The Deal

"I don't want this drama outshining my wedding, mother," Casey said, concerned that tomorrow might not be the greatest day as we expected it to be.

"I'll make sure it doesn't, sweetie," Alexis said, sounding like her motherly self in private for the first time in ages.

Glancing at my watch, I realized that it was time for us to be heading out. So, before anyone could say anything else to get us sidetracked, I said, "It's getting late. So before we get carried away and miss dinner, I suggest we get going. Three of us have a long night ahead, and I'm sure Tammy wants to start teasing (and possibly seducing) her father. So let's go, the sooner dinner's done, the sooner we can get to fucking."

Three matching looks of 'the party pooper has a point' were directed my way, before the four of us left for dinner.

The dinner was fairly low key, just our moms, my younger sister and the wedding party. My mom and sister were a little perturbed by Alexis' face, now covered in dry, crusty cum, but after I told them that Casey and I weren't making a big deal about it, they let it drop. That didn't stop my sister Jen from making way too obvious puns at Alexis' expense throughout the meal; everyone got a chuckle out of that, except mom who wouldn't say anything about the dirty jokes, but would give Jen a look of great reproach. Honestly, both of them were laying it on a little thick, I thought. None of us really made a fuss about the fact that Alexis' face was covered in dry cum, and she was laughing along to, and adding to, Jen's jokes.

As we finished our meals, I felt myself starting to get anxious. I had a lot to live up to, and the pressure was on. Mostly from myself, I knew that Slut-Alexis would enjoy herself no matter what, but it was still there. Seeing everyone off for the night, me, Casey, Alexis and Terry stayed behind to make sure everything was taken care of with regards to tonight's, as well as tomorrow's, dinner. Tammy, being the only one who knew of tonight's festivities, told us all to have fun and that she wanted all the details later.

As we walked to our cars, I felt the first real pang of jealousy that I'd ever had in my relationship with Casey. And she seemed to feel it too, as we both hung back a moment from getting in. Pulling her to me, I hugged her tight, as she did me. Pulling back slightly, I leaned in to place a gentle but passionate kiss on her lips. She was soon reciprocating, but we only kissed for about thirty seconds.

I opened my eyes to see her beautiful blue eyes, staring back at me with more love than I could recall seeing in them. "I love you, Derrik" she said to me quietly. "You, and you alone. And no amount of pleasure or torture will every change that. He has me for a few hours; you laid claim to me the moment we met, and I've never wanted that to change." I couldn't contain myself, and launched my lips upon hers as she reassured me. Pulling away, the love in her eyes had been replaced by the more typical kinky mischievousness. "Now, go fuck my Mommy-Slut into oblivion."

Smiling, I gave her a final peck on the lips as I said, "I love you too; and I hope you have as good a time tonight as I will."

"Trust me, Terry won't know what hit him." I had a sudden bout of worry for my best friend as I watched that devious smile spread across her face as she got into his car, her overnight bag in hand.

But I couldn't think about it too long as a voice behind me whined, "Master Derrik, can we please go? My pussy is leaking so much that it's going to ruin my dress permanently if I don't get it off soon."

Sliding into the driver's seat, I reached over and got my hand around her throat, holding it tight. Growling in her ear, I said, "I don't care about your dress, Whore-Mother-in-Law-Slut! And since this is your car, I don't care if your tasty juices stain the leather seats and permanently give them the smell of your twat as it's begging for my or your brother's cock to pound it until you need wipers on the inside more than the outside in a hurricane. Remember, you're still my slut for the night, and tomorrow morning. If you don't behave, I could still tell you that you're no longer allowed to submit to Master Nick."

Her face was pure fear as I said this. "Now, I promised you ten orgasms tonight, and you've been a good pet these last few months, so I'm going to give you a reward. Once we're out of the parking lot, you may take my cock out and hold it in your hand for the first time. And as you hold it with one hand, your other hand is going to be plugging that soaked cunt of yours as you tell me how turned on you got exchanging innuendos with my sister. You will not jack me off, just hold my dick; and only once we pull into your driveway will you be allowed to cum." With an extra squeeze to her throat for emphasis, I asked, "Do I make myself clear, my Whore-Mother-in-Law-Slut?"

