Risk it.

“Wait.” You hasten to jump into your boxers and intercept her. “Um…before you go Trish. I wanted to ask you something. Before you walked in on, well, that...” He motioned to the bed. “It probably would’ve been better before. But I do mean it, and it can’t wait. I should’ve said something ages ago, but the timing was never right. Even though you’ll probably just punch me, I have to do this now.” She fixes you with a quizzical expression, maybe a little bemused at your babbling. Just minutes ago you were the pinnacle of masculinity. Now you’re putty in her gaze. You take a deep breath, squaring your shoulders. “Trish, will you go on a date with me?”

The silence was deafening.

“You’re right.” She deadpanned. “That is terrible timing.” You wince noticeably, but she holds up a dramatic finger. “Still though, you put on a pretty impressive display today. A girl would be mad not to give it thought.” You perk up a little and Trish is quick to dampen your mood again. “Then again you went ahead and put your dick in a stranger’s mouth on your first day at what’s essentially an all-girls school. That's always a red flag.” She continues her dramatic self-debate for some time. When Trish had something you wanted she could spend hours toying with you before she gave you an answer. Like that time, you forgot your bug spray on a camping trip. It's nice to know some things don't change, you think to yourself. The girl before you had grown up in all the right ways, but she was still the same old Trish.This time you’ve learned your lesson and hope you manage a patiently interested look.

But she was still going, and enough was enough. Grabbing her face in your hands you pull her towards you press your lips to hers. Her shock is quickly overcome as she reciprocates the kiss, pressing her body to yours and wrapping her hands around your neck. You savour the kiss for a moment longer before extracting yourself to look her in the eyes expectantly.

She bites her lip in serious thought. It’s enough to bring a familiar stirring in your pants, hopefully she decides soon. “Alright, John. One date. Tomorrow night.” You can’t help but grin. “But nothing fancy. My dorm. Not here. I’ll pick the movie so you bring the food.”

“Yeah, absolutely. That sounds great." At this point you would've taken anything so you're eager to agree. She gives you a coquettish smile as she pats your bare chest. “Don’t forget to wear some clothes, too.”

“Are we really going to need them though?” You call after her, emboldened by your winning streak. She just laughs and waves over her shoulder as you watch her magnificent backside retreat down the corridor.