Teacher's Challenge

"Kind of discovered that when I went to college. You're number six but my first t-girl. By the way, I love the tits."

"I'm glad. I've gotten quite attached to them, too. Get it? Attached to them." Steve groaned. I laughed. He spooned behind me, making it obvious he was grabbing one of my tits with his hand. I smiled and drifted off to sleep.

Steve woke up with his morning wood buried in my throat as I sucked him for all he was worth. He returned the favor, and we got up and got dressed. My first true walk of shame, I was going home in the same clothes I had left in the night before. At least I could freshen up my makeup from the compact in my purse.

I kissed Steve goodbye and went to change so Carol and I could go see our parents.

This was my parents, my mom and dad. I didn't want to go for shock and awe like I would for a night out with Carol, so subdued makeup and a pair of jeans, tight but not too much. A delicate flouncy blouse and my favorite ankle boots. I looked at Carol. She nodded her approval.

"Let's go." I answered with feigned determination. The truth was, I was scared silly.

We met at our dad's favorite BBQ place to mitigate any fallout. It had worked for Carol, so why not?

Mostly, my parents looked confused when we walked up to the table. Hugs all around and we sat down. "I'm guessing you two have something to tell us." My dad wasn't one to mince words.

I started with the senior challenge and went from there, explaining how it had evolved rather quickly into an understanding that it was something far deeper than just trying to win some money. Everything about being a woman just clicked. It fit. It made me feel empowered like never before. It made me a better teacher, a better person.

When I explained that my dean and the entire hiring committee practically begged me to stay Miss Wilson, I think it clicked. Telling them about Ben would have been too much, so we just talked about what had happened during the past month and what my plans were going forward. I readily admitted that I had already talked to a surgeon and was going to get implants to replace my injections. I'd tell Ben he was giving me new boobs when I got back.

My dad was as excited as me when I told them about my contract. When I told them about how the boys in my dorm had said goodbye, he got misty eyed. My mom cried.

"So, Erica, I have to ask." My dad looked at Carol and then at me. "Not that it matters at this point, but boys or girls?"

"Would both be an issue?"

"Figures." he shook his head and laughed. As parents go, Carol and I got pretty lucky.

I called Ben as soon as Carol and I got back to her condo, filling him on last night with Steve and how well things had gone with my parents. I admitted I hadn't mentioned him specifically but had told my mom and dad I played on both sides of the fence.

"And now I need to worry about Susan Reeder, too. Great." He laughed. "When are you coming back? I kind of left my schedule clear for the next two weeks, hoping you and I could get to know each other a little better outside the bedroom. Maybe do some of that dating stuff boys and girls do."

"Why didn't you tell me?"

"I tried, but you said you had people you needed to talk to, so... How many more people are on your list?"

"None, really. And everybody I would want to spend time with has to work, so I could come home in the morning." 'Home.' I thought about the word and the image of the big house with the horse barn and the lake that it brought to my mind. I could feel myself glowing. My heart filling with an excitement I hadn't felt before.

"I'd like that." We talked for a few more minutes before we said our goodbyes. There were words on the tip of my tongue I had to swallow before they slipped out. It was too soon, much too soon for that.

"Ben?" Carol smiled at me.

"Yes." I smiled back.

"Little sister, you have got it bad. I need to meet this guy before you two elope, ok?"

I tried to form a protest, but there was nothing I could say. She was right, and I knew it. Alan had been right. I had fallen in love with Ben the moment he told me he had changed his mind about paying me to leave, that he wanted me to stay so he could get to know me. In my heart, I knew then.

"Go, just go. You're going to be insufferable if you stay here with me." Carol hugged me tight and helped me pack. Three hours later, Alfred was taking my bag out of my trunk and carrying it to the master bedroom while I sucked Ben's tonsils from his throat.

There was no doubt Ben was a little jealous of my tryst with Steve, and he made me pay for it. I wasn't complaining, but two nights in a row of that kind of pounding and I was going to have trouble sitting for a while.

I lay on my back, covered in sweat and cum, Ben's seed slowly oozing out of my ass, looking up into his blue eyes. "You feel better now?" I gave a soft laugh.

"Whoever did these, did a great job." He ignored my question and played with my boobs.

"She said my body would absorb the stuff she injected, and I'd have to keep getting them fixed, unless I got implants. But you can do that, right?"

"That is what I do." He smiled at me and gave the left one a gentle squeeze. "How serious are you?"

"I'm not doing anything for the next week or so." I smiled up at him.

The next morning, I was in his office for an examination, well, an official medical examination. He made a couple of calls and Wednesday afternoon; I woke up with nice modest implants, along with a redo on the injections. With the hormones he prescribed, by the time my body absorbed the injection, I should have nice full breasts about the same size as the ones I had now.

I spent the next ten days hanging out at the pool, letting Ben and Alfred pamper me while I recovered.

The next week was prepping for move-in by the new senior class. With 125 rooms to assign, taking into consideration all the requests from all the students and their families, not to mention making sure all the rooms had everything they were supposed to have and contacting maintenance to get any missing items replaced, plus preparing my lesson plans for the first week of the coming term, I was a busy girl.

