Teacher's Challenge

"Yeah, Beacham and Tackman are gods, and that new guy is a jerk and smokes too much." I paused. "And just so you know, I'm not sucking any more cocks for a few days." I kissed him on the cheek and headed for bed.

I lay in the darkness thinking about the past week. It had been a hell of a ride and I had two more to go. I still had to figure out how to tell Carol about everything that had been going on and still didn't know what to do about Steve. He was still texting me a few times a week, trying to get info on Erica. I finally closed my eyes, and it occurred to me that the coaches had taken their time planning tonight. Every one of them had given me days' worth of cum. I did the math and calculated that I probably had well over a cup of semen in my stomach. That and with the eight hundred dollars in my purse, it hadn't been a terrible night after all. "What a slut." I smiled to myself, rolled over, and went to sleep.

I slept in on Sunday, waking up just in time to get dressed and make it to the dining hall before they pulled lunch. I made a sandwich and just started walking around campus, ending up down by the river at the rowing shed. There were a couple of singles out on the water; it was like a painting, so serene, so beautiful.

"I love just watching them sometimes, gliding through the water like that; It's just so peaceful." Coach Tackman had taken the thought straight from my mind.

I turned and smiled at him. "I was just thinking the same thing."

"You ever tried it, it is a great workout and very therapeutic," he gave me a crooked grin, "you look like you've got a lot on your mind."

"Just everything that has happened since I started this damned challenge." I took the last bit of my sandwich and tossed the napkin in the trash or tried to, anyway.

"You do know we get weekends off." He bent down and picked it up for me.

"Except I'm a proctor for the senior dorm. The council all lives on my floor, and I can really use that money; I've got a ton of student debt." I gave a heavy sigh.

"Come on." he took my arm and started leading me to the barn.

"No, I don't think so," I pulled free. "Last night was a onetime thing." I turned away.

"Listen, I heard you tell Tanner off after the party. He told us if you showed up, it was because you wanted to. None of us knew anything about any video; most of the guys just think you're...," his face turned bright red.

"A huge slut," I finished the sentence for him, "to be honest, they're not completely wrong."

It was my turn to blush. "I just never thought it would turn into something like last night."

He let it go. "I just thought you might like to go rowing with me, but I need some help to get a training two in the water." He turned and moved toward the barn, this time letting me follow if I wanted.

It took some instruction, but we didn't tip over and had a great time rowing down the river and back. I didn't think about anything but my stroke, matching my technique to his and letting my mind wander. The problems I had been running over and over in my mind floating off into the thin wake left behind us.

When we got back to the dock, I was both tired and elated. My mind hadn't been this clear since Dean Wagner had stuck his cock in my mouth for the first time.

We put the boat back on the rack and I waited while Rick locked up the barn. "A burden shared gets lighter, just like the boat. Tony's? My treat." He smiled at me. Tony's was a small local Italian place with wonderful pizza a mile or two from the school.

We sat and ate and tentatively at first. I laid out everything that had happened. The challenge: Carol, Steve, Dean Wagner, Mr. Simpson and the video Tanner had taken. I even told him how much I enjoyed living as a woman; all of it, the clothes, the way men looked at me, the way I felt when I looked at myself in the mirror, admitting that some of the sex had been very nice, ultimately confessing for the first time that I wasn't sure I was going to go back after the challenge was over. With everything that was going on, that scared me to death.

I left out how much I had enjoyed giving him his blow job and thought better of letting him know about the dream that had woken me up early this morning, the dream of me laid across my bed, cum spewing from my cock, with him face fucking me while Beacham drove his massive shaft into my ass.

We finished our meal in silence, sharing a tiramisu, and Rick took me back to Barrington before heading home himself.

"Hey," he stopped me just as I was getting out of his car. "I'll take care of Tanner and the other coaches. If any of them give you any crap, just let me know and I'll put a stop to it."

"Thanks," I smiled and nodded.

"And as for young Mr. Simpson and the other stuff, I strongly suggest you two come clean with his father before things get any worse. He'll understand and will help you; I promise."

"That one I'll have to think about, but thanks, thanks for everything." I felt better than I had since this whole thing started.

