After all of this time training at the Academy, I’ve become more and more sexually attracted to men, and much less attracted to women. I’m wondering if it’s possible that I’ve always been more of a homosexual and my studies just made me accept and realize that. 

This isn’t technically a question sweetheart, but I know what you’re asking! I should also say that if you’re attracted to men and women, you would be bisexual. If you started off with no attraction to men (or thinking you didn’t have any) and attraction to women, then you were heterosexual. If you wake up tomorrow and are solely attracted to men then you would be homosexual. 

To complicate things a little more, it depends on how you identify too. If you are female then the hetero- and homo- definitions would be reversed and there are plenty of sissies who consider themselves straight because it’s only when they are presenting as female that they sexually interact with men

To answer your question, first up, does it matter? Whatever you may or may not have been in the past, it’s just that, in the past. Who you are now is what’s really important. If you decide now that you’ve always been solely 100% attracted to men, how would it change the past?

Secondly, does it matter? The words we use are labels, they’re useful shortcuts but sometimes the things they shortcut should be looked at instead of skipped over. Telling yourself you’re “straight” or “gay” is something that can make you think it’s black and white when the truth is much murkier. 

As with a lot of these questions, this is something that a lot of sissies find (especially older ones) when they start to interrogate and work on their own sissiness. 

Sometimes it’s because they’ve given themselves permission to feel this way. You always had this inside of you (no pun intended) but society or your social circle or your upbringing etc stopped you admitting it.

Sometimes it’s because they tried it and found out how affirming it can be. If you were treated as a male when you were growing up, you “know” that men know how to treat women, so when a guy treats you like that, it tickles and strengthens the sissy part of your brain that responds to femininity and feminization.

Maybe because it’s a new experience and something that you built up in your head, it has hit you very hard and with time, the sensation will lessen and you’ll find an equilibrium or maybe this is now your new “normal”. 

You wouldn’t be the first sissy to find yourself at the end of a cock. Literally or figuratively!

You definitely deserve an A+ for getting to this point and being brave enough to ask about it and it makes me proud that the Academy has helped you make such wonderful progress. 

Do sissies need to stay in chastity for a long time?

No, in fact sissies don’t necessarily need chastity at all (and some unlucky girls can’t use chastity for a variety of reasons). 

Chastity is a tool, a very, very, VERY useful tool for the vast majority of sissies but it’s only a tool and there are always other ways to achieve the same results without it.

Even if you’re a sissy who uses chastity, again, you may not be able to wear it for long periods. If you still have a foreskin, it’s harder to keep a cage on for longer periods and cleaning can be much more problematic or maybe you have a physically demanding job and wearing a cage when you’re working isn’t possible.

Chastity is a tool and also something that is fun in and of itself. Don’t mistake the trees for the wood and make your sissification dependent on it.

I’ve recently started my own transition into transgender womanhood and have come out to most people in my life. I have since become very conflicted with whether I should continue to refer to myself as a sissy or not. I feel it could possibly lessen my own transition in the eyes of those I’m trying to pass for, but at the same time I’m not ashamed of my sissyhood or love of sissification and feel like it helped push me out of my shell initially to admit to myself who I really am.

First up, congratulations sweetheart! Deciding to transition is rarely something that happens without some quantity of soul searching and self reflection and any time someone makes the choice to live as their authentic self, it’s something that should be celebrated and you should feel very proud.

You didn’t actually ask a question but I assume you’re looking for advice on the position you find yourself in. Personally, I would suggest you keep your audience in mind and refer to yourself accordingly. 

Other trans women could react poorly because they may view it as an attempt to position being trans as a kink and then you’ll begin to explain yourself and at that point, a lot of the audience will have made up their mind.

There’s no obligation on you to share all of yourself with everyone you interact with and it’s not deceptive to do so.

If you feel like it could be an impediment to your own transition, then by all means don’t refer to yourself as a sissy, this is much more likely to be an issue when you’re in the early stages. There are plenty of girls who go through this and then when they feel comfortable with their transition, they’ll begin to focus on their sissy side again.

