Carly's WMAF Fantasy Pt. 25

This chapter is, in many ways, the climax of the story. There's one more chapter to come but I've been building towards this and it was a lot of fun to write. While there's still some good character moments, this one is largely about the sex so if you're looking for that kind of story, this is your reward for reading through 24 other chapters! Because there's a lot of characters happening here, I figured this would be the write time to give a character list so here goes:

Jay: the POV character

Carly: Jay's fiancee. A submissive Asian woman with a cuckquean and mild raceplay fetish

Kyrsten: Jay's voluptuous redheaded girlfriend and the second love of his life

Louise: The third major girl in Jay's life. A beautiful young college freshman who used to be a slutty virgin and now is just a devoted slut

Sherry: Carly's little sister and a submissive brat with an orgasm denial fetish. Hideo is her beard of a boyfriend

Victoria: Jay's secretary and self proclaimed work-wife. Has some pretty unconventional religious beliefs about husbands and wives

Madison: Jay's coworker's (Dave) hotwife

Daphne: Dave's subordinate and another work conquest of Jay

Alex: Half Asian, half Irish stripper and Carly's former roommate in Boston

Natalie: Half Asian, half black women's studies professor and former roommate of Carly. Doesn't really believe what she teaches.

Roland: Jay's best friend from high school

Jennifer / Jenn: Roland's beautiful blonde girlfriend and Jay's childhood crush. Rebeccah's older sister.

Rebeccah: Jenn's blonde little sister. Has a bimbofication fetish and talks with an appropriately valley girl accent.

Starla: The third roommate (along with Sherry and Louise). Has a noncon fetish.

Tabitha: Athletic, hispanic bike messenger that delivers to Jay's office (he really likes his office conquests apparently). Turned on by the idea of being paid for sex.

Maureen: Redheaded MILF neighbor of Jay. Likes to be treated like an object during sex.

So that's the list of major characters and their little kinks. Now that you're caught up to speed, let's get on with the party!

--

The day after our little sex romp was the day of the big bachelor party. Guests were beginning to arrive and Carly's nervousness was boiling over. I'd tried to reassure her but I was quickly learning that there's only so much a fiancee can do to reassure the one who's flipping out.

"Carly, take a deep breath. We're going to get through all of this," I told her for the eighth time that morning. Someone unfamiliar with our lifestyle might have found the scene comical but this was pretty much everyday for me. Carly was leaning over the counter, wearing a studded leather collar emblazoned with the word "SLUT" along with a lace garter belt and stockings and five inch heels. She was working on her wedding planner and making phone calls to, I think at that moment, a florist as I recall. Meanwhile, I was getting a blowjob.

My girlfriend, Kyrsten, was currently deep throating my cock, sucking harder and harder while looking up at me with the most submissive eyes imaginable. I went back and forth with my eyes, watching Carly's ass as it shifted back and forth subconsciously then watching Kyrsten's eyes as she looked at me pleasingly.

I felt hands stroke my chest from behind. My secretary, Victoria, who'd come over early, ostensibly to help Carly with wedding plans, was now pressing her big tits against my back. I could feel her rock hard nipples poking into my shoulder blade and I turned around to pull her head forward for a tender kiss while my other hand held Kyrsten down on my cock. I broke the kiss with Victoria and yanked Kyrsten off my cock before standing up and padding over to Carly. I put my hands on her shoulders and massaged them lightly, "It's going to be great, babe."

"I know, Master. I know. But I'm so worried. And I want to do it right and have everything be great but also honor us and not keep secrets but also not bother people and definitely not offend people and..." she said all without taking a breath.

"Shhh...," I told her and hugged her tight, "You're rambling like Rebeccah, babe." That broke the tension and we laughed. I stroked her back as I held her in my arms. "If it helps, I've got the bachelor party all planned."

"I'm glad, Master. But that doesn't really help me."

"Oh trust me, you're going to love it. You're kind of the center of attention."

"What? Master... You're not going to... you know... share me..."

"Of course not you silly slut. We established that fact last night pretty clearly didn't we? You're my fiancee, mother of my children and soon to be my wife. No other flesh and blood cock ever gets your holes." She looked relieved, "But you're going to love it, I promise."

--

I left the girls and headed to the Ritz to look at the penthouse suite I'd rented. I walked around the room and surveyed everything. It cost... well... it was fucking expensive. But I needed the space. There was going to be a lot going on tonight and it was important that it come off perfectly. I'd had to pay a lot of money for the room and even more for all the accoutrements but it was worth it. Tonight would be a party that everyone would remember.

