California Dreamin' Pt. 03

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Jack's new life takes a left turn.
25.9k words
4.78
9.5k
14

Part 3 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.

Whew, I'm still a little hot and bothered with the answer to the 'will they or won't they' from chapter two.

As promised, chapter three is where things start to get interesting. We'll meet a new character, get some more history, and get to see Jack's world turned upside down a bit. 'But he just got with Sloane!' you say, 'They seem so good together, or whatever the hell it is they're doing.' You're not wrong, but life has a way of throwing us curveballs. It's all about what you do with new opportunities...

This, and future chapters, will add themes of trans/fluid-gender, bisexuality, group sex and poly things, cross dressing, and some light drug use. If any of these offend or trigger you, please look elsewhere. If you're willing to try and catch that curveball, you might just like it.

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.

This one is will be a bit (a lot!) longer, you might want to put on some water for some tea.

* * *

I went back to class on Wednesday. Despite taking the best skip day ever, I knew whatever was happening with Sloane was only part of my life. I had university, a future career, a life probably not in California...

And that's the story I fed myself the entire walk that morning. The truth was, I couldn't stop thinking about yesterday, about her. I'd given away my V-card in the most stunningly unlikely scenario I thought possible. Sloane was a California goddess, and I was a skinny kid from Michigan.

Aside from offering my body more physical pleasure than I'd ever had, in the span of a few minutes she had psychoanalyzed the artificial person I'd created and helped me see the truth that somehow eluded me. Sure, new me was responsible for the crazy turn of events that got me here, but he also overcorrected toward the macho doofus that I thought was what the world wanted and rewarded. She helped me see that taking worthwhile risks and being honest didn't have to come along with all the other 'alpha' bullshit I'd built up.

One of the traits I kept in the transition to real me, was the uncomfortable willingness to just go with it. Don't let expectations ruin something because it's not what you thought you wanted. It sounded so easy when I just got out of my own head. Case in point, was yesterday. Yes, we got to have what I assumed was pretty amazing sex, and I got to feel closer to another human than I thought possible, but it didn't need to get labeled. It was what it was.

Jack, you're the best thing that ever happened to me and I want to spend the rest of our lives together making each other physically and emotionally happy... is what I would have loved to hear, but that wasn't what was said. Instead, I convinced myself to simply keep adding to the tally of awesome things that my new life had racked up. Bright future, living in SoCal, beach house, first ever sex with hot roommate. Seemed like a pretty good list.

My Econ study partner seemed to know right away that something had changed. Maybe it was the plastered-on grin, maybe my new outlook on life, who knows. She asked, point blank as we walked out of class if I'd gotten lucky.

"Just played hooky yesterday and went to the beach," I offered. She raised an eyebrow and shook her head.

The next few days seemed as normal as they could have been. Well, normal as in we were still roommates, hung out, ate together, and generally got along great. We kissed goodnight, and sometimes in the morning while I cooked breakfast. I got bold once when we had snuggled on the couch to watch a movie, and rested my palm over one of her beautiful C-cups. She didn't squirm or pull away, but didn't push me down and fuck my brains out either.

I began to wonder if our tryst was going to stay in the history books a one-time thing. A moment of weakness on her part, an itch that really needed scratched. I decided that worst-case, having that memory in the spank bank was damned good enough. If it happened again, fan-freaking-tastic, but I didn't need to turn our relationship in a bad direction by pushing it. I loved living with her, and for all intents and purposes she was my best friend. We still finished each other's sentences, ate off each other's plates, and sometimes just hugged or held the other person on the couch or rooftop. I couldn't fathom rocking that wonderful, sexy boat, so I just sat quietly and enjoyed the ride on the SS Sloane.

Another week went by, and life was good. We walked home together from class that Friday, and within seconds of waiting for a lull in the conversation, blurted out that we each had dates that night.

A guy from the university lacrosse team had asked Sloan out as she sat in the quad. She thought they might have had a class together the previous year, but couldn't remember for sure. Despite looking the part of a sports bro, she said he was very polite and seemed intelligent and well spoken. He invited her to some kind of pop-up art show near Newport Beach and then to dinner, you know, if she was hungry.