Saturday move-in day was even more chaotic as move-out had been. Mostly because of the people that wouldn't have been happy even if they had picked out their own room and roommate. It wasn't the boys, it was the parents, mostly the moms, and it took all the diplomacy I had, plus two visits from Dean Wagner to get everything resolved, but by the time the bell sounded for the welcome dinner, all my boys had settled into their rooms, and all the parents had left.

Just like the class that had just left, I quickly fell in love with all my boys and they, me. It was going to be a good year. There were no more Alan Simpson's or poker nights with the coaches. Ben kept me busy claiming all my weekends and one or two nights a week. Occasionally, I was late to breakfast, which upset Dean Wagner, but he knew the reason and did his best to not make a big deal out of it.

For three more years, I was the proctor of the senior dorm. I may have cried harder when Mr. Weiss left than I had when Alan did. He turned into a wonderful young man, full of confidence and ambition. That cute little redhead he had been with at the dance his freshman year was there with his parents the day he moved out of Barrington.

"I'll never forget you, Miss Wilson" He had hugged me so hard I couldn't breathe.

"Nor I you, Arnold." It was the first time I had ever used his first name.

He saved some postage by putting his graduation announcement from Harvard in the same envelope as the save the date for his wedding. I was going to make sure I was at both.

Ben finally put his foot down and forced me to give up my proctor position by proposing to me. After three years of dating, it was time. I moved in with Ben and never looked back.

For Christmas that year, Ben gave me a vagina. Well, he really gave it to himself. He was the one that was going to be using it after all. I was going to take the summer term off, and Ben was going to show me as much of Europe as he could for our honeymoon. Ben and I were leaving right after Alan's graduation from Columbia. As valedictorian, he was going to be speaking, and I wouldn't miss that for the world.

Our wedding was amazing. Carol was my maid of honor, with Beth and Sue as bridesmaids. I had told my parents Ben was a doctor, but I hadn't told them exactly who he was. We got married on the same patio where Ben held his birthday parties. My dress was pearl white with lace and beadwork from my neck to my ankles and a detachable train that spread eight feet behind me. It was the Cinderella dress little girls dream about.

My dad walking me down the aisle, Ben standing there waiting for me. Alan next to him as his dad's best man, Rick and Beachman his groomsmen, with Carol, Sue and Beth on the other side. My husband-to-be's ex-wife was my bridesmaid, it was perfect.

At the reception, Alan introduced me to a feisty blonde named April. She was at Columbia with him and had been accepted into Harvard Law just as he had.

"We're too young to be grandmothers." Beth whispered over my shoulder.

"We've got a few years, I hope." I smiled at her. We watched together as Alan and April disappeared into the dancefloor. Ben grabbed me. The crowd on the dancefloor quickly enveloped us as it had them. I looked but couldn't find Carol and Sue. I smiled at the implications and focused my attentions on my new husband. We were the last ones on the dance floor when the band finally called it quits. The small crowd of remnants grumbling as Alfred and the hired staff herded them toward the front door where the poor valets were waiting to get them their cars. It had been a long night for everyone.

Believe it or not, Ben and I undressed, took a quick shower, and climbed into our huge bed and just went to sleep.

Years later, I sit in my office at Wellington, looking at the picture on my desk from the wedding reception. There are Ben and me, Alan and April, my mom and dad, my sister Carol, Sue Reeder, Rick, and Beachman. Beth is standing behind all of us like a protective mother.

Alan graduated with honors from Harvard, as did April. He's now a freshman US Senator and April is a district judge. My mom and dad are the same, just older and Carol, well, she quit her job and moved to the small town just down the road from Wellington, where she opened a consulting business working out of the house she shares with Sue.

Tanner and Beachman were still coaching at the school. They got married and moved in together. It didn't surprise anybody.

With me to take care of Ben, Beth finally found someone and remarried. Dean Wagner retired after their wedding, and they spend most of their time traveling. I'm pretty sure she has expanded her views on sex, if only a little.

For reasons I will never understand, the hiring committee asked me to take Dean Wagner's place, citing my ability to relate to the students. It was almost like being a proctor again, except now I had a thousand students to look after, not just 250.

"Dean Simpson, there's a student to see you. The head of the senior council." My executive assistant stuck her head in my door.

"Send him in Ellen."

"Mr. Simpson, how can I help you this afternoon?" I smiled at the young man. His blue eyes and chiseled good looks reminding me so much of his father and his grandfather.

"We've decided on the challenge, and I'd like to get your approval." I nodded. "We thought that since this is the one-hundred-fiftieth anniversary of the school, maybe we should go back to a challenge from the past. We want to challenge all the professors to cross dress for a month. Would that be, ok?"

"Mr. Simpson. I think that would be an excellent idea."

"Thanks Nana Erica, I mean Dean Simpson."

"You're most welcome, Eric. Now, don't you have a class?"

Maybe the coaches will have a chance this time.

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Thanks for reading. I hope you liked Erica's journey as much as I enjoyed putting it together. Please let me know what you thought by leaving me a comment