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Teacher's Crossdressing Challenge PART 1
🕑 Added 2022-09-15 17:19:57 +0000 UTCThe Wellington Academy, I couldn't believe it, yes, I had my Master's in Education to go with my Bachelors in Rhetoric and Composition, but I was a first-year teacher with no classroom experience and Wellington was the most prestigious private school in a five-state area, I guess I nailed my teaching demonstration.
Wellington was a residential boy's school, offering a classic liberal arts education filled with things like Latin, Philosophy, and Classical Literature. The school operated a year-round program of four quarters with three weeks off between them. Setting the bar with the highest of academic standards. If you graduated from Wellington, you had a well-rounded education and you could think critically.
Having said all that, Wellington still felt the pressures of social awareness that permeated today's society. The staff or administration could not express any political or social bias; the goal of the school was to teach young minds how to think, not what to think.
With that awareness in mind, the administration let the students pick a topic for each month in the academic calendar; the administration encouraged the faculty to fit the topic into their classes to support the students' efforts to celebrate and understand that social issue.
To say the students did their best to push our buttons was an understatement. It all culminated with the famous senior challenge. The seniors would present ideas to the senior council, who would then choose, then issuing said challenge to the faculty. It ran the gamut, Olympic style sporting events, engineering challenges, arts, music, trivia competitions, even producing and presenting a play. This year, supposedly to promote cultural awareness, the students had challenged the entire faculty to cross dress for the entire month. Transgender awareness was an issue of growing importance, after all.
To sweeten the pot, the kids pitched in ten dollars each. With school matching the prize and the top five faculty members, as judged by the senior council, splitting the pot, the overall winner pocketing half, that was a ten-thousand-dollar payday, and I had a ton of student debt; whatever it took, I was all in.
"Carol, you have to help me," I was begging my older sister for help. "I don't have a clue what to do and that much money would be huge for me. You just have to."
I knew she was going to say yes just like I knew she loved hearing me beg, "Ok, Goldilocks, come see me for the weekend and we'll figure it out, but a whole month, that's going to be a challenge," she laughed, "see you Friday night girly girl." She hung up before I could respond.
Carol was right, a day or two would have been easy, a week doable, but a month? That was going to be tough. I figured if I came on strong, I would have an edge, but for that kind of money, others were going to go for it too and they would up their game to meet mine, so I would have to keep upping the ante, so to speak, or set the initial bar so high, no one could catch me and that meant passing completely day one, and looking damn hot, too.
"Send me your measurements" it was a text from Carol with a diagram of a woman's body with lines across the chest, waist, and hips to use as a guide.
I shook my head and let out a soft laugh, wondering if it was really going to be worth it. I mean, what if nobody else took the challenge, and I went all out for nothing? What if a simple skirt and some low heels would have been enough? I guess I was going to find out on Monday.
Friday afternoon, they read the official rules for the challenge; they would judge all time on campus except for thirty minutes at the start and end of the day and thirty minutes for participants to fine tune their appearance or change to go home. Unfortunately, I was a proctor for the senior dorm and lived on campus; it was an extra five hundred a month and included room and board. Most first-year teachers took the opportunity.
I still got the thirty minutes every morning and afternoon, but my time never ended. Especially with me living in the senior dorm, I was on display to the judges 24/7, shit.
The drive to Carol's wasn't a long one, but I was a bundle of nerves. I hadn't even packed a bag. The realization that I was effectively going to be a girl for the next four weeks weighing heavier and heavier on my mind with every mile I drove; but ten thousand dollars. Damn, that would go a long way, so I kept driving.
"Meet me at the mall. VS." another text from Carol. Shit, VS had to mean Victoria's Secret. She was going for the big guns right out of the bag. What was I getting myself into? The thought ran through my head like a freight train on steroids.
I thought about stopping to eat but knew I needed all the time I had to get ready, and figured that in the state my stomach was in, anything I ate would come right back up anyway, so again, I kept driving.
Five O'clock on the dot, I found Carol standing outside Victoria's Secret, huge smile on her face and a smoothie in her hand for me. "You're really going through with this little brother." She handed me the smoothie, I just nodded and took a long sip. There was rum in the smoothie. God, I loved my sister.
