California Dreamin' Pt. 06

Quinn softened as she gazed into my eyes. "I could dress as guy Quinn and be your date if you want."

"But you won the bet."

"I just thought it would maybe make you more comfortable..."

I nodded and lunged forward to hug her. "Thank you," I said quietly into her ear. "Jesus, you'd think I was some kind of closeted transphobe or something."

She pulled back before giving me a gentle kiss. "Jack, you've already disproven that beyond any shadow of a doubt."

* * *

The next week was a roller coaster. I'd be lying if I said the prospect of Quinn's bet didn't terrify and arouse me in equal measures. Well... depending on the day. Twice I had resolved to march upstairs and tell them that there was no way I could do it. Most of the other conscious hours though, I marinated in something closer to nervous anticipation. Kind of like getting ready to travel to a foreign country you've never visited with no itinerary and no idea how to speak the language.

I felt rather horrible one evening after stumbling into an online forum of trans people in their teens and early twenties. Most of them had existences so much worse that Quinn's, many quite literally thrown out of their own homes or had their lives threatened simply because of a choice to change the way they looked. The stories of what some of them did to survive and find validation nearly broke my heart. I'm doing this on a dare, for a joke. I finally had to get up to stop the tears from dripping into my keyboard. I wordlessly slunk into Quinn's room and crawled under the covers next to her. She didn't say anything, but just let me hold her.

I woke the next morning in her bed, remembering something she'd said while we were tipsy and arguing about beautiful redheads. I was going to very temporarily experience an evening presenting as the gender opposite my upbringing. Why not just treat it as a societal experiment like she said? If nothing else, maybe I'd understand her a little better. I was clearly fine with being sexually attracted to a girl with a penis. I was also okay with her presenting as a guy. But did it matter that I knew her first? Did the junk between our legs have anything to do with our clothes and haircuts? I thought I had answered all my own questions already, but that assumption got tossed out the window. The implications swirled around my brain until I forced myself to go get ready for class.

Walking home that afternoon, I had a minor freakout and realized I had no idea what to do with my voice. If I was going to be even remotely passable, I'd need to be able to speak. With a couple of shifty glances up and down the empty sidewalk, I started practicing. By the time I got home I'd made some progress. I sounded better, but still forced and obviously not female. I locked myself in the bathroom and found couple of Youtube videos, because of course they existed, and took a half an hour mimicking sounds into the mirror. I was actually a bit shocked by the time I finished and tried everything together. I closed my eyes and used my phone to record myself. When the sound played back from something other than my own vocal chords, I sounded like someone else. And almost imperceptibly, not a guy.

Friday morning finally came. I woke early and forced myself outside for a run. The endorphins helped my anxiety, but the anticipation nearly made my stomach cramp. I bounded up to the kitchen to get some juice and ran into Quinn. She'd obviously just gotten out of bed, no makeup and nondescript sweats and a t-shirt. I noticed her lack of curves just as she held a small plastic case out to me.

"I was just coming to find you," she said, handing me the box.

I glanced between her flat chest and the case.

"My girls, for you to wear tonight."

"Oh, I figured I would just wear your old ones..."

"It's okay, it was time to redo the adhesive anyway. Besides, these look way better."

"Thanks baby," I pulled her into a hug, the strangeness of the situation not lost on me. "Sorry, I'm all sweaty."

"I don't mind," she grinned. "Here, I got you this too." She extracted a pair of flesh toned panties from a pocket. "It's called a gaff. It helps—"

"I know what they do," I interrupted. "I've been reading up a bit."

"Have you now?" she said with an eyebrow raise. "How studious of you."

"When Jack Thornton does something, he goes all in." I realized the swagger in my voice and hid my face behind my glass of orange juice.

"Trying to get in some last-minute masculinity by chance?"

"Maybe." I grinned. "Are you still okay going like... this?" I said, giving her a full-body stare.

"Yeah, I'm even going to work. Nobody there cares, it's pretty awesome actually."

"Any thoughts what we're gonna do tonight?"

"I dunno," she answered, popping some bread in the toaster. "Whatever you're comfortable with. No pressure."

"I kinda wanna look nice. You know, fancy."

"Fancy, or slutty?"

"Maybe some of both?" My cheeks warmed and I stared at the floor. "Is this, like... weird for you? I mean, dressing as the opposite gender for the first time was a huge turning point in your life. I'm doing it because I lost a bet. It feels kinda disrespectful."

