Karl returned home a few hours later and showered. Afterward, as he sat at the desk in his room he replayed the events earlier that morning. He still couldn't believe his actions. It had started out yesterday with his being caught staring at Amy. She was the sister of his longtime neighbor and best friend Brad.
Brad seemed to know what Karl was thinking as he stared at his bikini-clad sister's body and issued him a challenge.
"If you want to do her, you have to do me first," Brad informed him.
Now Karl could not believe that Brad had issued such a statement. Of all the people he knew, Brad was the last person he would suspect of being gay. His buddy made him aware of the fact that he had seen him checking him out while he was wearing his Speedo.
Karl bushed with embarrassment. Yes, he had checked his buddy out. He admitted to himself that Brad looked pretty damned good in the skin tight swimsuit, but that's as far as it went.
He was invited over the next day and given a gift of a black Speedo to wear. So the following morning, Karl had gone over to Brad's house and headed to his friend's room. There he discovered Brad stretched out on his bed wearing a fire engine red Speedo and he was a sight to behold. He looked a little different than normal. He appeared softer and more feminine. Karl was asked to reveal his Speedo and then join him.
With a small touch of fear Karl removed his t-shirt and unzipped his jeans to reveal the skin tight swimsuit. He then joined his buddy on the bed. He discovered that Brad was wearing a touch of makeup that made him look like more like a teenage girl than a boy. However, the first time Brad touched Karl he retreated and told his longtime friend that he couldn't go through with it.
Brad responded that if Amy was here to help him he could. He then raised his voice and called out Amy's name. A second or two later Amy entered the room clad in the prettiest lingerie he had ever seen.
She joined them on the bed and talked Karl through the act of fucking his buddy in the ass. As a reward, she took him back to her room where he had the best sex imaginable.
His thoughts were interrupted by his Mom calling up to him that he had a visitor. A second or two later Brad entered his room.
He was void of makeup and his hair slicked back. Clad in jeans and a t-shirt, he looked like any other teenage boy.
"Hey," he said in the way of a greeting.
"Hey," Karl responded.
Brad took a seat on the desk and looked at his buddy.
"I just came over to see if you were all right," Brad said in a low voice.
"I'm OK. It's just a lot to download," Karl responded.
"Now you're the only one besides Amy that knows my secret and I'd like to keep it that way," Brad continued.
"Don't worry about me," Karl responded.
"Amy has been in heaven all morning since you left as she had wanted to do you for the longest time," Brad commented.
"It was all great. All of it," Karl added.
"Good. We'd like to invite you over again on Thursday if you're not busy," Brad continued.
"I've made no plans," Karl responded.
"Excellent. Now I have to ask if you know what roleplay is?" Brad said.
"I don't. What is it?" Karl responded.
"Roleplay is like acting out a play. You pretend that you're someone different and then go with the flow. It's kind of how we played as kids. Pretending to be someone else and making up dialogue as you go along," Brad informed him.
Karl nodded his understanding and Brad smiled.
"Now do you still have that wizard's robe you wore for Halloween last year?" Brad asked.
"Yeah, it's somewhere in the attic," Karl informed him.
"Go and find it and wear it on Thursday," Brad instructed.
"OK. But it's going to raise questions if my Mom sees me leaving the house in a Halloween outfit in June," Karl informed his buddy.
"Then wait until you get to our house before you put it on. Now, I mean the whole costume complete with the wig, hat, and beard. Also, you can't wear anything underneath," Brad continued.
Brad left a few minutes later and Karl headed to the attic as quietly as possible.He didn't want his Mom to hear him and ask questions. He found the hanging garment bag holding the long purple wizard's robe along with the pointed hat, wig, and beard.
He took the bag back to his room and removed the items from inside. As Karl ran his hands over the velvet material he wondered what was in store for me. He was also getting a little excited at the prospect of wearing this soft garment against his naked flesh and his teenage cock began to get hard. He somehow managed to will himself to relax.
Wednesday seemed to crawl by but finally, Thursday arrived. Karl woke and headed to the shower where he cleaned every crack and crevice on his body. After drying off, he then donned his Speedo and called his buddy. He was told the coast was clear so he headed next door. He wrapped his costume in a beach towel in case his Mom spotted him.
Their kitchen door was unlocked as promised so Karl let himself in and ditched the Speedo. He then pulled the wizard robe over his head and donned the beard, wig and pointed hat. As he headed upstairs the movement of the robe against his naked body excited him and he was as hard as a rock by the time he reached the top of the stairs.
He stood outside Brad's door for a moment to collect himself and listened. That's when he heard the moans and pleas for help.
"What gives here?" he said in his most authoritative voice as he entered the room.
It was an act of sheer willpower that allowed Karl not to react to the sight before him. There was Amy flat on her back dressed as a Princess. Her long flowing dress was pushed to her waist and her long smooth legs were covered in white stockings. Her tiny wrists were tied to the bedposts with silken scarves.