My absolute favorite shy!Jensen is The Treat Fairy (http://bbsock.livejournal.com/1642.html) by bbsock. Jared does woo Jensen here :)

Enjoy!

Second this rec for THE TREAT FAIRY. Anyone have a PDF file for that one?

Also, I would think everyone has read annella's COUNTING THE STEPS, but if not - go right now and read it!

http://archiveofourown.org/works/78808/chapters/104954

Yes, I have already read both of them. Thanks anyway :)

Edited 2015-02-14 12:15 am (UTC)

Have you read As this Sunset turns to Morning (http://users.livejournal.com/_mournthewicked/250450.html) by mournthewicked ? It's a classic, so you probably have, but I thought I'd rec it just in case, because it sounds like it fits what you're looking for.

Summary: Jensen spends his life hiding who he is from the family that would never accept him if they knew. When he’s uprooted in the middle of his senior year and suddenly becomes the new kid, his carefully placed mask begins to slip. Especially when he meets Jared – a loud, outspoken spectacle of a boy that fights for everything Jensen was taught to stand against. Jared has no problem going after what he wants, and now it’s just a matter of Jensen letting himself do the same.

YES! That's exactly the fic I was coming here to rec :D
It's so beautiful and completely fits the request, doesn't it?
It's also available as a podfic (http://audio-by-juice.livejournal.com/22554.html)

ha ha, no I actually haven't! Thanks!

Jensen Ackles Doesn't Exist aka JADE, fits that description. http://xen-fic.livejournal.com/3073.html

Thanks :)

Maybe this one? Twists and Turns by tcs1121?

http://tcs1121.livejournal.com/10057.html

Twists and Turns (http://tcs1121.livejournal.com/10057.html)

(sorry, not sure if I did the link right)

It works fine. Thanks :)

These two are from the SPN Kink meme so you have may have already seen them:

How Many Flowers, Would You Guess? (http://archiveofourown.org/works/3211925) Jensen is a baker. He loves his job, is shy, sometimes clumsy, wears glasses and loose sweaters. One day he backs his car out of a parking lot and crashes into the car of Jared Padalecki. Jensen immediately starts babbling, wants to apologize, all the time trying to push his glasses back up his nose, searches for his insurance card in his pockets.
Jensen is so distracted that he doesn't see the amused smile on the other man's face. Doesn't see how Jared Padalecki, son of one of the richest men in the city, can't take his eyes off Jensen and immediately falls in love with the man who has flour all over his cheek.
Over the next weeks Jared comes to Jensen's bakery and tries to woo him.

Accidents don't happen accidentally (http://spnkink-meme.livejournal.com/88360.html?thread=34536488#t34536488) BTS Mockumentary non-AU, Bluesteel!Jared/Delicate Flower!Jensen

I've read the first one, but not the second. Thanks :)

Uhhh I just love shy Jensen. You probably read them already, but these are some of my faves:

Never Looked the Same (http://osmalic.livejournal.com/140825.html) by osmalic
Looking for a Lesson in the Periodicals (http://lukasalita.livejournal.com/6905.html) by matalinolukaret
Lost and Found (http://mediaville.livejournal.com/57649.html) by mediaville(this is a must read!!)
It's not a lack of personality (http://kelleigh.livejournal.com/290090.html) by kelleigh (ugh i love this soooo much)
Grapes of Wrath and other Forbidden Fruit (http://astri13.livejournal.com/101306.html) by astri13

Hi, these are not so typical shy Jensen stories, but perhaps you give them a try.

Win and Protect http://the-green-bird.livejournal.com/7847.html (http://the-green-bird.livejournal.com/7847.html)

A Life Less Ordinary http://fedaykin-here.livejournal.com/tag/a life less ordinary (http://fedaykin-here.livejournal.com/tag/a life less ordinary)