California Dreamin' Pt. 06

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Jack’s Halloween costume turns into something more.
17.5k words
4.95
6.6k
11

Part 6 of the 8 part series

Updated 02/29/2024
Created 12/27/2023
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All characters are over the age of 18.

Our adorable threesome has finally reached the promised land, a healthy, amazing relationship with few boundaries and lots of opportunity for anything they could imagine. What could possibly introduce our college crushes to anything new and arousing? Jack loses a good-natured bet and is forced to find out, learning even more about himself in the process.

This and future chapters will deal with the messy (and hot!) reality of a three-way polyamorous relationship between two cis and one genderfluid person, who all realize that their place on the sexual spectrum changes to follow their hearts, and... other organs. If this kind of relationship, light drug use, cross dressing, or group sex offend or trigger you, please look elsewhere.

Dear reader - I have a decent imagination, but if there is a specific coupling or situation that would get you all hot and bothered in a good way, please let me know in the comments or in private feedback. Assuming I can write it authentically, I'd love to do something nice for you, having come along with me, Jack, Sloane, and Quinn this far.

Favorite and follow to make sure you get notified of each new chapter, in case it isn't in a category you watch.

Let me know in the comments how you're liking the story, and if you're keen on seeing it continue.

* * *

Sloan and I walked home from class that afternoon, still in a rather good mood from our morning menage 'a trois. About halfway back, our phones went off with a text from Quinn. She had good news to share.

"So what's this good news?" I asked as we stepped inside, she'd been hovering at the bottom of the stairs.

"I got a job!" she grinned widely.

We pulled her into a three-way hug.

"Congrats, proud of you!" I said.

"So where is it?" Sloane asked. "Somewhere we've heard of?"

"Oh yeah," said Quinn. "Starbucks, the one just down the street."

"That's cool," I said, trying to sound happy for her. It sounds awful to me. Her eyes sparkled anyway, and I was truly happy that it excited her.

"I get free drinks, and for probably you guys too if I'm working, but mostly... I get to wear whatever I want. As long as there's a green apron over it."

"Oh sweetie," said Sloane, hugging her again, "that's great. We're super happy for you."

"And after a few paychecks, I can start paying some rent."

"That reminds me," I cut in, "I never even paid for last month."

"Oh my gosh, you two..." said Sloane, shaking her head. "You're not paying me rent. We're together. This is our house. Besides, you guys do all the cooking. And it's not like it's my money anyway."

"Are you sure? I don't want to take advantage of you— er, your parents' generosity."

"They're more than happy to," said Sloane with a smile, "and I hope you take advantage of me at every opportunity."

"Naturally," I said. "I'm pretty sure have amazing sex with gorgeous landlord was in the lease agreement."

She stuck her tongue out at me while Quinn giggled.

"Come with me ladies, I think this feels like a beer on the roof kind of afternoon..."

* * *

I think I had finally become used to our new normal. Being with either of them individually was wonderful, and as three was perfect. Wether it was doing homework, washing dishes or cooking, or even folding laundry on the couch while something stupid played on the TV... everything was simply better.

Whenever we went out somewhere together, I was happy to hold their hands or share in whatever public displays of affection they felt up to. Every now and then we'd get a eyebrow raise from someone walking by or the person waiting on us in a restaurant, but I quickly got over being embarrassed. I knew my newfound confidence was at least partially due to being in the heart of the left coast and around a bunch of people I didn't know, but... baby steps, right?

I talked to my mom on the phone one evening and had the words on the tip of my tongue, but simply couldn't spit out that I was in a relationship. She'd squeal and grill me for details that I could never imagine giving to my mom, and that I'm sure she didn't want to hear anyway. If this was something that was going to last, and god I hoped it was... I'd have to figure out just the right words for that conversation.

Quinn had really leaned in to her job as a barista and came home from work bubbly and happy, eager to tell us stories and share what new drinks she'd learned to make that day. Even waking up in the small hours of the morning to walk to the shop, she did without complaining. She'd usually poke her head in my door on her way out, whispering a quiet are you awake? I almost always heard her and was rewarded with a tender kiss as I lay in my bed.

