Teacher to Student

Note: This is my story Math Teacher to Student that I once posted the first few chapters of, you will notice it has been reworked. It was co-authored by myself and H. Ham. You can see their caption work over at https://www.deviantart.com/honeyfham

Chapter 1The hotel room’s door reverberated as someone's knuckles connected over and over again. The knocking sounded like a construction crew's jackhammer. Gabe really didn't want to get out of bed, it was comfortable, it was warm and cozy in the cold hotel room. At first he moved the pillow over his face. Hoping whoever it was would just go away, but it persisted. With frustration, anger and a massive headache he trudged to the door, pulling it fully open to give the moron on the other end a piece of his mind.

On the other side of the door Gabriel found his older sister, his senior by seven years. He wasn’t feeling the greatest and the way she looked down at him with her judging eyes didn’t make him feel any better. The fact that she always looked down at him, her standing at five foot eight, before you considered the heels she often wore, to his five foot five never sat well with Gabe.

Gabe’s sister, Maria, looked well put together as she always did when leaving the house. A maroon blouse, black long pencil skirt, dark hose on her legs and pumps. Her hair and makeup was immaculate. A big difference between his current disheveled appearance.

"I brought you coffee, here." Maria said, handing over a paper cup from Dunkin before she walked past him into the room. She could clearly see that her brother was not happy to see her. Maria wasn’t even sure why he agreed to be a chaperone for the school trip. Her brother wasn’t involved with the Future Business leaders of America school group and from what she could see didn’t even like his own students.

Looking away from her brother and over to the hotel room with a double bed and then back to Gabriel. She wrinkled her nose, assessing him and the smell, the stink of **** coming off him like a cloud. Her sibling was standing there in a pair of boxers, a light gray button up shirt that was half undone, covered in dark stains and wrinkled like he slept in it. His dark trousers and jacket were nowhere to be seen, but his shoes were scattered at the foot of the bed.

"You look and smell awful. When was the last time you bathed and…" She waved her hand in front of her face to clear the air of his smell, her long painted nails glinting from the overhead light as she did.

Before she could lay into him Gabe locked eyes with his sister and slammed the door closed. An action he wished he hadn't done as the headache flared in sudden pain making him lose that staring contest right away. "Gah! Damn my head!”

Trying to shake it off, he plopped back down on the bed he had slept in and held his head in one hand. "I don't need to hear anything from you! I'm a grown man and can do what I want in my free time." He looked at the cup of liquid energy in his hand and took a sip, enjoying the flavor as it gave its unspoken promise to invigorate him. "Also thank you for the coffee."

Friction between the two siblings had always been there. Gabriel was the baby of the family. Between that and their mother feeling guilty for both not being around enough so that she could work and still not having enough to fully provide when she had another mouth to feed, she let her little boy get away with just about everything. With their mother off working as a maid for wealthy folks, Maria had been left in charge. Something young Gabe rebelled against. Once he moved home after college the two had slipped back into old habits.

Smoothing her dress as she sat down on the clean bed, Maria bit her tongue, not wanting to get him riled up at the start of the trip. "You are welcome, so I take it you went out and had fun with your friend.” She gave a slight nod of her head in Gabe’s direction to indicate his current state. “How was your interview at Sidwell?" The private school here in DC was said to have a tuition cost of around forty five thousand dollars and she hoped that if her brother got the job he would actually find joy in his career. Considering Gabriel’s expression she figured it went poorly.

Sitting there he let the silence between them grow long enough to be uncomfortable. Letting out a long sigh he shifted his head to cover his face for a few seconds. When his sister stood there still waiting for her answer he looked back up to her. "I didn't make it."

Maria tilted her head and leaned slightly closer without shifting her body any closer to her obviously hungover brother. "What was that?"

Gabe closed his eyes, wishing he didn't have to have this conversation, wishing the events played out differently. "I didn't make it to the interview." He said looking up at her as his face left his hand. "Clint and I stayed out pretty late, and then I woke up late. Got my suit on and rushed to get there, but it didn't matter. When you are over an hour late for an interview, you would be lucky to get seen, and I wasn't lucky."

