Sylvester's Family Tales 11

Story by Ragemend on SoFurry

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#10 of Sylvester's Family Tales

Sylvester and Tom say goodbye to high school in the best way.


Sylvester couldn't sleep, he had too much to think about. He was going off to college tomorrow! His next big leap in his life. So much to do and he didn't feel prepared. And on top of that Tom told him about the recording of them having sex the night after his 18th birthday party. In masks no less! Tom never said what he was going to do with it, but there was video of them having sex! He was so embarrassed. He was so busy thinking about all of this that he didn't notice the pair of glowing eyes looking at him from the top bunk.

"Can't sleep?" Asked Tom, shielded by darkness.

"No, too much to think about tonight." Responded Sylvester nonchalantly to his older brother.

"That's understandable, considering what's tomorrow. I take it our usual night time habit won't do tonight?" Quipped Tom.

Sylvester was morose, not biting at the line his brother was casting. He rolled over to face away from Tom. However, Tom knew exactly why his brother was giving him a cold shoulder. He doubled down.

"What if we go say goodbye to your old high school in the most perverted way possible, I bet you'll sleep fine then." Bargained the cat, his grin hidden by the darkness.

Sylvester sat up in bed. "How will we get in? They lock the school at night."

Tom slid down to the floor and kneeled so he could be eye to eye with his brother. "My roommate in college is a raccoon, he taught me all the tricks for lock picking. Just think about it, the two of us fucking on your last homeroom teacher's desk your last night before you leave town!"

Sylvester was quiet for a minute, then got out of bed. "Okay, but we have to be quiet sneaking out."

The boys were lucky, after getting dressed and sneaking out the front door they found their bikes were still in the front yard and not in the garage. They wouldn't have to make any noise. The cats rode quietly, stashing their bikes behind a hedge. Tom had the door open in seconds flat and the cats snuck in.

Passing empty classroom after empty classroom they soon arrived at Sylvester's final homeroom. Tom picked the lock and the cats snuck inside. Sylvester grabbed a small packet of lube from his pocket and handed it to Tom, then dropped his pants and climbed on the desk. The younger brother presented his rear for Tom and lifted his tail. Seeing the view, Tom was instantly hard and took off his shorts. Joining his brother on the desk, he lubed up and slowly slid his cock into Sylvester.

The younger cat let out a: "Mmrowllll." As his brother slid into him, putting a paw over the tip of his cock so he doesn't drip pre on the desk. As Tom started to thrust into him harder, the cat forgot about dripping on the desk and used his pre covered paw to hold himself steady. Tom gripped Sylvester's hips and started growling, a sure sign he was getting close. Sylvester felt himself at the edge, the pure naughtiness of what they were doing providing kindling for his fire. With one more thrust Tom spurted strings of cum into Sylvester and Sylvester shot a thick load all over the desk. The two cats panted, with the older brother's erection fading in the younger. When he pulled out Tom's cum poured out of Sylvester's tailhole onto the desk. The two saw their mess and quickly exited the building.

They rode home in silence, Sylvester dripping cat spoo into his undies as he pedaled. When they got home Sylvester and Tom left their bikes exactly where they were, and as soon as the were back in their room they both giggled.

"See? Being naughty can be fun!" Said Tom, smiling at his brother.

Sylvester nodded at his brother. "Yeah, but next time I choose the position we film!"

The boys got in bed and quickly fell asleep. Tomorrow was a big day, but tonight was a big night.