The Masculine Mystique

Male Protagonist, Female Protagonist, Trans Protagonist, Text Based, Anal Sex , BDSM, Big Ass, Big Tits, Blackmail, Bukkake, Cheating, Corruption, Creampie, Dilf, Drugs, Exhibitionism, Female domination, Futa/Trans, Gay, Group sex, Groping, Handjob, Humiliation, Incest, Interracial, Lesbian, Male Domination, Masturbation, Milf, Multiple Penetration, NTR, Oral Sex, Rape, Romance, School setting, Sex Toys, Sexual Harassment, Sissification, Spanking, Stripping, Swinging, Teasing, Titfuck, Transformation, Trap, Twins, Vaginal sex, Virgin, Voyeurism

1. Extract and run the .html file to start playing in your browser.

UPDATE 0.9.7a: Fixed some bugs.
UPDATE 0.9.7: Did some work on Belinda comedy club date. Miscellaneous other changes and additions. Note: You may need to replay old save games before going on the comedy club date for everything to work properly.
UPDATE 0.9.6a: Fixed a bug.
UPDATE 0.9.6: Finished Wednesday night Emily path. Some other fixes and tweaks.
UPDATE 0.9.5d: Some tweaks to the CSS kindly provided by TheMadExile to make the game work better on mobile devices.
UPDATE 0.9.5c: Fixed <<unset>> bug.
UPDATE 0.9.5b: Many technical updates for Twine 1.4.2 and also to split the game file and reduce the size of the variable store. Some minor changes to paths and some paths extended to a very small extent.
UPDATE 0.9.5a: Fixed some bugs, including the Internet Explorer bug from the last release. Some Emily paths extended.
UPDATE 0.9.5: Renamed Melody to Emily. Emily “date” greatly expanded, but not fulld. Previous saves for that path unlikely to work. Bugfixes for Belinda dance club date and Billy date. A very small amount of progress on the chastity belt path on Billy date. Gated off cursing out Mrs. Anderson. Can be restored by turning it on in the Options menu. Added an option to change to white text on black background for those who prefer to play in very low light. Save game files will probably need to be replaced. You may see very strange behavior if you try to use previous save game files with this release, particularly on Melody/Emily paths.
UPDATE 0.9.4: Some extension to Mr. Hilliard/Chief Johnson and Melody paths.
UPDATE 0.9.3f: Update to resolve some issues with the options menu.
UPDATE 0.9.3e: Fixed some bugs.
UPDATE 0.9.3d: Fixed a bug.
UPDATE 0.9.3c: Test of “options” menu. No new content.
UPDATE 0.9.3b: Only very minor bug fixes and changes.
UPDATE 0.9.3a: Fixed a logic error.
UPDATE 0.9.3: Extended Billy’s date. Still not full.
UPDATE 0.9.2: Finished all loose ends on Julia path. Implemented capability to skip age verification and preferences screens.
UPDATE 0.9.1b: Fixed a typo and a noticeable bug. New builds of SugarCube and Twine.
UPDATE 0.9.1a: Fixed a few bugs.
UPDATE 0.9.1: Extended Billy path through Mason’s date. Some changes made to some early scenes. Bug report revamped to condense information. Various technical improvements to Twine which may cause some issues, particularly with regards to the font for the title.
UPDATE 0.9.0a: Fixed a bug. Included new update to SugarCube and started some cleanup of variables.
UPDATE 0.9.0: New update to SugarCube. Meant to fix an error with Internet Explorer which gave continual popups due to lack of storage space, problems with colored text, and “rewind” issues for browsers with limited history space. Saved games should now transfer to future versions of the game barring future changes to paths or variables. Very small addition to Billy date path.
UPDATE 0.4.10i: Fixed an annoying bug.
UPDATE 0.4.10h: Extended some of Billy’s date. Added a new bug reporting method, plus one surprise.
UPDATE 0.4.10g: Fixed an annoying bug.
UPDATE 0.4.10f: Redesigned the chastity belt path and options.
UPDATE 0.4.10e: Some bug fixes and improvements on the Billy “stay male” path.
UPDATE 0.4.10d: Made it possible to take a path where you let Billy have sex with you, but don’t automatically become female.
