Category Archives: Uncategorized

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…


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. 

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.

Once a sissy ALWAYS a sissy: Return of Sissy Tracy

There are people that purge their sissy attire because they feel as though they can rid of it once and for all, and never again go back to their sissy loving ways.

That is wrong…you will ALWAYS come back…you cannot escape being a sissy.

I often tell my sissies to fight the urge to purge because a sissy purge is always so drastic and always so expensive later on – because you will want it back, and will have to start your collection over.

I don’t know that this particular sissy purged anything but, I have exposed this sissy a time or two in the past and a few years later here she is being exposed again. This time in a full sissy exposure kind of way. Why? Because once a sissy, always a sissy.

At the time Sissy Tracy didn’t want to be exposed but followed the rules of the exposed sissy assignment and was ultimately exposed.

If you want to read her old post from 2014 check out Sissy Tracy’s Exposure.

And here we are…3 years later…and Sissy Tracy is just a feminized as ever.

“I am a crossdresser, to the point now that I cannot think of anything else most of the time.  I love looking at pictures of feminine women all dressed up….especially anything vintage and pin up related, and I imagine myself like that.  Women were so much for feminine and dressed like it all the time back then.  Almost every waking hour I am thinking of dressing up and acting like a woman….with all mannerisms like posing with bent wrists.  I even dream of going all the way with acting out as a woman by meeting with men and 

sucking cock to make me feel as feminine as I can.  “

She has zero fear of being exposed now, but it seems as though it is time to rev up her sissification and feminization journey. She already walks the walk and looks the look…it’s time for her to find a real man to treat her like the sissy slut she is. Who wants to lend their big meaty cock to this sissy slut for you to show her your moves?


Say hello once again to my Sissy Crossdresser from New Jersey. She’ll be on craigslist if you want to find her and give her a taste of your scrumptious cock.

Pop Sissy Kelly’s Cherry

Time to pop a new cherry on an exposed sissy!

The best thing about exposing sissies is that once their information is out there on the world wide web, even if for just a few moments – it can be out there forever. From people right clicking and saving to use it themselves, to it being saved on the wayback machine and internet archives. You just never know.

Some sissies like being completely exposed, while others want to hide in plain sight. I think Sissy Kelly is one that likes to hide in plain sight. Those that are closest to her could tell the body type, and would just KNOW.

I have a feeling that Sissy Kelly is one that people wouldn’t be surprised if they discovered her naughty little crossdressing secrets. Just one of those people that you KNOW something is off…so when it is all exposed, they have an ‘ah-ha! Told you’ kind of moment.

“I am sissy Kelly.  I have been wearing women underthings cent I was (of a very young age). I started with my mother’s and sisters panties. I live in Clinton, Tennessee.  I want to be outted so am forced to take that next step in being sissy and pop my cherry”

As a girl who loved her panties I always knew if a pair went missing. Im willing to bet mommy and sister knew you were perving through their panties and wearing them. Makes me wish I could be a fly on that wall to listen to the stories they had about you!

Well Sissy Kelly, your cherry is sort of popped. We would consider this a ‘finger banging’ kind of sissy exposure. Why not take a bigger step into the spotlight. I think I pulled your email and phone number. Guess I need to go onto craigslist and post all of that info and see if someone really IS willing to pop that sissy ass cherry!

Free Sissy Task

I don’t do free sissy tasks assignments very often…so when I do, you need to complete. Doing so tends to inspire me to possibly  put more free sissy tasks out a little more often.

And besides, it is the holiday season. So … Enjoy ~


I am doing a compilation video of 12-days of sissies. You can take more than one day but, no more than 3.

~This assignment requires that you record a clip, that shouldn’t be any longer than a few seconds.

~No Nudity. You are a sissy. You should be dressed up 😉

~Id prefer you in panties or with lipstick on or completely dressed in the clip — but you do not have to show your full face nor have any distinguishing marks that would identify you.

~Look up the tune of 12 days of christmas and you’ll know the tune to sing your line in.

Once I’ve received all the submissions I will organize them into the full song and post it on my sissy site, and a link to it from twitter — I will send you the video as well.

DEADLINE: Once I give you your line(s) you will have 2 days to get the recording back to me before I reshuffle the line back to assign to others. This assignment is only good until December 10th, then no more submissions accepted 🙂

Please feel free to send me a message if you have any questions or for more information or if you would like a line or two to record. (If you tell me a short summary about you I can give you a line that is best suited for your personality)

You can send me a message on Niteflirt, Skype: mistress.lillith or send me an email madamerotic @ gmail for your lines and how I want it done.

I don’t put free sissy assignments out often so enjoy it while it lasts. 😉 If you want other sissy assignments sign up for sissy training. Yes this particular assignment involves a little bit of exposure but it’s minimal.


