Yubisaki Milk Tea

Yubisaki Milk Tea is a manga by Tomochika Miyano that ran between 2003 and 2010. It should originally just have been one volume, but it ended up with ten.

Yoshinori Ikeda is a high school boy who works part-time as a photographer. One day Yoshinori's older sister Miki has to model for the latter as a bride, but forgets and runs off on a date instead. Yoshinori is dragged in and has to wear the wedding dress instead. After that he finds out that he actually likes to crossdress and begins to get more and more into it, creating a female personality, Yuki. But Yoshinori/Yuki gets into a complicated love affair when he falls in love with both his lively neighbor girl Hidari Morii and his classmate, ice queen and honor student, Minamo Kurokawa. Since Minamo becomes a home teacher for Hidari it doesn't take long before they both know about it. Things however get more complicated when Yoshinori's best friend, Wataru, unknowingly falls for Yuki, all while both Wataru and Hidari also have their own admirers...

Compare with Wandering Son, one of very few series like Yubisaki Milk Tea, to actually take crossdressing seriously.

This manga contains examples of:

 * The Ace - Wataru is a very good soccer player, and Nogi is the best on the basketball team. Which give them both problems, since both sports are team sports, where one player isn't enough to win a match. Wataru learn this the hard way, when he try to play despite being out of form, while Nogi have to face a boykot from her fellow players.
 * When it comes to studying Minamo is usually the best student of the year with Kodama as the second best. Minamo's teaching also make Hidari able to advance from the middle to the fourth best of her year.
 * A Cup Angst - Yuki admire Minamos big breast and complain that "her" own are small and fake.
 * Attractive Bent Gender - Yoshinori as Yuki.
 * Authority Equals Asskicking - Nogi is not only the captain of the basketball team but also it's best player.
 * The Beautiful Game - Plays a role several times. Yoshinori played soccer back in middle school but stopped because if he got to much muscle from it, it would be harder for him to pass as a girl. His friend Wataru however continue as a good player. Meanwhile Hidari also is happy for playing soccer. First for fun but when Yori create a girl soccer team on their school she recruite Hidari at the same.
 * Big Sister Instinct - Miki to Yoshinori, especially after she accidentally discovers his crossdressing.
 * Bishounen - Even when not crossdressing, Yoshinori is still considered attractive, and the others will often comment on how sexy he is or how sexy he acts.
 * Bi the Way - Wataru, although it may have been a joke on his part, but it's really hard to tell considering his serious expression when he made the comment.
 * His relationship to Yuki also give his best friend Yoshinori problems with this. He already love both Hidari and Minamo but as Yuki he can't really say no to Wataru because of their friendship. The fact that their dates make him feel like a real girl doesn't make is easier either.
 * Brick Joke - During the school festival, Wataru makes a joke (or not, no one's sure) about wanting to after seeing how pretty he is when crossdressing (although it's not as Yuki). Later, when Wataru is in a funk after losing a football game, about a chapter after Yoshinori outed himself as Yuki to him, Yoshinori comes in full Yuki regalia to comfort him, and asks him if  He doesn't, but they kiss.
 * Miki finds out about Yoshinori's crossdressing in volume 1, but it isn't until volume 6 that she sees him dressed as a girl again (as he's returning from a date with Wataru), and she just greets him as if nothing was strange about it. This scene may have been done to remind readers that Miki knows about Yoshinori's crossdressing.
 * Camera Fiend - Yoshinori who mostly take selfportraits of him self as Yuki. Minami, Hidari and Kagami however also come in front of the lens.
 * Cool Big Sis - Miki is this to Hidari and Yoshinori want to be it as Yuki as well.
 * Cute Little Fangs - Lampshaded with Shiba in her first brief apperance in the second chapter.
 * Cute Sports Club Manager - Nobuko for the boys soccer team in the high school. Yoshinori and Wataru wonder why she is it for a boy team but guess she is the type who support other. Yori may also count as she start a girl soccer team in the middle school with Hidari, Yu and others.
