Finding the Perfect Fit Pt. 05

Finally

I bolted awake Saturday morning, instantly knowing what I had to do. It was like Christmas morning when I was a kid, with endless potential dancing in the air and anything was possible. But it was on me now to make it happen. Rolling out of bed, I looked out the window and paused, seeing the light dusting of white over the campus grounds. Sure, it wasn't much but snow before Thanksgiving? Ugh. Didn't matter too much, as all the action was going down in here.

Putting on some music, I started cleaning. Up before eight on a weekend, what a time to be alive. I started by tearing my closet apart, tossing things into piles and actually using hangers for the fancier stuff that had been brought along for reasons lost to time.

Cramming the interesting things into the dirty clothes hamper, I carried it out to the kitchen laundry room combo. Dumping it into the washer, I got the soap in and started it, only noticing Donna passed out on the couch after it started making a racket. Oops. Why she never slept in her room I have no idea but I didn't have time to worry about that right now.

Walking back to my room, I made my bed for the first time in years, feeling childish but doing it anyway. Now came my dresser, picking through that and making another pile of interest. Checking the washer, it was done and I moved that load to the dryer, stuffing the washer once more. Somehow, Donna was sleeping through it. Good for her.

That done, I vacuumed for the first time since moving it. I should have done it sooner but hey, better late than never! That done, I checked my the make up supplies and found I had enough, as eyeliner was usually enough for me.

Second load in the washer was done and the dryer was close enough so I got it moved over, taking the toasty laundry and dumping it on my bed. Now I could shower and shave, enjoying the humid heat in the midst of winter. After I got out and dried my hair, I saw a message from Jamie waiting for me.

"You up?" I smirked, having been cleaning for two hours now. But he didn't need to know that.

"Sure, what's up?" I waited in the muggy fogscape for an answer and silently cackled when the answer came.

"When do you want to hang out?" Slipping into a pair of shorts and a ratty old shirt, I left my little sanctuary and crossed into my room.

"Soon as I get dressed, too cold to be topless." I dressed for the day in a clingy purple shirt with the usual tight jeans, adding eyeliner and eye shadow, lipstick and foundation. Brushing my hair out, it still needed a trim, I checked on the dryer and found Donna blearly looking in the fridge as if food was hiding away, just waiting to be discovered.

"Your boy toy coming over?" She had clearly noticed I was actually trying today.

"Don't call Jamie that." I reached past her for a can of caffeine, cracking it open and taking a drink as Donna shrugged.

"Whatever. I have practice so you two can have fun without bothering me." With a smug and knowing smile, Donna closed the fridge and wondered back to the couch. She was wrong but not too far off, at least hopefully. Taking the final batch of laundry, I dumped it as well onto the bed and spread it around, a riot of colors waiting for Jamie. Or me if he requested I join him.

Finding my coat, I sent Jamie as message that I was going to warm up my car and be on my way. Outside, the sun was shining but distant, the snow now a hard crust. I was so close now and just had to wait a few minutes! The question was if Jamie wanted to carry on with this or wouldn't be interested in the spread I had prepared for him. I'd respect that but be disappointed. Still, I was going to press on and see where this went, the roads somewhat clear, with two tracts of black against the white.

The campus on a Saturday before noon was mostly asleep or hung over, the cold keeping those awake inside. I drove carefully, not wanting to derail this day with a wreck. Soon as I pulled into the parking lot, I saw Jamie hurrying towards me. Popping the locks, I tried to still my racing heart as he opened the door and got in, setting a backpack on the floorboard.

I don't know what I expected after less than a week from when I last saw him but he looked the same. Round face above an over sized coat and jeans. His longer untamed hair was damp, having probably showered as I had. Still did me good to see him, heart getting warmed up for the day.

"It's fucking cold!" Jamie nearly shouted, palms open to the vents as I got us moving.

"Happens this time of year, every year." Getting flipped off for my wit, I grinned, glad to have him back. "So I gotta know, what the fuck was that picture about?!" Glancing over at me, Jamie's crooked grin slowly bloomed over his face.

"Well, either I was fucking with you or we're going to find out today." Laughter was lurking on the edges of his voice and this is what I'd missed those dull days.

"I swear I'm going to roll this car off the road if you keep playing coy." That prompted him to laugh, the sound joyful and full of life.

