Teacher's Challenge

It was one of my favorite things about Wellington, the boys that were here were all good kids, or at least trying to be. Their parents paid a ton for their spot, and it was an unwritten understanding that part of the education was how to behave. Classes in etiquette and decorum were mandatory. So, it didn't surprise me when Alan grabbed the two larger bags and headed up the stairs. I took the small one and followed him.

Barrington Hall was the original dorm for the school and was over a hundred years old. My heels clicked on the old hardwood floors as we made our way from the elevator to my apartment, I reveled in the looks I got and the slow recognition that spread across the faces of my boys as Alan and I made our way down the hall.

"Mr. Simpson, thank you for your help. Can you do me a favor and gather the boys in the common room? Based on the looks I've been getting; I think a chat might be in order." I smiled and dug my keys out of my purse.

"Yes, sir, I mean ma'am, I mean..." His face was beet red. "I'll take care of it." He turned and practically ran down the hall.

I took my time unpacking and reorganizing my closet, even laying out the dark gray pins stripe suit I had planned for tomorrow. Carol had agreed that going big day one was the right idea, and this suit was sexy as hell. It fit like I painted it on, and the skirt hit that magic spot just before too short that would show off my legs for maximum effect. With what the five-inch heels did to my legs, the way they cut the jacket and with the right blouse, I was going to make an enormous splash.

There was always a game on in the common room, being May, it could be baseball, hockey, or basketball and regardless of who was playing, the boys were all totally into whatever game it was so the silence that greeted me as I walked in was a surprise. It was occurring to me that when the boys had come up with this idea, they might not have expected anyone to take it to this level.

"So, I'm guessing Mr. Simpson was kind enough to fill you in, so," I did a slow turn, "you guys think I have a chance of winning this thing?"

I spent the next thirty minutes answering questions. "Yes, it's really me. No, I will not prove it." Ok, so not all the boys were total gentlemen, yet.

I told them about my sister and showed a few pictures we had taken while out shopping. The consensus was, I had it in the bag.

With the Q&A over, I settled in with my boys and watched as the Red Sox scored five in the bottom of the ninth to send the Yankees back to New York with another loss, fully aware of the not totally appropriate looks I was getting from some of them, especially Mr. Simpson.

Monday morning started with a nice, hot shower. I may or may not have spent a little longer than usual washing my chest. Lotion and then my panties, garter belt and stockings, relishing the feeling of the nylon sliding up my smooth legs. If I wasn't careful, I was going to have to jack off just to finish getting dressed. I flicked the tip of my erection with my finger, and he softened, giving me the chance to tuck him away. I slipped on my bra; I had chosen a lacey black one specifically, so it would show through the flimsy white silk blouse I was going to wear with my suit.

I stopped to admire myself in the mirror for a minute, snapping a picture with my phone. The sultry look on my face as the tip of my tongue caressed my upper lip was too hot. My blouse unbuttoned probably one button too far, I slipped on my skirt, smoothing it against my body and turning to admire the feminine form it was covering, noting that if I wasn't careful, the top of my stockings just might peek out: perfect. I smiled at my reflection and pulled on the jacket for the suit, buttoning the button to accent my bust.

Checking my hair and makeup one last time, stepping into my heels, admiring what the five-inch stilettos did to my calves and ass, grabbing my purse and my briefcase, I took a deep breath and headed to the cafeteria for breakfast and my big reveal.

The walk across campus was surreal. Everyone I passed did a double take. Some stopped to make sure I wasn't lost, and a few openly flirted with me. My heels clicked on the cement, and I added a little more swish to my hips, a strange feeling of confidence filling me; I was loving this.

Breakfast at Wellington also served as a venue for general announcements and dissemination of other important information, so all students and faculty were required to attend. It was the official start of the Wellington Day. This day was a bit more festive than most, as all the teachers taking part in the challenge were showing their stuff for the first time.

There were guys in skirts, I had expected that, many had obviously gotten outside help just as I had and looked pretty good, the coaches went for the absurd, outlandish wigs, huge fake boobs, and overdone makeup, only a few of us had swung for the fences. With Carol's help, I was prepared for that too.

