Chapter 7

Each of the students had been instructed to bring an outfit that was more upscale, the school even providing a few examples, what they were not told was for what occasion it would be for. Going out somewhere nice for dinner hadn’t been a big surprise, though the teenage idea of going out was more of locations like Bumblepears, a family dining location. Most didn’t even consider an actual fancy restaurant despite the clothing suggestions, such as boys wearing a suit coat with a button up shirt. Making what Gabe ended up in much more formal, the feminized and de-aged teacher ending up standing out in his feminine glory that much more.

Getting to her hotel room Maria pulled out a lavender dress she had picked out for the evening for her younger brother. She held it reverently as she placed it down on the bed as she examined it once more. It wasn’t a long dress, but nothing scandalous. The hem came down just above knee level, with the top coming up to just below the shoulder and a almost transparent patterned lace overlay of the bodice that should come up almost to her siblings neck. Around the waist was a built in wide satin ribbon that would be tied in a bow at the back. It was pretty without crossing the juvenile to adult line. She thought it would be down right flattering on any teen girl, something someone might pick out for a bride’s maid dress or something that could be worn to a homecoming dance.

Pressing his lipstick-covered lips together with the waxy taste filling his mouth, Gabe watched his sister lay out the dress and was about to nay-say her option when he saw her add to it. She pulled out white opera gloves, the type that would go up past a girl’s elbows. While his lips were firmly pressed together in a line, his eyes were close to bulging out at the sheer girlishness. “Maria…”

Turning around Maria held one finger out sternly, not saying a word for that moment. Holding his gaze she moved her hand to point directly at him. “Gabriella, do you think it is appropriate to use an adult's first name? Let alone your mother?”

Ready to snap back, tired in so many ways, physically, mentally, emotionally and overall just really tired of her games he started to speak. “Look…” Though he stopped when he saw that familiar look on her face, that look that she had inherited from their mother. She had shown him her vindictive side with what she bought at the mall with his money, and showed it again with what she was laying out for him to wear. It wasn’t like he didn’t know his sister, that made it feel that much worse now that she seemed to have real power over him instead of just the power she made up in her head when she was bossy. So, instead he answered her question the way she wanted. “Lo siento Mamá, no es apropiado hablarle así a un adulto.” Calling her Mama and saying how it wasn’t appropriate to speak to an adult like that. He said it, but like every other time he just played along with her BS it hurt him to do and at least this time he kept what he thought of her and her little game in his head. ‘Bitch’

Dropping her act and truly addressing her brother, doing so with a satisfied smirk on her face after feeling joy from him acting like a proper girl. “Well, you went through all that work to shave your entire body down there, so I thought it’d be wonderful to show how pretty you look.” Maria’s smirk stayed in place knowing how uncomfortable this entire thing made him feel. “I also got you some nice white gloves and heels to complete the look. Try not to stain your clothes at dinner, I know you can be quite the slob.” She said, pulling the pair of five inch white platform heels from its box.

Gabe saw her put the stiletto sandal heels onto the bed, his willingness to go along with his sister with what she held over him falling away. Thoughts of the dress not being something slutty, it at least covering his fake, stuffed chest all vanished when he saw the footwear she chose. He had seen them in the store, he had even tried them on, doing his best to keep the grimace off his face in front of the dark haired student that had been trying to be his friend, but he thought that had just been Maria messing with him.

“I’m not wearing that! Pick something else from the massive pile of clothes you bought with MY money! And I’m not wearing some come fuck me heels!” Gabe was putting his foot down about this, in a literal way as he lifted his left foot up slightly and stomped it back down. The wedges gave him enough stability to not lose his balance, but they were still foreign enough that the act felt odd.

Seeing Gabe stomp his foot like a child fit perfectly with his current visage, stomping his foot in an act of what she assumed he thought as a masculine physical act sent an entirely different message now. A message that she wasn’t going to accept. “Don’t you start talking like you have leverage here! I have been…” Maria pointed to herself with one hand, the other hand in a loose fist that rested on her hip that she cock to the side. “Working my ass off this morning, this afternoon and tonight to keep track of all these kids.”

The amusement of her brothers appearance waning quickly as she thought of all the extra things her and Sam had to do because Gabriel had fucked up and once more she had to clean up after him. “All work you were supposed to be doing alongside Sam and I. You.” She added extra emphasis to the word. “You came to the heart of our nation to try and get another job because working in a public school is beneath you. You.”

She once more added that little something extra. “You thought to play a political game to earn some credit with our new boss and get the school to pay for your return trip. What did you do? No, you don’t need to answer. You messed up and messed up big. I have gone out of my way again and again to look after you, to help you. What do I get in return?! I get you disrespecting me time and time again and that will end. It will end right now. You will not speak that way to me. Understand?”

