Teacher's Challenge

"Go ahead, just let Alfred know what you'd like, and he'll have the chef prepare it for you." Ben smiled at me, and I laughed.

"Did I say something funny?" Ben gave me a curious look.

"No, it's just the image that came to my mind. You, Alan, the way you guys look, this house, a butler named Alfred, come on, you are Batman and Robin, admit it?" Even Alfred laughed.

I trusted the chef; the fruit was fresh, and the omelet was delicious. I was just taking my last bite when I saw Ben look past me and raise an eyebrow. Alan's fingers brushed my shoulder, anyway. He sat across from me, and Alfred had his breakfast in front of him almost immediately. I guessed that if I were here for more than a day, I could expect the same treatment.

It was more difficult for Alan that it was for me, so, to vent his frustration, he went to swim some laps.

"Ben, I need to know, me and Alan. What happened? That could be very serious, yet you almost seemed to expect it, and last night openly encouraged it?"

"First, he's my son and just as guilty as you and I refuse to let him get hurt. Yes, I could have had you fired and arrested, but he really cares for you and would have considered it his fault. You're not much older than him and why destroy two lives that are just getting started for a poor decision? He thinks he seduced you, you know?"

I nodded.

"Second, consider the dynamic at Wellington: a thousand boys at any given time. It's just a fact of life that some will be gay or bisexual, that some will cross dress or be transgender, like you.

Statistically, those numbers are growing. We're not here to judge lifestyles. We are here to give our students the tools to succeed in life regardless of their sexual preferences - as long as they behave with decorum while they're here. What lesson would it teach them about acceptance and inclusion if we fired you for being bisexual and transgender?

Finally, I know me, and if Alan is anything like his father, his libido is huge." My face was immediately crimson. "So, well, let's just say it didn't surprise me once I saw you."

"He was my first." I sighed heavily.

"That I did not know." Ben leaned forward.

"And he did kind of seduce me. I was struggling with my 'reviews' with Wagner, and he was just so nice to me. He had taken all these pictures of me, showing how beautiful I am as Erica; it was so validating. And then the story he wrote, so beautiful and erotic; all I wanted was for someone to care for me that much. When I asked him, he just said yes."

"I never worked that hard to get a girl." Ben laughed, "But I've got to give him credit. It worked."

"He has really helped me in a lot of ways. He's a good man," I smiled at Ben. "You should be proud of him."

"More than he knows," Ben got up and did a cannonball almost on top of Alan. I just sat and watched as the two of them wrestled in the water.

I couldn't explain why I was being so open with Ben, I guess I saw a lot of his son in him and neither had been judgmental about my gender status at all which was kind of nice since I was just starting to get a grasp on the idea of being transgender instead of just a guy in a dress. It had hit home at Tony's when I told Carol, "I want to be 'that girl'."

Ben and Alan had found a basketball and were going at each other hard in the pool, so I found a chaise and laid out to soak up the sun. Arthur stopped by occasionally to remind me to turn over and to make sure I had everything I needed. I caught myself thinking how easy it would be to get used to this.

"Ok, hot stuff," the sting of someone snapping my ass with a towel jerked my mind from the sun induced semi-coma I had slipped into, "Alfred has lunch ready."

I squealed as I jumped up, rubbing the small welt on my butt cheek to find Ben grinning from ear to ear, a damp towel in his hand, it was a tossup as to which of the three of us was more surprised when I tackled him into the pool and dunked him. He quickly recovered, picking me up in his strong arms, our eyes locking onto each other for just a moment before he launched me into the deep end of the pool.

To his credit, he did hand me a nice fresh towel when I climbed out, laughing as I readjusted my tuck and dried myself off, making sure my boobs weren't hanging out of my top.

After lunch, Alfred shooed us away from the pool so preparations for the party could get underway. Alan gave me an odd look and disappeared. "Can I show you around?" Ben offered me his hand.

I let him help me up and followed along next to him as he led me from room to room, out through the garage to the horse barn and down the path through the trees to a small private lake with a gazebo. The old house was full of history. Four generations of Simpsons had made it their home, all of them having a single heir. It just seemed to happen that way.

