Carly's WMAF Fantasy Pt. 23

As always, thanks again for the support. Everyone from the people who vote and comment to the people who support me more broadly has been terrific. I hope you enjoy this chapter. Thanks especially to JB who's been volunteer editing the last few chapters. And without any further ado, enjoy the next chapter.

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Chapter 23

I woke up the next morning feeling absolutely full of vim and vigor. What was even more surprising is that Carly woke up feeling just as awake. Normally, I wasn't much of a morning person and Carly was even worse but after the night we had with Louise, we both woke up in such a good mood that you'd never know it.

I rolled over and kissed Carly, not minding the morning breath. "I love you, Carly Young."

"I love you too, Jay Simpson," she said earnestly. For once, neither of us felt the fire and passion. We felt something better. It was nice to just sit there and kiss Carly while holding her in my arms. "What's the plan, Master? We only have a few weeks left until the wedding."

"Do you need any help with the planning?"

"It's stressful but I can get through it. I want to do it. It helps me feel useful during the day. You do enough already and I don't want to bother you with it."

"Okay," I said, nodding in understanding. I gave her a kiss goodbye as I headed out to work.

I had quite the spring in my step as I walked in and it must have showed. Victoria immediately greeted me with a smile that shifted to a knowing grin as she looked at me, "Something good happen last night, boss?"

I nodded and returned her smile, "You could say that." I looked around before lowering my voice, "Carly and I fucked Louise last night."

Victoria's eyes sparkled as she licked her lips, "I'd love it if you told your work wife all about it."

I winked at her, "In time, my pet."

Victoria blushed deep red and sighed before changing the subject, "How are the wedding plans coming?"

Now it was my turn to sigh, "Good, I guess." I ran my fingers through my hair, "Carly wants to plan it all and not bother me with it all but I think it's getting to her."

Victoria was silent for a moment before looking up at me and meekly asking, "Would... would you like me to help?"

I studied her. She was sitting there trembling slightly as she looked up at me, unsure if she'd just overstepped. "I think that would be great... if it's not too weird for you that is."

"I told you, Mr. S, I'm totally fine with you having as many lovers as you want."

"It's one thing to know about them. It's another to be actively helping with the wedding plans of one."

Victoria stiffened her back up, sticking her prominent chest out in the process. "I told you, I want to be your help meet. At work and at home. Use me however you want. Not just sexually. If Carly is a little more... relaxed... in bed tonight because I helped ease her burden then that would make me very, very happy."

I looked at Victoria and thought about her. She was so different from the other women in my life. So similar to Carly and yet so wildly and completely different. After a long silence, I nodded, "Thank you. Call her after work, here's her number. Tell her I instructed you to call and offer her help," I said as I handed her the note. "Oh... and also. How well have you gotten to know Tabitha?"

Victoria frowned and I could tell she was weighing the delivery of bad news, "I haven't had much of a chance to make progress, Mr. S."

I nodded my head, expecting that answer, "It's fine. Ask her to join us after work for some drinks. Make it sound casual, okay?"

Victoria nodded with a smile. "Yes, Sir. Anything else, Sir?" she said in the same tone she had when taking down my lunch order. It was easy to see how 1950s business execs fell for their secretaries.

I smiled down at her, getting a glimpse down her shirt at the letters of the new tattoo she got the other day, "No, Victoria. That's all for now. Let me know when the job is done. I'll be in my office."

"Yes, Sir," she said and started back to work as if nothing had happened. Which, I suppose for her world view, maybe nothing had. By the end of the day, I'd organized a little impromptu team building exercise. Dave was bringing Madison and Hideo was being met by Sherry. Victoria was going to go help Carly after introducing me to Tabitha so everything was going according to plan.

When Victoria confirmed that Tabitha was coming, I found myself getting that familiar feeling of anticipation. Carly had transformed me into some kind of hunter, and I had new prey. It was a ridiculous emotion to run through me and part of my brain knew that. But I couldn't help getting excited at the anticipation.

There was a quiet little bar right near the office that we all met at after work. It wasn't uncommon for little after work get togethers and the bar staff always made sure to have a little table for us. I started a tab and bought everyone a round which earned a little cheer from the staff. Madison and Sherry showed up at the same time, which was actually kind of amusing. I'd completely forgotten that their one and only encounter was when I was fucking Madison and Sherry was serving as a literal cum dump for Madison's husband, Dave. Dave wasn't allowed to touch but he painted her with five loads while watching me fuck his wife.