I checked on the last few items and then made my way downstairs and grabbed a cab to the office. Saturday work wasn't unusual and many of the party attendees were working. I checked my watch, noting that the pre-planned time was fast approaching. I'd already coordinated with the partners to make sure that the Saturday work didn't extend too far. Since it meant a little less overtime paid, they were okay with it.

When I got to my office, Victoria was sitting at her desk, smiling up at me, "Ready for your big night, Mr. S?" Even though I'd seen her just an hour or so before, her appearance still made me pause for a moment just to enjoy the view. She'd been slowly dressing more and more sexy at work and her current outfit was absolutely stunning. It accented all of her features while still staying well within the bounds of office modesty. The natural reaction was to say that she was dressing too sexy but you couldn't really pinpoint anything to complain about.

"I am. Everything looks great at the hotel. Thanks for your help," I said. I quickly glanced around and made sure nobody was around before reaching down with a finger and pulling her shirt to the side so I could see her well presented breasts resting atop her shelf bra. Nestled in between those massive mounds was the little gold crucifix that she always wore. She was very religious. A fact you'd never guess if you saw the way she begged to be fucked.

"Anything for you, Mr. S," she said, teasingly emphasizing the "anything".

"You know what you're supposed to do tonight?"

"Of course, Mr. S."

"Natalie will be there around 5 to help you. Everyone else has already been informed of their arrival times and you've got all their contact info in case anyone is late."

"Yes, Mr. S. I promise that you and the future Mrs. Simpson will have a perfect evening and an unforgettable bachelor party, Sir."

Victoria was the only person that really knew the full extent of what I had planned tonight. She'd helped me orchestrate the upcoming madness and kept me sane while I was doing it. While not as complicated as planning a wedding, this particular bachelor party required a level of stealth that wedding planning rarely needed. The fact that she'd done all that while also helping Carly plan the big event showed how wonderful she truly was. "Thanks, Victoria. If all goes according to plan, you won't be able to forget tonight either."

"You figured out my secret motivation for making it a good night, Mr. S," she said with a warm, flirty smile. She must be really turned on because that wasn't very like her. I returned the grin and went into my office to tie up some loose ends at work so that next week I could just relax.

Right at 5:15, Tabitha came in exactly as expected. As we planned, the general staff was long gone and the only people left on our floor were people coming to the party. Which was good because Tabitha's appearance was spectacular. She was wearing a tight fitting suit jacket and ultra short mini-skirt along with a little cap. The only other item was the bright yellow, leather collar wrapped around her neck. She looked like a chauffeur in a porno. Which is, exactly what she was going to be tonight. "Your ride is downstairs, Sir," she said formally. Her smile and knowing twinkle in her eye told me she was pretty eager for tonight.

"Did you pick up the other guests?"

"Yessir, they're all loaded up and ready."

"Excellent. Alright folks, who's ready for a helluva party?" I asked to cheers all around. It wasn't a large group, Victoria had already left to go get things ready. Daphne was the only woman from the company coming, along with Hideo and Dave. I'd invited all three partners out of courtesy but I'd made it pretty clear what was going to happen so Ms. Blake had tactfully declined. Mr. Wade and Mr. Ryan, however were quite happy to participate. Four other guys were also coming. Derrick and Tony were two of our best salesmen. When I'd first met them, I thought they were stereotypical frat guys from the Ivies. Both of them would mention their alma mater (Princeton and Dartmouth) reliably less than a minute into meeting a new person. And the way they talked about the secretaries and (female) junior analysts was pretty... locker room let's say. But once I got to know them, I realized they were actually pretty good guys. Just a little dickish at times.

The other two guys were Tyrone, a geeky young black guy from IT and Herman, a hispanic kid who just finished his internship. Normally, I wouldn't have invited someone so junior but he was remarkably mature for his age and he'd just smacked around everyone in the March Madness bracket that I run. This seemed like a good reward.

The ten of us went downstairs. At this point, only Dave and Hideo really knew anything about my lifestyle so Daphne kept a little apart from me though I could see her hands twitching with arousal. "So, Daphne isn't it?" asked Mr. Wade in the elevator.

"Yes, Sir," she said nervously.