"Sweetie," she said, wrapping her arms around my waist, "you are literally the most respectful, accepting, open-minded person I know. I wanted you to do this, to peek behind the curtain a little bit."

"Okay. I just..." I trailed off.

"Besides, seeing my heteroflexible cutie-pie boyfriend all femmed up for a date... I can't say I'm not excited."

"Well, as long as you're okay with it. I was thinking Sloane could help me get ready. You know, so you could see the finished product all at once."

"Jesus, you're adorable," she grinned. "Of course, she'll do a great job. I can't wait to see how fuckin' cute you look... wow, I'm not even guy'd up and I'm already talking like a sailor..."

I kissed her and went downstairs to shower.

My handful of classes that day were a total waste. Other that getting to see a few half-baked costumes, there was little redeeming value to my attendance. There's no way I could pay attention, and Sloane's incessant texting that we should go get you ready made it nearly impossible to stay. I finally relented halfway through the last lecture, glad that I'd sat near the back.

"Apparently you're all aboard the crazy train too?" I said as I stepped out, she'd been waiting for me outside.

"Makeovers are the best!" She said, elbowing me in the ribs. "And you were the first one to jump on the train anyway, remember?"

"Yeah, yeah... I still think I'm gonna look like a fraud and not want to leave the house."

"I wouldn't be so sure about that," said Sloane seriously.

"Fine. I'm putty in your hands," I added dramatically.

We strolled home and found Quinn just walking in from her Starbucks shift.

"Oh hey you guys. How was class?"

"Meh. Work?"

"I had a Karen yell at me when they forgot to warm up her coffee cake, but other than that, not bad. So I was gonna go shopping on the way home, but figured maybe I could just borrow some of your stuff?"

"Go for it," I said. "I'm obviously not gonna need any of it tonight." I laughed nervously.

"What time are you guys wanting to leave?" asked Sloane wistfully.

"You guys? Aren't you coming with us?"

Her face brightened. "Oh, I thought this was a date. You sure you want me along?"

I pulled her in and kissed her gently. "Of course you're coming! You'd never forgive yourself if you didn't witness this shitshow in person... What if I need someone to help me touch up my mascara or something?"

"Or go with you to the bathroom. You know we do that together..."

My eyes went wide, clearly I'd not thought through all the implications of the evening. "Yeah," I gulped. "Actually, Quinn should weigh in here. He's the one that's gonna have to deal with two girlfriends hanging on him. That can be exhausting..."

We laughed and did a time check. We'd leave by five, but wouldn't make any specific plans. Just see where the evening took us... Quinn headed for my room and Sloane took me up to hers, mumbling about three hours might not be enough time.

She sent me to the shower first, with a bottle of shaving gel and a fresh razor. I re-did my face, then moved on to my legs and armpits. She sat outside the shower and chatted with me, impressed how fast I was. The pre-race swimming ritual came back to me easily and I watched the stubble rinse down the drain. I did the peach fuzz on my chest last.

Next was all-over body lotion, the same nice floral scent she used. Then Sloane let me pick nail polish. The shimmery lavender I chose was called Nebula. After watching me trying to paint the first one, she took over. I stared at my fingers as she worked on my toes. Even the tiny pop of color on my body felt different.

"We might not have shoes for you... I think Quinn's feet might be a size smaller. We'll have to plan outfits accordingly. What kind of look were you thinking? More like Quinn, or more like me?"

"I dunno," I said thoughtfully. "Maybe somewhere in the middle?"

"I can work with that. I guess we should probably do these next," she said, nodding at the box containing Quinn's forms. "You ready?"

I nodded. Sloane took out the faux breasts and read the instructions inside. After carefully brushing on the adhesive, she held the first one up.

"Here goes, get ready to say hi to Jackie."

"Jackie?" I said aloud. Shit, I hadn't even thought about a name.

"Would you prefer something else? Seemed like the natural choice..."

"Alright yeah, it's fine."

"Okay, here goes..."

She lined up the form and slowly applied pressure against my chest. I felt the adhesive grab my skin while she slowly pressed around the thin edges. I deliberately looked away until she'd attached the other. The weight on my chest was an odd sensation, but not unpleasant. She darted into the bathroom and grabbed some concealer.

