My Best Friend's Brother

The Night

Jackson had been a good boyfriend all week.
Babying him at School and making him feel amazing at night. It was driving Stiles nuts.
Jackson moaned as Stiles dick hit the back of his throat.
"Jackson..." Stiles trembled as he came. Gripping Jackson's hair. Something he loved.
When it died down, Stiles realeased Jackson and fell asleep. Feeling Jackson cleaning him.
"Jax?" Stiles called softly.
"Yes, kiddo?"
Jackson answered.
"I'm sorry." Stiles said.
"For what?" Jackson asked.
"Not taking care of you? You do all these amazing things to me and I repay you by leaving you to take care of yourself." Stiles said sadly.
"I do all those amazing things because I love you. Not because I want anything back. Whenever you're ready." Jackson said.
"I just want you to feel good." Stiles said cutely. Jackson laughed and told him he worries too much.

It bugged Stiles so much that he talked to a reluctant Scott about it.
"It's like...Cumming makes me feel good but it makes me feel guilty.
I'm selfish." Stiles said sadly.
"I'm not comfortable with this conversation." Scott said.
"I'm sorry. It's just...I need to tell someone." Stiles said.
"How about telling the person you're dating?" Scott asked.
When he was right, he was right.

Jackson had wrapped up their Biology homework early because he could tell something was wrong with Stiles.
"What's wrong?" Jackson asked.
"Nothing..." Stiles said sadly.
"Stiles." Jackson warned.
"I feel guilty." Stiles said.
"Why do you feel guilty?" Jackson asked, wiping Stiles' eyes.
"Because I'm selfish. You're good to me and I leave you to suffer because I'm scared." Stiles cried.
"Shh. Don't cry, baby. I would never force you to do something you're not ready for. I can wait." Jackson said.
"You shouldn't have to. I'm not being fair to you and I deserved to be punished." Stiles said. "Please?"
"I'm not going to hurt you." Jackson said. He sighed and conceded. "Fine."
"I'll be quiet." Stiles said.
"Face the wall." Jackson said. Stiles obeyed. Jackson undid Stiles' pants.
"Do it." Stiles breathed. Then it came. Leather sharp against his soft bottom.
"You didn't__" Lash. "Do anything wrong." Jackson said whacking him.
"I'm mean to you." Stiles said.
"You're a good boy. You're my good boy." Just gritted and hit hard.
"Ahh!" Stiles cried out. "Sorry. Sorry."
"Go lie down." Jackson said gently.
"Thank you." Stiles said with his head down. Stiles lay on his bed. As in the air and his perfect boyfriend rubbing his raw bottom.
"Better?" Jackson asked.
"A little. You can take me if you want..." Stiles softly.
"No. Not unless you're ready."
Jackson said. Stiles turned.
"I am. It's okay." Stiles said.
"You sure?" Jackson asked. Stiles nodded. Jackson smiled and took off his pants. "We'll take it slow."
"Okay." Stiles breathed. Jackson got between his legs. Popping the tip in.
"This is gonna hurt but just look at me, okay? Just focus on me." Jackson said gently. Three inches deep. And another three. And so on until all nine inches were in. "That's a good boy."
"Mm-hmm. It's all in?" Stiles winced.
"Everything. You did good."
Jackson said warmly.
"Awesome. Can you do me a favor? Don't move. Or breathe." Stiles sighed. He grimaced.
Trying to keep it together.
"I'm sorry. I know it hurts. Want me to pull out?" Jackson asked.
"No. Just...gimme a minute." Stiles said pained. Focusing on Jackson.
"Now?" Jackson laughed.
"Yeah. Go. Go go go." Stiles said.
"Ah...So warm. Do you feel it baby? Huh?" Jackson asked holding back.
"Yeah...your huge cock penetrating me. Don't break me." Stiles plead.
"You can take it." Jackson said as he thrusted harder. Deeper.
"Jackson! Aaaahhhh...." Stiles cried as his boyfriend hit his prostate hard.
"Oh, baby. Yes! I'm not gonna last long if you moan like that." Jackson moaned. Jackson went balls deep in Stiles. Triggering an impulse to scratch before cumming hard. Jackson didn't last long when Stiles cried out his name. Nutting inside the boy. Hard. Spilling out like a bad hentai. Stiles licked himself off of Jackson. Getting him hard again.
"Again?" Stiles asked. Jackson smiled.
"Stay down." Jackson pinned Stiles and they went again. The only thing that stopped them was the return of the Sheriff.