Finding the Perfect Fit Pt. 01

Story Info
A tale as old as time, girl meets boy with a secret.
4.2k words
4.47
45.3k
73

Part 1 of the 25 part series

Updated 06/09/2023
Created 09/14/2019
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Joshana
Joshana
272 Followers

Whatta Night

Okay, my head feels like it's going to explode so I need to get this out. I've never kept a diary like all the girls did in shows growing up but now is the time so here it goes.

Got off work late, my job at the local gas station the usual nightmare of people not showing up or stealing stuff but it paid for pizza and caffeine so I put up with it. With Thanksgiving a few weeks away, it was getting colder and spending a Friday night at work isn't anyone's idea of a good time. I drove back to my dorm and discovered Donna, my roommate, was partying down with her fellow basketball players.

I walked into the shitstorm: horrible loud music, a beer pong table wedged in the tiny kitchen and people shouting. Blowing past some girl who tried to talk to me, I slammed my bedroom door behind me, able to feel the bass thumping from the other side.

I changed and tried to figure out how to salvage what was left of the night, it was the beginning of the weekend after all, but came up blank. The little dorm house was full of sports scholarship kids who were either getting drunk or already there. Short of burning it down, there wasn't much else I could do aside from hide in here and wait them out.

There was a knock and the door instantly opened, letting the cacophony and Donna in. Grinning, a large wet spot on the front of her shirt, she was obviously pleased with her life choices.

"Hey, why ya hidin'? Come on out, there's plenty to go round!" She was swaying slightly and oblivious to my bad mood.

"No. The music's too loud, I don't know anyone out there and fuck you." The last words seemed to punch through her drunken haze, frowning at me before stomping out. The music was turned down to the point I could hear the tinny sound of the ping pong ball bouncing before Donna reappeared, tossing me a Mountain Dew.

"Could you try and not be a bitch?" Snapping the can out of the air, I cracked it open and instantly felt better at tasting the fake sweetness. Sighing, I followed her out to the living room and was instantly ignored as Donna went to the kitchen, getting tossed the ball for a shot. Leaning against a wall, as the couch was occupied by drunken girls in deep conversation, I found the experience tolerable without the music fucking my head.

Those playing beer pong game cheered or yelled at the result demanded, Donna spilling yet more beer down her front. At the rate she was going, it was a toss up if she had drank or was wearing more beer. I took another sip of caffeine, actually not hating being at a party for once when the front door opened and everything goes crazy from here.

Another sports scholarship stumbled in, this one a guy and he barely caught his balance before going face first into the floor. Standing upright with a shit eating grin, the door was closed behind him as the party examined this jackass. He was tall, broad in the shoulders and just about looked smart enough to know how to use a condom.

"Becky!" One of the girls hopped up from the couch and embraced him, the both of them managing a sloppy kiss that made a few of the girls giggle. The sports scholarship guy starting talking loudly soon as they broke apart, keeping one of his arms around Becky's waist and swiping a red plastic cup that seemed as essential to the college experience as overpriced, useless books in his other. He asked where the music was as I tuned him out, noticing someone else had followed him in.

Dressed in a baggy hoodie and jeans, this new person had successfully faded into the background, sidling away from the door without raising his eyes, the sports scholarship the center of attention. However, his shield, the sports scholarship was magnetically pulled to the beer pong table, leaving him exposed. The music got turned back up to brain rattling levels, someone mumbling incoherently into a microphone but it didn't distract me for once.

It took a second for me to conclude it was probably a guy and that made me even more curious. When he finally looked up, I was able to see more. His face was soft, not like the pretty boys with high cheek bones and nice lips that were always, without fail, stuck up assholes but leaning more towards cute. Girly. Him being short added to that and nearly drowning in his clothing created the illusion he was younger and didn't belong on a college campus. He did look completely out of his element though.

Leaving the wall without thinking, I nabbed another Dew off the kitchen counter and walked over, him watching me approach with trepidation. I silently offered the can and he took it, looking me over as I tried to do the same to him but was foiled by his clothing. Meanwhile, he was indulging in a nice, long stare that my low cut shirt provided. He visibly jumped after realizing how long he had been looking and busied himself with opening the can, turning away from me.

