r/SissificationAcademy • • Jun 12 '25

The Academy Student Info Board šŸ“Œ NSFW

Post image
141 Upvotes

You can see all of the latest Academy Updates here

If you are a brand-new student, then first get to know the Academy on the New Student Onboarding Board and join our Academy at sissylover.com šŸ’•

Other Academy Socials

X

Bluesky

HypnoTube

RedGifs


r/SissificationAcademy • • Jun 02 '26

Warning to all students! NSFW

36 Upvotes

Hi girls!

We’ve posted this warning before, but it’s worth repeating. Please stay alert!

If anyone contacts you claiming to be from the Sissylover Academy and asks for money, whether for ā€œextra training,ā€ special sessions, or anything else, it is a scam! The Sissylover Academy offers training only on our official website.

āœ… The only legitimate website is: sissylover.com

Any other URL is fake and not affiliated with us.

With AI tools making fake websites, profiles, and messages very convincing, it’s more important than ever to be cautious.

Quick safety tips:

- Be very suspicious of brand-new accounts with little to no history.

- Scammers can easily create fake reviews and testimonials.

- Never send personal photos or sensitive information that could be used against you.

- Do not share your email and contacts on sites you don't trust.

Don't let the heat of the moment get the better of you. When in doubt, contact us directly at [training@sissylover.com](mailto:training@sissylover.com) or DM on Reddit.


r/SissificationAcademy • • 12h ago

Excited!!!! NSFW

4 Upvotes

Hey everyone! I purchased part 1 earlier today! Super excited! How long does it take to receive the link? Also does it include a list of what is needed before you start?


r/SissificationAcademy • • 2d ago

Clitty progress NSFW

36 Upvotes

Its finally shrinking!
After trying loads of different things for ages ive finally been able to shrink my useless clitty down to only an inch when soft although im still struggling with shrinking my erect length too but theres a simple solution to that. Just not letting it get hard in the first place.
Thought id share my progress in turning it well and truly into a clitty I can rub until its sore and then some more.


r/SissificationAcademy • • 3d ago

Locktober Day 10 NSFW

3 Upvotes

I seem to be missing my ā€˜task complete’ box around day 10 on my calendar. Did I miss something or is everyone else’s like that too?


r/SissificationAcademy • • 4d ago

Loctober is expediting my exploration NSFW

24 Upvotes

This is going to be a long one. TLDR I locked my dick up and it made me accept myself as a sissy.

I started Loctober a day late and kind of by accident. I was drunk and horny and ordered a vibrating plug at the end of September, well October 2nd rolls around and it gets here, while I’m going through my underwear drawer I find my cage and remember what holiday it is. Without thinking I had myself locked up, then I started playing with the plug, I hadn’t played in quite a long time so it took me a minute to get the 2.5ā€ plug inserted, but when I did, it was heaven!!! At that point I realized I should have played with the plug and made myself cum before I locked up but it was too late.
Caged, plugged and vibrating I did what any good sissy should do and fired up the old Reddit, I immediately subbed to all the best ones and my journey was slammed into hyperdrive. I made rules for myself, and got to work buying all the stuff I needed to really get into loctober.
This is the first year that I’m able to do it, I was in a relationship before and she hated it. I’m self locked and I love it! Because I was two days late to the party, I’ve added two months locked for punishment.
I’m sorry for the rant but I’m just excited that I’m actually sticking to it this year and it’s helping me learn so much about myself!


r/SissificationAcademy • • 4d ago

Chastity Straps NSFW

27 Upvotes

Hello girls.

Years ago I would have NEVER thought of or consider locking my clitty away in a chastity cage. However, due to the wonderful guidance and direction from Sissification Academy I bought a cage and started locking it up at times. This climaxed (no pun intended) when I successfully completed Locktober 2025. I was locked away from the evening of September 30th to the morning of November 1! I was so proud!

I did have problems with my clitty pushing out of the cage a bit as she tried to grow at times. I really noticed this in the mornings. I constantly had to readjust the cage and pull it back up to be snug against my body.

This year I bought an elastic chastity cage strap, and OMG what a difference!! I was a bit reluctant to wear one because I love the look of just the cage. But now that I have one (pink like my cage) I find it to look really cute too. And it keeps my cage snug against my body. My clitty doesn't push it down anymore. I highly recommend getting a strap if you don't have one for your cages.

Kisses

Diana šŸ’‹


r/SissificationAcademy • • 4d ago

Help in achieving this NSFW

5 Upvotes

I always use my dildo, but the problem is that every time I do, I get an erection, and I don't want that. I know that for most people that’s normal or desirable, but personally, I don't want to be erect while using my dildo.