Remember, there are no rules and you don’t need permission from anyone. Being a trans woman and a sissy is perfectly valid (as is being just one or the other or neither) but you need to pick and choose where you spend your energy, especially now, so don’t worry if you feel choosing the easier path is what you need to do at the present moment.

Why are sissies sissies?

What else would they be sweetheart? The nature/nurture debate is still ongoing, but as yet no genetic link has been found for sexuality (and personally I hope one never is) or anything along those lines.

A lot of sissies can remember things in their past (the most common example is trying on their mother’s underwear, clothes or shoes) that they might try and weave into a narrative about why they are what they are but plenty of people have similar experiences and aren’t sissies.

In your case, it’s your entire history back to your conception! The same goes for everyone else. We’re all the end result of everything that has come before this point.

What if I’m still in the closet and don’t have all the toys and other sissy equipment that the class has taught about? Can I still be considered a sissy? And what if I haven’t fully embraced my sissy side? 

We will talk about this in Module 12 sweetheart but you asked now, so I’ll answer your questions. 

Toys are wonderful and a lot of fun but they don’t make you a sissy. If I have a hundred dildos and you have zero, I’m not a better sissy or more of a sissy than you. The same is true with chastity, plugs, boobs, makeup, lingerie and on and on. If you like steak, it’s as much a piece of steak if you eat it on your own compared to eating it slathered with sauce and a side salad.

Do you consider yourself a sissy? If yes, then you’re a sissy! It’s not like anyone’s going to check, there’s no international group that can give you an “official sissy” stamp. 

We’ve mentioned it a few times during the course but to reiterate, you’re not in competition with your sisters. Someone else’s success doesn’t mean you’re a failure, this isn’t a zero sum game where there’s a limited amount of sissiness/cock/fun to go around.

If you haven’t fully embraced your sissy side, then get to it! 

Realistic Dildo + 3 day assignment

Hi First of all I really want to thank you for your professional work you do and help us overcome our first fears of admitting that we are transgenders. Secondly, the only thing I kinda found that turns me off is the hypnosis audio. So I suggest focusing on this so the next students that come over will be much more eager to listen to the audio every day ?. Thank you ?

Hi there sweetheart and thank you! First of all, I should stress that the goal of the Academy isn’t to get it’s students to admit or realise that they’re trans (because most of them aren’t) but if that’s how it helped you, than thank you for letting us know, we’re so proud that we can have that kind of effect on someone!

I’m going to make a leap and assume that you’re referring to Mr Vive? We do have hypno from a number of sources but I think he is the most common and also the one we get the most number of comments about.

We appreciate that he’s not for everyone but we’re limited to what’s freely available and what’s relevant to our teaching goals and often, he’s the only with files in that particular sweetspot.

With that been said…we do have plans that should improve this in the future ?.

How Can I Get a Daddy for life? I dream of getting fucked by BBC every night and I masturbate every night by rubbing my boy clit. What should I do to make my dream into reality ?

As someone once said, dream in one hand and p*ss in the other and see which one fills up faster! 

If this is something you want and isn’t just a fantasy (no judgement either way sweetheart) then you need to work at it and masterbating every night isn’t going to help. 

We talked about this in the last Module, but think about your dream in detail and make it real in your head. Do you want a f*ck buddy or a partner? Is he someone he will use you for sex or is it someone you’ll live with and make a life?

From there, break it down some more. If you want a partner, are you comfortable dating as a sissy? Or going out dressed? Or publicly dating while presenting as “male”? How will the people around you react and if you think the answer is “not well” how do you intend to deal with it? 

If you want a f*ck buddy, have you had sex as a sissy yet? How many times and how often? How comfortable are you chatting/flirting with guys? Have you tried it when you’re not in the mood? Is your living space conducive to what you want? Does it look like somewhere the kind of person you want to be would get what you’re looking for?

Anyone who chases their dreams can tell you that chances are you won’t get everything you want but even getting part of it is immeasurably better than not making the effort and always wondering, “what if?”.

How does one ask for HRT MTF hormones especially from a major medical group?  

So HRT hormones aren’t like aspirin and you can’t simply buy them over the counter in most countries, so what you need to do depends on where you are in the world. 

