Category Archives: Mistress Lillith

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.

Being a Sissy Housewife

Are you the Sissy Housewife Type?

Sure you can watch your tv shows of the Real Housewives of ‘whatever city’. Gorgeous women, with luxurious lives. You, my sissy, can be a gorgeous sissy but your luxurious life will be much different.

The lifestyle of outtings and parties is for the enjoyment of your Mistress. SHE is the one that regularly attends A-List social gatherings…and you as the sissy…if you are lucky – will get to join her as her servant.

You are the housewife Sissy. Your duty is to serve.

You could see this as a sissy maid type role but I see a sissy made as someone with a uniform and one that would sleep in separate quarters.

The housewife would actually get to sleep in the house and even though there would most certainly be a separate bed situation going on.

Your duties as a housewife are similar to that of a sissy maid. You do the cooking and cleaning, the chores and make sure that your Mistress comes home to a glass of red wine and foot massage, on especially hard days, an already drawn bubble bath.

Your hair must ALWAYS be in tip-top 50’s style shape and you must always be prim and proper. You DON’T look like the maid, but you certainly have the duties of one.

When you’ve done your chores you only hope that the latest soiree so that you can be shown off as a top Sissy Housewife by your mistress.

And yes, just like a housewife is expected to perform certain marital duties – you will have those as well.

Let’s just see how you fair as the housewife first. This is another way that you differ from JUST the sissy maid. A Sissy Housewife has extra privileges that a sissy maid, may never encounter.

If you are a prim and proper Sissy that is devoted to your mistress in a special way, perhaps you would fit the roll of a Sissy Housewife. You are an Owned and Kept Sissy Housewife. Your Mistress doesn’t have to lift a finger when you are around, you are hopelessly devoted to her and you are going to look fabulous while doing it – you don’t get to be an ugly housewife.

Don’t worry dear, if you are new to the housewife sissy duties, Mistress Lillith is here to show you the way.

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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Justen — Sissy and Tranny Fantasies

Affirmations are something that EVERY sissy should do. When I start my 12 step sissy school camp, they ALL start off with affirmations, but each one has a different SET of affirmations tailored to every sissy’s need. I have said this numerous times but I don’t believe in fitting anyone into a box. Perhaps you are a sissy slut that loves the frills and lace, or maybe you are just a man that enjoys wearing women’s panties but don’t refer to yourself as a sissy. While there may be CATEGORIES you fit into, you won’t fit in PERFECTLY because you have your own individual set of needs, wants and desires…THAT is what makes you perfect, not the box.

I have been enjoying the torment that Sissy Justen has been enduring as of late. Here are her latest sissy diary submissions:

7/15 I did my affirmations this morning when I woke up, when I closed my eyes I saw me putting on girlie clothes in front of a mirror. There were a few girls there, and they were helping me. Today I had a salad for lunch which I was good, there wasn’t anything special about it though. Honestly I was thinking if I was cool with people not knowing this side of me, and I found out that I am, the only person I’m cool with sharing this side of me is my partner whoever they may be a mistress or a girlfriend or wife, doesn’t matter who they just need to be able to accept me for me :)!

Mistress Commentary: It is always wonderful to have that person you can truely, honestly connect with. Be it a mistress, friend, or significant other. I also wanted to add, that perhaps this vision of putting on your finest sissy maids uniform or sexy negligee could in fact come true! I could find another sissy training mistress to watch you, perhaps for your graduation? 

7/16 Today I did my affirmations while my eyes were closed I saw myself as a maid servicing woman and trannies which turned me on a little ;).

I edge after that and didn’t cum. When I finished I took my shower and today I felt like I smelt really good. I went to school then went to a friend’s house and listened to her as she talked about her boyfriend and how he was coming back this week. I don’t like her boyfriend he is a dick but she likes him so I just listen. When I got back I was in the basement with my family watching a t.v. Show and I saw this woman, she looked so hot I wish I looked like her and had a girlfriend, mistress or whoever like her she was amazing :0.

Mistress Commentary: Ahhh A bit of a Tranny Fantasy Huh? We will be having some fun with this one. Nothing more exciting than being able to be with an Exotic woman. A girl with…Something EXTRA. 😉

7/17 today when I got up I saw that my parents were not home so I gathered a pair of panties a garter belt and stockings and went to the bath room. I shaved my legs half way before I took a shower. I hate shaving I am always worried I’m going to cut myself :(. After the shower I put on my panties and other stuff and walked into my room and started doing my homework. After a couple hours my parents came home and I put on some pants over my girl clothing. They left so I took off my pants then I did my sissy affirmations and saw myself as a sissy school girl with long black hair the outfit I saw myself wearing was hot!! I went downstairs after my affirmations and watched a little t.v, after that went up stairs and read a book. Today was a good day, kinda boring but I needed to stay home.

