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Maybe, It Gets Better

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Trans teacher Ana spends the night with three teen girls.
  • May 2021 monthly contest
20.4k words
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Hello Readers! This is, in many ways, a fantasy story. Maybe even more fantastic than that alien story I wrote one time. But the beautiful thing about this fantasy is that we can make it come true! I hope reading this story makes you feel good (and horny). Enjoy!

* * * * *

"Well, I understand that Muriel, but you were the one who told me not to follow along. The fu..." I caught myself, "The hell you didn't Muriel! Well it was Carl who said I could get there early and get checked in and you said it was such a GENIUS idea..."

I should have known that morning when there weren't enough seats on the charter bus for all of the students, that this field trip (like all fucking field trips, to be honest with you) was going to be an absolute shit show. But Carl (my principal) and Muriel (the social studies department head) had convinced me that it was a great opportunity! I could take my car (why my car? Because my ex-husband had insisted on an SUV. And now it was my SUV and I had extra space for the three over-flow students) and I could handle the logistics at the hotel for the night before the bus arrived. Beyond that, once we got to Washington, DC (the site of this year's senior field trip), the teachers would have a car to use if they needed it. And, predictably, the whole plan had now gone to shit.

"Mrs. S...Mrs. S...," Casey Martin from my homeroom said from behind me, she was poking my shoulder, "Ms. aren't supposed to use a hand held self-phone while driving in this state. Especially not at night," she said nervously. I shrugged her finger off of my shoulder.

"Casey, a little busy," I said, rolling my eyes. She sat back, crossing her arms in front of her breasts and huffing. Wounded. It was absolutely on-brand for Casey. She was our senior class president and desperate to already be old and responsible. I was convinced that the 'popular' clique only put up with Casey because she had the largest breasts in the senior class, and she kept the boys interested.

Okay, not just that, she was a legitimate beauty. She was average height, maybe 5'6 or so. She had a build that was somehow petite and voluptuous at the same time. A narrow waist, those big boobs, and very wide hips. She had shoulder-length hair dyed a bright red color, big blue eyes, a Monroe piercing, and big pink lips. She had very pale, almost impossibly pale skin. So, yes, gorgeous. But my goodness, she could be uptight.

Alright, that isn't fair. There were probably worse kids in the class. And, if I had to admit it I would say that she was a great student, sweet to everyone in the school, and she had a subtle sense of humor when you really listened to her. She was just not the kind of student that I usually found myself connecting with. And she was more than a little annoying, poking my shoulder and trying to give me a traffic ticket.

"Mrs. S...," Chloe Oliver said from the passenger seat, "What's the fucking problem?" And then she smiled. I rolled my eyes again, put my hand over the microphone on my cell

"Come on Chloe, its like we are in school right now. Don't make me write you for bad language up on a field trip," I said. Chloe was the undisputed leader of my school's little 'popular' clique. She liked to pretend like she had a little bit of an attitude, but in reality she was a more of a coward and a conformist. She just wanted to have a reputation for being slightly rebellious at school. But in my Sociology class, she was attentive and obsequious. She was only rebellious when it didn't cost her anything. Some kids didn't have that option. When I was 18, I certainly didn't.

Still, I figured the whole attitude was to counteract her wholesome girl-next-door look. She had long, gently wavy brown hair with perfect rich girl blonde high lights. She had sleepy brown eyes and small, delicate nose. She had pretty red lips and her two front teeth were a little crooked, but not so much that they looked silly. She was a little taller than Casey, maybe 5'7. She had that classic hourglass shape with high firm breasts, well-proportioned hips, and a tiny waist. Her legs looked longer than they should have given her height. She had the perfectly tanned shade of skin that only a rich white girl can get.

"No, but really, what is the problem Mrs. S?" Natalie Doe asked from the seat next to Casey. I didn't know Natalie as well as the other girls. I knew that she had a bit of a reputation of being Chloe's loyal second. Always around to voice support for whatever the queen bee wanted, but a little timid on her own. Which was enough make me annoyed by her most of the time. With that said, I always got the feeling that there was something more to her She had a sly smile that seemed to indicate she saw more than she commented on. I took her to be a bit of a dispassionate observer, and I noted that she wrote excellent articles in the school paper. As a result, I granted her some grudging respect. Though I figured I would like her less if I knew he better.