"Nice word choice. How bout we get to your place and figure it out there." He sounded happy and my hopes that this was going to continue surged back. Within a minute I parked at home, noting Donna's car was gone. Jamie brought his bag in with him and he went to my room, pausing once inside.

"I see you did laundry." Closing and locking the door behind me, I stripped off my coat and shoes, watching Jamie do the same as he studied the odds and ends of female clothing.

"So I guess it's time to figure it out." Shifting his gaze from my clothes to me, Jamie's face flooded with crimson. Lost in thought, he took a seat at my computer chair and spoke, gazing off into the distance at only something he could see.

"After last time, I went looking online and read something that stuck with me. It was from a guy had gotten gynecomastia from medication, only it effected everything else too. He said if you are shaped like a woman, 'have curves' as he put it, then wearing something that fits them makes sense." His face was blazing and his voice uneven but he plowed onward. "Here with you, I can do that. And I- I like the bras, how they fit and felt, the way they made me look." Molten heat flooded into my head and stomach, doing their damnedest to distract me but I still caught what he said next.

"I'd never thought anything like last time was ever going to happen. At least, not like it did." Struggling against the urge to tackle him out of the chair and try it again, I spoke up.

"That makes two of us." He looked up, startled, face still burning. "Yeah, I never did that before." Yet I'd done it like it was the most natural thing in the world and he responded in kind.

"Did- did you like it too?" Asked barely above a whisper, as if he was ashamed, I could stand it no longer. Going to him, Jamie rose and matched my embrace, so many complex emotions expressed through such a simple act.

"Your safe here. Anything you want to do or wear, it's yours. All you have to do is ask." I said into his ear, our frantic breathing pushing us together in ways that felt right. Drawing back, Jamie looked up and we joined in a kiss, soft, questioning. There was no demand, no expatiation, just him in my arms, free to do whatever his heart desired.

By the time his soft lips left mine, he rested his forehead on my shoulder and caught his breath, I was eyeing the hoard I had assembled for him.

"Go for it, anything you want. And if it doesn't fit, well, we'll figure something out." Between a scholarship, a small student loan that would inevitably come back to bite me and my job at the gas station, there was a pretty good chance I could pick up what he was after. And if he wanted the good stuff, I'd happily pay that bill to see him in it.

Turning, Jamie left my arms and that was for the best, as if I got my hands on his boobs or butt he wouldn't be wearing much of anything anymore. Meekly, he approached the buffet and began scouting around. Picking out a pair of jeans, he flushed a deeper red but lay them out before him. Shucking his hoodie off, I saw that he was wearing the same shirt from that night nearly a week ago and the typical black lace decorated bra.

"Do you, uh want to watch?" Still speaking in a small voice that was going to drive me insane, I shook my head, grabbing his hoodie off the floor and pulling it on, flipping the hood over my eyes and sitting in the chair.

"Not yet." If pressed, I'm not sure I could have given a good answer as to why not, other than the agonizingly slow reveal of Jamie was one of the greatest pleasures I could ever think of. I glanced out when I heard footsteps instead of changing, seeing him over by the closet and peering inside.

"Oh wow, you cleaned too." What in the thousand names of God was he looking at? Clasping my hands over clenched shut eyes, I sat there, fuses barely recovered from last time starting to blow out. There was no telling what he might decide to wear when I heard his jeans hit the floor, making my brain start to sizzle. More sounds of cloth, me straining to hear hard enough random colors that had no name floated under my eyelids.

"Okay?" Tearing the hood back, I saw him before the mirror, almost in arm's reach. Jamie had found the push up bra again and a shirt similar to mine with a low neck that showed plenty of cleavage. Instead of his loose and baggy jeans was a pair of mine, not fitting him perfectly but showing far more than his normal garb did.

"It's hugging my calves." He lifted a leg and I saw that was indeed the case. "Feels weird." I giggled at that, still coming to terms that he was in my pants, abet not in the way Donna would think. Turning around, Jamie looked at his butt in the mirror in a very stereotypical manner that nearly sent me into a laughing fit I might not have come back from. Sure, he was weaker in the hip department given that he was a guy but his butt filled out my jeans to a surprising degree. His thighs were on display as well and were impressive, well formed and fitting his height. Plus, I couldn't help but notice there was no bulge in the front where I'd expected one to be.

