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Version: 0.7.9

Journey Into Sissyhood

Journey Into Sissyhood has been in production since April of 22'. I am working alone on this project. It's a passion project for me, I'm trying to give people who fantasize about feminization, sissyfication and all that good stuff a game that they can relate to. I update the game every week or so, depending on the changes that I make.

If you like the game and want to play the latest version of the game please support me on


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Always read the changelog to find out how to get to the newly added story.



Journey Into Sissyhood is a story about a young adult that will be transformed into a beautiful sissy. You will have to face naughty decisions that will lead to either a life of being a good sissy or a life full naughty things, but don't be fooled, you can taste a little bit of both worlds if you choose to. 

You will be asked to take quizzes and tests, you will be forced to listen to audio hypnosis and watch hypno porn loops. 

Main character - you can name it how you want

Mother - you can name her how you want

Father - you can name him how you want

Mistress Sofia

(List will be updated as the story progresses.)

Journey Into Sissyhood - 0.7.9

*New story update for the slow transformation path

To get to the Paying off your dads debt story path - play the slow story path (the one where you don't become a bimbo - the answers from the sissy test will decide which path you will play) - when Mary asks you to work as a maid in the hotel, accept her offer, when you are fired from the hotel, accept getting fired

Added new story content for the slow transformation path

- added new progress to the story

-142+  new images and animations

-50 new background images and accessories

-new dialogue (6000 words)

-new punishments

-fixed a lot of spelling mistakes (thanks Candy)

Review by user210

Version reviewed: 0.5.9 on 10/25/2023

There is no corruption here. Why it is included in the tag?

MC already had interest in woman's clothing and took a serum which could have taken him to become his best self, and his best self was a woman. In one day he become from denying his desires to wearing girly clothes in public. There is no corruption here, you want to see a proper conversion process from boy to trap to femboy to sissy to trans woman, this is not from you.

All that being said, this game is for those who like Sissy/Bimbo elements. They don't care about the process but the end state and that's fine too. It is a game made to cater that type of audience. If you are one of those who don't like conflict of a MC forced into corruption and want to see quick fun this game will be a good experiance, enjoy!

Review by BKRW

Version reviewed: 0.5.6 on 09/16/2023

(Reviewed version was 0.5.5)


I tried out this game a while ago, and the beginning seemed a bit odd and forceful, so I stopped.

I gave it another try this last week, and I'm glad I did. So far there seem to be five main paths. (All five are still WIP)

I did the Slow Transformation paths first (as I assumed it was the main path of the game) and they're okay, all are pretty short. I did the Father Debt path first, and that was pretty fun. I did the beg for job path next, and I initially didn't like it too much, though it's nice when Jack gets his comeuppance. I do really like the character of Charlotte from both paths too. Then I did the don't do event path, and to be honest I didn't really like it, though it's extremely short so far, so I'll give it the benefit of the doubt as it's very WIP.

Then I did the Fast transformation paths. I really like Bimbo stuff, so I decided to save them, though I was afraid the Slow paths were the main ones. The initial path before it branches is quite fun, with all the computer activities you do, I just wish their were more lol. I then did the no store job path, and it was quite fun, though still quite short, and I greatly look forward to what will come from it in the future. 

Then I did the path where you take the store job. Consider me So Pleasently Surprised. As i've said before, I love bimbofication content (especially when paired with sissy content). And this path was SO GOOD. I was expecting a short, still greatly WIP path like the others. But this path has evidently received a lot of care and work. This path alone is one of the greatest peices of erotic visual novels I've EVER experienced. The path into becoming the ultimate Sissy Bimbo it follows is captivating, well written, and features both sex scenes, hypno scenes, and physical transformations. The character of Sofia is also quite captivating, and makes for a good domme, and I'd love to see more content with her. I was so pleasently surprised when this fantastic path kept just going on and on, and getting better and better as it did, although eventually it too did end (as it is also WIP). Still I think there's more content on this one path then any of the others combined, and most of it is very Captivating. I think with maybe even a few more tweaks, maybe some more training scenes with Sofia added in-between, it could be even better, but it's already a FANTASTIC story, and I greatly anticipate the contituation of it. This one path could easily be a Fantastic Game on it's own. But with it still being WIP, and the other 4 paths still being much less complete, this one Bimbo path's great story, writing, and images give me great optimism about the future of those other paths and the game in general. 