I got a weak smile from Mr. Simpson as I passed the common room, gave him a small wave, and just went to my room, taking a nice hot batch before I crawled into bed and this time, openly fantasized about the two coaches tag teaming me into submission. The pool of sticky juice on my stomach and chest was impressive.

As if to hit reset, I chose the same suit I had worn the first day of the challenge Monday morning, similarly relishing the click of my heels on the pavement and the hardwood of the dining hall, noting how the boys ogled me and the coaches in their gaudy makeup and outfits, did their best not to look at me at all. With my confidence returning, I set my briefcase by my seat and went to the buffet to make my plate.

"Hey, what Tanner did to you, that was messed up, you know." I felt Beacham's massive presence behind me. "Rick told us all about it this morning at the coaches' meeting and everybody's pissed at Tanner." He patted me on the shoulder. "Just know, we all got your back, and I mean that. You need anything. Just let me or Rick know."

"Thanks." I never turned around. I just got my food and went back to my table. It was all I could do to not press my ass into his crotch and grind right there.

The rest of the day went as expected. My classes were wonderful. I was back on track, sitting on the edge of my desk, letting them try to look up my skirt and loving every minute. A few of the boys even mentioned that it was 'nice to have me back.'

I made up some excuse about a family issue. That was enough. Of course, there was my performance review with Dean Wagner, which went about as expected. With what I had done with the coaches, deep throating the Dean was easy and he took note, "You've been practicing, I like that."

I just smiled, got to my feet, and told him I'd see him Wednesday.

I recognized the laugh as soon as I reached the third floor, Carol was holding court in the common room, surrounded by all my seniors, telling stories about the two of us growing up together, I would have rather have them walk in on me giving someone a blow job than letting my older sister loose on them unsupervised.

"Erica," she screamed and ran across the room. "I thought you had died or something, but these nice young men told me you have just been busy. They also seem to think you have this competition thing in the bag."

"I'm glad to hear that. Now, what lies have you been filling their heads with?" I wrapped her in a big hug. Thirty minutes later, I was in Tony's for the second day in a row detailing the adventures of the past two weeks, only this time, I was like a warrior telling the tale of my epic battles.

Carol's reaction was a mix of pride, amazement, shock, and horror. "So, to recap, your boss pretty much forces you to suck him off twice a week and you like it, you're fucking young Mr. Simpson which is totally hot and totally unethical if not illegal, gave fifteen blow jobs Saturday night at a poker game, want a repeat performance with two of them, and fantasize about those two men spit roasting you, is that about, right?"

I nodded sheepishly and took a sip of my wine.

"And what happens when the challenge is over, and you have to go back to being Eric?"

"That's the thing, Carol. I don't think I want to."

"So, you want to just keep whoring around like this? You know that's a terrible idea, don't you?"

"No, I mean yes, I mean, yes, I know it's a terrible idea. Things would have to be different and it's honestly not the sex, well, not just the sex." I blushed. "I like who I see in the mirror. I love how people have been interacting with me for the past couple of weeks and I totally understand why you always look like a million bucks, where you get your confidence; I want that, too. I want to be 'that girl'."

"I have to admit, as much as I love Eric, Erica is a lot more fun." we both laughed at how absurd the situation had become. We talked about what it would really mean, how we thought our parents would take it. Carol brought up things I had yet to think about: surgeries, medications, legal issues; as usual, I had only seen the goal where my big sister saw the details needed to get there.

Carol spent the night sleeping with me, or staying up way too late with me, chatting about stuff until the wee hours. Bleary-eyed, she joined me for breakfast before she headed back home.

The rest of the day was as normal as any I had had since the challenge started, ending with Mr. Simpson walking me back to Barrington and slipping into my apartment where I pinned him to the door as soon as it closed, kissed him passionately, and started undressing him, dropping to my knees and looking up into his crystal blue eyes, "I never got to thank you for waiting up for me Saturday night." I smiled as my hands wrapped around his hardening erection.

Just like Dean Wagner, Alan enjoyed my newfound ability to take him all the way down my throat. I fondled his balls, licked, and sucked and caressed his shaft, letting him take control and drive his own pleasure as he thrust into my throat until he exploded.