Nodding, she opened her mouth to speak, but my hand around her throat prevented that. Letting go, I started the car as she said, "Yes, Master Derrik, I understand." Pulling her dress up over her hips, I noticed that her desperation had led her to forgo her panties, revealing the smoothness of her shaved pussy. Reaching into the middle compartment under the armrest, Alexis pulled out a large handful of napkins and placed them on the seat below her. "I've found a new freedom in being a slut and not hiding that fact from everyone," she explained seeing me looking at her actions with a raised eyebrow. "That being said, the less people that know that fact about me, the easier my life will be. So, if I can hide some of it so I don't have to explain, then I will try."

I didn't say anything to this as we reached the road and her hands darted towards my fly to release my dick. We both moaned as she freed it and held it firmly in her grip for the first time. There was a wet squelch as she stuffed three fingers into her dripping pussy for a second, before she pulled them out and offered them to me. "Can I tempt my master into having the first taste of my tasty twat of the night?" she teased in a sexy little girl voice.

One by one, I sucked her fingers into my mouth, tasting her sweetness. Once I'd sucked each finger clean, she returned them to her cunt and began teasing herself as she said, "Maybe tomorrow I should leave you with a noticeable layer of my cum on your face, so that your Mommy could have a heart attack and aneurism as she smells and sees pussy juice all over your face and knows that its not Casey's because everyone knows that you won't be seeing her until she's walking down the aisle tomorrow. But of course, Casey will know that it's my juices, and be all the more hungrier to kiss you just to taste them. And I'm sure that little Jenny will have all the naughty innuendos to try and roast you with. 'Oh brother, isn't it a little early for pie?' 'Why would you eat fish tacos for breakfast on your wedding day?' 'Are you using the same facial cream Alexis was using yesterday?' 'It's wedding cake that's supposed to get shoved in your face, big brother, not wedding pie!'"

I let out a groan as I imagined my cute baby sister saying these things to me, with a look of faux innocence on her face but mischief blazing in her eyes, and felt my cock lurch in Alexis' hand. "Oh, did that turn you on, big brother?" she teased, rhythmically squeezing my cock now to add some form of stimulation. "What if I got dirtier? What if I whispered in your ear, that it got my pussy wet to see and smell your face covered in girl cum like that. I didn't even know that was a thing people did, cum walks but with pussy juice. So, who had her thighs wrapped around your head brother; who'd you make squirt like Old Faithful, all over your face? Cuz I know it wasn't Casey, it doesn't smell like her cum, not entirely. It honestly smells a bit like mom's pussy; but I know it's not hers, cuz I was snacking on it all morning long, and I don't recall that big tentpole being there, because if it was, I know that we both would have been screaming loud enough to have the neighbours call the cops, but the only things being murdered would have been our tight, juicy pussies."

I'd plan on driving slow, trying to tease Alexis with the lack of speed and have her build to a higher plateau, but her words had given me both a raging boner and a lead foot as we were now pulling into her driveway. Turning the car off, I roughly grabbed a fistful of her hair and brought it down to my cock. "Fuck, Jenny! Let's see if that mouth of yours is as good at relieving the pressure it knows how to build up." I was lost in the fantasy, forgetting momentarily that it was Alexis and not my sister who was about to blow me.

"Anything for you, big brother; it's your wedding day after all," she said, before taking me to the root in a single gulp. I felt her throat muscles contract and release all along the half of my cock that was in her throat, making it feel as if she was giving me a handjob as she swallowed. Thirty seconds or an eternity later, she pulled off and said, "Do you want to fuck my face, big brother? You feel so tense, torn between not hurting your sweet, baby sister and pounding away at my mouth to relieve these full balls. I'm not as innocent as you think brother; the hazing to get into my sorority was way worse than this: they had me get air tight three times a night for a week straight, by the end of which, all the boys said I was the best and tightest fuck they'd had in years. So go ahead, big brother, use your slut sister's mouth."

That was all it took. Bringing my other hand down so that both were now holding fistfuls of hair, I did what she asked and started to face fuck her. The wet sounds of my cock disappearing and reappearing from her throat twice every 1.5 seconds, along with the sound of my balls hitting the side of her face and our moans, was definitely loud enough to be heard outside. When Alexis made a particularly loud squealing moan, I thought I heard a new sound, like water landing on a tarp, and I realized that she'd just came, or should I say squirted.