"I take it your here against your will too?" I asked, hoping he would respond and not shut me out, as I was curious and he really was cute... From what I could see of him. Which was only his face, framed by ear length dark hair that needed to be brushed. He took a sip before speaking, clearly still embarrassed.

"Is it that obvious?" I snorted and he gave a slight grin, encouraging me to keep going.

"Yep, takes one to know one. AND I FUCKING LIVE HERE!" My shout was mostly drowned out by the 'music' but the girls on the couch gave me flat stares that made me feel unwelcome in my own dorm. "You wanna go somewhere quieter?"

"What, outside? It's cold." He fidgeted, clearly not thrilled with the idea and I shook my head.

"No, fuck that!" Gesturing for him to follow me, I walked across the living room to the stubby hallway where my bedroom was. Opening the door for him, I only then noticed how much of a mess my room was but he followed me in, timidly looking around as the muted the music by shutting the door. "Sorry for the wreck."

"It's fine." Away from the insult to civilization that had been blaring out of the speakers, I was able to hear his voice, soft and inoffensive. "So much quieter."

"Take a seat!" I walked over to my bed and sat where I had been before Donna pulled me out into the party, which I was now thankful for. The stranger sat in my computer chair, looking around while taking another drink. This was the first time I'd had a guy over since college and it wasn't what I'd figured it would be. But still nice. "So, you in a grunge band or something?" That blurted out and I nearly choked, desperately not wanting to offend the only interesting person I'd met at a party. Instead of outrage, he chuckled, shifting in the chair.

"I wish. I tried to learn guitar but didn't get it. Haven't tried drums yet so there's always that. And bass, never too late to grow up and be Lemmy..." Taking a sip, he sat there lost in thought about music, a content cute grin on his face.

As if on cue, the door flew open, letting the ghoulish, never ending mumble back in as the sports scholarship dude looked around with frantic, bloodshot eyes.

"Holy shit! Jamie's talkin' to a girl!" Nearly screaming, he dug around in a pocket before throwing something at his 'friend', then gave an enthusiastic double thumbs up out of an 80's movie and slammed the door shut, leaving me deaf and confused. Blinking, face burning, he plucked the projectile out of his lap and held it up. It was a wrapped condom and he dropped it before covering his red face. I came up blank but Jamie, me learning his name the only good thing to come out of that intrusion, spoke up.

"Kill me, please and thank you." He removed his hands to take a drink but was looking anywhere but at me, face still crimson.

"And leave me here by myself? Notta chance." Jamie gave a wan smile and stretched, giving a groan that did not sound satisfied and grabbed hold of the armrest. "That didn't sound good.

Are... you okay?"

"No. Sure. I'm fine!" The last was said through gritted teeth as the can protested, crumpling in his hand before he caught himself. "Just fine."

"You don't sound fine. What's up?" Grunting, Jamie slumped before shooting back upright, resisting the urge to scream by the expression on his face. "Are you having a fucking heart attack?Come on, talk to me!"

"I... I just met you." I blinked, then nodded. He was absolutely right.

"Look, Jamie, right? I can't sleep with that shit going on and Dude Bro is your ride?" Sullen, he nodded, not very happy with anything by the looks of it. "So we're stuck here, together. Unless you wanna go back out there?" Shaking his head, Jamie got to his feet and began to pace. He looked at the open closet, colored and turned away, face lost in thought.

"I can't." Said not to me but himself, he winced and grabbed at the front of his shirt. "I can't!" I started running the odds of him trying to murder me or offering to sell me meth and while I'm not great at math, they were pretty good.

"Promise me you won't tell. Anyone." I nodded, not sure what exactly I was agreeing to and hoping it wasn't illegal. "I need help with something and I don't have anyone else to ask." He was pleading now and I was starting to get freaked out.

Blinking, on the verge of tears, Jamie pulled off his hoodie and stood there in an equally baggy T shirt, appearing lost and confused. Yet he slowly removed that and stood there, leaving me speechless.

Boobs. Jamie had boobs and there weren't what usually came to mind when it came to guys having boobs. I could have easily thought I was looking at a girl if I hadn't known it was Jamie. He was wearing a worn out, busted black camisole, the straps loose and color faded but holy shit, they were real and looked like they'd be quite a handful.

Things started to click: No wonder he wore the grungy, loose clothes. And being here was a chance to be discovered, with drunks not having a good grasp of personal space.

