You try

You suspect Jackie can kick your butt if she wants, but she agreed to go out with you so you're going to try to kiss her. Well, actually, this being the 2020s, you figure you'll try by asking for consent.

"Uh, Jackie. Can I kiss you?"

She looks at you like you've grown a second head.

"God, is that what you've been so quiet about for the past five minutes?"

"Well, yeah."

"I'll say one thing, you're different form most guys I've dated."

"Is that a good thing or a bad thing."

She looks you in the eye. "Could go either way."

She didn't say no, so you take that as a yes and go for the kiss.

{if Jackie < 2}She meets your lips with hers... which is a good sign, but her lips stay hard and you end up with a quick liplock rather than the French kiss you were going for. Well, at least she didn't tear your head off.

{else}Her lips go hard for just long enough that you wonder if you've made a horrible mistake, but then they soften, and she leans in toward you. A second later and she opens her mouth, letting you explore her with your tongue.

She tastes of beer and salt from sweating at the softball game but that somehow adds up to a feminine and sexy sensation.

After a good minute, she pulls away. "Oh. You're a better kisser than I thought."

"You're no slouch, either."{endif}

{if Jackie < 3}"You know, we should try this again sometime. Call me."

{else}She grabs your hands and puts them on her breasts.

"Oh. God, they're wonderful."

"They're not as big as your Asian hottie, Barbara."

"She's not mine and it's not polite to harp on her ethnicity."

"Shut up and kiss them."

Since you're outside in front of her apartment, you don't think she's ready for you to yank up her top like you want to but you can feel she's somehow lost her sports bra. Only the thin, silky fabric of her softball uniform top separates your hands and lips from her soft breasts and nipples that harden underneath it.

You gently bite that hardening nipple through the cloth and she moans.

"I don't date nerdy-guys," she protests, but you're pretty sure she's not rejecting you, she's rejecting her previous standards.

After a couple of minutes, she moves closer and pulls your head up, kissing you on the lips again as she slides a leg between yours, bringing up her thigh so it presses on your dick.

"God, I almost wish my roommate weren't here," she finally breaths. "But... that's it. Gotta go. Call me again. Hate being a tease but... gotta go."

You give her one more kiss on the lips, then let her back away from you. You're both breathing hard and there's a visible pulse in her neck that seems to be pounding as hard as your own heart.

"See you, Jackie," you say.

"Oh, one more thing. If that Barbara chick is right, you need to learn to fight."

"Huh?"

"Assholes like that don't stop by blackballing your career. If you don't roll over for them, they'll be coming after you physically next. So, we'll add some kickboxing to your workouts."

You just nod.

{endif}

Jackie gives you a wink as she heads for the external door to her apartment building. "See you, Mike."

You nod. "You got it."

Then she's gone.

That... seriously could have gone worse.