Carly's WMAF Fantasy Pt. 24

Please note: I don't normally provide "trigger warnings" or anything for my stories but there are some references within this story to events in a particular character's past that may bother some people. If references to noncon relationships bother you, you may want to skip the first half of this story or just come back for chapter 25. It's not dwelled on in any graphic way but it's an event in the past that drives a significant portion of the plot in the first half.

Second, thanks to all my beta readers. Especially UsuallyPresent who has been invaluable in getting this (and the next) chapter honed to the level they're at. Check out his stories if you get a chance. Any remaining errors on mine alone.

--

The next few weeks flew by in a blur. Not surprisingly, I had a steady stream of sex and it wasn't uncommon for me to be ploughing one or more of my girls while Carly sat in the living room planning things or making calls. I even got chastised once while she was on the phone with a venue because Maureen and Louise were making too much noise. You can't really blame Maureen though, the huge strap on that Louise was ramming into her ass would make anyone scream. I punished Louise later though. She really should have known better.

Unfortunately, as time progressed, there was more and more to do for the event. Even for the little wedding we had planned, there were a lot of things to take care of. Just coordinating guests became a full time job. While I loved having an endless string of women, I knew I'd have my whole life ahead of me for that and I let it taper off so I could take some of the burden off of Carly.

On top of all that, Victoria and I were planning one hell of a bachelor party blowout. Victoria was being absolutely amazing through all of this and I was really starting to warm to her as my "work wife".

One night I was talking to Kyrsten on Skype about the wedding logistics and I asked, "When are you going to be able to get up here, lover?"

"Roland, Jenn and I are flying up together on Tuesday before the bachelor party and we're staying the whole week."

"Oh that's awesome. We can hang out before everything gets crazy."

She looked at me. She already knew some of what I had planned. "I'm kind of looking forward to the crazy, Master."

"Me too. But I don't think Jenn is and I'd like to hangout with my best man some."

"I know. She'll be fine as long as you promise to keep him out of trouble."

"When's Rebeccah coming?" I asked.

"Eager to see my handiwork?" Kyrsten replied with a knowing grin.

"Am I that obvious?"

"Well, that hard cock in your hand doesn't tell lies," she said. It was true, seeing her spreading her cunt lips and fingering herself on camera for me had me rock hard. "She'll be up Wednesday morning. You're going to love her, Master. I think she's on the same flight as your brother, actually."

"I'm sure I will. And if I don't, I'll just take it out on your ass, babe," I smiled at her and she rolled her eyes, no doubt imagining being bent over and spanked until her ass was as red as her hair.

"I can't believe you don't have one of your local holes to take care of that thing for you, Master. When's the last time you had to stroke it yourself?"

"You mean other than when I finish and cum all over one of their faces?"

This time, Kyrsten did roll her eyes and I knew she imagined herself on the receiving end of a shower of my cum. "Yes, Master," she moaned.

I thought about the question. It really had been awhile. "It might be since the weekend you and Carly and I hooked up."

"Is it pathetic that I get turned on by that?"

"A little. But no more than I'd expect from a silly little slut like you."

The conversation became progressively dirtier and more detailed and soon she was cumming with a beautiful scream. Once we both had finished, we said our goodbyes, knowing that we only had a short time until we could be together again. Things with Kyrsten had been really difficult for both of us. Absence makes the heart grow fonder has a pretty big nugget of truth to it as we were discovering.

I was all nerves and jitters on Tuesday as I waited at the airport for my best friend, his girlfriend and one of the two loves of my life. I saw Roland and Jennifer first. Roland looked great in a perfectly tailored suit. Exactly how you'd imagine a high powered sports agent to look. Kind of like the Rock's younger brother in Ballers or something. Jennifer, however, stole the show. Her face shone through the airport like a lighthouse, attracting unabashed rubbernecking from random guys that noticed her. She was wearing a long, sleek dress that somehow showed every bit of her body but didn't seem particularly slutty. My eyes lingered a little longer on my best friend's girlfriend than they probably should have. Fortunately, from 50 feet away, you can't really tell. I hoped.

"Roland!" I shouted and waved. He came up and we gave each other a big hug as Jenn looked on with a knowing smile. I broke the hug and walked over to Jennifer who was positively beaming, "You keeping my boy happy?" I asked.