"Wow. Holy shit." I got up without thinking and Jamie watched with large, vulnerable eyes. He was so fragile looking and while it was hard to think while watching his chest rise and fall, I walked to the door and locked it. At first he took a step back, as if I was going to attack him. "So no one can get in, like your idiot friend." Nodding, Jamie relaxed maybe an a fraction of an inch. I had so many questions but was mostly in awe.

"So um, the past few days there's been this itchy, burning feeling that's driving me insane!" He was in obvious discomfort and desperate, which got me focused. Kinda.

"Is that doing anything for you?" I pointed at the camisole and he shrugged. That caused interesting things to happen around his chest region, along with him wincing.

"I guess? I put it on when I go out." Well, he had the right idea at least.

"Does it work though?" Muttering, Jamie offered up no other answer, not giving me much to go on. "Do you have any bras? Cause that thing looks done." Jerking back to attention, color flaring in his cheeks, he vigorously shook his head. In a what might have been a divine flash of insight, I instantly knew what his issue was and had to hold back a hysterical bout of laughter.

"Chaffing. It's chaffing your tits." Blushing harder still, he opened his mouth to protest but paused, looking down his front at the loosely hanging 'support'. Meanwhile, the phrase 'blushing bride' popped into my head and the image of Jamie in a wedding dress was maddening, making heat bloom in my stomach. He was slim, not very broad in the shoulders and would look good in a dress. At least a bridal gown might give him more support than what he had on.

"You need something snugger to keep it together." I nearly said 'your girls together' and that probably wouldn't have ended well. "Didn't your mom ever help you out with this?" Retaking his seat, Jamie cast his gaze to the floor and spoke.

"My parents divorced when I was little and I ended up with my Dad. When puberty hit, these showed up and he wanted nothing to do with me after. Every year at the start of school one of these would be on the bed. And that's it." I sat there, having heard the story but not comprehending it.

"So, boobs show up and your dad just... What? Checked out?" A sigh was my only answer and he looked up, hand going to his chest involuntarily, hissing in pain. As much as I wanted to see him topless, he needed helping considering his parents had failed. "Okay, I'm fixing this." Jumping up, I went to the blasted ruin of my closet and started digging.

"Do you have back pain by the time you go to bed?" Now that I was digging, thoughts of Jamie not in a wedding dress but in the shirts and jeans I was tossing aside latched into my head and that nearly made me miss his response.

"I guess but that's just bad posture?" His words faltered some when I sighed, brushing hair out of my face before returning to my search.

"Yeah, okay, but if boobs are big enough and not supported, you get bonus back pain! It's what a bra is made for. Besides, if you tried to run in that thing you'd bounce all over the place. And then die screaming from chaffing." A smothered laugh was his reply but it was what I wanted to hear. And I finally found what I was looking for.

"Here. Try this for now and see if it works." I pulled a nearly forgotten sports bra free, gray with lime green highlights cause colors made people run faster, I guess. Jamie flinched away from it, red enough he might be getting close to a critical meltdown. "What?"

"I can't. Wear that." He stared at the bra, then me, then the floor. Then his gaze flickered back to thing hanging from my fingers and away once more.

"And why not?" It was clear he had hang ups about wearing a bra but at his size, he needed one. And the idea of him wearing one of mine was alluring in ways I can't describe even now.

"Cause it's meant for-"

"For people with breasts, yes, your absolutely correct!" That answer obviously wasn't what he wanted to hear, his lips thinning into a pale line. "Jamie, it looks like your around my size and I'm a 36C. It's gonna get worse if you don't fix it now." His eyes widened at the thought and I tossed it over, seeing his mind made up in real time.

"Door's locked and my back's turned. Try it on." I went back to digging around in my closet but quietly so I heard the whisper of Jamie pulling off the camisole and discard it. It was creepy or stalkery to be so honed in but I couldn't help it, Jamie had wondered into my night and completely changed it. I bit my lower lip when the sound of synthetic fibers brushed against his skin and there appeared to be a brief struggle, barely able to hear it over the dim thumping of the music, glad he couldn't see how red I was this time.

"Um, okay?" Flipping around, I saw him standing there, wearing a confused expression and my bra. It wasn't very flattering but would do the job of keeping the jiggle under control. His midriff was exposed, mostly flat with an ever so slight flare of hips. But my gaze slid back up to his contained rack, appearing to fit a 36C very well.

