Teacher's Challenge

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Teachers challenged to X-Dress. What could possibly happen?
  • May 2022 monthly contest
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I usually don't publish back-to-back like this but Button, Button was meant to just tide you over until I got this one finished, anyway.

I finally got this one to where I was happy with it, well to a point where I felt I could stop messing with it and share it with my fans. I hope you enjoy the story. I'll admit our hero(ine) is perhaps a little too eager when facing certain challenges, but hey, it's erotic 'fiction' right?

As always, all participants are of an appropriate age for the activities in which they engage and please leave me a comment when you're done.


The Wellington Academy, I couldn't believe it, yes, I had my Master's in Education to go with my Bachelors in Rhetoric and Composition, but I was a first-year teacher with no classroom experience and Wellington was the most prestigious private school in a five-state area, I guess I nailed my teaching demonstration.

Wellington was a residential boy's school, offering a classic liberal arts education filled with things like Latin, Philosophy, and Classical Literature. The school operated a year-round program of four quarters with three weeks off between them. Setting the bar with the highest of academic standards. If you graduated from Wellington, you had a well-rounded education and you could think critically.

Having said all that, Wellington still felt the pressures of social awareness that permeated today's society. The staff or administration could not express any political or social bias; the goal of the school was to teach young minds how to think, not what to think.

With that awareness in mind, the administration let the students pick a topic for each month in the academic calendar; the administration encouraged the faculty to fit the topic into their classes to support the students' efforts to celebrate and understand that social issue.

To say the students did their best to push our buttons was an understatement. It all culminated with the famous senior challenge. The seniors would present ideas to the senior council, who would then choose, then issuing said challenge to the faculty. It ran the gamut, Olympic style sporting events, engineering challenges, arts, music, trivia competitions, even producing and presenting a play. This year, supposedly to promote cultural awareness, the students had challenged the entire faculty to cross dress for the entire month. Transgender awareness was an issue of growing importance, after all.

To sweeten the pot, the kids pitched in ten dollars each. With school matching the prize and the top five faculty members, as judged by the senior council, splitting the pot, the overall winner pocketing half, that was a ten-thousand-dollar payday, and I had a ton of student debt; whatever it took, I was all in.

"Carol, you have to help me," I was begging my older sister for help. "I don't have a clue what to do and that much money would be huge for me. You just have to."

I knew she was going to say yes just like I knew she loved hearing me beg, "Ok, Goldilocks, come see me for the weekend and we'll figure it out, but a whole month, that's going to be a challenge," she laughed, "see you Friday night girly girl." She hung up before I could respond.

Carol was right, a day or two would have been easy, a week doable, but a month? That was going to be tough. I figured if I came on strong, I would have an edge, but for that kind of money, others were going to go for it too and they would up their game to meet mine, so I would have to keep upping the ante, so to speak, or set the initial bar so high, no one could catch me and that meant passing completely day one, and looking damn hot, too.

"Send me your measurements" it was a text from Carol with a diagram of a woman's body with lines across the chest, waist, and hips to use as a guide.

I shook my head and let out a soft laugh, wondering if it was really going to be worth it. I mean, what if nobody else took the challenge, and I went all out for nothing? What if a simple skirt and some low heels would have been enough? I guess I was going to find out on Monday.

Friday afternoon, they read the official rules for the challenge; they would judge all time on campus except for thirty minutes at the start and end of the day and thirty minutes for participants to fine tune their appearance or change to go home. Unfortunately, I was a proctor for the senior dorm and lived on campus; it was an extra five hundred a month and included room and board. Most first-year teachers took the opportunity.

I still got the thirty minutes every morning and afternoon, but my time never ended. Especially with me living in the senior dorm, I was on display to the judges 24/7, shit.

The drive to Carol's wasn't a long one, but I was a bundle of nerves. I hadn't even packed a bag. The realization that I was effectively going to be a girl for the next four weeks weighing heavier and heavier on my mind with every mile I drove; but ten thousand dollars. Damn, that would go a long way, so I kept driving.

"Meet me at the mall. VS." another text from Carol. Shit, VS had to mean Victoria's Secret. She was going for the big guns right out of the bag. What was I getting myself into? The thought ran through my head like a freight train on steroids.

