Carly's WMAF Fantasy Pt. 18

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Jay and Carly return to NYC. Carly evaluates Jay's prospects.
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Part 18 of the 32 part series

Updated 06/13/2023
Created 08/13/2018
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Thanks for the continued support from everyone. I'm (slowly) building towards the wedding but we've still got a little ways to go. Hopefully you enjoy learning about the new characters as Jay starts (finally) making progress with Louise.

*****

The three of us woke up in bed together. I'll never get tired of that. Waking up next to two gorgeous women who have a "grateful to be so well fucked" look. Or in this case a "Grateful to be permitted to cum after four hours of edging" look.

Kyrsten was already dressed, having woken up early to go work out. Carly was still laying on the bed exactly as she'd fallen asleep last night, a slight bit of drool coming out of her mouth that made me chuckle. As she woke up groggily, I kissed her and then kissed Kyrsten. "I've decided some things."

"Yes, Master?" Kyrsten asked, eagerness suffused her voice.

"Yes, Master?" Carly managed, still shaking cobwebs from her waking brain.

"I'm going to fuck every girl I want, from now on. And you two are going to help me."

"Of course, Master," Kyrsten said, smiling and showing me that she was fully onboard. The joy on her face gave me comfort that I was making the right decision.

"Carly, you're going to help me seduce all four of the sluts waiting back home for me. And you're not allowed to cum until I've had all four of them in all twelve of their holes." Carly's nod was accompanied by a shudder of arousal.

Kyrsten was also flush with her own horniness as I turned back to her, "Kyrsten, I know you can't have my cock every night... yet... so it'll be hard for you. You can cum as much as you want but only with Rebeccah. I want you to mold her into my plaything. Teach her to embrace being the dumb little bimbo that she obviously longs to be."

Kyrsten nodded, "Yes, Master. Thank you."

"And Carly... oh... Carly... you dumb little dissappointing slant eyed, yellow cunt," I told her. Her eyes fluttered open as she looked at me, "For cumming last night, you'll spend every night edging until I've had all four new sluts. You'll spend all day edging. And when I finally let you cum, it's going to be a month of ruined orgasms for you."

She gasped and, I swear to you, her whole body spasmed as if she came just from the thought. "Master," she said with a whine that conveyed the broad range of emotions she must be feeling at that moment. She was thrusting her hips into my leg harder and harder, grinding her bald pussy against me. "You won't be granted a real orgasm until we're married, slut," that did it for her. She shook again, a whole body shake that definitely looked like an orgasm. "Did you cum, slut?"

"I... I don't know what that was, Master. It... it wasn't an orgasm... but fuck... I could cum right now so easily. I want to... my whole body wants me to. But I won't let myself, Master. I promise. I'll be a good girl."

"I know," I told her and gave them both a kiss. We got packed and said our goodbyes. Not only did Kyrsten give me a mind melting kiss, but she laid one on Carly that was just as passionate and toe curling. We dropped her off back at her car and headed to the airport. In past trips, I'd always left Orlando to back to New York and felt like I was leaving something behind. And truthfully, watching Kyrsten wave as we drove off left me with that same melancholy. But the bigger part of me realized that with Carly next to me, I was never going to be "leaving home" again.

"Was all that too much?" I asked her.

"No, Master. Not at all?"

"So you're not resentful about your punishment? Or me fucking Jackie?"

"God no, Master," she said quickly.

I glanced at her and rubbed her thigh gently, "You don't like Jackie very much, do you?"

She was quiet for a moment before finally shaking her head. "No. I have a lot of mixed emotional baggage when it comes to her. She introduced me to this kink that I know is a huge part of me and part of me is actually kind of grateful for that. But she's a..." she trailed off and looked at me.

"A bitch?" I asked.

Carly laughed a little but didn't answer, instead asking, "How do you feel about her, Master?"

"She was a great lay. But... I don't know... something about her was a little off-putting. But seriously. Tell me what you think of her. I want to know?"

"I hate her, Master," Carly said quietly as she looked out the window.

"Oh, God. Carly, I'm so sorry... I never would have done it..." I started but she cut me off.

"That's not it, Jay. Watching you fuck someone I hate was... God... it was amazing. My whole body was on fire watching it. It's so fucked up but I kind of loved it. Watching you dominate that prissy, bitchy whore..." she said wistfully. Her eyes were closed as she enjoyed the wind on her face while she relived last night in her mind.

