At age five Cecilia Sylvie has a traumatic, world-shaking realization: she is the villainess in an otome game! One where it’s very easy for even the heroine to get stuck on a dark path and face a grisly fate! Cecilia is determined to avoid the fate of the villainess at all costs (and also does not want the fate of the heroine either, “become a Holy Maiden” and be restricted to that role for life? No thanks!) so clearly there is only one solution to this: cross-dress as a boy since a boy can be neither a Holy Maiden nor a villainess!
There are quite a few elephants in the room to address for this series (frankly it’s less like a room and more like a zoo with how many there are here) with the first and in my opinion the biggest being: how has absolutely no one figured out that Cecilia is cross-dressing at school? Yes she has Gilbert helping her out, and I suppose it’s not entirely impossible that some of the Sylvie family staff have figured out (assuming that they are doing her laundry when she comes home on vacations) and decided not to care, but it’s a bit hard to believe that she’s been doing this for years with no slip-ups.
At school she isn’t “Cecilia Sylvie” but “Cecil Admina, a baron’s son”; “Cecilia” is enrolled in the school as well technically but since she’s supposedly too sick to attend, where on Earth do her parents think she is all the time, this is a boarding school after all! If the story was to reveal that her parents were fully aware of her antics the whole time that would honestly make the most sense (and “the mother is seemingly eccentric but knows much more than she lets on” is a trope that crops up a lot in this kind of story) but so far we haven’t gotten an explanation and I’m not sure when we will.
It’s true that no one expects airtight plotting from fluffy romcoms but considering that this is the basis of the story (and Cecilia has only come up with this batty idea because her life is on the line), I would expect a bit more in way of explanations, even if they were just hand waves. Yes Cecilia has confided in Gilbert about her memories about her past life as an otome gamer (much like the role Adi plays in Young Lady Albert is Courting Disaster), but Gilbert is also just a teenage boy and not a master strategist. I’m also not the biggest fan of him since he has a huge crush/sister-complex regarding Cecilia (even though they’re biologically cousins more or less, he was adopted into the family at a young age so they’ve truly grown up as brother and sister) and I’m just not a fan of even implied incest. This dynamic, and the way that Cecilia’s marriage with Prince Oscar will probably go through in this reality, remind me a lot of My Next Life as a Villainess which both Krystallina and I pointed out in our review of the first volume of the manga. The plots are fairly dissimilar, even if a few of the characters and their dynamics are, but I can honestly say that if you liked one and aren’t sick yet of villainess stories that you should check out the other.
Cecilia does seem to have reincarnated into a darker otome game than Katarina did however; quite a few of the male love interests have dark, broody pasts that could get the heroine (originally Lean but now seemingly Cecilia) killed and since Cecilia sincerely does not want to get the heroine’s good ending either she’s running out of end game options! Cecilia hopes to foist these Holy Maiden duties onto someone else (since even in the original game, Cecilia wasn’t the only candidate for the role) but she’s had no luck so far. In fact, by the rules of the competition, Cecilia is secretly in first place! It’s definitely funny to watch Cecilia bumble and struggle her way through this mash-up of game routes (especially since she died before she got to play all the routes) and there are plenty of other funny moments as well, like how Lean has turned out to be a full fujoshi and both can and will use the cast around her as the models for her bestseller stories.
Cross-Dressing Villainess Cecilia Sylvie definitely does a few things I had been hoping to see in an otome isekai series (like having multiple reincarnators, although it’s certainly not the only story to have used this idea) and it’s certainly not a boring bit of fluff to read, although if it overstays its welcome that feeling could change very suddenly. Ideally, I’d like more of the main cast to be in on “Cecil’s” secret (I at least think there’s still plenty of potential for comedy that way) just so I can stop yelling at the characters to realize that they’re in a silly otome story. Stories work with at least some sort of limitation on them, even comedies, and at times it feels like the Cross-dressing Villainess is about to collide with these boundaries too hard and break everything in the process.