Unlikely Endeavors

It's been another week since Chris got the news that he's probably never going to be able to return home. It's been pretty hard on him, but he was slowly coming to terms with it. Ivory has been doing a good job at keeping him company and keeping his mind off it as much as possible.

He wonders what his friends and family think. Is there just a hole where is house used to be on earth? They probably think he's dead at this point with being missing for over a month. A small part of him wanted to take the risk of trying to go back, but he trusted Twilight enough to listen to her, even if the decision was ultimately up to him.

He sat in his room and finished off another one of the books Twilight gave him and put it in the pile of books he was finished with. He didn't care for reading much back on earth, but there wasn't TV or movies he could watch so he had to keep himself entertained somehow. You can only play so much Kart before it get's a little boring.

He did enjoy learning about Equestria though, about different mystical creatures and the history. Discord had to be one of his favorites to read about, everyone needed a little chaos in their lives sometimes. Maybe he would come visit Twilight one day and he'd get to actually meet him. Twi told him all sorts of stories and adventures they went on together with all of her friends.

Twi has been very good to him since he has been here, giving him a place to stay, food, and in general being kind. She has done more then some of his best friends would ever do for him on Earth, and she barely even knew him at the time. Since he was going to be staying here for a while, the least he could do was help out around the castle as payback. She refused at first, but he just didn't feel right mooching off her like this. He cleaned the bathrooms, swept the halls, simple things. Just something to occupy his time and give a little back as well.

Chris grabs another book from his desk and lays back down on his bed as there is a knock on the door.

"Come on in." He says a little louder then normal.

The door opens and his favorite pone comes in the door and shuts it behind her.

"Hey hey." She beams over at him as she takes her bag off and puts it on his desk chair.

"Hey yourself." He replies to her. "Got homework?"

She nods as she ruffles through her bag. Pulling out some papers and her book for the class.

Chris puts is own book down and get's up from the bed, making his way over to the desk. Ivory sets the needed materials on the desk as she sets her bag on the ground. Chris takes a seat in the chair as Ivory hops up into his lap. Chris scoots closer to the desk as he looks over the paper.

"Math again huh, I know why you hate this so much, it was my least favorite class too."

"I know, it's worthless knowledge. Like I'll ever need to find x when I go to the market to buy stuff."

Chris chuckles at that. "Yeah, you are right on that one."

He turns the math book open to the page directed by the work and starts to skim over it.

This was the average weekday with them. Ivory comes over, Chris helps her with any work she didn't get done already, then they do whatever they want after. Most of the time it's video games, but lately they have tried other things. Going to the park was nice, or just walking around the town at night. Ivory showed him Sugar Cube Corner the last time they went out, those were some damn good cupcakes.

After about 40 minutes and explaining to her how to do the problems and show her work, they are left with the finished pages of homework.

"Thanks again, I really appreciate the help." She turn slightly in his lap to look at him.

"No problem at all, the least I can do." He grabs her bag from the floor and puts it on the desk for her.

She leans forward as she starts to put all of her stuff back into her bag. Chris watches her as his eyes drift to her wings. They were slightly unfolded, probably to keep her balance. He spotted a few out of place feathers as gently reached forward and plucked one out.

Ivory gave a slight wince at the feeling as she stopped what she was doing to look back at him.

"Sorry... I've just seen you take broken feathers out before, didn't mean to hurt you."

"N-no... it's fine, just wasn't expecting it was all." Her eyes search around his face for a moment.

"You wanna preen me? It's been a few days since I last did it."

"If you don't have a problem with it, sure."

She nods and turns back to the desk and finishes putting her stuff away.

Chris gently takes a hold of the base of her wing and searches through the feathers with the other hand to find any out of place or broken feathers. He found his first as he got a good grip on it.

"Should I be gentle with it or just pluck it?"

"Just give it a light tug, it it doesn't come out don't force it."

He nods as he lightly pulls on the feather as it comes out. He continues to find others as his other hand gently rubs the base of the wing. He feels Ivory shutter slightly as he does.

"You okay?" He didn't want her to feel uncomfortable.

"y-yeah I'm fine... just you know.... Wings are very sensitive..."

Chris got the message by her tone of voice.

"Oh... like, that kind of sensitive? Like you're not gonna get off to this are you?" Chris said jokingly.

"Some Pegasi can..." She replies.

Chris let that one sink in a little as he got another feather.

"Was he feeling his best friend up right now? Was his best friend letting him feel her up right now?"

Regardless he found the rest of the feathers on the wing. Their was only a few as he turned over to the other wing. He didn't know if he should feel weird out this or not. He continued to preen her, only having a few out of place feathers on this wing as he rubs up and down the bone running along her wing.

That got a muffled groan from her.

He continued as he finished off preening her as he took both hands to start massaging her wings from the base of her back, running along the edge and all the way to the tip, then back down and repeating the process. He could feel her heartbeat in her wings as he felt them.

"C-Chris s-stop..." He immediately stopped.

"you're gonna f-fucking set me off it you k-keep doing that..." She said shyly.

"So you are one of those Pegasi that get's off to this, huh?" Chris leaned in behind her and whispered in her ear.

"S-Shut the fuck up...."

"If you ever wanna do this again, just let me know."

She turned back to him and stared into his eyes with an unreadable expression. Their was a bit of anger, he was teasing her. But there was also want, and unknowing.

"Can... C-Can you..." She kept staring at him as he listened.

"Can you finish me off...?"

That was the last thing he expected her to say.

A blush started to form on both of their faces.

"You can't just get me all hot and bothered and not finish the job. that would be pretty rude..."

"I guess you're right..." He replies as she turns back around.

He placed his hands back on her wings and continued his motions. Ivory stopped holding back as she was openly moaning softly as her body tingled.

Very soon after he started to feel a wet sensation coming from under her and was now going through his pants.

"Was she that pent up?" He wondered to himself as another feeling started to grow between his own legs.

He worked his fingers harder into her wings as she start to grind herself into his crotch, which did not help his situation downstairs at all.

Her panting got heavier and faster as she locked up all of a sudden and let out a single high pitched moan.

And she came hard.

Chris softly kept rubbing but not as hard as he was and let her ride her orgasm out. Her breathing slowly went back to normal as Chris's pants were soaked.

"H-holy shit..." They said in unison as they sat in the aftermath.

She stared up at him as she lay back into him as he smiled softly down at her.

"Same time next week?"