"The color is pretty close, but this should help. Hold still." After a few minutes she stood back and studied her work. "Wow, not bad. Nice tits, girlfriend!"

I stared down at my breasts, my perky nipples pointing out from my body. "I can't see my feet," I giggled.

"Welcome to the club."

I glanced into the mirror and gazed at the first step of my transformation. "God, they are nice, aren't they?" I reached up and cupped a hand under each breast and felt their pleasant weight. I shook my shoulders, the unfamiliar sensation making it feel like my center of gravity had changed. I gently pinched one of my nipples. Even though I couldn't feel the sensation, I could feel my cock responding.

Sloane arched an eyebrow at me. "So, clothes... do you wanna come help me pick stuff?"

"Nah, I trust you."

While Sloane was gone, I took the opportunity to tuck. Of course I'd heard Quinn describe it, but watching the video and putting it into practice were quite different. Pushing my testicles back into the canals they dropped out of was an interesting experience, but not horrible. Next came the underwear she'd bought me. The shape resembled an almost-sexy high waisted bikini bottom that arched up just over my hip bones. With some wrangling, I pulled them up and tucked my cock snugly between my legs. The effect, staring at my reflection in the mirror, was instantaneous. The V shape created by the panties further visually reinforced an hourglass shape, my new tits taking care of the upper curves.

Sloane returned with an armload of clothes and dumped them on the bed. She dashed into her closet and fetched another pile.

"Okay, we have some choices. I figured since you went to the trouble of shaving, we should look at dresses. It's supposed to be decently warm tonight, so you should be okay."

I nodded. She spent the next fifteen minutes holding up clothing against me, switching back and forth between the shrinking number of candidates. I ended up choosing one of Sloane's dresses that we agreed was a good blend of fancy and slutty. The dress was simple, dark gray with a halter neck. The opening in the chest showed some nice cleavage, and the slit up the right side showed my thigh nearly hip-high. I stared at myself in the mirror and gawked at my body. The head on top of the skin tight dress was definitely still Jack.

"Wow..." I said slowly. I could feel the my underwear pressing against the beginnings of an confusing hard on. I'm wearing my girlfriend's dress.

"Wow is right," said Sloane. "It fits you perfectly. I didn't realize you had the hips to pull that off! Alright, on to makeup and accessories. Do you want to watch while I do it, or see it at the end?

"Hmm..." I debated, both interested to watch the process, but also wanting to enjoy the surprise. "How about the end."

"Okay. Have a seat then."

Sloane started on my hair, applying product and teasing it with her fingers and a couple of different brushes. Makeup was next. I had some recent experience going out with Quinn, but this time was definitely more.

"You alright with some extra jewelry?"

I nodded and she added a magnetic earring to each lobe, and small silver ring to my nose. My actual piercings stayed.

"Quinn's feet are only a size smaller than yours, so I'm hoping these will work."

She grabbed a pair of flat-soled sandals from the bed. They were mostly black, and had rhinestones on the thin straps. I slipped them on and only had to adjust them a bit. I stood and took a deep breath and let it out. Now I'm wearing my other girlfriend's shoes.

"Wow..." she said again. "Well, I think we're there."

"How bad is it?" I asked nervously. "Is anyone gonna believe this?"

She flashed me an amused grin. "Go on and look, see for yourself."

I closed my eyes and turned toward the mirror. I took another deep breath and peeled my lids open.

Holy shit, that's not me.

My normally relaxed hair was teased up in a stylish, spiky do, and my makeup was impeccably applied. Sloane had matched my skin tone perfectly with base and powder, but went dramatic on my eyes. They were heavily lined and shadowed with a smoky gray that went with my dress, and just a hint of pink at the top. Mascara and more liner made my lashes and eyebrows pop. The final touch was the deep, red lipstick.

I opened my mouth and couldn't think of anything to say. I cleared my throat and almost without thinking, changed my voice.

"Hi, I'm Jackie. Lovely to meet you." The hair on my neck stood up at the combination of my voice and visual transformation. I am literally someone else. My cock was now straining uncomfortably against the gaff.

"Jesus!" said Sloane, clapping a hand over her mouth. "How did you do that?"

"YouTube," I answered in my new voice. "How do I sound?"

"Amazing... has Quinn heard you yet?"

