Training the Trainer Pt. 02

Part II - A Tough Day at School

ATTN: All characters are purely fictional. All characters are over the age of eighteen. This story contains themes of reluctance and non-consent.

As I'd made my way home the previous evening, I hadn't bothered looking in the duffle bag that Lauren and Sadie had left for me. Whatever was in there, Lauren's texts had made it clear that I was not going to enjoy it and I'd suffered enough humiliations for one day. From being blackmailed, to being dressed up like a girl, to being forced to suck Sean's cock with a vibrating butt plug shoved up my ass, it was all too much.

Sleep had proven to be elusive however, and I'd tossed and turned all night in my tiny little studio apartment. I woke up the next morning, tired, and feeling entirely defeated. A text message from Lauren was waiting for me on my phone.

"Good morning, my little sissy! Hope you're ready for a great day. Please bring everything that Sadie left for you in the duffel bag to school today. Don't leave a single thing behind. We're going to use ALL of it. Can't wait to see you, Kenzie! XOXO Mistress."

My heart sank. I turned to look over at the duffel bag in question, which I'd tossed by my apartment door. It wasn't really a question of whether I was going to do what she said, since Lauren had all the video she'd ever need to completely ruin my life. It was more a question of how bad things were going to get.

With a sigh, I threw on my usual attire for school, a pair of khaki pants, a polo, with sneakers, scooped up the duffel bag and headed to my car.

About forty-five minutes later I was sitting down in my office, the team training room, and trying to keep the fear from rising in my chest. I'd stuffed the duffel bag under my desk, to keep it out of sight, but I still had not looked at its contents. Somehow, knowing what was in there, would probably be worse, since it would tell me what I had in store for the day.

To my surprise, the morning was pretty quiet. First and second periods passed without much to note. I'd taped a sprained ankle for a kid who'd twisted it in gym glass, but apart from grading a few quizzes for my health class, nothing was out of the ordinary.

At least, not until my phone buzzed. It was a text from Lauren.

Hope your day is going well Kenzie! As I'm sure last night was overwhelming for you, you've undoubtedly removed your butt plug, like a naughty girl. Never fear! Sadie and I have provided you with a new one. Though, no lube. Please put it in, and be ready for surprise inspection. Do not open any of the other packages. XOXO Mistress.

My stomach did a somersault. A new plug? Other packages? What the fuck? Seems there was a lot of planning going into my humiliation. Lauren wasn't wrong either. I'd removed the aforementioned plug that had been so unceremoniously shoved inside me the night before. I'd taken it out as soon as I realized I was alone, and chucked it into one of the school dumpsters, as I'd walked unsteadily to the parking lot.

With shaking hands, I reached under my desk and unzipped the duffel bag. To my surprise, I found several smaller black plastic bags, like you might get if you ordered clothes online. I couldn't see in any of them. However, right on top, in a clear package wrapper, was unmistakably a butt plug. Though, this one was different. It seemed to be about 3-inches long, wide, with a small bulb shape and flared base, though there was another thin stretch of silicone that was clearly meant to loop around my cock and balls.

For a moment I weighed the pros and cons of not following directions, then I decided that while my life might be in shambles at the moment, not following Lauren's directions would make it much much worse. I quickly stepped into the team training room's private restroom and ... slid my pants down.

It was painfully obvious what the "no lube" comment meant. So, without much thought, I went to work, licking and spitting all over the business end of the plug. Then I took some of the hand soap in the bathroom, which worked surprisingly well, and added that to the mix. I used a bit of it on one finger to apply my makeshift lube to my asshole, feeling slightly awkward about fingering myself, then began to press it inside.

Two minutes of struggle later and I felt the plug slip in, to the base. It didn't feel like the plug from last night. It felt ... wider. It was more noticeable and there was more pressure. I was, however, thankful that it didn't penetrate me as deep as the previous one, though that was a minor consolation.

The pieces that wrapped around my cock and balls were, uncomfortable, to say the least, I still had my metal chastity cage on, but the silicone bands attached to the plug slide over it easily, to wrap around my based, and squeezed by balls, forcing them to stick out in front of me at a really awkward angle.

My work done, I pulled my pants up and headed back to my office. I wasn't sure when Lauren and Sadie intended to conduct their surprise inspection, but I would be ready.

Halfway through my fourth period health class, I got quite a surprise. I was mid-sentence, reviewing the bones of the human body, when suddenly the plug came alive in my ass. There was a low hum, followed by an intense pulsing sensation.