She, like the other 'popular' girls who had volunteered to avoid the bus with, was a pretty girl. She was short, maybe 5'4 and had those small, but perfectly perky breasts that only petite girls can have. She had a lithe, slim body. She had incredibly long, black hair and big brown eyes. She had a sort of wide nose, but one that worked perfectly with her somewhat round face. She had very wide mouth with generous lips and perfect, I mean perfect teeth. I had met her parents at some sort of after school event, one was black and the other was east Asian, and she pretty, brown skin.

"The fucking bus broke down a hundred miles behind us. They have been trying to call, but I didn't have a signal until now," I hissed, trying to get the girls to quiet down.

"Language, Ms. S!" Chloe said, clucking her tongue and shaking her head exaggeratedly. I stared daggers at Chloe, but decided it wasn't worth trying to start a fight over it. She was, technically right.

"Okay, just give me a second to figure out what is going on, please," I said and the girls all nodded understandingly. Which also sort of annoyed me.

If it isn't clear already, I was not exactly excited to have ANY three students in my car, but I was particularly not thrilled about these three. For reasons I could not entirely understand, the popular girls this year had decided that I was their 'fun' teacher this year. The one they all liked. Which made no sense to me, because I made it my business to be as mean to my students as humanly possible. Lots of homework, lots of pop quizzes, whatever. The world wouldn't coddle them when they got out.

I didn't cut the pretty girls (or handsome boys for that matter) any extra slack either. If anything, I was rougher on them, because I assumed that everyone else was cutting them slack. Well, I mean, that was some of it. I think a lot of it was probably that my various high school wounds were still really fresh (despite being twenty year old scars at this point), and I recognized these kinds of girls. The pretty, privileged, socially gifted girls who could cut lesser students to the quick without even realizing they did it. The kind of girls who had once tried to destroy me. Or didn't even try, just nearly killed me incidentally while carelessly living their unblemished lives.

So whether it was entirely fair or not, I was often quite rough and short with the popular girls. And I now had this new theory that high school students were like cats: the more dismissive you were, the more they respected you and wanted to be your friend. And so despite my (somewhat concealed) contempt, they spent their mornings in my homeroom, talking to me and joking. They sometimes swung by for lunch or while they waited for rides. Occasionally, when I wasn't paying attention, I almost sort of liked them.

And so I was not surprised when the three little queens of our small school had quickly volunteered to ride with me when the option arose. I supposed I should have been relieved. I could have picked thousands of other combinations of three 18-year-old kids (even some of the other girls or boys in the popular clique) that would have been a lot harder to control during a road trip. The just rubbed some very sensitive spots quite raw, just being themselves.

Regardless, when I really wanted to flatter my ego, I sometimes wondered if maybe they liked me because finally I had gone from the ugly duckling to something resembling a swan. I was 38 years old, but certainly fit in better with these girls now than I ever would have at high school. In fact, this year was the first year I had been happy with the way I looked in years.

Some of that, I think, was that I had finally finished going through a brutally painful divorce. I really don't want to get into everything that went down with Jerry, but it was a relief to be out from under him. And, when the divorce went through, I realized that I had been living under a sort of low-grade depression for years without even realizing it. I hadn't been taking care of myself as well as I had in the past. Didn't look after my appearance. This year, back in the dating scene, that had change.

I mean, I felt like I looked good. I was (and am) very short, only about 5'2. I have long auburn-brown hair that I wear straight with long bangs. I have almond shaped (and colored) eyes and a tiny little nose that I am very proud of. I have a wide mouth with pouty lips. I have somewhat large, round breasts, a flat stomach, and what the kids now call thicc thighs and a big butt. My family was from Mexico (despite the fact that I still went by my married name, Sokolowski. Ana Sokolowksi nee Garcia) and I had clear bronze skin. But anytime I allowed myself to have these thoughts, I immediately felt disgusted with myself. Not only because it was a bit pathetic at my age to even compare myself to 18-year-old beauties, but also because even thinking of myself as the kind of person who would fit in with them felt a bit like a betrayal. Like I was stabbing a younger version of myself in the back, a girl who in no way would have been invited along for this ride 20 years ago.

