Finding the Perfect Fit Pt. 03

An Awesome Day

It took too long for Jamie and I to hang out again but we kept talking the whole time, me working when I could. If I asked what he was wearing, I'd get a picture of a bra strap peeking out from under a shirt, the black comfy one proving to be the most popular. But the peach T-shirt bra got some use too, more often during the weekend.

"It's so much better but I wish I'd wasn't paranoid about people noticing all the time." I sympathized but wasn't sure how to fix that, aside from following him around with a baseball bat and breaking kneecaps if someone even hinted at pointing out he was breaking a bra. "Just takes some getting used to." That part was true but I was pleased to see him taking this whole thing in stride.

Yesterday I get this: "I got a few hours tonight, do you?" I instantly confirmed I did and began one of the most annoying tasks of all: Waiting, as I was stuck in class. Being giddy only made time pass slower but thinking of anything else was nigh impossible. Thinking about Jamie in something nice made me want to start grinding against the nearest person, who happened to be a pretty woman with long black hair with lots of eyeliner. That only made me curious about Jamie's thoughts on make up and I ended up crossing my legs to remove the temptation of trying to get off in class. Instead, I did everything in my power to pay attention to the lecture.

I took some notes and actually tried to comprehend the lesson, the prospect of taking a science test not so bad for once. That was the last class of the day and while I had homework, it could get fucked, this was my time now. It was then Jamie sent confirmation that he was able to come over tonight and it was so close now.

I still had time and used it. Checking my dresser, I dug out one of the push up bras and paired it with a shirt with a plunging neckline. A tighter pair of jeans that took some wiggling to get into and some make up, I was ready. Sure, my hair needed a trim and concealer was running low but not bad.

Sure, this wasn't cold weather clothing but fuck it, Jamie was coming back here and I didn't need to get out of my car. A bra rescued from the closet was tossed over the back of my computer chair, covered in black lace and quintessential. Another one, sister to the one I was wearing, was placed just so on my dresser, in easy sight.

Maybe this was going too far. Jamie wasn't a plaything, dancing to my whims, he was a person! But if I played fair, listened, and matched anything he did, was that still manipulation? Now doubt was eating into what had been promising to be a good time but I still got moving.

Donna was in her usual place with ear buds in, giving a wave as I hurried out, getting punched in the face by the cold. I needed to figure this now. I got my car started and turned the radio on to classic rock. So, chances were good I had a fetish for this sort of thing. Or maybe just Jamie. So, why hadn't I researched it, done anything at all to see if anyone else shared this idea? I mean, with all this fucktarded bullshit about the world being flat flying around, did a woman wanting a guy with boobs to dress up pretty wasn't that weird, right?

It wasn't anywhere near normal and while I was fine with that, I needed to make sure Jamie was too. Pulling in the parking lot of his place, I texted I was here and he replied that he would be a minute. Good. Taking this time, I opened my phone's browser and tried to figure out what exactly to search. Hoping that whatever company grabbed this search data choked on it, I tapped out 'I like guys with boobs' and hit Search, hoping that didn't put me on some sort of watch list. The results weren't what I'd hoped or feared, mostly being articles about guys talking about touching boobs for the first time, which was infuriating to both me and Cassandra, who had boasted basically none. And here were a bunch of guys saying 'yeah, it's great, I love it.'

Deleting that, I slammed in 'I like girly guys' and that got me closer to what I was after. A few threads of girls saying they like feminine guys was all I was able to skim before my passenger door opened and my heart nearly exploded.

"Man it's cold." Jamie buckled up and looked over, noticing I was fumbling with my phone and freaked out. "What, did I scare you?"

"Yes, you're the face of terror Jamie." Shoving my phone in a pocket, I got us moving. My heart running at an elevated rate. "Is Tom going to be calling tonight?" At that, Jamie sighed, leaning back in the seat. With the belt running over his chest, I could tell what was there and that wasn't helping my mental state at all.

"No, his dad is getting him a tutor, thank God. No matter how much the basketball teams needs him, Tom's never going to be the letter writing sort." I personally found it shocking he knew the difference between beer and bleach, given what I'd seen of him. "So, what are we doing tonight?" My heart either skipped a beat or was priming to explode.