I actually jumped a bit when I felt it. Some of my students gave me surprised looks and I heard some faint whispering. What's that buzzing? Do you hear something? I decided I'd better keep teaching just to avoid my students jumping to any strange conclusions. As class went on, the intensity of the vibrations seemed to go up and down, but the pulsing only ever got stronger.

During one segment of the lesson, I was having trouble finishing my sentences, and had to tell everyone I was getting a bit of a headache. To make matters worse, the strange sensations from the night before were once again building in my ass.

At that moment, I happened to turn at just the right time to catch the faces of both Lauren and Sadie staring through the glass pane of my door. They were both smiling and the vibration and pulsing reached a fever pitch. I visibly stumbled and felt very light headed.

A few seconds later, both the vibration and pulsing ceased, and the girls were gone. I recovered and managed to look composed as the bell rang and class was dismissed.

Fifth period had just begun when my phone buzzed. Another text from Lauren.

"Hello Kenzie! Quite a show you were putting on while you were teaching. Very slutty. I'm sending you a little make-up tutorial. Please follow it best you can. Everything you'll need is in the duffle bag. Please also put on everything else in the duffel bag. Be sure to open every package. Spend fifth period getting ready and during class change, make your way to the boy's restroom, just outside the library before sixth period. XOXO Mistress"

A video link soon followed, for a basic makeup tutorial.

Fuck. Whatever the girls were planning, it was apparently time. With a real sense of dread, I grabbed the duffel bag and stepped back into the private restroom in the team room. As I began to open packages, my heart began to beat faster and faster. The first package wasn't really a surprise. As I tore the black opaque plastic away, I found a small make up kit. No surprise there.

Though, the next few packages had my heart hammering in my chest. As I tore the next plastic bag open, I was shocked to find it contained a matching set of lacy lingerie. High waisted black panties, with a similar bra that was quite revealing. As stunned as I was, I didn't have a lot of time, so I kept opening. Next came a pair of lacy black tights. Then a small white women's polo shirt, with the Westmill crest stitched on the breast.

Westmill was a fairly preppy school, so I knew it had to have come directly from the school store. Then, as I opened the next package, I was greeted by a plaid, black and white pleated skirt that, at a glance, was going to be ... short ... very short. Definitely not dress code. Finally, the package in the bottom of the bag revealed a pair of open toed, three inch blocky heels, in black.

I was in shock. If I put this on, I was going to look ... look like ... a schoolgirl. A subtly slutty schoolgirl at that. But there were only forty minutes left in fifth period, so that didn't leave me a lot of time to complain. It was obvious what Lauren was going for. She wanted me to show up looking like a little sissy schoolgirl, no doubt to further humiliate me. Well, it was either that, or being fired. Possibly even jail. Not much of a choice.

With five minutes to go before the bell, I was taking some experimental steps around my office, trying to get used to the heels. The fact they were only 3-inches was a godsend, as I wasn't shaking too much in them. Everything else was done, as well.

The make up tutorial had taken the most time, and I'd decided to do it before I put the outfit on, so as not to mess up the clothes. After about twenty minutes, more than a couple times watching the video, I looked ... decent. Like any other teenage girl. My cheeks were a bit flusher, my face looked to be glowing more, I had some darker eyelashes, and my lips were a deep shade of red. The tutorial had also shown me how to add some fake freckles, so my face now sported a nice little pattern of freckles.

The outfit had taken a lot less time. The panties and bra had gone one without issue, though I'd felt like an absolute bitch putting them on. I'd also noticed that my old underwear had a wet spot on the front that stuck to my chastity cage. That was strange, but I didn't have time to think it over.

After that, the tights had been a struggle, but eventually no real issue. Then the skirt, which was, as I suspected, far too short for dress code. It barely came down below my ass. Then white polo, which hugged my figure, but otherwise, was fine. Finally, the heels, which I was getting the hang of.

Confident that I wouldn't break an ankle, I stepped back into the bathroom and took a last look at my reflection. Unless you looked close ... real close ... I could have passed for any other senior girl at Westmill. Actually, I looked, well, cute. Very cute. That surprised me, though I had no idea why. I'd been told I looked like a girl all my life. Guess there was some real truth to that.

The bell ringing nearly scared me out of my skin, and brought me back to myself.

I walked out into the hall. The library was in the basement, just below the cafeteria, in the recesses of the building. With modern technology and a digital library online, almost nobody ventured down that way anymore. However, to get there, I'd have to walk through several very crowded halls, then down the stairwell, which this being right next to the cafeteria during the final lunch period of the day, meant it was going to be very busy.

