Teacher's Challenge

"What was so wrong about it?" he kissed my cheek.

"I'm a man, you're a man, and I'm your teacher." I let out a long sigh.

"Ok, the student teacher thing, I get that," he turned me to face him, wrapping his arms loosely around my waist. "But you a man? I don't think so. For the past week, you have been the most feminine woman anybody on this campus has ever seen. You brought three suitcases of clothes and makeup back with you, you love being a woman. Tell me I'm wrong."

I couldn't.

"I'm sorry, Miss Wilson, you are not a man, not to me or anybody else at this school, anyway. And even if you were a man, so what? We're both old enough to make those decisions, right?" Dammit, he kissed me, and I melted into his arms, knowing what he said was true. The only part of me that anyone could construe as being a man was rock hard between us.

Taking my arms from around his neck, I reached down and took us both in my hands, fondling our members as I wrestled with my new reality. This was so wrong and so right. I just wanted what, what did I want? My mind lost in the too fresh memory of what we had done, it was spinning with the realization that I had wanted, had needed, to be taken like a woman. What I wanted was for him to take me again.

I turned and leaned against the wall of the shower, pushing my ass out, inviting him to use me.

"Are you sure about this, Miss Wilson?" his hands found my hips.

"Shut up and fuck me, Mr. Simpson." I closed my eyes and let out a loud moan as he pushed inside me again, losing myself in the carnal act, erupting under the warm spray as he filled me with his seed a second time.

I was surely going straight to hell, but oh my, what a trip it would be!

Waking up alone in my bed was a mix of relief and angst. Alan had stayed well past the shower, and we had done things to each other that only existed in my deepest, darkest fantasies. We had used and enjoyed each other over and over. Well, mostly he used me, and I loved every minute. If he had stayed, there would have been a genuine chance someone would have seen him leaving my apartment.

My angst centered on what our relationship was going to look like going forward. I knew all he had to do was ask and I would do it all over again.

I did my makeup, put my hair up in a ponytail, put on a cute romper Carol had picked out for me, and headed for breakfast. They set weekend meals up on a buffet system, letting students and what little faculty was on campus come and go as they pleased. I took Mallory with me to dissuade anyone from bothering me. I didn't really want to read as much as think about what I had gotten myself into.

Just a week ago, I was going out, full of determination and trepidation, dressed as a woman, to go shopping with Carol. Today, I was going out, my stomach and my ass full of a student's bodily fluids, dressed as a woman, trying to figure out what the hell had happened.

The rest of the weekend was relaxing. I spent some time at the pool and watched a baseball game with the guys in the common room. Mr. Simpson and I crossed paths a few times. Neither of us said anything about what had happened Friday night.

By Monday morning, I was believing all I had to worry about was my 'review' with Dean Wagner.

My homeroom class was filtering out when I noticed Mr. Simpson slipping into my room. He smiled and waved at me, purposely letting the rest of the students filter out of the room before he closed the door behind them.

"Can I help you Mr. Simpson? Don't you have somewhere you need to be?" I had a suspicion what was going on and couldn't believe he would try to pull something like this.

"I do and I need your help with that," he smiled, "I have a huge calculus test and I'm so distracted thinking about what we did, what would happen if anybody found out," the way he said it carried a very strong implied threat. "I just don't know what to do about this." He unzipped his pants and pulled his erection out of his pants.

"Really Alan? Here? Now?"

He just nodded. "Here. Now."

Fuck, this was ridiculous. I had gotten myself into this and didn't see a way out. I locked the door and dropped to my knees in front of him, taking him in my mouth and twirling my tongue around the head of his cock while my hand jerked him furiously. It didn't take but a few minutes before I felt him tensing, driving him down my throat. I squeezed his balls and let him empty them down my throat. Part of the problem was, I enjoyed it. I didn't want to think about all the other issues with what had just happened.

Kissing the tip of his softening member, I put it back in his pants and got to my feet. "Mr. Simpson, first, threats aren't really necessary. I believe we both enjoyed Friday evening and, second, this is neither the time nor place for this. If you're horny, let's please be more discreet, ok?"

