The Deal

"I'm sorry if this upsets you, Alexis," I continued. "It really wasn't meant to cause you any negative feelings at all. You heard how excited I was by the idea of having sex with you (which, as a side note, I apologize for; I didn't know that Casey called you until she was hanging up and I was mortified that she'd done such a thing to her own mother). I don't know what your love life is like, nor am I claiming any right to know, but from what I've seen in the last five years, you've been lonely since Casey's dad died fifteen years ago. I had hoped that hearing our kinky idea would make you feel sexy and like a woman again, and having such feelings would make you slightly more open to the idea than you were upon first hearing it. I didn't think that you'd want some wild night like what we enacted; I would've tried to have been tender and more romantic than that. Like I said, this wasn't ever about sex, it was about me and Casey showing each other how much we love each other; we were just using other people to express that love."

There was a long silence as Casey and I just looked to her mother, awaiting her judgement and thoughts on what we'd had to say. My nerves were on edge, fearing the worst, but the fact that she wasn't screaming at us had to be a good sign. Alexis took a few calming breaths before she looked at us and said, "It is taking every ounce of control that I have not to be shouting and disowning you both to high Heaven. Dealing with this one piece at a time," she said as she looked to me squarely. "Thank you Derrik, for having more tact than my daughter in this insane situation. Also, your compliments on my sex appeal and attempts to bolster my confidence are appreciated, if shall we say unorthodox in their implementation. Despite my outrage, I'm quite flattered that you're so taken by me; and please know that I've always found you to be a handsome man and a little jealous of Casey for finding someone so perfect for her."

Turning to Casey, I could see some of the anger return to her eyes. "I won't insult us both by asking you not to be such a big slut. The fact that it took you throwing it in my face for me to realize it, proves that you are being discreet with regards to these antics. I know that you're an adult, but I still worry about you gaining a reputation if something goes sideways. As for sleeping with Tammy, let's just go back to me not knowing incest is a word I should associate with either of you."

Alexis took another deep breath, closing her eyes to try and calm and focus her mind. Looking to Casey as if she was searching for something deep within her daughter's mind she continued, "Would you really want me to have sex with him, on the eve of your wedding of all nights? I'm not asking if you're comfortable with the idea, that voicemail made that perfectly clear, but whether it's something you actually want. You say that you're a slut and that you're a pervert, but Derrik's always been there to hold your hand, as it were. I want to know Casey, do you actually want me to sleep with your fiancé in my own bed, away from your watchful eye, where we can have any type of sex we want, where he can fuck me like he did you pretending to be me the other night? Do you want me to be able to say those disgusting words you egged him on with, or some even nastier than that? What if he does something to me that he's never done to you, or he thinks that I'm better at something than you? Derrik holds you in such a high regard, can you stand to fall from the pedestal he's put you on, knowing that your own mother was the one to dethrone you? Are those things what you want, or merely something you're comfortable with having happen?"

The two of them spent a moment, looking into each other's eyes, judging the resolve in each. After about a minute, Casey nodded. "Yes mother, that is something I want. I want you to let loose and feel the rapture that is my husband-to-be fucking you into oblivion while you scream obscenities that turn the both of you on further. I want him to tell me as we dance our first dance that you surpassed the bar I've set for him in any and all sexual fields, so that I can challenge myself to outdo you while we're on our honeymoon. But most of all, mother," Casey said, that sexy triumphant smile ghosting her lips. "What I want most of all out of this arrangement is for it not to be a one-off; I want you to join us once we're back from our honeymoon fuckfest so that I can fuck you myself, and show you just how much of a perverted slut I am. I'm getting horny just thinking about it," she said as she squirmed in her seat. Suddenly she stood up, and for a second, I thought she was going to drag me upstairs to help her relieve herself. Instead, she just said, "I'll be right back," before running off to our bedroom.

Alexis and I stared at each other in confusion over Casey's sudden mood swing. When she returned, I was beyond horrified to see that she had a dildo in her hand. "Casey, what the fuck?" I asked but she ignored me.

