Perverted Education

by TalesFromWherever (ao3)

Chapter 1: Introduction

Chris woke up to the feeling of someone rubbing his shoulder.

"Get up sleepyhead" came the voice of his guardian, Emma. "It's the first day of school!"

Chris rolled over, stretching one arm out as he used the other hand to wipe at his eye. His mother was the captain of a cargo ship and she had left on another voyage a week ago. Emma had stayed with him on and off since he was 13, helping get him to school on time and making his meals. Now that he was 18 he didn't feel the need for her as much, but his mother insisted. "I'm awake, I'm awake!" he groaned, nudging her hand off of his shoulder. He had been having a nice dream, a very nice dream, and didn't want her to notice the tent that was growing in his pajama pants. "Just give me a few minutes and I'll come downstairs" he pleaded.

"Alright, the batteries were out in my alarm clock so you're running a bit late. I'll make some food for you but hurry up!" Emma called back as she walked out of the room.

Chris looked over at his clock and groaned, he didn't have any time to take care of his tent issue if he wanted to make it to school on time. He hopped out of bed and looked in the mirror, checking himself out. His black hair was a bit long for a boy's, and it was shaggy and unkempt. He had never really liked any of the haircuts he was given, so he just let hair style fall to the wayside. His body was skinny and devoid of muscle, it wasn't like he was hitting the gym on the regular. He pulled off his pajama pants to reveal a pair of tighty whities. The tent below was nothing impressive, and there was already a wet spot forming at the crotch. He groaned and pulled off the underwear, tossing it into his hamper as he went looking for another pair. Chris put on a clean pair, groaning as the tight fabric already had another wet spot. It was going to have to do.

His uniform hung at the front spot of his closet, covered in the same dry cleaning plastic from the previous year. Most of the kids at school had to get new ones each year due to growth spurts, but Chris never seemed to hit his. He still fit into the same uniform from sophomore year. The now-senior removed the cover and started getting dressed. He pulled the black pants over his slim legs and up to his waist. Chris reached into his closet and took a belt off a hook before guiding it through his belt loops. He didn't really need a belt to keep his pants up, but a lifetime of having them pulled down made him extra cautious.

He took out a white button down shirt and slipped his arms into it. It was the smallest male size they had but he couldn't even fill that out. Chris buttoned the shirt up before putting on his black tie. He pulled the school blazer on top of it, turning to look in the mirror again now that he was dressed. The uniform was supposed to build confidence, but he just felt like a little kid in adult clothes. He looked at the clock, somehow time had slipped away from him and he was definitely going to be late. He grabbed a pair of socks and his dress shoes and rushed downstairs.

"Don't you want some breakfast?" Emma asked from the kitchen as she saw Chris rush by, hopping as he put on his socks and shoes.

"Don't have time, sorry!" he said as he grabbed his bag and rushed out the door. Because the school he went to was private, there was no bus to pick him up. Most of the parents dropped their kids off, some even had their chauffeurs do it. Emma rarely was on time with her own life, so Chris had to walk a few blocks instead. On the way he passed a man jogging, hopping out of the way as the sweaty runner didn't make an effort to move as well. Chris turned and looked at the man, annoyed, but there was nothing he could do. He continued on towards school.

The hallways were empty as Chris reached the classroom. He grabbed the door handle and waited a moment, anxious about being late on his first day. He couldn't believe he had Ms. Buxton for homeroom again, the woman had it out for him and never let up. He sighed and opened the door, better to get it over with now. Chris didn't make it two steps into the room before Ms. Buxton's cutting words filled his ears. "Mr. Sellers, another year but still tardy I see. No worries, you can spend your first day back in detention." The school year had barely started but Chris was already in the doghouse. He could hardly believe it as he retreated to a seat in the back, not eager to catch any more punishments for the rest of the day. The only seat available was behind one of the school bullies, Ryan. The larger boy turned around and snickered at Chris as he sat down and shrank into his seat.

The first day went by uneventfully as Chris managed to avoid any other conflict for the day. Usually Chris was excited for the last bell of the day, but today it didn't signify freedom. Before he could head towards detention, his Chemistry teacher asked for a word. By the time they stopped bending his ear, the hallways were empty again and Chris was worried about being late a second time. He rushed towards the English hallway, but stopped when he noticed a pink book-bag sitting against the wall with no one around.

The timid boy picked up the bag, wondering if the girl who dropped it might be grateful that he gave it back. It would also make a good excuse for being late to detention, or so he thought. All he had to do was find out whose bag it was. Chris unzipped the bag from the top and reached in, feeling a book and some fabric. He took out the book and looked it over, but there was no name in it. Reaching back in, he took hold of the fabric this time, wondering if it was a t-shirt that might have a name on it. Instead, he pulled out a pink pair of panties, dangling in the air as he looked them over.

"EEEK! WHAT ARE YOU DOING?" Came a shrill shriek. A young girl that Chris didn't recognize came running up, grabbing the bag and the panties from Chris. "WHATS WRONG WITH YOU?" she continued.

Chris realized this looked bad and raised his hands defensively, waving them to try to shush the girl. "No, no, no! I just found your bag and I was going to..." he started, but before he could finish he heard a familiar voice.

"Mr. Sellers, what is going on here?" Ms. Buxton asked as she strode up from behind.

"He stole my bookbag and was looking at my panties....er, clothes!" the girl said, gripping her bag tight.

Ms. Buxton shot Chris a look that could cut glass. She put her hands on the girl's shoulders and turned her away "I'll handle this, you just get down to your ride young lady" she coached, pushing the girl away before turning back to Chris. "And you" she said sternly, crossing her arms and staring him down. "Obviously, detention is not enough of a deterrent to make you act like an upstanding member of society. So instead I have some real world homework for you to do."