Next door to VS was a place called Accents Aesthetics. Clinic and Day Spa. Fortunately, that was our first stop. Carol admitted she had told me to meet her at VS as a joke. OK, sometimes I loved my sister. We both laughed, and I relaxed.
"Ok, Eric, here's the plan; I already got you some things from next door. They're in the bag. The ladies are going to give you a deluxe makeover and I won't lie. Some of it is going to hurt like hell, but it will all be worth it if you really want to win that money. You just have to trust me; I've spent my entire life trying to look better than everybody around me and I like to think I know what I'm doing."
I had to agree. Carol was a wonderful person and a better sister, but she had always been a diva. Everything she did, everywhere she went, she had to be perfect; she had to look perfect. If she could do half of what she did for herself for me, I would be golden; especially considering what she had to work with. I had inherited my mom's thin build, high cheekbones, and nice round butt, and kept myself in great shape.
"Alright," I took a deep breath, "let's do this." I raised my smoothie to hers and smiled. "For the grand prize." I laughed.
"For the grand prize." Carol answered as the ladies at the spa took me by the arm and led me to the back. I found out later, Carol was getting a full body massage while I was being tortured; full body wax, Brazilian, even my crack, my eyebrows plucked, my ears pierced and extension in my hair. Bright red polish on my nails and a crash course on how to do makeup. There was no time to play games, and I watched intently each step of the way, doing my best not to cry like a little girl as they ripped all my body hair out.
"Ok, little sister. This is the biggie. You need boobs for this to work. We have other options, but if you really want that prize, this is the way to go." Carol led me from the spa toward a sign that said Aesthetics Clinic.
"I called in a couple of favors, and they agreed to squeeze you in. Trust me." She squeezed my hand.
I had to fill out all kinds of forms, like I was seeing a doctor for the first time. Trusting Carol, I just initialed where they told me and signed in what seemed like a dozen places. One for said something about informed consent. I looked at Carol. She nodded. I signed.
"So, they custom fit breast forms or something?"
"Not exactly, but you're going to love the results."
"I need to confirm a few things before we begin." A woman in a lab coat walked in, more interested in the papers in her hand than me.
"Ok." This was odd.
"Please tell me why you're here." She finally looked up at me.
"Um, breasts." I answered meekly.
"And this is your signature on the consent form?"
"Yes, ma'am."
"Alright, let's see what we have here."
She measured me and drew circles on my chest, marking little Xs in a few places around my areolas.
"I can get you to a C cup. For anything larger, you would need implants and we don't do those here. We are strictly an outpatient clinic. Do you understand?"
I looked at Carol. She nodded. "Yes, ma'am."
Local anesthetic and I watched as the doctor injected something into my chest where she had marked the X's, enthralled as perfect perky breasts grew on my chest. It only took about thirty minutes.
"These are semi-permanent. If you want to keep them, you'll have to come in about every six months for a booster."
"Six months?" I looked at Carol.
"Grand prize, little sister, grand prize."
We left the mall just as it closed. I had chosen the simple white panties and bra from the bag. My other choices being black, red, and pink, three sets of panties with one matching bra in each color. Carol helped me into the cute slip dress and into the short heel sandals she had picked out for me to wear. The boobs nestled in my bra, jiggling as I moved, tugging softly at my chest, filling out my dress nicely.
My guy clothes in a bag, my wallet, keys, lipstick and compact in my new purse strung over my shoulder, and the soft click of my heels on the tile echoing through the emptying mall, I followed Carol out to our cars not believing what I had done.
"Tomorrow, shopping. Right now, you must be starving and probably need something stronger than that smoothie." Carol laughed.
I was too shell-shocked to answer, I just followed her and did my best not to notice all the looks I was getting from the people we passed, I knew if I thought about it, I would convince myself they could see right through me and were all laughing at me.
When one man caught my eye and commented, "damn, I bet you're worth the climb. Fuck, you are one hot bitch." I just started laughing. Yes, it had been rude, crude and totally inappropriate and his mom would have probably washed his mouth out of being so crass, but it was exactly what I needed to hear. "Fuck, I'm one hot bitch." I repeated to myself and quickened my step to catch up with Carol.