"I-I... Uhh." I just needed to ask if he was alright with me using him to play dress up with. And that I was getting off on just the idea and seeing him in my clothing threw switches in my brain that threatened critical meltdown. But if Jamie said no, this might be the end of my involvement with him learning about boobs and the such. Yet leading him along was wrong and I couldn't do that!

Gripping the steering wheel hard enough my knuckles went white, I pulled into the nearly empty lot of the book store and parked, failing to get my wits about me. It wasn't late but close enough, most of the lights in the buildings dark and forlorn in the cold. Taking the wheel in a death grip, I took a deep breath that did nothing for my nerves and spoke.

"Jamie, I've never met anyone like you before and I'm not just talking about the boobs. Though that helps, not gonna lie. I wanna see what the rest of you looks like and if your willing to put on pretty things cause that idea is driving me fucking insane. And I'll be fair. Do something for me, I'll do it for you. That's my offer." My car idled as I stared at a crack in the plastic of the steering wheel, deeper and darker than it should have been for such a small thing. "I just said that out loud, ohmygawd." And then I buried my face in my hands as my stomach and brain ate themselves out of sheer embarrassment.

"Well, that's a lot to take in." He didn't sound disgusted or annoyed but... Bemused? "I'm sort of disappointed there wasn't a 'that's what she said' joke. Or maybe I've been around Tom too long." I spoke through my hands without thinking, as my brain was eaten by my brain.

"Depends, how much ya got?" And then I started to laugh at the stupidity of it all, lest of all my lame excuse for a joke.

"Well, you want to find out, right?" That got me to abandon the safety of my created dark and look at Jamie, not daring to hope I'd heard him correctly. "Gen, you've been nothing but nice to me. You taught be about bras and gave me a few, listen when I bitch about mundane shit and I think you might be the best friend I have, outside the internet. I've never even kissed a girl before and you come out of nowhere, offering all this and I'm left wondering what I did to deserve you."

That thought took some time to punch through my psyche but once I'd grabbed hold of it good and tight, I acted. Undoing my seat belt, I leaned over the center console and planted a kiss on his lips, lingering there. Slowly, he returned the kiss, his slightly chapped lips pressing to mine. My tongue came out, running over his lower lip before he broke it off, panting. I returned to my seat, needing to catch my breath as well.

"Wow." I nodded in agreement, knowing I could do so much more and better once we were in the freedom of my room. With that thought, I started driving again. Jamie took a bit of time and spoke as we waited at a red light. "So, is that what we're doing now?"

"Long as your comfortable with it. Well, that and me seeing what I can get away with dressing you up in." That I was saying this out loud was insanity but someone was going along with it so was it really madness? Granted, that's how cults work but I ignored that.

"I mean, if you want to..." I looked away from the road for an instant, there was fucking no one out in this cold, and saw that growing familiar blush spread over his face, bringing about that insistent idea of him in a wedding dress as a blushing bride and fuuuuck.

"Yes! God yes!" A pause of me realizing I'd been shouting. "Only if your cool with it." That sounded really lame after yelling how much I wanted him to go along with this.

"I never thought I'd be wearing a bra but I've been doing it for over a week now. And it's helped! Still getting used to it but I didn't blow up when I put it on." I briefly thought about telling him I came close to blowing up in a different way when I saw him wearing it. "I mean, why not try it out?" His face was blazing now and he might have been talking to himself as much as me but I shut up and listened. "What do I have to lose by saying yes? What do I miss by saying no? How does the world change in the end if I do this?"

"You sure your not a philosophy major? Cause that might made you hotter." He burst out in laughter and I joined in, slightly shaky. It was bordering on surreal and I wasn't sure how to respond to this turn of events.

"Nah. I've been doing some looking online and some people who have gynecomastia experiment with this sort of thing, clothes and the such. I agree with the idea that it really isn't that big of a deal. Plus, if it means we get to spend... quality time together, I'm down." I started laughing nearly hysterically then, thankfully close to home and I parked without wrecking, needing a minute to calm down. Once I could breathe again, Jamie waiting with that crooked grin affixed to his face, we got going. Donna was in her usual spot in the living room, still on her computer, giving a wave to Jamie and me a knowing grin along with a raised eyebrow.

