Category Archives: Sissy Outting

Diary Entry: Sissy Waxing, Part 2

My male ego NEEDED that blush.

That was a lot of femininity to absorb and that shot in the arm toward the end helped me recover a little.

There’s of course another possibility–one that is deeply erotically humiliating–but I still suspect my gut instinct interpretation was correct.

My legs and chest feel different. Actually super weird is more apt.

It’s the strangest sensation but I swear I feel like my legs are wet all the time, like I’ve just gotten out of a pool. Does hair soak up moisture or something? Actually I think what’s happening is in the past when dry, the hairs protruded a bit and on contact with something they would trigger the nerve. Previously when getting out of water the hair would be weighed down by the weight of water and pressed flat against the skin, and wind or something else would trigger the nerve. Now without hair, any brush against the skin is triggering a sensation has historically been associated with wet hair and my mind is confusing the two. At least I think that’s the explanation but I’m not sure. I keep reaching down to brush water off my legs but they are dry and smooth. WHAT IS HAPPENING!?

The strangest, most surprising thing I still quite can’t get over though is my stomach. It’s like I don’t even recognize it. I look down but I’m still not quite convinced it’s my stomach and my belly button. I can hardly keep my hands off of it, feeling the smooth foreign skin over and over again.

For the first 18 hours a red bump appeared in place of every single hair that was ripped out.

Jessica assured me those would recede and they did.

I have smooth hairless skin from my neck down (okay, my arms still have some fine hair and i didn’t have my armpits waxed or my bikini line).

While my shoulders are a little broad, I don’t quite have the physique of a masculine male… Not many muscles anyway.

I look feminine with my hairless skin. Dressed, I would look quite feminine. Dressed and from behind I would be indistinguishable from a female. I look like a sissy.

I’m acting and behaving girlier too: getting waxed, chatting about skin care with a pink haired girly girl, shopping for girly skin care products.

I’m acting like a sissy.

Something that’s kind of turning me on too is that the mantras feel different now. They feel … more effective and more real. Something about looking girly and doing girly things and having it repeated in my head is powerful.

I am a sissy.

It’s been a deep, erotic fantasy of mine for more than two decades to have hairless legs and a hairless chest. Always fantasized, never realized. That limit has just always been too far and out of reach. Until now.

My legs, chest and boobs look so much better too.

Thank you Mistress Lillith!


It’s amazing what can happen when all the sissy puzzle pieces fall into place.

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/

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.

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 😉

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!