The teacher pulled the teen boy to the side, making sure no one was around to hear. "If you want to steal girl's panties so much, then perhaps you would like to wear a pair?"

Was she being for real, Chris thought to himself. He wanted to speak up and call her crazy, call her bluff, just say something, but she waved him off before he could speak. "You will owe me $25 per week, to be paid on Friday. But if you are good and wear panties to school underneath your uniform, I will take off $5 per day. Its that or I could have you expelled."

Her last sentence cut deep. This was a private school, most of the students there were either exceptionally smart or exceptionally rich. Chris was neither, but his mother had worked hard to be able to afford to get him in. She would kill him if he got expelled, even if he was being put in a bad position. He realized he was beat and looked down at the ground, nervously shuffling his feet. "But. Ms. Buxton, I don't have any girl's panties.." he argued, hoping that would get him out of it and not enrage her anymore.

"I'm sure you can find a way to procure a pair, you did just try to do that after all. Rather than spend your time in detention today you may go home and figure it out. I will see you for detention tomorrow after school instead." And with that, Ms. Buxton turned on her heel and walked back towards the English wing.

Chris felt somewhat numb as he walked towards the entrance to the school, wondering just how he got in this mess and what he could do to get out of it. Maybe Ms. Buxton would forget about it after a week, he just had to get by for a little bit, he thought to himself. But where was he going to get panties? He dragged his feet as he walked out the door, going over his options.

He could steal some from his mom, but that was kind of gross. There was Emma as well, but she was a bit on the thicker side. The last thing he needed was to get caught by Ryan or anyone adjusting a pair of loose panties underneath his uniform. There was always the mall, but he didn't have a lot of money and walking into a women's underwear store as a guy? He could feel his skin getting hot and red just thinking about it. Finally, a light bulb dinged on in his head.

Chris pulled out his phone and texted his best friend, Chelsea. She had been his best friend since elementary school but she had switched to a different private school for high school. Chelsea didn't care about Chris' low reputation at school, or the fact that his family wasn't wealthy like hers. They were just friends, through and through. "Hey Chels, was today your first day as well? I just got out and boy, what a day. Think that maybe you'd like to hang out?" he texted, his phone murmuring as the message went through.

A moment later his phone murmured again as Chelsea's response came in. "Hey Chris! Yeah it was my first day back as well. I just got back from vacation yesterday so it was such a shock. I'd love to hang out, wanna come over to my parents new place? Its on Sweetwood Street instead of Beecher."

Chris sent back a thumbs up and then adjusted his book-bag before heading off to her house. When he arrived, he could hardly help but marvel at the new place. Chelsea's parents old house wasn't anything to sneeze at, but it didn't have columns. Chris felt nervous as he knocked on the door, half expecting a maid or servant to answer. But when the door opened, it was his friend Chelsea standing there. She was a bit taller than Chris and reached out to grab him for a hug, pulling his face towards her chest. He felt his blood get hot, but did his best to hide it.

"Hey Chels, I missed you too" he choked out as he was caught off-guard. He had always harbored a minor crush on the girl, partially because she was one of the few girls who would give him the time of day, but she never really showed any interest, beyond being a friend, back. He pulled away, not wanting to have a similar tent situation as he did earlier and feigned interest in the house. "This place is seriously nice, what happened to the old house? They just get bored?" he joked.

"Yeah, they had their eye on this one for a while and as soon as it was on the market they snatched it up. Want me to give you a tour?" she asked.

Chris thought about his little mission, but if he was too obvious he would never complete it. "Sure, lead the way" he said nonchalantly as he took his shoes off and followed her into the house. Chelsea had already changed from her uniform into a pair of black yoga pants and a t-shirt, making Chris feel a little overdressed for their hang out. He walked behind her as she told him about the place, he had never seen a house with its own massage parlor and beauty salon in it before!

After showing him the massive kitchen, the movie/gaming room, the tennis court and the indoor pool, Chelsea brought Chris upstairs to the room that mattered, her bedroom. It was easily twice the size of his, with a king size bed and room left over for couches and a "den" area. Chelsea brought Chris over to the couch and turned on the TV before tossing him the remote.

"Here, find something for us to watch and I'll get us snacks" she said before leaving the room.

Chris fiddled with the remote for a moment to make it look like he was trying to find something. When he felt the coast was clear, he hopped up from the couch and rushed over to one of the doors, finding himself in a bathroom. He cursed in his head as he closed the door and ran over to the last one, finding his way into a large walk in closet. It was overwhelming, like a library but with dresses and outfits. Chris couldn't imagine owning so many clothes before finally bringing himself back to his task at hand. He looked for a dresser, armoire, bins, anywhere that Chelsea might keep her underwear.

There were drawers built into the wall and Chris began pulling them out. Sock drawer. Bra drawer. Getting closer. Underwear drawer. Bingo. He silently asked Chelsea to forgive him as he plunged his hand in and searched for something he could wear. The drawer was full of things that were a bit too skimpy for him, thongs and g-strings, even ones with little rhinestones connecting the fabrics. He couldn't wear that to school, but that was all she had in this drawer. There had to be another one.
He tried the next drawer and was relieved to find fuller panties. He picked up the top pair, checking them out to see that they would cover his...ass. He looked at the words on the cheeks of the panties, "Daddy's girl". He couldn't wear that, no way! Chris put the pair down and picked up another, these one's studded with "Yes, please". Didn't Chelsea have any regular underwear?! He groaned to himself as he felt time ticking away. He began to rip through the panties, working his way down until he found a pair of plain purple ones.

Chris could hear footsteps heading back towards the room and knew he was out of time. He stuffed the panties into his pocket and put everything back the way he found it. Not wanting Chelsea to hear him plodding around, he tip toed out of the closet and closed the door behind him. Chris managed to hop onto the couch just as Chelsea walked in with a tray of snacks. "So, what did you decide?"