I was rather proud that I'd initiated my date, I think subconsciously as a way to show her, us, that our casual hookup was just that - and that our lives should continue on, outside the strange, sexy bubble we created that random Tuesday.

Every the day I'd walked in glowing, my econ partner had ratcheted up the flirting game, which I was happy to play. I finally just asked her out. My activity was decidedly not as chic, another stroll down the boardwalk with ice cream and maybe a food cart sandwich. Sloane told me about a new one she'd visited earlier in the week and pinned the location on my phone.

We both strolled into the kitchen early that evening, dressed for our respective outings. Sloane had her hair in a loose tie, and had put on a cute pink lipstick. The short yellow sundress was flattering, but not overly revealing.

"You look really nice," I said as I rounded the island toward her.

"You too," she offered. "I just love those shorts on you..."

My entire outfit was stuff she'd bought. I had to admit, it made me look alright, especially the way they showed off my toned swimmer's legs.

"You headed out soon?" I grabbed a water from the fridge and took a sip.

"Yeah, you?"

I nodded back. She stepped in and closed the distance between us.

"I hope you guys have a good time. Jaime, right?"

"Jana. What's your guy's name?"

"Chad," she grimaced.

"Are you serious?" I grinned and tried to not giggle. "Wow..."

Sloane smirked. "It's just a date."

"Well, here's to good dates," I lifted the water and took another gulp. She took it from my hand and did the same. We were still very close. "I do hope you have a good time, for real." I added quietly. I stared into her eyes and hoped my expression said the same. Before I knew it, eyelids drooped and we were kissing. I let it happen and waited for her to pull back.

"You too." Sloane smiled warmly. "Oh, shit... sorry about that." She turned to the bar and grabbed a tissue. "Can't go out with another girl's lipstick all over you. Not a good way to start a date."

"I suppose not." I hugged her close and we said our goodbyes.

My evening went really well. If it had been a month ago, I would have said it was the best date ever. Despite repeating activities I done many times, we had a nice time. I bought chicken tikka empanadas, Jana bought the ice cream. We sat on the beach and watched the sun dip below the horizon. The conversation came easily and I even made her laugh a few times. I tried to keep the inevitable comparisons away, but of course they were there. She was pretty, the golden hour rays giving her auburn hair luminous highlights. When a cool breeze picked up, I wrapped an arm around her shoulder. She snuggled into me and we finished our dessert.

We walked the boardwalk for a bit until we apparently ran out of things to say. I was gentlemanly and offered to walk her all the way back to the dorms. Reading a twinkle in her eye, I leaned for a kiss as we stood on the sidewalk. Jana responded with a chaste few seconds of lips pressed against mine, and a contented sigh. She thanked me for a nice evening and went inside. No look over her shoulder. Huh. Well, at least it wasn't awful. I began the hike back toward the house, trying to decide whether I was pleased or disappointed.

The house was empty when I returned. I grabbed a beer and went out onto the patio. I loved watching the activity below from three floors up. It was still decent people watching, and the boardwalk always had some kind of excitement in the evening. I nursed my beer for over an hour until I watched a car pull up. Sloane exited the passenger seat and waited for the driver on the sidewalk. They milled around the gate for a moment before he went in for the kill.

"Fuuuuu..." I realized I was slurring a quiet cursed as I creeped on their date.

Chad was holding the sides of her head like palming a basketball, fingers spread wide over her hair. They kissed for at least twenty seconds, not that my estimation of time was probably accurate just then. I was subtly proud that I didn't fly into a jealous rage, but watching them wasn't going on my awesome things list either. She finally pulled away and laid a hand on his chest. I raised an eyebrow, seeing a large patch of curly hair through his way-too-many open shirt buttons. Eww.

Sloane finally turned to come inside and I spazzed backwards to get out of view, just in case. I managed to knock my beer bottle over in the process. Shit, I whispered, almost certain they'd heard. I dashed inside and disposed of the evidence, and had sat down very casually on the couch when she appeared from the stairs.

"Hey Jack, I'm home," she called.

I popped up and walked toward her.

"But you already knew that," she snorted.