Hesitantly, I started walking that way. The soft click of my heels on the floor made me flush almost immediately. Thankfully, I managed not to encounter any students until I rounded the corner onto M-Hall, which was the main math hallway. I froze. The hall was packed. Standing there, in that moment, I'm not sure what I expected to happen. Maybe for somebody to call me out, shout freak, yell my name, call the police. Who could say? But what did happen was less exciting. As I started walking again, I just kind of blended in with the crowd.

When I thought about it, it shouldn't really be a shock, should it? I mean, even I thought I looked like a high school girl right now. Why shouldn't everyone else?

As I made my way through the halls, nobody paid me much attention, except ... I did see quite a few of the boys turning to stare. What I was wearing wasn't exactly proper, but it wasn't over the top slutty either. Still, I found more than a few pairs of eyes following me. Not surprising. Most girls didn't exactly walk around the halls dressed like stereotypical schoolgirls. Plus, my short blonde hair gave me a natural pixie cut, which I guess meant I was passing. Actually, judging from some of those stares, I must have been quite pretty.

The thought brought a flush to my face and added a new wave of humiliation. Thankfully, after a few minutes, the press started to thin out as people found their way to class or lunch, and I finally reached the stairwell. As I did, I passed a pack of senior boys who made several loud comments.

"Damn, girl, where are you going?" one of them said.

"Who the fuck is that?" another asked. "She's fucking hot."

A few blessed minutes later and I was down the stairs, turning onto the hallway to the library. I saw the boy's restroom and ducked in, planning to make excuses about accidentally walking into the wrong room, if there happened to be any boys inside. Thankfully there were not.

Lauren and Sadie, however, were.

"Took you long enough," Sadie grumbled, before really looking at me. "Well, look at you all pretty. A real fucking girly slut."

"Yes, she is," Lauren said, stepping forward with a smile.

I made to speak, but Lauren didn't let me. Instead, she and Sadie hurriedly pulled me into the larger handicap stall and pressed me hard against the wall. The stalls went floor to ceiling, creating essentially what amounted to a private little room. A fact for which I was grateful, as Sadie shoved a hand inside my tights, under my panties, and tapped the base of my plug.

"Seems our sissy slut knows how to follow directions," she smiled, looking at Lauren.

Lauren stepped back and gave me an appraising look. "Well done, Kenzie. You're being the perfect little sissy for mistress. Now, do you know why we asked you to come down here?"

"No," I said, standing there shaking as Sadie stepped back as well.

I was genuinely surprised when Lauren raised a hand and slapped me across my face. So surprised in fact, that I sank back and started to slide down the stall wall.

"You will refer to me as mistress, Kenzie." Lauren's eyes were stern. "You will also refer to Sadie as mistress, as well. In the event you need to differentiate, you may add our names, but you are to always address us with the title, of mistress. Understand?"

"Yes, mistress," I whispered, pressing hand to my cheek, which still stung from where Lauren had slapped me.

"Good girl," Lauren whispered. "Now, we asked you down here, because, well, how best to phrase this. You see, that little video we took of you sucking Sean's cock ... well it seems someone, we couldn't say who, spread it around to all the senior group chats. You've generated quite a lot of interest. We had a lot, and I do mean a lot, of guys asking us for a similar experience. Of course, they have no idea that you're just our pathetic little sissy trainer. In fact, they seem to be under the impression that you're a real girl, and the new school slut. The girls on the volleyball team have denied we know anything, naturally. We don't want the team getting a bad rap because you decided to suck cock in one of our uniforms. But, we do feel obligated to keep your burgeoning popularity growing, don't we Sadie?"

"Oh, yea," Sadie replied. The smile on her face scared me.

"After all, you're a pathetic little loser, aren't you Kenzie," Lauren said, kneeling to be eye level with me. "Now that you're getting to experience what it's like to be popular, we'd hate to take that away from you. So, we've decided to help your reputation along. Just as you arrived, Sadie sent an anonymous message to, well, quite a few of the interested boys. We've invited them all down to this particular restroom, to experience your talents first hand. Know why?"

My mind was starting to lose it. Everything Lauren was saying was pure nightmare fuel. I couldn't even begin to grasp the implications, so I did the only thing I could think to do. I shook my head.

Lauren didn't reply, but simply gestured above my head. Slowly, I followed her finger and saw that just above where I was sitting, right over my head, was a hole. A neatly cut, duct tape lined hole, right into the next stall. Was that ... was that a fucking gloryhole?

"Surprised?" Lauren asked. "Don't be. High school boys are disgusting a majority of the time and to be honest, I think it's more of a joke than anything. But since nobody uses the library much anymore, nobody has bothered to fix it. Our little gloryhole here probably hasn't ever seen much use. Well, until today. Get the picture Kenzie? You're going to be a good little gloryhole slut for us, and suck every cock that comes through. Otherwise, well, you ... meaning the old you, Mr. Miller, will be getting very famous, very fast. So, what's it going to be? Will you be Kenzie, my good little sissy slut. Or do you want to go back to being Mr. Miller."