The garage was a small museum of fabulous cars, some new and some so collectible that putting a value on them would be close to impossible. The horse barn was a fully functioning stud barn with some amazing stallions with incredible blood lines. With all the staff, this place was a small town, yet came across as almost quaint.

Ben sat on the bench in the gazebo and patted the space next to him. I sat and waited for him to say what he was going to say.

"Erica, I have a confession to make." He wasn't looking at me. "I wanted last night to happen, for you and Alan to have that closure," He took a deep breath. "There's a check in my office made out to Eric Wilson, two hundred and fifty thousand dollars. I was going to buy you off, pay you to go away." He didn't finish the thought.

"Was?"

"I changed my mind when I met you in Dean Wagner's office, the way you played the game with me; you're obviously very intelligent and just so damned beautiful." He turned toward me. "I spent Thursday checking up on you, not just your background, but spying on your classes to see how you interacted with the students, to see how you handled yourself in various situations, you are an excellent teacher, and when you got here Friday, well, the more I'm around you, the less I want you to go."

"Ben, what are you saying?"

"I see what Alan sees in you. I understand why he crossed that line. I've never met a woman like you, and that is exactly how I see you, even when you're adjusting your tuck." He laughed. I was speechless. "Whether you accept the contract we're going to offer you or not, I'd like to ask you to stay. As Erica. Let me get to know you."

"That could be a little awkward with Alan, don't you think?"

"We talked in the pool. You both know your relationship can't continue. Too many people already know as it is. He's going to Europe for six weeks with his mom after graduation and then to Georgetown and hopefully, you're going to stay at Wellington and continue to shape young minds." he reached out and put his hand on my arm.

"Wellington would hire a transgender teacher. Doesn't that kind of fly in their reputation for propriety?" I added air quotes.

"The diversity we have in our faculty would surprise you. I know for a fact that Rick is gay and probably Beachman, too. I think they have a thing going."

"Lucky them," I giggled.

"And you know that Sue Reeder is a lesbian, right?"

"I did not, and she's my date to the graduation dance. It does kind of explain some things though. So, what happens now?"

"First, you need to decide if this is permanent, so we know what name to put on the contract." He had the best smile. "And if it is, we need to do things to make it that way; I know a surgeon that can help you with things like that, and an excellent lawyer that can help with the legal stuff."

"That's pretty final. I'm not sure I'm ready just yet. I haven't even talked to my parents." I suddenly felt like I was in a tunnel with a freight train barreling down on me and no way to get out of its way. It was almost too much; I needed a distraction.

"I think you'll know your answer if Erica shows up for breakfast a week from Monday." He made it all sound so simple. "The rest is just details. Now come on, we've been gone a long time and I'll bet we've convinced Alan we've been doing more than just talking," he laughed.

How could he be so understanding? In the short time I had known him, I had opened myself up more to him more than anyone except my own sister and he had accepted all of it, all of me at face value, no judgement, no ridicule, just acceptance, and he wanted me.

What was it about him, maybe it was he looked so much like Alan, and I was transferring some of that closeness, maybe it was just that he was a genuinely good person that cared about others more than himself and I found that attractive, maybe it was fate or kismet and the die had already been cast, for whatever reason, I felt drawn to him?

"About that. You mentioned something about me proving my dedication to Wellington this weekend when we were in Dean Wagner's office." I licked my lips and smiled at him.

"You picked up on that, did you?" he smiled back.

"Like you said, I'm a pretty smart girl." my hand moved to his crotch. "And your friend tells me you didn't bring me down here just to talk." He smiled again as I slid from the bench to kneel in front of him, sliding his suit down his thighs. Even his cock looked like Alan's.

Ben was right, we needed to head back before people started looking for us, so I swallowed him whole, he moaned loudly as I looked up into his blue eyes, sliding slowly up his shaft, sucking hard creating a nice pop as he came free from my lips.

"Why don't you drive?" I winked at him. "We don't have much time."

He took my meaning and got to his feet, placing his hands on either side of my head, guiding his cock back between my eager lips, and began fucking my throat. Just like with Rick at the poker game, I enjoyed the feeling of being used more than I thought I should. It didn't take long for Ben to finish and the force with which his seed surged down my throat told me he had needed the release for a while.

