The Deal

"Yes, Casey, I know what you mean," Terry responded affectionately. "Ms. Frost is a whirlwind when she gets passionate about something, and I commend you on not wanting to upset her in such a state." Casey gave a small, prideful smile at the praise. "However," Terry continued in a harsher, more authoritative tone, "that does not excuse you from the responsibility of the detention I gave you this morning for being so disruptive in my class."

"But Mr. Nicolls," Casey whined as if she was fifteen and had just been told she couldn't go hang out with her friends. "I wasn't doing anything! I was just practicing my shading like you said to do."

"Oh, I agree, you were shading your work." The smirk on his face let Casey know that she was about to be thrown for a fun loop. "But when said 'work' is an explicit drawing boarding on pornographic depiction of two of your classmates having sex, I think calling it distracting is the nicest thing I could have done. What do you think would have happened if someone other than me had seen that? How do you think Ms. Fields would react to seeing you, an upperclassman, drawing her, a sophomore, having quite rigorous sex with someone who isn't her boyfriend? You should be thanking me that I'm not reporting this to the principal or the police, Casey. This could have really gotten you into some serious trouble." Pointing to the desk in the opposite corner of the too big for a single man bedroom, Terry continued. "You're a good girl, Casey, and I don't want to see you throw your life away over something as stupid as a Rule34 drawing. I want you to write the lines 'I will not draw NSFW art at school' as many times as you can, for the next half hour. Hopefully by then you'll have realized your mistakes and we can forget this ever happened."

Head hanging in shame, Casey walked to the desk where she found a pencil and some paper. After writing the same thing for about a minute, Casey decided to take her full leap into the roleplay that Terry had given her and kick things into gear. While she wasn't as good an artist as Terry, she'd taken some classes in both high school and college and had enjoyed drawing since she was a child. Using the rest of the 30 minutes that Terry actually just stood a few feet away to depict the two of them having sex doggystyle while he slapped her ass in punishment for breaking the rules, Casey felt herself get wet in anticipation.

Just as she was putting the finishing touches on the drawing, Terry said, "Ok times up! Bring me your sheet and show me what you've managed to complete." Feigning shame, Casey got up and handed him the pieces of paper, with the lines on top. Keeping her head down as he inspected her work, Casey knew immediately when he found her drawing, not only from the gasp, but with how his cock stiffened quickly in his pants. "Casey, this-this is most inappropriate!" he exclaimed in false indignation.

Looking up at him over her glasses with one of her sexiest expressions, she said in a husky whisper, "But you still find it hot." Not leaving him a moment to react, she slid her body up to his and began to rub herself on him. "Oh, Mr. Nicolls, you don't know how often I diddle myself to the thought of you bending me over your desk and really making me earn the 'A's you're always giving me. I'd do it, you know; I'd strip down to my cute Hello Kitty panties, bend over your desk, and let you fuck my tight teenage holes until I'm nothing but a sloppy mess," she whispered in his ear, feeling his long cock twitch excitedly at her words.

"I wanna feel that big cock pull my soaked panties down to my knees before it pries my legs apart and you thrust it up into my jailbait twat. OOOOOHHHHH Mr. Nicolls, my white panties are so wet thinking about you, I'd bet that they're see-through." Stepping back for a moment, Casey lifted her skirt to show off her pussy juice-soaked panties to her 'teacher'. "I can smell how soaked I am, Mr. Nicolls; this is what you do to all us girls. In the locker room, or at parties, whenever we get talking about our biggest turn-ons, the thought of you bending us over your desk and just taking us with that big cock of yours always gets a collective moan as we all have a minigasm just from the image alone." Dropping to her knees, Casey deftly pulled out the cock that she'd just praised. Acting mesmerized she said, "It's so big, Mr. Nicolls...I can't wait to feel it stretching my little pussy. I can't wait to be fucked by a real man."

Terry let out a loud, satisfied groan as she took him into her throat. Whereas her earlier blowjob had been mainly done to take the edge off, this time Casey took her time to properly worship the cock before her. Inch by inch, she lovingly swallowed and sucked Terry's dick into her throat. "FFFFFFUUUUUCCCCKKKKKK!" he moaned once she had all ten inches in her throat. "How can a 17-year-old be this good at blowjobs?" he asked, keeping the roleplay going. Grabbing a hold of her braided pigtails, Terry started to pump her head up and down his cock. "Jesus, Mary and Joseph Casey; your mouth could give all the whores in Babylon a run for their money, and that included the titular Whore herself!"