Even Ms. Reeder, the sole female on the faculty, had stepped up. She was now sporting a serious pompadour and a couple of fake tattoos to go with her rolled-up shirtsleeves and biker boots. She looked like she had stepped out of a poster for an old Jimmy Dean movie.

What I wasn't prepared for was the reaction of the students, word had spread quickly about the blonde bombshell that had come home to Barrington Hall last night and while I had gotten a taste of what male attention felt like, Steve coming on to me was nothing compared to a thousand hormone fueled teenage boys and the way they stared at me as I walked across the cafeteria to my seat at the faculty table, each one undressing me in their mind, the click, click, click of my heels echoing through the room as it slowly fell silent.

The confidence that had been growing as I crossed the campus reached critical mass when I arrived at my seat, I set down my briefcase, slipped off my jacket, I shook my hair loose, smoothed my skirt, and took my compact out of my purse, refreshing my bright red lipstick. Amid the audible sighs, someone fell out of their chair. Score one for Miss Wilson. I smiled as I sat down, making sure everyone saw me cross my legs. I was loving everything about this, absolutely everything.

Dean Wagner complimented everyone on the participation, recognizing the coaches for their contribution and admonishing the students that they had all been instructed in decorum and were expected to know how to treat a lady. That sent a ripple of laughter through the entire room. The rest of the announcements were normal, and our day began. For the first time since I started, no one was late to my first period class.

As Mr. Wilson, I had always taught from the blackboard, today I decided to push the envelope a little, taking a seat on my desk facing my students with my legs crossed as we continued our discussion of the Arthurian mythos in Mallory's 'Le Morte d'Arthur.'

I had every boy's undivided attention but wasn't sure just how much we really got done. The rest of my classes were the same, they all knew exactly who I was and what was going on, but I guess tight skirts, garters, stockings, high heels, and a hint of lace were just too much for the hormone overload that filled my classes.

It was a bit of a relief to sit by myself in my classroom grading mid-term creative writing assignments over my lunch break. As much fun as it was and as much as I was reveling in all the testosterone fueled attention, the downtime was nice. I was saving Mr. Simpson's paper for last. He had genuine talent, and I hoped wherever he ended up after he graduated, he would pursue his writing.

"Miss Wilson," I had quickly come to enjoy being called that. Arnold Weiss, one of the freshmen, was at my door.

"Yes Mr. Weiss?" How can I help you?" I gave him a smile and he seemed to relax.

"Um, Dean Wagner asked me to come ask you to meet him in his office," Mr. Weiss was a shy, awkward young man with serious potential to be a real lady killer if he ever figured out how cute he really was. Some girl was going to rock his world, sucking him off in the back seat of his dad's Buick, and it would be game on. I hoped I got to see the results of that transition one day.

"Thank you, Mr. Weiss. I'll head right over." I closed my laptop, pulled on my jacket, and checked my makeup, redoing my lipstick, as I followed him out the door.

"Dean Wagner, I was told you wanted to see me." I don't know why, really, but Dean Wagner intimidated the hell out of me. He was a nice man and a good boss, offering constructive guidance and helpful suggestions as I got my teaching legs under me. It was, well, he was just a big man, at least 6' 6" and probably close to 300 lbs. Most of the students referred to him as the gentle giant, but my gut told me there was something else under that kind demeanor. I just couldn't put a finger on it.

"Please come in and sit down. I guess it's Miss Wilson for the next few weeks," he emphasized 'Miss' and smiled at me. I relaxed. "You've really gone above and beyond on the challenge. You are all everyone is talking about. Even the coaches are taking a back seat." He looked at me a little sideways. "If it's not too personal, can I ask if this is something you have done before?"

"Um, no sir, I have an older sister, Carol, who's kind of a fashion diva, if you know what I mean. When I told her about the challenge, she was all over it. Most of this is her fault." I gave a weak laugh. "The first time I put anything like this on was Friday."

"Wow, well I think you have this I the bag, if you can keep it up." He smiled again, and I could have sworn he winked at me.

"You should see my closet. Carol made sure I was loaded for bear. So, is this what you wanted to talk about?" I was fidgeting nervously in my chair, unconsciously crossing and recrossing my legs.

"It's part of it, I guess," he got up and walked around in front of his desk, "I mean it exhibits your level of commitment to the Wellington culture, but I just wanted to touch base on how you felt you were doing, the committee will meet at the end of this term to consider making your position permanent."

