Average High School Life Ch. 08

Thank you as always for the ratings and comments. I like seeing and reading them as much as you (apparently) like reading the story.

The BDSM angle is more of a focus this section, and I'll preemptively warn everyone that the more extreme fetishes are going to start creeping in after this chapter. I appreciate everyone sticking with it this far.

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My average "encounter rate" on my Friday runs definitely seemed to drop without Amy riding along. They were also a different flavor, so to speak; I didn't get as many propositions or invitations, but a lot of flashing and teasing. The invitations I did get were either from pairs of women or couples. If there was some sort of overarching force directing this, it seemed to prefer frustrating me and getting me turned on until the point where I could have a threesome. Single-partner sex wasn't enough anymore.

Maybe whatever force was doing all this was getting bored?

The only exception was a middle-aged woman who had answered the door very clearly drunk out of her mind. She'd looked me up and down very obviously and told me her husband was gone, probably forever, and wanted to know if I could help her out. I begged off but the encounter still stood out.

Saturday morning I got homework done for a bit. I tried to contact CC, but she left me on read four times before I gave up. I mentioned I was stopping by the hill before I left for work and did go there, but she never showed. I tried to remember when she worked at the game shop on Saturdays but came up empty. I could have gone there; it was in the city and I probably had enough time to manage it before I had to be at Central Pizza, but she also clearly didn't want me around.

I also had to admit dealing with her lately had been more drama than I really wanted. She was the one who insisted on open communication and honesty and now I was cut off from contact for the second time in as many weeks. Plus the amount of shit she was giving me over my behavior on this was getting to be a bit much. Especially since I could easily see her berating me for being a man-whore if I'd given in and started playing along with all the scenarios thrown in my face.

On the opposite end, I was irrationally excited that Amy would be working at Central Pizza with me that night. I was not giddy, because that word sounds silly. I tried to calm down and tell myself I was reading too much into it; Amy might just be succumbing to the effects of whatever this was. I mean, shy virgin girl was definitely a plotline in porn. I focused on the fact that those relationships never went any further in the videos. If there was any follow up at all it was usually a cruel joke where the guy immediately brags about "bagging" the girl in question or the girl mentions that she's going to run out and start fucking the whole neighborhood now that she knows how good sex can be and leaves her partner dejected and alone because he can't get it up again immediately (totally ignoring the half hour or more he stayed hard...on screen anyway).

Amy promised she'd see me and match our breaks. I told myself that meant she wanted to continue things. The fact that she wanted to keep things going obviously meant it wasn't the influence of...whatever. Solid logic there. Go me.

Still, I was nervous walking into the shop. In a moment of pessimism, I'd thought maybe I'd walk in to see her bent over one of the kitchen counters with the kitchen staff running a train on her while she invited me to join in, but thankfully she just stood behind the counter and the cooks and her uncle were milling around behind her making pizza and whatever else.

Amy beckoned me closer and I leaned partially over the desk. She looked around quickly, then moved up and kissed me. There wasn't time for an involved lip-lock but it was enough to thrill me. Then she handed me a list of deliveries.

"Make sure not to let any horny housewives drag you away. But tell me about them," she said.

There were only three on the list, and two were no-contact drop-offs, so nothing interesting happened. When I returned for the next batch my list only had two, and they weren't that far from the shop. I didn't think anything of it, but it was unusual.

The second drop on that round was tough. I could hear shouting through the door when I got there and texted the pizza was on site. The front door was ripped open only a few seconds later and an obviously angry woman glared at me. I couldn't really tell if she was attractive or not because she was in a very fluffy bathrobe and her hair was up in a towel. Her angry expression didn't help her appeal.

She turned back into the house and shrilly yelled, "Your fucking pizza's here you worthless sack of shit."

"Good!" I heard from farther in the house, "Since that seems to be the only way I can get a decent meal around here!"

"Well how about I use him for a decent dicking then, since you haven't given me that for years!" she shouted back.

"You sure he wouldn't have to get at the back of the line?! I hear it goes around the block more than you do!"