UPDATE 0.4.10a-c: Minor bugfixes for new content.
UPDATE 0.4.10: Started Billy’s date. Many code cleanups, bug fixes, and small changes. The new SugarCube header should enable saving as files and restoring as files for people who can’t keep bookmarks in browsers or want to swap saved game files.
UPDATE 0.4.9e-i: Beta-test of TheMadExile’s new SugarCube header.
UPDATE 0.4.9d: Made some fixes to the sexual history table.
UPDATE 0.4.9c: Fixed a couple of very minor bugs.
UPDATE 0.4.9b: Fixed a couple of bugs. Added a table for “sexual acts” variables.
UPDATE 0.4.9a: Fixed a path-breaking bug.
UPDATE 0.4.9: Finished date with Molly. Extended loose threads in Julia date path, but did not finish. Made a number of small changes to a number of small scenes and fixed some bugs. Added personalized submission stats (visible on the stats menu) for various characters in the game. Added an age verification screen.
UPDATE 0.4.8b: Fixed a few more bugs.
UPDATE 0.4.8a: Fixed a couple of path-breaking bugs.
UPDATE 0.4.8: Wrapped up dates with Sean, Rachel, and Belinda to reach Wednesday’s end state. Extended the loose threads in both the Julia date path and the Mr. Hilliard and Chief Johnson path, but did not finish either. Fixed some bugs.
UPDATE 0.4.7: Date with Julia mostly full.
UPDATE 0.4.6: Wednesday date with Ethan included.
UPDATE 0.4.5b: Finished Belinda’s date at the club. Fixed a couple of bugs.
UPDATE 0.4.5a: Fixed a couple of bugs.
UPDATE 0.4.5: Added more of dance club date with Belinda. Still not full.
UPDATE 0.4.4c: Fixed a few bugs. Added the beginning of date with Belinda to the dance club for bug-testing purposes.
UPDATE 0.4.4b: Fixed a small bug in new content. Added FAQ.
UPDATE 0.4.4a: Added a scene on Sean’s date if you were wearing the chastity belt. Finished dinner scene and set up after-dinner options (mostly dates).
UPDATE 0.4.4: Fixed a couple of bugs. Sean’s date full.
UPDATE 0.4.3a: Fixed a couple of bugs.
UPDATE 0.4.3: Finished date with Rachel, some extension on scene with Mr. Hilliard, some other small changes.
UPDATE 0.4.2e: Fixed a number of bugs. Some small additions in content.
UPDATE 0.4.2d: Fixed a number of bugs.
UPDATE 0.4.2c: Filled in all placeholders for makeover scene. Finished Mr. Wegman/Billy path on Tuesday night. Turned off fades as an experiment and also added a font for the title and author, just to test it out. (Bonus points to the first person who can tell me what classic TV show the font comes from.) Made a few bug fixes, typo fixes, and textual corrections. Made a slight change to the timid, but resisting spanking scene with Rachel on Tuesday to make it more obvious that struggling against Rachel after the spanking will actually yield dividends (i.e. stop Rachel from abusing you, if that’s what you want).
UPDATE 0.4.2b: Changed the piercing scenes around quite a bit. Added text for navel piercing and changed quite a bit of the other text. Added a sidebar button to see the version number (not strictly necessary, since the files have the numbers on them), but then forgot to update the version number anyway.
UPDATE 0.4.2a: Fixed a couple of bugs.
UPDATE 0.4.2: Altered scene with Rachel in Tuesday’s gym class, added incest switch, added scene with Mr. Wegman on Tuesday’s Billy class (infull, but connects back to the main branch through placeholder text), added a scene with Mrs. Anderson on Wednesday afternoon (infull). Changed “Examine you” on sidebar to “See stats.”
UPDATE 0.4.1d: Added choices to the “Sean in the shower” scene, added interaction with Molly on Wednesday morning given certain conditions had been met at the suggestion of Bobmarquis2002, new variables in place which are visible for debugging purposes.
UPDATE 0.4.1c: Reinstated some of the “reluctant makeover” path, fixed bug with Melody.
UPDATE 0.4.1b: Corrected some bugs, added an “Examine me” command to the sidebar, added a second “back” macro to the with-stats “You” passage, altered the Mrs. Anderson makeover scene to modularize it and so that acceptance of the makeover automatically leads to accepting femininity (and therefore transformation), and added a “forced transformation” scene within the Mrs. Anderson options.