Sloane and I got in the habit of going for coffee at her shop on mornings we didn't have an early class. We'd sit at one of the tiny tables and just watch her, flitting around behind the counter and helping customers with her permanent but genuine smile.

It was fascinating and a bit arousing to see all manner of people that flirted with her as she took orders. Guys, girls, people in their teens to fifties. We quickly noticed that the flirting was definitely happening both directions. I'm sure it helped tips, but I knew she'd have done it anyway. Like my recent change in outlook on life, she finally felt comfortable in her own skin.

Oddly, I acclimated to being in a polyamorous relationship faster than I got used to the California weather. Seventies and eighties were still common in the afternoon, and I soaked it up every chance I could. I quickly took to doing my homework on the rooftop balcony. I'd take my laptop up and sit in the couch nearest the glass railing. Admittedly, having the ocean as a backdrop behind my screen probably made my work take longer, but that was a small price to pay for the view.

One such afternoon I was up there working on a paper and heard noises from the balcony below me. I guessed that Sloane's bedroom slider door was open, and she and Quinn were obviously inside talking. I couldn't make out words, nor did I care to eavesdrop, but the conversation eventually gave way to noises I most certainly did recognize.

My computer soon grew difficult to hold on my lap as my cock began to swell. I finally just set it beside me and palmed my growing erection through my shorts. Only being able to hear them was differently erotic than being able to see the a action, and I felt a bit naughty invading their private time. I could go join in, I thought, but quickly dismissed the idea. They're allowed to be alone too...

I heard both their voices clearly as they got louder, before impending climaxes began to change the tone. Quinn's slightly lower voice was last, obviously enthused about what was taking place. Hang on, both voices at the same time? My mind tried to envision what was happening. Doesn't somebody's mouth need to be... occupied?

I sat and let my cock soften before going back to my homework. Fifteen minutes later, I heard the door to the roof open behind me. Sloan emerged, wearing a short sundress and her blonde hair in a ponytail.

"I wondered if you were up here." She grinned and glanced at the ground. "It was a little warm in my room... I left the door open."

"I heard," I smirked. "Sounds like you guys had a nice time."

"We did." She sat down next to me and kissed my cheek. "Quinn has closing shift today and wanted a little goodbye."

"Hey, no judgement at all. That's part of us, right?"

"Yes, it is. Jack, I'm so proud of you with all this. It still takes me a minute every now and then to get my brain around... everything."

I chuckled. "I'm glad its not just me. Speaking of wrapping brains around things, can I ask you a question about... earlier?"

"No secrets here," she said brightly.

I swallowed hard and spoke. "I heard both of you finish, like pretty close to each other. Were you using your hands on each other? Or... toys?"

"Ohmigod... sweetie," she laughed, "I think you have a fairly good understanding about what's inside Quinn's panties."

"Yeah, obviously..." I said, raising an eyebrow.

Sloane simply sat silent and let me struggle. "Quinn has a penis. I have a vagina. Those parts still fit together pretty well."

"Ohh..." my eyes went wide. A whole new set of exciting images permeated my thoughts. "Jesus, I'm an idiot. I thought..." I stuttered, "I thought maybe she wouldn't wanna do that any more."

"It's okay, I'd kinda wondered about it too. But, she was still alright with that particular activity still being on the menu. Quite enthusiastic about it, actually."

"Interesting." My cock responded and started tenting my shorts again. "Is it weird if I say that really turns me on?"

"That your girlfriends just had sex while you listened? Or that one of them left a nice load inside the other?"

"Both..." I managed to squeak out. My universe expanded a tick as I stared at her. Of course, my subconscious blurted out the first thing that came to mind. "Was it weird, you know... you guys were together before. Just like that, but she was..."

"A he." Sloane took a deep breath and exhaled. "A little. But I'm getting used to it. I mean, I've had two years to think about it."

My mind wandered back to the concocted images of them together. I was fully hard now, my cock poking down the leg of my shorts. I shifted uncomfortably.

"Does someone else need a little attention?" she asked, raising an eyebrow.

"If you're offering."

Sloan reached over and rubbed me through the thin fabric.

"I'm offering. Would you like me to suck you off? Or if you don't mind a little extra mess..."

"I think the second one."

She stood and took me by the hand. "Probably should move away from the glass."