Eventually, Muriel filled me in on the new plan, such as it was, and I hung up my phone. I angrily threw it down into the cup holder between the from seats and let out a loud sigh. The girls were entirely silent, but they were all looking at me, waiting for the information.

"Haven't all your friends texted you and told you what is up?" I asked.

"You're the only one with a signal here," Chloe said, in a voice that indicated that it may kill her.

"It's that teacher salary, lets me get the really good service," I laughed, but I decided not to torture them. Less for them, and more because I didn't want to hear them whine. I would fill them in, "So they can't get the bus fixed. The charter company is sending another bus, but it has to come from back home. So they aren't going to make it to the motel tonight. They are in...Boyntown or some damn place. There is a motel, and the towing company is ferrying students to it in pairs. They will start again in the morning on the new bus," I said. The girls laughed at their peers' misfortune. I smiled too.

"So what happens with us?" Casey asked. I sort of shrugged.

"Its already, oh man, 10:30," I said, looking at the glowing clock in the dashboard, "It would take us two hours to drive back and meet up with them. So we are going to drive on to the hotel we were all supposed to stay at. We will stay there, and in the morning we will follow behind the bus when it gets here," I explained. Honestly, I had ended up on the long end of the stick this time. Three girls would soon be shunted away to their own private room. I would have mine. I could sleep naked and I wouldn't have to chit-chat with Muriel.

"So we don't have to deal with Cathy Sutherland and we get to sleep in a little?" Natalie asked raising he eyebrows. Cathy was another member of the popular clique. But I always got the sense that her abrasive style rubbed the others the wrong way. I disliked her more than any of the three here. Still, I had to lay down the law.

"No naming names!" I snapped, But decided no further repercussions were needed, "But yeah, we can sleep in. I think we lucked out," I said. The girls agreed and soon they were chattering pleasantly with one another and leaving me alone while I drove the last twenty miles into Greenville. It was a sleepy little town, little more than a handful of houses, a small hotel, and a gas station. I pulled into the hotel and told the girls to wait in the car while I checked us in.

The lobby was quite dated, with bright orange carpets and wooden panelling on the walls. It screamed: cheap. And I knew instantly why the school board had approved it. There was a goggle-eyed old woman sitting behind the counter typing into a computer with two fingers, and I walked up to her briskly.

"Good evening, my name is Ana Sokolowski. I am here to check in for the two of the rooms in the block of rooms for Franklin County High School," I said sweetly. One room for me. One for the girls. It was going to be a nice, quiet night. I could barely wait to crawl into bed and turn on the TV. The woman typed for a few more seconds, then turned and to look at me. She sighed, bored, and said.

"What's 'at?" And I repeated myself. She looked out the window to the parking lot, seeing my car and no bus, "I was expecting more of you," she said. For the first time I realized how tired I was after a long day on the road. I explained the situation. She shrugged, bored, "Alright, provide the credit card that you used to make the reservation and I will give you all the room keys." I shook my head.

"I don't have the credit card," I explained, "Its the school board's card. I am just checking in. Do you want to see my teacher's ID? It says Franklin County..."

"Need the credit card," the woman said.

"I don't have it," I said exasperated.

"No room keys then," the woman said. I argued with he for another five minutes about it. Offering to call the Muriel, who had actually placed the order, to call Carl as the principal. Finally, I offered to call the president of the school board to have him confirm the purchase. She said it was 'corporate policy' and she wouldn't budge Finally, I gave up.

"Fine, look, I will pay for a room on my own credit card," I said, reaching into my purse. The lady shook her head.

"Can't rent you a room," she said.

"I told you, my credit card. You can swipe it here. Right now. Have a driver's license and everything," I said, annoyed. The woman shook her head again.

"Can't give you a room, we are sold out. No vacancy," She said. I looked around the empty lobby. The entire building was as silent as a tomb. I looked out the window. There appeared to be two cars in the parking lot. Mine. And my friendly neighborhood clerk.

"There is no one here! It is 11 o'clock already!" I said, almost laughing.

"We got a whole high school full of kids coming in tonight," she said, not the slightest hint of recognition. Now I did laugh.