The two beauties paused for a moment, sizing each other up. Madison had come straight from work and was dressed very professionally. Her tight, knee length skirt and expensive looking silk blouse contrasted starkly with Sherry who was wearing short little running shorts and a tight tank t-shirt that showed off her tiny waist and big tits. Hideo and Dave both got up and gave their respective significant others some welcome kisses. I then stood and kissed both women much more thoroughly, allowing my hands to wander up and down their asses. Sherry's kiss was familiar, warm and intimate. Madison's kiss was needful and teasing. I'd only fucked Madison once but that kiss told me she really wanted another round.

Tabitha arrived just as I was finishing the kiss with Madison. She did a little double take and whispered something to Victoria. I couldn't tell what was said but Tabitha gave me another look afterwards that was much more appraising.

Victoria brought Tabitha around and introduced everyone. I shook the Latina woman's hand. It was warm and strong and I noticed immediately that her hands were rougher than most women. She worked and she worked hard. She was dressed in her delivery outfit, a pair of tight bike shorts and a company polo-shirt. I could see the straps of a sports bra on. She could have passed for a fitness model with her sun-kissed well toned skin and obvious muscles. The fact that she still retained that feminine look despite the impressive physique was pretty remarkable. Her hair was a beautiful mix of colors and the mixture of golden blonde and chestnut brown shimmered in the dim light of the bar.

Hideo and Dave started talking and I realized that my little kiss had inadvertently outed their lifestyles to each other. I made a mental note to apologize to both of them, although neither seemed particularly bothered at the moment. With the two other girls talking and Victoria having already headed out, it gave me the perfect opportunity to get to know Tabitha.

"So how do you like being a runner?" I asked.

She looked at me and snickered before taking a sip of beer. "It's okay, I guess. It's the best of my jobs at the moment?"

"How many jobs do you have?"

"I do the runner thing full-time and then drive limos part time on the weekends," she said.

"Oh," I replied. I looked at her again, trying to figure her out.

"Plus I dance two nights a week and bartend once a week at a bikini bar."

"Which one?" I asked with a grin.

She sipped her beer again and smiled, "I'll let you try to figure that out."

I liked that she was being flirty with me. It seemed to bode well. "I know New York is expensive but that sounds rough."

She nodded, looking at me seriously, "It is. But you do what you gotta do. My sister had her kids sleep over and I've got to pay for them. They've been sleeping over for the past five years."

"Ouch." I wasn't sure what to do with that information. I felt bad for her but, judging by the way she talked about it, she wasn't upset.

As if to prove my thought right, Tabitha just shrugged and looked me dead in the eyes, 'Life can't be easy for everyone. Some of us have to work really hard, you know." It was a challenge, I could see the fire in her eyes.

I stiffened up a little, bristling at the implication that I didn't work hard. "Hard work comes in a lot of different forms."

She nodded and took another sip of her beer, "Sure. Some of us break our back and sweat all day for ten bucks an hour. Others sit in a nice air conditioned office for hours at a time and get paid ten times that."

"I'm not trying to suggest it's fair or right. Why don't you find something that pays better?"

She frowned a bit, "Because what I'd really like to do I don't have the money for."

Now it was my turn to be intrigued, "What's that?"

"I want to run a gym."

"You should get a job at the gym and work your way up. You're obviously not afraid of hard work," I said with a smile, grateful to have defused the conversation somewhat.

"They're all good ol' boy gyms in New York. Every wannabe Jersey Shore Joey and their vapid blonde bimbos," she said. She looked away and took a breath. "Sorry... You obviously work out and that wasn't fair."

I laughed a genuine laugh from my gut while Tabitha watched me, "Nobody's ever accused me of being a Jersey Shore guy."

"You fit the part," she said with a smile.

"Is that a compliment because I'm in good shape or a dig because I've got too much gel in my hair?"

"Couldn't it be mocking you for your spray tan?" she said with a smirk.

I did my best offended look, flailing my hands in dramatic fashion, "I'm offended. Offended! I've never spray tanned or even touched a tanning booth in my life, thank you very much."

"Uhhuh," she said as her eyes flicked over me. "So what's your deal? You obviously not European."