‘High fucking horse.’ Gabe thought to himself, trying to figure out where she gets the audacity to make him crossdress and pretend to be a student and expect him to thank her. “You intentionally picked out the more humiliating clothes for me to wear, made me march all around this city in these ridiculous heels. News flash Maria! I’m a boy… a man! Hell even with this crazy story you concocted there is no reason I can’t wear pants and sneakers. Becky is wearing sneakers and yet me… you want me to wear heels high enough that I’m going to fall and break my neck or at best my ankle. Maria… I’m exhausted!” The feminine appearing man said, his voice growing softer at the end, his level of energy showing through with his tone of voice.

Turning her face up to the ceiling Maria stared up for a solid two seconds before trying to work a kink out in her neck. Sure she had been having some fun messing with her brother, but it hadn’t been her intention for him to have to play this part. It was him that screwed things up so royally. She could admit to some fault, but it infuriated her the way he was. It was nothing new for him to blame everyone else for the problems in his life, taking no responsibility.

“So am I.” She shook her head as she looked at her sibling. Sitting down on the edge of the bed she crossed her legs. The hotel had a spa and really wished she could treat herself to it right now, not that she could really afford it.

“Sit down, we have a little time, so we can take a nice moment to relax. Take off your shoes, flesh your toes, take a few deep breaths. Then we are going to get ready for a lovely evening at a restaurant. Eat a delicious meal that the school is paying for I might add. You will spend some time talking with the other teens, your peers and you will do it with a smile on your face. Not causing any more problems.”

She didn’t respond to his claim of this being all he was doing, not yet at least. Rolling her ankle, her feet much more comfortable in her sneakers than the heels she wore on the plane ride. She enjoyed dressing up, it made her feel more confident, it changed the way people treated her. Growing up her mother wanted Maria to be a girly girl, but they couldn’t afford much and yet she made time to use patterns to create dresses for her.

Maria loved her mom, was embarrassed to wear such things growing up, but looking back if she thought about it too long she would cry. The woman did so much with so little, but doted on little Gabriel too much. She didn’t have much of a say on what she got to wear growing up and now that Gabriel was in this position, she didn’t see why he should have a real choice.

With that thought a small smile came to her face, looking over at her brother sitting on the other bed, now shoeless, Maria knew what she was going to do next. Standing up she grabbed the bag of new clothes and pulled something else out. “Gabriella” She started by using the feminine name. It wasn’t hard to figure out that her brother having to answer to the name was a sore spot and thought it really tore him up when she treated him like he really was a teen girl and not an adult. She was an actress, not a professional one like she would have wanted to be, but playing this short person in front of her wasn’t her bothersome brother. It shouldn't be difficult.

“I can tell you aren’t happy with what I chose for our night out. Your grandmother…” The way he squinted at referencing their mom as his or her in this case as grandmother was exactly what she wanted. “Well, she didn’t give me a lot of options on what to wear growing up. I don't have the money to go buy you the dress you really want.” Maria ignored the angry glare, it having a lot less impact than it did a week ago the last time he was upset at her for heaven’s know why. “Now, your best friend bought you this pretty dress. I bet…”

“I’m not friends with a teenage girl, let alone best friends!”

The outburst was to be expected, Gabe had never really been one to hold his tongue, that went double for responding to her and she had pushed him, but at this point Maria didn’t believe she could really give an inch. “Gabriella, I want you to think long and hard about what the worst repercussions could be for making me angry. You may not like the way it is playing out, but imagine for a second, no take a minute. Fully think about what could happen if I stopped helping you and instead decided you weren’t worth the effort.”

She looked harder at her brother before letting out a long sigh. “I’m going to use the powder room, you take the time to consider if it would be best to be the happy teen girl you appear or to be Gabriel DeLeon the highschool math teacher that has been pretending to be a girl.” With that she walked away and shut the door behind her.

Blinking a few times, looking through the curtain that was his mascara covered lashes he watched his older sister go before collapsing backwards onto the bed. Pressing his palms into his face, the desire to just bellow out his frustration. The word bellow was a bit much considering the regular tenor of his voice, making things that much more frustrating. His natural small form and softer voice had made all of this possible.

Yet if his boss Mr. Banks had come upon him smelling of booze, with only his shirt and underwear to his name it still would have been better than what was going on now. He had jumped through hoops to stop that from happening and it all went down hill. Maria messing with him had turned things from bad to worse. ‘Fuck if it hadn’t been for that bimbo at the bar ruining my phone none of this would have happened.’ His thoughts started to drift to the handjob she gave him through his pants at the bar, but he pulled them away. He had met a string of women that had made all this happen and Maria was just one in the bunch.