I'd like to say I thought about it more. That I had some fight left in me. But I didn't. There really wasn't even a choice.

"Kenzie," I whispered. "I'd like to be Kenzie, mistress."

About five minutes later the door to the bathroom opened and there was a lot of hushed whispering. Multiple voices. By this time, Lauren and Sadie had me squatting on my heels in front of the hole. Sadie had produced a couple of hair ties and had given me the crude pigtails again. She was gripping both of my pigtails tight, standing right behind me, while Lauren sat on the toilet, legs crossed, with a small device in her hand, smiling. After some more whispering, the door to the next stall opened, there was some loud fumbling with what I guessed to be a belt, and then, just like that, a cock came through the gloryhole.

It wasn't huge, maybe about the same size as Sean's, but way hairier. Sadie leaned down and whispered, "Showtime," as she dragged me forward. "Say, ah," she said, before forcing my open mouth onto the cock. I really hated being forced onto a cock like this, especially since I couldn't control anything.

There was an audible gasp in the next stall as I started sucking, and Sadie set a vicious pace. Immediately I heard voices.

"She's fucking for real man," someone said.

"You're fucking joking?" came another voice.

"Dude it feels so good," came a third voice, which sounded closer and I assumed belonged to the senior whose dick I was currently sucking.

There were more audible gasps, and I thought I heard the bathroom door open again. Whether that was to let more people in, or someone leaving to tell all their friends the good news, I wasn't sure. I didn't have much time to ponder the question thought, since Sadie quickly had me near breathless, bobbing my head up and down on the first cock. Thankfully, whoever happened to be on the other side must have been very excited because they began to cum just as Sadie was pulling my head back for maybe the tenth or eleventh time. I expected her to thrust me back down again, burying the cock in my throat. Instead, as soon as she realized what was happening, she pulled me all the way off, and hurriedly whispered, "Jerk him off, you stupid slut."

Not thinking, I reached up and began stroking the cock in front of me, as Sadie held my head still and several ropes of runny cum splashed across my face. A few more seconds of stroking and the cock withdrew.

It was only then I realized that Lauren was filming. She had her phone trained on me, and she was smiling. I must have been quite a sight. Hair in pigtails, faced covered in cum, wearing my little white polo, plaid skirt, squatting in my tights on my heels. Even I could only imagine myself looking exactly like the kind of gloryhole school slut that Lauren had described.

At that exact moment, two things happened. Lauren clicked a button on the small device in her off hand, and the plug in my ass whirred to life. The vibrating and pulsing started immediately, and were instantly almost too intense. At the same time, a second cock came through the gloryhole. Sadie waisted no time in pushing my open mouth right onto it, making sure I gave our second attendee no less enthusiastic a blowjob than the first.

The second cock had blown his load right down my throat, as Sadie had made me deepthroat whatever lucky guy it belonged to. The third had once again cum on my face. The fourth, fifth, and sixth cocks had all gotten their loads swallowed by yours truly. After that, everything became a blur. I don't quite remember how many cocks I sucked, but Sadie would occasionally have me stop and jerk one onto my face, or have me gargle a load our two. I tried to mentally block the whole thing out.

All I knew was that the more cocks I'd sucked, the more intense the vibrations in my ass had become. The pulsing sensation was becoming almost overwhelming. Of course, no matter how distracting the sensations in my ass seemed to become, Sadie was there to make sure I didn't slack off on my gloryhole duties. Lauren, meanwhile, documented the entire thing on her phone.

I was just finishing the fifteenth or maybe the sixteenth cock. I'd long since lost count. I suppose it didn't really matter, since as usual, there was another cock waiting right behind it. The current lucky guy was busy pumping a long stream of cum right down my throat, straight into my stomach, when, as he withdrew, I felt Sadie pulling me up to my feet.

"We're almost out of time, right?" she asked.

Lauren glanced at her phone. "Yeah, about five more minutes in sixth period."

"Can you break her in now?" Sadie asked.

I wasn't sure what Sadie meant by that question, but I didn't like the way Lauren smiled as she answered.

"Be my guest."

With that, I felt Sadie lifting me, dragging me back to my feet from where I'd been squatting. She pulled me back away from the glory hole, just as another cock came through. Most of the dicks I'd sucked so far had all been relatively the same. Sure they'd looked different, but it was hard to tell them apart once they were in my mouth or buried in my throat. This one though, was huge. It had to be nine, maybe ten inches long and boy was it thick. Like, concerningly thick.

