It was around nine on Saturday morning that Spring day when Tyler's sister Kara called him to the sewing room. Yes, you read it correctly, it said sewing room. Kara along with her mom were gifted tailors and the contents of the room reflected it. They turned their skills into a very lucrative side job.

"What ya want?" her brother asked in a slightly perturbed tone as he entered the room.

Kara tossed him a pleated mini skirt and told him to put it on as she needed to adjust the hem, he of course refused and tossed it back to her.

"What's the problem?" she asked. "It's not like you haven't done it before."

She was correct. Over the course of the last couple of years, he had been the dress dummy for his mom when his sister wasn't home and visa versa when alterations needed to be made. It was usually a dress or a gown that needed attention and due to his height, he was a perfect choice. He simply stepped into the garment and stood patiently as the pins were inserted in various places, it was simple.

"The problem is that this skirt is too tight to go over my jeans," he replied as she tossed the skirt back to him.

"So you slip off your jeans," she responded.

"Not going to happen, wearing women's clothing is borderline sissy material," her brother shot back.

"Please," she said in a pleading tone. "I need this skirt for a party this evening."

Tyler was surprised at his sister's tone, she never begged for anything or showed frustration and despite being a few years apart in age, she had always treated him well. There was none of the intense and loud sibling rivalries that his buddies told him that they endured daily with their sisters.

"There's ten bucks in it for you," she quickly added.

"OK," Tyler after a long silence.

Kara thanked him one hundred times as she pulled out the folding screen for her brother to step behind she then handed him the skirt over the top of the screen. He removed his jeans and then very gingerly stepped into the short and silky skirt.

Once zipped up he stepped around from behind the screen and headed toward the round alteration platform and mounted it, and that was when it happened. The feeling of this soft skirt brushing against his bare thighs caused a tingling in his cock which meant an erection was on its way. This had never happened before, of course, he had never been dressed like this, normally the dresses and gowns were put on over his clothing.

Kara was already waiting with her pins and chalk and went to work the moment he stopped moving.

"Legs together,' Kara politely requested once he had mounted the platform.

Tyler stood at attention and the heat in his groin was undeniable. He hoped that Kara didn't see the bulge under her skirt. It was when the back of her fingers occasionally brushed against his bare legs to protect them from the pins that she was inserting into the hem that increased the hardness of his cock.

"How are you going to get past Dad and Mom wearing this?" Tyler asked in hopes that talking would take his mind off the sensations he was feeling.

"I'm going to wear it under a knee-length skirt and change it when I get to the party," she responded as she continued to place pins into the hemline. She could sense her brother's impatience. "Almost done," she added.

"You know if you had learned the lessons that grandpa tried to impart to you then it would be me on the platform and you adjusting the hem, " she added.

Vince agreed rather than apologize. He had tried to learn from his grandfather who was a master tailor, but had no patience. He could sew on a button and repair a tear and was happy with these skills.

"You have great-looking legs for a male, maybe I should join the swim team and improve my legs," she commented.

Her brother had no response. He just needed to get this skirt off.

"Finished," she announced about a minute later. "OK, you know the drill."

Tyler gingerly stepped off the platform and headed for the folding screen. As he did this he caught sight of himself in the skirt in one of the many mirrors in the room and he had to admit that his sister was correct, his legs looked great. Once behind the screen he carefully removed the miniskirt and handed it over the screen to his sister, he then redressed and it was a little difficult what with the bulge in his boxer briefs.

The moment he stepped out his sister handed him a ten-dollar bill and kissed him on the cheek.

"Thank you," she said and then took the skirt to the sewing machine and commenced making the alterations permanent.

Tyler headed to his room and once behind his locked door commenced to strip down to his undies, the small stain on the front told him that he was leaking per-cum. He flopped back on his bed and removed his underwear and then grabbed his hard teenage cock and commenced stroking himself he recalled how it felt wearing that skirt and how it looked on him.

He lost his load on his lower belly in record time, it was one of the most intense orgasms he had experienced to date. As he enjoyed the last of his orgasmic high he had time to think. Masturbation was a constant factor in his life since his girlfriend broke up with him, and he never lost an opportunity to pleasure himself.

As he floated down from his orgasmic high a new idea invaded his thoughts. He thought about the skirt and how great it felt and looked on him and he wondered what it would be like to wear it for his next self-pleasuring session. He waited until his sister had left for her party and his parents were watching television before exiting his room and heading to the sewing room.

He looked around the room using a flashlight instead of turning on the ceiling light because that would have let his parents know that he was in the sewing room, and would have spelled trouble. Secrecy was now priority one.

He found a rack of completed garments awaiting pick up and ones awaiting work, not what he wanted. It was in a "rag bag" that he found an answer to his search. The skirt like the last one was also lightweight and silky to the touch, and he quickly departed the room with his prize.

Back in his room, he removed his jeans and briefs and donned his Speedo, he had always loved the way it looked and felt on him. He then stepped into the borrowed skirt and pulled it up, it was even shorter than he thought and that excited him.

He had no full-length mirror in his room, the only mirror was on his dress and it failed to show his lower half. He remedied that by tilting the dresser mirror forward as far as it would go and then took a seat on the bed and his legs were now visible.

He reached under his skirt and took hold of his cock through the cloth of his Speedo and commenced to rub it, The sight and sensations were better than he expected and he quickly lost his load. Once again as he enjoyed a slow descent from high he began to plan his next session. The skirt and Speedo looked and felt fantastic, but something was missing.

Tyler hid the skirt in his room not worried about it being missed as it had been earmarked for rags. He took his Speedo into the master bath and washed it in the sink. this was hung in the back of his closet. He returned to his bed and was sound asleep as soon as his head hit the pillow. He dreamed about wearing more of his sisters' clothing.

Over breakfast the following morning, his parents announced that they were heading out this evening. Kara added that she also had plans and although his exterior was calm, Tyler was overjoyed. The house would be empty which meant he could wear Kara's clothing again without fear of discovery.

As he helped with the household chores after breakfast he thought about the pleasures that the evening would bring, He continued to fantasize as he mowed and trimmed the lawn with his Dad. As the daylight began to fade there came a knocking on his door, his sister wanted to talk to him.

"Here, these things are for you," she stated as she tossed a plastic shopping bag at him.

Inside the bags were two pairs of black pantyhose. Tyler didn't say anything; he could only look at his sister.

"I found my old skirt missing and figured that you borrowed it," she said calmly.

Tyle was about to protest, but Kara silenced him.

"Hide them well 'cause if you're caught with them, I'm going to play dumb," she informed her brother. "Just stay out of my room and lingerie chest or I sell you out."

The minute the house was empty he slid on the pantyhose and then the skirt, as good as the skirt felt against his flesh the pantyhose increased the pleasure. Once again he angled his dresser mirror down and took a seat on the edge of his bed. The sight of his nylon-covered knees was almost too much for him and he almost lost his load right then and there.

Once again, he watched as his hand slid under his skirt, the feeling of the silk pantyhose against his hand and hard cock were beyond description. He grabbed his cock thru the pantyhose and commence to stroke himself until he emptied his load in his pantyhose.

As he lay there, feeling his cum-filled pantyhose cool off, his mind began to wander. He was on an unknown path and was not sure of the final destination, but he was prepared to enjoy the trip no matter where it took him.