“Si solo.” Gabe started to say if only, but didn’t finish the sentence, instead slowly sitting up. Having a pretty damn good idea of what would happen if people found out he had crossdressed and pretended to be a teen girl. It would backfire on his sister big for sure, but far as he was concerned she spent too much time acting on feelings rather than proper logic. ‘She chose to teach theater of all things, Maria isn’t exactly the pinnacle of intelligence.’ When his sister, the architect of his small slice of hell reappeared from the bathroom he sat back up and nodded in her direction. “You win, I will do it.”

Stopping in her tracks Maria pretended to not understand as she cocked her head to the side. “You will do what?”

“God… I will pretend to be your daughter.” His own brain betraying him as he gave in, giving him dark thoughts that consisted of what he was currently wearing. The smell, taste and feel of the makeup on his face. His hair that was hanging loose instead of thick with product to be styled. The soft cotton underwear that had no right feeling so nice on his skin that held in his tucked, or semi tucked member at this point. His smooth shaven body, the pull of the bra straps and the light dress that clung to his body with the practically bouncing skirt. It was all there on him and he was committing himself more to it.

“Gabriella Grace DeLeon, I do not know what you are going on about. I’m happy to have you back in my life, but if you want to play this game I suppose I can play a bit along if it will make you happy. Tell me your full name hija.”

Working his jaw from side to side in frustration Gabe went along with the bull shit, thinking about everything he had been made to say and who Gabriella is supposed to be. “My name is Gabriella Grace DeLeon. I am a teen girl and just so thrilled to be spending time with you Mama. You are just so beautiful, and I hope I can grow up to be just like you!” He said as sweetly as he could, feeling his stomach churn as the words came out.

Touching her hand to her chest Maria nodded happily, thrilled at the fake confession. She hadn’t given it a lot of thought, but her brother had a natural talent for acting. A few memories flashed back through her. Getting headshots, paying a man that said he would be her agent and help her get some parts in tv shows, movies. She had been foolish, the money was practically flushed down the toilet.

All she had ever gotten was two casting calls and here her brother was who had been given everything in life and she was positive he had more talent with acting, something she loved, than she would ever have. “That was incredibly sweet of you to say Gabriella, but you don’t need to worry. You are as beautiful as a sunset over the mountains before the sky fills with stars.”

The compliment made Gabe feel uncomfortable and wished she would just stop now that she made her point.

“Now then, where were we? On yes! This dress your best friend gave you is pretty, you could wear it tonight. I bet she would be beside herself, but then you would need to wear this dress.” She motioned to the dress she had picked out for the evening. “Would need to be worn tomorrow to the museum, a bit overdressed for the event, but I can understand the desire to always look your best, overdressed for an event or not.”

‘Be embarrassed now or later… fun choice.’ Gabe thought at first before that morphed into something slightly different. “Be more embarrassed later when the students are going around in shorts and I get the privilege of being used as my sister's doll.’ Briefly he had a piece of a memory when he had burned one of Maria’s dolls that she had on a shelf in her room, he hadn’t done it because he hated her. He had just been full of mischief and was a little interested in fire. The interest waned quickly and he had felt bad about what he had done, but a dark part of his mind wondered if this wasn’t at least partly **** for destroying her doll, to become one for a few days.

Gabe gulped at realizing what his actual options were. It wasn’t really ‘wear dress A’ or ‘wear dress B’. The real choice was between being her dolly or his life being ruined. Picking up the dress laid out on the bed he was about to move into the bathroom when his sibling stopped him. Or at least the flash from her camera had him stop in his place.

“Just a little something to help us remember the dress you chose to wear tonight.” Maria waved her phone slightly, saying without words that she had more **** material on him. “You will need to change your underwear too. I’m sure you got a little sweaty walking around and you need to be your best tonight.”

Keeping his grumbling to himself Gabe retreated to the privacy of the bathroom, horrified at the pieces of fabric in his hands. The underwear, the panties in his hand were a soft, silky satin that felt cool to his touch. They seemed to straddle the border of girly and sexy and both were the farthest thing from what he wanted to wear. Or at least they would be if he hadn’t been given another bra. The overly large cups would soon once again be stuffed, but this time he would be wearing a bra that belonged to him. A topic he wanted to forget about and knew there wouldn’t be a chance to wash it away with whiskey tonight or the next time. He would be walking through this hellscape till he got home.

Removing his current dress Gabe just let it fall to the floor and struggled a little bit before his current bra joined the dress. That was when he caught a glimpse of himself in the mirror. Makeup still in place, not perfect like it had been earlier, but still there. His eyes seemed so large and feminine, his body hairless and tiny or… petite like a girl might say and the panties still on it. The visage felt wrong, considering his height and how he looked it was like looking at some fifteen year old girl, not yet done growing and just starting puberty. ‘Fuck, why did I even think that.’ He shuddered, turning away from the mirror before pulling down the panties.

