Short A/N: First of all... This is when they're OLDER. And Second of all I'm going to write what they would do instead of kind of long stories. (I'll make a part 2 and write long stories like I always do only if I get requests on it. Just afraid I'll get hate).
Bill:
-You ask Bill about doing it
-He was shocked but agreed to do it
-Missionary position
-"A-A-Are you s-s-s-sure about this?" He asks you nervously.
-He slides in as slowly and gentle as he can
-Freaks out when he sees your eyes filled with tears
-Doesn't move until you say you are comfortable with it.
-Thrusts into you very slowly at first
-Kisses your neck gently to distract you from the pain.
-Soft moans
-Tiny whimpers
-Lots of heavy breathing
-Goes a little faster with a few minutes of slow thrusts
-He says your name a lot
-"Oh g-g-god Y/N."
-He says I love you multiple times
-Whimpers loudly when he climaxes
-Still inside of you when you two lay down
-A few minutes later he pulls out
-He cuddles with you until you both fall asleep
Richie:
-You were hanging out with Richie alone in your house and just talking
-You don't know how you both got into this conversation but you guys started talking about sexual things. (I mean that's trash the trashmouth)
-He jokes around talking about sex
-"I would just bang you right now"
-^He was kind of joking but he was a little serious in the inside (guys are just horny when they're alone it's not surprising)
-You guys started making out (this is where everything goes down)
-He has been waiting to have sex with you for a very long time (Still not surprising)
-Starts taking off clothes quickly
-Doggy style position first
-He pushes in not very slowly
-Stays still for almost a minute and starts moving at a normal pace
-A few minutes later he's going really fast
-He wants you to ride him and you obey
-You are facing him and going to town on him
-His moans are hot
-Swears a lot
-Hands on your hips
-Your legs start to get tired so you guys do missionary position
-He's taking you like he's a professional at this
-He groans when he orgasms
-You two are panting after your climaxes and he's still on top of you
-You both lay down on the bed for 30 minutes
-You two use the shower together and.... you can use your imagination on what happens in there ;)