"Does it fit right?" I asked, if only to try and stop staring but that didn't happen. He bounced on his toes and while there was movement in his chest area, it was subdued. As much as I wish it wasn't.

"Oh my God that's so much better." I heard the purist of relief in his voice and sniggered, Jamie giving me a look of gratitude that melted my heart. Snagging his shirt off the chair, he put it on and checked out how well the bra hid his assets.

"Check the corner." He looked at the cheap but tall mirror propped in the corner and examined from multiple angles. Try as he might, there was certainly something going on up top but the hoodie fixed that. Mostly.

"Still sore but I don't want to scream every time I move." Flopping down in the chair, he closed his eyes and took a deep breath, me noticing his boobs even under two layers. Opening his eyes, he smiled, raising a hand to his chest. "You weren't kidding."

"I told you!" I retook my seat, disappointed he had redressed so quickly but understood why. "And that's the most basic model, there's so much more." Shaking his head, another blush taking over his face, I dropped the topic but enjoyed his reaction to the idea.

"Thank you." The quiet, sincere words made the heat boil back up, a flash of him without a shirt on invading my mind. "Your the first person I've shown in... Forever, I think. And you didn't laugh."

"Why would I laugh? They're boobs and should be taken care of." I didn't mention the idea of Jamie in a nice bra was threatening to soak through my jeans and probably make me spontaneously combust.. "And this has been the best party I've been at. Got to help someone and some asshole isn't hitting on me." Jamie grinned, opening his mouth to say something but he noticed the camisole laying on the foot of my bed and his mood instantly soured.

"I'll throw it away later. It's done." Grabbing and chucking it out of sight under my bed, I got the conversation rolling again. "Now, what were you saying?"

"Can't remember. Just trying to figure out how I'm going to repay you for this." Another deep breath and a slow, honest smile that made me sit back and cross my legs lest I jump him right now.

"How about giving me your number?" He was speechless for a minute but rattled off a series of numbers that I punched into my phone, instantly sending him a text.

"I uh, don't know your name." That's right, I only knew his name thanks to his stupid friend barging in.

"Gen. And your Jamie, glad we could finally meet." He smirked and I darkened my phone, setting it aside. And we talked for what felt like hours as the wall separating us from the party was thumped a few times, laughter sometimes bleeding through but that time was ours and ours alone.

Only when the door was slammed against was it clear that this quiet time was over.

"Jamie! Stop fuckin', we gotta go!" Of course it would be his stupid friend. I got up and unlocked the door, stepping aside as it opened and he fell over this time. Crawling to an upright position, he was laughing too hard to say anything coherent and crumpled back into a heap.

"I hope your fuckin' driving." Jamie looked at the person laughing to the point of tears about nothing and sighed.

"Probably should." He rose out of the chair and joined me by his friend, who had curled into a ball and was clutching his stomach, lost in the throes of hysteria. "Tom, I at least need the keys or we can't leave." Gasping for air, this supposed Tom reached into a pocket pulled out another condom, resulting in a fresh bout of laughter.

"Jesus Crispies." In the living room Donna was yelling over the music at another woman and they were all that remained. I marched out and shut the music off, Donna protesting but I ignored her. Returning to my room, I hesitated before looking at Jamie. "I ain't reaching down there." Somehow that didn't set Tom off again and he stood, swaying and squinting at Jamie as if he had never seen him before. For a terrifying instant, I thought Tom had magically noticed Jamie having boobs and call him out but he instead said: "Didja get laid or not?"

"Sex isn't everything." Tom steadied himself against the door frame, nearly smacking me in the process, and tried to think. I say try cause he reached no conclusion, instead producing a set of keys and shaking his head.

"Come on, we gotta get home!" A sickeningly wet burp came out of Tom and it reeked of beer, making my eyes water and Jamie recoil. I put a hand on his meaty back and pushed him out, waving away the last of his fumes.

"You good?" Jamie gave a tender, beautiful smile and I wanted to take him in my arms and never let go. I did the first part however, pulling him in a hug and finding we were about the same height. That meant his boobs were pressing into mine and that was something I didn't know I wanted until now.

Joshana
Joshana
272 Followers
12