Feeling the cool air over his dick and balls felt good and looking in the mirror to see his manhood could make him feel better, he was a man and that proved it. The problem was it would be at odds with his hair, lack thereof and what his face currently looked like and he didn’t dare turn to look.

Mentally he was still a man, his trimmed mustache, hair done up just right even if he had neglected getting it cut recently. His brain going off on a bit of a tangent before refocusing to get this over with. Starting with the new bra he clasped the thing in front, getting the little hooks just right before twisting it and getting his arms through the straps. They rested on his shoulders like the last did, the weight of the stuffing not there, not that that was much weight.

The panties were easy to slide up his legs, the material causing a shudder through him, his little man getting slightly excited. ‘Stop, we don’t like this. You just think panties equal female and sex.’ Gabe mentally admonished his dick that had a mind of its own. He wasn't’ the biggest man in the groin region, but not so puny he could not do something about it. Reaching into his underwear he worked on fixing himself down there to keep things out of sight. It wasn’t exactly comfortable, but the last thing he could have done is let someone notice he had a dick.

The dress itself wasn’t difficult to get into, even if he struggled to get he rear zipper pulled all the way up. Fumbling a bit with the satin ribbon around his waist he tried it behind him like he would tie a shoe. Slapping his hand down on the light switches to help avoid looking in the mirror Gabe let out a long sigh as he stood in the dark.

The beginning of a quote coming to mind from some play he was sure his sister would know. ‘Once more unto the breach dear friend.’ Taking a hold of the door handle he opened the door to step out, expecting the flash of Maria’s camera once more and a laugh.

Instead Gabe found his sister sitting at the built-in desk in the room, looking in the mirror as she adjusted her makeup. She had already changed clothing, now wearing a maroon almost off the shoulder dress, that came down to just above her knees much like the dress he wore now, but hers had three quarter sleeves. Gone were her white sneakers, nor did she have on the heels she arrived in. Instead she had on pointed toe T-strap stilettos with thin double wrap straps around her ankles.

“Ah, there you are hermosa.” Maria said, turning in her seat. “That dress looks wonderful tonight, you are going to turn some boy’s heads. Though I can just imagine how you would look if I was able to buy you a nice petticoat for it. A girl like you would look just lovely, it is a shame I couldn’t give you the quinceanera you deserved.”

“I’m not beautiful and I don’t want to turn any boy’s head.” Gave said, looking away from his sister, his cheeks growing pink from a blush. He couldn’t picture himself in a quinceanera dress, but the idea was enough to want to drop dead.

“Aww, Gabriella there is no need for you to have a self esteem issue, I promise you are a beautiful girl. I’m also sure plenty of boys would be interested in dating my beautiful daughter.”

Suddenly feeling exposed he pulled down the hem of the dress, it wasn’t some mini skirt but he felt more than exposed thanks to the unfamiliarity of wearing a dress and his siblings teasing. “Can we just stop, please!”

“We have a lot to do and…” Maria looked over at the bedside clock in the hotel room. “Not a lot of time to do it. I’m going to finish up with my face, why don’t you put on your pretty new shoes. You can walk around a bit to get used to them and then I will help you with your makeup.”

Gabe still had fight left in him, but he was just trying to focus on getting out of this without his life being ruined. Later he would refocus to payback, Maria would get it… but for now he had to figure out how to walk without killing himself. ‘Heel, toe, heel, rolled my foot to toe. One foot in front of the other, move your hips, heel, toe. Elbows in, wrists limp… heel, toe.

Soon enough the students came back to their rooms, Gabe wasn’t sure where he was going to stay, they had talked a bit about it before but so much had been going on he couldn’t remember if he was going to be in the room with his sister, the room with no adults or with the principle. Originally he was going to be in the third room and since he was still an adult, the students knowing that or not, he thought it would be best. Though it wasn’t something he was able to bring up just now as everyone was running around. Opening up duffle bags, pulling out things to wear. Making Gabe incredibly uncomfortable as the teen girls were in different stages of undress with him standing there having gone back to heel practice after his sister put on his face as she put it.

Seeing her fake daughter uncomfortable Maria gave him a hug from behind, whispering in his ear. “Don’t struggle, you will make others ask questions. Why don’t you go wait downstairs and wait for the other kids.” When she let go and stepped back it was a relief to see Gabe do as she said, but before he could make it to the door she just had to turn that proverbial knife. “Love you Gabriella, be a good girl now.”

Hand on the door Gabe didn’t make eye contact as he answered. “Love you too Mama, I wil be a good girl.”