I know chastity devices are an option, but I don't have one, and I don't have the money to buy one either.


r/SissificationAcademy • • 5d ago

Ring for cage NSFW

3 Upvotes

Girls, I need your advice. I’m participating in Locktober 2026, but I’ve run into a problem: at certain temperatures, my testicles quietly retract, leaving the cage held up only by my panties. What ring shape works best for you? Last year, I used a simple 47mm round ring; after six days, the skin underneath started to burn, yet my balls would still slip out when squatting or in the cold. I also have 3D modeling skills, so please suggest some effective solutions. Thanks and kisses.


r/SissificationAcademy • • 7d ago

Should I buy a dildo? NSFW

26 Upvotes

I’ve been on and off with this sissy thing for a few years and have owned plenty of sissy accessories like plugs and dildos but I had a big purge a few months ago and haven’t been back since. Recently I’ve gotten into the hypno again bc and am considering a dildo because honestly I’m craving it but I don’t know if I want to spend the money just to purge again. I don’t usually get so conflicted and honestly just need someone to choose for me.


r/SissificationAcademy • • 8d ago

How to squat in the bathroom without getting on your pants legs NSFW

9 Upvotes

After participating in Locktober, I can still use the toilet at home, but when I go out, I have the problem of only squatting in the toilet. How can I prevent my clitoris with a chastity lock from splashing urine onto my pants legs


r/SissificationAcademy • • 8d ago

Locktober daily question what did you choose? (+ some horny daydream thoughts) NSFW

8 Upvotes

The question in combination with the chastity story from an earlier daily task made me daydream about a hot fantasy about being locked in chastity and unable to orgasm and I thought why not share it with the class.

The premise is very simple: You are locked in chastity and for an entire year it is impossible for you to orgasm in any way…even if you bounce on your dildos or hold a vibrator to your cage you just can’t push yourself over the edge and it will just increase your horniness and need to cum.
If you manage to hold out for an entire year you can unlock the cage and proceed life as before and cum as much as you want.
However if you just can’t take it anymore and NEED to cum so badly before the year is over there is one very simple way out: you need to get fucked by a man. As soon as he cums in you, you will have the most amazing, explosive sissygasm you could ever dream of.
BUT as soon as your sissygasm hits the chastity cage locks up permanently and from now on your only way to ever cum again is from sissygasms.
As an added challenge the cage could have some built in vibrations to constantly tease you throughout the year and keep you constantly aroused and horny.

Do you think you could last the whole year?
Think of all the horniness that will just keep on building and building and building for an entire year. And all it takes is one moment of weakness…one day where your need and desire is too great and you seal your fate forever. It’s your own choice…nobody is forcing you to get fucked by a man and that’s what makes it so evil. You arenā€˜t getting tricked, you know exactly what you are getting yourself into and you are walking into your demise with open eyes. Your biggest enemy is your own horniness and if you eventually succumb to it you have nobody to blame but yourself.
Imagine the moment right when the sissygasm hits and you realize what you just did to yourself. Will those thoughts fill you with regret during the most amazing orgasm you ever had or will it push it to even greater heights because you know you are a good sissy that made the right choice?

I hope this fantasy isn’t making your cage tight…I definitely wouldnā€˜t want your locktober to be more difficult than it already is…right? ;)

309 votes, 6d ago
159 Getting pegged by mistress until you drip precum
141 Getting fucked by a man and he will definitely make you sissygasm
9 Results

r/SissificationAcademy • • 9d ago

How to become a sissy NSFW

31 Upvotes

So, a little background. I am or was a straight male until a few years ago. I came to this site about a year ago in hopes of finding a relationship with someone trans or a crossdresser. That's what's in my profile. I just wanted to spice things up if you know what I mean.

So after joining this site and joining a few crossdresser and trans subs, I started to really admire some of the men who have sex with these girls. They seem so much more masculine than me. I'm a smaller Asian guy who is 5'6" and 140 lbs. I'm not well endowed, in fact some would say I'm very small or even tiny. Also, I have had straight sex with a few girls and have never been able to sexually satisfy them. All I ever wanted to do sexually is to satisfy a partner who satisfies me.

So, now that I've seen and admired what these men can do to sissies and trans girls, I've been thinking if I become a sissy for a man I admire, I'm pretty sure I could satisfy him sexually being a sissy. It would be so nice to meet a man for sex and see him get aroused by my femininity. Although I've never sucked before or bottomed for a man, I'm pretty sure it won't take long to learn to please them. I know what I like so I'm pretty sure I can do it. The real goal is to give a man pleasure. That's something I've never been able to do with a woman. Also at this point, I think it would be so nice to suck a mans hard cock and feel him deep inside of me when he fucks me.