"Wow." My poor, struggling brain clicked into gear and deduced that if something was done with his hair and some make up applied, he might very well pass for a girl. And that thought blew out what little function remained in my head.

"Well?" Somehow blushing harder, the dawn actually spreading to his ears, Jamie spread his arms and faced me. "How do I look?"

"Like a girl and hot as fuck." That fell out of my mouth and I clapped my hands over the stupid word hole before it could do anymore damage.

"Well, that's kinda the point, isn't it?" Said with that meek voice, I groaned with need pulsing through my veins, both amazed and confused that this was my life now. "To see if it fits." All I could give him was a nod, all other systems having failed for the time being. It took an urgent question rising from the swirling chaos for me to find my voice again.

"Are you wearing panties?" That make him bite his lower lip in a way that made my ovaries scream for me to fuck him here and now. Lowering the waist of my jeans, I saw purple nylon I was quite familiar with, as they were mine. Jamie was fully dressed in my clothing from top to bottom: push up bra, v-neck shirt, panties and women's jeans. "Oh my God I'm gonna fucking die." Rising the hood once more, I leaned back and hoped to remember how to breathe soon. That idea, so simple and stupid, was making me more excited than some porn I'd seen.

"You okay?" He didn't sound concerned, which was good, simply asking how I was doing.

"I'm better than okay. Having the time of my life." Not too far from the truth, at least when it came to personal shit. "Just know if I get up, I won't be able to keep my hands off you." That was the damn truth and I stuffed my hands in the hoodie's pockets to keep them out of my pants.

"Is that a threat or a promise?" I laughed in the darkness made by his hoodie, stopping suddenly when I heard my jeans being removed, Jamie struggling from the sound of it. This fucked up fashion show was the only thing I cared about right now, the rest of the world none of my concern as long as this carried on. So I sat there, listening to Jamie strip and those sounds alone were some of the most erotic I could ever imagine.

"Hey Gen, can I-" His voice was small again, sounding like he was by the closet.

"Yes. Anything in here, yes. And I can't wait to see what you found." I heard Jamie walk and then sit on the bed, the familiar sound of him pulling something on slightly different this time. Then I heard a zipper and tried to figure out what that belonged to when another noise cut short that line of thought. While familiar, I couldn't place it, barely even able to hear the whisper. "Okay, okay..." Jamie muttered, sounding out of breath.

Sitting up, I flipped the hood back and saw Jamie standing there in something I'd forgotten I even owned. Still in the cleavage showing shirt and enhancing bra, he had found a denim mini skirt and stockings that darkened his legs while showing their shape off better. I got up and circled him, seeing this new sight from all angles.

The skirt had very few claims to modesty, showing basically everything except what lay between his legs. From rough estimates provided by my clothes, I judged he had more ass than I did but my hips were wider. From the back Jamie could have easily been mistaken for a girl, with his nicely shaped legs flowing up into a full butt. That I had humped and the memory of doing so brought my blood up to boiling.

"Well? Your too quiet." Answering him, I banished the fear in his voice by embracing Jamie from behind, as I had done once before. His breath caught as I leaned forward, nibbling on his ear, hands finding his breasts, making good on my threatening promise.

"What do you think I'm going to say?" A light thrust against the rounded mound I could now properly see and appreciate got a moan from Jamie, emboldening me further. "You look like a girl. Isn't that what you want to hear?" A shiver ran up his back as I started grinding, having returned to the actions of that insane night so easily.

"...yes..." Gasping, Jamie managed that single word, igniting some part of me that had been waiting to hear such a thing. Reaching down, I grabbed the already short hem of the skirt and yanked it up, revealing his plush butt wrapped in purple nylon and lace. Incited into some sort of amorous rage, I popped the button on my jeans and shoved those down, Jamie pushing back into what I had uncovered. My pubic mound slid over the smooth panty clad surface of Jamie's butt as he blindly rubbed, making noises that bored in my psyche. Grabbing his hips, I adjusted my legs and stance before pressing what I had to the covered crevice.

Looking past my rack, I saw where I had once taken a dick desperately attempting to be swallowed by Jamie's butt cheeks. He was plastered to my crotch, matching my hunger with his need, each stoking the other to dizzying heights.

