Teacher's Challenge

"Well, how did it go? Why haven't you called me yet?" It was Carol on the other end of the phone.

"Just busy with classes and grading papers and stuff, and a little distracted by all the attention I've been getting. It's almost surreal." I laughed.

"Kind of fun, though, isn't it?"

"Exhilarating is what it is. The boys can't keep their eyes off me, and I love it. I've even caught some of the faculty checking me out, and Dean Wagner," I paused, "holy shit, Carol." I could feel myself blush at the realization that I almost shared a lot more than I was willing to.

"What, did something happen?"

"Let's just say I may have gotten a little too much into character," I laughed nervously. I was only making things worse.

"Erica, what happened?" I could feel myself blushing and knew she could sense my nerves through the phone.

"Um, I Gotta go. One of my students needs something." I hung up before she could press me for details.

"Details, little sister..." Carol texted me. I knew she wouldn't let it go and eventually I'd have to tell her, but I had some things to figure out first.

Leaving the few boys that were still in the common room the last innings of whatever baseball game they were watching; I went to take a bath and go to bed. Day one had been long and stressful. I was going to need all my beauty sleep to be ready for day two.

Tuesday was a nice light fit and flair dress with stockings, garters and four-inch heels, I loved the way the light fabric danced around my legs as I walked across campus, Wednesday, a cute sweater dress showed off every curve in my body. I wore it with tights and knee boots. Thursday, a simple sundress that was almost too short with sandals. Friday, I went casual with a pair of jeans that looked like I had painted them on and a linen blouse that did an excellent job of just giving away how lacey my bra was. The five-inch heels accented my legs and ass perfectly in the skin-tight jeans.

Most of the boys seemed to come to grips with my new look and tried not to ogle too much, but I had to admit, when the breeze hit just right and my dress flew up and they could see the tops of my stockings, it had to be a challenge. And the way those jeans I wore on Friday fit, well, not a chance.

As the week progressed, a few of the other teachers had upped their game, but most, like the coaches, seemed to have stuck with their original idea and were happy to settle for second place. Miss Reeder was still going with the Jimmy Dean look, which I thought she pulled off magnificently. She even asked me to be her 'date' for the year-end dance that was coming up at the end of the month. I was pulling for her to get second place, for sure.

Five-inch heels are wonderful things for short periods of time, and by the time Friday afternoon got here, all I wanted to do was get them off my feet. I mean, my legs and ass looked amazing in those skintight jeans, but really, my feet were killing me. I laughed at myself as the true realization of how hard it was for women to make themselves as attractive to men as possible.

The envelope leaning up against my door was a surprise, but I picked it up and carried it through the door, kicking off my heels as it closed behind me.

"Ms. Wilson, I hope you enjoy these," was all the note on the envelope said, no signature, no name, just the note. Inside the envelope was a flash drive. Picking up my heels, I made my way to my bedroom to change, eyeing the drive cautiously, my mind racing with thoughts of what it might contain.

I set my briefcase and the flash drive on my desk and wriggled out of my jeans, dropping my blouse and my bra on top of them rather unceremoniously. My breasts bounced and jiggled when I set them free. I was learning why the first thing women did when they got home was take off their bra. I liked the extra weight; it was just nice to not have the bra digging into my sides. Even if I didn't win the big prize, I was learning a valuable lesson and would never take the effort women went through to be attractive for granted again.

Tossing my clothes in the laundry and grabbing a t-shirt, I opted to give the whole braless thing a try, catching a flicker of a thought in the back of my mind, wondering what it would feel like if I kept them.

A glass of wine from the kitchen and I sat at my desk to wrap up some grading so I could enjoy my weekend, letting my mind wander just a bit as I glanced out the window to see a group of students on their way to the pool.

"Why not?" I said it out loud, closed my laptop, leaving the grading for later and dug out one of the bikinis Carol had insisted I buy. Some very strategic tucking, flip-flops, a towel, my copy of Mallory and I headed for the pool to see what trouble I could cause.

The students were deep into a game of water volleyball and rather than inject myself into their fun; I found a spot to get a little sun and just read. I wasn't naïve enough to think I had gone unnoticed and found I was enjoying how the boys were trying not to get caught checking me out. For all intents and purposes, I was an attractive woman. That made me smile.