"Ma'am, that is my school! That is what we've been talking about the whole time. Those rooms are going to be empty all night..." I said.

"Don't matter to us if people are in them. No one called before 9 p.m. to cancel the rooms, so Franklin County High School will be billed for the rooms. They will have to pay for them. Those rooms are occupied," she said, looking back at her computer. I nearly screamed

"Then give me one of them!"

"If they show up and I gave away a room to you, I'd be in a heap of shit," she said.

"They aren't showing up!" I yelled at her. She turned away from her computer and gave me a sour look.

"So says you," she said.

"Your theory is that I have somehow infiltrated the Franklin County High School system and learned they were going to be stopping here for the night, waylaid them somehow and stole a Franklin County High School teacher's ID, and then showed up here to steal two rooms. And not even steal them, but pay for them. Is that the theory?" I said, laughing again.

"The theory is the rooms are already paid for. So I don't give a shit," she said.

"You could get paid twice for them!" I shot back.

"I don't own this damned hotel. I don't care even a little bit how much money it makes," she said and I sighed. I ran my hands through my hair. I didn't know if it was because I was on a field trip or because I was transporting three teenage girls, but somehow all those high school frustrations were bubbling up. Here was I was, being punished with arbitrary rules for things that I absolutely could not control. Couldn't get this...person to believe I was who I said I was. I opened my purse and went to return my credit card to where it belonged. I saw the cash I had put in there for the trip. $300.00. I sighed again. Whatever. I guessed, as usual, I would have to pay an extra price to get out of this mess

"How about I make this pay for you?" I said, pulling a hundred dollar bill out of the purse and laying it on the counter. The woman looked at it out of the corner of her eyes. She paused for a long time.

"I can't give you one of the rented rooms, if someone finds out..." she said, and she looked out the door, like someone from corporate was going to show up and audit her. I rolled my eyes and slipped out another hundred.

"How about a room that isn't necessarily a room. Just a place where maybe you could lay out some cots. A storage room or laundry room or something. Just one little room," I said. The woman's eyebrows raised.

* * * * *

Five minutes later Casey, Chloe, Natalie, and I stepped into the hotel's "linen closet." It was about the same size of a hotel room, and in fact might have been originally designed to be one. We entered in one corner of the room and there was a narrow entryway with a closet. To the left there was a spot was where you'd expect to find a bathroom. But instead of a bathroom, there was a large closet with a dirty washtub, a mop, and a bucket. Beyond the washroom was the main, rectangular room about the size of a standard hotel room. Lining the four walls of the room were metal shelves, stuffed with blankets and sheets. Running through the center of the room were another set of freestanding metal shelves, stuffed with towels. It was maybe two or three feet wide. There was a little rectangular walking path, maybe four three feet wide, between those two sets of shelves, all around the room. The clerk had set out four cots, one on each side of this rectangular path.

"You can use the bathroom in the lobby at night if you need it. Don't use the washtub as a toilet" the clerk said, as she handed me a key, "When you need to shower in the morning, I will let you use another room." I took the key with...ill grace, and shut the door behind her.

"Mrs. S...Mrs. S...?" a voice said. The girls had dropped their bags on the floor and were looking, disgusted, around the room. I turned an saw Casey looking at me, sort of pained.

"What?" I asked, sharply. More sharply than I should of.

"I know it has been a tough day, and I don't mean to bother you..." Casey said, and I immediately felt bad. They weren't really doing anything wrong. I was just frustrated.

"It's alright, I am upset with the hotel and the bus and...everything, not you," I said, giving a wan smile. Placated, Casey kept talking.

"But we were supposed to get dinner when everyone got here, and we haven't eaten since lunch," she said. I sighed, and felt my own stomach aching with hunger.

"I saw the burger place we were supposed to go to as we came into town," Chloe said casually, "It was closed." I swore under my breath and looked at my phone. It was 11:12 p.m.

"Dammit, it must have closed at 11," I said. Chloe shook her head.

"No, I mean closed closed," Chloe said, unzipping her back and taking out some clothes, "Like gutted. Did no one do any research at ALL before this trip?" She asked. That sounded about right. Carl had probably driven through here six years ago, eaten at the restaurant, and just assumed it was still here.


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