"I'll show you a block you fucking asshole!"

The door slammed and I realized I'd sort of unconsciously walked up and handed the pizza to her during the tirade. I spent some time mentally debating if that counted as a proposition or not.

When I got back to Central Pizza there were people inside and the phone was ringing. Amy looked a bit frazzled and gave me an apologetic look as she handed me a list with five different addresses and pointed to a pile of bags. I set out.

One woman answered the door in a bathrobe she'd forgot to close, displaying her modest breasts and neatly trimmed pussy along with her athletic body. She seemed to literally have just woken up due to my text; her eyes looked unfocused and her hair that seemed like it should otherwise be straight was kinked in places and flying all over the place. She brushed off the fact that she showed me everything, then asked almost in passing if I wanted to come in and examine her in more detail.

I realized as I pulled up to the fourth address that I recognized the house, and I was actually kind of excited. I checked the list and saw that the fifth delivery was only a few streets over. I zipped over, dropped that food off first, then came back. The delivery instructions specified that I should ring the bell, and I saw the house was old enough to have a physical push-button doorbell that, when pushed, caused an actual bell to ring inside.

I had to pause for a moment when the door opened, both in shock and in relief. Relief, because I knew I'd correctly remembered which house I was at. Shock, because of the state of the woman who answered.

Her dark hair was pulled back in a tight ponytail that showed off the collar around her neck. Another collar formed the top of a harness that came down and formed two triangles around her breasts, each of which were fully exposed and poking through the harness. They weren't large but definitely full enough that tit flesh rested on the bottom strips of leather (or latex, maybe? I didn't check. It also wasn't the first thing on my mind). Some elaborate criss-crossing straps formed a kind of bikini shape, except nothing went between her legs for modesty. Instead, two gold chains clipped to what could be called the belt. The other ends clipped to rings in her labia, pulling them apart and exposing her pussy completely. Despite how uncomfortable the outfit looked, I could tell the exposed pussy was very wet.

"Could, um...could you get your mistress for me?" I asked her when I handed over the pizza.

The imperious lady from my first outing with Amy came to the door with the harnessed girl standing behind her, head down and silent.

"Oh welcome back," she said to me, "Were you too embarrassed to submit to my training with your girl there? Change your mind?"

"Um, no," I said, hopefully strongly enough that there would be no confusion in the woman's mind, "but, um, we were...I think she might be interested."

"Finally get her clothes off and she started begging for it, did she?" the woman asked.

"How-"

The woman rolled her eyes, "You don't get to be as good at this as I am without reading people. I knew last week that girl was a virgin, just like I knew there was no chance of you coming in for a session."

"So, um, should I drop it?" I asked.

"You aren't a natural dom, and a real sub would lose patience with you. Watch; Cunt! Clean your hole!"

The woman behind her immediately folded herself over with her legs splayed out so her ass cheeks were stretched wide. Gripping one of them with one hand, she made the other into a point with all five fingers and pressed them against her asshole. I stood shocked as they began to push inside her. She had to stop when she got to her big knuckles, but she began pounding her hand against her ring and I saw it giving way.

"There, see? A real dom would be impressed or eager before anything else. You're still getting over the shock. But I don't think your girlfriend would play at my level anyway. Unfortunately I've got a list and I can't spare my time on casuals."

"Um," I stammered, a bit desperate, "Do you know Max? She's from the city..."

"Tall girl, rail thin, keeps a...let's say photogenic specimen on her leash?" the woman asked.

"Yeah," I said, my attention robbed when the girl let out a little squeak as her hand disappeared into her ass up to the wrist.

"She'd be a wonderful teacher. Definitely not on my level, but so few are. Have a good evening," she said.

I heard her start to berate her...partner?...but all sound cut off completely when the door closed. I tried not to think about why she needed her house soundproofed. Then it opened again.

"Free word of advice?" she said.

I turned and tried to focus on her face and not the girl who was now bent over on the floor, pulling her ass cheeks wide with her hands.

"Test your girl a bit, make sure you weren't both just eager for a first fuck."

