The curse of enjoying chastity as a sissy

I feel like I hear stories about people wearing chastity and being extremely productive and being able to focus on personal growth much more.

My issue with this is that I am not one of those people. I’m on one week within my inverted chastity cage and my mind is racing.

My thoughts and actions in just the past 24 hours:

- “ewww why do I still have body hair,” the I proceed to exfoliate my skin then shave my body from head to toe.

-my legs look nice but all of my clothes are way too scratchy for freshly shaven legs. I then proceed to get in my car and drive to target to pick up some tights and stocking. ( I already own way more skirts than I’d please to admit).

- hey I should really do some work…. No I’d rather just listen to sissy hypno audio files while I look at cute clothes I want to buy.

- hey I should put some make up on, nothing too stand out and noticeable because I don’t want to attract the wrong attention…well ….a little attention actually sounds kinda fun. Maybe just some mascara, a bit of lip stain, lip plumping serum, just a little highlighter and blush, and a tiny bit of pink shimmer eye shadow. You know just the standard amount for any secret sissy who define you doesn’t want a girl to come up to him and compliment his make up.

I don’t think I’ll ever be the type to get work done in chastity. But I know one thing though I am a smooth hyper femme sissy who is growing closer and closer to the day when I say fuck it and just jump down the sissy rabbit hole with no regards for ever coming back out.

reddit.com
u/Early-Brief2815 — 9 hours ago

I might have fallen a little too hard down the sissy rabbit hole

Now on day 4 of chastity, also on day four of vigorously bouncing on my 9 inch dildo and when the inevitable happened and I sissygasm all over the floor. My first instinct wasn’t okay well I guess the session is over time to clean up. Instead I said out loud “sorry for cumming without permission I’ll clean it up daddy” then without skipping a beat I lowered my head to the floor and proceeded to lick it up while repeating “I’ll be a good girl for daddy”.

Yeah I definitely think my life would be a hell of a lot different if I was introduced to chastity earlier on in my sissy journey.

reddit.com
u/Early-Brief2815 — 6 days ago

The sissy dilemma

So low and behold I was able to get myself out of the cage I had thought I was stuck in. But now I have a dilemma.

I desperately want to edge myself to sissy hypno video and cum on my face and in my mouth but I also love this steady flow of desperation and sissy cocksucker energy that is pulsating inside of me and driving me to follow through with my sissification.

I think I know what I have to do. As amazing as it would be to taste a load of cum. I need to focus on the end game and it’s going to be so hot when in 3 months when I allow myself to have a sissygasm.

Although after reading a previous post I wonder how desperate and cock crazed I’ll be if at the end of the 3 months no cumming challenge if I allow myself to sissygasm but then decide right at the last moment to ruin the orgasm so I get no pleasure out of it. Maybe I’ll record a video of it.

reddit.com
u/Early-Brief2815 — 7 days ago

Play stupid games win stupid prizes

Today I learned an incredibly easy and painfully avoidable lesson. So to provide a tiny bit of context is needed.

I am chastity lover, I self cage and I hold the key and I generally enjoy seeing how long I can push my body and mind down the sissy rabbit hole while continuously locking up my bits in the smallest and most compact clitty cages I can find.

So what leads me here today, I only have one flat cage but I lost the key to it. Also I might add that the lock and key are like every other cage I have but it turns the opposite way. Now, today I was feeling like I desperately wanted to feel the sensation of a flat cage and I didn’t want to buy a new key or flat cage so I compared the base ring size to another cage I own and tried putting it together but the peg holes were a bit too big and deep. Now most sissies would call it quits there but not me. I took out the electric nail filer and shaved away at the peg holes and lock to make it sync up perfectly.

Now here’s the situation, I believed it was perfect because when I tested it not on my body I was able to push it in with a bit of force and pull it out with a small amount of force as well. I was straining to get it in or off but it was just a little nudge that was needed due to it being a different piece.

Well I didn’t account for the pressure of my clitty pushing against the flat cage and Well I put the cage on and when I went to take it off because I wanted to put my harness on the key broke up in the lock in the locked position.

Hahaha the funny thing is that it fits really nicely and part of me just wants to say fuck it and treat it as a practice round for the start of my eight month journey as I attempt to complete Sissification September, Locktober, No Nut November, Denial December, Jeweled Jail January, Feminization February, Masculinity Melting March, and ending it with Abstinence April.

reddit.com
u/Early-Brief2815 — 8 days ago
▲ 9 r/SchoolOfFeminization+2 crossposts

CALLING ALL SISSIES!!! Question time. How many sissies rew up around religion, and would you say that it affected your feminine identity and how you express your sissy side?

if you dont mind can you take the quiz in the hyperlink? ill post the results once i get a good sample size but im actually so curious how many sissies were raised reigious and how many of us still suffer from it.

https://form.typeform.com/to/yFkdRe00

reddit.com
u/Early-Brief2815 — 8 days ago

Questions for sissies with ADHD

I’m not sure if this is just a me thing but does anyone else feel like when they take their adhd medication that it makes them either horny or at least amplify their sissy energy?

I take vyvanse and every time I take my vyvanse lay at night thinking “oh I’m going to get so much done tonight”, when in contrast what really ends up happening is that I either fall down a sissy hypnosis rabbit hole where my night either falls into one of two categories.

Scenario # 1 : I spend the night feminizing myself like I was reading a step by step tutorial from shaving, to painting my nails, to doing my make up and then try on all of my clothes and have a mini photo shoot.

Scenario #2 : I watch hours upon hours of sissy content from literotica, to sissy web novels, to watching sissy hypnosis all while riding my dildos like a sissy chasing the infamous sissygasm.

I don’t regret being a sissy and I’m not ashamed of it but sometimes id truly like to just get work done with out being horny.

I guess the question was do other sissies struggle with staying focused and what do you do no that helps?

Side note: Also I think that my chastity cage doesn’t really help me stay focus like I’ve read. If anything it makes me less focused. Any tips would be much appreciated?

reddit.com
u/Early-Brief2815 — 9 days ago