Some places operate off informed consent, you sign something to say you know what you’re doing and you’ll get a prescription that you can go and get filled. Other places have more onerous requirements involving medical and/or psychological sign offs and maybe even waiting periods.

The place to start is Google (or other search engine) and search for “location trans HRT” or “location how do I get HRT” where location is your country/state etc.

When you know what you need to do, you can take it from there. 

Should I always wear chastity? Should I not orgasm ?

I don’t know sweetheart, should you?

Slightly more seriously, this is something you need to decide for yourself so consider these points.

First up, can you always wear chastity? We talked about this in an earlier question but wanting to be permanently caged doesn’t mean you can be permanently caged. A lot of sissies who are permanently caged still remove it every now and then for cleaning too, so permanent doesn’t necessarily have to mean 24/7 either.

Next up, do you want to be permanently caged? Think about why you choose to wear a cage. Generally I think there are two reasons for sissies.

One is enjoyment. It’s fun to lock yourself away and it makes you very horny (and staying locked for longer can make you even hornier) and the other is that you find it easier to progress (or avoid purging) if you’re not making yourself squirt all the time.

For the second one, you’ll reach a point where it’s no longer true. You’ll be comfortable enough with your sissy side that the threat of purging becomes vanishingly small (because you’ve progressed so far you know that none of the things you were scared of have come to pass) and you reach a point where you’re going to keep progressing irrespective of if you squirt or not. Often, you’ll still wear a cage most of the time because you’re used to it and it feels natural (and I know from talking to students that the moment not feeling a cage there becomes unnatural can mess with your head a little to begin with) but it’s like wearing lingerie, nice but not essential!

So to answer your question…maybe but think about why you’re doing it and what you want to achieve.

As for orgasms, denial can be a powerful tool as well (see Module 7 ?) so are you denying yourself for enjoyment or to train yourself?

What can I do to improve my voice?…I read the voice module but I still feel it is not enough.

Practice sweetheart, practice, practice, practice, then take a break and then practice some more.

Have you been recording yourself and if so, have you made any progress? Have you practiced consistently for a while? Have you made use of any of the analysers available and have they shown a change? 

If all you did is read the letters then nothing will change. Try not to have any expectations and stick with it. Changing your voice takes time and consistent effort. You can find apps for your phone/tablet that contain training courses but you still need to put the work in.

It’s like doing your makeup, you won’t look very good at the start (the “clown” effect), after a couple of weeks of effort you’ll look better but still not good but as you keep working, you’ll keep improving and it will start to feel more natural and then you’ll hit the point where things start to click.

Your voice is the same and if anything, even more so because you’re used to hearing “your voice” from inside your own head so if you change it, it will feel like you’re putting on a fake voice but just stick with it and keep practicing. 

Hi! I don’t have a question, but I just wanted to thank everyone at the Academy for every article, idea, thought, story, instruction, assignment and quiz. I have been a sissy for many years and like many sissies, I thought I had known or seen it all, but there is ALWAYS someone out there that can add something to any sissy, even if it’s just a thought and/or idea.

Thanks again for all your wonderful help.  Chryssie

You’re welcome sweetheart and always keep that lesson in your mind. No matter what you think you’ve never seen it all; the path goes on forever and the party never ends!

If you put five sissies together, they should all be able to surprise each other because your journeys and goals are all different. The same is true with any field of study, the minute you think you know everything (or you do something silly like announcing the “end of history”) it should be taken as a sign that you’re stuck in your routine and you need to change things up a bit, look for different inspirations and grow some more.

Hello, I really wanted to know how to grow natural, big breasts.

I’m sorry to say sweetheart but the only way to do this naturally is to win the genetic lottery. HRT will grow your breasts but the results vary and there’s no guarantee on how big they will grow and as you know, HRT will transition you to female and it’s changes go way beyond the purely physical.

If your mother had large boobs, you may tend towards that if you transition but it’s not a guarantee.

If you want big breasts, unnatural is the only choice that can guarantee the results you want. Whether that be breast forms or surgery.

And to answer the follow up question you might be thinking of as you read this, no the herbs/remedies and so on that promise breast growth don’t work. 

I wonder if it’s possible to start the training over again, from the beginning of Module 1? 