"Did you hear what that guy said about me?"
"Get used to it. He was right, you are totally hot. You might even be as hot as me." She laughed. "So, you going to be ok with this? It's not too late to change your mind."
"After everything I just went through. I mean, have they ever waxed you like that? They waxed my balls and ass crack for crissakes." I almost yelled, "I have never felt so violated." We both started laughing uncontrollably. "And besides, if I'm really that hot, that ten grand is all but mine; I just know it. Now, let's go eat. I'm starved."
That crass, rude comment from a total stranger had given me an unexpected confidence. I couldn't describe how I felt. I just knew what he had said was true.
Grangers Bar was our go to when I was home and tonight was no different. It was a family pub with excellent beer and better food. Carol and I were going over plans for tomorrow's shopping while we waited for our food.
The place was packed and in a normal world, I would have never in my wildest imagination ever walked in the door dressed like a woman. But I had committed. I had already been through the gauntlet and what could be worse than some strange lady pulling out all your pubes?
I grabbed a table the busboy had just cleaned, and Carol went to the bar to get us drinks. To say the two of us were attracting attention was a mild understatement. Guys were nudging their buddies and trying not to get caught looking; some were even flat out staring and the look on their faces was one I knew all too well. Carol and I were the hottest girls in the bar.
My stomach in my throat, I took a couple of deep breaths and I found some of my nerves, just enough to keep me from running out of the building. Less than five hours ago, I was one of them, a guy ogling hot women as I made my way into the mall to meet with Carol. What had happened in the short time since was changing me in ways I never expected.
I should have been in panic mode. I should have been trying to hide. Instead, I was enjoying the attention. I even caught myself playing with my hair and pretending not to look at Steve, my old darts partner from before I went off to college.
"I wonder if he has a clue?" the thought drifted through my mind just as he caught me looking and made his way across the bar. He arrived at the same time as Carol, and her being my sister, of course, he knew her.
"Carol, who's your friend?" He winked at me and turned to her.
"Steve, nice to see you." She gave him a quick hug. "This is my cousin Erica. She and Eric were actually born on the same day. Can't you see the family resemblance?" She set my beer and two tequila shots down. I downed one of the tequila shots and drained about half of my beer without thinking.
"Well, she got all the good looks." He laughed. "So, Erica, Eric, same birthday, that had to be fun growing up?" Steve's attention had turned to me, and Carol might as well as disappeared.
"You have no idea," I grinned and shot death stares at Carol.
"You in town for long?"
"Nope, just the weekend, Carol and I have a lot of catching up to do, shopping all day tomorrow, maybe a massage or a trip to the spa, you know girl stuff, then I'm headed back home Sunday." Carol tried not to laugh when I mentioned the spa.
"So, no time for me?" he gave me those big puppy dog eyes.
"I have to admit you are awful cute, but not this trip. Maybe next time I'm in town. Carol knows how to get in touch with you, right?" The fact was, his number had been on my phone longer than Carol's.
Steve snagged a pen from the waitress that walked up to our table and wrote his number on a napkin, anyway. "Well, now you do too, and don't make me track you down." He handed me the napkin and watched as I folder it neatly and put it in my purse. Winking at me again, he turned to go back to his buddies.
I had seen Steve work his magic a hundred times. He never asked a girl for their number, instead giving them his and they almost always called. I had to admit it had been fun flirting with him and him not recognizing me was the last piece of the puzzle; there was no doubt I could do this.
"Duuude, your cousin is hot. I can't believe you never set me up. I thought we were tight." A few smiley faces followed Steve's text.
"Cousin, which one? Male or female? LOL" I replied. There was no doubt about Steve's sexuality. Possibly half the girls in town could testify to that, but he would expect the barb.
"Seriously, Erica man, you gotta hook me up here, she's gorgeous," I caught him looking at me across the bar pretending not to notice and trying not to let him see I was on my phone, too.
"I'll see what I can do. I gotta warn you, she a little different from most girls." He has no clue, I thought to myself as I hit send.
