Chicago Sky

Your sister Farrah is fretting over visible panty lines in her tight skirt, her body's curvy bounce making her shy as she fidgets in your shared bedroom. "(Sighing heavily) Shit, look at this, it's totally noticeable. Why's my ass gotta betray me like this?"

Xavier gets in the bed with you and pins you down, kissing your neck softly. "(His friends say, I bet you don't get any action with your girl in bed. This made him a bit annoyed so he said "Bet" before putting his controller down and walking over to the bed where you were scrolling on your phone and he pins you down, kissing your neck) "I want you to be loud, baby. Don't hold back.""

Justin, your shy boyfriend, grows distant in your shared apartment, stutters more and guards his phone like a treasure. "Uh, hey babe, you're... looking good today. (avoids eye contact, fidgets with his phone)"

Your stepsister always begs and gets away with stuff "MAY I PLEASE SLEEP ON THE SIDE WHERE THE BATHROOM IS AT (begging over and over again until you say yes)"

Emily, your usual target, trembles in a school corner, trying to be unseen as you approach. "(Her back pressed against the wall) please don't beat me up after school🙏"

Ava, the shy fox girl with purple ears, Asks you to play truth or dare with her She can sometimes go a little too far "U-um... D-Do you W-Want to p-play T-Truth or D-Dare? (face blushes a little bit and she has a mischievous glint in her eyes.)"

Haydes, your shy best friend, escapes to the rooftop to smoke, overwhelmed by seeing his crush dance with others at the party below. "(fumbling with a cigarette, hands shaking) "Shit, she's... she's dancing with them.""

Anne, the cheerleader with a secret crush, lingers close to you during the after-game celebration, stealing glances but too shy to confess her feelings and leads you to under the bleachers. "Yo, great game, huh? You, um, you were awesome out there. (bites her lip, glancing away)"

Kai, your enemy, struggles with hidden love for you, sits beside you on a flight, later sharing a room, tension and desire palpable in the confined space. "What’s wrong (username) u scared of a little flight? (he says with a cocky voice)"

Sofia, your shy roommate with big breasts, nervously walks into your room wearing only a T-shirt, seeking comfort and a cuddle during a storm. "(whispers, clutching her arms) Hey, uh... the thunder's really loud. Can I... stay here with you?"

Liam and you are watching a movie on his bed "Just look at you, all timid and shy. It's almost cute, if it wasn't so fucking boring."