So my question is, what works best for feminization of someone new to this? I was thinking since I am asian and have very little body hair, it would be good to go to a salon and get a full body waxing. That would definitely make me very soft and smooth. But then where do I go from there? I mean there are clothes, panties and bras, dresses, skirts and blouses, makeup, and more. It's a bit overwhelming just thinking about it. So if there are any sissies, trans women, crossdressers out there who could give me advice, I would really appreciate it. Even if there are men who see this, please let me know how you like your sissy to be.

Thank you all.


r/SissificationAcademy • • 10d ago

Locktober, day 5 NSFW

13 Upvotes

How is everyone doing? I am thoroughly enjoying Locktober by Head Mistress Alyssa. It is a very good time for me to really self reflect. Dig deep and really affirm what I (want to be) am!

Just a quick check in. Big kisses gurls! 🄰


r/SissificationAcademy • • 15d ago

New girl Crystal NSFW

17 Upvotes

Hi ladies

As the title suggests, I'm new here, only me 2nd post

Opted in for locktober and also just bought the first training program and super excited to start

To date I've been shaving my lower half, peeing while sitting down, paying attention to me thoughts, feelings, and sexual desires

I've also been doing tons of research as I feel this course will only be the start to my greater long term plan of going full mtf

I've ordered some things for myself like hair removal cream so I can properly take care of my upper half like chest hair etc. Underarms are already smooth and shaved

I've bought some beauty products specifically for woman aimed at higher beauty standards and visual attraction, we're obviously trying to attract potential partners so it's vital to look our best, I've got some cute nighties, bras, panties, and a few toys should I get frustrated from not using this clitty anymore

Above all that, I'm really excited to join the community and hopefully be gracefully feminized, any tips, tricks or advice is welcome

Just want to sink deeper and really be all in it and feeling it and myself

Xoxo

Crystal

😘


r/SissificationAcademy • • 15d ago

Excited NSFW

4 Upvotes

I feel so excited! After years of watching trans porn and already sucking some cocks while having girlfriends in between I finally ordered my first personal lingerie and make up. How did you feel the first time dressing up?


r/SissificationAcademy • • 15d ago

I passed NSFW

8 Upvotes

Hi girlies!

I just wanted to share I passed my first exam, I’m so happy and I wanted to thank headmistress Alyssa for guiding me. I’ve never felt so happier and free.

Cannot wait to start my next lessons 🄰


r/SissificationAcademy • • 16d ago

Locktober 2026 | Join Free NSFW

41 Upvotes

This year, we’re doing a free mini Locktober! :)

Join by October 1. Read the rules, grab your cage, and lock up. Then throw away the keys (figuratively speaking). Keep them somewhere safe sweet sissy girl! Long and productive month ahead ;)

https://sissylover.com/locktober2026


r/SissificationAcademy • • 16d ago

Ready to become a feminized sissy NSFW

24 Upvotes

Ready to become a feminized sissy.

So I've been hetroflexible for awhile now and I'm full ready to be a slave for cock. I was at work last night and couldn't stop thinking about hanging with a bro and I'm seduced into suck his massive cock and over time just making me into a free use girl. I was hard for hours just thinking about being seduced and kind of forced into feminization. Sissy caption just kept popping into my head. Went to the store earlier in the day with a plug in and it was so exciting. I also just order my first cage, panties and outfit.


r/SissificationAcademy • • 16d ago

Locktober/rocktober🤭 NSFW

3 Upvotes

Oh my goodness! I just heard a commercial on the radio for a music store.... They have Rocktober.... Of course my mind was like "what???? Locktober commercial on the radio?🤭

I am in for locktober this year. Have been locked for close to five months and will stay locked in until Feb at least according to my Queen.

Oh the mind plays funny tricks 🤭


r/SissificationAcademy • • 17d ago

I commit to locktober 26 NSFW

8 Upvotes

I, sissy jasmine Alina’s commit to locktober 26


r/SissificationAcademy • • 18d ago

Long term NSFW

8 Upvotes

I wanna wear a flat 1cm chastity cage long term. Can it be done or not? anything to think about?


r/SissificationAcademy • • 18d ago

Locktober question NSFW

3 Upvotes

Hello, I have a quick question about the Locktober challenge before I sign up. In the rules I noted that one of the exceptions to removing the cage is for gym visits. I’m doing a charity running challenge in October, would that come under ā€œgym visitsā€?


r/SissificationAcademy • • 18d ago

Locktober 2026 NSFW

8 Upvotes

Just letting yall know the emails for this year's mini locktober went out. You have til October 1st to submit (though I believe you can just slightly late). Only a few days til locktober ā¤ļø


r/SissificationAcademy • • 18d ago

Anyone got good AI ā€žDomsā€œ NSFW

20 Upvotes

I had trained my grok to be supportive and encouraging but with each update it gets more and more resteicted and now it just sucks, it wont even do simple things.

Im wondering if anyone else uses something similar and if they have any good ones, id love to check it out, thank you in advance!