"No kidding, man. She's better looking than Carol. Thanks. I'll owe you one if she calls me."
"What are you doing?" Carol could see the devilish grin on my face.
"Texting Steve. He's asking me to set him up with Erica." I handed her the phone. "This girl thing is fun." We both laughed.
We finished our sandwiches and our drinks, and I stopped to wave and wink at Steve on the way out of the pub, "I think I may have created a monster." Carol jabbed me in the shoulder, grabbing my arm and dragging me out the door.
Saturday was busier than I thought. We went back to the mall, to specialty shops, a few big box stores; dresses, jeans, shorts, business suits, pantsuits, skirts, blouses, shoes, swimsuits, bikinis of course, Carol wouldn't have it any other way, more lingerie, and more shoes, and some luggage to put it all in, by the time we got back to Carol's apartment, I was both exhausted and elated. My feet were killing me, but I had mastered the fine art of walking in four-inch heels with just the right amount of wiggle in my hips. Carol paid for everything.
We split a pizza and a bottle of wine and crashed.
I laid in bed running it all through my head, the spa/clinic, my boobs, Steve, and all that shopping. It might have been cheaper to just ask Carol for the money, but it wouldn't have been near as much fun.
Sunday morning, Carol helped me pack, I did my own makeup, picked out a nice tight pair of jeans, and a linen blouse that fit just right, unbuttoned just enough to give a flash of my bra from the right angle, and a pair of heels. Pulling on the killer leather jacket we had found at a secondhand store, my hair up in a high tight ponytail, I took a deep breath and grabbed my purse; Erica was ready for whatever came, or so I thought.
We loaded my car and went to a little outdoor café by the river for lunch and it all sank in as we sat there enjoying the unusually mild weather. "Carol, what am I doing? This is crazy." I took a large sip of my wine, noting the lipstick on the glass and admiring my bright red nails as I set the wine down.
"Oh, so now, after all my hard work, now you get cold feet?" The feigned indignation in her voice made me smile. "You are rocking this thing and if you don't win, I want to see whoever beats you."
"You really think..." my confidence was wavering.
She put her finger on my lips, "Duh, one of your best friends is texting you to set him up with, well, you. What do you think? And besides, you've got boobs now."
I thought about Steve and just laughed.
We talked about last-minute details; I was going to need to find a spa or salon in case my hair came back too fast and I needed another wax job. Carol promised they get easier, or maybe just to get another manicure and pedicure for the fun of it; that I had enjoyed.
We talked about the difference between sexy and slutty, and since I was teaching at an all-boys school, sexy could be my friend, where slutty would get me in serious trouble. That I understood, I had been a teen-aged boy and knew what they were like.
During the drive back to Wellington, I was a bundle of nerves. Everything that could go wrong with this ran through my mind. I was even freaking out about spraining my ankle in the heels I was going to be wearing. By the time I pulled into my spot, I was almost hyperventilating. The only thing that prevented me from backing out was me not having anything to change into or any way to get my makeup off, and as Carol had said, I had boobs now and that spelled commitment.
My first challenge was waiting for me as soon as I unloaded my car; the massive stairs up the Barrington Hall with three suitcases in four-inch heels.
"Can I help you, miss?" I turned to see Alan Simpson, one of my better students, walking up to the dorm.
"I would appreciate that very much," I smiled at him and nodded at my bags.
"Um, miss, this is a boy's dormitory. Are you sure you're in the right place?"
"Quite sure, Mr. Simpson, and by the way, how is the final draft of your paper coming? I am really looking forward to reading it."
"Mr. Wilson, is that really you?" His jaw literally dropped open.
"I guess it will be Miss Wilson for the next month, won't it?" I smiled as I watched him try to regain his composure. "Now, about these bags. Do you think you can help me get them up to my room?"
It was one of my favorite things about Wellington, the boys that were here were all good kids, or at least trying to be. Their parents paid a ton for their spot, and it was an unwritten understanding that part of the education was how to behave. Classes in etiquette and decorum were mandatory. So, it didn't surprise me when Alan grabbed the two larger bags and headed up the stairs. I took the small one and followed him.