Pulling herself off his dick with a loud pop, Casey licked the length before she looked up to him with a confident yet bashful look. "Thanks Mr. Nicolls," she said demurely. "But you should really thank Principal Black, she taught me everything she knew when I caught her fucking the McClary twins," Casey added to the tale by referencing the wide-spread rumour that the former kindergarten teacher had been seen more than just flirting with a former student and his sister shortly before becoming principal. "But I'm glad you like my mouth and throat so much." Standing up and walking back over to the desk, Casey bent over and looked back at Terry with a sexy, teasing smoulder. "But wouldn't you like to see what else she taught me?" she taunted flipping her criminally short skirt up and exposing her half thong panty-covered ass.

Whimpering a moan of longing, Terry was on her in a second. As his hands roamed over her ass, Casey cooed her approval. As he started to thrust at her erratically, Casey wondered if she'd gone too far and played into a fantasy he'd been having for a while. As she was about to turn to look and see what he was doing, Terry said, "I'm sorry for the delay, but I believe that you mentioned something about my big cock pulling your panties down and prying your legs open before I fucked you into a gooey mess on my desk." As he finished explaining, his dick finally hooked into her panties and she felt him rub across her soaked slit and causing both of them to groan in pleasure.

"Finally," he said as he knelt down, pulling her panties down with his dick as he did. "You can't know how long I've wanted to do this Casey," he said as he stood and placed the tip of his cock at the entrance to her pussy. "Ever since you came up to me to register for your freshmen art class, and you showed me your fanart of yourself as Meera from Aquaman. And as I complimented your work, I saw the look in your eyes that screamed that how every word in praise I gave to you made you wetter and wetter." Sliding his length into her depths caused Casey to moan in pleasure. "Oh Casey," he moaned. "Your teenage pussy is so tight, Casey. I think it's the tightest pussy I've ever fucked."

Casey felt her pussy get wetter at this praise. Deciding to make this even hotter, she thought of the gift she almost gave to Terry back when they first met. "You didn't just make me wet that day, Mr. Nicolls, you took my virginity. I went home and stole my mom's vibrator and shoved it up my cunt as I thought of this moment, when you became the first man to stick his cock into my tight, tasty, teenage twat!" Wiggling her hips to signal that he should move she continued in a sexy baby voiced plea, "Now, you promised me that you'd make a gooey mess of my juicy pussy, Mr. Nicolls. Please fuck me; fuck me like we've both wanted you to since freshmen registration."

And then he was fucking her and Casey couldn't concentrate enough to get the words out. The sounds of the wet slaps of his hips against her ass and her wordless cries of ecstasy were all that reverberated around the room. Casey clung to the desk for dear life as Terry fucked her faster than she'd ever been fucked in her life. The delicious sting that was his pelvis smashing into her ass, making it red from his speed and ferocity, made her clit throb with need as it continuously was slammed into the plastic wood of the desk.

And much before she was ready, Casey felt an explosive orgasm descend upon her from the heavens on high. "CCCCCCUUUUUUMMMMMMMIIIIIINNNNGGGGG!" she wailed as her pussy tightened enough around Terry's member to cause him to pause and let her breathe for a moment.

"So...Fucking...Tight!" Terry wheezed out. "Fuck your pussy is so fucking tight, Casey. But fuck, if your constant squirting on my cock as I fucked you into that drooling mess you drew yourself as, wasn't the hottest thing, I don't know what would be." He'd started to slowly thrust half his length forcibly into Casey's quivering quim.

Too weak to do much besides moan, she just leaned on the desk as she took the pounding. "OH Mr. Nicolls," she moaned, trying to keep the roleplay going some more. "Once I get home and let all the girls know how good you fucked me tonight, you're going to have a line of every girl and woman in town at your office door. But if you think I'm going to share you until I'm swollen with your baby or dead in the grave, you've got another thing coming." She felt Terry twitch at the mention of her being pregnant. "Oh, did you like the mental image of me, belly swollen from your baby, riding your big cock in my prom dress as we fuck like animals on the gym floor after everyone's gone home; or what if we snuck away to the office, turned on the PA system and you fuck my tight, little pussy for all those at prom to hear." Clearly turned on by her comments, Terry began to pound into her faster, but still as forcibly as before. "Oh, yes Mr. Nicolls, fuck me harder! Fuck me and cum in my teenage twat and we can make those fantasies a reality."

