Tag Archives: sissy school

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.

Diary Entry: Sissy Waxing Part 1

I believe in Feminine Rituals. I am female, and I do engage in said feminine rituals on a regular basis. I believe that sissies must learn these rituals and complety them daily in order to live their sissy lives. How can you call yourself a sissy if you DON’T engage in these rituals?


 

Mistress Lillith’s rituals assignment is due in 1 week and I needed to get started early.

I searched through a few local salons–one that was super pink and girly and another that was more gender neutral–and settled on the gender neutral one. I called to book an appointment.

“Hi, I’d like to come in and have my legs and maybe areolas waxed.”

“We can do that. Are you looking for a brazilian? We can’t do brazilians for men, is that okay?” the receptionist asked. “That’s okay, I just need my full legs waxed.” “Okay, let me check with the beautician to see if she can fit you in today. Hold on.” “Okay, are you able to come in this afternoon?” “Yes, thank you.” And I booked the appointment. But…

2 hours later I received a call from the salon… “Hi Robert, I’m sorry, I’m new at this salon and I’m afraid the beautician isn’t comfortable waxing the entire leg. We do have another staff member that will wax your full leg but we would need to wait until tomorrow.” šŸ™

… And the appointment fell through.

Needing a backup I called the super pink and girly and intimidating (but highest rated Yelp) salon in the area and booked an appointment. Everything was set.

Immediately after booking I received a call from the first salon’s manager. “Hi Robert, I’m sorry for the mix-up. We can get your full leg waxed today at a discount if you’d still like to come in.” Lol.

I think I might have inadvertently caused quite a stir.

This part of the story almost got deleted from the diary but made it in because–without passing judgement–I think the reaction caused by crossing gender boundaries is interesting.

The super pink and girly salon turned out to be super pink and girly. The entire area oozed femininity. Next door was a bridal shop. I entered the salon and approached the receptionist. There were a few women sitting in the fluffy pink and light green chairs and couches, staring at their glowing rectangles.

I was handed a new client form to fill out and given a bright pink glitter pen.

I was in foreign territory.

After finishing the form I handed it to the lady who would do my waxing: a young, cute bouncy, bubbly girl, who obviously cared about her makeup. Her dark green eye shadow extended out far from her eyes and then cut off sharpy at a 45 degree angle. Glitter shined from parts of her face. Her hair wasĀ HOT PINKĀ and was pulled tight into a scrunchy that sat at the crown of her head, from there her hair flowed outward above her head like the stem above a carrot. This was Jessica.Ā I was deep in foreign terriotry.

“Follow me,” she said. And we proceeded through the facility into the waxing room. “Take your clothes off. Leave your boxers or underwear or whatever you got on down there on. Lay down on this bench with your head on this end and I’ll be back in a few minutes.” I did as I was told. She entered after a few minutes and I meekly asked for a vanity towel and was obliged.

Something hot was being spread on my leg. “So why do you want to get your legs waxed?” the pink haired girl asked. Hmmm… How to answer this? … … My Mistress is feminizing me?

Probably not a great answer. I began to sputter something about my hair and being unsatisfied with it and suddenly in the middle of my sentence my lungs gasped for air and my speech was cut short as sharp pain shot up through me like a lightning bolt. “uuuuuuggghhh…” I ended my answer prematurely.” Jessica giggled.

HO-LLE SMOKES. Waxing hurts. A. LOT.

I had read reviews about it being bad but I was genuinely surprised how much it hurt. Jessica and I made chit-chat the entire time. She was young, not married, into music, gave me tips on skin care and exfoliation, had 3 male clients and blah blah blah. I was constantly having my speech cut short by sharp pains as hair was ripped out my skin.

My nerves were on fire. “Maybe I can’t handle BDSM pain,” the thought occurred to me.

It was hard to stay focused on what was happening and not daydream about why I was here getting waxed. Fortunately I managed to stay soft and OH MY GOSH am I thankful for that. Finally after two hours it was over.

As I was paying the receptionist and getting ready to leave Jessica came to the front desk and reminded me: “Don’t shave it when it starts to grow back. Let it grow for 4 to 6 weeks and then come back and see us. It won’t hurt as bad next time. Use an exfoliater tomorrow and moisturize afterward.” For the first time since arriving I looked her in the eye and thanked her. Something curious happened next.

Jessica turned bright red as she smiled, looked at the ground suddenly, mumbled a thank you, and then hurried out of the room.

Jessica blushed hard! I wonder… (to be continued)


This part of the training always cracks me up. Obviously I don’t expect ALL of my sissy trainees to get waxed, there are work around and other rituals. But the ones that DO go out and get a wax, are always in for quite a sissy adventure.

 

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.Ā 

Diary Entry: Getting Trained as a Sissy

*This entry is from one of my newest Sissy Camp Trainees*Ā 

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 šŸ˜‰ 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 serveĀ Mistress Lillith? Money is the best way. It allows me to pay to have her lawn mowed, or have her house cleaned, or whatever elseĀ *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.