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.