Narrowing her eyes at her brother, Maria was shocked. He went on and on about how this job was going to get him out of the state and make the money he deserved. Then he went and pissed it away because he drank. She took a second to consider his appearance again, deciding he had done so yesterday as well. "Tonto.” The thirty one year old woman said to her brother, calling him stupid with a great deal of exasperation in her voice. "Why didn't you just call them to say you were running late?"

Taking another sip of the coffee Gabe took a second to savor one of the only good things to happen, that drink. "When I said I wasn't lucky, I actually meant I have had a lot of bad luck. The day I arrived Clint took us out and we met up with some girls." Maria held up a finger for him to stop.

"Wait, didn't you mention that your friend was married, or was that a different friend?" Gabe shrugged like it didn't matter.

"That is him, but his home life is his business. Well as the night went on I was telling Jasmine."

Maria interrupted him again. "Who is Jasmine?"

Gabe glared at her and let out a huff before continuing. "A girl we met there, stop interrupting. I was telling her about my new phone and she took it from me, to play with and well, she umm she put it in a glass of water as she said something along the lines of “Oh this is that one that is waterproof.” Thing is…no phone is waterproof, she was just as air headed as some of my students, and she destroyed my phone. No phone, no alarm, no way to look up my contact to call." Gabe held his arms out as he shrugged in a what are you going to do motion.

The corner of his lips turned up slightly at the memory of Jasmine, her blonde hair cut in a bob, her red dress that showed off her tits nicely and some gold necklaces that helped pull the eye to her fantastic assets. She was dumb as can be, but the fact that she bought him a drink gave him a hand job under the bar counter… well one through his pants, but still, it had not been the worst encounter of his life.

Looking at her brother like he was an idiot, Maria rolled her eyes. "The hotel can call the room to wake you up, and I guess you went out drinking again after that by the way your shirt looks."

Gabe opened his mouth and closed it, then bit into his index finger as he thought. "Yeah, drunk me didn't consider that option, and yes I did. Clint did not, he was a little upset about me not making it to the interview. Saying it made his wife look bad, and he didn't care for my retort of him having a tongue down the throat of another woman that didn’t much look like his wife. Think I burned that bridge, see like I said. Bad luck this entire trip."

He glanced towards the door and smirked back to his sister at her having some of the same luck. "Looks like the airline lost your bag too." Maria thought about that for a second, she hadn't noticed his suitcase when she came in. "No, the bellhop is bringing everyone's bags up all at once. I figured I would come up and talk with you before Sam, sorry Mr. Banks got to see you, and wow it is a good thing I did. You are a mess, change into whatever you wore when you arrived because that shirt needs to be thrown out and… take a shower please."

Her telling him what to do and having completely forgotten about meeting his new boss, a new boss who couldn't be happy with him taking a few days off and meeting them in DC instead of helping corral the kids on the flight. He felt like he needed to explain himself, and being aggravated that she always made him feel that way. “I was hoping to win points by watching over the kids with Banks, maybe have a drink at the bar with him when they were down for the night.”

Gabriel shifted on the bed, his head still pounding. “Thing is… Ah yeah, about what I wore when I arrived. I gave my clothes to the maid or something late last night, literally gave her the pants I was wearing and asked to have them washed.” Gabe shook his head, biting his bottom lip in frustration. “She argued with me about it being too late for a pickup, but she took them all the same when I was done. So I can take a shower but I need to call down about my clothes. Oh but don't worry, I got vouchers for three hundred dollars at the local mall so I can just run out real fast while everyone gets situated, well once they give me my clothes back."

“Why do you have vouchers…” Maria rightly closed her eyes for a second. "Por el amor de Dios..." She said as she stood up, calling for the love of God at the same time using it as an insult to the idiotic plans her brother was making. “You lost your bags at the airport and then you lost your pants at the hotel?”

