Average High School Life Ch. 06

"I think I'm all right," I said, "do you need something?"

"So we printed something up the other day and we're having a disagreement about whether it came out right," Max said.

She reached into her oversize bag and pulled out a bright orange dildo. It looked a little smaller than the one they'd printed the previous week.

The desk I usually sat at was a reception-style desk with a wall and counter in front of the table top, so I quickly pulled the toy down and out of view of the rest of the room. Four people were still there working on various things, all of them guys, and they kept stealing glances over at my desk, obviously trying to ogle the women.

"You did clean that, right Cunt?" Max said, though more quietly than in the scene I'd shared with them.

"Um...I think so Mistress," Charlie said even quieter.

"You think...fuck. How dumb are you? Are you sure that's your real hair color? All right Jay, the point is I think it works perfectly fine, but Charlie insists it's not good. We need a third opinion."

"Um...I'm not really into taking it up the ass," I said.

"Ohh you haven't let me at it then," Max said with a leer, "I'd have you on the floor, cumming your brains out, begging me to play with your backdoor."

I suddenly had a clearer appreciation for what "fear boner" meant. It was something in the tone of her voice as she made the threat/offer.

"But that's not what we want. That's Cunt's anal dildo. I want you to make sure it works the way we want."

"Um," I said, looking around the lab, "Are you coming back later?"

"No reason to wait, I don't think. Hang on," Max said.

She turned around and walked at one of the older men. "Excuse me," she said loudly to get his (and everyone else in the lab's) attention. She then said something quieter and pulled out some money. The older man pulled out a wallet and they exchanged bills.

I was as riveted by the exchange as everyone else, so I was a little surprised when Charlie bumped me. She'd come around and knelt down next to my chair, slipping halfway under the desk. From that position, unless you came around behind the desk, she wouldn't be visible.

Max came back over and said, "Can always count on the older guys to still carry cash. And dealers. Is my Cunt all settled and in place?"

"I think so," I said.

"Good," Max said, digging into her bag and pulling out a bottle that she dropped on my desk, "test out the toy."

The bottle was lube. I picked it up slowly and undid the top, then hesitantly grabbed the fake cock.

"Lift up the cunt's dress and hold the toy over her ass. Then any drips go on her."

My eyebrows made a run for the top of my head. I hesitantly reached over and found the hem of Charlie's dress, then lifted it and pushed it forward. I uncovered Charlie's pale, white, heart shaped ass, totally bare next to me.

"Better posture, cunt," Max said a little louder.

Nobody noticed except me and Charlie, who arched her back. Now, in addition to her ass and the puckered hole between her cheeks, the lips of her pussy came into view. I applied the lube to the toy, holding it over her backside as instructed. A few clear drops landed on her round cheeks and even in the pucker and I saw her flinch.

"That should be enough," Max said after a moment, "now just line it up, grip the base, and push it. Go slow, but you don't have to worry too much; her ass is well trained."

I then learned firsthand how much more difficult it was lining up a cock when you couldn't feel it. It also didn't help that my hands shook badly; despite last time, Max seemed a lot more intense and almost cruel, and it was throwing me off a bit. It took me a minute or so but I got the tip settled on Charlie's rosebud. My first push sent the cock sliding up her crack and along her back.

"I said you were well trained, Cunt, don't make a liar of your mistress!"

Max somehow made it sound like she was yelling even though her voice barely went above a whisper. I saw Charlie's asshole flex and open a bit as I settled the dildo again. This time when I pushed, it went in.

The puckered flesh widened and stretched tight over the orange head, then the ridge popped through the ring. I heard a slight grunt from Charlie when that happened and I hesitated, but then at Max's expectant look, I kept pushing. I'd never had the opportunity, but I'd always thought the attraction of anal would be the sensation on your cock. Right then, though, the sight of the orange rod pushing into Charlie's ass was amazingly erotic all on its own. In much less time than I thought, I had the dildo settled all the way, the fake balls of the toy pressing against the taint of the redhead under my desk.

I didn't tell Max, but at some point Charlie had gripped one of my ankles as I penetrated her with the toy. She still held onto it, and I felt oddly thrilled at the contact.

"Now, let's see if it works like it should. Check her pussy, tell me how wet it is," Max said.