"Sometimes I think I understand you so well. And other times you still manage to surprise you with your depravity," I told her. She smiled back at me a bright, beaming smile.

"I hope I'm still surprising you with the depth of my perversions when we're 50, Master."

"Me too, my love. And I hope that I understand you even better than I do now. The more I learn, the more I love you."

"Thank you for not judging me, Master. I know I'm... unconventional," she said and I laughed. Unconventional was a pretty monumental understatement. She smirked at me then continued, "But you really do get me. And, Jay, I promise I would have told you if it was too much." She got really quiet for a second and cast her eyes down. She looked almost ashamed, "If anything, it wasn't enough actually."

"What do you mean?"

"I almost told you that I hated her so that you could... you know... torment me with it."

I grinned at her, "So if I'd talked about how much better she was. Or made you watch my white cock slide into her tight, white cunt up close?"

Carly simply nodded and I saw her fingers twitch with the desire to touch herself.

"You can edge yourself you dumb cunt," I told her and she instantly shoved her hand into her tight jeans and sighed with contentment. "Maybe I'll invite Jackie for a visit and just leave you tied to a chair all weekend?" she moaned. "Or maybe... if you're a really good girl for the next couple months... Maybe I'll invite her on our honeymoon and fuck her the whole time instead of you."

Carly's hips bucked up and she roared as she ripped her hand out of her pants. She was panting and shaking. "Fuck that was close. I nearly came from picturing that."

"Silly little slut," I told her. "Don't worry though, I don't actually like Jackie all that much."

"Part of me is kind of glad, Master. I'm not sure I could take a steady diet of her if I'm being totally honest."

"Me neither. I don't want to ever start actually thinking of you like that. As hot as it is in the moment, you're my wife..."

"First wife," she said with a smile.

I sighed, "First wife... maybe... but you're my wife and the mother of my child... okay... first child... whatever. The point is, I love you and I don't want you to ever have any actual doubt about it."

"Oh trust me. Listening to you talk to our parents told me I made the right decision. The way you stood up for me with my Dad. The way you talked about me and explained things to your parents. I know you love me, Master."

"Good... and you're really happy about getting married?"

"Oh my God. How can you ask that, Master?" she said with genuine incredulity. I glanced over at her and her beautiful, wind whipped, black hair was hiding her eyes but not the crooked smile underneath her long bangs.

"I just don't want you to feel pressured or rushed," I said. I reached over and tucked her hair back to see slightly watery eyes staring at me.

"Jay, if you want to land, go straight to the courthouse, and get married today, I'll do it."

"It's Sunday," I said simply.

She laughed, "Fine! We'll go abduct a judge and force them to do it then drive off Bonnie and Clyde style!"

"Bonnie and Clyde died!" I protested.

"Don't take the metaphor literally, Master. My point is, you asking me to marry you made me happier than anything that's happened to me in months other than maybe finding out I was pregnant."

I smiled. And I definitely didn't cry. Trying to shift the subject, I asked, "What are you looking for for the wedding? Do you want to just go get a judge to notarize it?"

"I want what you want, Master," she said woodenly. But this was one trap I knew about.

"Oh no. No way. Not on this one. You don't get to pawn this off on me completely. You have to tell me. I'll make whatever you want to have happen, but you gotta tell me. Besides, my Mom would kill me... like literally stab me in my sleep... if she found out I gave you the wedding I wanted and not the wedding you wanted."

She nodded and simply said, "Okay... well... for your Mom I'll try to be a little Bridezilla."

"Good girl. So... big or small?"

"Small... definitely small... maybe 30 or 40 people."

"Church?"

"We're buddhist. Is it important to you?"

I shook my head, "Not really... My mom converted do Judaism to marry my dad but then they both left to be lapsed Catholics."

"So non-denominational," she said and I nodded.

"Indoors or outdoors?"

"Indoors. I don't want to worry about the weather."

"Wedding party?" I asked.

"As big as it needs to be to fit all of your conquests."

I snickered. "Sherry as your maid of honor and Kyrsten as the 'Best Man'?"

She laughed a mirthful laugh. "I figured you'd want Roland to be the Best Man."

"I would, I think. But Kyrsten should figure prominently don't you think?"

"She could marry us," Carly said.