Waving his hand in the air as Gabe was trying to dismiss his sister, wishing she wouldn’t be so loud. "Yeah, yeah, I get it. You don't have to talk to me like I'm a kid, you are not my fucking mother. And I didn’t lose anything. Between GIVING my clothes to the bitchy maid here to launder…” Gabe pressed his hand firmer to his head, regretting raising his voice. He had already told her where his pants were, but she seemed more interested in talking down to him, than actually listening.

“The bitch here and bitch at the airport… no let me tell you about this little brain dead girl at the airport. Dark skinned Indian girl… Dot, not feather, you know. She had her hair bleached so much it was white and it must have seeped into her brain because she couldn’t be bothered to even make a phone call about my lost bag. She pretended to click on her keyboard before telling me she couldn’t find it in the system, but she did it in like three seconds. You know, the thing one might do when pretending to actually work instead of working." Maria recalled how he’d do the same thing when asked to file paperwork at the school.

Rubbing the palms of his hands on his hairy legs, Gabe could feel his frustration turning into anger at the memory. “I was letting her know exactly what I thought of her work ethic.” Gabe remembered standing in front of the counter, slamming his fist down as he raised his voice.

“Then, her manager stepped in to actually get something done, not sure why the airline would hire someone like that… but with my luck it was people like her that lost my bag to begin with.” He paused in his rant, closing his eyes, feeling the throbbing in his head. “I don’t mean her race, I just mean brain dead.” Gabe didn’t think his sister would suddenly start thinking he was a racist, but the whole world was just too damn PC.

“Anyways the manager said he would personally call if the bag showed up and then…” He waved his hand in the air. “The voucher thing, he was going to only give me one hundred and fifty, but if I signed some form about liability he would bump it up to three hundred. That is what happened, don’t you be getting all bitchy on me too, I have had enough of that.”

Standing up from the bed, and turning on her heel, Maria pointed her French nail tipped finger at him. "Don't you start, just get this taken care of and I will tell Sam that I haven't seen you yet if he asks."

Gabe gave her a mocking smile and picked up the hotel's phone. "Yes Mami." He said mockingly to give her a verbal poke that seemed to work enough for her to glare at him like she was going to kill him.

Before she could say a word he was connected to the front desk with a shit eating grin on his face as he held the phone to his ear. "Yes, I wanted to tell you my room is ready to have its laundry returned."

Maria wished he was a child so she could spank some manners into him. Growing up their Madre was so much stricter with her, saying it was her job to do the laundry, her job to clean the house. It was Gabriel’s job to take out the trash, and take care of the lawn, but she also had to look her best and have an earlier curfew, because she was a girl.

Old world mentality that she carried on, she loved her madre so much. She was strong and one of the hardest working people she knew, working for low wages and never being upset at the rich folk that treated her like dirt, all because one of them, just once gave her a large amount of money, but that was from their kid, Adam Wesker or something and only after they had fired her for making friends with him.

She gave Gabriel extra privileges because he was a boy, and extra attention due to guilt. When she was between jobs when they were younger he had become malnourished and even now as an adult the effects were clear with his height and small build, but still some swats with the wooden spoon might have kept his attitude from escalating to this point. Thoughts of growing up faded as she saw that stupid grin of his fade as he hung up the phone.

"The uh, maid I spoke to last night. She quit and they don't know where she placed my clothes. They are going to look and apologize. Saying they will call her to find out, but when she quit she said she was done dealing with entitled guests… I think they won't find my clothes unless they look in the trash. I thought she got it through her head that it was important that my clothes were taken care of and she smiled saying she would do just that." Gabe bit down on his index finder for a second as he stood there in silence with his sister trying to figure out what to do. "Joder, esto es malo" he decried how fucking bad things were.

Maria watched as he panicked moving about the room saying "¡Mierda!" or "¡Joder!" just yelling fuck and shit over and over again in a type of temper tantrum. She shook her head considering the problem. He could be bad under pressure at times and it looked like this was one of those times.

