Jeffry pulled off his shirt and quickly dropped his shorts and underwear. His hard, little cock jutted out from his crotch. It was so stiff and Jeffry was so horny! He put on the pink panties first, then, he tried to put on the bra but he was confused by the clasp.
"Here, let me help." Billy stood up and helped Jeffry put on the bra, carefully avoiding the hard dick poking out from Jeffry's panties. "My sister does it this way." Billy placed the bra on Jeffery backwards and showed him how to work the clasps. He then spun the bra around. Jeffry put his arms through the loops and adjusted the bra. The lingerie fit, but just a little loose.
"Billy, how do you know how your sister puts on a bra?"
"I peek at her, of course." Billy said. "Every chance I get."
"Oh. Yeah," Jeffry said, "I would too." He almost felt like Billy's sexy sister, standing up nearly naked, wearing her bra and panties.
"Here, stuff these into your bra." He handed Jeffry a pair of rolled up socks he pulled out from under his pillow and he quickly placed them in the bra, adjusting and fluffing up his new breasts until they were smooth, even, and full. Jeffery never even considered why Billy had a pair of socks ready and waiting under his pillow.
"Wow, Jeffry," Billy said, encouragingly, "You make a pretty hot chick!"
"Thanks!" Jeffry said, sticking out his chest proudly. He liked the feeling of the silky underwear against his naked skin. His cock felt so good! And, and he liked that Billy said he looked hot! He tossed his hair back and forth like the girls in school did.
"Almost ready," Billy said. "And now, for the final touch!" He handed Jeffry a tube of bright red lipstick.
"What?" Jeffry asked. "Lipstick too?"
"You have to really look like a girl, Jeffry, or it is not going to work." Billy said. He smiled at his sissy friend and offered more encouragement. "I can almost feel myself getting harder already. You look fucking amazing, Jeffry! Go look in the mirror!"
Jeffry carried the lipstick to the bedroom door, and looked into the mirror hanging on it. 'Shit,' he thought, 'He did look hot in his pink panties and bra!' He played with his hair, trying to make it more girly. 'Wow,' he thought, 'I make a prettier girl than I do a boy! Except for the stiff little pecker poking up from my panties!' He giggled, then looked at the lipstick quizzically; he took off the cap and twisted the base until the small, pointed, red shaft appeared. 'I never noticed how it looked like a little dick before,' he thought. He would never watch a girl apply lipstick the same way again. He got close to the mirror, pursed his lips, and brought the little cock to his lips. He clumsily applied the lipstick with a nervous hand. Once, then twice. Finally, he turned around. "I'm not very good at this, Billy." Jeffry had lipstick all over his lips. He almost looked like a circus clown! Billy started laughing.
"Ha, ha, ha! Jeffry, you look so stupid! Don't you know how to put on lipstick? Shit!" He continued to laugh out loud.
"I tried, Billy, I've never done it before," he cried. "Can't we just skip it?" he pleaded.
At that very moment, Billy's bedroom door swung open wide and banged against the wall. His sister Becky's angry voice exploded as she stormed into the room. "Billy! Are you stealing my underwear again? Now you are taking the clean ones too, you little fuck!" She stopped suddenly, taking in the scene before her. She began to laugh.
"What the fuck are you two perverts up to? Those are my fucking bra and panties, you sick little shits!" She didn't know if she should act angry or laugh at them. "My lipstick too!" she cried, seeing Jeffries hilarious face.
"Uh, Jeffry wanted to try them on," Billy explained. "He wanted to know what it felt like to dress like a girl, didn't you Jeffry?" He stared at his friend, compelling him to agree with him by only using his firm gaze.
Jeffry noticed his friend's expression. "Uh, yeah. I just wanted to know what it was like. I'm sorry, Becky." Jeffry hung his head down, ashamed. His hard-on quickly wilted, leaving a wet spot on her clean panties.
"I was just helping him out, Beck, you know, like a friend should," said Billy.
"Yeah, right. Who knows what kind of gay shit you little perverts were going to do." She suddenly noticed the slimy spot Jeffry had made on her panties. "You got my panties wet! I was going to wear them to see Jason! Now, I'll have to wear the black ones. Damn-it Billy, your girlfriend got his slimy dick juice on my favorite panties!" She acted angry, and then smiled at the boys, laughing at her insults and imagined what they would be doing right now if she interrupted. She suddenly wished she had waited a few more minutes. Feeling naughty, intrigued, a little bit horny, and slightly evil, she said, "She is not very good at putting on lipstick, is she?"
"No, she isn't." Brother and sister shared a laugh together. Jeffry turned even redder.
"Maybe someone should show her how to put on make-up like a girl?" Becky grinned, imagining how she could easily turn Jeffry into a pretty, slutty, little girl. What would her spying, perverted, horny little brother, Billy want to do to his friend then, she wondered.
"Would you really help him, Sis?" Billy asked. "Would you show him, I mean, her, how to do it right?"
Jeffry's eyes widened until they were huge! He was mortified. How humiliating! He finally thought to cover himself up, but it was too late now.
"Hmm. Maybe I could help…" She considered what she could get out of the two perverts. If they wanted to play dress up and suck each other's little dicks, what did she care about? As long as they stayed out of her good clothes and underwear. She had an idea.
"All right," she said, "Mom and dad just left and I'm supposed to watch you sick little faggots and have the house clean before they get home tonight. Here's the deal. I could show your little sissy friend how to put on some slutty make up if you little boys clean the house and cover for me while I'm gone. That way, I can go to Jason's house and have a nice long fuck." She enjoyed the boy's shocked expression when she mentioned fucking her boyfriend. She noticed Billy nodding imperceptibly. She quickly renegotiated, pushing her advantage "Oh, and Billy, one more thing, you get to volunteer to clean up the dinner dishes for me all week. Do we have a deal, fuck-heads?"