I tried to picture it and shook my head, "No. She could be your maid of honor."

"I think I'd like that. In fact... since so few people would be there... maybe... uhmm... Well..."

"What?"

"Maybe it could... you know... maybe it could like... really focus on our whole, you know, lifestyle?" My cock definitely stirred at that. Carly noticed and leaned over, slowly unzipping my pants and pulling out my cock. "If it's not too manipulative of me, Master. May I suck your cock while you tell me all the humiliating, degrading things you'd do to me at our wedding. And then we can decide, when we're not horny, which ones to incorporate?"

"You're always horny, slut," I said as I shoved her forcefully down onto my cock. "Let's see. What would I do to make you wet and feeling like the cheap set of holes you are. First, I'd have you collared with a special wedding collar that said 'Jay's Holes' on it," Carly sighed around my cock and sucked me harder. "You'd only be wearing that and a pair of white heels. So everyone attending would see you exposed. And they'd see all the horrible things I've written on you. Chink, whore, white cock fuck toy, cumdump... fuck that feels good, breeding bitch, rape meat."

She was sucking even harder now as she slid a hand down her shorts again, teasing herself while she blew me. "I'd make you utter completely submissive, degrading, humiliating vows. You'd have to explicitly pledge to help me fuck as many women as I want. To never demand my cock or my seed. To be grateful just to be permitted to know about my conquests. Fuck... you must like that you dumb cunt. Are you picturing everyone in our families seeing you like that? Knowing that they'll always see you for a pathetic, submissive cumdump?"

She obviously did like it based on her increasingly desperate moans. "And then instead of kissing me, you get to kiss your sister after she takes my cum in her mouth. That's your wedding kiss. My cum, from your sister, in front of our parents. And then you clip on a leash to your collar and hand it to me and crawl behind me as we head to the reception. And you know what we do at the reception?"

She pulled off my cock long enough to look up at me and ask, "What, Master?"

"You're tied up and have to watch as I fuck all my women. And then you take my cum out of whatever hole I decide to fill." She started sucking furiously and shoved herself down, engulfing my cock fully and milking me with her mouth while stroking me expertly with her tongue. It was easy to imagine that she really was bred and trained from birth to worship my cock. And that thought was enough to cause me to shoot into her mouth. She immediately came off my cock, not wanting me to black out while driving down the road. That just caused some to spurt up onto her face. She wiped me clean with her hand and licked her lips and fingers, looking for all the world like a cum worshipping slut. Which, of course, she was.

"MMM... Master, I want all of that. But definitely ask me again when we're less horny. I'm not thinking straight at all right now."

"Definitely... Though I'm less concerned with you and more concerned with my Mom and Dad's hearts," I said with a grin. She playfully punched my shoulder.

"Maybe we should have a more... private ceremony with only people who know us?" she said. "I trust you by the way. Feel free to surprise me with something." I thought about it. My mind was already spinning thinking about ways to make this special for Carly. I ended up thinking about it the whole flight back. I even made some notes on my phone while she was sleeping. By the time we landed, I already had plenty of ideas and plans. I also knew the next couple months was going to be very, very interesting. We got back and hopped into Carly's car and made our way back to my apartment. I'd reserved a spot in the parking garage of my building. It cost me an arm and a leg but it would be worth it at times. Besides, money wasn't going to be an issue for awhile. I threw Carly's bags over my shoulder and ushered her inside. I checked my mail and we ran into Maureen at the mailbox. Again.

"I'm starting to think you're stalking me," I said with a smile.

The petite redhead looked at me and winked, "I think you've got enough lady problems," she said before noticing Carly. "Oh... sorry. I mean..."

"It's okay," Carly said.

"Carly, this is my neighbor Maureen. Maureen, my fiance Carly," I introduced them. Carly's eyes got big as she recognized the name.

Maureen, on the other hand, silently appraised Carly, "So you've finally decided to settle down?" Her tone was flirty but also a little disappointed.

"God I hope not," Carly said reflexively. I chuckled at Maureen's stunned expression. "I mean... I just meant that I don't want him to feel like he's settling for me or slowing down or anything," she rambled and spoke rapidly, trying to get it all out.

I put my hand on Carly's shoulder and slid it down her spine. "Carly's the one who has really encouraged me. In fact, you've met her sister. The loud one, remember?"

