I'm rather interested in H-manga/Borderline-H where the guy is shy or at least not outspoken. Bonus if he had some quirk or is just good in bed (like the one in love-comedy style where the supporting guy character had an above-average sized tool). Genre not important, I enjoyed a shoujo manga of this kind once, though forgot the title. 😀

There's an H-manga that's great overall called Virginal Communication by Sasagawa Hayashi. Two chapters deal with a couple and the guy has trouble expressing himself (not easily apparent in the 1st part). The names of each chapter are "Sana Anekawa and Reading Between the Lines" and "Once More Hello!"

Kikkawa Kabao has a chapter titled Bougen Honey where the female character is so strong, any male character (the protagonist) would appear timid.

Saida Kazuaki created one small chapter in Paipain named "We Are Love Beginners." The guy struggles to take the next step with his girlfriend.

Dame Dame Suki made by Nico Pun Nise is about a boy being bullied and the swimming teacher giving him more confidence.

Not sure if these are close to what you are looking for, but they great stories in general.

The Calm After The Rain is Like Love from Cheerism.

Henkoi!

[img]http://i52.photobucket.com/albums/g32/akari_mizunashi/reallybutton.png[/img]

I've read dame dame suki and henkoi, am going to try out your suggestions. Yaritai Hitozuma is another good example of what I'm looking for, or chapter 3 of Fu Junai

Bousou Shojo by TORIKAWA Sora
is a hilarious comedy involving a tough looking but outspoken boy who repeatedly gets raped b/c of his girlfriend's misunderstandings

Take on Me by TAKEMURA Sessyu
has a main character that eventually becomes the sbmissive one in his relationship with girlfriend

Horn by Ahobaka
Involves an apologetic boy who is sold to a witch.

Ryoutou Ronpou by Vox
Is about a shy boy who tends to his girlfriend?

Boy Soprano by WANYAN Aguda
is about an adopted boy raised to live as a girl.

Love Love Akira-kun by GURA Nyuto
Is about a boy who gets and seems to enjoy getting bullied.

Carnivorous Fujoshi Hikikomori by Yurikawa
Is about a boy's relationship with his shut-in cousin.

In The Express Train by HANAMAKI Kaeru
Is about a boy who is gang raped in a train.

Naburi
Is a story from the perspective of masochist boys as they get sodomized -_-