All posts by Lillith

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. 


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

Diary Entry: Sissy Makeup Musings

What is happening to me?

After chatting with Mistress Lillith and prior to bed, I put on a pair of panties, played my sissy mantras on my headphones, and began watching the makeup tutorial videos she had referenced in her email assignment.

My smooth hairless skin, the panties gripping tight, training mantras on repeat softly pounding into my head, suddenly a cute girl discussing how to put on makeup–but nothing sexual-focused, no erotic suggestions. Just makeup. And damn I was turned on. Makeup has never been a thing for me. Not even close to getting aroused by it. I mean, I’m not one of those “beardo sissies”, but it was always more of a slight curiosity if anything.

Last night it became eroticized. 

The thought of painting my face, along with the rest of the changes taking place… staring into a mirror and looking myself literally in the eye as I made changes.

Sending pictures before, during, and after… of my face. Would I be humiliated to a large lump in my throat with the makeup? Or would I smile? I think I’d smile, but there’s a (small) chance otherwise…

Sometimes it’s hard to step outside of oneself and have awareness of what’s happening. The mirror and pictures would help bring the changes more closely into focus. This would be harder to compartmentalize. This would be pretty gay by almost any standard.

I reached out to Mistress Lillith and asked, begged almost, to train me as a sissy and teach me to serve as a submissive. “Not fantasy,” I said, “I’m looking for more of a real Mistress experience.”

Now on week 3 we are approaching areas I haven’t really explored before (well, maybe a little here and there 🙂 . This isn’t a limit being approached, more like a fertile untapped area for exploration. It’s exciting. And scary. Fear can be hot.

I’m not sure what is turning me on. (Mistress Lillith will probably roll her eyes at that statement!!) I don’t think it’s the makeup, but I’m not sure anymore. I think it’s the power exchange, but that doesn’t necessitate the sissy fetish. So there must be more.

I feel like a shy blank slate. I’m glad an experienced pro domme like Mistress Lillith is there to guide me through this experience!!

Breaking my sissies and submissives down to the point that they know longer know WHO they are is something I enjoy. Because then they ARE like a blank slate. Only those that wish to truly be broken down will though, this sissy of mine I have become very fond of, very quickly. Untapped potential and areas of exploration are a delicacy in the sissy trainer world. Sissy Exploration is desired by the sissy in training and the experienced sissy trainer – limits sometimes shift and get broken down – and what blooms from that?

Only time will tell.

Diary Entry: Craving Attention

Speaking as a submissive, a few simple words from a Mistress, or focused attention on a sub–even if for a short period of time–is an amazing experience. The communication is evaluated, each word’s meaning taken by itself and in the larger context. Often the communicated ideas become extrapolated in the submissive’s mind and a wonderful fantasy builds out from there.

I do as I’m instructed. I work on my sissy diary, I try and keep Mistress Lillith well compensated. I listen to my mantras.

Arousal grows, and soon I can barely contain myself. 

“Let me check my Niteflirt again to see if Mistress Lillith sent anything,” I think. Check – nothing. “Okay, maybe I’ll check again in another hour.” Nope. The cycle repeats. Alone with my diary, mantras, and thoughts I continue to plod along dutifully.

“I really need to be tied down and spanked… hard and fast until I cry,” the thought enters my mind. It sounds so thrilling now. It will be decidedly painful during. Afterwards will be a blissful subspace of total power exchange where I know my dom has been really focused on me.


Maybe the reason some subs act up and “stir the pot” is… for attention? Attention from a dom is incredibly satisfying–even if the mechanism for attaining attention is like a child throwing a fit. I mean, it’s a bad, unhealthy habit for a sub but sometimes it illicit a challenge-rebuttal type response and so it gets employed again when the urge grows.

As I reach the end of this diary entry here I am focusing on *my needs* as a submissive. Which is sadly sort of the opposite of what I think I should be doing.

Does an ideal sub have needs? I don’t know. Am I pleasing Mistress Lillith? I don’t know. I am lost without my dom, my only known guidance to dutifully continue with the last instructions I received. \

And then it comes. My breathing becoming short, my heart rate quickens, my hands and legs tremble as I click. The world grows larger and blissful subspace ensues.

The cycle renews.

Anticipation grows within my sissies and subs alike, as I grow your need to be feminized as as you walk the feminine walk, you find yourself becoming super charged with emotions and hormone driven ‘teen like’ sexual angst. Behave and steady yourself, above all…


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 Diary Entry: Mantras

*Continuing with the sweet musings of my Sissy In Training ~ One of her first tasks was her mantras, listening to , memorizing them and REALLY living and feeling them **



The excitement of contacting Mistress Lillith and fantasizing about playing with and serving her messed up my sleep cycle a little bit. Multiple orgasms helped me calm down and relax some. Sleep returned eventually. Sleep is sometimes better then sex, but not always. Hopefully I’ll build up some tolerance to this!