An idea struck her, one to bring him down a peg or two and solve the problem at hand. "I have an idea." She said, but he didn't seem to be listening as he paced. "Gabe, I know how to fix this." He kept moving about, without so much as looking in her direction dismissed her.

"Shhh I'm thinking." Gabriel waved his hand in the air, not listening to whatever she was saying.

Channeling the best imitation of her mother she could. The same kind of look their mother would give her when she dared to talk back. "¡Gabriel, detén eso ahora y escucha!" Maria used his proper name, telling to stop and listen and was happy it had snapped him out of his panic enough to actually stop and look in her direction.

"What?!" He snapped at her, baffled that she would demand his attention and then not explain herself.

With a large smile the dark haired woman patted her brother on the shoulder as she moved to the door. "You know what, you just go take a shower. A nice long one, you need it and I will get you some clothes."

“Sure.” Gabriel said without bothering to hide his annoyance. ‘A long hot shower… finally something good.’ he thought, not having the mental capacity at the moment to remember the hot coffee he had been so happy to get a few moments before. "That's great, I was afraid I would have to hide out here and tell Mr. Banks I got sick and couldn't make it, after I was already supposed to be here.” Taking a few steps in the direction of the hotel’s bathroom he turned to face his sister. “Oh, can you get me some more of those tiny shampoo bottles? I used all the little ones they gave out."

Maria nodded and left the room, planning to get him shampoo just not what he wanted. ‘Let us see how you look using my shampoo oh brother of mine. I’m betting it will be that much more embarrassing when you combine it with the clothes I’m going to round up for you. Volverse loca.’ She thought, using the Spanish phrase for going crazy, knowing exactly what would happen when he saw she borrowed clothes from some of the female students on the trip.

The body wash Maria had given him was obviously hers, he had seen it a thousand times at home. Lustrous Glow, scented with vanilla and rose made to exfoliate for healthy skin. The shampoo wasn't much better, Herbal Essence Totally Twisted for wavy and curly hair and it smelled like berries. His hair did have that same natural wave like his sisters, but it wasn’t something he cultivated like her.

Of course, he didn't normally let his hair get long like hers either. Right now though he had let it grow out to get below his ears. It wasn’t like he was intending to grow it out, but that is what happened when you were slumming it and didn’t care much about getting it cut. In his daily life, he used product to keep it styled and up and right now that wasn’t much of an option.

Unbuttoning his gray long sleeve dress shirt, Gabe scratched his chest, feeling more than a little rough, he rolled his head to try and crack his neck, looking at himself in the mirror. His hair was a mess, but the product in it had kept his longer hair up out of the way and his Clark Gable style mustache that was a pain to grow looked fine.

In the shower the hot water felt amazing on his skin, the water pressure was so much better than back home. It made him consider giving his madre an upgrade when he got a better paying job. ‘Fix the water pressure and a nice tankless heater so she could save money, she would love that.’ As the hot water ran down his body, easing the tension he held in his shoulders he leaned forward putting his forehead on the cool tiled wall. "Tan estúpido, ¿por qué hice eso?" Gabriel called himself stupid, asking himself why he did what he did.

He thought back to the first night here, Clint took him out from one bar to the next. Meeting up with some girls he knew at the second. It wasn't till the third bar when all of them were wasted, when Jasmine destroyed his phone. She bought him a drink to make up for it, like it could have.

Though it seemed like everything was fine at the time when she pressed up to him, pulling his face into her large tits. Things only got better when the drink came and she started to give him a hand job through his pants under the table. She had him so worked up as she murmured in his ear. "Cum for me baby, I can feel how hard you are for me. Just imagine me straddling you later in your room. You can cum all over me, yeah that's it baby." He couldn’t remember exactly what she had said, but his imagination was happy to fill in the gaps, adding sexy words to what he felt.