I wasn't sure I'd heard her right. "European?" I asked, confused.

"When I walked in you were kissing those two women. I asked Victoria if you were French or something and all she did was laugh. So why are you kissing the women of those two men? That one even has a ring," she said gesturing vaguely at Madison.

Madison and Dave were holding hands while they each talked to their respective conversation partners. They were that obvious "comfortable with each other" couple. It was nice to see. "Dave works for me and that's his wife. Hideo works for him and that's his girlfriend. She," I said, pointing at Sherry, "Is my fiancee's sister." I paused for dramatic effect, knowing that I hadn't answered her question, "And I'm sleeping with all of them."

Madison and Sherry heard me. They looked over at Tabitha and I before giggling and returning to their conspiratorial chatter. Tabitha studied me, "You're very open about it."

Now it was my turn to shrug, "I'm tired of hiding it. People are going to have to get used to this. I love my fiancee. And my girlfriend. And I sleep with a bunch of women. As long as everyone knows about it, what's the problem?"

"I can think of a dozen ways any one of you could get hurt," she said.

I looked at her. Her green eyes locked onto mine and I held her gaze for a long moment. "I can't promise that nobody will ever get hurt. I can promise that I won't ever intentionally hurt anyone I care about. It's not normal and we know it's not. But that doesn't mean it can't work for us."

Tabitha seemed to accept that and gave a slight nod, "At least your defense wasn't that you belonged to some wacko Mormon secessionist cult."

I allowed myself another grin, "Nope. In fact, this is all new to me. Carly, my fiancee, was the one that pushed me to this place. I'm just enough of a red blooded American male to see an opportunity and run with it."

"Well, I do like red blooded American males," she said.

"Just not Jersey Shore Joeys?"

She laughed a musical laugh and finished her beer with a deep chug. "Something like that."

The six of us talked for another hour. The only other time I got a little nervous was when the three girls went to the bathroom together. God only knows what they discussed in there. I apologized to Dave and Hideo who both quickly let me off the hook.

"Don't sweat it. I mean... don't do it in front of a partner or something... Although, hell... I bet Madison would love that," he said as he trailed off. He snapped back to reality and looked at me, "Yeah. It's fine man. Madison has been all over me for the last couple weeks and we're better than we ever have been. Hell, I was going to ask you if you wanted to have round two with her soon," he said with a laugh.

Hideo spoke up as well, "I'm not upset either, Sir. I was surprised at first but Dave and I have been talking and I think I understand things a little more. And maybe I'm a little more okay with how things are now."

"How's Sherry been the last few days?"

"Sir?" Hideo asked, shifting uncomfortably. He knew what I was asking.

"How has she been with all of her new tattoos and piercings and you making her cum non-stop?"

Hideo looked at me then at Dave before answering, "She's been very... domineering," he said.

"Bitchy?" I asked and Hideo nodded meekly. "And are you okay with that?"

Hideo looked at me then at Dave, "Yessir. She's still very nice and loving and... truthfully... I always liked girls with a little sass. It's why none of the girls my mother hooked me up with ever clicked for me. They were always so meek and proper. I much prefer Sherry."

I put my hands on his shoulder, "Good. Then we both get what we want from her, don't we?"

Hideo smiled and nodded eagerly. "Yessir. Oh, and the tattoos are super hot. Did you know I have a thing for tattooed women? It's so taboo in our culture... it's very hot."

"I didn't but I'm glad you like them."

The girls came back to the table and Madison and Sherry walked up to me with Tabitha behind them. Sherry spoke first, "Master, we'd like you to take us back to your place so we can continue the party."

"Really? Tabitha too?"

"It was Tabitha's idea... Master," Madison said, struggling through the word. I knew it wasn't her thing really so she was definitely working hard.

"Uhhuh. I think it's pretty clear what you both want," I said, looking at the two girls as they stood in front of me. "Tabitha, why do you want to go back to my place?"

"I'm intrigued. I want to see how it all works. How you manage to please so many women. Sherry told me it's a pretty big count."

"Truthfully, I usually enjoy my women in ones and twos. But what's life without a little challenge," I said as I stood. I settled the bill and we grabbed an Uber to my condo unit. I settled into the backseat and Sherry and Madison eagerly hopped in on either side of me. I put my arms around each of them and tried valiantly to continue the conversation with Tabitha while Madison and Sherry whispered dirty suggestions into my ears. More than once I had to close my eyes and force myself to concentrate on what the beautiful woman was saying.