I hesitantly brought my hand over and rested it on her thigh, just next to Charlie's folds. Her skin was amazingly soft and felt cool. She flinched a bit as my hand made contact, and I saw the dildo twitch as her ass clenched around it. Her hand tightened around my ankle, too.

Max nodded at me again, and I slipped a finger inside her. I could feel the hard dildo through the thin membrane in her pussy, which was hot and soaked.

"She's wet," I said.

"Let me have a taste," Max said.

I pulled my finger out not really thinking about it and slowly brought it over. Max quickly looked around and, seeing everyone else was distracted, she bent down and sucked the finger into her mouth. I felt her tongue swirl around it quickly before she drew back. She licked her lips after that, and for the first time I noticed she had subtle purple lipstick on them that matched her hair. Amazing what the teenage male mind will focus on given proper motivation.

"Mmm," Max said, "I think that's working just fine, don't you?"

"I...um...if that's what you were going for," I said.

"Hmm, I think we need some more testing," Max said as she shouldered her bag, "I've got some errands to run. If I leave her here, can I swing back after you close up?"

I quickly glanced at the clock. There were forty minutes left until closing.

"Um...you mean..."

"Just keep her behind the desk. Also, be sure to play with that toy. It should stay where it is, but you can pump it and twist it around all you like. Think of it like a fidget toy. Just add more lube every now and then, and be sure to keep checking how well it's working. She's all yours until I get back."

Max walked off before I could really respond. I looked down and I still saw the shadowed, pale globes of Charlie's ass with the orange toy lodged in her anus, her pussy just below it now inflamed and wet. I didn't do anything for a few minutes, checking the patrons to make sure they still seemed unaware of what was going on. Nobody paid me any attention, and one of the men had actually followed Max out, either coincidentally or in a desperate attempt to make a play for her.

I was still uncertain about actually doing anything, but I remembered Max's instructions. I was pretty sure she wouldn't do anything to me if I actually didn't want her to, but it also might mean she'd never come back with Charlie. I mean, I had no guarantee she was ever coming back anyway, but my brain was heavily suggesting I should still do whatever I could to make it more likely.

I slowly brought my hand back over to the orange dildo and gripped the base. I felt Charlie's hand tighten on my ankle, and then grip even tighter as I pulled. I continued pulling until the "head" just slipped past her ring, then pushed it back in slowly. I mesmerized myself for a while watching her ass grip the orange toy as it pulled out.

Then I remembered Max telling me to "keep checking to see if it worked." I pushed the dildo back in deep so the balls settled against her once more, then slipped my fingers down to her pussy. Her lips were spread wide now; apparently she really liked the dildo in her ass, or at least her body did. My finger slid into her almost by accident, she was so wet. When it did her grip tightened again. I brought my hand out and heard a faint, pleading moan. Guessing what she wanted, I slipped my finger down along her lips until I felt her clit. It was jutting out and hard.

I barely flicked my finger over it and I thought her nails would claw skin off my foot. I got to watch her ass ripple as she shuddered from the orgasm I'd obviously just given her.

I returned to lazily pulling out the dildo and admiring how her ass gripped it. I added more lube when the toy seemed to be sticking, but then I had to pause.

"Hey Jay," one of the guys said, heading for the desk. His name was Nick and he came in often enough that I recognized him. I thought he was a grad student at a local college, but he usually wanted to chat with me about video games. He was a far more avid gamer than I was, but I knew enough to talk about them and he just mostly wanted someone to vent to. I was a captive audience.

I felt Charlie tense up when he got close and we started talking. I'd stood up to talk to him, but then I got a naughty idea. I shifted around and sat on the desk, resting my foot on the chair. It looked awkward, but I was a guy bored at work; sitting weirdly was practically a hobby. Nick didn't notice or care and kept regaling me with tales of his latest virtual adventure. Meanwhile, I started to swing my foot.

Nick didn't notice, but I bet Charlie did. My swinging foot swiveled the chair, and the piece holding the back to the seat swung around right into the base of the dildo. I heard a small thump the first time, probably Charlie bracing herself to keep from falling over. I kept up like that for a few minutes while Nick talked with me (or, more accurately, at me). Eventually I thought my foot was actually pushing the dildo back into her ass a bit and I wondered if she was pushing it out herself.