As she finished talking/taunting Terry, he began to pump into with a faster and faster rhythm, but never lost the force with which he was pounding all ten inches into her tight twat. Casey knew that it was only a matter of time before he blew his load in her, so she tried to hold off her orgasm until she felt him unload in her. "Fuck, your pussy is perfect, Casey!" he said, as his thrusting became more uncontrolled and she felt him start to swell.

Knowing that he was a hairsbreadth away from cumming the hardest he'd ever cum in his life, Casey went for the kill. "Oh Mr. Nicolls, you fuck me so good! If you fuck a baby into me right now, I'll invite Kimmie Scarrow to join us the next time you fuck me."

That did it. The mention of Terry's first favourite student who'd just graduated the previous June, and who Casey was somewhat suspicious of him having a crush on, caused him to blow his load into her with a mighty roar which in turn caused her to cum as well. As they recovered from their mutual orgasms, Terry leaning on top of her and both of them hoping that the desk was sturdier than it looked, Casey gave a small laugh. "What's so funny?" Terry asked.

Looking over her shoulder at him, Casey simply said, "You." Seeing his continued look of confusion, she elaborated. "You totally want to fuck your former student," she accused as she rolled out from under him. "Don't deny it, you came as soon as I said her name and implied we'd have a threesome. I get that she's hot in a 'cute nerd' type of way, but since you started teaching, you haven't been able to shut up about her. I'm curious, what is it about her that gets your motor running like nothing else?"

Sighing, Terry got up and flopped himself on his bed. "This is probably going to come out wrong, but she honestly reminds me a lot of you. Or at least, what I think you were like in high school: reserved, intelligent, funny, but there's a slut just dying to get out. Or, at least, that's the impression she gave me. She tried so hard in my classes and was always eager to try and impress me with her art. And in all honesty, she's quite talented; which is sexy in and of itself. But despite all that, I think it really goes back to when we first met. I was heading to the bathroom while my first class of the day was working on the assignment I'd given them, and she was just coming out. Neither of us were paying attention to where we were going as we thought that the halls would be empty at that time of day, and we ran into each other.

"What happened next is straight from an anime, I swear. She bounced off me and fell back, and her skirt rose up and she inadvertently flashed me her white Hello Kitty panties. She was about to yell at me until she looked up and saw me. I swear, I saw the hearts and the bubbly backsplash in her eyes as she looked at me for a moment, before realizing her clothing situation. Both of us blushed up a storm, and said an awkward sorry before heading our separate ways. When she walked into my third period class, she froze in embarrassed fear for a second before coming up to me and introducing herself and apologizing again for her behaviour earlier.

"I don't really know why I can't seem to get her out of my head," Terry seemed to conclude. "Since I'm no longer her teacher, it's better now; but the last couple years have been really hard. I know I shouldn't want her, but I do." Sitting up, he looked to Casey with the most serious face he'd worn all night. "You can't tell anyone I said that, not even Derrik."

Sitting up herself, Casey motioned as she said, "Cross my heart." A long silence fell between them as they collected themselves. Finally standing up, she made her way over to the bag that she'd brought with her and reached inside. "Remind me after dinner tomorrow that I have a special gift for you." Not letting him ask about what she just said, Casey turned back to Terry with an evil glint in her eye as she held up and opened the collapsible riding crop that she'd brought with her. "For round two, I had something a bit more extreme in mind," she said as she snapped the crop into her hand menacingly.

*

As I plunged my dick into Alexis, and she squealed about how she wanted to cum, and that her punishment was unfair, I started to gain speed as I attempted to push her over the edge yet again. She'd already cum three times in the hour that I'd been fucking her, bring her total up to four out of the ten that I'd promised her. Using more power than speed, I was slamming into her surprisingly tight cunt from behind. Feeling my balls begin to tighten, I slowed down even further as I leaned forward so my lips were at her ear, I reached around with my hands and filled them with her tits. "I'm close to cumming, Slut Alexis. And since your pussy is so tight and tasty, and your mouth nearly as dirty as your daughter's, I'm going to make you a deal. If you promise to stop your whining and instead use your tongue to turn me on so that we can cum together, I'll lift your orgasm restrictions for the rest of our time together."