Instead, she went to her mother, grabbed her hand and forced the dildo into Alexis' hand. "That is my favourite dildo; it's moulded from Derrik's beautiful cock." The shock on her mother's face was probably only matched by the humiliation in mine. "What I want, mother, is for you to take this pussy moistening piece of plastic home with you, get naked on your bed, and shove this thing up in your cunt as far as it'll go, as hard and as fast as you can, while you listen to that voicemail I left to tempt you with. I want you to imagine yourself saying the words I said, taking that ferocious fucking from behind with your face against the mattress and that sexy round ass of yours in the air. I don't want you to stop until you blackout from the pleasure. And when you recover, do it all over again, only this time, shove my fiancé's man-meat up that phat ass of yours until you're a drooling mess and you need to feel the real thing pounding your fuckholes into submission and you know that you'll do anything to make that happen.

"I want you to do this, every day until my wedding. I want you to email me fantasies you have so that Derrik and I can send you more voicemails to assist you in your daily masturbation into nirvana. I want you to be squirming in your seat at the rehearsal dinner, no panties on, as you sit as far as you can from your new obsession while still being at the same table and dying for him to touch you, to just look at you. I want you to be so horny that it'll take every bit of willpower you have to not just climb on top of him and impale yourself on the cock that has been haunting your dreams for months. I want to see you shaking with the effort to not just fall to your knees and beg him to stuff your slutty holes on the table in front of everyone as the most degenerate filth pours from your mouth.

"I want you to turn yourself into a drooling fucktoy for me and Derrik to tease relentlessly, anxiously awaiting the eve of our wedding so that your Master can claim his newest MILF slut. I want his cum to cover you when you come to us to get ready. Derrik's fucked all my other bridesmaids, and we love the taste of his cum; your arrival will be our snack break as we take turns licking fresh and dried cum off from all over your body. I want you to have a fresh load in your pussy and ass for me and Tammy to lick from you together; we'll tease you, but you won't be allowed to cum until after midnight, if we let you cum at all.

"Throughout our honeymoon, we'll call and make sure that you haven't cum yet, while we tease you as we fuck and suck all manner of hotties. We'll video chat as we dominate and fuck a MILF who looks like you, calling her Mommy, and humiliating you by saying that she fucks us better than you, and only letting her cum when you admit that she fucks us better than you ever could. But still, you won't be able to cum.

"You won't get to cum until we arrive home to see you cooking us a dinner where most of the ingredients have teased you by being shoved into your dripping pussy for a few strokes each, clad in nothing but a just too small apron and some thigh high silk stockings. As you serve us dinner, you'll clean the cum from our joining the Mile High club still on us from the flight home. But still, you will not cum. After dinner, you'll lead us upstairs to our bedroom as you tell us about how horny and wet you've been since we left. Before we enter our bedroom, you'll tell us that there's a surprise for us on the other side. Who she is, I'll leave to you; but she's to be a MILF, just like you.

"She's to be blindfolded, hands tied to the headboard and feet spread wide enough that she can't rub her legs together with two of my bigger vibrators in her pussy and ass. I want her in thigh highs whose colour compliments the one's you're wearing and your sexiest pair of panties that have been soaked with your juices as a gag. When you remove her gag, and she begs us to fuck her and make her cum, then and only then will I take this dildo that you've worshipped for the past few months, strap it into a harness and sandwich you between me and my husband as we double team you and make you cum so hard form being double penetrated that your screams will wake the neighbours and your tongue will describe how good it feels for your Master and Mistress to fuck you to the MILF still tied to the bed. You'll faint from the pleasure and awake to find that you've been switched out with the new MILF slut you've gifted us, a blissful smile on your lips as you realize that this is how things should be and where you belong.

"In short, mother, what I want is for you to become our Mommy-Slut and for us to take full advantage of that." Since she'd placed the dildo in her mother's hand, Casey had used her seductress voice as she described what had to be the hottest possible future for us to have over the next few months. For as embarrassed as I'd been by her shoving a replica of my dick into her mother's hand, I'd become a million times hornier with every word she'd uttered in that husky voice that demanded undivided attention and complete obedience. I'd seen her turn her boss into a drooling mess, begging Casey to let me fuck her, with just this voice; and I could see that it was having a similar effect here.