I didn't have much time to be concerned though. Sadie's hands were firmly on my hips and she was bending me over, pulling my hips back toward her. Roughly, she pushed my head down toward the new monster cock in the gloryhole. This forced me to bend at the waist, to keep my heels from sliding on the tile. In one fluid movement, she flipped my skirt up, yanked my tights down, and pulled my panties to the side. A half second later I felt a tug on the plug and there was an audible pop as it came out of my ass.

Gravity let the bulb of the plug swing down between my legs, where I could see it dangling. However, because of the silicone bands around my chastity cage and balls, the plug didn't drop to the ground. I noticed with some alarm that the plug looked much larger than when I'd shoved it inside my ass.

Lauren must have guessed what I was thinking, because she answered my unspoken question. "All that pulsing you've been feeling was actually a lovely little self-expanding feature. When I turn it on, the plug swells inside you, instead of thrusting. It's a nice way to train your ass to take bigger and bigger plugs. Or, ya know, something else."

A second later something began to push against my ass. I'd momentarily forgotten about Sadie in my confusion of looking at the plug. Glancing over my shoulder, I could see that she was now positioning what must have been a strapon, right in line my asshole. There was a leather harness around her waist, and she was drizzling a bottle of lube along the length of silicone between her legs.

"Buckle up, slut," was all she said, before driving her full length into me.

My ass felt like it was on fire, but I didn't have time to protest, because as soon as I opened my mouth to scream, Lauren reached over and pushed my mouth onto the massive waiting cock, which promptly slipped right to the back of my throat. My life instantly became a series of overwhelming sensations. Sadie was pounding my ass with a fury, which in turn, forced me deeper onto the cock buried my mouth, which then caused me to gag and push back into Sadie's thrusting. Which of course then pushed me even deeper onto the cock of whatever senior boy happened to be one the other side of the gloryhole. This process repeated until I felt the head of his cock slip past the back of my mouth and down into my throat. Deep into my throat. Which then presented me with an entirely new problem. I couldn't fucking breathe.

Panic set in quick. Here I was, dolled up like a little schoolgirl sissy slut, deepthroating a cock far too large for me, while Sadie was forcing what I imagined was an equally sizeable dildo, deeper and deeper into my ass. I tried to scream, gagged, and ended up basically swallowing the entire length of the cock in my throat, which of course meant I started to black out. My vision went in and out for a second, and I only avoided passing out because the strange sense of pressure in my ass came back with a vengeance. It just seemed to keep building and building. The harder Sadie thrusted, the more it grew.

Eventually, just as I thought I really was going to pass out, the massive cock in my throat pulsed. All my gagging and swallowing must have felt incredible. That or this guy really lacked stamina, because his cock twitched once, then twice, then emptied the largest load I'd taken so far, right down my throat. By this point, he was so far past my gag reflex, it couldn't do anything but feel the warm sensation of cum sliding down my esophagus. As his cock retracted, Sadie did not let up her pounding.

She kept me bent over, as she continued to rail my ass. No longer being spitroasted, I had a little better balance, but I could still barely keep my feet, feeling awkward in my heels.

"Take it, slut. Fucking take it." she said, as she moaned. Or was that me? I couldn't tell anymore.

I turned to look at Lauren and saw she was still filming and again, I thought about what a sight I must be. At this point I was truly coated in cum. My hair was a mess. Saliva and cum were dripping from my mouth. I decided it was me moaning, and boy did I sound like a slut. Like an actual pornstar, moaning, as Sadie fucked my ass with a strapon. All while dressed like a schoolgirl slut.

My head slumped in shame. It was then that I saw a steady stream of ... something... leaking from the tip of my chastity cage. Then, all at once, Sadie buried her strapon deep inside me and slapped my ass hard. Her legs went stiff and she all but pushed me off her length, to slump against the wall.

"Holy fuck," she moaned, exhaling sharply. "God my pussy is still quivering."

Had she just had an orgasm from fucking my ass? Honestly, I was too out of it and far too exhausted to care. I couldn't do much but sit and stare at the two girls who completely owned my life. I just hoped that this would be the end of it.

A few minutes later, after Sadie had come down from her orgasm and Lauren had apparently finished saving whatever videos she'd taken of me, I was disappointed. Finally having gathered the courage to speak, I asked a single question.

"Can... can I go home now?" I stammered.