"No, I was going to wait until everything was done." I moved closer to the mirror and continued to gawk at myself. "I honestly can't believe this... does it really just take makeup and jewelry to be... beautiful?"

"Honey, you were already an awfully pretty boy..." Sloane giggled.

"I guess so," I said, still dealing with the cognitive dissonance of my previous self image and what was in front of my eyes now. "I imagine Quinn has been ready for awhile... we should go get the freakout over with." I took one last glance in the mirror, flashing myself what I hoped was a sexy smile.

I walked down the stairs and could hear the TV on. Quinn was on the couch watching the news, the weather girl trying to make another afternoon in the high seventies sound interesting. I cleared my throat and he popped up.

We stared at each other for I wasn't sure how long. I'd seen him in sweats and t-shirts before, but a nice pair of slacks and a rich blue button-down took him right back to the photo I saw on his phone. His hair was neatly styled close to the head, and a number of piercings had been taken out. A little tasteful liner highlighted his eyes, but all in all, he looked rather like I did a few hours before.

"You look amazing," he said slowly, his voice deeper.

My jaw sagged open when he spoke. I'd never even considered that he'd changed his voice like I had just now. Idiot... of course he did. Like my transformation, it added another layer to the reality of it.

"Thanks, you too."

Quinn's mouth mirrored my surprise. "Ohmigod, you even sound amazing. It took me like a month! I had to practice for a few minutes just to get this back..."

"I wanted to be believable for you," I said. "What do you think of everything else?" I did a quick spin, the dress flared out just a bit around my smooth legs. I blew him a kiss when I came back around.

"I'd say Sloane is makeover genius. I mean, she obviously had a pretty sexy canvas to work with..." He glanced at Sloane, still beaming at her work. "Are you gonna get ready? You're still coming with us, right?"

"Yup, gimme like ten minutes." Sloane disappeared up the stairs.

Quinn rounded the couch and took my hands. He rather unabashedly gave me a close-up examination, including the seams of my breasts.

"I think you're a prettier girl that I am..."

"Oh, stop. You're still my hot emo princess under there." The longer I spoke with my new voice, the more comfortable it became. I rested my lavender-tipped fingers on his chest. "I really like that shirt, haven't had a chance to wear it yet. It looks good on you." I felt the urge to kiss him, but knew my lipstick smudging his face wouldn't improve the outfit.

"So I was thinking maybe just go out for drinks first, then see what happens?"

"Sounds good to me." I stared into his eyes. I knew it was the same person, the cute alt-girl I fell for weeks ago, the one I'd already shared so much of my life with. The feelings were the same, but looking at him now added something else. Something new.

"Okay there?" He asked sweetly. "You looked kinda checked out for a minute."

"I'm good. This is all a little... strange."

He grinned widely. "I know. Remember, this is all just clothes and makeup. We're still us. I still..." he cleared his throat and trailed off.

"Let's blow this joint!" Sloane called from the stairs.

She strolled through the kitchen looking radiant, a strapless baby blue dress showed her curves and her blonde hair fell over her shoulders. The pink lipstick was an adorable counterpoint to the look.

"You look yummy!" I said, turning to hug her.

"So Quinn, you ready to show your girls a good time?"

He pulled us each in for a hug. "Absolutely."

A fleeting thought popped into my head as we reached the bottom of the stairs.

"Gimme two seconds, need to pee before we go." I darted into my room and went to my nightstand. With a glance over my shoulder, I grabbed the butt plug Sloane had given my and a small bottle of lube. I disappeared into the bathroom and with a rather unladylike leg propped up on the toilet, gently rubbed some lube around my opening. I smeared some more on the toy and pushed it against my puckered hole. Just breathe. I relaxed and pushed slightly against the plug. With a slow stretching, it popped inside and snugged the bejeweled base against me. Oohhh, fuck. I exhaled and pulled my dress back down, flashing myself a naughty grin in the mirror.

I rejoined them in the entry, trying to keep a straight face as the toy's girth made me feel deliciously full. "I'm ready now."

We walked out into the warm late afternoon air. Friday rush hour traffic clogged the streets, and a few families with small children in costume were already wandering our neighborhood. I got a little thrill as we walked, getting an obvious eye grope from a young guy in a convertible Mustang. I absentmindedly swayed my hips just a little more as we walked by, envisioning his probably laser-like focus on my barely covered ass. I wondered briefly if the makeup would still show my blushing cheeks.