"Bit unusual for a young lady to come to a bachelor party, isn't it?"

"Well... uhmm... Jay... err... Mr. Simpson invited me and I didn't want to refuse."

"Simpson, you didn't demand your subordinate come to this did you?" he snapped.

"No sir... This was her choice," I told him.

"Good... good... Well Daphne, I'll be watching you tonight. If you are uncomfortable, you just let me know," he said. I wasn't really sure if it was white knighting, flirting or just an older man trying, albeit awkwardly, to comfort a young woman.

"Don't worry sir, a couple other... young ladies... are also attending."

"Well, Mr. Simpson. I'm already intrigued by this little soiree you're throwing," Mr. Ryan said and the two partners nodded at each other.

We followed Tabitha out to the curb. Every eye was fixated on ass as she swayed sexily back and forth. Even Daphne looked entranced. When we arrived outside, the party bus was waiting. It was a large purple bus with blackout tinted windows. I'd rented a it for the night, knowing that some people were going to get completely plastered. I figured it would definitely be necessary. The idea had actually come together when I found out Tabitha's courier company also did limo and party bus rentals and Tabitha helped out on the weekends. The door opened and Roland was there, fist outstretched in greeting. We bumped and he grabbed my arm.

"Brother... this is awesome. We are gonna have fu-un tonight, my man!" he pulled me up the stairs and my eyes started to adjust to the dim interior. My little brother, Max, was there along with Jenn, Roland's girlfriend. Maureen, my neighbor whom I'd started fucking a couple weeks ago, was also there, flirting with Max, and so was Jackie, Carly's college roommate and former mistress. They all greeted me warmly, and I took a spot between Maureen and Jackie. Maureen instantly detached from my brother and leaned into me while I put an arm around each girl possessively and gave them both a long, tender kiss.

"Damn, player," Tony said with a whistle.

"You got some stones, my man," Derrick said and extended his hand for a friendly fist bump.

"Guys, this is Maureen, my neighbor and this is Jackie, Carly's college roommate and former lover."

Mr. Wade's eyes twinkled mischievously as he appraised me. Mr. Ryan simply sputtered, "I'm a little confused, Simpson..."

"You could say that Carly and I have a... semi-open relationship. I can date whomever I want and she can't."

I put my hand meaningfully high up on the thighs of both girls as I watched the two partners exchange a glance. Clearly they didn't know what to make of all of this.

"All the girls you meet tonight are my lovers," I said simply.

"Hey... almost all the girls," Roland interjected, putting his own arm around Jenn possessively. She leaned away from him slightly and gave him a meaningful look, "Well sure... fine... once... but it's not like you're 'lovers'," he said making half-hearted air quotes.

She grinned back at him and gave him a kiss, "That's all in the past, lover. You're the only one for me." Her voice was sweet and tender and Roland melted.

"You two used to date?" asked Herman, somewhat skeptically, I thought.

"Oh no," Jenn said and Herman looked surprised for a moment, "He just fucked me good last night is all."

Roland scowled but then let it pass over. He knew why it happened and I hoped he'd gotten past it. He'd traded Jenn to me for a chance at two of my other lovers. One of whom was Jenn's little sister, Rebeccah. So he didn't really have any room to complain. I leaned over to Herman and whispered, "My life is weird and wonderful, man. Don't try to figure it out. Just go with it tonight."

Herman nodded, still trying to process how someone like me could have landed all these girls. Plus others. Maureen caught his eye and held her hands up, separated by nearly a foot and a half as if to indicate a mammoth size. Herman's eyes bugged out and Tyrone choked on his drink, spluttering. "Stop," I said to Maureen and she and the other girls started laughing. Daphne as well which didn't go unnoticed by the partners.

"Her too?" Mr. Ryan added, pointing to my blonde co-worker.

I simply nodded.

"Very interesting young man working for us," he said.

"Hey... I'm a partner, now. Working WITH you," I said with a wink.

"Fair enough. Working with us," the man said and went back to sipping his drink.

Tabitha started the car and we all chatted, getting to know each other. Daphne was a little put out with Maureen and Jackie seated next to me but that quickly stopped being a problem when I pulled her onto my lap.

"So here's the rules for tonight, folks. Follow my rules, everyone will have an amazing time. If you want to get laid tonight, it'll definitely happen," I said and the group cheered. "All you have to do is pay attention to the system. Red collar means they're off limits to anyone they're not dating. Yellow collar means you're free to touch and kiss them but you have to ask for anything beyond that. Green means anything goes."