"Yes, Miss Wilson and thank you for the, um, help," he grinned, turned, and left for his calculus class.

The rest of my morning was a nothing out of the ordinary, sophomore and freshman comp, senior classical lit, and then lunch, followed by my conference period, which meant I would be on my knees again, this time in Dean Wagner's office.

"Miss Wilson, I do believe you are beginning to enjoy our performance reviews, perhaps twice a week. Why don't you stop by on Wednesday as well and we'll see how it goes?"

I licked the last drops of cum from his cock and got to my feet. "If you feel it would help the situation, then I don't see why not." I sighed a heavy sigh and turned to leave.

My afternoon was totally unproductive. All I could think about was the extracurricular activities that seemed to be taking over my life, and how much I was starting to enjoy them. Mr. Simpson was in my last class, senior comp, and was, thankfully, a perfect gentleman. When the bell rang, I went straight to my room and took a long hot bath, skipping dinner and sequestering myself in my room.

Tuesday morning, I dressed as conservatively as my wardrobe would allow, which wasn't very, and did my best to not run into Mr. Simpson or Dean Wagner. I made it through the entire day and was starting to feel a little better, until I realized Mr. Simpson had stayed after the rest of the students had left.

"More math problems, Mr. Simpson?" I took a deep breath and looked at him.

"You might say that" he walked to the door and locked it.

"I thought we had an understanding." I leaned back against my desk.

"We do. This is much more discreet than last time, don't you think?"

"Alan, really, this is too risky," I made the mistake of licking my lips as he started to unzip his pants.

I took my time this time, relishing the feeling of him in my mouth, enjoying the feeling of him taking control and fucking my face, driving his cock down my throat, and holding it there while he spewed his seed into my stomach.

Fixing my makeup, I let Alan leave well before me to ease any suspicions. Of course, there would be none. It was common for faculty to have students in their rooms after the day for tutoring or counseling. Most of my concern was that it would be difficult to call what Mr. Simpson and I were doing either of those.

I passed coach Tanner in the hallway and got a very interesting look, or was it just that the gaudy makeup he and the rest of the coaches wore that made it look like that?

Wednesday, I sort of got a reprieve when Mr. Simpson gave me the day off. Of course, there was Dean Wagner to take care of, but I looked forward to that.

Thursday, the wheels came off. Alan stopped by my room on his way to breakfast for a quickie, but it was in my apartment, and I knew no one would see us. I think he got an extra jolt out of it because I was still in my underwear when he showed up.

It was lunch where things went sideways. I had just finished eating when my phone buzzed.

'Saturday 7:00. Don't be late' and an address. A video of Mr. Simpson face fucking me in my office followed the text.

I scanned the room furiously, looking for a clue who had sent me the message. Nothing.

"So, round two tomorrow night, just like last week?" it was Mr. Simpson.

"Sure, why the hell not?" I got up and left him standing there. My life ruined. Why not go out with a bang?

To say I was worthless the rest of the day and all-day Friday would be courteous; I was a basket case. I was looking forward to Alan fucking my brains out again just to take my mind off the fact that someone had video of him doing just that; it was ironic to the extreme.

When he finally knocked on my door, opened it and yanked him inside. "Erica, I just came to apologize. We don't..." I didn't let him finish his sentence. I pushed him against the wall and covered his lips with my own, driving my tongue deep into his mouth and running my hand straight to his crotch.

It would have been a fair assessment to say I raped him that night. The sex was raw and primal. I sucked him hard, and he fucked me like there was no tomorrow. I spewed my seed all over the both of us as we went at each other again and again. We fucked in my living room and in my bed, then in the shower, only to go back to my bed and do it again. When we were both so exhausted, we couldn't go on. I broke down in his arms and cried.

"Erica," he had never called me that before, "what's the matter?"

I showed him the text.

"Oh, any idea who?" he asked in a whisper, holding me while I continued to sob.

"I saw coach Tanner in the hall after you left that day. He looked at me funny, but with him, you can never tell, so not really. I'll just have to show up and see. I don't really have any choice; I could go to jail for what you and I have done."