Eventually I had to hit the button that sent the 10 minute warning chime throughout the lab. Nick used that cue to take off and I sat down in my chair. I immediately felt my pant leg come up and lips were against my bare skin, moving. I finally realized they were saying something.

"Please."

Guessing what Charlie wanted, I slid my finger up between her folds again, brushing her clit. Her mouth slammed against my leg and she moaned into my shin as her body shuddered again. I wiped my finger off on the smooth skin of her ass.

The other two guys left a few minutes later as I distracted myself by twisting the toy around as it stayed lodged in her ass. I was still a little worried at the dynamic here, but Max had assured me Charlie was okay with this. If she'd wanted to move or run off I certainly wouldn't have stopped her, but she'd just stayed in place, and she came twice. Plus the thrill of doing all this at my job was definitely getting to me.

"I'm glad you're having fun with my Cunt, Jay."

I nearly fell out of the chair as Max leaned over. "I locked the door for you but I don't know how to do those shutter things," she said with a knowing grin.

"I...um...yeah, I can get those," I said.

"Oh don't leave yet," she said, "Cunt! Come out and stand up!"

Charlie came out from beneath the desk. She was definitely not photoshoot ready. Her face was flushed and her hair was dark where the sweat had stuck it to her skin. Her lipstick had also smeared a bit.

I looked over and saw that Max was furious. I panicked for a moment, wondering what I'd done, but then she came around the desk and grabbed Charlie's face.

"How many?" she snapped, inches away from the girl's nose, "How. Many!?"

"T-t-two mistress," Charlie sputtered, seeming on the verge of tears.

"Do you remember me saying you could cum? How many orgasms did I say you could have, Cunt? Do you remember?"

Charlie opened her mouth but she didn't answer fast enough for Max.

"None! Zero! I should have come back to a nice cunt, all primed and ready for cumming, but you couldn't control yourself could you?" she snapped harshly.

At that point I was a bit freaked out by her intensity and I could see tears leaking from Charlie's eyes. That's why the next exchange gave me very mixed feelings.

"Now since you enjoyed yourself so much, you're going to thank the man who gave you those orgasms," Max said.

Charlie turned toward me. "Th-thank y-"

"Oh my god you stupid cunt! He got you off! Common courtesy is to return the favor. Now get his cock out and get it inside you!"

"But Mistress, he's a man! I-"

"Should have thought of that before you got off to him. Now get his cock out!"

Charlie scrambled over to me and practically tore my pants off. I almost said the safe word Max had told me last week; I really didn't want to have sex with Charlie if she was against it. But my brain kept reminding me, loudly, of the fact that I'd already done it once, and that Charlie could tap out the same way I could. I also heard CC's voice saying, why are you complaining about women fucking you?

Charlie pulled on my pants frantically and I lifted my hips to let them slide off. Charlie's reactions didn't kill my arousal that much and I was respectably hard when my cock was exposed. I saw Max reach down under Charlie's dress, and then there was a panicked yelp from the redhead as she yanked out the dildo. She brought it over and gripped my cock, rubbing it lightly and getting me hard from the attention.

"There, see, he's smaller than the toy, you should have no problem. Mount him," she said.

Charlie still looked hesitant and she didn't move, so Max slammed the dildo down on the desk and took matters into her own hands. She pulled up Charlie's dress, exposing the red landing strip and her glistening, swollen pussy. Then she pushed Charlie toward me.

My office chair was a rolling one but had no armrests, so Charlie was able to get her legs on either side of me without a problem. Her height and the height of my chair meant my rigid cock brushed her lips as she shuffled forward and I could feel the heat coming off her. Then a hand gripped me and I saw Max's hand on Charlie's shoulder. She descended a bit and let out a little whimper when my head split her pussy open. She stopped there, then Max's other hand appeared on her shoulder, and then she was shoved down on top of me.

Her vagina didn't agree with her vocal protests because my cock slid right into her. She let out a loud moan that might have been a whine too, and she squirmed a little when she settled on my cock, which felt wonderful.

"This is for him, not you, Cunt! Start moving."

I heard a slap and then felt her dress settle back on my legs. Charlie started working her thighs, bouncing on my cock. Her pussy didn't grip my cock as tightly as I thought her ass gripped the dildo, but it was tight enough to feel really good.

