Double or Nothing

Ms. Green doesn't end up leaving even after a full fifteen minutes of nothing but me draining Ms. Lia's tits dry. My worry that it would take the weekend to reach 200 orgasms proves quite silly: Ms. Lia's body trembled every time she came, and she was shaking like a leaf by the end of it. Ms. Green being incapable of avoiding hitting the same peaks every time meant each was a 2-for-1 special. I've probably about 60 of the 100 I need in the bag by the time Ms. Lia's streams of milk become **** droplets. God I'm full, but it's worth the bloated feeling as I continue to **** my dear teacher.

I'm almost at my own limit once again, but this time I have Ms. Hatts' more generous instruction. After all, I just have to please Ms. Lia by using her tits however I want, and Ms. Lia went and tried to stop me. It's time to test the limits of both those instructions. With Ms. Lia mostly collapsed in her chair, I spin it to have her face me to her right so Ms. Green can see us both. Without warning or explanation (lest that give them time to object), I pull my raging erection out, a droplet of pre-cum already glistening on its tip, before shoving it into the gap between Ms. Lia's tits. Both teachers gasp, but only Ms. Lia is offended enough to start objecting. Even then it's hard to make it out in her raspy, half-dazed voice.

I don't even bother explaining my actions; by now Ms. Lia knows. I reach down and scoop her tits up to have them pointed to the ceiling as they rest on me. Pressing them together around my cock yields less pleasure than porno would have me believe, but watching her barely manage a negative reaction makes up for it. Soon I've got her tits pressed between my stomach and pelvis and her own face... and the head of my cock, barely making it past her monstrous knockers, confirms that familiar, wonderful feeling of a woman's tongue on its tip. Ms. Lia's tongue-lulling state ends the moment she tastes my pre, and her head reels back in rebellion. Unlike Alice, Ms. Lia is under no instruction to suck my cock, even if it is involved in pleasing her breasts... so it's going to take just another push. “If you get me off, Ms. Lia, we can end this tutoring session early.”

“I-I won't! I... hah... hah...!”

Meanwhile, Ms. Green is in a crisis: my own pleasure is now being witnessed by her, and the exquisite tingles and spikes of excitement I get every time I feel Ms. Lia talking against the meat microphone poking at her face is now translating into Ms. Green on top of Ms. Lia's own multiplied arousal. Ms. Green's pants are an absolute gray mess now, and at some point her blouse came down around her shoulders and down to the crooks of her elbows, leaving her full-cup bra visible. What state would she be put in if she felt a male and female orgasm at the same time? I have to find out.

“Oh, I mean you can help make it happen faster... trust me, I'm very close. I will get off... the question is how many more times will I get you to come before I do?”

“I'm not... sure! I- aaah!” Ms. Lia can't lie to me anymore, and certainly not as she and her vicarious partner are sent into another violent fit of further staining their undergarments. I glance at the glass panes in the door, but no one's spying on us; Wednesdays in this classroom seem to be pretty safe for even our cacophonous play, then. I continue crushing Ms. Lia's tits together as fiercely as I can to simulate a nice, tight sex toy. True to her wish, Ms. Lia still doesn't open her mouth and fellate me, but that doesn't mean I don't get the pleasure of feeling my wet tip poke and kiss her mouth, cheek, and tongue with every thrust. Another climax builds and goes in her; then another; and finally, with the third trembling climax in just a couple of minutes, I feel my cockhead slip into her open mouth.

I'm done asking. Letting her tits remain pressed together with my forearms, I grab Ms. Lia's head and secure her where the head of my dick remains within her lips as it begins to swell with my own orgasm. Ms. Lia is too in her throes to pull away or, God help me, bite down; Ms. Green, feeling both our orgasms build, seals her mouth with both hands as she screams into them with all her might while her legs wrap around her chair legs to try and control the bucking of her hips. My balls clench, the pleasure in my core spikes, and I finally, gracelessly, blast a hefty spoonful of baby batter to the back of my English teacher's throat. She jerks violently from me, barely sparing my cock as she begins **** and coughing through the surprise gag reflex, but I'm not done coming. I go back to squeeze her tits painfully against my meat as I jerk my last few pumps off with her flesh, painting her head and hair with fat ropes of built-up seed. All her Harvard grace and dignity is lost on the panting, red, and cum-plastered face of an English teacher absolutely exhausted with her own sexual bliss.