I thought about stopping to eat but knew I needed all the time I had to get ready, and figured that in the state my stomach was in, anything I ate would come right back up anyway, so again, I kept driving.

Five O'clock on the dot, I found Carol standing outside Victoria's Secret, huge smile on her face and a smoothie in her hand for me. "You're really going through with this little brother." She handed me the smoothie, I just nodded and took a long sip. There was rum in the smoothie. God, I loved my sister.

Next door to VS was a place called Accents Aesthetics. Clinic and Day Spa. Fortunately, that was our first stop. Carol admitted she had told me to meet her at VS as a joke. OK, sometimes I loved my sister. We both laughed, and I relaxed.

"Ok, Eric, here's the plan; I already got you some things from next door. They're in the bag. The ladies are going to give you a deluxe makeover and I won't lie. Some of it is going to hurt like hell, but it will all be worth it if you really want to win that money. You just have to trust me; I've spent my entire life trying to look better than everybody around me and I like to think I know what I'm doing."

I had to agree. Carol was a wonderful person and a better sister, but she had always been a diva. Everything she did, everywhere she went, she had to be perfect; she had to look perfect. If she could do half of what she did for herself for me, I would be golden; especially considering what she had to work with. I had inherited my mom's thin build, high cheekbones, and nice round butt, and kept myself in great shape.

"Alright," I took a deep breath, "let's do this." I raised my smoothie to hers and smiled. "For the grand prize." I laughed.

"For the grand prize." Carol answered as the ladies at the spa took me by the arm and led me to the back. I found out later, Carol was getting a full body massage while I was being tortured; full body wax, Brazilian, even my crack, my eyebrows plucked, my ears pierced and extension in my hair. Bright red polish on my nails and a crash course on how to do makeup. There was no time to play games, and I watched intently each step of the way, doing my best not to cry like a little girl as they ripped all my body hair out.

"Ok, little sister. This is the biggie. You need boobs for this to work. We have other options, but if you really want that prize, this is the way to go." Carol led me from the spa toward a sign that said Aesthetics Clinic.

"I called in a couple of favors, and they agreed to squeeze you in. Trust me." She squeezed my hand.

I had to fill out all kinds of forms, like I was seeing a doctor for the first time. Trusting Carol, I just initialed where they told me and signed in what seemed like a dozen places. One for said something about informed consent. I looked at Carol. She nodded. I signed.

"So, they custom fit breast forms or something?"

"Not exactly, but you're going to love the results."

"I need to confirm a few things before we begin." A woman in a lab coat walked in, more interested in the papers in her hand than me.

"Ok." This was odd.

"Please tell me why you're here." She finally looked up at me.

"Um, breasts." I answered meekly.

"And this is your signature on the consent form?"

"Yes, ma'am."

"Alright, let's see what we have here."

She measured me and drew circles on my chest, marking little Xs in a few places around my areolas.

"I can get you to a C cup. For anything larger, you would need implants and we don't do those here. We are strictly an outpatient clinic. Do you understand?"

I looked at Carol. She nodded. "Yes, ma'am."

Local anesthetic and I watched as the doctor injected something into my chest where she had marked the X's, enthralled as perfect perky breasts grew on my chest. It only took about thirty minutes.

"These are semi-permanent. If you want to keep them, you'll have to come in about every six months for a booster."

"Six months?" I looked at Carol.

"Grand prize, little sister, grand prize."

We left the mall just as it closed. I had chosen the simple white panties and bra from the bag. My other choices being black, red, and pink, three sets of panties with one matching bra in each color. Carol helped me into the cute slip dress and into the short heel sandals she had picked out for me to wear. The boobs nestled in my bra, jiggling as I moved, tugging softly at my chest, filling out my dress nicely.

My guy clothes in a bag, my wallet, keys, lipstick and compact in my new purse strung over my shoulder, and the soft click of my heels on the tile echoing through the emptying mall, I followed Carol out to our cars not believing what I had done.

"Tomorrow, shopping. Right now, you must be starving and probably need something stronger than that smoothie." Carol laughed.