Having lost control of my body and it's ravenous, unknown desires, hands that moved on their own accord up his body and found his chest, giving what lay there a rough squeeze. He cried out at that, trying and failing to push my soaked sex deeper into what was being offered. The fire that now wore my skin took his shoulders and turned Jamie to face me, glimpsing his startled, red face before greedily finding his lips.

Taking one of his arms, I moved his hand to my butt and placed it there, the timid presence growing bolder I did the same to him. There was no hesitance on my end, pulling him closer, fitted cups of bras I owned meeting as Jamie's tongue slipped out, meeting mine. I became aware of Jamie's ignored, insistent need, trapped as it was in my panties.

Two thin pieces of cloth were all that separated us from sealing the deal. A few errant tugs and we'd be free, able to fully engage in more than foreplay and yet, feeling his heat and hardness fighting in vain to escape was a perverse delight. My own aching emptiness, similarly imprisoned, this time pushed to Jamie's front. There was no chance for penetration but that didn't matter as he broke the kiss, returning my motion, unfamiliar without me being behind him. That was enough, both of us falling into a rhythm as he provided enough for my clit to rub upon, sparking pleasure that only added to everything that had come before.

Standing face to face, Jamie was a undefined blur that moved uncontrollably in the chest region as we humped away at each other. A whining moan came out of him, my panting the only answer he would receive. Gaining urgency, Jamie picked up speed and became more demanding, the hardness I was using to get off growing more so.

Hips pumping, breasts jiggling, we worked each other as our harsh breathing filled the room. Another cry came from him and the sudden burst of knowledge that he was going to blow a load in my panties pushed me over the edge as a final few thrusts were given and Jamie pulled me into an embrace, my orgasm deleting anything that wasn't Jamie for a span of time that seemed to never end.

By the time those cloying waves of bliss let me break the surface, I became aware of a wet, heavier heat soaking through my panties. Hanging onto each other, our breathing slowed as we took time to recover. Jamie's face was glowing, eyes still closed as his breathing slowed.

"I made a mess." Said in a meek and guilty tone, I couldn't help but laugh, the perfect way to cap off what had just happened.

"I know. It's hot." Taking my hands back, I stumbled back and fell on my bed, tripping over the pants pooled around my ankles. The front of Jamie's purple panties were darker from the mess he had made, the bulge having shrunk down. And Jamie was still wearing stockings and everything else, the skirt remaining hiked about his waist.

Kicking off the jeans, I went to my dresser and found an old shirt and tossed it over. I stepped into the closet and stripped off my own soiled pair of underwear, changing into a pair of booty shorts that I slept in during the summer. I stepped out to Jamie dangling my panties from a finger, face still flushed with lingering bliss. I pointed at the hamper and he dropped it in, with me following suit. I had no idea if he had replaced them with another pair and could be naked under the skirt, priming me for another round I'm not sure Jamie was ready for.

Slinging an arm over his shoulder, I walked him to the bed and cleared a spot, the both of us sitting, Jamie leaning on me.

"Is it weird to be sharing underwear?" He asked, catching me off guard and forcing my brain to reengage thought.

"I dunno. We can always go shopping if you want your own." Even after what he had done, Jamie still flushed red at the idea.

"Can't. Tom might find them and hiding the bras is bad enough." He sounded sleepy yet thoughtful, as if he still had access to logic. All I had was seeing him in a skirt and stockings and that image wasn't conducive to logic.

"You can leave them here. We can get matching bras and panties." A shiver racked him and I giggled, enjoying this so very much. But that idea was taking hold, it would be easy enough, Jamie was close to my size after all. Some measurements, an online calculator and we'd be good to go. Running a hand over a stocking clad leg, Jamie sat up and locked eyes with me.

"Long as your with me, sure, I can try. I mean, I-I want to but..." I caught his chin as his nerve broke and he tried to look away.

"Tomorrow, Sunday night, dead of winter, no one will be there. And if they are, fuck 'em, I'll be by your side the whole time. Just promise you won't bail on me." He nodded, color rising once more. "Promise?"

"Promise." He said, raising a hand and extending his pinky. I laughed and locked mine to his before speaking the next step. "Okay, gotta get your numbers now. Then tomorrow night we get in, find a few things, self checkout and done!" Nodding, Jamie wore a small smile as I looked for the measuring tape I had for reasons, similarly to the denim skirt he still wore.