Sixth period had long since ended and the school day was over. As the athletic trainer, I didn't have much in the way of after-school duties, but I did need to clean myself up, somehow sneak back to my office looking like a cheaper whore, and probably find some time to have a good cry. I felt so fucking humiliated. So used. Like ... like an actual sissy.

"Actually," Sadie said, exhaling and finding her feet again. As usual, being volleyball players, both her and Lauren towered over me. "There is one last little thing we need you to do."

"There is?" Laura turned to her friend, feigning surprise.

Despite the attempt to make this seem spur of the moment, whatever was about to happen, the girls had clearly preplanned. I sat there on bathroom floor, my ass burning and my throat raw, just waiting for the punchline.

"Well, you see," Sadie said, doing her best to sound sheepish, "While little Kenzie sucking Sean off is going to help us in Calculus, I'm actually struggling in more than one class. Government is a real pain in my ass right now. Mr. Wheeler is a fucking dick and well, since our season started, I've missed turning in a few assignments, so my grade is kind of ... cooked."

"Oh, that is terrible," Laura gasped. "And what do you want little Kenzie to do about it?"

"I might have hinted to Mr. Wheeler," Sadie said, "that if he overlooked all those assignments I missed, that I might consider meeting him in the gym tonight and uh, blowing him under the bleachers."

Mr. Wheeler, or Ted, as I knew him, did indeed have a reputation of being a hard ass. Balding, overweight, and in his mid-fifties, he was also not a looker as it went. I was surprised that Sadie would be so forward as to offer sexual favors to a guy like that. Though, to be fair, even amongst the teachers, Ted Wheeler had a reputation of being... well, that sort of guy. But never, ever with the student-athletes. Something didn't make sense.

Then Sadie smiled, and my stomach dropped. I had a bad feeling I knew where this was headed and I felt like I wanted to start crying right then and there.

"Hinted?" Laura laughed.

"Told him," Sadie corrected, smiling. "That, among other things. Anyway, I figured since the gym will be empty and mostly dark, Kenzie here might be able to fill in for me. I mean, she's a little shorter than I am, but Mr. Wheeler is a big guy, so I doubt he'll notice. Besides, you put a volleyball uniform on our little sissy here, plus a red wig or something, and she could pass, don't ya think? I mean, especially in the dark. You know how dark it can be under those bleachers."

"I sure do," Laura said. "But wherever would we get a red wig to match your hair?"

I watched as Sadie pulled a red wig, not quite her style, but fairly close, from her backpack. "Wouldn't you know it, I have one right here."

Thirty minutes later I was standing under the gym bleachers, in one of the few spots of dim light, wearing one of Sadie's spare volleyball uniforms and the wig she had given me. There'd be some general fussing about making sure the wig stayed on, but the girls had apparently found the money for a good one, because after a little glue application and some effort, my own shoulder length blonde hair was tucked safely away and I was left with beautiful auburn locks, that flowed down to my mid back.

Both Sadie and Lauren had agreed that if Sadie had been the type of girl to meet Mr. Wheeler under the bleachers, that she would also have been the type of girl to put her hair into some slutty pigtails - blowjob handles they said - so as was becoming the trend, that is the style I was sporting.

The uniform, I had been assured, was an older one from the team room that no one would miss. The number matched Sadie's so Mr. Wheeler wouldn't get suspicious, and the white spandex shorts were undoubtedly of the same kind I'd been wearing when I'd blown Sean the previous evening. I was also wearing the same knee-pads as before, though this time the girls had given me some shorter crew socks and an old pair of Asics volleyball shoes. I thought the whole ensemble was a bit much, but apparently if Mr. Wheeler wanted a volleyball player, he was going to get one

I was still wrestling with the feeling of dread, knowing that I was about to suck off yet another cock, and one of my colleagues no less. The fact that he'd be thinking I was just one of his students didn't make the situation feel much better. If anything, it made me feel even dirtier.

I couldn't have said how long I'd been standing there, very much lost in thought, but it must have been longer than I'd realized, because suddenly there was a voice behind me. A voice I knew.

"Well, well," Mr. Wheeler said, from somewhere in the darkness. "I wasn't sure you'd come. More desperate than I thought, aren't you Sadie."

It really was very dark under the bleachers, so it took me a moment to locate Mr. Wheeler. I spotted his large outline leaning against one of the bleacher supports. He was certainly bigger than me, very obviously overweight. Once he noticed that I'd seen him, he took a few steps my way. The lighting wouldn't be great, but he'd definitely be able to see some of my features. Especially if his eyes had adjusted to the dark. Evidently they had because he looked at me over appraisingly.

"You're even wearing your uniform, like a good little girl."

I nodded, and kept my head down.