I followed her to a chaise lounge toward the back of the rooftop.

"I'm glad none of the neighbors use their decks," I said, pulling my shorts off and laying on my back.

Sloane grinned and gracefully swung a leg over the bottom of the chaise before getting on with me. She hiked up her dress and scooted above my cock.

"You're not wearing any panties, I see. I almost think you came up here with ulterior motives."

"Maybe."

Just then, a thin trail of milky liquid dripped from her, falling perfectly in a stripe on the underside of my shaft. I watched in lust as her pussy released more of Quinn's juice onto me.

"Oh, sorry about that," she said in a tone of voice that very clearly telegraphed she was not sorry. "The dangers of sloppy seconds."

"Fuck..." I murmured. Envisioning Quinn's large cock between Sloane's legs just minutes ago stoked my arousal even further. Sloane grabbed my shaft and slowly lowered herself onto it. More cream oozed out and onto my skin as her lips stretched around the base of my tool. "God, I love being inside you."

She purred and began to move her hips. As she slowly impaled herself on me, the copious load began to drip down my cock and pool on my flat stomach. I dipped my finger into the growing mess and brought it up to her clit, using the natural lubrication on her button.

"Oh, that's nice..." she cooed.

I continued gently stroking her clit as she rode me. After a few minutes her strokes were longer, just the head of my engorged cock parting her cunt lips before she let gravity take her back down around me. I'd scooped up the majority of the leftover cum and smeared it into Sloane's slit when she climaxed.

"Oh, shit, Jack... cumming! Cumming so good!"

She slammed down onto me one final time and gyrated her hips in tiny circles while I rubbed her button. I slowed my ministrations, taking lighter and lighter strokes with just my fingertips as her aftershocks tapered off.

"Jesus..." She glanced down at me and sighed. "A girl could get spoiled like this. Are you close, baby?"

I shook my head and got a lusty grin in return. Still inside her, I sat up just enough to take off my shirt. I reached up and pulled the cups of her sundress down, her tits now free of the stretchy fabric. Gently pulling at her shoulders, I guided her body against me and kissed her deeply. I wrapped my arms around her and just held her for a moment.

"I think I like sloppy seconds," I whispered in her ear. "Now I'm gonna make you even more sloppy..."

Sloane murmured an assent.

I moved and planted my feet up on the chaise to get additional leverage. I began slowly thrusting up from below, sliding in and out of her warm tunnel. I went slow while I held her against me, perfect breasts pressed into my chest.

My slow, measured strokes took a few moments to get me there. I had my eyes closed and simply focused on the feeling of our bodies together. The mental image of Quinn's large cock in the same place as mine was so hot... Getting close now. Before long the familiar sensation began inside, the delicious pressure and urge to make her mine. My body increased tempo on it's own.

"I'm almost there," I grunted. "I'm gonna fill you up again..."

"Please," she pleaded. "I want it."

"Fuck," I growled, pounding upward even faster now, "I'm gonna cum..."

I got two more deep strokes before my seed rocketed out. My hot cum joined the rest inside her body, mixing together and coating my shaft. As my spurts slowed, I took short stabs, pushing my cock and our mixed loads deep into Sloane's pussy. I finally released my last volley and slumped back into the chaise.

I sighed and slowly rubbed her back.

"That was way better than homework."

She kissed my ear and whispered. "You wanna shower with me?"

* * *

We were all off school and work early the next afternoon. Sloane was doing something on her laptop at the bar, Quinn and I were on the couch trying to find something to stream. We'd each polished off a beer before Sloane came and grabbed the remote, apparently tired of our lengthy discussion about what to watch. She picked some kind of blockbuster dinosaur flick, I think one of the Jurassic Park movies. I wasn't really paying much attention.

After two more beers each, Quinn and I were comfortably numb. We'd turned to face each other on the couch and were just talking. I was at the perfect inebriation point to be a bit philosophical, but unfiltered. I'm not sure where it came from, but I blurted it out all the same.

"Do you ever miss being a guy?" Sober me would have never asked. One-beer-ago me would have added no offense on the end.

Quinn raised a darkly shaded eyebrow at me. "Like how?"

"I mean..." I tried to collect what disjointed thoughts had been swirling. "Like being able to go out in grubby clothes, not having to smell and look nice all the time."