The warning bell sounded for dinner and the game broke up, the boys heading back to their dorms to change and me to Barrington for the same reason.

"You know, Miss Wilson, you really look like a woman. All the guys think so. I think you're going to win." It was young Mr. Weiss. "Maybe one day I'll have a girlfriend as pretty as you." He blushed and ran off to catch his buddies. I was betting he would.

I was still smiling when I got to the dining hall, many of the students seemed to have gone home for the weekend and our scout troop was off camping, so there weren't many people here, "I could actually relax a little, who would know and who would care. A whole weekend break from makeup, bras, and all that other stuff. The off-campus faculty get a break. Why shouldn't I?"

The idea was gaining steam and then Mr. Weiss saw me and waved and the smile I had been wearing since he had caught me leaving the pool and told me how pretty I was, how much I really looked like a woman returned. It occurred to me I hadn't minded fixing my makeup for dinner and that it was a conscious effort to pick out an outfit I thought looked not just nice but showed off my slim fit body and nice butt.

Yeah, the heels hurt sometimes, and the bra could get old, but I enjoyed having boobs. I was enjoying this, all of it, especially the way the men and boys at the school were treating me, even the ogling and slightly rude comments; I even enjoyed sucking off Dean Wagner off in his office.

I finished my dinner and went for a long walk around the campus, enjoying the cool evening air and the rustle of the breeze through boughs of the hundred-year-old oaks trees that lined the walkways. Every student I passed called me Miss Wilson, and it just felt right.

All I could think of as I made my way up the step of Barrington Hall was, that, if I continued this path for the entire challenge, I might never go back, and I just might be ok with that, too.

"Red Sox are playing," it was Mr. Simpson in the common room.

"I've got some grading to finish up, if they're still playing when I get done, I'll join you for a while.

"I'll save you a seat," he motioned to the empty room and laughed.

I hated grading grammar tests almost as much as my students hated taking them, so I forced my way through them and entered the grades. Leaning back in my chair as I started to close my laptop, and I saw it, the flash drive, sitting there where I had dropped it.

"I hope this thing isn't some kind of virus." I flicked it open and inserted it on the side of my computer, as curious as I was trepidatious about its contents. Pictures, dozens, and dozens of them, all of me taken during the week; at least he was talented with a camera. Some of these were very good, a few even caught some almost risqué moments when I sat just the wrong way, or the wind caught my skirt and showed a little too much leg.

There were pictures of small feminine moments, times when I pulled my hair back with my finger, pursed my lips, or smiled invitingly. There were shots of me looking over my shoulder, my hair flying behind me, pictures of a touch of lace showing through the opening of my blouse caressing the breast underneath, and more suggestive moments like me bending over, stretching the denim of my jeans almost to its breaking point.

I had a stalker.

My mind drifted through the week, trying to place the photos, trying to figure out who had taken them and wondering why they had left them for me without leaving a name. What did they want? What should I do about this kind of attention?

Scanning through the pictures once more, I decided it wasn't so bad. I had never felt this desirous as a man and the care I was taking to look feminine was evidence that there was more to the way I was dealing with this challenge than just the money.

Amidst all the pictures, there was one Word file. Curiosity had won over trepidation, and I clicked the icon and read. It was a short story about a young man at a private school with a crush on one of his teachers; a teacher who was openly transgender. Enthralled, I read on as they built a special relationship, finally culminating in explicit, detailed, erotic, sensual, carnal knowledge. I read all the things the student wanted to do to the teacher and all the things he wanted the teacher to do to him; I read about their tender kisses and the boundaries that they shattered together, all in the realization that, when he graduated, they would never see each other again.

When I had finished, I read it again, and went to change out of my cum-soaked panties. My mind swam in the images the writer had portrayed. What would it feel like to have a man inside me? Dean Wagner had been in my mouth, but in my bottom? Why wasn't I revolted by the idea? Why was my heart racing and why was I licking my lips as the images ran through my imagination?