Mr. Wheeler closed the distance and put a hand on my head, running a hand along my pigtails. "What's the matter?" he said. "You were so bold, about all the things you'd let me do to you, to save your grade. Now you can't even speak." He laughed. "Or maybe you're just excited to suck my dick, is that it?"

"Yes," I muttered, meekly in my best girly voice. The girls had made me practice my voice in the half-hour or so it had taken to get me ready.

It must have been pretty convincing, because Mr. Wheeler didn't comment. He got right to business, forcing me down to my knees. The next thing I knew, his cock was already out and he had both hands wrapped around my pigtails. "Well, get fucking sucking, Sadie."

Hearing him call me Sadie was a bit of a shock. But not unexpected. I guess she really had convinced Mr. Wheeler that she was going to suck him off. The knowledge that my identity was still truly a secret was only a mild consolation though, as I leaned forward and took Mr. Wheeler's cock in my mouth. He was bigger than Sean, but maybe not by much. Certainly not the largest cock I'd sucked today.

He wasn't really gentle either. He thrust in and out of my mouth, bypassing my gag reflex with no remorse. His hands were firmly gripping my pigtails, pulling me deeper onto his cock with each thrust. There were several moments where I thought I might throw up, and several more where I thought I might pass out. I had to rest my hands on high thighs to keep from toppling over. My throat was still raw from all the gloryhole "fun" I'd had earlier, so my eyes welled with tears almost immediately.

After a series of particularly deep thrusts, Mr. Wheeler pulled me so deep onto his cock that my nose was buried in his pubes. I had no choice but to let him, as I feared that offering any resistance would tear the wig right off. He smelled so strongly of sweat that I had to make a real effort not to pull away. The longer he held me, the more I thought I really might vomit this time, as I could feel myself gagging on his cock, as it remained buried deep in my throat.

He held me like that for a few more moments, before violently pulling out and letting me slump to the ground. "Well," he sighed, stepping back. "That should about do it."

I lay there in bewilderment. That was it? He didn't even cum. Not that I was complaining. I'd swallowed more than enough cum for today, so if he was satisfied, then I wasn't going to argue with him.

Feeling a brief moment of relief, I started to stand, turning away from him and using some of the trusses under the bleachers to pull myself up. I fumbled for a bit in the dark, but eventually I managed to get my legs under me. Then I felt hands pulling on my hips, grabbing my ass, followed by a ripping sound, that I could've sworn was some kind of fabric.

A sudden cool breeze on my ass startled me and it took my mind a moment to catch up. Had he just ripped my shorts? A second later I felt one of his huge hands on the back of my neck, as my head was forced down. His other hand was still holding my hips, so I had no choice but to bend at the waist.

Suddenly, I found myself effectively wedged between a few of the trusses under the bleachers, off balance, bent over and standing almost on my tip toes. I couldn't really move or fight back, and I had no clue what the hell was happening. How did he expect me ... or, uh, Sadie, rather, to suck his dick like this? I was basically a fucking ninety-degree angle right now.

"Now," Mr. Wheeler said, from behind me. His voice was almost a growl. "Let's make good on your other promise."

Other promise? What the fuck was he talking about? At that moment, something hard and fleshy pushed up against my asshole. I started to scream, but bent over the steel trusses as I was, I couldn't get enough breath. It came out as more of a moan than anything.

"That's right," Mr. Wheeler gave my ass what I'm sure he thought was a playful slap. "Let me in, sweetie. Let me fuck your ass. All that fucking talk about being an anal virgin. You got me all riled up. I was so hard thinking about taking your anal virginity."

I tried to say something. Anything. I wanted to confess. To tell him I wasn't Sadie. To But nothing would come out. His cockhead was pushing against my asshole. It was so much pressure. More pressure than even Sadie's strapon. Plus there was no lube, apart from my spit on his cock. Then, with a flash of pain, I felt his cock slip pass my sphincter and inside me. Thankfully, there must have been some excess lube from when Sadie has been fucking me with the strapon earlier, because Mr. Wheeler didn't seem to have a hard time getting going.

In mere moments, he was pounding in and out of me far harder than Sadie ever could have managed. The force of his thrusting was so intense, I couldn't even really settle back onto my feet. His constant pounding kept me up on my tip toes, my volleyball shoes making the occasional odd squeak on the gym floor as he grabbed my hips and ... and ... and fucked me.

When Sadie had used the strapon on me earlier, I could rationalize it. I didn't like it, obviously, but I could almost live with it. Even sucking dicks ... well, that was a lot harder. It felt like I was crossing a line, but that there might be a way back. But this ... having Mr. Wheeler's cock buried in my ass. Having him use me. Fuck me. Having a man, fucking me. It felt like there was no real coming back.