It was incredible and so hot, but the promise of later never happened. He was almost positive she had actually said that and he hadn’t added it, but honestly Gabe didn't remember getting back to the hotel, so wondering why he didn't ask the hotel to wake him up was moot. It was like time traveling, one moment you are clinking glasses together and drinking and the next waking up, covered in your own filth and already late for an important meeting that could have changed his life. He missed it and all because he was trying to be Keg. Trying to keep up with his friend and stay close to the long legged girl he wouldn't ever see again. "¡Joder, joder, joder!" Unable to keep it pushed down Gabriel started to yell fuck, over and over again.

He needed to get out of the shower and see about the clothes Maria left for him, so he could get to the mall and back as quickly as he could. He needed to try and salvage this trip and step up or Mr Banks could turn into another Harry Bisc for him. He needed that like a hole in the head.

After getting out of the shower he dried off, the muggy air from the shower mixing with the cool air of the hotel room, all of it running over his body in an odd way. His clothes were gone and no new ones were left out. Not wanting to be nude in the same room as his sister he poked his head out of the steam filled room. "Maria, clothes?" He heard some movement in the room, but didn't see her. "María, ¡date prisa con la ropa!" When Maria didn’t answer him the first time he told her to hurry up with them. When she appeared he took the single piece of clothing she offered. Closing the door he looked at it and sneered, before turning around and opening the door again. "¿Qué demonios es esto?" He yelled out into the room, asking her what the hell she had given him.

"Panties, you my dear little brother have been a pain in the ass. Not much fits you and you will have to just deal with any embarrassment that you have more than earned when you go get new clothes. Unless you want me to invite Mr. Banks to meet his chaperone for the kids, that isn’t even so much as wearing a towel."

Gabe ground his teeth, trying to hide behind the door even more.. "¡Tu Perra!" When he called her a bitch he got no reply, so he shut the bathroom door, looking down at the white panties with a little pink bow on the waistband’s front. The airport lost his suitcase, the hotel and that stupid cow of a girl lost more of his clothes and now his sister took the last shreds. It wasn't like he had never worn panties before, he hated that he had to wear the less than masculine clothes that could be handed down to him growing up. He hated being poor and vowed to get rich one day, but his Madre was only going to pay for school if he gave back to the country that gave her a new home. So he figured he would be a professor and write a few books. Oh how life changed, him a high school math teacher at public school, about to put on girls’ panties.

Clutching the small piece of cloth in his hands hard enough for his knuckles to turn white, Gabe vowed to get his sister back for this prank. At the least no one would know, she never told her friends or his own when growing up that he had to wear her hand me downs and hoped that would stay the same. When he pulled the soft cotton underwear up he felt the material press against his dick. The panties were not made to hold male genitals and the little pink bow over the natural bulge was unsettling.

He picked up the towel to wrap it around himself, but then just tossed it on the floor in the corner. If she wanted her laugh he would give it to her so this could be over with. Stepping out into the room Gabe tilted his head back with a smug grin. "Have your laugh now, because I'm not embarrassed." He lied the best he could. Maria looked at her brother with his hairy legs in the panties and did a poor job holding in a laugh. "Okay, good keep up that spirit. The rest of your outfit is on the bed."

His heart sank as he saw what she had laid out for him. On the bed was a purple tartan plaid pleated skirt, some obviously girls thin socks, and a white dress shirt. "Oh come on, you have to be kidding me!"

Maria smiled warmly. "Whatever do you mean?" As positive as her smile was, his glare was the opposite and more.

"These are all girl clothes, I can't wear them… where did you even get them?" She looked over at the articles in the bed and pointed to the skirt. "That came from Sarah, and so did your panties. She was happy to donate some clothes when I told her one of the other girls needed clothes badly. A tragic story of what she was wearing getting ruined and how the airline lost her bag. Abigail donated the shirt, the socks and the shoes. She gave you the shoes she was going to wear for the banquet tomorrow night."

"What shoes?" Gabe started to ask, but now that he was looking he saw a pair on the ground, a pair of glossy black rounded toe three inch heels. "Why… Why did you tell them you needed clothes for a girl? No scratch that, why didn't you just borrow from the boys or better yet. Go down to the gift shop and get me something cheap?"

