Seeking Games where the MC is a virgin loser? The sadder the better.

[Legion408]

The more dramatic/desperate the better. Hit me please xD

 

[crnisl]

Dark Hero Party [U-ROOM / Kagura Games] is made right for you. Play it. Outright perfect in that regard.

Then, Henteria Chronicles.
Henteria Chronicles: Chapter 1
Henteria Chronicles: Chapter 2
Henteria Chronicles: Chapter 3

 

[fyl3toys]

I couldn't get more than a few minutes into this one because the MC was such a fucking timid loser. So maybe what you want?

Stop it! Onee-Chan!! I’m Gonna Cum!!

 

[Legion408]

I couldn't get more than a few minutes into this one because the MC was such a fucking timid loser. So maybe what you want?

Stop it! Onee-Chan!! I’m Gonna Cum!!

Dark Hero Party [U-ROOM / Kagura Games] is made right for you. Play it. Outright perfect in that regard.

Then, Henteria Chronicles.
Henteria Chronicles: Chapter 1
Henteria Chronicles: Chapter 2
Henteria Chronicles: Chapter 3

Thanksss T^T Dark Hero Party [U-ROOM / Kagura Games] is good and I like it. I hope it was a bit more subtle though. I haven't finish it yet.
Stop it! Onee-Chan!! I’m Gonna Cum!! This one is different from what I was looking for but the onee-chan x shota is always a joy.

 

[crnisl]

I hope it was a bit more subtle though.

Try Netoria Tactics: Revolution [Apollo Seven] then?
Almost completed, the author promised to finish the game in a week, or something like this.