He hadn't had any time to pick something out, so whatever was on screen was going to have to do. "Oh you know I thought we could watch...." he looked at the screen, noticing now that it was a ballet done by a local troupe. He gulped, not knowing how to even describe it "....the ballet?" Chris could feel himself turning red, there was no way she was going to buy that, she was going to know something was up.

"Oh, how cultured, I didn't know you liked ballet Chris!" Chelsea said with a smile, putting the tray of sodas, pretzels and cheese on the coffee table. She sat down next to him, closer than she usually did, and gave him a light smile. Was she being flirty with him? "You know, I used to do ballet when I was younger, Mom still buys me shoes and outfits hoping I'll get back into it."

Chris imagined Chelsea in a tight leotard, twirling around like the dancers on the screen, and had trouble hiding his enjoyment. He wanted to tell her that she should dance again, that he would love to see that, but the pair of panties was burning a hole in his pocket. Chris felt so much more nervous around her than he ever had before.

After what felt like forever, the dancers finally bowed and the ballet was over. Chris didn't want to seem too eager to get home, but every moment he stayed was a chance that he would be found out. He stretched his arms out like he was tired and faked a yawn, although after watching an hour of ballet it wasn't that much of a fake. "Well, I've gotta get home, I've still got some studying and stuff to do. Can you believe that, on the first day?" he said, selling his story as best he could.

"Of course, Chris! It was really good to see you! We should hang out more often, I have a few things I think you might like watching" she said with a bit of a smirk.

Chris didn't know exactly what that meant, but he hoped Chelsea hadn't gotten the wrong idea from the ballet thing. He collected his shoes at the door and gave the girl a friendly, one armed hug before departing. He had made it.

Back at home, Chris closed and locked his door. He pulled out the pair of purple panties and put them on his bed, pacing around for a minute. His teacher really wanted him to wear these, to school? Or he could always just be expelled. He knew how it was with the other students, if the girl was rich enough it didn't matter what had or had not happened. People got kicked out just because one family had enough money and didn't like the other.

Chris stripped off his uniform down to his tighty whities. He picked up the pair of purple underwear and held it against his crotch. It wasn't that much different than his, it was almost the same size! Oh well, how bad could it be, he thought to himself. Chris pulled down his underwear and replaced it with the panties. He shivered as he pulled the soft fabric up over his small package. He'd never felt anything like that before! It didn't take long for the sensation to run its course, and his small cock grew hard.

He groaned as he felt his cock harden, the tight panties creating a sensation loop. He moaned as he humped the air, feeling pleasure just from wearing the girl's underwear. A small dark spot appeared at the tip of his cock, the poor boy already feeling pre-cum bubbling up to the surface. He couldn't risk having cum stains in his undies when Ms. Buxton checked tomorrow, but he was past the point of no return.

Chris quickly slipped his cock out of the panties and held it tightly, only speeding his orgasm up. He couldn't just cum without looking at something, but he didn't have time to search online. He turned and saw himself in the mirror, his skinny legs in a pair of panties and couldn't hold it anymore. His hand relaxed and his cum shot out, splattering all over the low end of the mirror. Usually Chris was a single roper, but this time four distinct loads came out. Chris collapsed to his knees, surprised with himself.

But his surprise was short lived, as a knock at the door brought him back to realization. "Chris? What are you doing in there that you've got the door locked?" Emma asked.

Chris didn't have time to switch back into his boxers, he grabbed a pair of gym shorts and quickly pulled them over the panties, hoping that his cock wasn't still leaking too badly. He pulled a shirt on over his head to cover and tent action he may have before going and unlocking the door. "Oh, Emma, um, nothing, just, you know, getting dressed" he said, putting his hand behind his head nervously and feeling wet cum from his hand stick to his hair.

"Alright, weirdo. Well, I was in a rush this morning so I forgot to give you your weekly allowance" she said, handing him a twenty dollar bill. "Don't spend it all in one place" she said with a laugh, turning on her heel to head back to her room.

Chris felt a rush of relief that Emma didn't notice anything and closed the door again. He pulled off shorts and felt the panties for a wet spot. It wasn't too bad and he quickly took them off to make sure it didn't get any worse. Putting his own underwear back on before the gym shorts, he wondered how he had gotten into this entire mess all on the first day of school. He grabbed a white t-shirt and cleaned off his mirror, tossing it into his hamper when he had finished getting all of his cum off.

Chris fell into his bed and passed out quickly, tired enough after a very long first day back.

Chapter 2: A New Day

"What are you wearing, sissy? Girls panties? What a fag!" Chris felt the other boys pushing and taunting him. How did they find out? He had been so careful!

Chris sat up from his dream with a start, his body twisted up in his blankets and pillows. It had just been a dream. Well, the being bullied part was at least. The boy fell back against his pillows heavily, putting his hands over his face as the events of yesterday came flooding back to him. He was going to have to wear panties to school today, or he was going to owe his teacher a lot of money that he didn't have.

The door handle rattled and Emma stepped in, wearing PJ pants and a tank top. "Oh you're up already? Good. I'm going to take a shower, get ready for school and make yourself something for breakfast" she said before closing the door behind her. Chris untangled his covers and pulled them off, hopping out of bed in his gym shorts. He walked over to his dresser and saw the pair of purple panties he had stolen from Chelsea on top. Chris sighed, it had all really happened.

Hoping that this would be a short lived punishment, Chris pulled off his shorts and underwear and slipped on the panties. He got the shivers again as the soft fabric touched his sensitive lower area and wondered how he would make it through an entire day like that. Not wanting Emma to catch him in just panties, Chris quickly pulled on his uniform, covering up his little secret.

