Finding the Perfect Fit Pt. 02

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Gen provides, Jamie explores.
3k words
4.54
18.5k
16

Part 2 of the 25 part series

Updated 06/09/2023
Created 09/14/2019
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Joshana
Joshana
272 Followers

This story is a slow burn serial that is updated weekly. Jamie is a withdrawn college boy with a secret under his shirt while Gen gives no fucks except about Jamie, who she met at a terrible college party with shitty music and bad beer. You know the kind.

*****

God, I hate being the stereotype of 'girl who's bad at math' but geometry just breaks my brain. I'm never going to do any sort of construction or carpentry, we already have a Bob Vila, the world's good! Holy shit, how do I remember that guy's name?! My Mom used to watch those home improvement shows when I was younger and I'd usually pass out to them. 'This Old House' should be a doctor recommended sleep aid.

...What the fuck am I writing? I lay down to type about Jamie and this comes out?! Anyway, he he's all the way on the other side of campus, which sucks with how cold it is but one could, in theory, walk over there. Granted, he's stuck in a room with Tom and that made me curious. I asked him how he kept his chest secret from his roommate and his reply was: "Not being there when he is." All I could do was laugh.

Between classes and both of us working part time jobs, finding time to hang out isn't easy but Saturday seems to be free for the both of us and it's only Wednesday now! I want, so badly to see Jamie in something nice but there's the issue if he wants to. Gotta figure that out now!

Next Another Day

Saturday finally came and I went on a whirlwind cleaning session, finding the camisole Jamie's inept father gave him and tossed that in the trash, then hauled that shit to the dumpster. With that thing gone, I dug around for some bras and threw them on the computer chair where he had sat last time.

With that done, I went out into the cold and hoped my heater would kick on quicker. Sure, I could walk but fuck that, too cold. Driving to the nearby pizza place, I got inside where it was warm and smelled of tomato sauce and carbs. Jamie was sitting on a bench across from the register, bundled in a coat that didn't betray his secret.

I sat down beside him, his crooked smile coming back, along with a light glow in his cheeks. Christ he was adorable!

"How's it going?" I asked, not sure what else to say. Seeing him again was making my heart flutter and stomach go nuts. Or maybe that was the promise of pizza? No telling.

"Better." Knowing why he was better, I couldn't help but giggle and he bit his lower lip to keep from doing the same but it didn't matter. Neither of us could help it as we burst out laughing, so many reasons why and I couldn't say a damn one. He fell over onto me and I wrapped an arm around his shoulder, trying to keep us from spilling onto the floor as we lost our shit. Rhyme and reason died there for about a minute and it was fine, Jamie was there with me.

Only when the pizza was ready did reality reassert itself and we had to be adults again. I stood and helped Jamie up, still smiling from the bout of hysterics we had been afflicted with. The guy behind the counter wasn't amused and that only made everything funnier.

Pizza in hand, we stepped back out into the cold and got into my car, that spontaneous laughter lurking about us still.

"Why were we laughing? That wasn't funny!" Jamie didn't even get the words out before howling with laughter as I joined in against my will. Clutching the steering wheel, I took deep breaths until I could see again.

"Holy shit, okay, that's enough. I gotta drive." And, of course, that set off another round and we were stuck, unable to even shift out of park as we wound down. Finally, I was able to drive without endangering everyone and everything else on the road, stomach hurting from the rampant laughter.

Thankfully, we got to my place without incident and passed Donna hanging out in the living room. Somehow, I'd completely forgotten about her. She looked up from her laptop and removed her earbuds, a dawning familiarity come over her face.

"Hey, you were at the party right? Came with that jackass?" I snorted, glad to hear that I wasn't the only person to think about Tom. Jamie nodded, staying behind me. "You made a friend Genna, good job." I flipped her the bird and she returned her attention to the screen as we went to my room and I engaged the lock.

Jamie was standing by the desk, looking at the chair with an expression I couldn't quite read. He didn't want to stare but was still holding the pizza and had nowhere else to go.

"Sorry, I was cleaning." Almost a true statement. I grabbed the bras and set them on the desk, slipping my shoes off as I sat on my bed and Jamie took his now clean seat. There wasn't much talking as we began to eat, me trying to figure out how to broach the topic of him getting into a better bra and then maybe into my pants.

Wiping his mouth and hands with a napkin, Jamie cleared his throat and a wave of red took over his face as he got his thoughts in order, then spoke.

"I did some research after last time and talked to my doctor. Officially, what I have is gynecomastia, which is breast tissue in guys. My doctor had told my dad I should be wearing some support but I guess he didn't listen. When I talked to her, she was surprised that I had only now started wearing a- a bra." Face burning red and those last few words came out haltingly but Jamie managed it. "I looked and there's other guys who have to deal with this sort of thing and it seems there's two choices. Either get them removed," I winced at the idea but he didn't seem to notice, "Or keeping them, which involves proper care."