RIP Michael Burdick, Long Live SISSY SLUT JESSICA

Michael Burdick needs to be exposed for the cock loving, red lipstick wearing sissy slut he is.

It would be a fair assessment to say that a good majority of sissies want to be exposed.

They want to be exposed and they want the world to see them for what they really are. They want people to KNOW they are a sissy. They want people to KNOW they enjoy dancing around in sexy lingerie and putting on layer after layer of creamy red lipstick.

I love my sissies and I enjoy nothing more than fulfilling that ‘not so secret’ secret wish of theirs. You could ask any one of my sissy trainees and they will tell you its something I take a great amount of pride in.

(I have a sissy hall of fame where I post pictures and their stories and it remains up there…permanently)

Michael Burdick of New York is Sissy Slut JessicaSissy Jessica is a sweet, and fun loving sissy that I have been working with and training for almost 2 years now. With it being 2016 and everyone in the mood to have some new year’s resolutions…I think it’s time for Jessica to kick her training up a notch.

Michael, the wannabemale, regularly likes to deny Jessica the right to live life to the fullest. He wants to hide and sneak away whenever he gets the opportunity – all the while keeping Jessica locked away. Jessica wants to come out and play, and let’s face it…I’d much rather play with Jessica than that silly cock sucker Michael.

Its time to ruin Michael Burdick to the point he will be FORCED to live out the rest of his days as Jessica.

I have made up some new rules for 2016 for my sissy Jessica, I’ll share 3 of the 10 –

  • Every time I am online she is to rub that clit and think of Jessica getting bigger, and Michael Burdick getting smaller
  • There will be a weekly craigslist/public posting talking about Michaels life and transitioning to Jessica more full time
  • I will send her music video, song, etc that she will be required to dress and choreograph and dance for me…have THAT recorded and placed on the youtube channel that I will be setting up just for her. (It will be my youtube channel, so that she can’t go in and delete it…ever)

This is going to be a fun year of exposing sissies and this is shaping up to be a great year for Jessica. Perhaps not so much for Michael.

RIP Michael Burdick – Long Live Cock Sucking Sissy Jessica!

Sissy Lingerie Winners

After much deliberation the mistresses and I have finally determined our winners for the first of our sissy summer series 🙂

For our sissy lingerie competition the winners were as follows:


In the CUTEST LINGERIE category, the winner is Sissy Mandy with the cutest blue tutu weve ever seen. Loved the smile. I can just picture you twirling around singing Im a little teapot with that little tutu on. Now you just need a teapot and have yourself a cute little sissy tea party!

contestant1-3Tania was determined to be the sexiest of the sissies in the lingerie competition. This one was a stiff one, it was hard to determine just ONE winner in the sexiest category. Lots of sexy sissies running around in lingerie out there. There are a few I want to ask “where did you get THAT from” — may have to add to my own mistress lingerie collection 😉

The Sluttiest Sissy Lingerie was another difficult category and in fact THIS category had a TIE between to naughty sissy sluts! Congrats to BOTH Penelope and Danise for acting like the perfect little sluts when it came to your lingerie! (and there are a LOT of sissy sluts out there, we adored you all! )






Now being mistresses you know we can change our minds at any given time and with so many entries we decided to add in a different category.


Congratulations to the Glamorous Sissy Chelsea (won most glamorous sissy lingerie) — Gotta LOVE her sense of style and that pose speaks volumes. G-L-A-M-O-R-O-U-S

Then we had the Overall and Runner up for the sissy lingerie contest. The Overall Sissy Lingerie title goes to that naughty sissy Tania  and the cute, sexy, and slutty runner up sissy juli! (aka pp julie ;)) contestants8contestant1-1

Thanks to ALL of the sissies that entered. It was a ton of fun and I cant wait for more little sissy competitions to follow this one. Be sure to check out this blog or any of the mistress judges’ blogs



And of course if you get a chance stop by and thank the mistress judges for taking the time to get their sissies involved, and for being involved with the judging. 😉 We all love a little goddess worship and to be thanked for all we do for you all.

These were your judges:

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Have a wonderful day Sissies! And Congrats and thank you to all of our sissy lingerie participants!

Sissy Bimbo Slut Training

It’s that time of year sissy sluts and bimbos!

When the sweaters and pants are being put away and the shorty shorts are coming out, the sun dresses, the low cut cowl neck dresses and every other piece of clothing that covers the least amount of skin.

It’s the season of the sissy bimbo slut!

You need to know how to walk the walk, and talk the talk—not to mention look the look.

I would love you in a pair of wedge heel strappy sandals, in a nice floral halter top dress serving my Mistress friends and myself –

It would be perfect to take out my 8 and half inch red strap on and shove it into that sissy ass stretching it for the next REAL man to have plenty of room.

When I have you making cocktails—I will be referring to more than just a fruity alcoholic beverage.

Start your Sissy Bimbo Training today, and share your sissy story.