Carly coughed a little and Maureen simply stared at us, trying to get a read on things. Carly's face was bright red with embarrassment and I was enjoying watching her shift from a nearly overwhelming combination of humiliation and arousal. "We'd love to have you over sometime. So that Carly and I can get to know you better. I've told Carly all about you and you're one of the people she'd been looking forward to meeting when she moves here. Isn't that right, babe?"

Carly paused for the briefest of moments before squeaking out a soft, "Yes sir."

Maureen looked surprised. She and I really hadn't spoken much over the past couple years. I knew she worked from home as a programmer and shared custody of her kids with her ex. I could imagine her and Carly getting into some real trouble when the opportunity arose. "Who, me?" she asked seeming genuinely confused.

"Yeah. You're both programmers and I just thought you might have a lot in common."

"Oh," she seemed almost disappointed and the mundanity of the request. "Sure," she said as she waved goodbye and shuffled out of the building. I signed some quick paperwork for Carly to get her own key and then we went upstairs.

"I love it when you do that," she said as she kissed my neck and stroked my cock the instant we were alone in the shiny metallic room. "When you make me call you 'sir' in front of random people. It makes me so hot."

"I know, baby," I told her and kissed her back. Her tongue danced in my mouth, making non-verbal promises that she had every intention of keeping. "You think you can seduce that one?"

"She's already ready to go, Master. I think she's a little bummed you didn't ask her up right now."

I made a noise, "Pff... whatever," I said.

"I'm not kidding, Master. She wanted you to invite her up right now so that we could 'get to know her'. She knows you're a player. She knows you're a nice guy. I think she sees you as a safe way to scratch her itch."

I kissed my fiance again and swept her up off her feet as the elevator door opened. She laughed and giggled, "What are you doing?"

"Carrying you across the threshold," I said as I staggered down the hall encumbered by my not inconsequential girlfriend, two bags and the key I was barely holding between my two knuckles. It was probably a bit of an ambitious attempt.

"That's AFTER we're married, Master," she said with a laugh.

"I know. But it felt like it would be fun," I said and kissed her as I fumbled with the door that I couldn't see. Finally, I gave up and set her down, "Hold on," I said. I opened the door and she jumped back into my arms as I carried her successfully into her new home. There were boxes everywhere and I knew we were going to have a ton of unpacking to do. It was so daunting that I wasn't sure we'd ever finish but I knew it had to get done.

We spent the rest of the night unpacking the essentials, reorganizing drawers and closet space and generally doing the mundane things that couples do when they move in together. I realized pretty quickly that this apartment, while nice for now, was going to be a tight fit for the two of us, let alone when a baby came along. That just solidified in my mind that it was time to look elsewhere. Maybe Carly was right. Her money would make it possible to just live somewhere simple and relaxing and focus on writing. It wouldn't be the glamorous Manhattan life but it might be even better. Certainly fewer prying eyes. I'd definitely need to give that some thought.

By the time we finished unpacking, we were almost too tired to have sex. Almost. I'm not sure if Maureen had come back and heard us or not but I'm pretty sure Carly was making every attempt to usurp the title of "Loud One" from her sister.

--

The next day, we went in to my work together. Carly was going to hang out in one of the cubicles near my office that had a Bloomberg terminal. She had some investments to take care of and apparently knew how to use one to research what she needed to. I didn't really ask or pry. It wasn't much my business despite what she might say. She was dressed casually for our office, a nice skirt and button down shirt with three inch heels. People would probably just assume she was a new intern or something.

But not my secretary. Victoria sees everything. "Who's the new girl, Mr. S?"

We'd talked about our cover story. It's not like we were trying to particularly hide anything but Carly really wanted to get a good look at her targets, Tabitha and Victoria. To size them up without them thinking of her as a threat or anything. "She's a friend of my brother that I set up for a couple days. Figured the spare terminal wasn't getting any use and that annual license is kind of cha-ching. If anyone needs it, just tell her. She knows she's only got it as a favor."

"Will do. She's pretty. Friend of Max's huh?"

I blinked a little, "Yeah. I mean... yeah... Why?"

Victoria smiled at me coyly, "No reason, Mr. S." She looked at me for a beat, trying to figure out if I was lying to her before finally saying, "You've got a meeting at 10am and 11:30. Want me to order lunch?"

"Yeah. Put it on my tab. I'll need you at the 11:30 so you'll need to skip lunch."