Tag Archives: sissy training

Diary Entry: Real Changes and a Sissy-gasm

There are real changes happening.

I noticed them Sunday night as I put my 5″ stilleto high heels on. I thought I would manage okay in high heels, but I couldn’t really walk, and I couldn’t control myself sexually either. That last one bears repeating.

I couldn’t control myself sexually in high heels.

Mistress Lillith had me purchase a chastity device and had been making references to sexual frustration and compliance in some of her messages, which sounds both fun and a little scary.

Prior to Sunday, I had been chaste since last Thursday. I had a pink ribbon tied around my clit.

It’s constant rubbing causing very mild irriation. I was wearing panties occasionally, and I dutifully listened to my mantras prior to bed–playing them on repeat with Mistress Lillith’s subspace hypno goodie as I fell asleep.

Sunday I had some alone time for the first time since … Thursday.

My shoes and cut-offs arrived on Saturday.

I put on the cut-offs with my tank top and thong underwear. WTH, size 31 is never tooooo big for me. I didn’t realize they would stretch so much. Okay that was a little disappointing.

How about the shoes?

Oh my gosh, perfect fit. The strap tied around my ankle, locking them in place. (The strap was surprisingly hard to lock and unlock!) I tried standing: my butt and chest instantly pushed out in opposite directions. Whoa, weird… and interesting. I took a few wobbly steps and realized I didn’t know how to walk in 5″ heels. “I’d better sit back down,” I thought.

Mistress Lillith’s twitter feed had showed some unusual NF activity for her on a Sunday, especially a holiday weekend. I thought there might be a chance of contacting her. I even tried reaching out to her on Skype, which I’ve never used before. No luck.

I purchased a tease and denial dice game video instead.

Stroking. Slow and fast. Alternating styles. It was clear there wouldn’t be a chance to orgasm at the end fo this video. On the last 5 of the dice rolls Mistress Lillith had me edge the number of times as on the die.

Pausing the video… stroking… staring at my shoes. Edge… Breathing… Again… Fuck, my shoes. A tiny pink ribbon bow sticking out from cut offs that were now riding up my ass. Edge. Again.

I was pulsating and twitching. An extra five dice rolls were granted, more stroking but ultimately denial. Staring at my shoes as I stroked… Oh no, I’m cumming. I tried to stand and to make it to the bathroom, but I COULD NOT WALK. ERUPTION. I collapsed in my chair. I completely lost control. Lost control of myself, of my feelings, of my arousal. I hardly recognized the view of my legs… a pink ribbon… a sticky mess… my shoes.

I completely lost control. Wow that was an intense orgasm. Shades of my teenage self. There are real changes happening to me sexually.

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.” 🙁

… 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 was HOT PINK 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. 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. 

Diary Entry: Getting Trained as a Sissy

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

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 😉 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 serve Mistress Lillith? Money is the best way. It allows me to pay to have her lawn mowed, or have her house cleaned, or whatever else *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.

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.

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.

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.