"That's more research that I've done for anything, ever." Sad but true.

"I've always been ashamed, that I'd done something wrong and anything like this only made it worse." He poked a bra sitting beside him, face still blazing.

"That's bullshit!" Instantly angry, I rolled out of bed to stand before Jamie. "Look, your living with some medical condition and it happens to be boobs. If someone thinks less of you cause of it, fuck em! Do whatcha gotta do and stop worrying about your dad or whoever else! It's your fucking life, not theirs, so live it!" I threw my arms in the air, panting, looking down at an awestruck Jamie with shimmering eyes and my heart melted seeing him on the verge of tears.

"You a motivational speaker?" He asked with a slightly foggy voice. I offered a hand and he took it, me pulling him up into a hug.

"Nah, I swear too fucking much." Jamie snickered, wrapped up in my arms and I became aware of his breasts against mine again. He might have realize that too cause he broke away from the warm embrace, face red once more. Or still. Jamie removed his other layer and looked off to the side as he spoke.

"If your willing to help me out with uh, donations, I'll take it." Not meeting my eyes, he clasped his hands behind his back and was the vision of innocence. That I hopefully was going to defile at some point. "This fits and stopped the chaffing but I only have one. Um, couldn't hurt to have more, right?" I had to keep from breaking down into more laughter but nodded, knowing this is how it began. One led to three lead to holy shit, my closet is flooded send help.

"Go for it! Pick whichever one you want!" Jamie turned back to my desk and picked a peach one, looking at it curiously. "That's a t-shirt bra. It's got fitted cups and doesn't give you the uniboob look." Looking down, then at the mirror, Jamie's face was one of utter confusion. "Oh come on, you know what I'm talking about! Compare you and me." I inhaled, puffing out my chest and that got his attention real quick.

"See?" My shirt wasn't that low cut but was sort of tight and yes, Jamie was getting the point. "Best part is it isn't too bulky and is nice for the average day." Shaking his head, he looked at what was in his hands as if he had never seen it's like before. Which might have been true actually.

He nodded and I went over to my closet, once more busying myself by looking for anything as shirt, then sports bra were removed and then the straps flapping about, followed by a frustrated sigh.

"How are you suppose to latch this? I can't reach." I restrained a giggle as I'd had the same problem starting off. And here was someone who should have been wearing them all along dealing with the same thing. Jesus wept.

"Latch it on the side, then twist it around and pull the straps up. Make sure it isn't too tight and that your fitting in the cups right." I wanted to help him but he had to learn. And this thrill of waiting to see him in it was intoxicating. Sure, a t-shirt bra was tame but I had others that gave lift, shaped and I went looking for them feverishly. That was when I realized I might be getting a little too invested in this whole thing. Was this some sort of weird fetish? There wasn't any more time to dwell on it as Jamie announced he had it.

With a light heat fluttering in my stomach, I flipped around and saw Jamie standing there in another of my bras. Even in something as mundane as a T-shirt bra showed how much volume Jamie had, as he filled it quite well. I walked over and checked the fit, seeing the band was just right on the middle latch.

"Does it fit here?" I grabbed my own boobs, partially to keep from grabbing his and to see Jamie's shock, of which he provided.

"Uh,yeah?" I could have checked but that would have invaded his personal space to hell and back. I grabbed his shirt and handed it over, him getting the idea and slipping it on. Checking the mirror, you could tell there was something happening in the chest region. However, the hoodie, which could double as a circus tent, solved that problem. Bouncing on his toes, he looked confused.

"Wow, that's weird." All I could do was nod, biting my cheek to keep from laughing. Still, he was in a real bra and had done so on his own free will. It was more than I could have hoped for and yet I wanted so much more. "This is so different from the others."

"Well, most bras tend to shape along with supporting. Sports bra just hold it together, unless you get an expensive one to show off at the gym" Removing his hoodie again, he inquired back at the desk and picked out another one. This one was black and made nearly completely from nylon or something else soft, with equally soft cups. It was comfy and the ultimate in 'fuck everything' moods that my period usually left me in. "Go for it!"

Giving him the privacy to change, I returned to the closet that I'd thrown a bunch of clothes in during the first few days in college and mostly forgot about them. Now I had a reason to care about all I brought with me!

"Why do you have so many of these?" He asked, having no idea that certain times called for lift, cleavage or comfort. By the way he dressed, comfort was never an issue for him, the lucky bastard. I had to pull my attention away from a dress from high school I'd completely forgotten about. Not sure why it was here but the ideas it was giving me fought tooth and nail with 'Jamie in a push up bra' and my brain was going to explode at this rate.

"Most women have a few and I splurged with my graduation money. So I have some to spare." Those were stashed away in the dresser and, God willing, would come later.

"I still feel kinda bad just taking them." A bit more movement and then a pleased 'huh'. "This is nice."