There was a chorus of nods and affirmatives. Maureen, Jackie and Daphne all pulled out yellow collars and put them around their necks seductively. Jenn's was red which Roland smiled at as he helped her clip hers into place.

Again, nods and acceptances from everyone which I fully expected. "Has everyone got their forms?"

I'd organized a group discount for STD tests from a doctor near the office. Everyone had a clean bill of health as of Wednesday when they took the tests so everything looked good. "I'll let you know the rest of the rules as we go. But don't worry... You're gonna have all the fun you can handle tonight."

The group started to loosen up after that as the booze began to flow. Maureen went back to flirting with Max and Jackie started talking to Derrick and Tony. Daphne and I went and talked to the partners, while I'd said the girls were free to do what they wanted, and I truly meant that with Maureen and Jackie, I really didn't like the idea of anyone fucking Daphne. I kept my hand on her back or her thigh, making my intentions clear.

"So this... uhmm... lifestyle of yours," Mr. Ryan started.

"It's called polyamory, Sir. And specifically my fiancee is what's called a cuckquean... sort of the opposite of cuckold," I said as I looked over at Dave and caught his eye. He'd heard me say that word but not the rest and I'm sure he wondered if he was being outed already.

The senior partner's eyes widened, "And she's just... okay with it?"

"All of my girlfriends are okay with it. You'll be able to meet them later, Sir."

"You're definitely an intriguing young man," Mr. Wade said admiringly.

"Thank you, Sir. I think. I do want to assure you both that this in no way affects my work performance. In fact, would it be fair to say you knew none of this was happening?"

They nodded and I continued, "I'm very discreet and I wouldn't want to bring anything bad onto the company."

"We understand, appreciate and agree with you, son." Mr. Wade said. I really liked the man. He'd been my mentor since I arrived and really helped me grow at the company, giving me lots of opportunities and shielding me from internal politics when I was younger.

"What about you two? How much are you going to partake tonight? I don't drink so I'm happy to be designated watchdog if either of you needs me to be."

"I'd appreciate that Simpson... or maybe I should get used to calling you Jay. But yes, my wife is fine with me going to these so long as I don't, and I quote, 'stick my dick in some young thing' end quote."

"No problem, Sir. I'll make sure your dick stays dry," I told him and we laughed.

Mr. Wade shook his head, "I'm good. My wife is okay with my... dalliances. Just as I'm okay with hers. I guess we have a more reciprocal open relationship." He smiled at me and I returned it.

"You're going to feel so good after tonight you're going to feel guilty for not calling her and inviting her," I joked. All four of us laughed at that and I gave Daphne a light kiss before leaving the three of them to talk while I went back to Roland. Jenn was sitting between Tyrone and Roland talking and laughing with both of them.

"What are you guys up to?" I asked.

"Dude... you've really brought out the tiger in Jenn. I'll give you that." His voice was a low whisper. It didn't sound like he was upset and for that, I was very grateful.

"Why... what's up?"

"She wants to have a threeway with my boy Tyrone here. She can't stop talking about being the cream in the middle of an Oreo."

I laughed, "And you're cool with that? I mean... we're cool, right?"

"Look, brother. I was pissed. I ain't gonna lie. But I always wanted her to get a little freaky and she's been in steady 'good girlfriend' mode since you nailed her. So who am I to complain."

"Good to hear it, man. I never wanted to come between you guys."

"Yeah, right. You'd add her to your little harem in a heartbeat if you could."

I laughed, "Well... maybe if things were different. But not while she's dating you. I promise man."

We gave each other a hug and I truly knew things were cool between us. When we turned our attention back to Jenn, she was breaking away from a kiss with Tyrone and looked like she'd got caught with her fingers in the cookie jar. "You okay with this, baby?"

Roland nodded and she gave him a quick peck before leaning back to kiss Tyrone some more. I watched as the party unfolded. The guys were excited but nervous but none more so than my little brother Max. We hadn't gotten a chance to talk much and I wasn't really sure what he thought of all of this. Max had been a quiet kid, following a lot in my foot steps without breaking out of that mold like I eventually did. I wasn't really sure how he was taking this dramatic change of lifestyle. I didn't really want it to somehow taint his vision of me. I took advantage of a quiet moment to extricate myself from Daphne and move over next to him.