Hearing this caused Alexis to squeal excitedly, so I pinched her nipples with my fingernails to bring her back to reality. "If however, you do not get me to cum in the next five minutes, I will still lift your restrictions; but for every orgasm you have after number ten, you will have to wait one month before you can submit yourself to your brother. And I will use every trick that I know to draw them out of you." Stopping my thrusting, I waited until she was looking back at me as I asked, "Do you understand the deal, my Whore-Mother-in-Law-Slut?"

"Yes, Master," she said nodding.

"Good." I started to thrust my hips again, still slowly but with as much strength as I could muster from my bent over position. "Just one more rule before you start using that wicked tongue to turn me on and make me cum deep in your tight pussy: since you got yourself in trouble by making me get off to thoughts of my sister, all mention of incest is off. That means no mentioning your daughter, brother, niece or my sister and mother." Rocking my hips a bit faster, I started the timer. "Your five minutes, starts now! Remember, we have to cum together."

"OH Fuck, Master! You fuck me so good! You're like my own sex god! You're a much better fuck than my ex-husband!" she half moaned/half panted.

"Of course, I'm a better fuck than that alcoholic slob!" I said, practically insulted that the comparison needed to be made. "Insulting me like that isn't going to get me off in under five minutes; I'm not a worthless whore like you," I teased, feeling her pussy tighten as I called her names.

"Sorry Master, it's just really hard to be nasty when I can't mention all the nasty images in my head that turn me on to the point where I could probably squirt on command."

Now that was a sexy thought. But outside of my cock flinching and picking up a bit more speed, all I said was "Three and a half minutes!"

"Would you punish me, Master, if tomorrow I walked your bride down the aisle in nothing but the cum that your entire wedding party covered me with? What if, I squirted over the two of you as you said your vows and kissed your bride? Would you be able to resist just taking all us bridesmaids and fucking us with your big, hard cock before forcing your cum soaked dick down your wife's throat now that it's covered in the pussy and ass juices of her bridesmaids?"

These images were indeed very stimulating, and had me just about ready to pop. But I wanted to push her to the brink. "Seventy seconds!"

"When you get back from your honeymoon, I'll have the sexiest nun tied up in your bed, begging you to fuck her!"

"Thirty!"

"Take me to Disneyland and we'll seduce, fuck and impregnate all the princesses right outside Cinderella's castle for everyone to see!"

"FFFFFUUUUUCCCKKKKK!" I bellowed, that image so tantalizing that I couldn't hold back and felt myself cum like a race horse as Alexis' pussy clamped down on me and I felt cum being forced out of her cunt and splashed against my thighs.

"AAAAAIIIIIIIEEEEEEE!" cried Alexis as we came together. "YesYesYesYes!" All strength seeming to have been taken by her orgasm, she flopped onto the bed. Unwilling to leave the tight warmth of her delectable twat just yet, I dropped down on top of her.

It wasn't for another few minutes that I reluctantly pulled out of her and rolled us over so that we were facing each other. Looking into her eyes, I gave a small chuckle. "I'm impressed Alexis; that Disneyland idea is really kinky and definitely something that's now on my bucket list. Or at least, the version of it where you, Casey and me try and seduce either a Belle or Aurora. While I agree that having an all-out gangbang with me at the centre of all those princesses would be fantastic to experience, I think Walt himself would dethaw his head just to personally ban me from anything associated with Disney ever again if we even tried such a thing."

"You'd be a legend everyone would aspire to, Master. To have fucked all the princesses should be on every Disney pervert's sexual bucket list. Fuck, I wouldn't mind being double teamed by Eric and Flynn Rider while I eat out Elsa." She'd been lightly brushing her fingers along my shaft as she said all this, and felt it flinch and begin to harden as the mental image of this took root in my mind. "Clearly, someone else wants that just as much as I do," she teased with a smile.

"If we can't get you that while I'm fucking Belle and Aurora, I'm sure me, Nick and Casey would love to re-enact it for you," I sincerely offered back to her. Now back at full mast, I rolled myself over and propped her leg up on my shoulder. Sliding myself into her gooey pussy and causing her to moan, "You did very well, my Whore-Mother-in-Law-Slut. You made me cum within the time limit, so as promised, you can cum as much as you can for the rest of the night and tomorrow morning."