Hardly anyone is providing any awkward!teen!sex fics. Or first time fics. Or general imperfect sex. Or humph.
So here is a completely random dump from my del.icio.us.
Supernatural
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this heart: it is not yours by
flipmontigirl - Dean/OFC - This is just beautiful and kind of breaky, because Anna wrote it. Dean's first time with a milf next door. Outsider POV.
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isis on the fifth day by
ggreenapple - Sam/sister. Frottage. Incest. A dykey girl!Dean. Beautiful language.
RPF/S
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Good Boys Don't by
winterlive - Jared Padalecki/OFC (high school, framing narrative in the present) - I've recced this a million times, for a reason. It totally captures the breathless, confusing, crazy, sexy that is first time lust. Read it regardless of what fandom you're in.
Um...unfortunately I've read too much Jared/Jensen RPS to be able to wrap my brain around which individual stories might fit. Besides they seem to be largely having "good" sex in porn about them. I'm probably having a brain fart. Bring on the links if you have them.
Friday Night Lights
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"Restraint" and "Verboten" by
svillficrecs - Matt/Julie - Hottest fic I've read where they don't get past third base. Includes (guilty!) wanking on the phone.
Smallville
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Inhale by Te - Clark/Chloe - Okay, so it's not THAT awkward, but it's totally teenaged.
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Seule et Amoureuse or "Five Times Lana Lang Got Thoroughly Laid" by
mskatej - The first two sections definitely count (Lana/Jason and Lana/Chloe respectively) and the rest of it is just awesome. Oh! And there's girl!frottage so yes, excellent.
Harry Potter
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To Remember Me - by
silvernatasha - Ron/Lavender - Set during Deathly Hallows. Warning: This is a really good fic, and it feels v. canon, but part of what makes it so "authentic" is that teenage girls sometimes do things like have sex for the first time with boys they know are in love with someone else. And they sometimes don't ask for what they need.
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Too Far by Resonant - Ron/Hermione - This fic is so short and SO AWESOME. It's like an antidote for all those other fics that are WRONG (ymmv).
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Ordinary Days by
penknife - Ron/Hermione first time - Not all that porny. Not all the long. V. good though.
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One Rainy Night by
inell - Ron/Hermione - Set during DH but written before. Excellent Ron POV. He's so randy! And yet sweet. Mutual masturbation. Awkward conversation.
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Things They Should Have Taught Us in School by
stoney321 - Ron/Hermione - Dryhumping in Grimmauld Place!
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This James/Lily Story by
kethlenda that is on
erotic_elves and so flocked until further notice and I can't find it elsewhere. Damn.
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De Facto by
jaswanson - Ron/Hermione - This one's from the flip side. It's awkward, imperfect old people sex (or well, 60-ish). It's great. Read it.
Um, I'm getting distracted and this recs post is on the verge of veering off into one of two directions: a) stories where a teenage boy is devirginized by an older girl/woman or b) boys tagteam wanking. Here's some of both:
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All the Boys to the Yard by
alizarin_nyc - Buffyverse - Faith/Connor.
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Come Inside Now, Okay, and I'll Shake You by me and onelittlesleep - SPN - Sam/OFC. Er, I'd say at least 1/3 of my own SPN porn falls under the weird/awkward/teenage/first time category but I assume if you're reading this journal you're probably already aware of that. I will say that [this] and [
this] involve dryhumping.
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Rain Boy by
onelittlesleep - Sam and Dean. The Impala. A smut rag.
OKAY. So this is the most random recs post ever! I got overwhelmed because SO MANY of the porny stories I like involve realistic!imperfect!sex that it became difficult to figure out what limitations to employ here.
Now. I still want Harry/Ron friendshippy wank!fic. And I realized that I just haven't read that much fic of this kind in Buffyverse fandom, largely because I mostly read fic involve Spike and/or Angel and they're like old and vampires and stuff so they clearly know what to do. Much love to the person who provides me with awkward!vampire!sex.
ETA: There are some links in the comments! FNL, Dawson's Creek and BSG as of now.