Barrington Hall was the original dorm for the school and was over a hundred years old. My heels clicked on the old hardwood floors as we made our way from the elevator to my apartment, I reveled in the looks I got and the slow recognition that spread across the faces of my boys as Alan and I made our way down the hall.
"Mr. Simpson, thank you for your help. Can you do me a favor and gather the boys in the common room? Based on the looks I've been getting; I think a chat might be in order." I smiled and dug my keys out of my purse.
"Yes, sir, I mean ma'am, I mean..." His face was beet red. "I'll take care of it." He turned and practically ran down the hall.
I took my time unpacking and reorganizing my closet, even laying out the dark gray pins stripe suit I had planned for tomorrow. Carol had agreed that going big day one was the right idea, and this suit was sexy as hell. It fit like I painted it on, and the skirt hit that magic spot just before too short that would show off my legs for maximum effect. With what the five-inch heels did to my legs, the way they cut the jacket and with the right blouse, I was going to make an enormous splash.
There was always a game on in the common room, being May, it could be baseball, hockey, or basketball and regardless of who was playing, the boys were all totally into whatever game it was so the silence that greeted me as I walked in was a surprise. It was occurring to me that when the boys had come up with this idea, they might not have expected anyone to take it to this level.
"So, I'm guessing Mr. Simpson was kind enough to fill you in, so," I did a slow turn, "you guys think I have a chance of winning this thing?"
I spent the next thirty minutes answering questions. "Yes, it's really me. No, I will not prove it." Ok, so not all the boys were total gentlemen, yet.
I told them about my sister and showed a few pictures we had taken while out shopping. The consensus was, I had it in the bag.
With the Q&A over, I settled in with my boys and watched as the Red Sox scored five in the bottom of the ninth to send the Yankees back to New York with another loss, fully aware of the not totally appropriate looks I was getting from some of them, especially Mr. Simpson.
Monday morning started with a nice, hot shower. I may or may not have spent a little longer than usual washing my chest. Lotion and then my panties, garter belt and stockings, relishing the feeling of the nylon sliding up my smooth legs. If I wasn't careful, I was going to have to jack off just to finish getting dressed. I flicked the tip of my erection with my finger, and he softened, giving me the chance to tuck him away. I slipped on my bra; I had chosen a lacey black one specifically, so it would show through the flimsy white silk blouse I was going to wear with my suit.
I stopped to admire myself in the mirror for a minute, snapping a picture with my phone. The sultry look on my face as the tip of my tongue caressed my upper lip was too hot. My blouse unbuttoned probably one button too far, I slipped on my skirt, smoothing it against my body and turning to admire the feminine form it was covering, noting that if I wasn't careful, the top of my stockings just might peek out: perfect. I smiled at my reflection and pulled on the jacket for the suit, buttoning the button to accent my bust.
Checking my hair and makeup one last time, stepping into my heels, admiring what the five-inch stilettos did to my calves and ass, grabbing my purse and my briefcase, I took a deep breath and headed to the cafeteria for breakfast and my big reveal.
The walk across campus was surreal. Everyone I passed did a double take. Some stopped to make sure I wasn't lost, and a few openly flirted with me. My heels clicked on the cement, and I added a little more swish to my hips, a strange feeling of confidence filling me; I was loving this.
Breakfast at Wellington also served as a venue for general announcements and dissemination of other important information, so all students and faculty were required to attend. It was the official start of the Wellington Day. This day was a bit more festive than most, as all the teachers taking part in the challenge were showing their stuff for the first time.
There were guys in skirts, I had expected that, many had obviously gotten outside help just as I had and looked pretty good, the coaches went for the absurd, outlandish wigs, huge fake boobs, and overdone makeup, only a few of us had swung for the fences. With Carol's help, I was prepared for that too.
Even Ms. Reeder, the sole female on the faculty, had stepped up. She was now sporting a serious pompadour and a couple of fake tattoos to go with her rolled-up shirtsleeves and biker boots. She looked like she had stepped out of a poster for an old Jimmy Dean movie.
