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Teacher's Crossdressing Challenge PART 3
🕑 Added 2022-09-19 17:00:07 +0000 UTC"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.
"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.