"I can't stay long. I've got to get home to the kids. I can't exactly afford extra for a babysitter," she said.

"But we're gonna have such a fun time," Madison said though if I'm honest, it didn't particularly sound like she was upset to lose the competition.

"I'm sure my Master would chip in to cover the extra for the babysitter," Sherry said before realizing how that sounds, "I mean... I didn't mean..." she stammered in embarrassment.

Tabitha's eyes twinkled a little but she didn't look angry, "It's alright. I understand."

"You'll have to forgive Sherry, she gets a little bubble headed when she hasn't been fucked in awhile. How long has it been, slut?"

"Too long, Master. Far, far too long," she whispered into my ear making no attempt to keep her voice down.

"Do they all call you that?"

"What? Master? No... I let different girls call me different things. Some of them like rules. Some of them like freedom. I really do get off on watching them get off so I try very hard to give them what they crave."

Again, that mischievous twinkle in her eye flitted by and she evaluated me. I could see her skin slightly flush and her breathing was a little heavy. Her breasts swelled inside the shirt she was wearing, drawing my eye despite my best effort. She pursed her lips and said, "If you don't mind, I'd like to spend some time watching you guys and how you interact. I'm intrigued." She paused for a moment before continuing, "But I really can't afford it without a little help."

I smiled, "I don't mind at all," I said and fished out my wallet. I don't usually carry much cash but was fortunate to have a couple $20s to give her. She took them and smoothly tucked them into her bra.

"Don't think this means I'm for sale," she said with a lopsided grin.

I laughed, "I wouldn't dream of it. Just a friend helping another friend out."

She squirmed in her seat, watching as Sherry and Madison roamed their hands all over me. She made a quick call to her babysitter while we finished the short ride to my building. We all bundled out of the escalade and quickly walked inside. Once in the elevator, Sherry and Madison both started getting even friskier with Sherry trying to stick her tongue all the way down my throat while Madison continued to whisper dirty things in my ear and rub my cock.

When the doors opened, we saw Maureen, my hot redhead MILF neighbor who enjoys being objectified, coming down the hall. Unfortunately, she had her two kids with her. The three of us quickly disentangled our hands from each other to keep the prying eyes of her redheaded progeny from asking awkward questions.

"Thank you," Maureen said softly as we walked past.

"No problem," I said though I frankly wasn't certain if she was thanking me for the night we had together or the courtesy we just displayed. I assumed the latter but my cock was telling me it might be the former.

"Have fun at your party. We'll be out until late," she said, giving me some comfort that if things got loud, I wouldn't be bothering anyone.

"Thanks. We will," I said. The six of us bundled in through the door, laughing about the close call.

"I told you you're eagerness would get you in trouble some day, dear," Dave said to his loving, soon-to-be-cheating-again wife.

"Oh hush, David. It wasn't THAT close," she said as she kissed me again. "Now go make us some drinks while Jay shows me around."

I laughed. My apartment really wasn't that much. A single living room, small kitchen area, bedroom and bathroom. But I was pretty sure Madison was really saying, "Take me to the bedroom right now."

I opened the bedroom door, really not sure what I was expecting to see. What I did see wouldn't have made my top ten list of possibilities, however. Victoria and Carly had both put on one of my dress shirts each and were pounding on each other. With pillows. I stood there, mouth agape, as two of the sexiest women I knew had a legitimate adult pillow fight. The two of them were laughing uproariously as they flailed about, at one point Carly ducked a wild swing from my secretary and gripped her own pillow two handed to deliver a vicious looking uppercut. It actually took Victoria off her feet a little, knocking her onto her back on the bed with a thud.

Carly made a victorious fist pump and only when she leaned over to catch her breath did she notice Madison, Sherry and I standing in the doorway, watching the bizarre scene.

"Oh... hi, Master," she said with a breathless snicker.

"Hi, Mr. S," Victoria said, sitting up quickly on her knees, obviously unfazed by the blow Carly had just delivered. She had only buttoned a couple buttons and her cunt and cleavage were fully on display. She reflexively started to cover herself then realized the silliness of that and clenched her hands into little fists. "We were just taking a break from the wedding planning."