Category Archives: Sissy Training

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.

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.

How should a Sissy Masturbate?

How should a sissy masturbate?

That is kind of a funny question isn’t it? Perhaps the question shouldn’t start out as HOW, but rather, MAY a sissy masturbate.

I would say first and foremost you would need to obtain permission before any sort of self pleasure. Most mistresses and sissy trainers will have you under lock and key, having that sissy clitty locked away in chastity, others will have you on a strict cum restriction schedule.

BUT,

SHOULD you actually earn permission – there is a special way that sissies should masturbate.

Guided Sissy Masturbation with Mistress Lillith
Guided Sissy Masturbation with Mistress Lillith

You need to make sure you are dressed in the proper sissy attire. Your lingerie, your sexy little chemise, whatever puts you into that sissy subspace. You don’t get to stroke like a ‘mans-man’. You aren’t a man.

You must add extra layers of lipstick to feel a little more femme, a little more sexy.

Put on some music that makes your hips sway side to side. I want you to really take your whole sissy self in by examining yourself – head to toe in a mirror.

Now, when it comes time to enjoy yourself and engage in some sissy masturbation, you should know that you don’t get to clasp your hand around that sissy cock and stroke, oh no.

You treat it like the sissy clitty that it is and you masturbate just like a girl would. Using your fingertips and going in a nice circular motion right on that clitty.

That is just the start of it. Of course, it is preferable that you only engage in sissy masturbation with your Mistress or Domina. Obviously she will give you further instruction as to how to get to that edge and spew that sissy spunk if you are permitted to do so.

Remember, you are a sissy. You are a girl. You must masturbate like a the sissy girl that you are.

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!

Sissy Lingerie Competition

Lingerie Competition - Sissy Dressing Contests - Mistress Lillith - www.sissydiaries.comI love sending my sissies through my sissy training camp. Being able to aid you in your fem chic journey is something that excites me and puts a smile on my face.

If there is one thing I know about my sissies, is that they LOOOOVE competitions—they love the attention from it, and the idea of being crowned TOP SISSY and the adoration of other sissies and mistresses alike.

This little competition will be fun and sexy, just like some of my best bimbo sissy sluts like!

So what kind of online sissy competition is this one?

~This round will be a Sissy Lingerie Competition~

Grab your sexiest, sluttiest, or cutest lingerie get all dressed up like you are dressed to impress (impressing the mistress judges, or like you are dressing to impress that sexy big black man with his delicious big black dick)

Get a few snap shots or show of your sexy sissy self on cam for myself or any of the judging mistresses.

How Do I enter the Sissy Lingerie Competition?

There are a couple of ways

(1)    You dress in your favorite lingerie. Panties, bras, chemise, high heels, nylons – the works, and whatever you chose to wear—take a few snap shots and send them to me in a message either a message on Niteflirt or via my yahoo messanger. Include in the message that it’s for the Sissy Lingerie competition.

(2)    You can call one of the judges, show yourself on cam, and allow us to take a couple of snap shots.

**You do NOT have to show your face in the images, but know that the images may be placed on our blog as we decide the winner of this particular competition.**

Show us what you got! The images will be judged by category – sluttiest, cutest, and sexiest

Who are the Mistress Judges?

Each of us sissy trainers loves to have our sissies competing…not just for the sissy crown but for our adoration as well (What is more pleasing than pleasing your mistress?)

In this round we have 4 judging mistresses–Myself, Mistress Fernanda, Mistress Reaghan and Mistress Olivia. Here are our head shots that link to our blogs, as well as a call button if you want to get to know each of us a bit better.

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Competition starts NOW 

It starts NOW and I will be accepting submissions until midnight eastern, April 30th with the winner announced May 7th.

This is sure to be just the first leg of our summer time sissy competition series, so enter them all because at some point, we will have the overall completion to crown the queen sissy!

So maybe it’s time for you to go out and get some NEW lingerie? Hell what girl (born or sissy-made) doesn’t want new lingerie?

Have fun and good luck!

Sissy Training Phone Sessions with Mistress Lillith
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First Time callers get 3 Free Minutes.