I hear something clatter to the floor and glance to Ms. Green. Her chair has properly fallen backwards, but Erika herself seems largely okay: her body continues to spasm as she moans in gasps. With tears in her eyes and hands tucked under her bra cups, its clear she is lost in her own overwhelming ecstasy.

Withdrawing my softening meat from Ms. Lia, I quietly tuck myself back in my pants as I step away from my coughing, gasping instructor. “As promised, we'll end this session early. I think we've made great progress together.” With a smile, I wait for her to wipe my cum from her lips before reaching for her, pinching her nipples viciously hard, and intercepting her mouth as she cries out from the sudden renewal. I kiss her, openly and without care for the smell of me on her, before releasing her and whispering, “Think of me when you bathe tonight.” Straightening up, I jog over to Ms. Green and reach for her to help her up. “We're done for today, Ms. Green. Are you alright?”

The math teacher just looks up at me in a terrified daze. “What was... that? Is that how... men...?”

Sharp as ever. I offer her a consoling smile before lifting her to her feet. I hug her close as I do so, enjoying the warmth of her lithe body briefly before letting her stand on her own. “I have to take my sister home, so I gotta go. See you both tomorrow, have a great day!” Cheerfully satisfied, I leave the two distressed, tingling professors to think on what just happened. I check my phone: it took just 22 minutes, but that felt like a clean hour was lost. Going to the app, I'm not surprised to find the result:

MASTER OF PLEASURE
Cause 200 orgasms: 171/200. . 25 GEM AWARD.

Almost thirty to go... hmm. With a smile, I stop walking from the class and put my back to the wall just outside... and return to Ms. Lia's buttons. Her and Ms. Green's moans are mostly drowned out thanks to the taxpayer soundproofing of the classroom walls, but it's enough to confirm that I've got some mileage to go. Sneaking closer and glancing through the glass, I keep tapping the Bend Over button and watch as Ms. Green and Ms. Lia fall to the floor in an embrace. Apparently Ms. Green had gone to help Ms. Lia out of her chair (an impossible task, given how exhausted I left her), but now the latter was straddling the former as she bent out of the chair and pinned poor Ms. Green to the ground. The two pressed together meant only more pleasure for Ms. Lia... and thus more pleasure for Ms. Green, encouraging her to continue pressing and... well, you get the picture. I throw in a few breast-squeezings just to get the chain reaction started, and soon Ms. Green is just holding onto Ms. Lia for dear life as the latter continues to milk her dried-out tits onto her colleague. I only barely have to tap the button as I watch the two continue their parasitic pleasure ritual, each too lost to fight this terrible new urge, until I'm sure I've hit the required number.

Later that evening...

True to her word, my sister didn't appear until dinner was almost done for mom and me. It took some willpower not to use the app on mom: she had some very interesting options, sure, but nothing that quite normalized what me and Alice were doing... and nothing that could match Alice's arrangement for me thanks to Hatts. All the same, I'm looking at my phone for most of dinner.

MASTER OF PLEASURE
Cause 200 orgasms: COMPLETE. 25 GEM AWARDED.
Cause 500 orgasms: 225/500. 30 GEM AWARD.

I didn't leave Ms. Green and Ms. Lia alone until I spotted a janitor getting started on the classrooms farthest from theirs. Not wanting Ms. Green to be fired, but having no Custom Girls options to prevent it, I finally relented: Ms. Green eventually pried herself from Ms. Lia, fixed her clothing as best they could be fixed, and sprinted away so fast that I doubt she even noticed me hovering near the classroom. Ms. Lia remained collapsed in her chair... hopefully at least in part meditating on my constant offers. The bitch needed to be brought to heel... and what better way to do it than mold her into being my lover? I don't know if I can get it done with just one weekend, but this app might make it possible.

I accept the gems and look again through my mom's options. A few new ones have appeared, but still nothing to make her accept what me and Alice are up to. She's a vigilant parent, too, so I might have to wait until the evening... maybe even until midnight when 30 gems would become 46. Such are my thoughts as my sister strolls in with her backpack tossed to the ground.