"Well, frankly, I love it here. The boys are amazing, bright, eager to learn, and gentlemen to the man. The rest of the faculty is amazing, and even being a dorm proctor, well it gives me an insight into the students that has been invaluable, plus I get to talk about things that I love, we're doing the Arthur legend in literature right now." I had uncrossed my legs and leaned forward. I did love this job.

"That's good to hear. I am getting very positive feedback from the students I have talked with, and your peers agree you're a good fit." He sat back on his desk and spread his legs a bit. "I just need to write my recommendation and I think you can count on a very nice offer from the committee." His kind smile had turned into a leer.

"Thank you. From what you've said, can I expect a positive recommendation?"

"I think we can make that happen, if you're willing to show me the full extent of your dedication, that is." He licked his lips. "You make a stunning young woman, you know, and it's obvious you freshened your lipstick before you came to see me?"

"Dean Wagner, just what are you implying?" I knew what he wanted. My head was reeling with the thought, and from the way he had phrased it, my job was on the line; I was going to suck his cock and get a good recommendation or have my career ruined.

"I think you know very well, Miss Wilson. You do me a favor and I do you a favor. It's that simple." I could see the bulge growing in his crotch. "Now, don't you think this would be easier if you were on your knees right now?"

My mind raced through my options as I felt a lump in my throat. I did love my job and with all my student debt, didn't have enough resources to support myself if I lost it. I guessed I could move in with Carol for a while, but that wasn't the best option, and what kind of recommendation would I get if I said no?

I didn't have a choice. Sliding from the chair onto my knees, I looked up at Dean Wagner as he stepped toward me.

"I knew you'd see things my way." He stepped forward and unzipped his pants. "Take off your jacket and blouse. I'd hate for anything to get stained," he laughed. I did what he suggested, exposing my lacey black push-up bra and my ample breasts.

Tentatively, I reached up and unfastened his belt, my heart racing, my mind spinning. Was I really going to do this? What if I wasn't any good at it? Would he still give me a recommendation? What if I was too good at it? Would he expect me to do it again? The questions wouldn't stop. His belt came free, the button on his slacks slipped from the loop, and his pants fell to the floor.

His boxers were seriously tented, my breath getting heavier and heavier as I reached up and pulled them down too. Fuck, I actually licked my lips when I saw it, huge and full and straight and hard, large balls hanging down underneath it. I had been in locker rooms all the time growing up, but I had never seen anything like this. As much out of a sense of awe as because I knew it was what I had to do, I took it in my hand, marveling at how feminine my long fingers and bright red polish looked wrapped around his meat.

Cupping his testicles in my other hand, I slowly leaned in and kissed it. "That's a good girl. I knew you'd like this." I looked up to see the smile on his face. "As soon as I saw you walk into the cafeteria, the way you strode across the room, playing your sexy outfit for all it was worth, and when you fixed your lipstick, I knew."

I took a deep breath and slipped the bulbous purple head into my mouth, swirling my tongue around the soft flesh. "That's my girl, just like that." His voice was taking on a soothing tone and was helping me relax.

Taking him a little further into my mouth, I inhaled deeply, letting his musky aroma fill my senses. Shit, I was getting hard; I closed my eyes and kept going, one hand stroking the base of his erection while the other fondled his large, warm balls.

I knew what I liked girls to do to me and I began trying to emulate them, sliding the massive beast as far into my mouth as it would go and then taking it out, running my lips from its tip to its base, taking his balls in my mouth and sucking hard. I used both hands to massage the spit covered shaft while my lips and tongue teased his glans.

Pre-cum seeped into my mouth, and he moaned, softly at first and the louder and louder as I continued my assault. "You're loving this, aren't you?" His hands found the sides of my head. "You are such a cock whore." He moaned again.

I stopped. "Don't talk to me like that. It's bad enough what you're making me do. I don't need verbal abuse, too." There was fire in my words and in my eyes, but the lust in my heart knew it didn't matter what he said. I wouldn't stop. He was right, I did like this.

"I'm sorry, babe, some girls like that. I'll behave, but you are enjoying this just a little, aren't you?"

