The more Tyler dressed in his sister's clothing, the bolder he became. He took to wearing his pantyhose under his jeans as he did his daily chores, and he always made sure to wear his t-shirt untucked, as having the waistband of his pantyhose visible would have spelled his doom.

More than once, he was forced to stop his domestic chores and head to his room to masturbate as the feeling of the hose against his naked cock had him hard in minutes. Time moved on, and before he knew it, it was a typical Friday night at his house; his parents had departed for the local VFW, and Kara was getting ready for a date.

Tyler had finished up the dishes and was seated in the kitchen, thumbing through a magazine while waiting for his sister to leave so he could indulge himself. His thoughts were interrupted by the appearance of his sister in the kitchen; she had come to get a can of diet pop from the fridge. Clad only in her robe, Tyler couldn't help noticing how slender and shapely she was.

As she started back upstairs, her smartphone rang, and a loud discussion commenced.

When the call was over, she returned to the kitchen, and Tyler could tell that she was very upset.

"What's the problem?" her brother asked.

"That was Mom and Dad reminding me that I had promised to sweep and mop the kitchen and vacuum the living room. We are having guests for dinner tomorrow," she stated.

"So what's the issue?' he asked.

"I'm in the middle of getting ready for this party I'm heading to, and if I stop and take care of the cleaning, I'll be sweaty and have to start from scratch," she told him.

"That sucks," was her brother's comment.

"I'll make you a deal, take care of my cleaning, and I'll make it well worth your while," she said hopefully.

Now with the exception of his new pass time, Tyler had made no plans, so he agreed to her terms, and as Kara headed up the stairs, he got out the mop and bucket. He was chilling in the kitchen after completing his cleaning when his sister reappeared, and she looked fantastic.

"A deal's a deal," she said as she took a seat opposite him.

From the paper bag she carried, she withdrew a black silk garter belt and two pairs of silky black panties; Tyler's eyes grew wide as she handed him these silky items. The next items she produced were two pairs of black nylon stockings.

"Do you know how to don nylons? It's not like putting on your boots and socks," she informed him.

Kara kicked off her high heels and proceed to instruct her brother on the delicate art of putting on stockings. When she finished, she bade him a good evening and was out the door in a flash. Tyler took his newest gifts and headed to his room, where he wasted no time in donning the garter belt according to his sister's instructions.

The feeling of the nylons being pulled up his legs was like nothing he could have imagined, as was the feeling of pulling up the silk and lace briefs, and he was forced to concentrate so he didn't lose his load before he was fully dressed. He then took a seat on the edge of his bed after tilting his dresser mirror down.

The sight of his nylon-covered knees appearing from under his skirt was better than he imagined. He slowly drew up his hemline until his panties were visible; they were already wet with pre-cum. He grasped his hard cock through the material of his panties and commenced to tug on it.

Between the sight and feeling of his legs in his nylons, it didn't take long before a major orgasm took over, and his teenage body shook as he emptied his load in his silk undergarments. As he lay there floating down from his orgasmic high, he wondered where his new fascination would take him.