Thinking about her post on being a Head Mistress, I logged on to my Niteflirt account and cleaned up my inbox, my favorites, and my chat history. There’s only Mistress Lillith now. In the featured listing section was a domme I had not noticed before. I clicked on her page and there were some amazing looking erotic hypnosis goodies that I had the urge to buy. Nope. A pleasurable wave of erotic humiliation fell over me as I thought about being denied, being trained… being owned and kept.

The Sissy Slut Mantras are fun. Soft, sweet whispers. My favorite are towards the end of the track:

I am a sissy. 

Being a sissy is my true self.

I will embrace my true self.

Especially the “I am a sissy” one. There’s something about the inflection and the tone.

I’ve listened, as instructed, for around an hour a day (sometimes more, sometimes less, always more than 20 mins) every day since they arrived. With one exception I’ve also listened, as instructed, before falling asleep. The one exception was as a background track while doing something else. But… thinking about a retweet on her twitter:

“If at first you don’t succeed, try doing what your Mistress told you to the first time.”

So now I listen before or while falling asleep (or while taking a bath, but I don’t take baths).

Twice I listened while wearing panties. The second time I fell asleep with the mantras still playing in my ear. I awoke incredibly horny. Laying on my back I spread my legs and began rubbing myself through the panties with my palm. Waves of pleasure crashed over me as the arousal built. I pulled up her Niteflirt profile picture and stared into her eyes. Faster. Soft moans of pleasure. She looks right at you, the subject of the picture not an object–in control. So much dominance, and lust. The words “Mistress Lillith” on my lips at climax, my panties soaked.

I’ve had many go through training and many that start with decent blog entries, so far, this sissy in training has had the most thoughtful responses thus far. Let’s see if she can make it through the bulk of her training or better yet — all the way until the end. 

There is a method to my madness…it is to build a foundations. Sissies like to purge, and while that is another post itself, my goal is to build a foundation so when the inevitable purge happens, and you inevitably go BACK to your sissy self (you’ll never purge indefinitely, you will always go back) – you’ll have your foundation to build from. It wont all be lost. The Sissy Mantras are the first step in building an unbreakable foundation. 

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.








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

Diary Entry: Getting Trained as a Sissy

*This entry is from one of my newest Sissy Camp Trainees* 

This past week has been filled with intense eroticism. I’ve savored every written word from Mistress Lillith. Reading and soaking them in over and over again.

“[Just] like I’ll have your sissy ass worked with a dildo at some point ;)”

My mind ravenously extending the idea into a full blown fantasy, building on the suggestion and filling in all the missing details. In one instance a cam session at my house. Another, Mistress Lillith in tight red latex is standing there next to me. A slow motion video with me as the protagonist plays on an endless loop. Orgasm… The mind is the most powerful errogenous zone.

“…if you over step a bounds or are in need of discipline…I never shy away 😉 you will find yourself learning how to treat and respect a Mistress.”

Thoughts of the impending loss of control, and in some instances, the present loss of control, overwhelm. Drifting slowly into sleep and twitching back out again as I hear a mantra: “I am sissy… I enjoy all things feminine…” “Oh my gosh I’m being trained!” The thought jolts into my head suddenly like something akin to panic.

These are deep, powerful emotions of lust and eroticism being drawn out after a lifetime of being largely unfulfilled.

How can I serve Mistress Lillith? I can be obedient and respectful. But is that really adequate compensation for the experience she’s giving me? Anyway, that’s more the process of serving, not actually serving itself. Our setup does not faciliate physical servitude. I can’t clean her house or mow her lawn, and if I could–creepy factor aside for a moment in this fantasy–it’s still nowhere close to proportional for her unwrapping these deeply held, occasionally repressed, incredible feelings inside of me.

And who is enjoying this more? No doubt a lifestyle pro domme like Mistress Lillith finds some mild enjoyment or amusement in this. How else can one explain the photo shoot in a corset and Darth Vader helmet? She also may be more callous to the novelty of it all. I mean there are probably thousands of Niteflirt subs–all with one thing on their mind–and all who act and behave almost exactly the same. She’s seen this before. Again, who enjoys this more? Let’s just say our play together is almost certainly not borderline changing Mistress Lillith’s sexual identity!

What is the best way to serve Mistress Lillith? Money is the best way. It allows me to pay to have her lawn mowed, or have her house cleaned, or whatever else *she needs*. It allows me to be a useful, helpful servant. I will be obedient and respectful and always pay well for taking up any of her time, and to express my gratitude for her offering me an opportunity to explore this kinky lifestyle and introduce me first hand to femdom.

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!