A/N: I picked out Rupret as Stiles first name becuase I honestly think its adorable and a bit cringe worthy.

As always if I've made any mistakes kindly point them out to me! Thanks!

Chapter One

The fence was just daring Stiles, looking him in the eye and smirking, with its new white paint probably still drying, and Stiles was up for the challenge. He turned ole Blue around, giving her a little pep talk and went for it.

Which was stupid. Because Blue was getting up there age wise.

Thank the lords. Blue's front hooves smacked dirt with an audible clap, with the rear following after safely onto crisp spring grass.

Stiles let a shaky laugh leave him, fist pumping the air a couple of times. Take that fence.

He was making weird bring it gestures to the fence when he spotted old man Hale walking his way. His cheeks reddened, not only was that embarrassing to have him witness it made Stiles stomach drop, old man Hale was going to kill him. The adrenaline of victory turned sour. They had an understanding but maybe now that they had a fence up Stiles wasn't allowed to cut through on Sir Hale's property. Not that old man Hale wasn't a good nice and untimely a smiley fellow , he was just scary, to about everyone else.

He had this thing about his property, the Hale's property was extremely off limits to anyone. Sometimes Stiles let the gossip get to him, today in town a group of snickering boys told Stiles that the new fence wasn't put up to keep things out but to keep people in. Which was quite honestly ridiculous seeing as the fence was maybe four feet tall.

Stiles was only allowed through on certain days, Sir Hale had been very stern about when he could pass. He mentally tallied up the days to make sure he wasn't on a nono day, but of course he wasn't because Stiles was scared shitless to defy Sir Hale or really he was scared of Madam Hale but he wasn't going to admit that aloud to anyone. She was very scary though. Stiles looked over the fence to make sure everything was intact.

Blue must've smelled the carrots or something because without warning she was galloping to meet old man Hale not letting Stiles man up and grow a pair, which he was thankful for because he'd probably would have let Sir Hale walk all the way through the field to him, which would have been extremely rude.

It was just that none of the Hale's were ever out when Stiles cut through, it wasn't like he trotted right by their house windows or anything, so they never saw him and he never saw them, not even old man Hale, and Stiles even liked him.

Blue plopped her head onto old man Hale's shoulder, and Stiles inwardly and outwardly winced, Blue was a…special horse, but Sir Hale just smiled and patted her lightly until she nuzzled the carrots out of his hand. Sir Hale waited until Stiles was on the ground to say anything, Stiles rubbed the back of his neck nervously.

"I was hoping I could catch you on your way home."

"Ah yes," Stiles mumbled because really, what is he supposed to say? 'Here am I!'?

"I saw you jumping the fence." Sir Hale gave him a stern look, and Stiles had to repress his flight urges, because if it came down to it Sir Hale no matter being a little over 50 could easily snap Stiles like a wish bone.

"There is a second gate a little down further, we wouldn't want to hurt Blue nor you Rupert. Try to think beforehand." Stiles did not wince when Sir Hale caught eye contact and matched his stern voice with a stern eye repercussion. " Blue is getting quite old, even if he is still strong enough through the days don't push him alright son?"

"Yes Sir." Stiles wasn't just saying it, old man Hale had made him feel guilty, not only was he looking out for Stiles he was looking out for Blue, and he was right, Stiles loved Blue and wanted to keep her alive as long as he could. As he thought it over old man Hale had just gave him permission to keep cutting through right.

"Am I allowed to keep passing through, Sir?" Stiles willed the world to please allow it. Cutting through the Hales property after work made him home fifteen minutes earlier than using the road, enough time to start dinner for his dad among other things, in the end the fifteen minutes were worth a lot.

Sir Hale turned away from for a good minute as if anticipating the next figure to come walking over the hill, walking quite fast actually. Stiles didn't recognize the man but he didn't look particularly happy.

Not too far away now Sir Hale cut the man off when he obviously opened his mouth to say something. Which honestly was the guys fault because he was on Old man Hale's property. Stiles sent the man a silent prayer.

