It was a calm June night and a crisp draft emanated from the window, ensuring the boys would stay cool between the sheets of Jack's bed. "Ever been rimmed?" Jack asked. Milton shook his head. Jack used his thumbs to separate Milton's butt cheeks and then traced his friend's hole with his index finger. Milton grimaced at the new sensation. His reflexes were helpless as Jack's hot pink tongue coated his even pinker boy-hole in warm saliva and he unleashed a moan. He felt his cock spring up and he instinctively grasped it.
One Week Earlier
"I see London, I see France, Milton's not wearing any underpants," Jack said to Milton with a puerile smirk after the latter had karate-chopped a board and his short shorts had slid down slightly in the process.
"Like what you see?" Milton joked. Before Jack had a chance to respond, Rudy entered the dojo and summoned the Wasabi Warriors to the center of the room. Standing next to him was Joan, the mall security guard.
"Joan is here with some good news," Rudy said.
"Yes, I'm pleased to announce we've solved the April break-in!" she exclaimed, clearly proud of herself. "I'm here to return the items that went missing."
She pulled a pink hairbrush covered in a puppy paw-print pattern out of the brown bag she was carrying and asked if it belonged to anyone. Kim claimed it. The next item was a mini-sombrero, which everyone at first assumed belonged to Jerry but was actually Rudy's.
"And finally, this formerly white jockstrap, size medium." Joan said and held up the yellowed cup.
"Ew!" Jerry shouted. Jack shamefully made his way to Joan and took the strap from her grip. Milton found the sight strangely erotic and was left with a boner. With the excitement for the day finished, Rudy dismissed the group. Jack invited Eddy to Milton's house with him, and the other boy accepted. First he had to call his mom, though. After a lengthy discussion, she agreed.
Milton's dad was the cook in their family and he loved Jack like his own child, so he made one of Jack's favorites for dinner: mac and cheese with bacon bits. Jack, Milton, and Eddie were hungry from practice and ate quickly. The three then retired to Milton's room, which was plastered with posters of popular athletes and actors.
They played Call of Duty until the sun went down. Milton was the best at it because he had so many hours of experience. Jack was better at the card games they played, which quickly devolved into a high-stakes game of poker. Losers had to submit to the dares of winners. After a particularly bad hand for Jack, Milton dared him to wear the jockstrap on his head. Jack obliged, giggling as he removed it from his gym bag and pulled it over his face.
Since the invitation had been so last minute, neither Jack nor Eddie had packed any pajamas. Milton offered his own. Jack slept shirtless but wore some of Milton's pajama bottoms.
Long after the lights were out and the others had gone to sleep, Milton stayed awake gazing at Jack's stomach as it rose and fell with each breath. It was impossibly smooth and tight. Even in the dark, Jack's nipples beckoned Milton like maraschino cherries sitting atop a sundae. Jack's outstretched arms revealed a few long and curly underarm hairs. Milton longed to sniff his friend's pits, which he knew would smell like a mixture of teen sweat and body spray. He was tossing and turning, unable to sleep with a massive hard-on. When he did finally drift off, his dreams were all of Jack. In one, they were riding horses in speedos, and Milton leered at Jack's behind as he bounced up and down. In another, Milton had been 'deputized' and was a police officer that had to search Jack's every orifice for contraband.
Early dawn sunlight pressed against Milton's eyelids and he awoke. Following his body's directions, he rushed to the bathroom first to pee but then to jerk-off. He rubbed himself to the thought of the strip-search dream until creamy seed erupted from his penis, covering his hands and the floor. He got on all fours to clean up the mess, imagining his friend coming up from behind and fucking him. Then he returned to his warm bed and went back to sleep.
"Happy Saturday!" Eddie shouted and threw a pillow at a sleeping Milton. When Milton opened his eyes, Jack and Eddie were wearing their clothes from the previous day and standing at the edge of his bed – evidently awake for some time already.
"He's awake!" Jack cried in the direction of the hallway. The smell of breakfast filled the air and sure enough, Milton's dad entered the room with cinnamon-raisin French toast and scrambled eggs for each of the boys.
"I could get used to this," Jack said looking up at the adult in the room.
"You're welcome any time," Milton's dad replied, and his son silently agreed.