Doing an army perfect about face I will never be able to replicate, Jamie was looking happily down. Again, the bra was filled and slightly showed the swells of his pale cleavage, stark against the black of the bra. Sure, it was tame like before but Jamie was enjoying this and so was I.

"It's there but more comfortable than the other one." Slipping his shirt back on, he referred back to the mirror and patted the rounded shape that was more pronounced, frowning. "That isn't so good."

"Your stacked, what do you expect?" My mouth had moved faster than my brain and I winced, realizing what I had said and to who. Sitting on the bed, silent, Jamie picked up the peach T-shirt bra he had on a few minutes ago and put his hand in one of the cups.

"Really? I've seen bigger." He didn't sound annoyed or sad, just curious. Picking my words carefully, as I didn't want to insult him and disrupt this, I sat on the bed beside him.

"Sure but it depends on the body type too. There's those tiny, petite girls and your tits on them would look huge. Your fitting my bras and I'm around a 36C, which I think is above average? I'd say most of the girls in college are around A to B, meaning your bigger than they are unless they've got a bigger band size but you don't need to worry about that." Sister sizes weren't on the agenda, not yet.

Any response was halted by his phone going off, Jamie frowning at what was displayed on screen. Still, he answered it and I sighed at who it was.

"Tom... Tom! Stop freaking out! I'll be there! If you'd said something soon this wouldn't be an issue! Just, I'll be there!" Ending the call, he leaned back with an exasperated sigh.

"You want a ride?" He nodded, noticing he was still holding a bra and flushed, working on driving me insane via horniness. "Grab your pizza and let's go."

"What do I do with this?" I took the bra he offered and folded it, wrapping the straps and tucking it away in one of his coat pockets.

"There! Just take your coat off when you get inside and hide em so your fucking idiot of a roommate doesn't find them." Jamie nodded, a smile playing over his lips and he gave me an awkward one arms hug, the pizza box in the other.

"Thanks for this. It means so much." I returned his embrace, our boobs finding each other again and when he broke away, his color was high and gaze downward. "Better get going." He walked to the door and paused, not moving before undoing the lock and opening it. I promised the next time I saw Tom to kick him square in the balls, cause he had fucked up what had been a good thing.

Still, we got going and made awkward small talk until I dropped him off. I drove back and Donna watched me pass, not saying anything as I went to my room and flopped down on the bed and started writing this. So, to recap, what have I learned today? That Jamie is eager to try new things, he might be the cutest person ever and... He left the sports bra here. It's on the floor by my desk. Well, guess he's wearing a real bra for the time being!

Shit, I saw him in a bra and didn't return the favor. Will have to fix that next time.

Another, Different Day

Got a text from Jamie today: "Had to run to class and it was nice to not be bouncing all over the place." That was good for a laugh but it made me curious as well.

"Which one are you wearing?" It took a bit for him to respond but I got a picture in return, his hoodie and shirt pushed aside to expose a black strap of the comfy bra. "Told ya it's nice!"

"I think I forgot the other one at your place." I told me he indeed had. That did remind me of what I'd written a few days previous. I was in that dead zone between classes and work and Jamie was a welcome distraction. Picking the sports bra off my desk, I put it on and snapped a picture, sending it over.

"I saw you in one so you get me and mine. Nice and fair." Taking that one off, I replaced it with one had I had been wearing today, a sky blue one with some lace on the cups and straps. I got a picture of that and shipped it along, finding my work shirt and getting ready.

"Why didn't we do this when we were hanging out, in person?" All I could do was laugh. I told him replies would take a little longer, was going to be a work and stepped in the living room.

"Hey, how'd it going with that guy from the other night?" Right, Donna knew about Jamie. It wasn't a big deal but with his secret, it made me uneasy to have someone around when he might be expanding his horizons.

"Not bad, mostly just hung out." A raised eyebrow was her only response and I got going, thinking about what this money could be going towards now. I did my job, checked the schedule and then came back here. Thinking all the while.

Joshana
Joshana
272 Followers
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SissyCrissy6245SissyCrissy6245almost 3 years ago

Lovely thread...and amazed this is your first "thread". This long-time TV/CD just can't resist her dainty, feminine frillies...especially my pretty, lace VS/Maidenform underwire Brassiers (36A). Does tofu really help promote gynecomastia? I've heard/read that Lavender Oil helps sometimes too. ;-)....thx for sharing this "tail"

TranylvrTranylvrover 4 years ago
Great story

Can't wait for the next chapter! Love the characters!

JoshanaJoshanaover 4 years agoAuthor

The third part of this story, which has some action!, was uploaded later than usual and seems to be processing quite slowly. It's still coming and is a decent chunk coming in at 9 pages but is out of my hands for the time being.

AnonymousAnonymousover 4 years ago
Enjoying the story

I won’t be like so many here and tell you which direction it should take, but I would love to see longer chapters.

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