"Okay, fine." I laughed. "I was already out there when you guys pulled up, I just didn't... leave."

"This is your house too. Well, what did we think of Chad?"

"Well, he got some decent smoocherinos at the end, so he couldn't have been terrible." I giggled, half-questioningly. Sloane flashed me a smirk. "But, ohmigod, that chest hair."

"Jesus, right? There was so much, it was just spilling out. Like honestly, have you heard of manscaping? And he was just so... beefy. I like muscles and all, but take it down a notch."

"But it was okay?" I asked seriously. "He treated you alright and wasn't a total Chad?"

"He was fine, I mean there coulda been a second date. I had to do most of the talking. And he drove like a maniac... but enough about all that. How was your evening?"

I plopped back onto the couch and Sloane sat next to me, legs criss-crossed. "It was fine. She was super nice, we talked and ate. Hard to have a bad time on the boardwalk if there's ice cream involved."

"True, true. And after that? Was there any..."

"I kissed her," I forced out. I could tell my cheeks gave it away before my words.

"I'm so proud of you!" She lunged forward and hugged me. "See? Being assertive, getting outside your comfort zone while still being charming, cute Jack."

"Thanks," I smiled.

"Well, how was it?"

"I mean... it was a kiss. Alright, I guess."

"Yeah, I hear that." Sloane sat back and gazed at me. "Dating can be a grind sometimes. It's great to meet new people and all, but it can be exhausting when things are kinda meh."

"How are you so good at all this relationship stuff? You're like what, ten months older than me? And all that stuff you helped me with, new me bullshit... you just cut through it and fixed me."

Sloane giggled. "Well, I don't think I ever mentioned, but my first year of uni was behavioral psychology. Seeing how people work and what motivates them makes it a lot easier to communicate and..."

"What?"

"Manipulate is the wrong word..." she said thoughtfully. "Help people get what they want. Like, in a good way."

My brain raced with thoughts and questions. One, I was obviously glad that she used her superpowers to help me. But I began to play back our conversation and realized every word she spoke was probably more deliberately chosen than most people. Do I even ask? Don't push, remember? But she's said before in different ways, it doesn't -have- to be more. As in... it could?

"You okay there Jack? Looks like you're thinkin' real hard."

"Yeah, kinda," I said quietly. I reached out for her hands without realizing it. "I'm not a former psych major so I don't always pay that much attention. But a couple of times you've talked about us, and... something more." I bit my lip and tried to find the right words.

"What does that mean to you?"

I pursed my lips and took a deep breath. "Well, when I asked about your date, you said there coulda been a second one." I paused, she gave a tentative nod. "But that given the current state of— us?" I choked out, "that maybe you wouldn't want to let Chad manhandle your head again." God, what am I doing...

Sloan laughed brightly. "Pretty good analysis. Go on..."

"Well, we both have been on dates with other people. And, we had sex, you and I." The air between us seemed to get thicker. "Which I really enjoyed, by the way."

"Me too," she said softly.

"I guess what I'm asking, is... are we doing some kind of roommates with benefits thing?"

She smiled sheepishly. "I didn't wanna just come right out and ask... look at me, not listening to my own advice. Jack, I love that we live together, and walk to class, and that you cook for me," she added. "And I really liked being with you, you know, in the biblical sense."

"Yeah," I laughed.

"But I didn't want to scare you off, thinking I was some kinda sex-crazed maniac or something. I know last week was a big step for you. I wanted to give you some time to think about it."

I laughed and leaned back. "Oh, I've thought about it. Sometimes twice a day."

Sloane's eyes went wide for a moment before she giggled back. "Wow, I must have made an impression!"

"You could say that. So, I'm gonna be direct and honest here." The beer gave me just enough courage to get it out. "We're agreeing to be roommates that still have a fabulous time together, that are okay leaving the food prep to me, date other people when we want, and sometimes fuck."

She took a moment, but gave me a lopsided grin. "Yeah, that."

I felt a surge of pride, being mature an honest about something as huge as this. I was able to just put out there what I thought, leaving my juvenile feelings behind to have a real, if complicated, adult relationship.

"So where do we go from here?" I asked.