My one big complaint, or way I think it could be improved, is if there was a way to see your stats, (sometimes you get a prompt saying you got +1 to a certain stat, but that's it), as well as your current money (as that seems to play a role on some paths).


For a Visual Novel in Alpha, I think this shows great potential, and will be following it's development into the future. And if you're into both Sissy and Bimbo content, the Main Bimbo path is already long enough and fantastically written so that it will give you many hours of great enjoyment if you download it at this state.


Review by all4s4u

Version reviewed: 0.5.3 on 08/23/2023

I pulled down my last review.  I hate the haters, especially when they are unfair or flat out wrong about things.

Let them be on their misguided way.


Just want to say it is a great game/VN.  Light reading, straight to the point, fun, kinky, and updated on a regular basis.

I encourage you to support this game if it pleases you.  If you cannot support with money, support with good reviews, here, and on Itch.io.  

Thanks Lollipop Sissy!!!   Keep up the good work!

Review by CandiIsSweet

Version reviewed: 0.4.9 on 07/14/2023

The best way I can describe this game is-it'a a Jeep. If you're a Jeep person, you want a Jeep and nothing else. Other people may try Jeeps. Some will shake their heads and never come back. Others will go "not for me, but I understand the attraction." But for the Jeep person, they're happy as hell they've got a Jeep.


This game is about becoming a sissy. Either wilingly or forced, you're going to become a sissy. And if you love sissification, you'll be happy. It's got an audience, and it caters to it. Other people will either think it's weird or stupid, but it's not. It's a game for a particular audience, and for that audience, it succeeds in spades. It's also a game that's being constantly updated with new content and patches. Which, looking at how many games are stagant or abandoned, is a good thing

Review by Red-XIII

Version reviewed: 0.4.3 on 05/20/2023

Yup, tndvrs is totally right, it's absolutely blasphemous to complain about something when you can't produce better. 10 out of 10 bad musicians wholeheartedly approve of this wise philosophy.

We should also be grateful for whatever is given for free regardless of it's quality and scrap this review section completely while we're at it. I mean we're all grateful for whatever is free regardless of how bad it is, so who asked those stupid reviewers for their stupid opinions in the first place? Am I right or what?

Ahem! .. sorry, and with that I'm done being sarcastic, now let me get to the actual reviewing.


To cut on the length of it I'll start with simply stating that jizpiz was right. Neither art nor writing here are worth the consumer's time.

There's something that might be though. For the right consumer anyway. And it's where most of the authors effort seems to have gone thus far.

Looks to me like they've sunk a fuck-ton of effort into trying to breach the gap between the game and the player.

In a very very very very VERY single-minded and one-sided way.

Where normal games try to breach said gap by being vague and all-embracing, this one merely made an assumption that all their potential players share one psychological profile and started working from there.

Basically this is a game that assumes that the player is sissy or at least one in the making (which is actually quite insulting, if you think about it) and most of it's effort goes into merging the supposed player's kinks and insecurities with those of the character.

Does it work? I dunno but based on the positive reviews it's getting I would have to guess that yes?

Does it backfire? Yup, definitely I can attest to that personally. Freaked me right out. If I ever wanna get insulted and/or turned off I know where to look.


P.S. To the author and whatever other creators that are prone to falling for the similar mistaken assumption - please be aware that not everyone on this site likes the stuff we're fetishizing to the point of seeing it in a positive light or wanting to experience it personally. If it's hard to grasp - think of it like you would of dramas and horror flicks. Not everything people like to gawk at is something they would want any real people (themselves included) to experience.

P.P.S. I mean don't get me wrong it's your creative process and your choice of target audience, just keep in mind that not the entire site is the way you assume it to be and don't insult the rest of us by being so dismissive in your evaluations.

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