"Somebody needed that." I kissed his softening member and smiled up at him.

"You have no idea." He laughed. "Alan's mom was so conservative with sex; once a week, if that much, 'man on top, get it over with' kind of girl. If she'd let me do that to her, we might still be married."

"Let me guess, you looked somewhere else, and she found out?"

"Worse than just that." He laughed as he pulled his swimsuit back up his muscled legs. "I got drunk at one of my birthday parties and she caught me and Rick in the hot tub." He gave me an odd look. "I told you about the dynamic at Wellington, well Rick and I met there, became fast friends, and were even roommates in college. Let's just say we didn't always use the second bedroom in our apartment. When I married Beth, he would occasionally help me vent my frustration. Most of the time with a quicky blow job kind of like what we just did. That night in the hot tub, things got out of hand. Beth never said a word, just packed up and left. I got the divorce papers three days later." He offered me his hand.

"Ouch," I grimaced as I got to my feet.

"Yeah, I could just never talk to her about what I wanted, and it wasn't just the sex. We probably never should have gotten married in the first place, but there was Alan." He let out a soft sigh.

"Well, Alan is an amazing young man. Even with the issues, you two did a good job with him."

"Thanks, we're both very proud. I don't think his mom needs to know the details of your relationship, but you are probably going to meet her tonight. You might even like her."

"I'll be on my best behavior, I promise," I laughed.

"Not all night, I hope," he gave me a devilish grin that made me blush, "what we did, you enjoy that, being taken like that?"

"I guess I do. Rick did that to me at the poker game, and it felt so out of control. That's when I decided I like giving blow jobs, and then Beachman, my god, he's hung." I laughed and blushed even harder. "Everything I've done as Erica has been breaking down a new boundary, and I've enjoyed almost all of it." I slipped my arm in his as we headed back up the path toward the barn and the house.

"Smart, funny, beautiful, enjoys giving head. I knew I liked you." He grinned at me as his hand slid into mine, our fingers interlaced. We walked the rest of the way without a word, my mind spinning with the implications of what Ben was saying and how he was treating me.

I knew I was going to end up in his bed tonight and just like everything else that had happened in the past three weeks, it was happening too fast, much too fast, and I liked it.

Alfred led me to the room he had moved my things to, where I took a quick shower and redid my makeup a little heavier for the party, opting to put my hair up, leaving my long neck exposed.

The dress I had brought for the party was perfect, a lacey red fit and flair cocktail dress with a scoop neck and flutter sleeves. It fell about midway up my thighs. The matching four-inch heels would help emphasize my long legs, the bright red polish on my nails and the crimson choker around my neck with the little heart dangling from it that matched my earrings, would be the perfect accent.

Of course, the flimsy satin and lace I wore underneath it was just for Ben, if things went like I hoped they would.

"So?" Alan caught me as I got to the bar to get a glass of wine. "You and my dad, down by the lake." He smirked, "What was that?"

"Probably not what you think." I took a sip and turned to face him. "He explained he was going to buy me off to get me to leave you alone. Didn't want us getting too serious, I guess."

"Were we?" the look on his face betrayed a hint of hope.

I just raised an eyebrow and took another sip of my wine.

"Yeah, I didn't really think so either, but it was a lot of fun, wasn't it?" His smirk turned into a smile.

"I honestly enjoyed every minute of my time with you, you helped me realize who I am, and I'll never forget that."

"You said he was going to..." Alan didn't finish the thought.

"He thinks I'm an excellent teacher and I think he likes me." As much as I tried not to smile, the blush that filled my cheeks told him exactly what I meant. "I've got a lot to figure out in the next week or so."

I asked him about his trip to Europe to change the subject and to get my mind on anything other than what we were talking about. It worked until I saw the hungry look that flashed across Ben's face when he saw me from across the room. "I am so fucked." I whispered under my breath.

"No, but from the way my dad just undressed you with his eyes, I like your chances." Alan was laughing at me. I guess I hadn't whispered as quietly as I thought.

Eventually, I made my way over to congratulate the birthday boy, giving him a friendly kiss on the cheek and leaving a bright red mark in its place. He smiled at me and paused just a minute before he used his napkin to erase the evidence before taking me to meet the other regents in attendance, most of whom were on the hiring committee.