Sloane cocked her head slightly. "Whaddya mean? We're already there, right? What you just said."

"I meant about the sex part." I realized I still had her hands in mine and let them go. "Is there some kind of schedule, or code word or something?"

She laughed. "Oh Jack, there doesn't have to be any rules. It should be beautiful and spontaneous. We'll just do what comes naturally when the mood arises."

I sighed deeply. "Okay, I can live with that."

"Good, because the minute I stepped through that door I wanted to try and jump you." Sloane leaned forward and kissed me, uncrossing her legs as she moved toward me on the couch.

Our hands and arms pulled us closer together as we began to make out.

"Like right now?" I mumbled distractedly.

"Are my signals unclear?" Sloane giggled and began unbuttoning my shirt.

"Chad must have done something right with that kiss," I offered, helping her with the rest and pulling it off. My cock grew quickly.

"Oh, yummy," she eyed my half uncovered body. "Nice and smooth."

Her hands were all over me as we continued kissing, lips and necks and ears. After a few minutes she straddled my waist and sat on my lap, facing me. She ground against me as I kissed down her bare shoulders and over her collarbone. Our breathing got markedly heavier.

"Do you wanna go to my room?"

"In a bed? That's not very spontaneous. How 'bout we stay right here?"

"Ooh, in the living room? You naughty boy." She bent down and sucked one of my nipples into her mouth, tonguing around the sensitive skin before gently nibbling at it.

I gasped at the pleasure and leaned back into the couch cushion. She switched sides, then kissed her way back up my chest. I plowed my tongue into her mouth and pulled her body against me. I forced myself to slow down and pulled away.

"Do you want me to go down on you?"

A glint in her eye suggested she was considering it. "Sometimes a quickie can be good. I just want you."

Any remaining softness between my legs disappeared. I lifted under her shoulders to raise her up, then quickly tugged my shorts and underwear off. My engorged cock flopped against my rippled stomach as she stared at me.

"Leave it on," I instructed as Sloane had begun to pull upward on her sundress. A lusty smile turned her mouth upward and she complied, the short hem falling back to her thighs. I grabbed the base of my shaft and aimed it in the air.

She straddled me again and began to slowly stroke her lips over my head, coating it in her slippery juice. We'd locked eyes as she began to drop her hips.

"Oh, fuck..." I whispered as her body began to envelop me. She stopped about halfway down, pulled up, then fully impaled herself. The yellow fabric of her dress pooled around my stomach, but the recent memory of her beautiful lips stretched around the base of my cock was at the front of my mind.

"Mhhmmm, I missed this." She began to roll her hips forward and backward, easing just a little of me out of her pussy each time. The movement was slow and sensual, almost less erotic than our frenzied kissing from a moment ago.

"God, you feel good." I wrapped my arms around her back and pulled her gently against me. She continued slowly rocking, keeping my cock buried deep inside her.

I moved one arm between us, caressing her exposed chest with my fingers. After a moment I tugged at the elastic upper hem of the dress. I pulled it down, revealing a lacy, matching yellow bra. I glared at the article of clothing and reached my hand back around her back. I fumbled my hands under the neckline to find the strap. Sloane continued to ride me while I struggled.

"Oh Jack, we need to get you some more experience with these things... maybe I did set the bar too high," she giggled. "Here, let me." She contorted her arms behind her and quickly undid the clasp. With a series of arm movements and sleeves and straps that would have confused Houdini, the bra fell to the floor and the dress stayed on.

"How did you do that?" I asked in disbelief. "Never mind, you can show me later." I resumed tugging a the front of her dress, quickly freeing her breasts from the stretchy fabric. I immediately palmed one and lifted it to my face, kissing slowly around her areola before taking as much of a mouthful of flesh as I could.

Sloane cooed a few encouraging noises as I suckled at her tit. I used my other hand to lightly pinch her other nipple, doubling the intensity of her adorable moans.

She had begun to take longer strokes, still slowly using her hips to rock and make widening circles. More and more of my shaft pulled out of her before she pushed herself back to home, my flesh bottomed out inside her.

"Jack," she breathed, "I'm gonna touch myself, is that okay with you? I know you can't reach very well.

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