Leaving her behind, I closed the door behind me and couldn't help but look at Jamie with a hunger that had been building for days now. Chucking my coat off, Jamie turned from examining at the push up bra to me, wearing such a thing.

"Oh." It was the most polite way of saying 'Fuck yeah boobs!' I'd ever heard. "That's the bra helping to do that, right?" I nodded, unable to hide the smile that he'd picked up on it. He was blushing but appeared thoughtful once more.

"You uh, ready to get going?" I was a bit shakier than normal, still working out this was real.

"Sure." He flushed with red but walked to the computer chair, having spotted the black lacy bra there. "I'm guessing you want me to try this one?" My face grew warm this time and I nodded, my voice deciding now was the best time to bail on me. Taking his hoodie off, the shirt followed suit and Jamie was in the T-shirt bra as I turned back to the safety of my closet.

"I wasn't sure if you were going to watch." I nearly choked at that, how fast this was all moving.

"Jamie, I do so damn bad! But I wanna wait, to draw it out as long as possible cause I enjoy this! Torturing myself! YEAH!" Raising my fists, I gave a strangled groan that was the only way to express the pleasure I was deriving from this pain. Jamie's boobs were like Pandora's Box, once they were out, I'm not sure there was any going back in. Probably cause I wouldn't be able to get my hands or mouth off them.

"This is... Weird. And there's padding?" I choked back laughter at that, collapsing against the wall for support. Would he ever look at a rack the same way again after this?

"You sweet, innocent soul." Jamie announced he was ready and I saw. More of his breasts were visible than before, practically burning against the black of the lace. They were nicely rounded and there were swells from where they rose from his chest. "It's kinda tight."

"That's what she said." I said absently as I went to check the fit and fiddled with the straps some. "Okay, looks good and I'm going to go insane at this rate." He gave that crooked little smile and checked the mirror, pausing. The expression on his face was complex, something unkind struggling against an odd sort of wonder.

"You okay?" I was in the reflection and couldn't tell if I belonged or was barging into his discovery.

"Is it narcissistic to pop a boner at my own reflection?" He colored again, either from talking about erections or my giggles.

"If more guys had your rack, it'd be common." God knows if I had a dick it'd be tearing through my pants. And huge. The Incredible Hulk of penises. The In-cock-ible Chub...? "By the way, it's padded to made them look bigger and fuller, though your good there." Still looking at his reflection, he touched the lace on the front and a shiver quaked through him.

Either to steady himself or to just keep his hands occupied, Jamie's arms crossed over his chest and he took a deep breath. With his eyes shut and legs close together, Jamie might have been some forgotten object of reverence in this pose, peaceful and alluring. Dark brown hair brushed against his rounded jaw as he bowed his head, as if in prayer. Baggy jeans paired with his nearly nude torso gave him a bizarre look that easily could have been some sort of modern day monk.

Witnessing this, I could say nothing. While he wasn't like that for long, I burned it into my memory, not reaching for my phone but securing it in my head. Only when his eyes opened and hands fell from his shoulders was the iconic status broken and Jamie the person returned.

"Sorry, just getting used to... Whatever this is." A sheepish grin crossed his lips and I laughed, seeing what I'd hoped for right there, in touching distance. Glancing at the mirror again, his eyes darted to my reflection and back to his. "Can, can I try one like yours?" Right on cue, a red flush bloomed over his face and it was the glory of a sunrise illuminating the horizon.

"Why?" The question escaped my mouth and I regretted it instantly. This was a good thing, a safe place for him to explore, to discover and that question could spell the end of it. But I wanted to know what was happening behind those blue-green eyes. And maybe find out if he was enjoying this as much as I was.

"I-I wanna see if it makes mine look like yours." Spoken in a small voice, he wouldn't meet my gaze as he said it.

"Well, your in luck cause it's gonna. Go ahead." Reaching behind me, I plucked what he requested from the dresser and tossed it over. As he gave it a squeeze with a perplexed expression, I went into my closet and clicked the light on. Keeping busy by looking through all sorts of clothes that was giving me too many ideas, I heard Jamie struggle as I did my damnedest to keep honest and not peek.

"Oh wow." I waited for another word of confirmation but Jamie had fallen quiet.