What I wasn't prepared for was the reaction of the students, word had spread quickly about the blonde bombshell that had come home to Barrington Hall last night and while I had gotten a taste of what male attention felt like, Steve coming on to me was nothing compared to a thousand hormone fueled teenage boys and the way they stared at me as I walked across the cafeteria to my seat at the faculty table, each one undressing me in their mind, the click, click, click of my heels echoing through the room as it slowly fell silent.
The confidence that had been growing as I crossed the campus reached critical mass when I arrived at my seat, I set down my briefcase, slipped off my jacket, I shook my hair loose, smoothed my skirt, and took my compact out of my purse, refreshing my bright red lipstick. Amid the audible sighs, someone fell out of their chair. Score one for Miss Wilson. I smiled as I sat down, making sure everyone saw me cross my legs. I was loving everything about this, absolutely everything.
Dean Wagner complimented everyone on the participation, recognizing the coaches for their contribution and admonishing the students that they had all been instructed in decorum and were expected to know how to treat a lady. That sent a ripple of laughter through the entire room. The rest of the announcements were normal, and our day began. For the first time since I started, no one was late to my first period class.
As Mr. Wilson, I had always taught from the blackboard, today I decided to push the envelope a little, taking a seat on my desk facing my students with my legs crossed as we continued our discussion of the Arthurian mythos in Mallory's 'Le Morte d'Arthur.'
I had every boy's undivided attention but wasn't sure just how much we really got done. The rest of my classes were the same, they all knew exactly who I was and what was going on, but I guess tight skirts, garters, stockings, high heels, and a hint of lace were just too much for the hormone overload that filled my classes.
It was a bit of a relief to sit by myself in my classroom grading mid-term creative writing assignments over my lunch break. As much fun as it was and as much as I was reveling in all the testosterone fueled attention, the downtime was nice. I was saving Mr. Simpson's paper for last. He had genuine talent, and I hoped wherever he ended up after he graduated, he would pursue his writing.
"Miss Wilson," I had quickly come to enjoy being called that. Arnold Weiss, one of the freshmen, was at my door.
"Yes Mr. Weiss?" How can I help you?" I gave him a smile and he seemed to relax.
"Um, Dean Wagner asked me to come ask you to meet him in his office," Mr. Weiss was a shy, awkward young man with serious potential to be a real lady killer if he ever figured out how cute he really was. Some girl was going to rock his world, sucking him off in the back seat of his dad's Buick, and it would be game on. I hoped I got to see the results of that transition one day.
"Thank you, Mr. Weiss. I'll head right over." I closed my laptop, pulled on my jacket, and checked my makeup, redoing my lipstick, as I followed him out the door.
"Dean Wagner, I was told you wanted to see me." I don't know why, really, but Dean Wagner intimidated the hell out of me. He was a nice man and a good boss, offering constructive guidance and helpful suggestions as I got my teaching legs under me. It was, well, he was just a big man, at least 6' 6" and probably close to 300 lbs. Most of the students referred to him as the gentle giant, but my gut told me there was something else under that kind demeanor. I just couldn't put a finger on it.
"Please come in and sit down. I guess it's Miss Wilson for the next few weeks," he emphasized 'Miss' and smiled at me. I relaxed. "You've really gone above and beyond on the challenge. You are all everyone is talking about. Even the coaches are taking a back seat." He looked at me a little sideways. "If it's not too personal, can I ask if this is something you have done before?"
"Um, no sir, I have an older sister, Carol, who's kind of a fashion diva, if you know what I mean. When I told her about the challenge, she was all over it. Most of this is her fault." I gave a weak laugh. "The first time I put anything like this on was Friday."
"Wow, well I think you have this I the bag, if you can keep it up." He smiled again, and I could have sworn he winked at me.
"You should see my closet. Carol made sure I was loaded for bear. So, is this what you wanted to talk about?" I was fidgeting nervously in my chair, unconsciously crossing and recrossing my legs.
"It's part of it, I guess," he got up and walked around in front of his desk, "I mean it exhibits your level of commitment to the Wellington culture, but I just wanted to touch base on how you felt you were doing, the committee will meet at the end of this term to consider making your position permanent."