Reaching down, I was shocked to see my fiancée's hand slip under the dress her mother was wearing as she was unmistakably teasing Alexis' pussy. "You're dripping, Mommy," she staged whispered into her ear. "Does the thought of you becoming our Mommy-Slut really turn you on so much that you've soaked your panties through in the two minutes it took me to tell you how I'd turn you? Or did Derrik saying he'd love to have sex with you, all soft and romantic, make you this wet?" I was surprised when she kissed her mother sensually for a brief moment, until Alexis was returning the kiss, at which point Casey pulled away. With a slight growl, she demanded, "Answer me, Mommy! What has you so soaking wet?"

Whimpering and shaking from the continued torturous teasing from her daughter's hand in her panties, Alexis whispered something so quiet that I couldn't hear anything beyond her breathing. She flinched when Casey demanded that she repeat herself louder. "Your words! I want to be a slut for my daughter and her fiancé!" Alexis shouted in a horny whimper that I'd heard from her daughter more times than there were stars in the sky, and which had my already begging for release because it was so hard cock get even harder. "Noooo!" she whined as Casey pulled her hand out from her panties, shiny with her mother's juices.

Standing up, I caught Casey's hand before she started to lick it. I couldn't resist not having a taste, so I shook my head at her telling her no. "Look at my cock, Mommy-in-Law-Slut; do you see how hard you've made me simply by accepting your desires?"

"Yes, Master," she said in a voice that was slightly higher than her usual pitch.

She looked up to me with nothing but lust in her eyes, and it was one of the hardest things I've ever done to force myself not to take her right there. "Keep staring at that cock you want so much to be pounding you, Slut," I said in an effort to keep from the temptation to drench her in my cum. "When I stop talking, Mother-in-Law-Slut, you're going to get up and leave. You're going to do what your Daughter Mistress said: you're going to go home and fuck yourself into oblivion with my cock, while you listen to that voicemail we sent you. And when you wake up, you're going to do it all over again with my dildo cock in your ass.

"But I'm going to add to this assignment. First, I want you to set up a camera and record yourself as you go to town on your pussy and ass. Second, I want you to keep track of how many times you cum from fucking your pussy and ass, separately. For each time you orgasm with the dildo in your pussy, you're going to email us a fantasy that you have; you will go into explicit graphic detail for each one, describing everything from the start of the fantasy to your ultimate surrender to bliss. And for every analgasm you have, that is half the number of times I'm going to make you cum when I finally fuck you on the eve of my wedding. It's also how many loads you're going to be wearing when you join your daughter and her other bridesmaids to get ready the next day, as they lick it from your body as you give them a blow-by-blow account of how I fucked you the night before and that morning. Do you understand your tasks, my sexy Mother-in-Law-Slut?"

Still staring lovingly at my tenting cock, Alexis purred, "Yesssss, Master, I understand. Just a couple questions though, Master. Can I cum before I start to masturbate, Master; and if I do, does that count for my totals?"

"Hmmm, very intriguing," I said, wild ideas forming in my head. "Let's test your obedience and honour, shall we, my Pet? I'm going to say that you cannot cum until you're at home and have started to record yourself masturbating. If you fail to comply with the first set of orders that your Master gives you, then you're to start off your recording by saying so and declaring how many times you came. Should you cum in your pussy, you will write another fantasy for each time you cum while recording. Should you have an analgasm before you get home, the number of times I will make you cum will drop by one per unauthorized analgasm, but the number of my loads that you'll wear will increase by two. Is that understood, Slut Alexis?" I asked, hoping that she'd break my rules and cum at least once each before she got home.

"Yes, Master, I will obey," she said meekly, to which I nodded and sent her on her way.

"Oh, Mommy-Slut," Casey said in that seductive voice, causing her mother to turn back. "If you do disobey Master Derrik, those won't be the only punishments you face; I will be seeing to your punishment as well. Understood?"

Gulping audibly at the clear threat in her daughter's voice, Alexis nodded and said, "Yes, Mistress," before she walked out of the kitchen and left.