The only saving grace was that, positioned as I was, there was no way Mr. Wheeler could see my caged cock. He wouldn't be able to tell who I really was. It was a relief of sorts, I guessed. It also meant that he genuinely believed he was fucking Sadie's ass. Why the fuck would Sadie promise a guy like Mr. Wheeler he could fuck her -

It sank in. She'd never intended to be here. Both she and Laura had cooked this whole thing up so that Mr. Wheeler would fuck me. The realization made me shudder, which Mr. Wheeler must have taken as a sign of pleasure. Either that, or he mistook my quiet grunts of pain as moans, because he chose that moment to slap my ass again.

"Good girl, Sadie," he moaned. "God your ass feels fucking good."

Thankfully Mr. Wheeler wasn't much on stamina. After a few more brief, but intense, minutes of violent thrusting, I felt him slow. Then groan. Unfortunately, what followed was a very warm, very wet sensation in my ass. I could literally feel his cock pulsing inside me as he shot rope after rope of his cum into my ass hole. A few seconds more and he pulled out.

"That was ... uh, very good, Sadie." Mr. Wheeler sounded very out of breath as he took some time pulling up his pants in the dark. "I'll, uh, bump your grade up to ... let's call it a B. Maybe a few more of these extra credit sessions and we can work you up to an A. See you in class tomorrow."

With one final swat on my ass, Mr. Wheeler walked off and out from under the bleachers. I sagged to the floor. My asshole was once again on fire. Humiliated, abused, feeling like my life was in ruins, I oddly found my mind drifting toward a rather perplexing line of thought.

I hadn't really felt anything when Mr. Wheeler had been fucking me. There was ... no pressure. No sensation in my ass that made me go breathless. Nothing like when Sadie had been using her strapon on me earlier, or even what the butt plug had felt like when I'd sucked Sean off. Strange. What a curious thing for me to focus on.

"He's bumping me to a B!" Sadie shouted in outrage, as I knelt in front of her and Lauren, back in the team room. "He's only bumping me up to a fucking B! That's bullshit. My ass is worth an A all day. What the fuck did you do, you sissy slut?"

"I'm sorry, mistress Sadie," I said, keeping my head down. "That's what he said."

"You listen to me slut," Sadie said, taking hold of my pigtails. "You'd better do better next time, you hear me! You're going to take that fat's fuck cock as many times as you have to to get me an A, you understand?"

"Settle down, Sadie," Lauren said placatingly. "Of course Kenzie here will take as much cock as she has to for her mistresses, won't you Kenzie?"

I didn't even pretend to protest. "Yes, mistress"

"She'd better," Sadie said, turning to stalk out of the team room.

Lauren watched her friend leave before she too rose to leave. However, before she walked out the door, she turned back toward me, with a very chilling smile. "How was it, my little sissy slut?"

"How was what, mistress?" I asked, staring up at her blankly.

"Losing your virginity, you dumb whore, what else?" Lauren raised an eyebrow at me. "I mean a pathetic little bitch like you certainly never fucked a woman. Or am I wrong?"

"Uh, no, I, uh, haven't mistress," I said, slowly.

"Well, then, if you'd never fucked a woman, and you're not gay, as you reminded me yesterday, then Mr. Wheeler would be the first time you've had sex, yes? I mean, think about it. What else would you call a man shoving his cock up your hole."

"But ... but it was ... I mean - " I tried to protest, a slow horror dawning on me. She was right. "It wasn't..."

"It wasn't what?" Lauren shrugged. "Sex? You had a cock up your ass. Though, I guess as a sissy, since you're not a real man, your ass is more like a pussy anyway. An ass-pussy, let's call it. Either way, as far as I'm concerned, Mr. Wheeler just popped your cherry. And you let him do it raw. I mean, you took a fucking creampie, you dirty slut. Sounds like your first time to me."

I stared, my mind blank.

Lauren smiled back wickedly. "Well, go home and get some rest, my freshly deflowered whore. Make sure you plug yourself back up before you leave, sissy. You've got a big day tomorrow!"

With that, she turned and walked out, leaving me kneeling on the floor in a very ruffled volleyball uniform. It took me a few minutes to refit the plug. Getting the silicone ring around my balls proved to be the most challenging part, as bulb slipped into my ass without much of a fuss. Most of Mr. Wheeler's cum had dripped out of me at this point, but what was left must've been acting as lube.

I redressed in my normal clothes and I got ready to head home. I had a sinking feeling that Lauren wasn't at all joking when she said I had a "big" day ahead of me tomorrow.