I was too shell-shocked to answer, I just followed her and did my best not to notice all the looks I was getting from the people we passed, I knew if I thought about it, I would convince myself they could see right through me and were all laughing at me.

When one man caught my eye and commented, "damn, I bet you're worth the climb. Fuck, you are one hot bitch." I just started laughing. Yes, it had been rude, crude and totally inappropriate and his mom would have probably washed his mouth out of being so crass, but it was exactly what I needed to hear. "Fuck, I'm one hot bitch." I repeated to myself and quickened my step to catch up with Carol.

"Did you hear what that guy said about me?"

"Get used to it. He was right, you are totally hot. You might even be as hot as me." She laughed. "So, you going to be ok with this? It's not too late to change your mind."

"After everything I just went through. I mean, have they ever waxed you like that? They waxed my balls and ass crack for crissakes." I almost yelled, "I have never felt so violated." We both started laughing uncontrollably. "And besides, if I'm really that hot, that ten grand is all but mine; I just know it. Now, let's go eat. I'm starved."

That crass, rude comment from a total stranger had given me an unexpected confidence. I couldn't describe how I felt. I just knew what he had said was true.

Grangers Bar was our go to when I was home and tonight was no different. It was a family pub with excellent beer and better food. Carol and I were going over plans for tomorrow's shopping while we waited for our food.

The place was packed and in a normal world, I would have never in my wildest imagination ever walked in the door dressed like a woman. But I had committed. I had already been through the gauntlet and what could be worse than some strange lady pulling out all your pubes?

I grabbed a table the busboy had just cleaned, and Carol went to the bar to get us drinks. To say the two of us were attracting attention was a mild understatement. Guys were nudging their buddies and trying not to get caught looking; some were even flat out staring and the look on their faces was one I knew all too well. Carol and I were the hottest girls in the bar.

My stomach in my throat, I took a couple of deep breaths and I found some of my nerves, just enough to keep me from running out of the building. Less than five hours ago, I was one of them, a guy ogling hot women as I made my way into the mall to meet with Carol. What had happened in the short time since was changing me in ways I never expected.

I should have been in panic mode. I should have been trying to hide. Instead, I was enjoying the attention. I even caught myself playing with my hair and pretending not to look at Steve, my old darts partner from before I went off to college.

"I wonder if he has a clue?" the thought drifted through my mind just as he caught me looking and made his way across the bar. He arrived at the same time as Carol, and her being my sister, of course, he knew her.

"Carol, who's your friend?" He winked at me and turned to her.

"Steve, nice to see you." She gave him a quick hug. "This is my cousin Erica. She and Eric were actually born on the same day. Can't you see the family resemblance?" She set my beer and two tequila shots down. I downed one of the tequila shots and drained about half of my beer without thinking.

"Well, she got all the good looks." He laughed. "So, Erica, Eric, same birthday, that had to be fun growing up?" Steve's attention had turned to me, and Carol might as well as disappeared.

"You have no idea," I grinned and shot death stares at Carol.

"You in town for long?"

"Nope, just the weekend, Carol and I have a lot of catching up to do, shopping all day tomorrow, maybe a massage or a trip to the spa, you know girl stuff, then I'm headed back home Sunday." Carol tried not to laugh when I mentioned the spa.

"So, no time for me?" he gave me those big puppy dog eyes.

"I have to admit you are awful cute, but not this trip. Maybe next time I'm in town. Carol knows how to get in touch with you, right?" The fact was, his number had been on my phone longer than Carol's.

Steve snagged a pen from the waitress that walked up to our table and wrote his number on a napkin, anyway. "Well, now you do too, and don't make me track you down." He handed me the napkin and watched as I folder it neatly and put it in my purse. Winking at me again, he turned to go back to his buddies.

I had seen Steve work his magic a hundred times. He never asked a girl for their number, instead giving them his and they almost always called. I had to admit it had been fun flirting with him and him not recognizing me was the last piece of the puzzle; there was no doubt I could do this.

"Duuude, your cousin is hot. I can't believe you never set me up. I thought we were tight." A few smiley faces followed Steve's text.