Seeing him get flabbergasted and red faced was well worth the time to gather the clothes. "One, because I'm not spending money on you. Two because this is funnier, but if you like you can go put a towel on and visit the boys, or go in your cute panties." Why the hell did she have to be like this? No he was sure why.

"You could have just taken my card from my wallet. Madre de Dios.” He cried out mother of God, completely frustrated by his sister. “Are you doing this because I tried to leave your shit school?" Maria thought she had her fun, it would have been a hoot and a half to see her brother leave in the skirt with his hairy legs and walking in the heels, but she could just as easily spend his money. She did pointedly ignore his comment about the school. It was a good school, and she loved teaching the kids, seeing their passions come to life in drama. "Okay, where is your wallet?"

That was a very good question he thought as he looked over at the night stands next to the bed. "Ahh, just a second." He said as he walked over to them, opened the drawers. Inside he found a copy of the Bible, a channel guide for the TV and the remote, but no wallet. He looked under the bed and riffled through the sheets. "¡Mierda!” Gabe yelled shit, his most used curse word. “My wallet could be at that last bar I went to or… no I would have had to pay for my ride back here. My wallet was in my pants I gave to that stupid cow!"

He hung his head for a second before looking back up to his sister for sympathy. "I lost my wallet, can I borrow some money for the trip?" Maria's face darkened at the mention of money. She was sick and tired of the financial burden of her little brother falling on her. Their mother didn't magically have the money to help him with college, that was her. Her Madre came to her asking for help, she felt so guilty for not having enough to provide for them growing up, but still she was proud her little boy got accepted into such a good school and she couldn't tell him no. She hardly ever could. So Maria helped pay for his school, not that he knew. Though it was grating on her how he acted superior because of his degree. He helped with the house's finances now, but complained about it constantly.

"No I don't think so, if you are so irresponsible as to lose your wallet you get to put on the skirt that was lent to you and walk yourself down to the mall and use your vouchers."

Gabe looked down at the clothes again. Wondering what he could do about the situation. No money, no clothes beyond what Maria got him just to mess with him. Irresponsible his ass, it wasn't his fault that woman did something with his pants. Sure he was drunk and forgot his wallet in them, but if she wasn't a bad employee the hotel would have returned it to him.

Then something occurred to him about the clothes and Maria not willing to help. "I will just talk to the boys, just tell me what rooms they are in and I will call them, but sis… I will need money for food at least for the trip."

Maria thought about telling him to live off of the free saltine crackers and brunch the hotel had, but she too did remember how hard it was when they had almost no food. If she hadn't already been fully grown, maybe she would be scrawny, or maybe she would be taller than she is now. "I will make you a deal. You wear the clothes I got you and I will pay for your food this weekend." Maria really wanted to take him down a peg, she was happy with just the panties, but after hearing how his little drinking binge lost him his suit, wallet and not to mention the job. The very reason he wasn't around for the flight over to D.C.

Gabe on the other hand looked at the girls clothes, picked up the skirt, decided he could live off of one meal a day, it was not worth it. He looked up at his sister to say as much when he saw her take a photo of him. A photo that would show him in panties and holding up a skirt. "Also, I won't post this on Facebook and tag you."

Throwing down the skirt he took two steps over to his sister. He was so focused on the idea of snatching her phone he didn't consider what she was capable of. As he reached out she grabbed his arm and twisted him around, tossing him much easier than he would like to admit onto the bed.

As he lay there his head still throbbing, he gave it a second to catch up with what happened. He heard her phone go off again. Gabe now wasn't sure why he tried that, he knew his sister was big on those self defense classes that she started taking the moment she got her first job at a local salon as a teen. "That didn't work out very well for you. So now that I have another photo, one with you laying next to your girly clothes with your butt in the air are you going to put them on or shall I post them? Consider this though, while you will be embarrassed and people will absolutely make fun of you, it will still be better than all of your old college friends seeing them. Or at least I would guess."