UPDATE 0.4.1a: Corrected “missing endif” bug.
UPDATE 0.4.1: Added a scene with Melody, fixed the “toys” bug, added a few more tracking variables, conditional text added to some parts of the Rosalind scene.
UPDATE 0.4a: Corrected a fairly major inconsistency in the Rosalind scene.
UPDATE 0.4: Fixed a few bugs. Finished getting home from school and a scene with Rosalind. Added an “Easter Egg” scene.
UPDATE 0.3.5: Fixed a few bugs and cleaned up some scenes. Finished detention.
UPDATE 0.3.4: Fixed a couple of bugs. Finished almost all scenes up to detention.
UPDATE 0.3.3: Added “you” links to a couple of passages which were missing them. Finished the entire gym path so Wednesday is now finished up to the point where gym class is over. (Still have some scenes in Miss Beaumont’s office to write.)
UPDATE 0.3.2a: Fixed a couple of bugs in girls’ gym paths.
UPDATE 0.3.2: Fixed a small amount of text. Almost finished all of the Wednesday girls’ gym class scenes. Circled back and extended or finished many of the dangling threads from boys’ gym class as well. Still some dangling threads and a couple of sex scenes which abruptly stop because I haven’t finished writing them yet. Fair number of new sex scenes.
UPDATE 0.3.1: Fixed some bugs, typos, and style problems. Tweaked one of the new scenes from version 0.3. Added some new scenes from Wednesday girls’ gym class. Only one new sex scene, though. Hasn’t had as much alpha-testing as I normally give it. May include some bugs.
UPDATE 0.3b: Fixed a bug which was causing some paths not to fully transform which should have.
UPDATE 0.3a: Fixed bug which accidentally locked off Ethan’s date for some paths.
UPDATE 0.3: Fixed some bugs. Changed logic so Masculinity drops to zero if Parker explicitly accepts her femininity. Added scenes in boys’ gym class up to locker room, including two new sex scenes, though they may be hard to find. Mostly meant as a bug-test release. The logic change for the Masculinity drop has some knock-on effects which hopefully I caught.
UPDATE 0.2.4a: Fixed a bug which automatically sent you to the dress up scene after full transformation, even though it was possible to fully transform without Mrs. Anderson’s makeover on Tuesday night. Added option to move to girls’ gym class if Parker is still in boys’ clothes, still in boys’ gym class, but has accepted her femininity.
UPDATE 0.2.4: Fixed a few bugs and typos. Moved Molly’s dialogue about “community girls” to Belinda earlier in the game, so it appears in the main trunk. (I want to be able to use the term without determining if Parker and the reader will need it explained.) Fixed mirror problem with Mrs. Anderson’s makeover pointed out by Bobmarquis2002. Added scenes for Wednesday morning up to gym class. This is a bug-test release. The code is now more complicated and I’m looking for story inconsistencies in the new material and I want to be sure everyone is properly sorted for gym class.
UPDATE 0.2.3: Fixed some bugs, typos, and other infelicities. Finished the Billy path so all paths in the game get to Wednesday morning. There is a tiny amount of a scene on Wednesday morning in some paths, but not really ready for release. I just didn’t feel like Patreoning it out. This update is really not worth downloading if you already have 0.2.2 or 0.2.2a, unless you’re really interested in how the Billy path resolves. Note that there are big flashing warning lights in that path telling people not to take it, because I was planning really bad things, but ultimately I’m a big softie and nothing too bad happens (in fact, it’s actually a pretty good path for some players). I’ll probably eventually go back and fix that so the warnings aren’t quite so ominous.
UPDATE 0.2.2a: Fixed bugs about hair, makeup, and nail polish. Reworked parts of the gym scenes (both boys’ and girls’). Added a different aftermath to the Sean in the gym scene at the suggestion of Visiter. Fixed some typos and other errors. Extended the Tuesday night cliffhanger scene somewhat.