As Chris left his room, he passed the bathroom and heard the sound of water pouring. He had always wondered what Emma looked like naked and he put his hand on the door knob. Was he really going to do this? He was already going to school in panties, what other weird stuff could he get into? Chris quietly turned the handle and didn't hear Emma scream, so he peeked his head in. He couldn't see her directly, only her blurry outline through the glass shower door, but she was just as stacked as he had always imagined. His heart was beating out of his chest and he got nervous that Emma could hear it. Chris quietly closed the door and continued on down the hallway, quickly heading for the kitchen.

Chris made himself a bowl of cereal and sat down at the kitchen table, happy to be up early enough to eat this morning. Emma came down not long after, he body wrapped in a towel. Chris couldn't help but fill in the blanks about what Emma looked like underneath that towel, and he felt his cock harden in the super soft panties he was wearing. Chris averted his gaze, looking down at his cereal as he ate.

"Did you have a good first day at school? I remember Ms. Buxton can be quite the hard ass" Emma said, having gone to the same school a few years earlier.

"Oh, yeah, she's already on me because I was kinda late yesterday" Chris said nervously. It wasn't really his fault that he was late, Emma hadn't woken him up early enough. But he didn't want to blame it on her either. "But its alright, we're..um...working it out" he said, finishing up his bowl. He picked it up and quickly turned towards the sink, hoping that Emma wouldn't catch any sight of his pants tenting up. "Don't want to be late today, I'll see you later, bye!" he said quickly as he grabbed his bag and rushed out.

Chris passed the jogger again, stepping out of his way as the man couldn't be bothered to move at all. Chris felt a bit weak looking up at the taller man as he passed by. He wondered what a guy with muscles like that would think if he knew that Chris was wearing girl's underwear. Would he treat him like a girl? Chris shook his head, not wanting to go down that line of thinking. It was too weird.

The boy was almost to school, getting used to the feeling of the tight, soft panties on his crotch, when he turned the corner and bumped into his bully, Ryan. "Watch where you're going dweeb, you might just end up on the receiving end of a swirly" the larger boy threatened, stepping towards Chris in a menacing way. All he needed, today of all days, was for Ryan to grab him by the pants. He backed up quickly and was saved by the sound of the bell ringing, beckoning the kids to class.

Chris made it through the day without anyone noticing his secret, even managing to sneak into a bathroom stall during gym class to change. As the end of the day approached he could feel his nerves acting up. It was one thing to wear the panties hidden all day, it was another to actually show it off to his teacher. As the last bell rang, he gathered his things and slow walked to Ms. Buxton's room, half relieved and half annoyed to find he was the only student there.

"Mr. Sellers, good of you to be on time for once" she chided and got up from her desk. Her heels clicked against the tile floor as she walked to the door in a pencil skirt and white blouse. She closed and locked the door before pulling the blinds. Pushing Chris to the corner of the room so no one could see in no matter how hard they tried, Ms. Buxton towered over the small boy. "Let's see it" she said plainly.

Chris' face went bright red. He nervously reached for his belt and undid it, slowly undoing his pants before allowing them to drop to his knees. "What's wrong Chris, feeling ashamed? I want to see you wearing just the panties" Ms. Buxton crossed her arms and began to tap her foot. She was actually serious about this.

"Yes, Ms. Buxton" Chris said weakly as he took off his blazer and shirt and then removed his pants completely. He stood against the wall in front of his teacher, wearing just his best friend's purple panties. His heart was pounding, and it was the absolute worst time but he could feel his cock begin to get hard. Chris lowered his hands to his crotch, hoping to cover it but that just brought Ms. Buxton's attention there.

"Are you...are you getting aroused? You little sissy. This is supposed to be a punishment and you are enjoying it. Put your clothes back on you perv" she commanded, getting out a notepad and writing something down. "I am creditting you with $5 for wearing panties today, but because you are enjoying it we will up the weekly debt to $50. Tomorrow I want you wearing a bra as well, and I want it to be matching." Ms. Buxton marked something off on the notepad and then waved Chris off. "You can leave, same time tomorrow though" she said as she sat back down at her desk.

Chris was relieved to not have to spend the entire time in detention with her, but now she wanted him to wear a bra as well? He put his clothes back on and sheepishly rushed out of the classroom. Should he hit Chelsea back up and try to steal more clothes? She would catch on pretty quickly if he did it too much. He was going to have to buy some and he reached into his pocket, finding the $20 bill that Emma had given him for allowance. It wasn't much, but maybe there would be a clearance rack at the mall.

Chris walked across town to the old mall, the one that wasn't as nice but also wasn't as busy. There weren't many stores there, but they had everything he needed. The people that hung out there were a bit shady, but it was less likely that anyone from school would notice him there. Chris navigated his way around the mall to the women's underwear store, walking around back and forth in front several times before finally walking in. There was a blonde woman behind the counter and no one else in the store, both a blessing and a curse. The clerk immediately honed in on Chris and walked over to help the boy out.

"Hi there, welcome to Intimate Apparel, I'm Sasha. Is there something I can...help you with today?" she asked condescendingly, unsure what the young boy was there for. "Are you looking for something for a girlfriend or a sister?"

Chris didn't know why he didn't think of that before. "Yes! I'm getting something for my sis.....girlfriend. My girlfriend" he switched up, realizing how weird it would be to buy underwear for a sister. "I want to get her a matching bra and panty set, but I only have $20?" He looked around the store, trying his hardest to not look Sasha in the eye. But she could get the picture.

"And what size is your girlfriend?" She asked, betting herself that the boy had no idea how to answer that.

"Oh, she's about...my size?" he said, more like asking.

