laptop.

I honestly didn’t even know what a sissy was until that night I did dress up once or twice when a teenager but it didn’t turn me on as much as the hot girlfriends I was lucky enough to have back then -anyways back to my story I came across some sissy hypno videos and I was instantly hooked.

NOTHING had ever turned me on like this before that night. I ordered over $1100 worth of clothes, wigs, breast forms, all with express post. Once they arrived to my Po box I started spending a lot more time at my office after hours.

I shaved my whole body and started taking picks and making videos of my self jerking of in my women underwear with make up on and a wig. The breast forms I had were E-cup and huge.

I was watching sissy hypno all night long I got in-touch with an online mistress and that was the start of my demise she instructed me to get a tumbler page and start posting my pics.

This all happened over about 3 months.

My wife by this stage was thinking I was sleeping with someone else and decided to spy on me she came to my work and to her total shock and horror caught me dressed like a cheap slut jerking of to sissy porn. She didn’t say a word. She left me the very next day and hasn’t spoken a word to me since. I didn’t try to contact her at all.

By this stage obsessed with sissy exposure.

I’ve tried to stop so many time I always end up doing it again and each time it’s worse than the last time I’ve paid thousands to online mistress and lately masters aim out of control can’t get enough exposure.

I’ve bean with a couple of men and a few sissies over this ten year journey. Im so deep into exposure that I use my real name on every pic and video I post.

It is only a matter of time before friends and family find out that I am a sissy.

I don’t know what I will do when that day comes that’s my story.


Sometimes we don’t know what it is that makes us tick until we just happen to come across it one day and it just clicks. No rhyme, no reason – it just feels right, it’s fun, it’s exciting. One thing the internet has been good for is having all sorts of fun fetish videos out there that people watch and learn about the kinks and lifestyles of others. Perhaps it was the sissy hypno clips Paula watched that turned her into a sissy. But, I have a distinct feeling that this was something in her all along – they hypno just brought it to the forefront and Paula learned what ‘IT’ was.

Thanks for your sissy diary submission Paula!

—-

Who is next to be exposed on sissy diaries or engage in exposure with Mistress Lillith?

 

Exposed: Sissy Jessica wants to kiss and tell

It has been quite some time since Sissy Jessica was exposed on my websites. She is certainly already exposed everywhere else. When she is feeling her best she unlocks her youtube videos and has them show up. It doesn’t take long for them to be found in search engines. Even I have looked and found them.

It is always comical to me that she has to sneak away while at work to put on layer after layer after layer of red lipstick. Red lipstick is Sissy Jessica’s favorite. The smooth, creamy texture.

The more lipstick she has on, the more sissified she feels.

But, the REAL fun happens when she starts to rub that little clitty. Sneaking little touches here and there.

 

Michael Burdick likes to hide Sissy Jessica, BUT, once Michael Burdick starts to rub – she loses what little control she had.

She keeps adding layers of lipstick, she keeps rubbing her clit stick – I wonder what her coworkers think about her many, many trips to the bathroom throughout the day. She is usually in there for quite some time- kissing or licking toilet seats, making little recordings, doing whatever I tell Jessica do.

Sissy Jessica LOVES little tasks.

This most recent interaction with her—she let some fun information slip on out.

I love when my sissies are on such a high, and feeling such a rush that they start to reveal even MORE secrets to me.

 

I’ve always known that Sissy Jessica loves to suck cock. She craves a thick meaty mushroom head and a long vein-y shaft to be slammed into the back of her throat. She is a complete and total sissy slut.

BUT, she was looking up something more deep and sensual this time.

She wants to kiss a man. Long, sensual, passionate kisses that moisten women’s panties when they watch it on the big screen.


“I want to make out with a man while I rub his cock.

I want him to kiss my neck and nibble my ears while I stroke him.

I want to feel his hands all over my body as I suck his cock until he’s hard.

He throws me down on my back and lifts my legs so he can kiss me while he fucks me

Kissing my lips and neck as he pounds my sissy girl ass.”


It would seem as though Sissy Jessica has been romanticizing Pretty Woman, but is breaking the rule of ‘No kissing on the lips’ – She doesn’t just want to suck and fuck…she wants a more intimate connection with a man.

Sissy Jessica is a slut that is wanting to be tamed by a strong male – one that can treat her like the whore she is, and kiss her like a dime store romance novel.

Hey, I don’t blame her. I know all to well the ecstasy I feel from passion, lust, and desire. Sometimes you just want to suck and fuck –

other times you want to feel them in you in more ways than physical.

~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*

Want to see some of her past exposure? Sissy Jessica was first exposed August 27th, 2014. She has always loved her sissy red lipstick, 4 years later, she is still obsessed.

 http://www.sissydiaries.com/this-sissy-loves-red-lipstick/ 

 

Then we tried to say goodbye to Michael Burdick once and for all January 6, 2016

http://www.sissydiaries.com/michael-burdick-is-a-sissy/

Sissy Crossdresser April Exposed

Many sissies crave exposure, for me…it is only fun with PERMANENT exposure. That means YOUR pictures, YOUR story, YOU are placed on my blog or website indefinitely. No going back.

Today we have Sissy April ~ always and forever an resident of Sissy Diaries. She needs exposure – constant exposure. The more that see her, and spread her story – the more she will understand that there is NOT going back.

The internet is forever, and so is Mistress Lillith’s Sissy Exposure.

Word from Sissy April: “I am seriously addicted and conditioned to love my sissy crossdresser exposure that I can only cum by being exposed while wearing panties, stockings bra, slip, heels and either a nightgown or skirt”

Sissy April was formerly known as Thomas M  Cozart from Wilson, NC

She loves the feel of her nylons covering and caressing her legs. Getting all dolled up is the highlight of her day – and anytime she is exposed its like Christmas all over again for her. She loves the feeling of being exposed ESPECIALLY as she sees her exposure WHILE she is dolled up and enjoying her sissy self.

Her ex-wife likes to keep tabs on her, so this is Sissy April also saying ‘HEY! I’M STILL A SISSY’ – She wants the world to know. She wants her ex-wife and boss to know too. Why not send them an email:

Exposure is a sure way to fully accept your sissy lifestyle. The more you are exposed, the more it is embedded into you as something that you will NEVER be able to backpedal on or change –

Perhaps you have seen the many re-tweets of Sissy April – from Mistresses like myself, and even other sissies are having fun exposing her. Go and follow: @sissycdtv – find my tweet and others and tweet them out 😉

You could also grab this link and email it to Sissy April’s boss and wife. (Just click on the emails below and a box will pop up for you to send a message 😉  )  Show the pictures, start the conversation – well keep it going that is.

FOREVER AND EVER

 

 

 

 

 

 

Do you want to be a permanently exposed sissy on my blog? Give me a call or shoot me an email 😉

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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