I recognized the writing and understood exactly what the envelope was. I knew if I went to watch the last inning or two of the baseball game, they could infer it as an acceptance of what the story implied. Mr. Simpson wrote the story. He wanted to be with me. One of my students wanted to have sex with me, sex with me as a woman.

Alan was a senior and almost nineteen, most definitely not a virgin, and as captain of the lacrosse and rowing teams, hard and cut like a rare diamond. But he was also my student. Could I do such a thing? Did I even want to do such a thing? Did I want to live out the fantasy he described in his story? Did I want to be with someone that could make me cum just with his words?

"What's the score?" I sat on the couch next to him, but not too close.

"Were playing the Angels. It's not even close," he smiled at me and turned back to the game. We sat in silence until the game ended.

"Did you like the pictures?" he turned toward me, his arm across the back of the sofa, his long arm just long enough to touch my shoulder. I felt a spark of energy run through me when his finger touched my shoulder; I could feel it in my crotch.

"Yes, they were very nice. You have a good eye; however, a few were a little, um, inappropriate." I smiled and turned toward him, pulling my shoulder from his touch but raising my knee onto the couch inches from his. "You wrote the story very well. I don't think you should submit that one for a grade, though." It was a tossup who blushed worse.

"I'm glad you liked it," his hand fell from the back of the couch as he leaned a little forward, landing on my bare knee. My god, this nineteen-year-old boy knew more about seducing a woman than I did, and I was five, yeah, a whole five years older than him. I could feel my breathing getting faster, my heart beginning to race. The pictures he had painted with his words screamed through my mind; I could feel myself trying to get hard.

Scanning the room to make sure we were truly alone, I couldn't help myself, everything was coming to a head, all the attention, all the praise, the blow job for Dean Wagner, the compliments, the feelings, the textures, the click, click, click of my heels, I was breaking, and I knew it.

"Alan," I put my hand on his, gazing into his piercing blue eyes, noticing how much he reminded me of Henry Cavill, his broad shoulders and strong arms, wondering what it would feel like to be wrapped in them, "do you really want to do all those things you wrote about in your story, because right now, I'm so confused, so excited, so in the moment" I squeezed his hand in mine, "I can't think of anything I want more?"

I knew it was wrong. I knew I was putting my job, my career on the lines. The blow job I could at least justify. Fucking a student was unforgivable; I cried. He slid across the small couch and wrapped me in those wonderful arms, helping me to my feet and down the hall to my room.

When the door closed, he pushed me against the wall and buried his lips in mine. I had been with women, more women than a lot of men my age, but I had never had someone kiss me like this. It was raw, primal; it was hungry, almost violent in its passion. I wrapped my arms around his neck and drove my tongue into his mouth, chasing, sucking his tongue with mine as he inhaled my very soul.

Without breaking our embrace, kissing, and touching each other, leaving a trail of clothes from the door to my bedroom, our passion climbing ever higher and higher, we finally separated as we fell onto the bed.

I watched in awe, trying to catch my breath, trying to find some fraction of common sense that would let me stop what was about to happen, mesmerized as he pulled his t-shirt over his head, exposing his perfect chest, firm pecs, tight abs, my god he was gorgeous.

Slowly, he ran his eyes over my body, imagining what lay beneath the skimpy lingerie I had on. Bending at the waist, he pulled his boxers down his muscled legs, exposing the most magnificent erection I had ever seen.

"What is wrong with me?" a small voice screamed in the back of my head. "I'm a man. This isn't right. This isn't what I want." The voice became a whisper and disappeared as Alan climbed on top of me like a hungry cat, lowering his face to my stomach, leaving a trail of kisses and licks all the way up between my breasts.

"You are so beautiful, truly amazing, you know that don't you?" his fingers caressed my side, drawing a circle around my breast and giving my boobs a gentle squeeze. "Wait, these are real?" He sucked my nipple into his mouth and sucked hard.

Oh my god, I love my boobs.

Pulling his lips to mine I kissed him passionately, my hands roaming across his back, tracing the outlines of the muscles, moving slowly down and across his wonderous glutes, I squeezed matching his moan with one of my own as he ground his cock into my stomach.

"I've never..." I whispered in his ear as our lips parted, gently rolling him onto his back.

