As always, please send a PM if you're interested. Thank you for not replying here and helping me to keep my area clean!
An Unfortunate Wager
Tagline: A guy loses a bet and has to wear a women's costume to a party or convention and gets more attention than he bargained for.
Our characters are friends, and with an upcoming comic/anime convention or costume party, the two make a wager regarding something unrelated. However, the loser of the bet has to wear whatever costume to the convention/party (and act the part) that the winner decides. Losing the wager, MC is mortified when YC gleefully presents the women's costume for him to wear.
After dressing, MC is completely passable (and could have been a bit trappy to begin with), and at the convention/party, gets more attention from the horny guys than he bargained for. YC doesn't help any, convincing him, "Now smile at these guys walking by" and such, as he remains constantly surrounded by hard-ons.
I'm definitely agreeable to a relationship developing between our characters.
Send a PM if you're interested in further discussion!