We left a trail of clothes to my bed where we spent the afternoon lost in a carnal wonderland only limited by our lust and imagination and the incredible stamina of my nineteen-year-old lover.

"My dad wants to meet you." He whispered as he drew intricate designs in the mix of cum and sweat on my stomach and chest.

"He knows about us?" I felt a knot the size of New Jersey building in my stomach.

"Not specifically, but he knows something. He and coach Tackman are good friends." I relaxed a little, confident that Rick hadn't totally thrown me under the bus.

"So, when does this happen?"

"He wants you to come home with me this weekend. He's having a gigantic birthday party. You'll need clothes for Friday night, Saturday by the pool, and the party Saturday night. We'll come back Sunday after breakfast."

"I'm assuming he wants to meet Erica, not Eric." I took his sticky fingers and licked them clean as I got up to go to the bathroom and clean up.

"To be honest, I don't think he believes how convincing you are, and I might have talked about you a bit too much the last time I was home."

"Well, come fuck me in the shower and make it up to me. I'm not worrying about any of this anymore. Either I am going to hell or prison, or both." I laughed as I bent over and let out a deep sigh as he filled my ass with his cock.

Dean Wagner's receptionist wasn't at her desk when I arrived for my 'review,' so I knocked and just let myself in. "Oh dear, Mr. Wilson, I'm sorry I didn't get word to you. We will need to reschedule our meeting. I had an unexpected visitor. Tomorrow, same time?" he smiled at me.

It struck me as odd that he called me "Mr." No one had done that since the challenge started.

I recognized his visitor immediately, except for the obvious age difference Dr. Simpson and the young Mr. Simpson I had been fucking were identical.

"That would be fine, Dean Wagner, and Dr. Simpson. I would have to be blind not to recognize you. Your son is one of my favorite students. Whatever he does for a career, I hope he continues to write. He is incredibly talented." I smiled.

"My son is gifted in many things." The twinkle in his eye and the sly grin that accompanied his words told me he knew everything.

"I've come to understand that about him. He has an amazing attention to detail and is very thorough." I smiled at Dr. Simpson. Dean Wagner might as well not have been in the room at that moment.

"He speaks highly of you as well. In fact, so does Rick Tackman. I think you have an admirer. Just be careful if he offers to take you rowing." He laughed. "He used that technique on all the girls in college."

"Rick spoke to you about me?"

"We were at Wellington together, and them Columbia; we're good friends. He is as impressed with you as my son seems to be. In fact, that's why I came to see Dean Wagner. Rick said something about you being under administrative review pending the offer of your permanent contract. I'm on the hiring committee for the regents and thought I should investigate to make sure what he and my son were reporting wasn't slanted by any personal bias and that this review process was warranted." There was that grin again.

"I think administrative review is too strong a term, don't you agree, Dean Wagner?" I looked at the dean, sensing that I had a new and powerful ally in Dr. Simpson. "He has indeed taken a very intimate interest in my success at Wellington and assures me that the reviews are an informality. Like you, he wants to make sure that Wellington gets only the best. I think he would agree our review sessions have produced some very inspiring results. I just hope I have been properly exhibiting my dedication." Dean Wagner blushed; the innuendo was so thick in the room you could see it. Now, just how far did I want to push this?

"I actually enjoy some aspects of our review sessions very much and would hope that once my position becomes permanent, I can continue to count on Dean Wagner for his exceptional mentorship." I winked at Dean Wagner and smiled at Dr. Simpson.

"Just one more small thing, you are Eric Wilson, age 24, Master's in Education from Southwestern, is that correct?'

"Well, Dr. Simpson, for the next week and a half, I'm Erica Wilson, but the rest of that information is correct."

"Just checking," he gave a small laugh, "Alan was absolutely correct. You make a beautiful woman. Perhaps this weekend at my party, you can tell me more about your dedication to Wellington." He got up to leave, offering me his hand, "I'll leave you two to your review." His blue eyes were looking into my soul. "I look forward to seeing you this weekend, Erica."

Did he just ask me to suck his cock at the party?

"What just happened here?" Dean Wagner seemed to have missed a lot of the subtext.