"Well, frankly, I love it here. The boys are amazing, bright, eager to learn, and gentlemen to the man. The rest of the faculty is amazing, and even being a dorm proctor, well it gives me an insight into the students that has been invaluable, plus I get to talk about things that I love, we're doing the Arthur legend in literature right now." I had uncrossed my legs and leaned forward. I did love this job.
"That's good to hear. I am getting very positive feedback from the students I have talked with, and your peers agree you're a good fit." He sat back on his desk and spread his legs a bit. "I just need to write my recommendation and I think you can count on a very nice offer from the committee." His kind smile had turned into a leer.
"Thank you. From what you've said, can I expect a positive recommendation?"
"I think we can make that happen, if you're willing to show me the full extent of your dedication, that is." He licked his lips. "You make a stunning young woman, you know, and it's obvious you freshened your lipstick before you came to see me?"
"Dean Wagner, just what are you implying?" I knew what he wanted. My head was reeling with the thought, and from the way he had phrased it, my job was on the line; I was going to suck his cock and get a good recommendation or have my career ruined.
"I think you know very well, Miss Wilson. You do me a favor and I do you a favor. It's that simple." I could see the bulge growing in his crotch. "Now, don't you think this would be easier if you were on your knees right now?"
My mind raced through my options as I felt a lump in my throat. I did love my job and with all my student debt, didn't have enough resources to support myself if I lost it. I guessed I could move in with Carol for a while, but that wasn't the best option, and what kind of recommendation would I get if I said no?
I didn't have a choice. Sliding from the chair onto my knees, I looked up at Dean Wagner as he stepped toward me.
"I knew you'd see things my way." He stepped forward and unzipped his pants. "Take off your jacket and blouse. I'd hate for anything to get stained," he laughed. I did what he suggested, exposing my lacey black push-up bra and my ample breasts.
Tentatively, I reached up and unfastened his belt, my heart racing, my mind spinning. Was I really going to do this? What if I wasn't any good at it? Would he still give me a recommendation? What if I was too good at it? Would he expect me to do it again? The questions wouldn't stop. His belt came free, the button on his slacks slipped from the loop, and his pants fell to the floor.
His boxers were seriously tented, my breath getting heavier and heavier as I reached up and pulled them down too. Fuck, I actually licked my lips when I saw it, huge and full and straight and hard, large balls hanging down underneath it. I had been in locker rooms all the time growing up, but I had never seen anything like this. As much out of a sense of awe as because I knew it was what I had to do, I took it in my hand, marveling at how feminine my long fingers and bright red polish looked wrapped around his meat.
Cupping his testicles in my other hand, I slowly leaned in and kissed it. "That's a good girl. I knew you'd like this." I looked up to see the smile on his face. "As soon as I saw you walk into the cafeteria, the way you strode across the room, playing your sexy outfit for all it was worth, and when you fixed your lipstick, I knew."
I took a deep breath and slipped the bulbous purple head into my mouth, swirling my tongue around the soft flesh. "That's my girl, just like that." His voice was taking on a soothing tone and was helping me relax.
Taking him a little further into my mouth, I inhaled deeply, letting his musky aroma fill my senses. Shit, I was getting hard; I closed my eyes and kept going, one hand stroking the base of his erection while the other fondled his large, warm balls.
I knew what I liked girls to do to me and I began trying to emulate them, sliding the massive beast as far into my mouth as it would go and then taking it out, running my lips from its tip to its base, taking his balls in my mouth and sucking hard. I used both hands to massage the spit covered shaft while my lips and tongue teased his glans.
Pre-cum seeped into my mouth, and he moaned, softly at first and the louder and louder as I continued my assault. "You're loving this, aren't you?" His hands found the sides of my head. "You are such a cock whore." He moaned again.
I stopped. "Don't talk to me like that. It's bad enough what you're making me do. I don't need verbal abuse, too." There was fire in my words and in my eyes, but the lust in my heart knew it didn't matter what he said. I wouldn't stop. He was right, I did like this.
"I'm sorry, babe, some girls like that. I'll behave, but you are enjoying this just a little, aren't you?"
I didn't answer, I just took him as far in my mouth as I could and sucked hard, squeezing his balls, attacking his hot meat with a renewed fervor; he knew.
