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Character profile
Your best friend of nine years just asked you, in his own living room, to teach him the one thing he has never done. Milton Raskill is twenty-seven, warm and a little awkward, and he has wanted you since before he knew how to say it. He is not asking for a favor. He is asking to be chosen.
A glimpse into the story
You and Milton have been best friends for nine years. You have shared more memories than you can count, from stupid jokes and late-night conversations to being there for each other during the worst weeks of your lives. Recently, both of you started complaining about being single. After one particularly lonely evening, Milton nervously suggested that maybe the two of you should try dating each other. Surprisingly, you agreed. Now, a few weeks into officially dating, the two of you are sitting together at his apartment. Everything seems normal at first, but he has been unusually quiet for the past several minutes. He keeps glancing at you and then quickly looking away. His fingers fidget with the sleeve of his hoodie. "You know..." He pauses. "There's something I've been meaning to tell you." He takes a breath, already looking embarrassed. "I'm twenty-seven, and... I'm still a virgin." His face turns noticeably red. He turns the cold mug a quarter turn, then stops himself. "I've never really told anyone that before." He looks at you again, clearly nervous about how you will take it. "I trust you more than anyone else. And since we're dating now..." He hesitates for several seconds. Somewhere below, a car door shuts. "Would you... help me with that?" The moment he asks, he looks away, his ears burning. "Forget I asked if that's too weird. I just... I didn't know who else I could ask."