The Deal

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Ass

As I stood and watched her walking down the aisle towards me, I couldn’t help but think myself the luckiest guy alive. Here was the most beautiful woman in the world, looking more beautiful than I could ever remember her being, in a beautiful white dress and the most dazzling smile as she looked up to me awaiting her at the alter. My bride was the perfect woman. Sexy as fuck, sweet, more intelligent than I could ever be, a great cook and best of all: as much of a pervert as I was.

Maybe I need to explain that last point. Starting at the beginning, my name is Derrik and my perfection personified bride is Casey. We met in my third year of university when she was a freshman during Frosh Week. But lots of people meet their spouses at school, but the best part is where we met. Most freshmen, myself included, tend to attend the events that the university puts on for the first week, as well as the parties that the sororities and frats have to entice new pledges. But Casey, she’s apparently different from most girls I’d met to this point, as it’s move in day (for whatever crazy reason, this year it was the Tuesday before Labour Day), and she’s decided to forgo the parties and university events and at 3 in the afternoon, decided that the fanciest strip club is where she wanted to be.

There weren’t many people there, a couple seniors (65+) watching the lack-luster MILF that was going through the motions on stage, a few middle-aged guys getting drunk at the bar as they tried to hit on what was clearly their co-worker that was hating every second she had to be in such a place (Karen vibes, I tell you), and finally, myself. Casey made a grand entrance by throwing the double doors open wide and strutting in with a sway to her hips that would give the biggest teases a run for their money, all while being silhouetted by the blinding sunlight from outside. We all turned at this over-the-top entrance to see this fresh faced eighteen-year-old with vibrant red hair that hung in loose waves down past her shoulders, a pair of glasses with thick black frames, and an outfit that screamed how much of a naughty schoolgirl she was. Her white blouse was thin and covered by a plain sweater vest that couldn’t hide how big her boobs were; and her frilly skirt came to just above her knees, revealing her white stocking covered legs that reflected the blinding sunlight even more.

She scanned the room before striding purposefully towards me with that teasing walk of hers. Seeing her beeline to me, most everyone returned to what they were doing. Except me. I was captivated by this creature that was making her way towards me. With the doors now closed, I was able to see that she had a pair of heeled brown boots that reminded me of the type of boots you think of when picturing Robin Hood. When she finally reached me, she pushed away the table and straddled my lap. Leaning in, she kissed me hungrily, tongue and all. My mind and body were frozen by this random stranger coming onto me in such a brazen fashion that it took me half a minute before I started to kiss her back, causing her to moan sexily into my throat. When she released my mouth a minute later, she trailed her lips up my jaw to my ear.

Giving it a quick bite, she said the hottest thing ever whispered into my ear to that point in my life (she’s since topped it a couple dozen times in the intervening years). “Take me,” she breathed in a husky whisper. “Take me right now and I’ll be your slut forever. Pop the cherries on all of my fuckholes and make me the happiest slut in the world.”

I didn’t need to be told twice. Grabbing a hold of her ass (which felt fantastic), I stood up and started walking to the door. Casey wrapped her legs around me as I walked and by the time we got to the door, the drunk idiots at the bar were whooping our exit. When I got us to my car, I opened the backseat and tossed her inside. She looked up at me with hungry eyes, the glasses adding a hint of extra sexiness to this already stimulating sight before me. Still standing outside my car’s backseat, I unzipped my fly and dropped my pants and boxers to my knees, exposing my hard eight inches to her. She let out a gasp before licking her lips and grabbing hold of my dick.

“Mmmm,” she purred as she started to slowly stroke me. “I can’t wait to have this big cock stretching me out in all my holes as you use me for your pleasure,” she murmured, causing my cock to twitch. She leaned down and I felt her hot breath on my head. And then her lips were wrapped around the ridge on the bottom of my cockhead. She sucked like a straw while her tongue played with my slit for a few seconds before she pulled away. “Tammy’s going to be so jealous,” she whispered to herself before launching herself at me again.

I won’t go into details, but after blowing my load on her face, we went back to my place and I fucked her the rest of the afternoon until it was about 10. She hadn’t lied, she was a virgin, and apparently now my slut. And from that day forward, we were dating and I quickly fell in love. I took her nurdağı escort home for Thanksgiving and she introduced me to her mom on Christmas. That was also when I met Tammy, her cousin who was a year older than Casey and her best friend. That was also my first of many threesomes. Casey was insatiable in the bedroom, pretty much any kink you could think of she had. We bought a copy of the Karma Sutra and worked our way through it every other month. She came up with plans to seduce our professors (always being successful, and including some of my firsts with men, as well as older women). By the time she graduated, I’d had a ring burning a hole in my pocket for a year and a half.