"Probably not nearly as happy as you but I'm doing my best," she said. We gave each other a hug, a less enthusiastic one than I'd gotten from Roland but any hug from Jennifer was bound to be at least a little exciting.

"Where's Kyrsten?" I asked looking down the corridor.

"She had the window seat in the last row. It's going to take her a bit," Roland said. "How about we get our luggage and we'll grab hers while we're down there. Meet you downstairs?"

"Sure," I said as I scanned the incoming crowd. Roland and Jenn walked off and I kept watching until finally I saw a shock of curly red hair bobbing through the crowd. I waved and up jumped Kyrsten's head with an outstretched arm waving back. I waited at the security line, tapping my foot as she made her way to me. It was completely worth the wait when I saw her. She came bounding towards me, barely giving me time to register the tight cutoff t-shirt and short running shorts she was wearing. She leapt at me and was kissing me within an instant, before I could even say "hello". The crowd of people brushed against us but we were both lost in our own little world. I kept holding her tightly as we kissed, unwilling to let go. It was like part of me was worried if I did, she'd leave me again.

When we finally stopped making out, I managed a soft, "I love you."

"I know," she purred back. "I love you too. And I've missed you. And I need you so fucking bad." She leaned in even closer, I could feel her breath on my ear as she whispered, "I used Rebeccah's tongue to edge myself every night since we skyped. I'm so ready to be broken again, Master."

As you can imagine, I had to adjust myself after that. I really didn't know how to respond so I simply smiled and held her hand. We walked downstairs and caught up with Jenn and Roland before heading out to the parking lot where Carly was waiting to pick us up.

"Why didn't you come in?" Jenn asked as Carly and she hugged in greeting.

Carly gave Roland a quick hug then moved over to Kyrsten, "I knew that Master and Kyrsten needed some time."

"You guys are so...," Jenn said but stopped in shock as Carly and Kyrsten greeted each other with a kiss every bit as fierce and passionate as the one that Kyrsten had given me only a few minutes earlier. "... weird," Jenn managed to finish before looking to Roland for some moral support. Roland simply shrugged and the five of us crammed into the car. Roland rode up front with Carly while Kyrsten, Jenn and I crammed into the back. "Now you two try not to hump like bunnies yet," the blonde beauty said. She was joking. Mostly.

Kyrsten and I managed to keep our hands to ourselves, barely, on the way home. All five of us were able to get caught up on everything and before long we were back in that familiar pattern of jokes and teasing that only a couple decades of interaction can bring. "You're going to love Louise," I told Kyrsten at one point.

Kyrsten looked at me, "Do you?"

"I... I don't know," I said.

"He does," Carly said from the front, flashing an innocent smile into the rearview mirror. "He's a completely smitten kitten."

Kyrsten and Jenn both giggled at that as I looked to Roland for help. Again, Roland shrugged, apparently he'd decided to avoid getting into the middle of anything regarding my lifestyle this week. Probably a good decision.

"We haven't said it to each other but she's very special."

"More special than my sister?" Carly asked.

"Or my sister?" Jenn added.

"Or your secretary?" Kyrsten piled on.

"Your secretary? Bro, company ink man. Not cool."

"He's double dipping there," Carly supplied helpfully. I felt like my head was on a swivel as my friends good naturedly piled on.

"Triple if you count that he's nailing his subordinate's wife too."

"Dude," Roland said and raised a fist to bump before seeing Jenn shoot him a gentle glare. "I mean, dude," he said in a more admonishing tone. His smile betrayed that, however.

"There's also my roommates, the messenger, my sister's OTHER...," Carly started listing.

"Enough," I said forcefully but without anger, "Yes, I'm currently sleeping with a lot of people. But they all know the deal and I have very strong feelings for a number of them."

"I know, Jay. We're just giving you a hard time," Jenn said, "It's not the lifestyle that Roland and I want but we get it. And we're really happy that it works for all of you. All... however many of you there are."

I smiled and wrapped my arm around Kyrsten, giving her a hug. She breathed out a sigh of relief and gave me a small smile and started to say something but Jenn interrupted her, "Okay, but seriously, what the fuck is going on with my sister?"