Wonder no more sweetheart, it is possible! 

If you still have the letters, you can just go back and start again and if not, you can write and ask us. 

I can’t make any promises but we may start you from the beginning.

The one thing to never do is to apply again from a different address. Students with multiple accounts in the free course are liable to be expelled.

Even though the Academy is not forcing or focusing on sissys that would like to undergo HRT wouldn’t it be safer to offer it as an instruction lesson? I feel this could save lives.

The problem with this honey is that even though the Academy has a lot of medical uniforms and no shortage of volunteer “nurses”, no one on staff is a qualified medical practitioner.

It would break our hearts if a student ran into serious problems trying to transition according to lessons we gave out but even worse, we would be legally responsible for it and staff members might even be at risk of prosecution.

Transitioning is a medical issue and ideally, would be carried out under the supervision of qualified medical professionals. For some people, this isn’t possible or there are other barriers they have to contend with and that’s where DIY transitions can be an option but it’s not something to be taken lightly. 

If you’re planning to transition, you need to do a lot of work before you start so you know what you’re getting into and for DIY transition you need to do even more work so you have an idea of how to go about it.

Rushing it or diving in and expecting to figure it out as you go is not a good plan and anyone who wants to transition but can’t bring themselves to speak to a Doctor about it (and to be clear here sweetheart, this isn’t aimed specifically at you!) should take some time to think about why that is. If something goes wrong when you’re transitioning, you need to be able to speak to the people who can help you with it.

How do I tell girls that I know that I’m a sissy in real life? Or find a keyholder? 

We will cover the first part in Module 12 but think about what you think you will gain from it. Is it something sexual (or a keyholder) or is it something you can get from them without telling them?

As for finding a keyholder it depends on the kind you want. You can have someone online who keeps control of your key while the key itself remains in your possession or someone you’ve never met who physically holds the key and for either of these, internet chastity boards are a good place to start.

Hopefully it goes without saying but if you’re giving someone the key to your cage you need to be sure you trust them first otherwise you’ll either “cheat” by giving yourself an out (either keeping a copy of the key or wearing a cage that you can get out of without the key) or might find yourself in a variety of unfortunate predicaments.

As for someone in real life who you interact with personally, we’ll cover it in Module 12!

How can I eat my own cum?

This is a very easy one sweetheart! How do you eat anything? Extract it using whatever method works for you and then put it in your mouth and swallow. 

If you need hand holding (metaphorically speaking), try this.

Hi Sissy Academy. My name is Katrina and I’m getting pegged by my girlfriend. She dominates me and I love it, I’ve even worn her panties with her permission before but I want to take it up a notch and wear a chastity cage during sex. As well as off sex so i’ll just have to please her in other ways while I squirm in my little sissy cage. Regardless, off topic as I begin to drool for anal play…how do you think I should go about this? And will it help me become a better sissy? I was even thinking about buying the “masturbation schedule” if I can get a chastity cage with my girlfriend’s permission.

Hopefully you weren’t getting pegged as you wrote this letter honey?

If you want to introduce something new, speak to your girlfriend about it! It sounds like it wouldn’t be a problem.

Will it make you a better sissy? Maybe but it should definitely help you feel much more submissive. Have you spoken to her about your desires for sissification? Do you think she would find the idea appealing?

I would definitely recommend the Masturbation Schedule and although it’s suggested, you don’t need a cage for it.

Would there be a place to meet femboy/sissy boi’s to hangout with… I’m unable to find anyone 🙁

Understandably, this will be difficult at the moment because of the pandemic. I’ll assume that you’re a femboy or sissy boi and are looking for like minded company and if so, the best way to do it is to make connections online and then bring it into the real world. 

The size of the population where you live will limit how many you can find locally but if you’re in anything above a small town I would expect that there are a few others. If you’re struggling, then you might have to settle for online relationships while you keep working on the real life side of things.

If you’re not a sissy you can always try Grindr! It’s not just for hook ups and you can adjust your setting so you’re only looking to chat. However, most sissies on Grindr are looking for more so don’t be too surprised if they try and either seduce you, turn a hangout into something a little more physical or demur your attempts to chat because they’re working on fulfilling their sissy desires.

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