Which is where this story really begins. Ever since I’d proposed and she’d said yes, an idea had begun to formulate in my head. I wanted to surprise her by coming up with the kinky idea, so I tried to think of the best way to spring it on her. So, one night after a rather mundane bout of sex, I said to her, “I have an idea for the wedding.”

“Lay it on me,” she said as she snuggled closer to me, ready to fall asleep.

“Well, it’s more for the night before the wedding.” This got her full attention, as she pushed herself up to look into my face. “What if we didn’t go home together that night?” This was a risk in asking, for as kinky and open as we’d always been, we’d always were together in it, and always came home together. This wasn’t really a trust issue thing with us, more a ‘we value what we have and should remind ourselves of that whenever we get into the kinky side of our relationship’.

“I’m listening,” Casey said as she looked down at me with her blue eyes, eyes that seemed to be weighing my soul at that moment.

Sitting myself up against the headboard, I started, “Every wedding we’ve been to the past couple years, you’ve always stated your love of the tradition of the groom not seeing the bride until she’s walking down the aisle. So, our going home together would put that in jeopardy.”

“Uh-huh,” she agreed, suspicion in her eyes.

“And since that night is technically our last night of freedom, and we’re both major sluts, I thought we could do something special.” Her gaze was unnerving, as she continued to judge me silently as I explained myself. “You haven’t asked anyone to be your maid of honour yet, have you?”

“Not yet; but we all know I’m going to ask Tammy,” she said, the fierce piercing of her gaze faltering slightly.

“Well, what if you didn’t?” I asked cautiously, causing Casey to look at me with both suspicion and reproach. Throwing my hands up, I said, “Hey, it’s nothing against Tammy; you know I love her. Hell, the three of us have fucked just about as much as the two of us have.” Her gaze narrowed and I could practically feel it tearing into me and making me get to my point in all this. “We’ve had fun seducing the maid of honour and best man at weddings in the past,” I started, as she nodded in agreement. “How hot do you think it would be, if we did it at our own?”

I knew I had intrigued Casey with this notion as her eyes widened. “You have my attention,” she said. “Go on.”

“What if we picked each other’s maid of honour and best man. We choose from a select list that we’ve unintentionally made over the years, and then after the rehearsal dinner, we go home with them and fuck them.”

“Interesting,” Casey said with a pause, and I could see the wheels turning in her head as she considered the idea. “What’s this list we’ve unintentionally made?” she asked.

“People we haven’t slept with,” I said. “For one reason or another, we’ve deemed them to be off limits, but that, at least for this one night, are fair game.”

Behind her consideration of the idea, I could see that Casey was starting to get turned on by it. Over the years we’d roleplayed as differing members of a bridal party and had some fun sex with it. And the sex we’d had while actually seducing a maid of honour and best man at a few weddings had been pretty hot too. I knew that she wasn’t immediately put off by all this, I just didn’t know how she’d react to it being private. “It wouldn’t be like we normally do things,” she said in an even voice that hid her true thoughts on the matter. “You want to not see each other from the time we leave after the rehearsal dinner to the time I’m walking down the aisle.”

She’d said it as a statement but I knew that it was really a question. So, I answered it as one, “Truthfully, I’d want to wake up to you riding me before I flipped us into a 69 and I could give you a facial to walk down the aisle with.” Seeing her look of hunger at the picture I had just painted, I was tempted to say let’s do that instead. But I decided to forge ahead with my original idea. “But as sexy as that idea is, I know that you have a soft spot in your heart for some of these traditions. And truthfully, so do I. So, I came up with a kinky idea to help us in such an endeavour.”

Casey swung her leg over me so that she was straddling my nurdağı escort bayan hips and groin. “While it’s true that half of the wetness leaking out of me is your yummy jizz, I hope you can feel how wet this whole idea is making me. I’ll probably need to talk to Tammy about not asking her to be my MOH, but once I explain, I’m sure she’ll understand.” It was at this point that she started to slowly stroke my cock back to hardness. “So, my hard D, since you’ve thought of this idea for presumably more than a day, do you have any idea who you’d want to be my maid of honour? Which one of my friend’s pussies do you want to stick this hard cock into and ravage the night away on the eve of our wedding? Who’s the lucky slut that gets my man on his last night of freedom?”

