Tag Archives: feminization training

Diary Entry: Sissy Bottoms Should Never try to Top

During week 2 of Mistress Lillith’s training she had something come up IRL that rightly required her attention. They were a difficult 7 days for me. I was new to her training and felt like I needed a lot of instruction, boundaries, a lot of structure. I remember watching several videos of female subs being flogged by dommes and other tops (most subs are females, it now occurs to me). Strangely, it had a deeply soothing and reassuring effect on me. I vividly remember watching some of these videos and reading about d/s relationships and thinking “I just need to wait patiently for my Mistress.” But this was all being created in my own mind and I actually have little experience with this type of relationship and so doubt crept in.

How should I be behaving?

In week 4, after completing a particularly arousing assignment, I lost my composure. I was pining hard for Mistress Lillith. She is more experienced than I am and has a better understanding of our relationship and what is objectively happening.

I am less experienced and it’s easier for me to confuse our relationship and get carried away by some of the most powerful feelings a person can experience.

I had expectations and made demands of Mistress Lillith.

I think my reaction was a typical pyschological one. But it was not acceptable for a sissy bottom. And I have goals to be a better sissy bottom.

“You are the submissive. I am the Mistress. You came to ME with a need. Follow my lead. Period.”

Yes Mistress. It’s what I needed to hear.

“You belong to me.” “I’m okay releasing you should you feel the need.”

Ownership. Consent. Thank you Mistress.

OMG Mistress Lillith sent me a personal video too (what an amazing domme!!!).

“I am your Mistress. You fucking belong to me. You want to be my bitch? You want more of me? I hope you’re ready.” “You serve me. Not the other way around.”

Yes Mistress.


Sometimes when a newer sissy is going through sissy school and training with me, they will have new and intense feelings that will overpower them. Think of renewed hormones, thing of that teenage angst. It is very similar to that.

Yes, it is important to understand that Dommes, Mistresses, your Sissy trainers, they are people too- there are lives that we have and live outside of our sessions – be it online or in person.

While the feelings can be very intense, and you can have a very strong connection with your Mistress – and right then and there she may be your whole world – understand there is more to the picture. I don’t always share with my subs and sissies the ongoings of my personal life – in this instance I was taking care of an elderly family member that had been hurt. Why do I share this? Simply to say – don’t act as though you are the center of the world or the one and only thing that she is focused on. You could actually damage your relationship with your Mistress by making demands and assumptions.

Here, this sissy was learning. Im slow to anger and adore this sissy – she just needed some redirection.

I am the Mistress, I am the Sissy Trainer, it is I who will be obeyed and I who make the demands. NOT the other way around. 

Sissy Hygiene Check

Reminder to my Sissy Girls Regarding Sissy Hygiene 

There is always a special way that I expect my sissies present themselves whenever I summon them. Some have specially selected ceremonial outfits, and others have a variety that change.

Then again…there are still those in training that are expected to come to me in nothing but a pair of panties and stockings.

Reason being: Hygiene check

You want to be a sissy girl right? Therefore there are certain standards that you must abide by in order to receive the privilege of labeling yourself as one of Mistress Lillith’s sissies.

I LOATHE when boys claim they want to be a sissy, and be trained and turning into a girl, and can’t follow simple steps like hygiene and cleanliness.

What does Mistress Look for?

~NO HAIR—No hair on your legs, chest, arms, face, or groin area. Hair on your head is fine, but nothing unsightly. If you are one of those hairier boys…you’d need to shave or wax your back, neck and ass as well. I DON’T want to see hair.

Its funny how much of a fuss some silly sissy sluts make over having to shave. But, that is where you make your intentions known. Either you want to be a sissy, or you are just playing dress up.

~A smooth finish—Use baby oil to lube up your newly smoothed skin to make it shine and sparkle

~Fingernails—cleaned, polished, kept. They don’t HAVE to be long, and I don’t always require nail polish. Hopefully if you are training with me, you understand the difference between polished nails and nail polish. You need serious training my dolls, if you do not.

This is is among the many things Mistress Lillith looks for when training sissies.

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!

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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