"Cousin, which one? Male or female? LOL" I replied. There was no doubt about Steve's sexuality. Possibly half the girls in town could testify to that, but he would expect the barb.

"Seriously, Erica man, you gotta hook me up here, she's gorgeous," I caught him looking at me across the bar pretending not to notice and trying not to let him see I was on my phone, too.

"I'll see what I can do. I gotta warn you, she a little different from most girls." He has no clue, I thought to myself as I hit send.

"No kidding, man. She's better looking than Carol. Thanks. I'll owe you one if she calls me."

"What are you doing?" Carol could see the devilish grin on my face.

"Texting Steve. He's asking me to set him up with Erica." I handed her the phone. "This girl thing is fun." We both laughed.

We finished our sandwiches and our drinks, and I stopped to wave and wink at Steve on the way out of the pub, "I think I may have created a monster." Carol jabbed me in the shoulder, grabbing my arm and dragging me out the door.

Saturday was busier than I thought. We went back to the mall, to specialty shops, a few big box stores; dresses, jeans, shorts, business suits, pantsuits, skirts, blouses, shoes, swimsuits, bikinis of course, Carol wouldn't have it any other way, more lingerie, and more shoes, and some luggage to put it all in, by the time we got back to Carol's apartment, I was both exhausted and elated. My feet were killing me, but I had mastered the fine art of walking in four-inch heels with just the right amount of wiggle in my hips. Carol paid for everything.

We split a pizza and a bottle of wine and crashed.

I laid in bed running it all through my head, the spa/clinic, my boobs, Steve, and all that shopping. It might have been cheaper to just ask Carol for the money, but it wouldn't have been near as much fun.

Sunday morning, Carol helped me pack, I did my own makeup, picked out a nice tight pair of jeans, and a linen blouse that fit just right, unbuttoned just enough to give a flash of my bra from the right angle, and a pair of heels. Pulling on the killer leather jacket we had found at a secondhand store, my hair up in a high tight ponytail, I took a deep breath and grabbed my purse; Erica was ready for whatever came, or so I thought.

We loaded my car and went to a little outdoor café by the river for lunch and it all sank in as we sat there enjoying the unusually mild weather. "Carol, what am I doing? This is crazy." I took a large sip of my wine, noting the lipstick on the glass and admiring my bright red nails as I set the wine down.

"Oh, so now, after all my hard work, now you get cold feet?" The feigned indignation in her voice made me smile. "You are rocking this thing and if you don't win, I want to see whoever beats you."

"You really think..." my confidence was wavering.

She put her finger on my lips, "Duh, one of your best friends is texting you to set him up with, well, you. What do you think? And besides, you've got boobs now."

I thought about Steve and just laughed.

We talked about last-minute details; I was going to need to find a spa or salon in case my hair came back too fast and I needed another wax job. Carol promised they get easier, or maybe just to get another manicure and pedicure for the fun of it; that I had enjoyed.

We talked about the difference between sexy and slutty, and since I was teaching at an all-boys school, sexy could be my friend, where slutty would get me in serious trouble. That I understood, I had been a teen-aged boy and knew what they were like.

During the drive back to Wellington, I was a bundle of nerves. Everything that could go wrong with this ran through my mind. I was even freaking out about spraining my ankle in the heels I was going to be wearing. By the time I pulled into my spot, I was almost hyperventilating. The only thing that prevented me from backing out was me not having anything to change into or any way to get my makeup off, and as Carol had said, I had boobs now and that spelled commitment.

My first challenge was waiting for me as soon as I unloaded my car; the massive stairs up the Barrington Hall with three suitcases in four-inch heels.

"Can I help you, miss?" I turned to see Alan Simpson, one of my better students, walking up to the dorm.

"I would appreciate that very much," I smiled at him and nodded at my bags.

"Um, miss, this is a boy's dormitory. Are you sure you're in the right place?"

"Quite sure, Mr. Simpson, and by the way, how is the final draft of your paper coming? I am really looking forward to reading it."

"Mr. Wilson, is that really you?" His jaw literally dropped open.

"I guess it will be Miss Wilson for the next month, won't it?" I smiled as I watched him try to regain his composure. "Now, about these bags. Do you think you can help me get them up to my room?"