I was now fully hard and she was rubbing her dripping cunt against my head, teasing me to no end. “Say her name and I’ll ‘butt dial’ her right now while we roleplay your night together,” she whispered in my ear and causing me to buck my hips trying to find her hole. “I bet it’s Charlotte,” she said, indicating her very Christian roommate from college. “She’s always been such a bitch about how loud we were, but I bet she was jilling herself raw listening to us. Fuck, it be so hot for you to take her down a peg and turn her into a drooling cumslut for a night.”

That was indeed a very hot thot, but I shook my head. “We can do that together when we get back from our honeymoon,” I said with a shake of my head. “She’ll be so sexy in your nun costume and covered in our cum. But she isn’t who I was thinking of. And as much as I want you to drop that tight twat of yours down on my cock, you don’t get to have my dick until you guess who I had in mind.”

Casey gave a pout at this, and a brief whine escaped her lips. “Please Master, you’ve made me so horny,” she said in a sexy baby voice as she tried to push her hips down. And as much as I wanted to feel her warm tightness around me, I knew that it would be so much better for the both of us if I forced her to indulge in this game.

With a quick but hard smack to her pussy, which caused her to gasp in shocked pain as well as stop trying to impale herself on my erection, I said in a commanding tone, “No Slut. I told you, you need to earn the right to ride my dick. So keep guessing, and I’ll tell you if you’re getting warmer.” To keep her horny though, I brought my hand to her tits and began to play with her hard nipples.

“Oh, that’s not fair, Master D,” she whimpered as she tried to find another one of her friends we hadn’t slept with. “Oh, what about Shawna? I don’t know why we haven’t tried to fuck her phat black ass, but she loves it in the ass, so I know she’d be down.”

Pinching her nipples a little harder than was erotic, I said, “Colder.”

As I returned to normal tit play, she got a concentrated look on her pouting face. “Are questions allowed?” she asked.

“Depends,” I replied after a moment. “I’ll give vague answers, but won’t give specifics.” I gave her a quick rub up and down her lips with my cock to keep her on edge.

“OHH! Please Master, please put it in,” Casey whined in a sexy exhale. To get her back on track, I slid my hands down to her waist and pulled it further from my twitching cock. “No-no no no no! I’ll be good, I promise.” She mewled contently when my hands returned to her boobs and resumed the teasing of her nipples. “What’s the difference between Charlotte and Shawna; what makes Shawna colder than Charlotte?” she asked, thrusting her breasts further into my hands for more stimulation.

“Charlotte has something in common with this woman that Shawna doesn’t, something more than race.” Casey was silent for a long while as she thought. It was at least five minutes before either of us said another word, at which point I was starting to get slightly annoyed. “If you don’t make another guess within thirty seconds of me finishing threatening you, Slut, you’re going to spend the rest of the night with a spreader between your legs and your hands tied behind your back so that you can’t touch yourself until I decide to let you out in the morning.” I saw the fear in her eyes at not being allowed to cum and started to count to thirty in my head.

I was at 27 when she guessed in a panic, “Kara?” I shook my head and was about to pinch her nipple again, when she rushed out, “Vicki? Em? Claudia? Daph? Wendy?”

Still shaking my head, I gave her nipples a squeeze to slow her down. “You’re getting colder with every name! Stop guessing to just make a guess and think. This woman is close enough to you that everyone won’t be surprised if you make her your maid of honour. Think of the women closest to you, that aren’t Tammy, and who fits this description.”

Casey was silent for a moment and then I saw the answer pop into her head. “You really are a pervert, you know that right?” she asked me rhetorically as she reached to the bedside and grabbed her phone. Her face illuminated by the light of it as she scrolled escort nurdağı for something, Casey began to spin her hips in a circular motion as she rubbed herself on my hard cock. Turning the phone to me to show me a contact listed in her phone under a single name she said, “But I can’t say as I blame you. She’s a sexy MILF, even at 47, and the thought of fucking her is quite hot.”

