r/SissygasmSchool

I want to play with my cum more but I am almost scared and grossed out by it once I actually come. Does anyone have any tips or ideas to start to incorporate it more, eventually I would like to eat it and even give myself facials.

Hello, my leaking little sissy hopeful. If these words are making your heart race and your clitty twitch, you’re already halfway mine. I’m Mistress Olivia, and I specialize in long distance, fully online femdom training. I don’t meet subs in person I break them and rebuild them from afar through messages, voice notes, video calls, photos, and videos. You stay in your own space, safe yet completely exposed to my control. I instruct every detail of your transformation while remaining a powerful, teasing presence on your screen.

Your obedience is captured in proof pics and videos you send me. Your pleasure and denial are dictated by my commands. Ready to begin your descent?

Step One: The Click of Chastity... Remote Denial & Daily Proof

Your training starts with a simple order sent straight to your phone: buy a cage and lock yourself for me. The moment that click echoes, your old life ends. I control the key metaphorically and you’ll send daily proof photos and short videos showing your locked clitty, swollen balls, and desperate expression.

I’ll tease you mercilessly across time zones. Voice notes describing how wet I get thinking about your frustration. Pictures of my legs, my curves, my strap-on, all designed to make you throb helplessly in your cage. “No touching, pet. Leak for me instead.” Weeks of denial will follow, with extensions as punishment and brief teases as rewards all managed remotely through our chats.

The ache becomes your constant companion, rewiring you until you crave my next instruction more than release.

Step Two: Shopping Assignments....Solo Sissy Humiliation on My Command

Since I’m not there in person, I make your public tasks even more thrilling through detailed remote instructions. I’ll text you exactly what to buy and how to behave.....“Go to the lingerie section. Pick out the sluttiest sheer panties that will barely hide your cage. Choose thigh high stockings that make your legs look fuckable. Find a short skirt and a tight crop top. Try them on in the fitting room and send me mirror pics with your cage visible.”

You’ll shop alone, pulse racing, wondering if anyone notices your secret. Send me timestamped proof from the store evidence of your obedience. Back home you’ll do a full private fashion show for mel. I’ll watch live or review the recording, critiquing how each piece hugs your body, how the panties frame your locked clitty, and exactly how I want you posing and twirling.

Every outfit is chosen and approved by me. You’ll wear my selections during future tasks, feeling owned even when you’re miles away.

Step Three: Forced Cock Sucking Practice.... Filmed for My Pleasure

I’ll assign realistic dildos with a strict size progression. You’ll set them up in your room and practice exactly as I instruct on camera for me.

“Start by kissing the head...Use lots of tongue. Now take it deeper… I want to hear you gag.” You’ll record full training sessions drooling, choking, eyes watering, practicing the perfect rhythm and depth. Send the videos to me for review and feedback. I’ll message back commands like “Slower on the way down next time. Make it sloppy that’s what good sissies do.”

Over time, these solo sessions turn you into a skilled cocksucker, all while I watch your progress from afar and tease you about how you’ll eventually crave the real thing under my remote guidance.

Step Four: Pussy Stretching & Sissygasm Training ....Guided from Afar

Your boy pussy training is fully remote and intensely intimate. I’ll create a custom plug and dildo schedule. You’ll insert the toys as ordered, wearing smaller plugs for hours during your day while sending proof pics.

During scheduled video calls, I’ll direct your stretching sessions in real time: “Ride it slower… angle it upward… tell me how full you feel for Mistress.” You’ll bounce on larger toys, locked clitty leaking, while I coach you toward the ultimate goal hands free sissygasms.

I’ll teach you exactly how to massage your prostate, the perfect rhythm, and the mindset shift needed to cum like a proper sissy: shaking, whimpering orgasms with nothing spurting from your cage. Many of my online subslearn to have multiple sissygasms in one session, left ruined and addicted on their bedroom floor while I praise or tease them.

Your Complete Online Sissy Journey

This is an ongoing, deeply personal online submission. Daily check ins. Constant teasing across chat. Custom tasks that push your limits from the comfort of your home. I control your chastity, your wardrobe, your training, your orgasms or lack of them, and your gradual ffeminization.

You’ll send proof of every assignment. You’ll edge on command. You’ll learn to beg prettily through text and voice messages. The distance only makes the power exchange hotter you’re alone with my voice in your head and my instructions ruling your body.

Ready for One-to-One Online Submission?

If your locked or soon to be locked clitty is dripping right now, if your hole twitches at the idea of me controlling you from afar, and if you’re aching to prove your devotion… apply.

I offer exclusive one-to-one online femdom training. This intimate long distance dynamic includes...

Personalized chastity programs and denial games

Detailed shopping missions with proof requirements

Daily tasks and accountability check ins.

Constant teasing voice notes and messages

Full wardrobe control and feminization guidance

Progress tracking as I mold you into my perfect remote sissy

Serious applicants only. Message me with

Your current experience leve beginner is welcome

How long you’ve fantasized about online sissy submission

A clear photo of you locked in chastity or holding the cage you’ll wear for me.

Why you want to surrender to my remote control.

Don’t delay. I expect eager, obedient sissies who follow instructions perfectly.

Lock up if you haven’t already. Re read this while slowly edging that denied clitty. Feel how badly you need my online dominance. Then send your application like the desperate, dripping sissy you’re becoming.

Your transformation is just a message away 🖤

Kisses

Mistress Olivia 💋

Hello fellow girls,

So I recently discovered something new and strange. It happened yesterday when I was enjoying myself and was fucking my cute little bussy.

I’m establishing a new routine which seems really nice and puts me into a girly mindset 🥰 to achieve my ultimate goal of having my very first sissygasm.

Cleaning —> panties —> startup phase (hypnosis and porn)—> buildup phase —> pounding phase

So for the last 8 days I did this routine and never cheated by touching my clitty. The last few days I always got tiered but got really close.

Yesterday it was really warm and I drank a little more which filled up my bladder a more quickly than usual. I just didn’t think about it much and started my routine.

Once I reached the pounding phase I needed to pee but didn’t want to stop cause I really was in the mood. And then it happened…. I enjoyed it more and more and a feeling was building up more which I really enjoyed. I had my eyes closed cause I was enjoying the moment so much and zoomed out a bit. I always start to roll back my eyes. Until I realised I started to cum or pee I don’t know it was but it was clear and it was such a good feeling and I could control it. I made such a big mess and got embarrassed cause I never had this. On the other side it felt so fucking good.

I stopped after I realised I made a really big mess but I want to repeat it again? No PNC

Was this my very first sissygasm? Have you ever had something similar?

Thanks in advance :)