"Rupert, I'd like to introduce you to my son, Derek Hale." Sir Hale motioned towards the man who was now right in view and apparently trying to glare Stiles off the property. "Derek, This is Rupert Stillinski, the Sheriff's son." Stiles wanted to beat himself against Blue. Old man Hale was probably the only person left in Beacon Hills to call him Rupert besides his father when he was strict. Not only was it embarrassing but being introduced as the Sheriff's son never really earned you any points.

"Please, call me Stiles." He tried to make it sound causal as he held out his hand, but it came out a bit more pleading than he'd like. Old man Hale just smiled amused, Derek on the other hand just stared at Stiles hand like it had offended him, but he enfolded his hand into Stiles for a very brief handshake after Sir Hale gave Derek a look, that Stiles obviously saw but pretended otherwise.

He thought that was all but both Hale's where standing there looking at him. He looked at old man Hale to see if he had anything further to say but he did not, but it also felt like he wanted Stiles to say something. He turned towards Derek who still was trying to force Stiles in the ground with his piecing blue-green eyes.

"So..I haven't ever seen you around?"

Derek blinked a bit surprised like he wasn't expecting Stiles to talk, but what else was he was supposed to do! Derek had just been standing there menacing at him and old man Hale just looked gleeful , hand still on Blue. It would have been quite rude of Stiles to just hopped upon Blue and rode off, not that he didn't think about doing so. Talking just seemed like the only solution.

"Derek was in New York for some studies, he'd just arrived home this week. He was quite sick as a child so none of you boys would have seen him when ya'll were younger."

Stiles repressed the urge to roll his eyes. All the Hales were sick as kids or some other excuse to never leave their property.

It was pretty amazing that Derek had gone to New York for school, the Hale's where really stacked but they never really flaunted it like the Whitmore's. Derek kind of did though, he was wearing a very nicely tailored leather jacket with a ridiculous number of silver buttons. Stiles tried not to feel insecure but suddenly his riding pants felt tighter than the normally do. Which honestly they're always tight seeing as he hasn't bought new ones since he was 15 so he could use his hard earned nickels for some other essentials.

Stiles didn't say anything more and Derek hadn't said anything to begin with but Sir Hale didn't seem to mind at all, actually Stiles was a bit taken aback when he smiled brightly at him.

"As to your earlier question of course you can still cut through, we are ever indebted to your mother Rupert, and if a little shortcut through thru pasture is what makes you happy then I'm happy."

Old man Hale was really taking Stiles aback, sure Stiles had assumed that the only reason the Hale's tolerated him was because of his mother, but they never said it out loud, and for heaven's sake they never said happy and his name in the same sentence or anything, and they never beamed at him.

Stiles might have taken a step backwards when Sir Hale's hand moved from Blue to his Stiles' arm. Sir Hale was still beaming at him though! Stiles body was having fits over deciding to giggle or run at this new found expression of his.

Placing his other hand on Derek who even more shockingly had red patches crawling over his jaw, which could not be blush it just couldn't, Sir Hale said, "And as I said before we have a gate a little farther down that you can use, because we don't want any more fence jumping alright, so I'm sure Derek will be willing to show you how to get there."

They gawked at him. Both of the Hales were having an eyebrow/eyes only conversation, and Stiles really didn't want to force anyone into anything if they didn't want to. It especially embarrassing and offending to see Derek's pleading face, begging his father otherwise.

"No that's alright, Sir Hale, ya'll have been already so welcoming, I'm sure it can't be that hard to find, thank you." Stiles clenched his jaw and the reins and tugged Blue towards where Sir Hale had pointed earlier. He was going to leave with his pride intact but then Derek spoke up.

"No, I should take you, it's fine." He said in defeat his voice gravelly. Stiles looked over his shoulder to see Derek walking towards him looking off to the side, blush still rosing his cheeks.

Stiles desperately tried not to think of that, he quickly imagined what it would be like for Blue to just kneel over and die. Riding pants, especially too tight riding pants was not how you wanted to tell the community you were gay.

As if Derek knew Stiles was thinking strange things he looked over him with a slightly concerned look.