Charlie sat in his computer chair, watching as Janice started laying out piles of clothes onto his bed. "Do I really have to try on all of that?" he asked, anxiously.
Janice let out a laugh. "No, silly. I'm just going to use these to throw together a few simple outfits for you. We'll need to see what looks good on you." she said, pulling out a small pile of shirts, placing them on the bed, then neatly flattening out their wrinkles.
Janice had come over right after their classes, just as she had promised. She actually arrived at his apartment just a few minutes after Charlie himself, wheeling in a large suitcase behind her. The moment she arrived, she ordered him to sit and wait in his chair while she got things organized.
Janice peered into the suitcase and saw she had finally emptied it out. Stacks of shirts, shorts, skirts, stockings, and socks sat upon the bed, along with other clothes. Her task done, she turned to Charlie with a smile on her face.
"Now, get up," She ordered. He leapt to his feet, standing before he. She was only a few inches taller than him, but she seemed to tower over him.
"So obedient, I like that, it's going to make this whole process so much easier. Now, we're going to get you dressed up like a girl, but first, I need you to strip down," she said.
"Y-you mean, you mean, you want me to take off everything? Charlie protested.
Janice sighed. "So much for being obedient. Yes, strip down. What are you even worried about? I caught you red handed yesterday, it's not like I'll see anything new."
Charlie blushed as he remembered. She was right, of course, she had seen pretty much everything there was to see the other day. There wasn't much harm in letting her see the rest of him.
"Okay, I'll do it," he said. Janice simply gestured with her hand for him to hurry up.
He started by pulling his shirt over his head and tossing it on the ground, revealing his pale, mostly hairless chest. He unbuckled his belt and let his pants fall to the ground, revealing his boxers and his scrawny legs. He put his hands on his boxers and he hesitated for just a moment.
"Now!" Janice snapped, and he quickly dropped his boxers, exposing his small cock to her.
"Ok, so, let me see what it is we have to work with here," Janice said. She walked around him, running her hands around his body. "Mmm, this is nice, I like your body."
"Y-yeah?" Charlies asked.
"Oh yeah. So slender, so pale, your skin is so soft. You're mostly hairless, there's still a little fuzz, we'll need to deal with that. We won't need much work to make you into the pretty girl that you know you are. Do me a favor, though? Can you bend over the bed?"
Charlie was confused by the request, but he did as he was told, bending over the bed for her, pushing out his ass. Janice's strong hands cupped Charlie's ass, squeezing it gently. She used her hands to spread his ass. Charlie shivered as the movement exposed his asshole to her.
"Oh yeah, this is good. I know a lot of people who would love to have your ass bent over like this," Janice teased. She put her hands on his waist and gently thrust her hips against his ass, giggling as Charlie squirmed underneath her. She slapped his ass, hard, then told him "Ok, now get back up. It's time for your fashion show."
Charlie rubbed his ass as he straightened his back. He wasn't used to being slapped like that, and Janice had slapped him hard enough to leave a pink mark on his pale skin.
"So, how do we start...this," Charlie asked sheepishly.
"You're going to get dressed that way that you normally get dressed, Charlie. You start with your underwear, right? Here, I think these three are a good choice for you. Which do you like?"
Janice placed three panties on the bed in front of Charlie. The first was a simple set of white cotton panties with a small red rose on the front. The next set of panties were jet black, but outlined in dark purple. The last set of panties were bright pink.
Charlie looked at each one, then, slowly, he reached down and grabbed one. He held his chosen panties, the bright pink ones, up before Janice.
"These ones seem cute,"
"Pink huh? It is a classic. What are you waiting for? Put them on," Janice said.
Charlie blushed, his hands still. He felt like he wanted to put them on, but he just couldn't. Something, some sense of shame or peer pressure weighed down on him. Even if no one found out, he would always know that he'd worn panties, and worse, panties he'd chosen himself.
"What's the matter?" Janice said, frowning.
"I...Janice, I can't, this is too much," Charlie protested, handing her back the pink panties.
Janice put her hand on her face. "And things were going so well. I should have seen this coming," she muttered to herself.
"I'm sorry, I didn't mean to lie to you," Charlie said.
"It's not me you're lying to," Janice said. She put her hands on his waist and pulled him in close, her lips just an inch away from his own. "I know I'm right about you. I know you want to be a girl."
"But-" Charlie started to protest, but Janice quickly shushed him.
"No, listen. I know this is a big change, and I know change is scary. But trust me, this is the right thing to do. And I know how to help. If you put on the panties, and the rest of your girly clothes, I'll make you cum. Not by whispering in your ear, no, you'll get to feel what my hand feels like tonight."
