The Watcher Part 2 - Sex Stories

The Watcher Part 2

... skirt.

He pulled the soft sweater over his head and the ensemble was complete. His rock-hard teenage cock strained against the fabric of her silky lingerie and pushed against the front of his short skirt, giving it a pup tent appearance. Vince ran his hand over this bulge and enjoyed the sensation.

It was later that day that loud conversation and music interrupted his nap. He looked out his window and discovered his sister and two members of her squad were working out. Once again, the sight of his sister in her spandex shorts and crop top had him hard in record time, so he headed to his closet and his hidden treasure.

He grabbed his sister's old cheerleader uniform from its hanger and proceeded to dress. By the time he pulled her sweater over his head, his cock that was nestled in the silky panties was rock hard.

Vince took a long look at himself in the mirror before moving to the window. Once again behind drawn drapes and lowered blinds, he watched his sister who was glowing with sweat jump and kick. His hands slowly ran the ...

... length of his legs from knee to hemline before they disappeared under the short skirt.

He managed to pull his panties down just far enough so that his cock could spring free. One hand pulled and held his skirt up while he stroked himself with the other. He fantasized about being in the back of the team bus with her wearing his uniform and sharing gentle kisses and caresses with her.

The inclusion of his cross-dressing in his fantasy was new and it felt good. He imagined Elaine sitting in his lap after pulling her skirt up and making Vince do the same, Now her warm and wet silk-covered mound was rubbing against his hard cock still hidden in his panties.

He imagined Elaine's soft lips seeking his and the sensation of their tongues touching amid soft whimpers from her. It was a minute before another announced its arrival and an intense orgasm followed. Vince let his skirt drop and shot his load on the inside of his cheerleader skirt.

"I'm never going to be able to have Elaine," he said to himself. "but this is the next best thing."