 * Deconstruction - of Attractive Bent Gender and romance manga in general. It becomes evident fast that being stuck in a Love Dodecahedron is not doing anything good to Yoshinori's mental health, along with trying to still be able to pass when crossdressing.
 * Defrosting Ice Queen - Kurokawa.
 * Destined Bystander - The manga were originally planned to be only one volume. When it groved several of the characters from that first volume got their role expanded a lot. This goes for both Wataru, Miki and Shiba.
 * Ecchi
 * Growing Up Sucks - Hit Yoshinori first time when he realized, he has grown from 161 cm to 169 cm, which make it harder for him to pass as a girl.
 * Huge Guy Tiny Girl - Wataru is much taller than both Nobuko, Yuki, Minamo and just about everyone else.
 * It Has Only Just Begun - During the Yuki vs. Nogi basketball game in volume 3.
 * Love Dodecahedron - A pretty big part of the story: The main Love Triangle is with Yoshinori, who love both Minamo and Hidari. They both love him back. But then there are also Sakura and Kagami who both love Hidari, Shiba who love Yoshinori, Wataru who love Yuki, Nobuko who love Wataru, Miki who love Hidari's father and Nogi and Kodama who love each other. And then we haven't counted the relationships between several family members.
 * Meganekko - Kurokawa, again. Sometimes, particularly when she's studying in later chapters, Hidari also wears glasses.
 * My Name Is Not Durwood - Minamo decide to call Yoshinoris crossdressing alter-ego for Catherine, when she first meet "her". As a running gag she do it several times afterward just to tease her/him, while she annoyed correct her. It end however when Minamo request that they should be girlfriends.
 * Only Six Faces - Possibly the reason Yuki is so attractive, the girls and guys have similar faces.
 * Passionate Sports Girl - Hidari Morii like playing soccer and is skilled as well so when her clasmate Yori Hotta is founding a girl soccer team she is promptly asked to join which she does. Meanwhile Toko Nogi is the captain and The Ace of her high school basketball team. All three girls however have the same problem: other people have a hard time keeping up with their talents and ambitions, in sport as well as love.
 * Precision F Strike - Yoshinori gives one off when he realizes that he's infatuated with his own female alter ego, Yuki.
 * Reality Ensues - Anywhere else, the situation Yoshinori finds himself in, crossdressing and having people attracted to him, would be played for laughs. But here, Yoshinori feels how the situation gets to him, with his attraction to both Kurokawa and Hidari, and manifesting emotional turmoil due to his fear of hurting either of them, his coming to grips with the fact that he's becoming a man whether he wants to or not, the impulsivity that comes with being a teenager and how it affects those around him, etc.
 * Real Place Background - Many of the locations are real places in Tokyo, often surprising detailed drawn. A collection of pictures of the real places can be seen here.
 * Sailor Fuku - Minamo's old school uniform which she give to Yuki. It become symbolic on two later occassions. First when Yoshinori wear it to "continue" after he and Minamo got disturbed while about to getting close. Second when he
 * Schoolgirl Lesbians - Kagami towards Hidari.
 * Secret Keeper - Everyone who learn about Yoshinori being Yuki will keep it secret, unless they are sure those around them know it as well.
 * Secret Secret Keeper - Kodama after he find out that the girl, Yuki, Yoshinori got him as a model, is Yoshinori crossdressing. Kodama then helps to keep it secret without letting Yoshinori or other know that he know - until he see Yuki hand in hand with with his own love interest, Nogi...
 * Smart People Wear Glasses - Minamo and Kodama who are best and second best of their year both wear glasses. Later Hidari as well.
 * Stoic Spectacles - Kodama. Double as Meganekko in the crossdressing cafe.
 * Unsettling Gender Reveal - Happens to Wataru in chapter 68; however, he's forgiving of this, especially after encouragement from Kurokawa.
 * He's not the only one, though: it happened to Nogi during her game against Yuki, Miki accidentally found out while looking for her clothes, Kodama found out about Yoshinori's crossdressing due to his collarbones, and Hidari only found out after Yoshinori confessed it to her.
 * Kurokawa on the other hand revealed it herself, to the surprise of Yoshinori, who thought his crossdressing were perfect.
 * Wholesome Crossdresser - Yoshinori.