--

The car ride was a bit tense for awhile but ultimately the girls hashed everything out and got past it. Jenn was even less comfortable with her little sister getting involved in our "lifestyle" as she kept calling it but finally acknowledged what we all knew. Her sister was an adult and I wasn't going to hurt her. Those two things accepted as true, the rest of her objections mostly fell away. We got to their hotel which was three blocks from my condo building and helped Jenn and Roland get all unpacked. Carly and I had insisted Kyrsten stay with us. We'd been apart long enough. Kyrsten was in a hurry to get back to my place anyways. She was practically buzzing with need by the time we got the car unloaded. By the time we were walking into my building, she couldn't keep her hands off me.

"Great to see you back, Miss Kyrsten," the doorman said.

"You remember me?" she said, surprised and momentarily distracted from her growing need.

The doorman nodded, "Absolutely ma'am. Mr. Simpson has had a lot of girls through here but I remember you. Mr. Simpson was insistent that I look out for you."

Kyrsten smiled and looked at me with slightly misty eyes. "I love you," she said. 45 seconds later we were upstairs and 30 seconds after that we were collapsing onto the bed in a collection of giggles and laughter. My hands were all over Kyrsten and hers on me as Carly unpacked Kyrsten's clothes and otherwise acted as if she was oblivious to our carrying on. "God I've missed this cock," she said as she fished it out and rubbed it against her cheek before plunging it down her throat. "I've been practicing with some dildos, Master. I want you to be able to face fuck me as hard as you want," she said as she plunged her whole mouth straight down on my shaft without preamble. She massaged the head of my cock with her throat and it sent shivers down my spine. After fucking her mouth with my cock for a moment, she pulled off. Strands of drool stretched sexily from her lips to my dick and I twitched involuntarily. Then she said, "I want ALL my holes to be ready." She stood up and dropped her shorts before turning around and bending over. She had a cute little jeweled butt plug in. At least I thought it was cute and little. She pulled it out slowly and I realized it was fucking massive. When she pulled it all the way out, her ass gaped open before winking at me involuntarily.

"Fuck that's hot," I said as I stood up and shoved her forward against the wall. I grabbed the lube off our nightstand and dripped it on my cock, stroking once to spread it around before leaning into her and spearing her full.

"Oh my God, yes. Carly... Fuck... he's in my ass. He's fucking my ass and leaving my cunt empty."

Carly turned to us and smiled, her eyes twinkling with amusement, "Isn't that the best," she said. She came over and cupped Kyrsten's chin in her hand before giving her a little kiss on the cheek as I continued my assault. "To know he's using you in the way he wants. To know you're bringing him only the pleasure he needs?"

"Yessssss," she breathed out.

I jerked Kyrsten's hips backward and spun her so her face and tits were back on the bed. Then with one hand I grabbed Carly's hair and practically through her to the ground, "Get my girlfriend off, bitch."

"Yes, Master," Carly said with a smile as she crawled under Kyrsten and went to work.

"Oh thank you, Master. Thank you so much. Thank you. I love you. Fuck my ass. Cum in my ass. I need it. I need it. I love you," she said with an increasingly rambling voice. I started pounding into her harder and harder, taking what I wanted and, in turn, giving Kyrsten exactly what she needed.

"Oh fuck. I"m cumming. I'm cumming being fucked in the ass!" she squealed in excitement. Her ass clenched my cock like a vice and on the very next stroke, I started cumming too. I stayed inside her for a minute, enjoying each pulsing convulsion of her hot little ass.

I kissed the back of her neck and whispered into her ear, "I love you, too."

We all had gotten exactly what we needed. Even Carly, who more and more was existing to serve me, looked sublimely happy to finally have our little threesome back together. Our passions temporarily sated, we got cleaned up and flopped down in the bed together. Carly had stripped out of everything but the stockings she had been wearing and Kyrsten was walking around with only her little t-shirt on. I marveled, not for the first time, at the unbelievable luck that had fallen upon me since I'd started dating Carly.

"When do I get to see the famous Louise again, by the way?" Kyrsten said. As if in answer there was a soft knock at the door.

I smiled and kissed her, "How about right now," I said.

"What? Now?" Kyrsten said and Carly laughed as the gorgeous redhead pulled the sheets up over herself.

"Are you nervous?" I asked as I hopped out of bed and walked confidently to the door.

Kyrsten giggled. "A little. We barely met before. Now you talk about her all the time."