As she said that, Charlies cock started to twitch, pressing against her shirt eagerly. Janice smiled down at him, "Looks like someones excited. So, will you try them on? For me?" Janice asked.
Charlie nodded his head, and Janice giggled at how quickly he'd changed his mind.
"Then put them on," she said, pressing the pink panties into Charlie's chest. She took a step back to watch.
Charlie meekly took the panties. He raised one leg and slid it into the panties, then the other, and pulled the panties up around his waist. They fit rather well, clinging to his body, and they easily contained his small cock.
Janice clapped her hands together. "Such a good girl," Janice cooed. "Now, let's get you a full outfit. Here, I have a few ideas."
Janice put her hand on his ass and directed him back to the bed. "Now for shirts, here's a few choices. Notice it's light colors, we don't want to clash with your pale skin. Well, unless you want to go through a goth phase."
Charlie looked down at the shirts. There was a black tank top, a pink button down blouse, and a babydoll tee showing the name of some band Charlie had never heard of. Charlie felt the blouse was too much work, and since he didn't know the band name, he figured the tank top was the safest choice. He grabbed it and pulled it over his head.
"Look at you? No hesitation now, I see," Janice laughed. "I like it. Simple and casual. Hmm, I was worried my clothes would be too tight on you, but it looks like they're too loose! We'll need to get you some clothes of your own before you go out in public, can't look like a mess when you're looking for a guy, but these will do for now. Time for your next choice!"
Janice layed out a set of bottoms for him. There was a pair of hot pink booty shorts, a knee length blonde skirt, and a set of light brown capri pants. Charlie almost grabbed the skirt, but instead he grabbed the pink booty shorts. He slipped them with ease.
"Pink again, huh? Sounds like you're a really girly girl, I'll have to keep that in mind," Janice teased him. "Come here, take a look at the new you."
Janice pulled him over to his dresser, where he had a small mirror set on top. Charlie never put much thought into his clothes before, the mirror was mostly used to make sure he hadn't missed anything when shaving. But now, he could see himself.
"Oh wow," he muttered.
His face still looked like a boy's face, with the fuzzy stubble along his jaw, and his hair wasn't long enough to be girly. But moving down his body, his masculinity became less obvious. His thin arms and legs looked naturally girly. Janice's clothes were indeed hanging loose on his body, but, in his case, it worked to his advantage, making it look like he may be hiding a pair of small breasts underneath his shirt.
He looked more like a girl in one day than he ever thought he would.
"I know, right? You were built for this, Charlie. A little makeup, maybe a wig, and I could take you out today to pass as a girl. But we both know you're not ready for that. Well, what do you think? Janice asked.
"I like it," he said quietly.
"Oh? And why do you like it?" Janice pressed.
"I like it because...because I look pretty," Charlie confessed.
"Mmm, that's right you do. And trust me, you're only going to get prettier from her. Soon enough, no one would ever be able to guess that you once pretended to be a man." Janice said.
Her words confused him, bothing stinging him and stirring something inside him that he often tried to bury.
"Now, are you ready for your reward?" Janice asked.
Charlie eagerly nodded his head, "Yes, please, Janice," Charlie said, his cock still rock hard, precum starting to leak into his panties.
Janice walked over to the bed and sat down, then she patted her thighs. "Come on, sit down here and let me take care of you," She said, smiling at him.
Charlie walked over and sat down on her lap like a woman would sit on a man's lap. He uncomfortably squirmed underneath her. Janice reached down, unwrapping him like a present as she pulled his booty shorts and panties down around his knees. His small cock was rock hard and ready for attention.
"Are you ready for this?" Janice asked.
"Yes, Janice, oh god, I can't wait to feel your hand around my cock," Charlie whimpered.
Janice slapped his cock, and Charlie whimpered in pain.
"No, no, no! And you were doing so good," Janice said, displeased. "Remember, you don't have a cock."
"But I-" Charlie replied but Janice cut him off.
"No, you don't. If you had a cock, I'd need my full hand for this. But I only need a finger or two for a clit," Janice said as she lowered her hand. She used two fingers and started to rub them against Charlie's cock.
Janice started to move her fingers along Charlie's shaft, easily rubbing up and down his entire shaft in quick, circular movements, while pressing his cock down against his down crotch. The sensation was so bizarre, but Charlie couldn't help but groan as she rubbed against him.
"That's not right, either," Janice said, slowing her fingers. "Girls' moans are higher pitched than that. Give me a good, girly moan."