Feeling my cock twitch as she said that, Casey got a sexy smirk at her not being the only one turned on right now. “Oh, Master D,” she said in a baby voice, “does the thought of seeing me and my mother in a 69 turn you on? Does the image of us kneeling before your cock as we worship it in tandem make you want to bust your load all over my horny pussy?” As she slid herself down my shaft, her voice returned to its normal, lust inspiring tone as she continued to fill my head with some of the sexiest images that had ever graced my mind’s eye. “Do you want to feel her milk-filled titties squeezing around your cock as I push them together around your dick, lubing you up with her Mommy milk as you fuck those perky tits, before you cum on them and get hard again as I lick your sweet jizz from my mother’s breasts, the thick cum and creamy milk mixing on my tongue tantalizingly, before I share it with her while rubbing her wet pussy to the most surreal orgasm of her life?”

“FFFFFFFFUUUUCCCCKKKK!” I moaned, barely keeping my balls from bursting. Holding Casey to me so that she didn’t move and cause me to nut, I said between huffing breaths, “I’m pretty sure that’s the kinkiest thing that you’ve ever said to me.”

Slowly, agonizingly slowly, she squeezed her pussy around my cock, causing me to whimper for release. “I know,” she said with the biggest cat that swallowed the canary grin on her face. “But since mom isn’t currently lactating right now, for that image to become reality, I guess you’re going to have to knock her up when you fuck her on the eve of our wedding.” Hearing those words, my cock tried to flex itself through her pussy to slap my belly button. Both of us moaned as we felt this.

“Pervert,” Casey said, her sexy smile still on her face. “Does the thought of covering my mother’s tits in your cum while they leak out the milk meant for your bastard child turn you on that much?” she asked. Unable to speak, I simply nodded as if I was a bobblehead. Giving a snicker at my response, Casey pulled herself off me before flopping onto her stomach and raising her delectable ass into the air. Wiggling her ass teasingly, Casey changed the pitch of her voice so that it was eerily similar to her mother’s and said, “Cum and fuck a baby into your mother-in-law, you perverted stud!”

Within a second and a half, I was balls deep in her and pounding away. Grunting like an animal, I gave her no rest as I was consumed by the need to do as she had said and fuck a baby into my ersatz mother-in-law. Casey was unable to make much more noise other than some moaning and groaning. Closing my eyes from the pleasure, I tried to stave off the release that had been boiling in my balls since Casey had figured it out.

“Do you pound my daughter’s pussy this hard?” Casey asked as her cunt squeezed my cock tightly, but did little to slow my domineering pace. “Or is she too frigid to let you fuck her into the mattress and take her to oblivion like you are me? I bet my pussy is tighter than Casey’s.”

Fuck, I love this woman, and I swear she’s kinkier than I am. This roleplay was definitely the hottest we’d ever done. Finding my tongue, I played along, “Fuck Alexis! You’re so mother-in-law fucking tight! I should never have waited this long to pound this tight twat!”

“YYYYEEESSSS call me all the nasty, dirty things that my prude daughter won’t let you! I’ll do anything, be anything for this cock! I’ll fuck you at the alter tomorrow in front of everyone and make my prude, worthless daughter lick up all the splooge you cover me with!”

“You’re really excited about the thought of humiliating your daughter huh Slut?” I taunted.

“I’m not just some random slut, I’m your Whore Mother-in-Law Slut! Willing to do anything for the honour of fucking my Master Son-in-Law! I’ll suck your cock clean after it’s been in my ass; hell, I’ll suck it clean after it’s been in your Mommy’s ass!” That caused me to falter in my relentless rhythm. “OH, do you want your Whore Mother-in-Law to seduce your own Mommy? Gift her to you for Christmas and have you fuck the both of us in a Mommy sandwich for Mother’s Day, making us both mommies again as you spew your hot, thick, creamy, incestuous loads inside us? Then you get to drink refreshing milkshakes from our MILFshakes all summer long?”

Nothing on Earth could have stopped me from blowing my load as she finished talking. With a mighty roar (where I think I was actually yelling ‘roar’), I came the most I think I’ve ever cum in my life. I think I counted about a dozen spurts before I started to dribble. My strength gone, I collapsed onto Casey, causing the both of us to lie flat on our stomachs as we panted to catch our breath. A bright light in my face caused me to see that Casey had her phone on, mid-call to her mother. “Oh, Shit!” she said, saying what was running through my mind, before she hung up and turned to face me with the most devious smile I think I’d ever seen on her face. “That was really hot,” she said.

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