The door closed, leaving me with something to think about, and a really hard cock.

-=-=-=-=-=-

It was still mostly stiff when I got back to Central Pizza and Amy informed me we were both on break. She came out with a personal pizza we were apparently sharing for dinner, and we walked out to her car. It was warm enough we just sat on the back.

"Ohhh, is that because of me?" she said saucily as she grabbed my crotch.

"Uhhh," I replied eloquently as my brain debated honesty to impress her and a lie that might get me laid again.

"Ohhh," she said with a mischievous smile, "spill. What did you run into?"

I told her the stories of the encounters, although I fudged the details on the last one; I didn't feel like telling her I'd asked a stranger about her possibly being a submissive would go over well.

"Seriously? Her whole hand?" Amy asked.

I nodded because my mouth was full of pizza.

"I...I can't even imagine that, I have-"

She cut herself off as she realized she was about to reveal something. She glanced back at me nervously, maybe hoping I hadn't caught it.

The dominatrix's words came back to me. I decided to risk it.

"You what?" I asked.

"Nothing," she said.

Before she could react, I snatched the pizza away and held it back where she couldn't reach.

"Hey!" she objected.

"Tell me," I said. I tried to take the teasing out of my voice and make it sound more like a command.

"No," she said. Her own voice was a bit playful, but I also heard an odd hesitation in it.

I stood up and walked around so I stood in front of her, the pizza held behind my back. Her knees parted to let me stand between them. She also slid forward a little, though I couldn't tell if she did it on purpose.

"Tell me and you get a prize," I said, my voice a little lower.

"I can get more pizza inside," she replied in a more intense tone.

"Who said the prize was pizza?" I asked.

She gasped and her eyes widened. "I can't," she claimed.

I reached out with my free hand and grabbed the front of her pants. She had on jeans that were tight on her legs and ass but a little loose in the waist. That said, her posture pushed the flesh of her tummy down on my fingers, and when I hooked them into the waistband I felt the smooth expanse of skin I knew was above her pussy.

"If you don't tell me, you'll be punished," I said.

"I can still get pizza inside," she said.

"But your uncle will be annoyed if you're late," I said. Then my fingers found the band of her panties. I yanked them up and she gasped again, her eyes flaring.

"I'm not telling you," she said.

I yanked her panties again a few times. I hoped what I was doing was pulling the fabric tight against her pussy, and her reactions looked like it felt good.

"You want more?" I asked, looking deep into her eyes. She nodded and I said, "Undo the button."

Her hand came around frantically and undid the button holding the top of her pants together. With less pressure, I slid my hand down and found the wet heat of her pussy. I slid my finger past her clit but couldn't get it very far into her hole because of the angle. Her response to my intrusion was a moan and a twitch of her hips.

"Tell me," I said.

"No," she said. I pressed with my finger, grinding it against her clit. She bit her bottom lip in that classic move guaranteed to get a guy's attention instantly.

"This doesn't feel like punishment," she said.

"It will if I keep you going until the break's over then leave you wet, hot, and horny before we head back in," I said. I punctuated the sentence by flicking my finger past her button.

"God!" she gasped, "You think you're that good?"

"You think I'm not?"

I was bluffing, mostly. I had seen her cum exactly twice, and the second time I hadn't even been facing her. The first time I was so busy marveling at seeing her mammoth tits and bare pussy I barely registered what her tells were. I couldn't even describe her "O face" if I had to. I was banking on Amy's seeming ignorance of sex and my own bravado. Maybe all that made me an asshole, I don't know.

I do know it made Amy hot. She was practically humping my hand after a few minutes, and one of her hands had a death grip on my arm.

"Please," she said, "Please I want to cum."

"Then you know what you have to do," I said.

"I...I can't," she said, "It's too embarrassing."

"More than squirming around with a horny wet pussy the rest of the night?" I challenged.

She delayed for another minute or so. I showed her the time on my phone, which said we had three minutes to get back.

"I play with my ass in the shower sometimes," she blurted in a rush, "I put a finger up there farther than I need to."

"Cum for me Amy."

