Over the course of the following weeks, Tyler’s love for this new mode of self-pleasure became stronger, and it made him bolder. At first, he waited until bedtime to indulge himself. Soon that wasn’t enough, so now whenever the mood struck him, and no one else was in the house, he dug out the skirt he had rescued and the pantyhose his sister had given him and donned them.
Then perched on the end of his bed, he was able to see the reflection of his lower half in the dresser mirror that he had tilted forward. The sight and feeling of his legs encased in the pantyhose appearing from under the short skirt always excited him. His excitement grew as he slowly hiked his skirt up to reveal his rock-hard cock that was visible through the smoky material of his pantyhose and already leaking precum.
Finally, he flopped on his back and grabbed his cock thru the pantyhose, and commenced to stroke it. He was always rewarded with a massive orgasm. Eventually, he removed his skirt and hose and donned his sleep sweats, and fell into a deep sleep.
It was early on one Friday evening that his sister once again called out to him from the sewing room, it seemed she needed another skirt hemmed. Tyler was instructed to don his pantyhose as their parents left the house and headed to the fish fry and the VFW. When he reappeared clad in his t-shirt and pantyhose, even his sister was impressed by how great his legs and butt looked and looked in her pantyhose.
The moment he mounted the small platform, his sister went to work on the hemline. She was about halfway through when she suddenly stopped and looked up at her brother.
“So, are you enjoying the skirt and pantyhose?” she asked.
“Yes, a lot,” he replied.
“Please tell me that you are doing this because of the way you look and feel when wearing them and that you have no plans to go any further?” she questioned.
“What do you mean and further?” he replied.
“You’re not interested in wearing makeup and allowing some dude to fuck you in the ass,” she replied.
“No way,” he answered in an outraged voice.
“Relax, I just needed to know,” Kara replied and momentarily ran her finger along his thigh, making him forget his anger.
“You shaved your legs?” she asked as sure resumed her work.
“All the guys on the swim team do, is that a problem?” her brother replied.
“No, not at all. I’ve seen pictures of guys that didn’t shave, which made their pantyhose look hideous,” Kara replied.
It was just as Kara finished that her smartphone chirped, because the call was from their parents, she picked up. Tyler removed the skirt and handed it to his sister before leaving the sewing room. This was done as quickly as possible as the pantyhose did little to hide his erection, and he didn’t want his sister to see it.
Meanwhile, Kara was in a heated debate with her folks that was becoming more intense based on the shrillness of her voice. Tyle had just locked the door of his room in preparation for a world-class masturbation session. That’s when he heard Kara tapping on his door, he donned his robe and opened the door for her.
“It seems I had promised to clean the kitchen as we are having guests for dinner tomorrow, and Mom plains to start cooking first thing in the morning,” his sister explained
“So, what’s the problem?” Tyler asked.
“I need to get ready for a party, and between hemming that skirt along with getting a shower and putting on makeup, I am not going to have enough time,” Kara told him.
“What can I do?” her brother asked.
“Clean the kitchen for me, and I will make it well worth your while,” his sister stated,
Tyler had no plans for the evening, so he agreed. He never saw his sister so happy as she danced away, heading for the bedroom and then the master bath.
So Tyler cleaned and mopped the kitchen while his sister readied herself for her party. It was about two hours before both teens finished their tasks. As Tyler sat in the now spotless kitchen, his sister entered dressed for her party, and Tyler had to admit she looked hot as she took a seat across from him.
“These are for a job well done,” she informed him as she glanced around the sparkling kitchen, She reached into the paper bag she was carrying. “Once again, the same rules of silence apply.”
Tyler’s eyes went wide as his sister deposited a black silk and lace garter belt, two pairs of nylons, and two pairs of black panties on the kitchen table. The panties were buttery soft, and the nylons were the sheerest that he had ever seen, along with a pair of shiny black high heels.
“Now, pay attention,” his sister instructed. “Putting on nylon stockings is not the same as putting on your boot socks.”
Kara then pulled her chair next to her brother’s and kicked off her heels, Tyler gave her his undivided attention as she proceeded to show him the proper way to don stockings, she used her own legs as a model.
“Once the nylons are on and attached to the garter belt, then you can slide your panties on, pay no attention to the pics you see in magazines,” she told him.
“I can’t walk in heels,” he informed his sister as he fondled the smooth and shiny footwear.
“I know, but they will make your legs look even better. Plus, it’s not a difficult skill to master,” Kara told her brother.
The moment his sister had departed, he headed to the shower. Later back in his room, he carefully attached the garter around his waist and then slowly and carefully drew his nylons up his legs as he had been instructed. As good as the pantyhose looked and felt, they couldn’t hold a candle to the stockings.
The minute the cool silk of the panties touched his cock, his erection began, and he was hard in record time, and he headed toward his bed. Tyler angled the dresser mirror down again until his legs and feet here visible. Kara was right. The heels made his legs look great.
Tyler eventually kicked off his heels and removed his skirt. The sight of his hard cock pressing against the material of his panties was almost overwhelming as he used his hand to trace the outline of his cock. Once again, Tyler flopped backward on his bed and slowly drew his silky underwear down, he stopped when his cock jumped over the waistband.
He took hold of his throbbing erection, and between the sight and feel of his nylon-clad legs and panties, he shot his load in record time. He used the panties to clean up, and for his second session, he wore only the nylons.
As he got ready for bed, he wondered where this new pastime was taking him.