No sooner had the front door closed, than I was licking the drying juices from Casey's hand and moaning at the sweet tang of Alexis' cum, so very similar to her daughter's, with a hint towards Tammy's personal bouquet. "Ffffuuuccckkk, your mom tastes good!" I moaned between licks, as Casey tried to have me share. "Nu-uh," I said shaking my head and pulling her hand away. "After that little stunt that almost blew up in our faces, you don't get to enjoy its spoils until you swallow the three loads that are keeping me stiffer than a frozen statue of Ben Franklin seeing under Lady Liberty's toga for the first time. Now get sucking you perverted incest slut!"

Needless to say, we had a great afternoon. I'll go into details about Alexis' night later, as I want to get to how I told Terry about his duties as best man.

It was that Friday night and we were at our buddy Bill's for our bi-weekly get together. Bill's fairly loaded, so he has the biggest house to house us and our other buddies Gabe and Jack. Mostly these hangouts are just us watching sports and drinking for a few hours, maybe some poker or blackjack. Sometimes we head out for a round of golf in the summer. This particular Friday had been super hot, so we decided to drink and go for a swim in Bill's pool.

I waited a couple hours, letting the others get drunker than myself. Terry had to work in the morning so he was going slow too, which was perfect for me. I had just finished my Jack and ginger, and looked to see the others were nearly done their drinks as well. Getting off my floating chair and out of the pool, I asked, "Who needs a refill?" to which I got four hands in the air holding glasses. "Ter give me a hand, would ya?"

He got out and together we collected everyone's cups to bring inside. Once inside the kitchen, we started to get everything out for everyone's drinks. "You alright," Terry asked me. "This is only your fourth drink."

"So?"

"So, the others are on their seventh. Usually we keep pace with each other; I'm working tomorrow, but what's your excuse?" Teachers always know when something's bothering you. "It's not Cas, is it?"

"No, it's not Casey," I said with a chuckle. "Well, not directly anyway." Hearing this, Terry got a confused look on his face. "I've got something to tell/ask you. It's a little awkward but I promise it's a good thing."

Nodding, Terry said, "Ok. Shoot."

I adverted my gaze from him and started to make Gabe's margarita so I wouldn't have to see his face for the next few moments. "You know how I asked you to be my best man the other day?" He gave an affirmative grunt that he remembered. "Well, besides your traditional duties (bachelor party, rings, making sure I don't screw up majorly, etc.), me and Casey have agreed that there's another duty we want you to perform on the night before, after the rehearsal dinner."

"Ok; what sort of duty?"

Taking a silent breath, I turned back to look at him; knowing that he'd need to see the truth of it in my eyes. "A private one, one that you'll keep between the three of us until you die."

"Sounds serious. It's not illegal, is it?" he asked.

"No, it's not illegal and it's only dangerous if you're not safe." I'd finished the margarita and started on Bill's surprisingly good concoction of rum, root beer and chocolate milk that he called a Doodlez. Huffing overly dramatically, I locked eyes with Terry and said, "We want you to have sex with Casey on the night before our wedding."

There was a tense moment of silence before Terry burst out laughing. I wanted to both laugh with him and scold him for making a mockery of this, but knew that I could do neither. After a moment of his laughing and my just standing there, he calmed himself as he saw the gravity of this situation in my face. "You're serious? Holy fucking shit, you're serious!" he exclaimed as I just looked him in the eyes.

"Yes, I'm serious," I said, my tone and face denoting the truth of that. "I won't get into the full spiel about it, but it basically boils down to the fact that we're both perverts and we agreed to let each other sleep with the top member of the other's wedding party. I get her maid of honour; she gets my best man. We have our fun for the night and go on with our lives afterwards as though nothing happened. Bing, bang, boom!"

"You're joking right?" Terry said rhetorically. "You expect me to believe that you not only are ok with my sleeping with your fiancée, but also that you want me to do it the night before your wedding? And then expect me to just forget about it and never tell it to another person in my life? All because you and Casey are perverts?"

I could understand his incredulity; it'd been my idea and I still couldn't believe that I'd managed to convince Casey to go for this insane idea. "I know it sounds crazy, especially coming from me to you, but it's the truth. Casey has wanted to sleep with you for ages and has all but begged me to let you. And when she finally told me the truth about how you set us up, I couldn't say no. So, call it perversion, or us showing you our gratitude or life making a comedy from our tragic past, I don't care. We just want to know that you'll do it, and be discreet about it afterwards."