Mistress Commentary: Shaving is a hassle for boys and girls. Mistresses and Sissies. I am somewhat of a masochistic myself and LOVE getting them wax. One day I will go and get the laser hair removal on my legs but we’ll see. As far as nicking yourself…It will happen. It seems to happen LESS with me when I shave using hair conditioner or lotion and then right after putting baby oil on my legs. (there is a nice little sissy shaving tip for you all to enjoy)

7/18 this morning I took a nice long bath, it felt so good. I had my laptop in and had the mp3 for the affirmations and listened to it a couple times. I really enjoy listening to it.

While I listened I saw myself sucking a girls cock while other girls watched, I was wearing nothing but a bra and panties.

It made me get horny so I edged after the bath. After I edged I did a little yoga in my panties the put on pants and helped my parents move furniture so my mom can paint. I went out after and saw skyfall which was boring. I went home and them played a couple video games with my friend and talked to my other friend who went to basic training. Then I went to bed… I have school tomorrow 🙁 I wish I had it off!!

Mistress Commentary: To bad you cant compare notes…His Basic Training to your Sissy Training I bet they can be equally intense physically and mentally. 😉

That was the weekend of Justen and Next week I’ll post her next sissy diary submissions. She seems to be enjoying the training and slowly but surely seeping into this new lifestyle and way of life.

There still is the issue of NAMING my sissy~ I think we have narrowed it down, and the naming ceremony will commence very soon! 🙂

Justen — Sexual Frustration is Rising

Here are more of Justen’s Thoughts as he continues his 12 week sissy training process. How do you think he is faring? Feel free to comment below with suggestions, comments and/or questions:

7/13 Today I didn’t have to go to any classes so I stayed home for awhile and took a long bath.i love taking baths the heat feels so good, I love closing my eyes. After I did the affirmations I closed my eyes and saw myself next to a blonde girl we were cuddled in the bed both wearing corsets and stockings she had her arms wrapped around me. When I got out of the bath I put on some pink panties with hearts and walked around since I was home alone.

I felt pretty horny so I tried orgasm edging…then got worried that I was going to cum so I stopped.

I left the house wearing the panties and did a couple things, and went to my school. When I got back home I said hi to my parents and went to my room and did a little homework and then edged again. I feel so horny all the time! It sucks 🙁 I want some release please, pretty please!?

7/14 OMG  today felt so good outside!! Today I went to school and sat through my boring classes :(.

When I got home I did my affirmations, while my eyes were closed I saw myself wearing guy clothes but under it I had on panties, a garter belt and stockings.

I was walking arm and arm with a girl. I had a butt plug in my butt, and the girl knew that I had the plug in. when she knew that there wasn’t anyone was looking would rub against my but reminding me that it was there. I think the easiest habit or thing I can do is take a shower using feminine soaps and stuff since I take a shower every day, and now I’m using feminine soaps. I also tried doing some yoga again :)… But I’m not flexible yet so it’s all really hard to do :(.

I haven’t came yet, this whole edging is hard by the way.

I am really looking forward with the buying girls stuff, I don’t know what items I should buy which is what I need help doing or like a list of stuff I need.

Justen- Forming Ritualistic Female Habits

My Sissy Justen is in his 2nd almost 3rd week of Mistress Lillith’s 12 step sissy training program. He seems to be progressing along nicely.

During his first week, he had affirmations to repeat daily. Words are very powerful and the more he recites his personal affirmations, the more he believes them and gets into that sissy subspace of a mind.

This week he is prepping the feminized body in a few different fashions as well as setting up some ritualized feminine routine.

As girls we do have daily routines that we do to keep our selves chic, sleek, and sexy.

Part of his requirement is to write regularly in a diary and have it submitted here for all to read, and so HE can keep track of his progress.

Here is one of his submissions:

Justen Said—“Today I took a bath using the feminine soap I bought and at the end I said my affirmations. Since my body was loose because of the bath I tried to do a little yoga, which I find hard because I have no flexibility at all! When I finished I laid and calmly slept. After that I talked to my Mistress which I enjoy, she is the only person I can talk this stuff to. I asked her to if she can give me a name and she said to give her time. Then I told her about myself so she can have an easier time with my name.”

Naming my sissy isn’t something I take lightly. This training is an intense 12 week course that is designed to get you on a long term path to feminization and sissfication. I am working on a name for naming Justen and it will be a ceremonious day when his new hame is revealed and HE becomes a SHE.