Sasha got the hint. Every now and then a guy would come in like that, she knew exactly what they were there for. "Well then, at least you can try it on and make sure it fits" she said with a wink, leading Chris to the clearance section. "Here are the things we have on clearance, unfortunately its all mismatched stuff. We could pick through and try to match something you like or..." she trailed off before walking over to the nicer, matched pairs. "...you could try something from here."

The sign stating the price of the underwear was beneath it, and it was twice what he had on him. Chris nervously fidgeted with his money, but Sasha spoke up again. "Its alright if you don't have enough, I'll let you have it if you model it for me."

Chris couldn't believe the offer. He didn't really want to dress up in a bra and panties for a stranger, but if he could save the money he had in his pocket and get the necessary things to not get in trouble with Ms. Buxton, that was a win! "Deal" he said quickly, grabbing the items from her hand before rushing off to the dressing room. He closed himself inside and felt his heart pound. He was just supposed to be in and out, not showing off his secret to more people. But it was just a quick show, and it would save him a bunch of money.

The teenager took off his school uniform and stripped down to his purple panties before slipping on the new black ones. He picked up the bra and...realized he was quite confused. He had seen women put this on before, surely he could figure it out? Chris put his arms through and tried his best to reach back and strap it together, groaning as he did.

There was a knock at the door and Sasha quietly asked "Are you having trouble in there? I can help if you'd like."

Chris stood there in silence for a moment, not sure how to respond. Finally, he click the lock button to unlock and opened the door. Sasha stood in the doorway and Chris looked up at her "I don't know how to do a bra" he said sheepishly, his hands in front of his crotch as he tried to cover himself up as best he could. Sasha smiled and raised her hand, spinning one finger to let Chris know to spin around.

"Its alright, everyone has to learn sometime. Even if they are just buying it for their "girlfriend"" She said, emphasizing the last word. Sasha stood behind Chris and undid the straps from his arms. "Now, every woman cheats at first. Just spin this around" she said, pulling the back of the bra to Chris' chest, "do it in front of your body, and voila." Sasha hooked the bra in front of Chris and then spun it around again so it was the correct way. "Then, just put your arms in. There, not so hard!"

Chris felt like he could melt into the stranger's arms, the way she gently touched him as she taught him how to put on a bra. "Thank you so much, I'm so glad to finally learn how to put one on..." he said, forgetting himself for a moment before adding "...you know, for my girlfriend"

Sasha giggled and turned him back around so she could get a good look. Chris was already pitching a tent in his new panties and there was no way for him to hide it from her when they were this close. "Well, you certainly have a lucky "girlfriend". If she ever needs more underwear, I'll give you a good discount. As long as you model it for me." The woman cupped Chris' chin and his face felt so hot. This was the most intimate thing he had ever done.

Sasha left the dressing room for Chris to get dressed again. He thought about putting his purple panties back on, but he also wanted to try out his new bra and see how it felt. He put his uniform back on over the underwear and walked out of the dressing room as Sasha smiled at him. "Wearing it home?" she teased and Chris' face got extra red. He rushed off, trying to put as much distance between him and the store as he could.

Chris walked home from the mall, slightly enjoying the new feel of the soft bra pads rubbing against his nipples. He became extremely self conscious, wondering if anyone could tell that he was wearing a bra. Every person he walked past he wondered if they knew. Was it going to be like this every day? Worrying if someone might find out? He shook his head, surely this was just going to be temporary.

Chapter 3: Chapter 3, Confidant

"You can have anything you want in here, as long as you model it for me" she said, her hands running through a tall pile of panties. Chris stepped up to them, his eyes wide as he didn't know where to start. And then he was falling, falling into the pile of panties with no end...

After another night of interesting dreams, Chris woke up to Emma's gentle nudging intensely frustrated. He could feel the wet spot on his PJ's and awkwardly waited for Emma to leave the room for him to finally get up. How was this even real, he wondered to himself, stuff like this doesn't just happen in real life. He wished that he had someone to talk to, someone to be able to tell what he was going through, but how could he even begin to talk about this?

When Chris heard the shower turn on, he knew the coast was clear. He pulled out the bag from Intimate Apparel and changed into his new black panties. They were the correct size and he was ashamed to say he actually sort of enjoyed them. He remembered Sasha's bra lesson and put the bra on backwards, hooking it in front of himself before spinning it around. He looked at himself in the mirror, seeing the same boy he saw the other day, this one was just wearing girl's underwear. Part of him felt a pang of regret that he wasn't more girly, but he shook his head and pushed the thought away.

Chris got dressed and went down to the kitchen to eat breakfast. He microwaved some pop tarts and sat down to eat them as Emma joined him from the shower. Chris had forgotten to adjust his bra before putting his clothes on and he scratched at his chest to try to correct it as he ate. "Whats up Chris, if I didn't know any better I'd say you were wearing a bra" Emma said with a laugh.

Chris' eyes went wide and he turned away. "Oh, you know, I um...scratched myself accidentally and it itches" he said unconvincingly. He pulled his hand to his chest again and pretended to scratch, trying to sell the story.

"Whatever weirdo, how are classes? Getting along with Ms. Buxton yet?"

He shook his head a little and looked down. "I wish, she really has it out for me. But, she'll get bored, right?" he asked, hoping for reassurance.

"I don't know, she failed a kid in my grade on the last day for a prank he pulled on the first day. They say elephants never forget, Buxton never forgives" Emma said with a laugh as she got up from the table to make herself breakfast.

Chris gulped loudly, nearly choking on his piece of pop tart. He stifled back a few coughs, chugging some water so he could breathe again. Emma looked at him quizzically, and he managed out a weak "wrong pipe". The nervous boy got up from the table and grabbed his bag, wanting to get to school early now in hopes that being a model student might get him on Ms. Buxton's good side again. Rushing off to school, he forgot to say goodbye to Emma as he left.