I didn't answer, I just took him as far in my mouth as I could and sucked hard, squeezing his balls, attacking his hot meat with a renewed fervor; he knew.

Stroking, bobbing, licking, sucking, traces of red lip stick up and down his cock, I did everything I could think of to bring him pleasure. When I sensed he was close, I even slid my hand between his legs and probed his ass. Using the spit dripping from his balls as lube, I pressed two fingers inside and found his prostate.

Pulling him out until just the head was in my mouth, I stroked his shaft with one hand while the fingers on the other pressed against the soft fleshy spot in his ass, "My god," he cried as his hands gripped my head, his body clenched, and his cock began to pulse, filling my mouth with warm bitter juice.

As he began to relax, I milked the last if his jiz into my mouth, twirling my tongue around his glans, relishing the taste on my tongue as I had never expected to. Leaning back on my heels, looking up at him with a wry smile, I opened my mouth to show him what I had done, closed it again and swallowed, licking my lips, and leaning forward to kiss the tip of his now flaccid warrior.

I offered Dean Wagner my hand and he helped me to my feet. Neither of us said a word as he pulled his pants up and I retrieved my blouse and jacket, refreshing my lip stick yet again, and turned to leave.

"Miss Wilson," he stopped me just as I reached the door.

"Yes?' I turned and met his gaze.

"I was thinking perhaps a weekly review of your progress might be in order?" It sounded like a request.

"Would that be a requirement?" I raised an eyebrow.

"No, I don't think so." He gave me a knowing smile.

I took my time, looking him over from top to bottom, he was a well-dressed, nice-looking man, maybe late fifties, and well respected, with an obvious fetish and a huge cock. I didn't know if he was married or much about him outside of our interactions at the school since I had come on board just after Christmas break.

I thought about the circumstance, what he had forced me to do, and how my reservations had so quickly turned into wild abandon. What I had done when he finished, showing off my prize, almost giddy looking for his approval. "Then I think I would like that very much." My smile matched his. "Next Monday then?" I winked and opened the door, leaving one very satisfied man in my wake.

I used my conference period to finish grading the papers my seniors had submitted and got similar receptions in my afternoon classes to the morning ones. I had the boys' rapt attention and was sure they didn't hear a word I said. Maybe I should tone it down a bit tomorrow.

"Nope, not a chance." I laughed to myself as I made my way back to Barrington. It was just too much fun, too exhilarating. And there was that meeting with Dean Wagner that had been so interesting.

Dinner at the school was less formal than breakfast and I was one of the few faculty members that lived on campus, so I had a table to myself. I was the only one that came to dinner dressed. I thought about it for a minute but remembered the rules had been specific; we were suspect to being judged whenever we were on campus, except for the two thirty-minute grace periods at the beginning and end of the school day, that, and I was enjoying myself more than I ever thought I would.

After dinner, I walked back to Barrington with a small group of my seniors, talking about the competition and them telling me how hot they all thought I was. I smiled and accepted their compliments, noticing that Mr. Simpson had a slight blush going on.

Most evenings I spent in the common room with the boys, providing ad hoc tutoring or watching the game de jour and yelling and screaming at how bad the officiating was. The sport or the teams didn't matter. It was just a release from the daily pressures of being a Wellington Man and subtle jab at the strict codes we asked them to live by.

I had changed into a pair of shorts and a t-shirt that was probably a little too tight, if I were being honest, and was sitting at a table in the back of the room re-reading 'Le Morte d'Arthur' for probably the fifth time, Arthur's battle with Mordred was one of my favorite passages in all of literature.

Ok, I was pretending to read Mallory's work. What I was really doing was going over my meeting with Dean Wagner in my head, trying to figure out what had happened and trying to understand what I had agreed to do it again. What was I thinking when I said yes?

I rationalized I hadn't had a choice, but I knew I had and that didn't explain why I had enjoyed it so much. Why had I showed him the cum in my mouth and made a show out of swallowing it like a porn star?

This whole dressing up thing, the rush of the male attention, the charge I got from the click of my heels, the feel of the color on my lips, and the delicate touch of my nylons, hell, even the small charge I got from my t-shirt being too tight, this was my crack, my heroin. I was getting addicted to the whole idea of Erica, and it was just day one.