Still lost in the lust imagining that this was my sister doing this to me, I said, "Did you just squirt, from getting your face fucked, sis? That's so fucking hot!" Stopping myself from pushing her down further on my steel hard cock, I pulled her face off of my dick. Over the sounds of her heavy breathing I asked, "Where do you want my load, Jenny? Face or mouth? Cuz I'm so close to bursting, the next thing out of your slutty mouth just might set me off."

"Oh really, big brother," she said, her breathing returning to normal. "Is it my words, or the thought of fucking me that's got you ready to blow that huge load boiling in your balls? The load I want you to shoot down my throat so that I can compare your taste to our equally slutty and even fouler mouthed Mommy. Our Mommy who has repeatedly begged me to go down on her whenever we knew you were coming over so that you'd catch us and break our beds as you fucked us into submission. She'l-"

I didn't get to hear the rest of what she said as I pulled her face back to my cock and started to spew spurt after spurt of cum into her mouth, along her tongue and down her throat. For a solid 45 seconds, I felt myself fill her mouth before she swallowed what was there, only to be filled again. When I'd finally stopped cumming, she continued to suck me, trying to drain any last remnants of my splooge. When she pulled herself back up, I was surprised and slightly disappointed to see the face of my mother-in-law Alexis and not that of my sister Jen. "That was hot," I said between breaths as my heartrate tried to level out. "But I don't think I'll be able to look my sister in the eye tomorrow, after that little stunt. And for that, I'm going to punish you, Slut Alexis."

"Are you going to spank me, Master Derrik? It's been so long since I've had a good spanking," she teased.

"Are you still leaking slut?" I asked, ignoring her question, but filing it away for later.

"Of course, Master; I haven't been able to stop dripping my tasty twat juice since I woke up this morning and remembered that I got to fuck you and suck Master Nick off and wear his cum all day." The look of happiness in her eyes was astounding; she'd wanted nothing more than to be her brother's pet her entire life and she was now on the cusp of living that dream.

"Good," I said, "because part one of your punishment is that you're going to get rid of those napkins and wipe your juices all along your seat and not stop until the stain is noticeable. And if it doesn't smell like your pussy in the morning, you are going to march up to your sister-in-law and beg her to let you fuck her husband, promising to do anything and everything in your power to make it up to her and I mean anything. So get rubbing slut!"

With an awkward swish of her arm, she threw the napkins to the floor and started to rub her dripping pussy all over the seat. At first, she was just trying to get it everywhere by any means necessary, so there was a lot of hip thrashing and jerking; but after about a minute or so, she started to conserve her energy and doing a set pattern that covered most of the seat. She'd start with concentric circles that spiraled inward from the corners to the centre and then reversed, before she used her lips like a pen with their leaking juice as the ink and drew the six-pointed Atlantean star. For about five minutes, she repeated this pattern as she whimpered from the tease the constant friction was giving her until she finally begged, "Please Master! Please, can I stop? Please can I cum? I'm so sensitive I could cum just from your permission and name calling like the worthless slut I am."

"I don't know if you really want that, Slut," I teased, as she let out a whine. Cutting her off before she could protest how she did want to cum, I clarified, "Because the second part of your punishment for tainting the image of my sister for me tomorrow is getting exactly what I promised you: 10 orgasms, no more, no less, for our time together. You've already cum once while you were blowing me; do you really want to waste another while sitting in your car before I've even begun to fuck you properly?"

Whining like a kicked puppy left out in the rain, she said, "That's awfully mean, Master." Using her asscheeks, she rubbed in and spread around the copious amounts of cunt juice that she'd been leaking onto the seat for the past few minutes. "We're going to have barely started before I reach ten, given how turned on I am."

With my slightly wilted cock still hanging out, I got out of the car and made my way inside. Alexis was barely a step behind me, her dress still pulled up over her hips. "Well, then I guess you'll just have to deny yourself from cumming too much. This is now a punishment, remember, and should you cum more than 10 times before I'm finished with you tomorrow morning, your punishment will be even more severe. Are we clear on that, my Whore-Mother-in-Law-Slut?"

"Yes Master," she said in a defeated tone.

Giving a swift slap to her bare ass, I motioned her upstairs. "Go wash that cum off your face and get ready for me in your room. You have 5 minutes."

"How do you want me, Master Derrik?" she asked.

"I want you handcuffed to your headboard, with a blindfold on and your sexy legs spread so I can just slide up and start to fuck you," I said after a moment's thought.