The teenager power walked to school, adjusting his bra the entire way. He didn't have anything for it to hold onto, so it just kept moving! If only he had some tits it would be easier, he thought to himself, stopping in his tracks and shaking the thought from his head. Why did he keep thinking these things?!

He got so bothered by his bra that he accidentally ran into the jogger. Thankfully the larger man had been watching where he was going and grabbed the boy before he could fall over "Watch where you're going kid!" the guy said before continuing to jog on his way. Chris stood in a trance, there was a moment that he actually enjoyed the strangers strong arms around him. What was happening?

Chris got through the rest of the day without any major issues, except for the bra bothering him. When he made it to detention, he was almost glad to show it to Ms. Buxton because at least he could ask her about how to wear it correctly.

"You went and bought a bra without making sure it was the correct size and that it fit well? You're going to need someone who knows what they're doing a bit better than you, and I cannot hold your hand through this. So today, here is your assignment. I want you to find a confidant. A girl you can confide in about your taboo tendencies and who can help walk you along the path. Do you have someone like that?" Ms. Buxton asked.

Chris thought about Emma. She was always around, she was kind of motherly to him, but she also could be kind of mean and she also knew his actual mother. If she didn't like it then this would go straight back to her. Then he thought about Chelsea. She had always been there for him, and she didn't go to the same school or anything. If there was anyone he could tell this to, it was Chelsea. Chris nodded at Ms. Buxton, "I think I know someone I can talk to about it."

"Good, I want you to talk to her and tell her you've been thinking a lot about wearing women's clothes recently. You are not to tell her that this is a punishment from school. Ask her to help you with picking out the correct size bra and panties and see if you can borrow a pair or two. After all, you don't want to wear these every day of the week now, do you?" She waved Chris off, dismissing him from detention.

He walked to the front of the school, nervously texting Chelsea. "Hey Chels, I really liked hanging out the other day and I have something I need to talk to you about. Do you have time today?"

It didn't take long for Chelsea to text him back. "Of course Chris, you know you can talk to me about anything. Come on over?"

Feeling reassured, Chris made his way over to Chelsea's house, wondering just what he was going to say to her. "Hey Chels, I like wearing girl's clothes, can you help me out and lend me some stuff?" he practiced as he walked. That wasn't going to work, it was going to have to be real. But how could it be real if he didn't really want this?

By the time he reached Chelsea's fancy steps, he was no closer to coming up with what to say as he was when he started walking. The door opened and Chelsea stood before him, looking concerned. She wore a long hoody, her shorts beneath barely visible at the top of her long legs. Chris bit his lip, why did she have to be so attractive? That just made it harder.

"Hey Chris, come on in. You wanted to talk?" she asked in a concerned voice. "Why don't you go up to my room and I'll grab snacks."

Chris nodded, glad to have a little extra time to come up with what to say. He took his shoes off and looked for the stairs, heading up to Chelsea's room. Walking into her room, he felt bad about having stolen a pair of panties from her. He wondered if he should start with coming clean about that, but he was interrupted by Chelsea entering the room sooner than he expected.

"I figured today was an ice cream kind of day. And I brought sodas if you want to make floats" she said, holding up the silver tray before setting it down on her coffee table before sitting down. "What's on your mind, bestie?" she asked while grabbing a spoon and taking a scoop of Rocky Road.

Chris sat down across from her and looked at the ice cream. He wanted to stuff his face so he didn't have to talk but the longer he waited, the more embarrassing it was. He clasped his hands, feeling his face get hot. "Well, so um...there are some things...about me that I want to tell you" he searched for the words, grasping for straws as they spilled from his mouth. "You see I...have been experimenting lately." His face turned bright red with the use of that word. There were so many things it could mean, he could already see the wheels turning in Chelsea's head. "NOT LIKE THAT! I mean. Um...I've been, trying women's clothing on, like, underwear and stuff." Chris could no longer look Chelsea in the eye and looked down at his folded hands instead. "You probably think I'm weird and don't want to see me anymore."

The silence felt like it dragged on for an eternity. Chris wished that he could just leave his body and transport halfway across the planet. But then, Chelsea spoke. "Are you wearing it now?" Was all she said.

Chris felt a lump in his throat keeping him from saying anything else and nodded his head instead.

"Can you...will you show me?" she asked, sounding somewhat interested.

He stood up and took off his blazer, his heart pounding out of his chest as he began to undo his tie and open his buttons. Chelsea let out a light gasp and Chris felt his nerves tense up again "You're wearing a bra too?" Chelsea asked gently as the boy continued to undress.

"I...wanted the entire experience" he squeaked out, unable to tell Chelsea that his teacher was making him do this. The fact that she hadn't run from the room was a good sign, but perhaps she was just waiting for the entire picture so she would have more to make fun of him over. He removed his belt and slid off his pants, standing in front of his best friend in a black pair of women's underwear. His life hadn't been anything amazing before, but this felt like the low point. "Its okay, you can laugh" he whispered.

Chelsea got up and stood in front of him, taking his hands. "The only thing I'm going to laugh at is your sense of style, where did you even get this underwear?" she asked. The feeling of her hands on his was reassuring, he had practically been on the verge of crying as he undressed.

"You, don't think its weird or that I'm a loser?" he stifled a whimper.

"Of course not. We're friends! I would never shame you for being who you are, and I'm so glad you shared this with me!" She wrapped her arms around him and he felt like he was going to melt into her, the soft fabric of her sweatshirt enveloping him. Unfortunately, the enjoyable feeling got his blood flowing and Chris pulled back before he had any extra issues.