"You've got nothing to worry about Kyrsten. Carly's taught me I can love multiple people, each in different ways. Nobody will ever make me love you less."

"I... I know, Master. Thank you for saying it though." She looked so relieved that I was reminded of all of her ordeals when she was younger. Carly smiled, knowing some of it but, as far as I know, I was the only one that really knew what had happened between her and Jenn and Rebeccah's father.

I walked to the door, checking to make sure it was indeed Louise before I opened the door and surprised a random Fedex man or something. Louise was standing outside wearing a short, sexy little purple dress that plunged quite a ways down her chest. I opened the door and was greeted by a smile and then her lyrical, lilting laugh. "Already started, Mr. S?"

I answered her with a kiss and she jumped into my arms and wrapped her legs around my waist. I liked having a petite girlfriend that I could do that with and I effortlessly carried her into the bedroom while we continued to make out. Kyrsten and Carly gave a little clap and cheer as I brought the younger girl in and dropped her onto the bed. Kyrsten turned to Carly, "kind of a turn on watching him do that, isn't it?"

Carly smiled serenely, "It never gets old."

Louise looked over to the busty redhead and said, "Good to see you again, Kyrsten."

"You too," Kyrsten said with a smile, "I forgot how young and... fresh she is, Master. Though I guess she's not a 'good girl' anymore." Kyrsten smirked as she air quoted the words and Louise stuck her tongue out at the redhead playfully.

Carly said, "Don't misjudge her. Her little hand still packs quite the smack on your ass." All four of us laughed. Kyrsten knew full well what had transpired that first night between Carly, Louise and I.

Louise rolled over to Kyrsten as she disentangled herself from me. "Mr. S talks about you all the time, K. He really misses you. I think I speak for Carly when I say we're all looking forward to when we can be together for good."

I sat up and ran my fingers through my hair, "Now's as good a time as any to talk about this," I said. The three young ladies all sat up and looked at me attentively. Even Louise had a serious look on her face. They could tell by the tone in my voice that I had something important to say. "I'm just going to lay all this out with you guys and then we can figure out what to do. This lifestyle that Carly has led me into has changed a lot of my long term plans. It's unconventional and with the baby coming, it gets even more complicated. I love Carly. I love Kyrsten," I turned to Louise and said, "And at the risk of sounding cliche, I think I'm falling in love with you, Louise."

Louise blushed and gave me a slight nod and an almost imperceptible, "Me too," snuck out of her mouth.

"Carly and I had talked about moving somewhere warm and remote. Somewhere like the Keys where we didn't have to worry too much about prying eyes. But...," I looked at the girls again, silently appraising them. Carly knew what my concerns were, I knew she would be at peace with whatever decision I made. Louise and Kyrsten both had a little bit of tears in their eyes and I realized that they thought this might be some kind of breakup. I rushed the next words out quickly, "I'm not breaking up with you. The opposite in fact. I'm trying to figure out how we can all be together."

"What's wrong with moving to the Keys like you and Carly want?" Louise asked.

"I don't want you dropping out of school, baby. You're brilliant and you love it and I don't want to do that to you."

"I don't need the degree, Mr. S. I could study remotely... please... Master?" She looked desperate and my heart almost broke.

I shook my head, "No. It's important that you get an education. We could spend a couple years here in New York anyways."

Kyrsten looked up at me hopefully, "Master... may... may I make a suggestion?"

I laughed at her tentativeness. "Of course, my love."

Kyrsten shivered a little at the softness of that endearment, basking in emotions for a moment. "I've made the trip a bunch of times. Key Largo is only about an hour away from University of Miami."

Carly piped up, "Or we could even rent her an apartment in the city and she could be with us on the weekends, Master."

I looked between the girls. All three of them seemed so eager and ready for this drastic change. "Are you sure you'd all be happy with that? That's a lot of changes all at once."

Louise looked at the two older girls and nodded, "I only really have a couple of friends here, Mr. S. And one of them is Carly's sister who I figure is likely to visit at least some. I'm ready and I'm sure I'd be able to transfer just fine."

"Okay... it's settled then," I said clapping my hands together. "We'll start making the plans when Carly and I get back from our honeymoon."

"Where are you guys going?" Kyrsten asked.

I laughed, "We're going to the Keys to scout for houses." The girls gave a little cheer and Louise yanked me back down to her, kissing me passionately.