Her arms wrapped around mine and she leaned in and moaned into my chest as I felt my hand soak with her juices. Feeling bold, I pulled my hand back and brought it up to her face. She looked back and forth between me and it until I nodded at her. Then she licked my hand. She was hesitant at first, then got more into it when she could see I liked it.

"Is that what I taste like?" she asked. I just nodded.

"Shit," she said, suddenly serious, "Cover for me."

"Huh?" I said, my confident, controlled demeanor from before completely gone as she dropped to the ground and opened the back door to her car. Then she yanked her pants down.

Getting a clue finally, I stood between the door and the shop, looking for anyone approaching or looking over. After what felt like an hour but was probably a minute at most, Amy stood and pushed me out of the way to close her door. She also slid a hand in my pocket along with something else.

"Just for that, you get to keep those, and deal with the fact that you didn't get off at all," she said. Despite trying to sound smug about it, I felt like both of us knew I had won something during that encounter. I just wasn't sure either of us knew exactly what.

-=-=-=-=-=-

I spent most of Sunday morning digging through my room. One of the advantages of leaving dirty clothes hanging around for a while is that I knew the paper card Max handed me two weeks ago was probably still in a pair of pants hanging around. I was decent at getting my shirts and socks into the wash, but I had no concept of the cleanliness of pants unless something obvious had happened, like falling into a mud pit or skidding on grass. Fortunately that meant Max's card was a little mangled but still fully legible. After taking some time to remember how to actually make a phone call with my phone, I got it.

Max herself answered the call, which surprised me for some reason. She seemed excited to hear from me, though she also sounded a bit hesitant when I asked if we could talk somewhere. She suggested a café near the maker lab later that day. I didn't have anything going on (Amy told me family activities again had her booked most of the day).

Max had on another loose tank top displaying a good amount of her ink and no obvious bra; I was pretty sure if she leaned forward more than a little I would be able to see everything. Her pants were skinny capris that left only a little sliver of pale skin between them and her combat boots. We ordered drinks and something to snack on and found a table in the back corner of the café. I explained to her what happened with Amy, both times.

Max looked at me seriously as if she were one of my teachers about to reprimand me. "Jay, listen to me," she said, "you have to confront this with her directly. I know it's really early and you're way more interested in having sex than talking about it at all other than 'can I do this' but you need to slow down. You can seriously fuck someone up playing these games. It's how way too many bad habits or even abusive relationships start."

"Fuck," I muttered, looking away.

"Hey, no, look, you didn't do anything wrong. Actually, you deserve some credit for this; a lot of guys would just take someone like Amy, willing to go along with whatever, and use her as much as they could until she finally broke. You get props for recognizing she might be a sub and for actually asking about it rather than doing something like reading 50 Shades of Grey and figuring you're good to go."

Max gave me a few tips and general ideas, as well as sending me links to some sites with what she said were "real guides on what to do." She stressed again that I should talk to Amy before anything else.

I left conflicted. The whole day had seemed...normal almost. Nobody flashed me or propositioned me. Granted I hadn't been around anyone most of the day but going into the city and walking to the café I could have been accosted by any number of people. I began to wonder if whatever had been happening was wearing off. After all, Saturday had been a lot tamer than usual, Amy's sexuality seemed to be taking a surprising turn, but it wasn't sudden or extreme, and while Max wore a provocative outfit it seemed to fit with her style and personality. Maybe getting involved with Amy had short circuited the whole thing?

Amy messaged me that night saying how she missed me and couldn't get our encounter out of her mind. We chatted for a bit and when I felt like things were winding down I told her we should sit and have a serious talk. She let that message hang on read for a while, long enough that I almost considered trying to call her, as crazy as that was. Finally she came through with an "okay" message, then immediately said she had to sign off and go to bed.

It was late enough that I didn't think it was a complete dodge, but I'd obviously pulled out a conversational nuke by saying "we need to talk." I spent the rest of the night trying to use my C grade in English to come up with sentences that meant the same thing but didn't sound as ominous. Sleep came long before anything like a good idea.