"Thanks. I really need a friend" he said, sitting back down as he felt extremely exposed in his current state. "I, um, don't know what size I am and this bra has been scratching the hell out of me" he said in quite the honest manner.

Chelsea giggled, understanding the issue all too well. "I'm so glad you could come to me with this. And I think I have a perfect solution. Come on." She reached over and took Chris' hand, yanking him from the couch before pulling him across the room.

"Where are we going?" Chris gasped, feeling nervous as he felt vulnerable in his current state. "Chels, come on I'm pretty nervous!" he said timidly. He hadn't seen or heard anyone else in the house, but that didn't stop him from imagining the place full of her family. Chelsea pulled Chris into the hallway and to the next door, opening up her little sister's room. She didn't say a word until she pulled him to the younger girl's closet and opened it.

"We aren't the same size, I'm a little taller, but my sister's clothes should fit you perfectly! Karly is in France for the year so she won't notice anyway." Chris followed Chelsea into the closet, again marveling at the amount of clothes that she had. He couldn't admit that he had been in Chelsea's closet, so he feigned surprise at the size.

"I've never seen a closet this big! All of these clothes here and she has even more in France?" he asked, amazed at how rich some people truly were.

"Yep! So you can try on anything in here, maybe even take it home, as long as you don't get it dirty or messy of course. Does that sound good?" she asked. Chris could hardly answer, he didn't expect for Chels to be so cool about everything, much less for her to offer up an entire wardrobe. But at the same time, he didn't want to wear women's clothes. He was only doing this because Ms. Buxton was making him.

"T-thank you! That is so nice of you Chels, but for now I just want to try...you know, underwear" he said nervously. He realized that that sounded a bit...pervy and quickly thought of a way to explain it away. "I'm not ready for...a full outfit" he blurted out, scanning Chelsea's expression and hoping he had saved himself.

"That's entirely understandable. I don't want to push you any further than you're ready for" she reassured, turning towards the closet and looking for her sister's dresser. "Alright, so underwear then. How about I get a few things for you to choose from, you can sit on Karly's bed."

Chris nodded and left the closet, feeling his heart beat start to slow down. This was going perfectly, he was going to be able to satisfy Ms. Buxton and he wasn't going to lose a friend. This wasn't the worst thing, Chelsea actually seemed interested in what was going on. Maybe if he was lucky, this could be his in. But what if she saw him as too beta, or maybe like a little sister?

Before Chris could continue that thought, Chelsea returned with an armful of underwear. "Alright, now I don't know what kind of style you're interested in so I got you a few different kinds." She put down the pile and picked up a thong style, holding it against Chris' crotch to see how it looked. "Oh...um, but one thing? Do you think we could do something about your leg hair first?"

Chris' heart skipped a beat. Do something about his leg hair? "Like, shave it?" he asked sheepishly.

Chelsea laughed lightly "Shaving takes forever, I think waxing works best but if you're new to it it can be a bit much. I do have a hair removal cream that works pretty well. Come on" she said, pulling Chris into Karly's bathroom. "Take off your underwear and put on a towel, wouldn't want to get your clothes messy. I'll go grab it and be right back."

Chris watched as Chels left the bathroom. She had just told him to take his underwear off, just like that. It wasn't exactly how he imagined getting closer to her, but he would take any chance he got. He pulled off his panties and wrapped a towel low around his waist. He looked at himself in the mirror and felt weird still wearing a bra, so he removed that as well.

When Chels walked back in she giggled at Chris' now naked body. "Still thinking like a boy!" She put down the large bottle of hair removal cream and walked around behind Chris. Wrapping her arms around him, she undid his towel. Chris felt extremely nervous as it was removed and tried to cover himself up, only for Chelsea to pull the towel up around his body. She wrapped it tight under his arm pits, the bottom of the towel barely covering his ass and crotch. "I have to get at your legs silly" she said playfully from behind. "Go ahead and sit down" she said, pointing at a small bench next to the bath tub.

Chris held onto the towel tight, unsure of this new way of wearing it and sat on the bench. He could feel air on his package and nervously crossed his legs, crushing himself a little but also succeeding in hiding his dangly bits. Chelsea looked through Karly's cabinets for latex gloves, not wanting to get any of the removal cream on herself. After finding a pair, she put them on and began squirting the cream into her hands. "Now its going to start off feeling cold, but it will get warm fast. If it starts to burn it means that the hair is ready to wipe right off." Chris was nervous but extended a leg, doing his best to keep himself covered.

Chelsea started at the ankle and began rubbing the cream on. Chris wasn't especially hairy, but the smoother the better. His legs quickly went from pale to white, the heavy cream covering him completely. Chris shivered at the feeling of Chels' hands moving over his skin, although part of that was how cold the cream was. When her hand rounded Chris' knee, it was an entirely different sensation. It was like there was a direct connection between the nerves in his thigh and the nerves in his cock as every touch sent electricity up his loins.

"I need your entire leg silly, go ahead and uncross them. Its alright" she reassured him. The cream at his ankles was already starting to warm up and Chels' hands kept moving higher. He couldn't help but feel the rush of blood to his crotch and soon there was a small tent in his towel. Chris hoped that Chels wouldn't notice but it didn't take her long as she was working quite close on his thigh. "Oh, um, that's alright! Its totally normal and all, I guess I am touching you...pretty close to there." Her tone was apologetic, she didn't seem mad at him, but she didn't seem happy with it either. "I just need to get...all the way, you know, up."

Chris wanted to bury his face in his hands but he didn't want her to stop touching him. "I'm so sorry" he whispered but Chelsea waved him off. She really meant what she said about all the way up and soon Chris felt her hands on his crotch, rubbing the cream over his balls and the bottom of the shaft of his cock. She was only there for a moment but Chris got fully hard in that time.