"If I'm not mistaken," I stepped slowly toward Dean Wagner, "he knows you've been coercing me to perform oral sex and had I not admitted I wasn't totally opposed to the idea, might have fired you on the spot; he is a regent on the hiring committee, right?"

I watched as his jaw dropped, the realization slowly dawning on his face that the power structure in the room had just flipped. "Now, fortunately for you, Gerald, I am a bit of a cock slut and yours is very nice. I think you are a good dean, so how about we do our review, and you take some time this afternoon to write that letter of recommendation and send it to Dr. Simpson? He'll tell me whether he got it when I see him this weekend. I'm sure he will."

I used my finger to close his mouth and dropped to my knees to take his cock from his pants. It took me a while to get him hard this time, but in a way that made it more fun when he came. Milking the last drop of his cum from his softening member, I gently put the little soldier away and got to my feet, leaning in, and kissing him hard, sharing his juice with him, smiling as he accepted it.

I called Carol and got her advice on what to pack, deciding on a pair of khaki shorts and a silk tank top with sandals for Friday night. It was the perfect choice. Dinner was just Alan, his father Ben, and me. We had a great time. Ben wanted to know everything about me, childhood, school and if my dressing had really been just for the challenge.

I told him everything, and they told me all about growing up as Wellington legacies. There was a lot of money in the Simpson family, but you would never know it from Ben and Alan.

"I got your recommendation from Wagner, and he says you're one of the best he's seen in a long time, how did he put it, 'male or female, missing out on the opportunity you represent to our current and future students would be a disservice to all of Wellington.'. It talks a lot to impress a man like him." He gave me that same sly grin that had greeted me in Wagner's office.

"That was too kind of him," I was grinning from ear to ear.

"There is one thing, however, if you're going to teach at Wellington, stop fucking your students." He smiled as he looked at me and then at Alan. "Yes, I know all about you two, you haven't been as discrete as you thought, now go have your last hurrah, but starting tomorrow morning, not even so much as a peck on the cheek, got it?"

I wasn't moving fast enough, so Alan picked me up, threw me over his shoulder, and carried me to his room, tossing me on his bed and diving in after me. We kissed and fondled each other. For the first time, Alan sucked my cock and even swallowed. Of course, I returned the favor twice and when he fucked me; it lasted forever. Knowing it was our last time together gave both of us an energy unlike any we had experienced.

I lost count of my orgasms and knew Alan came more than me, completed sated we lay in each other's arms in the hot tub behind the house, watching the clouds drift across the star filled sky, "I'm never going to forget you, you know that, right?" Alan took my hand in his.

"Nor I you, you have so many wonderful gifts, aside from this one." I slipped my hand from his and grabbed his cock under the water. "You are going to do great things. I'm glad I got to be your teacher." I nestled close to him and let him put his arm around me.

"You can't change back, you know that right, you're so much better as a woman, everybody knows it, and to be completely honest, I'd never have fucked Mr. Wilson." He laughed and kissed me on the top of my head.

"That would have been a loss of epic proportions, for both of us," I laughed with him.

We dried off and went back upstairs to make love for the last time, Alan took his time, worshiping every inch of my body, kissing, and sucking on my toes, my fingers, even my cock one more time, before he slowly took me, letting me feel every inch of his glorious cock as he slid in and out of my eager hole. When he came, I came with him, sliding from me, he lowered his lips to my stomach and licked up the mess I had left.

"Thank you, Erica," he whispered as snuggled behind me and we drifted off to sleep. My last act of defiance was to steal that last peck on the cheek as I left Alan sleeping the next morning.

Alfred had left my bag at the foot of Alan's bed and after the scavenger hunt to find my clothes I had lost during our marathon, I went to take a shower, and got dressed. Pulling my hair into a high ponytail, I slipped on the most conservative bikini I had, slip on sandals, and a thin coverup for hanging out by the pool.

Stopping just for a minute to look at myself in the mirror, I noticed for the first time that I had a nice, thin waist and slightly rounded hips. I wasn't what you would call an hourglass, but in the bikini, it was decidedly feminine.

I found Ben by the pool, enjoying a cup of coffee, and sat down next to him. "Good morning miss," his butler walked up to the table just as I sat down.