"It's ok, whatever you feel comfortable with," he smiled up at me. "Whatever you want to do is fine with me. I just had to be with you. I just had to taste your lips at least once."

Lifting my hips, I pulled my panties down, letting my own erection loose, noting that I was almost as large as Alan and getting a seditious grin in response, we both knew that what we were about to do was an affront to everything Wellington taught and neither of us cared.

I had just straddled him when he threw me on my back and climbed on top of me, pinning my arms above my head and kissing me hard. "Me first." He gave the most deliciously evil laugh. I trembled a little in anticipation.

Leaving a trail of kisses from my neck to my navel, with an extended detour to my breasts, Alan had me writhing in anticipation. When his hand found my erection, I immediately started leaking, the clear liquid serving as a lubricant for his slow metered motions, up and down with a slight twist. His hand felt wonderful on my shaft. I closed my eyes and moaned loudly as his kisses moved to the inside of my thigh and his free hand urged me to open my legs.

Down my leg to the back of my knee, Alan abandoned my aching cock. His kisses and licks sending surges of pleasure coursing through my body. When he began massaging my feet and sucking on my toes, I thought I was going to explode, but he wouldn't let me, holding me on the cusp. All I could do was float and writhe in the slow waves of wonderful feelings that were engulfing my soul.

"Are you ready?" he whispered in my ear. I had no words. I just nodded.

"What are you ready for?" he was toying with me.

"Whatever you want, anything, just please..." I could barely make the words.

He left me for just a moment, another ploy. The absence of his touch was worse than being trapped on the edge. I reached for my cock to try and finish what we had started, only to be greeted with a gentle slap, knocking my hand away.

Alan was back between my legs, taking my cock in his mouth, sucking it slowly, teasing it with his tongue, bringing me back to the precipice as he pushed my knees gently up toward my shoulders. Subconsciously, I must have known what he was doing, but I didn't care. This beautiful young man had played me perfectly; At this moment, I would do whatever he wanted.

When his cool, slick fingers started massaging my hole, all I could do was moan and press into them. I was lost. When they pressed inside, I knew they were preparing the way for the release I so badly needed. "Yes, Alan, yes, please." I begged.

First there was the pressure and then the sting of being violated, followed by the fullness and then something, something different from anything I had ever experienced. I never knew my ass was so sensitive, so eager to be played with, so hungry to be used like Alan was using it. He moved into me slowly at first, his eyes locked onto mine, reassuring me while his hands moved over my body, fondling my breasts, and then moving out my arms to pin my hands to the bed above my head as he plunged deep inside me.

I exploded, my hot juice coating his and my stomachs. My body froze, spasms and tremors of sexual energy coursing through me. It was an orgasm unlike any I had ever had. There was no quick release. This went on and on, surge after surge of intense pleasure coming from somewhere deep inside me and as Alan thrust his cock into my bowels, the tremors kept coming one after another after another.

Men aren't supposed to have multiple orgasms, but I wasn't being fucked like a man. I never got soft. I came twice, three times, Alan's cock driving me from one peak to the next, our lips locked in passionate kisses until I felt him pulse inside me. At that moment, I was his. He had claimed me like no one ever would again, his seed deep inside me, my virginity would always, and forever, be his.

"Alan, that was amazing. I didn't know I could feel like that." I wrapped my arms around him as he collapsed on top of me, my feet curled behind him, holding him inside me. My god, what had I done?

Gently kissing away the tears that filled my eyes, Alan lifted his body from mine, both of us covered in cum. "My pleasure, but I think we could both use a shower." He smiled and kissed my lips.

My mind was numb in the realization that I had just had sex. One of my students had fucked me raw. I let him lead me gently to the bathroom. Like a small child, I stood and watched as he started the shower. Like a toy doll, I stood there as he removed my bra, like a puppy on a leash, I stepped into the hot spray with him, closing my eyes and relishing the feel of his hands on me again as he gently washed the residue of our sex from my body.

"Are you going to be, ok?" he wrapped me in his arms and kissed my shoulder from behind.

I held his arms in place. "I don't know. What we did, it's so wrong in so many ways, I never should have..." I couldn't finish the sentence.