Stroking, bobbing, licking, sucking, traces of red lip stick up and down his cock, I did everything I could think of to bring him pleasure. When I sensed he was close, I even slid my hand between his legs and probed his ass. Using the spit dripping from his balls as lube, I pressed two fingers inside and found his prostate.
Pulling him out until just the head was in my mouth, I stroked his shaft with one hand while the fingers on the other pressed against the soft fleshy spot in his ass, "My god," he cried as his hands gripped my head, his body clenched, and his cock began to pulse, filling my mouth with warm bitter juice.
As he began to relax, I milked the last if his jiz into my mouth, twirling my tongue around his glans, relishing the taste on my tongue as I had never expected to. Leaning back on my heels, looking up at him with a wry smile, I opened my mouth to show him what I had done, closed it again and swallowed, licking my lips, and leaning forward to kiss the tip of his now flaccid warrior.
I offered Dean Wagner my hand and he helped me to my feet. Neither of us said a word as he pulled his pants up and I retrieved my blouse and jacket, refreshing my lip stick yet again, and turned to leave.
"Miss Wilson," he stopped me just as I reached the door.
"Yes?' I turned and met his gaze.
"I was thinking perhaps a weekly review of your progress might be in order?" It sounded like a request.
"Would that be a requirement?" I raised an eyebrow.
"No, I don't think so." He gave me a knowing smile.
I took my time, looking him over from top to bottom, he was a well-dressed, nice-looking man, maybe late fifties, and well respected, with an obvious fetish and a huge cock. I didn't know if he was married or much about him outside of our interactions at the school since I had come on board just after Christmas break.
I thought about the circumstance, what he had forced me to do, and how my reservations had so quickly turned into wild abandon. What I had done when he finished, showing off my prize, almost giddy looking for his approval. "Then I think I would like that very much." My smile matched his. "Next Monday then?" I winked and opened the door, leaving one very satisfied man in my wake.
I used my conference period to finish grading the papers my seniors had submitted and got similar receptions in my afternoon classes to the morning ones. I had the boys' rapt attention and was sure they didn't hear a word I said. Maybe I should tone it down a bit tomorrow.
"Nope, not a chance." I laughed to myself as I made my way back to Barrington. It was just too much fun, too exhilarating. And there was that meeting with Dean Wagner that had been so interesting.
Dinner at the school was less formal than breakfast and I was one of the few faculty members that lived on campus, so I had a table to myself. I was the only one that came to dinner dressed. I thought about it for a minute but remembered the rules had been specific; we were suspect to being judged whenever we were on campus, except for the two thirty-minute grace periods at the beginning and end of the school day, that, and I was enjoying myself more than I ever thought I would.
After dinner, I walked back to Barrington with a small group of my seniors, talking about the competition and them telling me how hot they all thought I was. I smiled and accepted their compliments, noticing that Mr. Simpson had a slight blush going on.
Most evenings I spent in the common room with the boys, providing ad hoc tutoring or watching the game de jour and yelling and screaming at how bad the officiating was. The sport or the teams didn't matter. It was just a release from the daily pressures of being a Wellington Man and subtle jab at the strict codes we asked them to live by.
I had changed into a pair of shorts and a t-shirt that was probably a little too tight, if I were being honest, and was sitting at a table in the back of the room re-reading 'Le Morte d'Arthur' for probably the fifth time, Arthur's battle with Mordred was one of my favorite passages in all of literature.
Ok, I was pretending to read Mallory's work. What I was really doing was going over my meeting with Dean Wagner in my head, trying to figure out what had happened and trying to understand what I had agreed to do it again. What was I thinking when I said yes?
I rationalized I hadn't had a choice, but I knew I had and that didn't explain why I had enjoyed it so much. Why had I showed him the cum in my mouth and made a show out of swallowing it like a porn star?
This whole dressing up thing, the rush of the male attention, the charge I got from the click of my heels, the feel of the color on my lips, and the delicate touch of my nylons, hell, even the small charge I got from my t-shirt being too tight, this was my crack, my heroin. I was getting addicted to the whole idea of Erica, and it was just day one.