She glances at me with a mix of fear or loathing, but greets us casually enough. “Hey.”

“Hey? You told me you'd be home by six,” my mom scolds her, “and it's almost eight!”

I eat what remains of my chicken parmesan in silent observation... all while looking through Alice's new options for today.

“I'd be back sooner but Dave was taking forever at school!”

“You stayed later at school?” My mom narrows her eyes at me. “Did you get detention again?”

“Not at all: I just had tutoring with Ms. Lia.”

“Tutoring, huh... and she'll tell me that if I call her?”

God only knows what she'd tell my mom if that phone call happened. I do my best not to react, but it comes out shaky, “Y-Yeah.”

“Good... then I'll give her a call tomorrow and confirm it.”

Shit... shit! I don't even see Alice's chart anymore as I enter a panic. What could I do to soften whatever nightmare scenario this causes? I finally get past the panic when I remember who approves of Ms. Hatts commands. “Well, she'll also tell you what we do during the tutoring, but it's because Ms. Hatts told me to.”

“What do you mean?” Mom's eyes narrow accusingly as she probes me.

“Ms. Hatts put Ms. Lia on... an administrative punishment,” I explain with no small hesitation, “and I'm getting community service hours by helping administer that punishment.”

“Oh... well, look at you! Here I thought you'd be stuck rushing to do those for that awful food stand they have for the volleyball games.”

Oh, my youthful, inglorious plans. I had indeed charted a course to be there for the winter games of volleyball, getting my minimum hours in while watching God's greatest sports gift: girls in skimpy clothes jumping up and down to bounce a ball back and forth. I'd have been fuming to lose that opportunity before... but well, things sure have changed since then. “Yeah, this is tougher work, but it'll look good for college applications.”

“I'm... well, I'm really surprised- err, proud of you, David! It sounds like you're turning a new leaf.”

I return mom's beaming smile and even turn it to Alice... whose sisterly loathing is on high. “Sounds like a cushy gig,” Alice all but spits between hasty bites of cold pasta.

“So, when I call Ms. Lia tomorrow, what sort of 'punishment' should I expect to hear about?”

My smile can't help but slip from me. I'm still on the hook, then... well, the app hasn't given me much reason to doubt it yet! “Well, Ms. Hatts ordered me to **** Ms. Lia as punishment for all the times Ms. Lia's been masturbating at school.”

A torturously long pause descends onto the table. My sister's fork clatters from her hand onto the plate. My mother's expression drops... and then winces, and then settles on confusion. Alice doesn't seem confused at all: her eyes are quite simply bulging out of her head. Ah, right: parents would never object... but who said anything about students? Finally, my mom breaks the silence, “Well, that is wholly unacceptable behavior... oh God, in front of her students?! To think I thought she was better than that! Was it in front of- oh no, did you two see this?!”

I silently nod, but my sister doesn't quite absorb the question.

“Well, I know you'll follow Ms. Hatts instructions to the letter... goodness...”

“You're finger-fucking our English teacher for community service hours?!”

“Alice! Language-!”

“Not yet; I just have to play with her tits.”

“Dave! Language!”

“Sorry... breasts.”

“Un-fucking-believable-!”

“Alice, if you want to be anywhere but home this weekend, you will clean up your language!”

“Fu... Fine,” Alice quickly amends, “I've lost my appetite anyways. I'm going to take a shower.”

As Alice leaves in a huff, I'm left in an uncomfortable silence with my mom as she looks me over. Finally, she breaks that silence with a **** smile and a whisper, “I know you're already a man, so it's probably more surprising than traumatic, but... well, you know her behavior isn't normal, so just carry on this work. In the meantime... well, I think a sternly-worded letter to the principal is due.”

“Don't worry mom, I've got a feeling she really understands her mistake and won't do it again.” I give her a big, joyous smile... an earnest one, given that I can't believe I got away with this. She gives me a gentle pat on my head and then gets out of her chair to give me a generous hug. I sigh with relief as I lean my head into her cleavage, enjoying the weight of her breasts against my head. Soon enough, my dear mother.