Squealing excitedly, she didn't respond and just climbed the stairs.

*

Casey felt an uneasiness that she had never felt before with regards to sex as Terry pulled his car out of the parking lot. Before revealing herself to be the slut she now was, her mother had told her that Derrik had always been there to hold her hand, but he wasn't there now. Pushing her momentary fears down, she turned to her fiancé's best friend and asked him, "So, Derrik hasn't told you anything about tonight, right?"

"Not really," he replied, keeping his eyes on the road. "He just said that this was for you and to go along with whatever you were wanting to do. What are your plans for tonight anyway?" he asked, finally glancing at her.

"Well," Casey said, as her daydreams from the past week all came flooding into her head. "To start off, I thought I'd give you road head while you drove home, and then once we were inside, I wanted to do a little roleplaying." Not waiting for his response, Casey reached across to his crotch and deftly opened his pants with one hand. When he sprung out, nearly fully hard, she held back a gasp as she saw and felt that Terry was clearly longer than Derrik by a couple of inches. "Not bad," she purred as she lowered her mouth and engulfed half his cock. Immediately, she began to bob her head as she sucked skillfully at his cock. By the time she was about a minute into her blowjob, she had the entirety of his cock in her mouth. And judging from the sounds of his whimpering, he was close to cumming.

"FFFFFFFFUUUCCCCKKK," he groaned, as he jerked the car slightly to keep it straight. "Fuck your mouth is divine, Casey!" Hearing this, she doubled her efforts and could feel the telltale jerking of his cock as it got ready to unload in her hot, wet mouth. "Yes, yes, yes, yesyesyes...FUCK! Cumming!" Terry cried out as rope after rope of cum filled her mouth. He didn't cum as much as Derrik, nor some of the other men that had shared their bed, and his cum wasn't as tasty. Casey wasn't sure how she felt about this in the moment. Big picture, she was happy, this put all her lingering doubts to rest: Derrik was clearly the better man. But she had hoped to have more than just his big cock as a consolation prize for the night. Having sucked the last drops from his cock, Casey sat up. "Fuck, Derrik is the luckiest bastard in the world, if you even do half of that to him whenever you have sex!" Terry said, panting as he pulled his car into his driveway.

Smiling at his praise, Casey seductively said, "You don't know the half of it, Big Boy. That was just my standard, half-assed blowjob. What I give Derrik is much better." Not waiting for a response, she got out of the car and started walking towards his house. Seeing him rushing to catch up, Casey held up her bag and asked, "Anywhere I can change?"

As he opened the door for her, Terry nodded. "My bedroom has an ensuite. Do you want me in anything?"

Nodding as they made their way to the bedroom, Casey said, "I want you in your regular work clothes, Mr. Nicolls." The use of his last name, should have informed him that they were going to be roleplaying in his school setting. "Once I'm ready, I'll knock on the door and we can begin," she explained. "You've given me detention." Locking the door to ensure that Terry didn't sneak a peek beforehand, Casey set about preparing.

Slipping out of her cocktail dress, she pulled out the clothes she'd gotten specifically for tonight: a school uniform from the one Terry taught at, a pair of Hello Kitty half-thong panties, white knee-high socks and a pair of black flats that had a buckle strap wrap over the tops of her feet. Quickly dressing herself, Casey turned to the mirror and started to braid her hair into a pair of pigtails. Once that was done, she quickly put on some eye shadow and lip gloss to make her look like the hottest high schooler in town. Before stepping back out into the bedroom, she took a quick selfie to show Derrik and her mother later.

Ever since Derrik had explained his plan for tonight to Terry and Terry had accepted his duties as best man, Casey had been formulating this scenario in her head. Pulling up the bookmarked tab on her phone that showed the school's faculty, she quickly glanced over the names to make sure that she would be as authentic as possible. Taking a moment to breathe and get herself into character, Casey turned the lock on the door before pushing it open and walking into the bedroom. "OMG Mr. Nicolls, I'm so sorry," she said in a slightly higher pitched voice that she hoped made her sound younger. "I kept trying to tell Ms. Frost that you gave me detention; but once you get her started on taking risks with your writing, it's impossible to stop her. And it's like, so rude, to just walk away when someone's talking to you like that, all passionate and stuff. And besides you, she's like my favourite teacher, so I don't want to upset her, y'know?"