"OK, now turn around!" Chelsea commanded, quickly getting away from Chris' hard on and moving to his backside. She pulled his towel up to reveal his butt and began to spread the cream on there as well. "There, luckily you don't have any chest or back hair or we'd have to cover you completely!" Chelsea teased and poked Chris in his sides, causing him to nearly fall over.

"Hey! Don't tickle me, I'm naked!" he whined, feeling exposed.

Chelsea gave Chris a strong pat on the ass "You big baby, I just helped you shave your legs, you can handle a little tickling. Is the cream starting to burn yet?" she asked, taking off her gloves and tossing them in the trash.

Chris' lower legs were starting to get toasty, but his ass and crotch felt like they were on fire. He didn't want to admit to that so he just shook his head. "Just a little warm" he said, trying to put on a brave face. Chelsea opened the shower door and turned the water on, letting it warm up for Chris.

"Alright, well hop in the shower when it gets to be too much. So, what made you...you know, decide to wear girl's clothes?" she asked, sitting across from him while watching him semi-adoringly.

Chris didn't know what to say. He couldn't say that it wasn't his idea. "I just...always was interested I guess. I...used to steal undies from Emma" He said, his face turning bright red at the admission. He didn't want to dig himself a hole any deeper, so he quickly changed the subject "The cream is starting to burn so I'm going to hop in now."

The shower brought relief in more ways than one, getting him out of the sticky conversation and alleviating the burning feeling from the cream. He reached down and rubbed the cream off, watching as his hair fell away with it. Chris moved fully underneath the stream and let the water wash over him. He wanted to stay there forever, but he knew Chelsea was waiting for him on the other side of the shower door. He picked up the bar of soap and washed himself down, finally getting a view of his perfectly smooth skin. Even his pubic hair was gone, his cock going back to looking like it had before his balls dropped.

"You almost done in there? Come on, just wait until you feel smooth skin against panties!" Chelsea exclaimed from outside. Chris was torn. He was only doing this because he had to! But the sound of smooth skin on panties...He finished washing off and turned off the shower. He opened the door and reached his hand out for Chelsea to hand him a towel, but instead she pulled him out of the shower. She held the towel out around him like she had done before, giving him a helping hand. "Once you're dry you're in for a treat."

Chris followed Chelsea out of the bathroom and back into Karly's room, back to the pile of underwear. "Alright, we're going to start you off with the basics. Cotton panties" Chelsea said as she held up a plain white panty with a matching bra. It was devoid of designs or frills, but it still felt so.... Chris took the panties and lowered them between his legs, stepping inside and pulling them up tightly against his rear. The fabric against his now smooth skin was something to behold and he had to hold back his enjoyment. "Pretty great, right?" Chelsea asked, holding up the bra for him as well.

Chris nervously dropped his towel, knowing he couldn't put the bra on over it. Taking it from Chelsea's hand, he was surprised this one didn't have hooks. "It just goes on over your head. You don't really have anything, you know, up top, that needs support. But at least this way you can get the look." Chris blushed at the words. He didn't want "the look", he just had to wear the clothes.

"Alright, next look!" Chelsea said, picking up a pair of pink boy-shorts that said "Juicy" on the butt cheeks and a matching pink bra. "This one has hooks, but I'll show you the easy way to put it on to make sure it isn't bothersome." Chelsea handed the underwear to Chris and stood there, waiting. She wasn't going to leave the room for him to change, so Chris turned away for a little privacy. He pulled the white panties off first and replaced them with the pink ones, feeling his butt jiggle as the supportive underwear shaped his entire rear.

Chris removed the white bra but before he could turn to ask for the pink one, he felt Chelsea's arms wrap around him. "See you put the hook in front of you, like this, and it goes in easy. Then you spin it around and put your arms through." Chris had already gotten this lesson from the clerk at Intimate Apparel, but he enjoyed it more as Chelsea helped him. "Then you've gotta lean over and adjust yourself into it".

Chelsea's hand pressed against Chris' spine and gently bent him. "See, gravity will help you and then you just reach like this..." she pressed her hand against his chest and pulled on his skin, settling whatever pectoral Chris had into the correct spot of the bra. "There isn't that better?" she asked, lowering her hands to his hips as she stood behind him.

He could hardly control himself anymore as Chelsea pressed against him from behind. His cock began to harden but he didn't care anymore, he just wanted to be there with Chelsea. Unfortunately for him, she noticed his growing tent. "Yeah, so thats a few kinds of undies. Actually, I think my house cleaners are going to be here soon. You've gotta get dressed and go" she said quickly, her demeanor changing from loving to cold.

Chris didn't want to push his luck, but he needed some more underwear. "Is it alright if I ...take these?" Chris asked, motioning at the set he was wearing.

Chelsea picked up the pile of undies and shoved them into Chris' hands "Sure, just hurry up before anyone gets home. Come on!" she hurried him, pushing him back towards her room. Chris grabbed his uniform and dressed as quickly as he could. He stuffed the panties and bras into his backpack, trying to grab as many as he could like this was a cash cube machine.

"Thanks Chels, thanks for everything" he huffed out as he got all of his things together and rushed to the door.

"Don't mention it, maybe next time you'll let me dress you up in something cute and uh, covering" she said before practically pushing him out of the door.

Chris hoisted his now stuffed backpack over his shoulder, still in a daze about what had happened. The feel of Karly's panties on his smooth skin was hard to get out of his head, and even the feel of his pants was different. He couldn't believe that Chelsea had touched him...down there, but she didn't seem that into it. As a matter of fact, she seemed more interested in him being girly and seemed to get turned off of it when she was reminded that he was a boy. Did...Chelsea like girls? Chris was left to wonder as he walked home, but he had an even bigger question.

How was he supposed to hide all of these clothes from Emma?!