UPDATE 0.2.2: Added back description of Parker’s manhood before Process begins. Changed options for what to do after calling Melody (can now call Billy or do trig homework). Small change to pre-Day 1 text to show Parker and Ethan are both horror movie fans. Added bit about Parker decorating his room with horror movie posters. Changed or added a few lines of text here and there in scenes as suggested by (and occasionally written by) Visiter. Fixed some bugs with variables either not updating or not reporting properly. Added some bookmarked scenes which can be reached through Rewind button. Removed loss of dominance in Rosalind’s kiss scene. Added a new “continue” button at the beginning so player has a choice whether or not stats display when looking at “You.” Added a dinner scene and a number of after-dinner scenes to bring story up to Wednesday morning (with one possible cliffhanger on Tuesday night).
UPDATE 0.2.1a: Added scene with less options for highly submissive players during the makeover on suggestion by Fun Times. Added dynamic description of Parker in “you” links. This has not been thoroughly alpha-tested due to the large number of possible combinations. Feedback and bug reports would be helpful.
UPDATE 0.2: Added scene at end of scene in Miss Beaumont’s office, due to suggestion by Visiter. Added small interaction with Rosalind after first day breakfast due to suggestion by Fun Times. Added many after-school scenes on Tuesday (Day 2) to bring story up to dinner time on Day 2. Removed gain in sluttiness when submitting to Rachel in locker room, due to suggestion in PM. Some changes to introduction to give clearer view of Parker’s character immediately. Some changes to text after fighting Sean in boys’ bathroom, written by Fun Times and shamelessly stolen by me. Miscellaneous other small changes here and there.
UPDATE 0.1: Not a lot of new content, though there is some small amount of new content since I first put up the game, but nothing to be excited by except in a slight cliffhanger sort of way. Per a suggestion by Drpwrites, I have moved Rosalind (Parker’s mother) offstage for now, so nobody wonders why they don’t get an option to try to talk to her. Fans of hers need not worry as she will be back. Introduced a new character, Molly the chauffeur (who was briefly a gardener in some available versions), though she doesn’t do much so far. Please let me know if I missed a reference to Parker’s mother which no longer makes sense.

The name of the story/game is The Masculine Mystique. It was written in Twine, but you don’t need to download anything to play it. It plays in your web browser and should play in any web browser. (UPDATE: There seem to be a problem with IE8 and I don’t know how to fix it. Upgrade to IE9 or try Firefox or Google Chrome or another browser and hopefully you’ll be able to play it.) It’s more of an interactive story than a game, though it does include a lot of gamelike elements. (The story tracks statistics which I currently allow you to see when you’ve finished playing through along with an explanation of how they are used.) These statistics have the effect of occasionally opening or closing off options to you or determining the result of a choice. So, for example, if you try to order somebody to do something, but your dominance stat isn’t high enough, you won’t be successful. Or you might refuse to do something, only to find that you’re too highly submissive already and no longer have a choice.
This game’s focus is on male to female gender transformation and no other types of transformation will occur in the game, even if requested (since it wouldn’t fit into the logic of the story’s universe). The game is certainly X-rated, probably XXX-rated. There are quite a number of sex scenes in the game, though it is possible to play through avoiding all of them. The story is now almost 280,000 words long, which is the size of James Joyce’s Ulysses (though one playthrough won’t get you a story nearly that long).
Here is a verbatim quote from the story/game’s opening passage:
“This story contains extremely explicit sexual scenes with heavy BDSM and humiliation themes: content includes oral, anal, M/M, F/F, and group, some semi-nonconsensual or even outright nonconsensual, and male to female gender transformation. The player can usually avoid engaging in most of this content most of the time. Note that it also includes some extremely politically incorrect and potentially offensive opinions and examples of gender relations which do not necessarily reflect the views of the author, who considers the setting of the story to be a fantasy universe and not the real world. Be sure that this is something you want to read before continuing.
“Finally, all due apologies to Betty Friedan for the story’s title.”

This is a gem.
The game is unfortunately abandoned because of understandable reasons (look up if you are interested in the developer), but it is definitely a highly regarded classic. I am surprised it isn’t on F95 already.
I highly recommend you play this game if you are into what the game offers (see the tags).
Note that many of the tags are optional – the game isn’t too restricting in your freedom, so you can relatively direct which way you want the story to go.
Although unfinished, the writing is excellent and the game is quite long, so it unfortunately leaves you wanting for more…