It wasn't as difficult as I thought it would be to explain my situation. Man in a dress even though the challenge wasn't technically in effect. "Just be honest." Ben had said as we walked through the crowd to the first of the group, and I was. Explaining that the challenge had opened a lot of new doors for me, and I was trying to figure it all out.

I mentioned that the fact that the boys seemed to relate to me better as Miss Wilson was one of the bigger factors in whatever decision I made. That seemed to ease a few fears. It surprised me how open and accepting they all were. Most of them had been to Wellington and I guess the specters of their experimentation while at the school factored in their tolerance.

"Well, this must be the Miss Wilson everyone is talking about." I turned to see a stunning blonde with deep brown eyes smiling at Ben and me.

"And for several reasons, I'm sure." I winked and smiled back.

"Oh, Benjamin. I like this one." She offered me her hand. "Beth, Beth Simpson. Nice to meet you. I honestly have heard so much about you, and all of it is good. You have impressed many people and the rumors are quite true. You are a beautiful woman."

Beth's settlement in the divorce was significant, significant enough that she spent her time working for charities and travelling. Her charitable works, however, weren't just for show. She mentored at risk girls. She built housing with Habitat for Humanity. She even travelled to Africa to assist teaching villagers about things we take for granted, like feminine hygiene products.

She asked me about my choice to transition. Evidently everybody but me had already decided that is what I was going to do. We talked at length about the pros and cons. I admitted that in my situation, there didn't appear to be any cons other than my quickly fading reticence. Other girls that didn't have my support had it much tougher than I could imagine.

There was no judgement which surprised me. I wrongly assumed that with her opinions on sex, someone like me would be shunned in her world. The simple fact was, she didn't object to alternate lifestyles, she just couldn't be married to someone that embraced them as Ben had.

"You know, the occasional blow job was one thing, but having your best friend lay you out on the deck of the hot tub, fucking you like a cheap whore at your own birthday party, while you scream, 'Yes, fuck my sissy ass. Make me your bitch.' was over the line."

Well, I probably wouldn't be dating material either, at least not for Beth. I tried not to laugh at the image in forming in my head of Ben as a sissy.

"Oh, go ahead. It's funny now." She had caught me. We both burst out laughing.

I had pictured Ben in a lot of ways, especially since we took that walk to the dock, but never in my wildest did I Imagine something like that. Well, I may or may not have imagined him doing it to me.

The party died down, and I excused myself, wishing Ben happy birthday a second time and replacing the lipstick mark on his cheek he had wiped off earlier. This time, he left it. He found me about thirty minutes later, naked, in the hot tub, enjoying a bottle of wine I had taken from the bar.

Ben undressed and, pouring himself a glass of wine, joined me. It wasn't long before I was screaming the exact same things he had screamed for Rick.

"So, Beth gave you details?" He leaned down and kissed me hard as he pulsed inside me. It's so hard to laugh and orgasm at the same time.

It was similar, but different waking up in Ben's arms the next morning. He was so much like his son, but the taboo was different: fucking the man controlling my job versus one of my students. As good as Alan was, Ben knew things about pleasing a woman like me that a boy like Alan couldn't possibly know. Compared to his father, Alan was just that, a boy.

I woke up to Ben pressing into me. Pulling my leg up to my chest, I let him in. "My god, you're going to kill me with that thing." I moaned as he filled my ass with his cock again.

"I can stop." He chuckled and leaned down to kiss my cheek.

"Nah, then I'd have to hurt you. There'd be blood, and I'd get fired. I think you should just keep fucking me."

"Yes, ma'am." He drove his cock balls deep inside me. His moan was louder than mine, but just barely.

We showered together, and of course; he took me again. I had thought Alan had sexual stamina. Ben was a god.

Arthur was a magician. Once again, he had moved my suitcase and clothes to the room I was sleeping in. Even setting my makeup out on the vanity. Whatever they paid him, it wasn't enough.

It surprised me to see Beth at breakfast, but she didn't seem to surprise at all to see me, even when I showed up with Ben, glowing like a woman that had someone had seriously fucked.