Himegoto

Similarites: Both cross-dress characters were force to join the club due to debt. Both involves cross dress main characters. Both have the same comedy and gender bender genre. Both cross dress character's serves as the club's dog. And both also have the same harem element. Dissimilarities: One cross dressed character from one anime was a girl, while the other is a boy. One anime has an extra romance genre while the other is more on comedy. One was a 26 episode and 23 minute long anime, while the other anime is more of an 12 episode omake. The cross-dress character from one anime was rescued by the student council members and paid-off his debt, while the cross-dress character from the other anime was duped into joining the club.  read more 

Crossdresser. LoveCom and Himegoto just feature crossdressers I thought were quite similar. They are secondary characters, but they still have lovability compatibility to them rather than just appearing for 2 seconds. With very different stories too, there isn't a lot to say other than they are quite funny and good at that when it comes to the genres they reside in. Not just saying that, they genuinely are funny at times. Great s.o.l and great shoujo romance anime I would recommend to anyone with a decent bit of experience in anime.  

Exploit. What I found similar about Boku no Pico and Himegoto is that both anime use their MCs in a way that is manipulated in an uncomfortable but lighthearted fashion. They play a dangerous game with what they are doing, quite easy to dislike the very concepts or representations given, but the similarity still exists and it is quite interesting to see how the two come together despite being of separate worlds. For whatever reason you watch these anime, both understand what people being exploited, mainly for erotic/sexual desires, can correlate to, maybe as far as the real world in some sense. Either that or watch these for the laughs.  read more 

Himegoto is about a cross dresser more so then a sex change but it's as funny if not funnier then Gokudolls ^^ 

Crossdresser. There is no real similarity in the story, they just both feature crossdressers that you may find yourself interested in. What I will say however is that it is possible to see the link between characters in these anime, with MCs being really hot on getting/playing with their said other that doesn't really want to be with them. It's a dangerous world out there but nothing that will make you detest the playful nature the two give. Good comedies I would suggest you watch as one of the best things in their respective themes, shoujo and crossdressing.  

It's almost as if ecchi anime based on shota simply exists to exploit them, though I am not one to question. Regardless, both Jugyou Chu and Himegoto are anime that find themselves having a young boy take up the female attire in order to make life with the people they reside with. Just excuses for fanservice, which is probably what most come for, to which I will say they are alright for the most part. Nothing too arousing, however, more so slapstick.  

Now, this recommendation seems a little wild, but it suddenly occurred to me that what you may consider living the life is not entirely true realistically speaking. Himegoto and Goddess Dorm follow two protagonists who may be having a little too much fun or, more accurately, are being played around a little too much. With ecchi treats everywhere, our two protagonists Koushi and Hime are sometimes in the middle of living a hard life because of a wild harem that does what they so please. Would watch both if you are into ecchi, in fact, these two anime, whilst not for everyone individually, help bridge a gap in ecchi. Free fanservice for all your needs regardless of who you are! :) read more 

Crossdresser. There isn't much to give but if you are looking for two anime with a crossdresser look no further. Other similarities include respectively good comedy in their worlds. You could even look at the two poking fun at their main theme, crossdressing and maid cafes. I find myself enjoying what is to be seen with the two, even if questionable content exists within the two.  

This is another fabulous "Trap" anime of a guy crossdressing and its also 12 mins or less per episode 

Himgoto and Otoko no Ko Ojousama are short anime about a boy who is frequently dressed like a girl while the girls in the anime *ahem* heavily sexualize him. Otoko no Ko, however, is much more graphic.  

the three main characters all have to dress up like girls and work for the student concile sort of and its funny as shit 

The main character must be dressed as a woman because there are a few "terms" in which MC must fulfill by any means and only accomplish with this conditions 

Both have cute cross-dressing boys 

Both are comedies setted at school where main character is a boy surrounded by females and is frekvently being force to change into a girl. While in Himegoto he only crosdress, in Kampfer he changes completly. Kampfer has also more action. 

Both involve the main character who was originally male being forced to live as a girl for one reason or another, while Onimai is a full change to a girl Himegoto is just (very persuasive) crossdressing though. They both have a large portion of comedy but Onimai is able to build a more coherent story and do more in story/drama aspects since it has a full season while Himegoto is a short. I'd say if you enjoy the concept of genderbend in general you will probably enjoy both shows. 

Both are comedies about the main character as a boy who frequently cross-dresses, and has no-face parents who put their son in unimaginable debts, and are chased by debt collectors. They both end up falling into money, and end up working as a gofer for the people who saved them from their debts. The only difference would probably be the contrast in length. Hayate no Gotoku is a full-episode series spanning multiple seasons, while Himegoto is currently only one season, with only 4-minute shorts.  

Similarities: -Short episodes -Quirky and fun -BL themes -Crossdressing -Light, bright colour pallet (more so in Himegoto but both are nice) -Easy to get hooked on (and quick to finish) -Fairly nice OST (the Fudanshi OP is one of my favourites) -Male protagonists embracing commonly feminine interests  

First we have a cute male MC, been forced to use women clothes (diferents amounts of time, but you got the idea) also very funny, ofcourse, its posible that the genders might be a little far way, but should give it a try.