Charlie blushed, but did as he was told. "Ohh Janice, your fingers feel so good," he moaned in a high pitched voice.
"Mmm my fingers feel so good, where?" Janice asked.
"On my...on my clit," Charlie said in his girl voice.
"That's right, good girl," Janice said. She started to move her fingers faster, bringing Charlie to the edge, but she sensed him approaching his limit, and slowed down yet again.
"Open your mouth," Janice commanded.
Charlie immediately opened his lips, and Janice raised her other hands to his mouth, sliding two fingers between his lips.
"Suck and lick my fingers, get them nice and wet," she told him.
Charlie started to wiggle his tongue over her fingers, moaning onto them as she kept going with her cycle of teasing him, then letting him cool down.
Eventually, Janice pulled her fingers from his lips and brought them down and around Charlie, out of his sight. She stopped touching him altogether, and she leaned in close, talking directly into his ear.
"Something is about to happen. You are going to relax and take it. It might be uncomfortable, but, it needs to happen before I let you cum. Do you understand?" Janice asked.
Charlie nodded his head. His small cock was swollen and leaking precum, he was so eager for release, he would let her do anything to him to get it.
"Good girl," Janice said. She started rubbing his cock again, but as she did, her other fingers started to slide between his ass cheeks. A finger started pressing against his asshole, and it was pressing hard.
Charlie's eyes go wide, but before he could react, Janice's voice filled his ear.
"Remember, just take it," she said and one of her fingers slid inside him. "There we go, what a good girl. That's what a good girl does, let's others inside her body."
The finger in his ass felt uncomfortable at first. It was slowly wriggling its way deeper inside him, violating him in a way no other person had before, but the fingers on his cock just felt so good, he needed this, he had no choice but to take it.
Janice's second finger slipped in as well, and together, the two fingers started pushing deeper inside her. Charlie's tight ass clenched down hard on her fingers, making her progress slow, but she found what she was looking for.
Charlie's eyes went wide and a loud moan escaped his lips. "What is that feeling?" he whimpered.
"That's your g-spot" Janice said. "Doesn't it feel good? It's okay if it does. You've been such a good girl, you can cum whenever you want to."
The fingers inside him kept brushing against that special spot inside his ass, and the fingers on his cock started rubbing furiously. It was too much.
"Oh Janice, Janice, I'm cumming!" Charlie screamed, and his cock started to twitch, and he came. Not only did he cum, Charlie came harder than he ever had before, his cock exploding out thick ropes of cum, some of which splattered against his new clothes, the rest landed on Janice's fingers.
Charlie's breathing was deep and ragged as he rested himself against Janice, exhausted. Janice stopped moving her fingers, but the two fingers in his ass stayed where they were.
Janice raised her hand to his lips. It was the hand that she'd rubbed his cock with, and they were covered in drops of his seed.
"You did so well today Charlie, but there's one more thing. I need you to taste this," Janice said.
Charlie looked her in the eye. "Do I really need to?" he asked, almost pleaded with her.
"You need to get used to the taste. Just give it a lick, that's all you need to do," Janice said.
Charlie lowered his mouth to her hands and opened his lips. He used his tongue to lap up a small droplet of cum, and his mouth was full of the salty, bitter taste of his own semen. He didn't hate it, but couldn't help but be embarrassed at being forced to taste his own cum.
"What a good girl. You'll thank me, trust me, you want to be used to the taste before a man explodes in your mouth. I almost threw up when I first had to taste it," Janice laughed. As she did, she slowly pulled her fingers out of his tight ass.
Janice gently rolled Charlie over onto the bed and off of her lap. She went through the remaining piles of clothes and picked out a few different outfits for Charlie, while he took the time to compose himself.
"I'm going away for a few days," Janice told him. "We'll take the next step when I come back. In the meanwhile, Charlie, I want you to keep dressing like a girl around the apartment. I put these together for you, but feel free to dress yourself, you did a good enough job the first time around. But you will send me a picture of you, dressed up, every day."
"What happens if I don't?" Charlie asked.
Janice looked down at him, contempt in her eyes. She stood over him on the bed, raised her shoe, and placed it down on his now flaccid cock.
"You don't want to know what happens when you disobey me," she said.
"No, I got it, pictures everyday," Charlie said, panicked.
"Good girl. Now, don't get up, I'll show myself out. And trust me, Charlie, you're going to love what we're doing next."
With that, Janice flashed him a vicious smile and left his bedroom. As she left, Charlie didn't know if he was more excited or afraid for what comes next.