"I won't let that happen; I promise. I'll tell them I forced you, I blackmailed you or something."

"No, this is on me. All I had to do was say no. And that would be so obvious. I'll go tomorrow and find out what whoever it is wants." I nestled in his arms and let him hold me. That's how we woke up the next morning and I wouldn't have wanted it any other way. Alan was a good man, and I was lucky to know him. Besides, the sex had truly been amazing.

We showered together and made love under the hot spray for what we believed to be the last time. It was slow and powerful, tender, and delicious; all the things it should be between lovers. He snuck out, and I followed him a few minutes later, making our separate ways to breakfast.

I spent the entire day organizing my class notes and preparing for whomever was going to replace me when this all came out. There was no way it wouldn't. At five, I showered and got ready, only to have my preparations interrupted by another text. It was a picture of me the day I had come back to campus wearing my shorts and a tank top with those four-inch heels I loved so much. Well, that made things easy.

I put my hair up in a high ponytail, grabbed my purse, and headed for my car.

Mr. Simpson stopped me outside the common room. "I did some checking. That address is coach Smithers. They all get together and play poker twice a month. I think they're all going to be there." The look on his face almost broke me. He really cared.

"I just hope they're not all in drag, I don't think I could handle that," we both laughed, "and thanks Alan, for everything." I gave him a peck on the cheek and went to face my fate.

As high school coaches went, they were well, high school coaches, but Wellington had the highest standards and the school expected them to set a good example, so the customary fat guy with tobacco stains on his shirt was nowhere to be found. Instead, there were fifteen very fit men from their early twenties, like me, to their late fifties, like Coach Tanner. Not a bad-looking bunch, especially now that the makeup was gone.

"Hey, you made it, great, so buy in is fifty bucks, Texas Hold'em friendly game. You're on table two over there with Smithers and Jackson. Winner, take all," coach Tanner smiled at me.

"Um, ok," I was dumbfounded, "I didn't bring any cash." I was sure he could read the confusion on my face.

"We got that covered for you." His smile turned into a devilish grin. "So, here's the deal. We've been talking about it and kind of feel you cost us, as a group, at least five thousand dollars. We were planning on winning the challenge, even convinced the seniors what it should be, thinking no one would go as far out as we planned, until your sweet ass showed up last week looking like a gaddamned supermodel. So that's about $300 each which, last time I checked, was the cost of a high-end blow job in Vergas. From what I saw, you are definitely high end."

I cut him off. "So, I play 'your game' tonight and what happens to that video? It just disappears forever?"

"Pretty much. I thought you'd figure it out, so what do you say? Play a little poker, suck a little cock, and all your problems go away."

I took a deep breath and shook my head. "Fuck, what the hell? Not like I really have a choice, is it? Deal the damned cards."

They were a fun group. The banter amongst them as the chips moved around the tables was funny and spirited. I quickly picked up on their personalities and, as a result, started winning a few hands. Every so often, one of them would ask me if I wanted to take a break and we would go off to a corner and I would get on my knees.

Smithers was first and I was surprised, the man was hung like a friggen horse, ten inches and thick as my wrist, I played with it, running my lips up and down the shaft, taking as much of the monster as I could I my mouth while I used both hands to stroke it up and down. Getting one of his balls into my mouth was an accomplishment. I worked on his shaft for ten minutes before he started to tense.

Taking the huge head in my mouth, flicking his glans with my tongue, I stroked as fast as I could with one hand while I gently squeeze his balls with the other. He exploded and I did my best but ended with thick white sticky mess running out my nose anyway. It was as wonderful as it was gross.

Licking the cum from my upper lip, I smiled up at him and went to wash my face.

A young first-year coach was next and under different circumstances, I might have dated him, but he was rough and rude, calling me a bitch and a cum-slut, and tasted like cigarettes. When he came, I almost spit it out, but thought better of it, swallowed, and went to get a shot of tequila from the small bar they had set up.