"You didn't get to play with her tits much last time, did you?" Max asked.

I shook my head rather than try to speak. Max shocked me again by reaching around Charlie and literally tearing the dress, spreading the bodice open and showing Charlie hadn't been wearing a bra. I wasn't sure how I'd missed that before, but now the pale white globes with pink, hardened nipples bounced in front of me. I reached up and grabbed them, crushing the soft, warm flesh in my fingers and feeling the nubs of her hard nipples against my palms.

Charlie had let out a surprised shriek as her dress tore, and then a loud groan as I grabbed her breasts. Unfortunately for her, Max hadn't pulled back yet.

"That was right in my ear, Cunt!" she snapped, "God you are so loud when you fuck!"

Max walked around and grabbed the dildo off the desk.

"Have to keep you quieter so no one comes in to investigate."

My own eyes widened along with Charlie's as Max brought the dildo up to Charlie's face.

"But Mistre-mmmmph!"

The sight of Max shoving the dildo into Charlie's mouth did something to me. The perverse reality of how long and how deep that had been in her ass and the sight of it in her mouth excited some deep, disturbed part of me. I felt like my cock got even harder and I slammed my hips up into Charlie. The chair rattled and rocked as my hips went wild slamming into her. I heard her moaning and screeching even through the toy in her mouth.

The chair couldn't take it. There was a "pop" and the back gave out, pitching us both sideways, but somehow that violent shift in position did it for me. As I caught myself from falling, I also erupted onto Charlie, spattering her dress and tits with shots of cum as she fell onto her side. The dildo dropped out of her mouth and rolled. Max swooped in and picked it up, then started wiping it off with a cloth or wipe of some kind.

"Good job, Cunt. Now put this in your pussy. Go on and stop whining, you just saw me wipe it off."

I watched, riveted as Charlie spread her legs obscenely, her reddened pussy still pointing at me. She slipped the orange dildo in to the hilt, her lips stretching around the toy.

"Good. Now nobody else can 'accidentally' make you cum," she said mockingly, "Go wait for me out front.

"Mistress...my dress," she said.

Max walked over and grabbed the roll of basic Scotch tape and tossed it at the girl. "Do what you can with that or just hold it closed. Now go wait out front, I'm not telling you again."

Clenching her dress closed as best she could and waddling awkwardly with the dildo lodged inside her, Charlie scurried to the front. Max then turned to me and offered me a hand. I took it and she helped pull me up with much more strength than I suspected with her frame. However as she did, my pants fell to my ankles.

"Oops," she said, "let me help you with that."

She squatted down in front of me and gripped my pants and boxers, dragging them up slowly. Her head was right in front of my cock in that pose, and I started getting hard again despite just cumming. I probably couldn't reach full mast, but my cock seemed desperate to try. I looked down and saw her smirking.

"Ah the fortitude of 18-year-olds," she said.

"Come on, you're only what? Three years older than me?" I said.

"Ohh, you get extra points for that," she said and pulled my pants up. The way she caught my member the head was still peeking out a bit. She reached down and it seemed like she was going to just resettle my dick, but then her hand wrapped around it and squeezed. I looked up at her and our eyes met. I saw some heat in hers.

"You know how worked up I am after watching you fuck her?" she asked.

"I can guess," I said.

I had no idea where my sudden confidence came from, especially with this woman who seemed to make a lifestyle of heavy domination, but I reached my hands up and slipped them beneath her tank top. As I hoped, I found large, hard nipples under my palms when my hands found her smaller breasts. She pulled in a sharp gasp. My cock still wasn't getting really hard but it was definitely making an effort.

She grit her teeth and then pulled her hand out of my pants. She gripped my arms and moved my hands away from her tits, surprisingly gently.

"No bullshit, I'm really tempted," she said, "But I haven't talked with Charlie."

"Okay," I said, a bit confused.

She smiled sympathetically. "It looks like I call all the shots but I can only do that because we know each other well and we set clear boundaries. I can make her fuck anybody, but she gets...nervous about me with other people unless we've talked about it."

"Um...anybody?" I asked.

"Don't worry," she said, "She got tested last week, she's clean. And I know everyone she's been with in the past two weeks. It's not a long list but they're all good too. You get yourself checked?"

"No, I...I haven't been sleeping around much," I said.