Here's a great story that covers your request - "I've Got a Hand For You". Dean helps 14 year old Sam feel less awkward about puberty. This is a surprisingly loving and tender story, and incredibly HOT.

http://valiant.livejournal.com/110338.html

EDITED TO ADD: If you can rec any stories with this theme that you've already read, I'd love if you gave links. Thanks.

Edited 2015-04-17 01:56 pm (UTC)

Thanks a lot!
I actually came here after re-reading The Homework Verse (http://archiveofourown.org/series/19351) for the thousandth time.
I'm sure I have read some weecest fics with this theme before, but unfortunately, I haven't bookmarked them. The one you recced was one of them, I loved reading it again :)

Possibly Collared (http://www.sinful-desire.org/archive/viewstory.php?sid=4070&chapter=1) and its sequel, Ebb and Flow (http://www.sinful-desire.org/archive/viewstory.php?sid=4072&chapter=1)? (J2)

Thank you! Can't wait to read these :)

"Not Gonna," (http://archiveofourown.org/works/830531) fantamae: In which Dean has some fucked up ideas about what "teaching your brother" entails, Sam turns into a little cock tease, and Dean goes back on his word.

Edited 2015-04-18 08:22 am (UTC)

Thanks! Great fic.

It's one of my favorite favorites! :D

Here's another J2 series: Learning the Ropes (http://archiveofourown.org/series/172631): For a kink meme prompt requesting an established J2 relationship in which Jensen and Jared are just starting to try out some D/s with Jensen as Jared's Dom.

Thank you! I'm going to read it right now.