I could have sucked Beacham's cock all night. He was the strength and conditioning coach and looked like it, chiseled good looks that reminded me of Wesley Snipes in his prime. His cock was a thing of beauty. Not as big as Smithers, but still impressive. It fit in my mouth easily and felt so good when I took it all the way down my throat. He could have easily started face fucking me and I would have loved it, but he let me worship his manhood like a woman should, teasing it with kisses and licks, sucking on his large dark balls and loving everything about it. When he started to cum, I knew I had to taste it, so I pulled him out of my throat until just his head was in my mouth, taking the last few spurts on my tongue, it was better than I had imagined, rich and full. Like I said, I could have sucked his cock all night.

Someone at the other table went all in and three others called, when the cards were flipped, the three who had called were done and I spent the next twenty minutes on my knees letting them take their turns filling my throat with their hot juice before they headed home.

Tackman, the head rowing coach, was next, and I let him face fuck me, eight inches of beautiful thick meat driving in and out of my throat. God, it was wonderful. When he came, it felt like it was in quarts. I almost soiled my panties. "That was amazing." He smiled down at me as I kissed the tip of his cock.

"Anytime," I smiled up at him. I don't think he realized I was telling the truth.

Walker, the head athletic trainer, came so fast, I sucked him off twice just so he wouldn't get embarrassed in front of his friends. I think they all knew he had a small dick, but I did my best to make him feel like he was right there with Smithers and Beacham. The look on his face made my night.

We combined tables when we got down to the last six, and I discovered, to everyone's surprise, that I was among the chip-leaders. I didn't have delusions of winning, but I was doing better than anyone imagined.

One by one, the last few coaches lost to Tanner, each taking their turn with my mouth until it was just him and me. No one, especially me, expected me to be in the position. Tanner had twice as many chips as me and I knew my chances were next to zero, so I went all in before the flop with a pair of threes and beat his two pairs with three of a kind. That flipped the table, and I was now in the lead.

When all the cards were dealt, there were Jacks, a spade and a heart, and nines, a diamond and a heart, with the ten of hearts showing, the possibilities were endless, anything from the two pair showing up to a straight flush, and from the way he was playing, I figured Tanner had at least a jack, maybe two, so I fidgeted around and looked like I did not know what to do trying to lull him into going for it.

"All in." He took the bait. I smiled and called, flipping over my queen and king of hearts. Yeah, I was going to suck his cock just like I had sucked the fourteen before him, but I had beaten them all at their game and was going home with eight hundred dollars and that felt good.

Tanner had a nice cock, not overly large but bigger than average, and he had prepared for tonight. He smelled and tasted good, a little fruity. I took my time, making sure he got everything he expected from me. I teased and kissed his balls, sucking on them while I stroked his shaft. I took him all the way down my throat and held him there while I played with his ass; a little surprised that he let me.

I twirled my tongue around his soft head and bobbed up and down, listening for his moans and playing his responses, driving him to the edge again and again, until he was begging me to let him finish. It was easier than I thought it should be to press my fingers into his ass and massage his prostate. The moan I got in response told me he loved I had done it.

There was no stopping him this time, and I relented, letting him fill my mouth with his warm spunk. Milking every drop from his balls and rolling back on my heels, opening my mouth to show him my prize, I winked up at him and swallowed.

Tanner let me watch him delete the video as he walked me to my car, congratulating me on my win and thanking me for being such a good sport about the whole thing, like it had been some party game. I let him know in no uncertain terms that more than one coach had let me know they were uncomfortable with the whole thing, only going along because I seemed so willing. I let him know that two of them would testify to the blackmail; it would never happen again for any reason, or he was going down with me.

Of course, I was lying, but he didn't know that. I didn't wait around for any kind of response or apology. It would have been meaningless, anyway. I got in my car and left him standing there. How I was going to face any of them on Monday was something I was going to have to figure out.

Mr. Simpson was still up when I got back to Barrington, watching some infomercial in the common room; it was obvious he was waiting for me, so I joined him on the couch.

We sat in silence for a while as some guy espoused the virtue of some product neither of us would ever need. "So, all good?" He finally asked.

"As good as it can be, I guess. Tanner deleted the video, and I won eight hundred bucks." I smiled and leaned my head on his shoulder. "Thanks for waiting up for me, by the way."

"Anything else?" he wrapped his arm around me.