Ian picked himself off the carpeted floor and headed to the master bathroom on unsteady legs, the addition of his sister's silky panties to his masturbation routine had made his orgasm even more intense than normal. Now he needed a shower and had to clean the panties that he had just emptied the contents of his cock into and he reasoned that a hot shower would allow him to accomplish both tasks at the same time.

When he finished he wrapped himself in a towel and returned to his room where he hung his sister's panties in the back of his packed closet to dry after patting them dry with his towel afterward. He then hid them in a place where no one could accidentally stumble upon them he then took a seat in his gamer's chair and began to plan.

The panties were nice but Ian wanted more and began making plans to borrow his sister's spare cheerleader outfit, that would be the ultimate experience. This would require all his stealth to accomplish along with a great deal of planning, but it would be worth it.

He planned to borrow it and spread it out on his bed and then climb onto it while imagining that his sister was there wearing it. He would need to wear a condom to keep his cum off of it because that outfit would be a whole lot harder to clean than the panties were.

So the following Saturday after his parents left to go golfing and his sister was sunbathing he crept into the basement to borrow Elaine's spare outfit and carry it to his room still on its hanger. He would only be exposed when he passed the patio doors. He made sure that he moved slowly past the glass doors cause he had learned that it wasn't sound that attracted unwanted attention it was movement. Once in his room, he gently and lovingly placed the outfit on his bed and it didn't take much for him to imagine that he was placing his sister on his bed..

Ian quickly removed his clothing and then stood there with his hard teenage cock bobbing in the air as he removed a condom from the strip in his desk drawer and placed it on his rigid manhood. That's when he heard it, it was the sound of feet ascending the carpeted stairs and his sister calling his name and asking if he was up there, he was going to get caught.

In the space of three heartbeats, Ian quickly weighed the consequences of his next action and decided it was one of a lesser offense. He quickly took the uniform off of its hanger and donned it, he was surprised that it fit him better than he imagined. It was a second later that Elaine pushed open the door to his room and issued a very loud "Ah-ha".

She found her brother standing there wearing her cheerleader uniform and she seemed frozen for a moment as it took her brain a second or two to understand what she was seeing.

"What the fuck is wrong with you and what are you doing in my uniform?" she asked in a loud outraged voice when her voice returned. "I saw you creeping past the patio doors carrying it."

Ian didn't respond and allowed his sister to continue to call him names. He was thankful that Elaine was by herself and not in the company of her cheerleading squad.

"Take that off this second, you sick perv," she ordered.

"Can I have a little privacy?" Ian asked. "I'm not wearing underwear."

Elaine waited a moment before turning her back, now that the anger had passed and she was seeing clearly again she wanted to see him and was forced to admit that her brother looked pretty good in her outfit.

"So, you want to be a girl?" she asked as she approached him.

"No, I just enjoy dressing up like one," Ian lied.

His lie about being a cross-dresser was necessary so Elaine couldn't figure out what he was really up to with her uniform because that would have been disastrous.

"Well, you do have great-looking legs, I'll give you that," Elaine commented as she circled him and took in the sight of her brother's legs that were visible under her short pleated skirt from all angles. "All you'd need is a little instruction,"

"Instruction? What kind of instruction?" Ian asked warily.

"Well, the first thing you need to learn is that good girls don't forget to wear their undies," Elaine told him. "Now, take off my uniform.

Ian was upset because he didn't want instruction, but he went along with it so as not to arouse Elaine's suspicions. She left Ian alone so he could remove and rehang the uniform in privacy. It was about five minutes later that Elaine tapped on his door and asked to come in. Ian quickly donned his robe and admitted her. She carried last year's cheerleader uniform on a hanger.

She collected the uniform that her brother had just removed and then deposited the one she carried on his bed.

"I was supposed to turn it in, but I loved this uniform so I fudged the paperwork so it reads that I did surrender at the end of the season. Now, if you want to play dress up wear this one," she told him in soft tones.

Ian was speechless and unable to move and that allowed Elaine to continue.

"Make sure you wear these under your uniform," she instructed and she removed a pair of white silk panties that were looped around the hanger. " Hang it in the back of your closet when you're not wearing it so Mom doesn't accidentally stumble onto it when she's hanging up clothes.

Once again Ian was speechless as he took in the sight of the uniform on his bed and once again that allowed Elaine to continue.

"We are not going to speak of your new habit to anyone outside of ourselves," she stated and Vince nodded his head in agreement.

As soon as Elaine left his room Vince tried on the uniform that she had left. The scent of her perfume although faint still clung to the sweater and it got him hard in seconds. He slid the panties up his legs and marveled at the sensation they sent through his core. He then stepped into the short skirt and pulled it to his waist and then stood in front of the mirror. he had to admit that his sister was correct, he looked dammed good in her 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."