"Well?!" I couldn't keep impatience out of my voice as I pulled a shirt with a deep neckline like the one I was wearing off a hanger, black of course, befitting the gray bra and Jamie's own grungy fashion sensibilities.

"Uh, okay?" Leaving the tangle of hanging cloth behind, I forgot the shirt as Jamie was trying to stare at the mirror and me at the same time with wide, startled eyes. Glued to the view now on offer, my overloaded brain somehow remembered my promise and I took my shirt off. We looked as one in silence at the reflection, seeing twin sets of cleavage. Even though I knew it was the combined lies of padding and lift, it was gratifying to finally see what I'd been after since the first night of knowing him. And he looked damn good, his rack paler than mine and that seemed to be the only difference between us.

Christ, I was standing next to a guy who filled out one of my bras just as much as I did! His chest hitched as it rose, my eyes frantically trying to drink in everything at once: To the gentle slopes where the bra pushed his breasts together, creating that infinitely interesting 'Y' of cleavage, then where his skin met the lace of the cup, not overflowing it but rising forth with each breath. I couldn't believe it yet here he was, with me, locked in this surreal, beautiful moment.

"Told ya." We beheld the showing of killer boobage, helpless to do anything else. Here were what looked to be two almost topless girls in some guy's, or mine, whack-off material. And thinking of Jamie like that, as a girl, caused what few unfucked brain cells I had left to implode.

Running fingertips from where exposed breast met lacy bra, Jamie gave a little shiver and made an interesting noise that was a mix between a moan and a grunt. There was no need to ask as I saw the intrusion of another member to this scene, one who looked quite happy with current affairs.

Taking a few shaky steps away from where we had been rooted, he stood with his back to me, breathing hard. Jamie stood alone but only for an instant before I followed, my bare feet against the carpet loud in the nigh reverent hush. Vague intentions urged me to him and I acted on them, any higher thought obliterated by a feverish heat stoked by what I had seen.

"...hey." Almost a sigh, Jamie still jumped at that single, soft word. Another step and I was right behind him, seeing his slim back cut by the dark slash of my Victoria's Secret bra. Reaching up, I brushed his hair to one side, a light moan escaping him when my fingers grazed his neck. A baby step closer and my bust was brushing the band holding his enhanced cleavage in place. I closed what empty space remained between us, my breasts pressing against his back, hands slipping around his waist as I felt his warmth and jittery breathing.

I had my hands about him like guys in prom pictures do to their dates. That thought wedged itself into my brain with the previous ones like shards of glass on a hot summer day, unable to be ignored. While my head was gridlocked with too many unnameable desires, my body acted. Reenacting what I had done with Cassandra after a high school dance, I ran my hands up his form and drank in the slight curve of hip, feeling him quiver as I thought he would.

Where as Cass had been wearing a slinky dress, Jamie's body was bare but no less alluring. Up, over the smoothness his pale skin promised once freed from the protective over-sized shirts. And then Jamie's breath caught as I finally reached his secret and my prize.

With my hands resting on what was slowing rising and falling, I felt the lacy surface of a bra I'd never thought anyone besides me would wear. I gave the cups a squeeze, knowing he felt my touch even through the padding. Sliding my thumbs over the firm skin of his tits, I moaned at the audacity of this, of finally making it this far.

Kissing the back of his neck, I gave another, slightly rougher squeeze while pressing tighter to his back. A moan came from him, light and wavering as his back arced, pushing his butt into my crotch. Another vivid flash of memory, back to a different high school dance with girls in tight jeans grinding into guys.

A groan escaped from my lips as I struggled to comprehend what was happening and the role I was playing in it. Jamie's butt was against me, the baggy pants seemingly hiding a surprising amount of cushion but that thought was consumed by the tempest raging in my skull. Operating on some lurking base desire that not even Cassandra had awakened, I slipped a hand in the bra for the real deal.

Jamie gasped, making what I now held quake, my shallow breathing stirring his hair. His breast filled my hand, my middle two fingers sinking slightly into softness with a hard nub between them. Giving that a slight tweak, I was rewarded with what could only be described as a squeak, Jamie's head leaning backwards, lips parted, eyes closed. Looking down his front, I glimpsed what I had pillaged the padded cup for and lower still, a tent that had been pitched and ignored this whole time.