What about Derek (+familiy) was raised very isolated and strict? He has no clue about the world or sex. So when he finally makes his way in the world, who would be better than the Sheriff or Melissa or both to show him that a kiss gets nobody pregnant….

uuuunf yes. 

This hairy, scruffy virgin right in the Sheriff’s and/or Melissa’s bed. Blushing and squirming and so confused over his big cock and how it’s lifting his loose shorts into a big, embarrassing tent.

oh man I kind of want Claudia to be there as well. Sheriff and her taking Derek in when he’s stranded because he has no idea about anything and her crawling into his little bed that very night because she needs those adorable bunny teeth on her nipples.

Derek would be so miserable the next day, sneaking around the Sheriff like a beaten dog; only next night it’s the Sheriff visiting him. Taking Derek’s large hand and helping him to curl it around the Sheriff’s big daddy cock. Derek doesn’t have to do anything but keep his fingers closed for the Sheriff to fuck into and look up at him with those confused, green eyes when the Sheriff makes sure to come all over his carefully trimmed beard.

but of course they invite Melissa over for the fun of it. They’re never mean to Derek, though.  just very hellbent on introducing him to all the fun.