"I suppose it is more work," she said introspectively. "But there really great things too. For starters, girls get way better clothing options. And the nicer you look, the nicer people are to you. People hold doors, and you can order a fruity drink at a bar without the bartender thinking you're a wimp."

Sloane shut her laptop and joined us in an armchair, obviously more interested in our conversation.

"Okay, all fair points," I conceded. "I just can't imagine having to go through all the extra hassle." Come on Jack, you're about to cross a line. Don't make her cry again.

"It's not like I'm changing who I am underneath. I just feel better when I look pretty, like my outside reflects my inside. Does that make sense?"

"I think so. I guess I understand the outside part." I absentmindedly touched the barbell piercing in my eyebrow and thought about the number of times I'd stared at my new reflection in the last week. "Isn't in weird though... seeing a different person in the mirror?"

"Every now and then," Quinn trailed off. "There are a few things I really missed from when I looked different. Well, some I get to do again now..." She glanced nervously at the floor.

"Yeah?"

She took a long pull on her beer and grinned. "Like plowing Sloane and hearing her beg for my cock."

"I heard that."

"We should have talked about it first. I hope it didn't weird you out."

"Made me pretty frickin' horny is what it did..."

"I took care of it," said Sloane offhandedly.

We all giggled and finished our drinks. Sloane joined us on the couch and snuggled between us. We finally started watching the movie as the action ramped up. I watched as a group of people was running through something like Disneyland Main Street USA, but with dinosaurs in pursuit. The attractive redhead running in high heels next to Chris Pratt sparked some less than proud memories.

"Jessica Chastain..." I mumbled. "Damn."

"Wouldn't have thought you were into redheads," said Quinn with a giggle. "I mean..." she gestured between her black and Sloane's blonde.

"Equal-opportunity man whore," I said. They both giggled.

"Well you're not wrong," said Quinn, "Ms. Chastain is smokin' hot, but that's not her."

"Of course it is, I happen to have some experience with that particular redhead..." I grinned.

"That's's Bryce Dallas Howard," said Quinn. "You know, Ron Howard's daughter?"

"Shit, the guy from Happy Days?"

She nodded back.

"No way in hell. You're telling me Richie Cunningham somehow produced that? I call bullshit." I reached for my phone.

"Hang on," said Quinn, batting at my hand. "You wanna bet?"

"Absolutely. I'll even let you pick the wager."

Quinn crossed her arms and narrowed her eyes at me for a minute.

"Okay. If you're right, I'll go out for a whole evening dressed as a guy." A devious smile started to curl her mouth upward.

I gulped, knowing what was coming, but put on my best poker face.

"But if I win, you have to go out as a girl. Regardless of the outcome, this will be an observational lesson for you on the differences between genders in our society."

I studied her face. She was as confident as I was.

"Fine, deal." I glanced over at Sloane, her phone already out and wearing a better deadpan than me. She handed it to me, the screen already open to the movie's IMDB page.

"Bryce Dallas Howard," I read numbly. My stomach twisted in a knot as I stared at the name. I pinched to zoom in to the obviously full-genetic copy of my Jessica. "Well, shit." I gave the phone back and realized my hand was shaking. I couldn't tell if I was terrified, excited, or both.

Quinn must have seen the turmoil in my obviously transparent reaction.

"It's fine," she chuckled, "you don't have to do it. It was a dumb idea anyway."

"No," I steeled myself, "a bet's a bet."

My mind reeled as I thought through what I'd just said. What the fuck am I doing... why am I agreeing to this? I'm not gonna leave the house dressed like a chick. The thoughts continued to swirl. What if some asshole decides to kick my ass for cross dressing?

What if... I like it?

"Never mind," old me blurted out. "There's no way I'd pass for a girl anyway."

"Are you challenging our styling skills?" Sloane giggled.

"I uh..." I stuttered. Half of me wanted to bolt to my bedroom, the other half was beginning to tingle with some emotions I didn't recognize.

"How about we make it Friday?" said Quinn. "It's Halloween. If someone flicks you shit, you can just say it's your costume."

That would work, I thought. Do I need to argue more? Why is this exciting? I realized my mouth was hanging open a bit and they were both staring at me.