Finding the Perfect Fit Pt. 11

If you're a first time reader drawn in by the tagline, Jamie is a guy with gynocomastia and Gen introduced him to bras then more female clothing over time. And that's all the backstory needed! Read on and I hope you enjoy!

This Fucking Week

Classes Monday and Tuesday, work Wednesday then home for Thanksgiving where I slept the first half of the day. After waking up and showering, I sat down at a fully loaded table with my Mom, Dad, younger brother and sister. After the traditional prayer, "Good food, good drink, good God let's eat!", we all dug in. It was then that I knew I missed this on some fundamental level. Sure, the freedom to do anything I wanted as a adult was nice but being here, having the safety of family who had my back gave me a sense of security I hadn't known I was lacking.

Conversation weaved in and out between mouthfuls, Ty asking me about college life and how it was different from middle school. While trying to explain that, Brooke butted in and asked if I was dating anyone and that question locked me up.

"...I, uh..." The answer was obviously yes but how was I going to explain Jamie without reducing him to just 'a guy with boobs'? He obviously wasn't a girl but that niggling question of if he wanted to go that far and all those thoughts, none of which could be spoken, smashed into a burning train wreck inside my skull.

"Gen's gotta boyfriend!" Ty shouted, throwing his hands up in glee. "Or is it a girlfriend again?" My Dad, who was taking a drink when that was said, slammed his glass down and started pounding the table, coughing and laughing at the same time.

"Well, which is it?" Brooke asked, food completely forgotten as she looked on, ever curious about who I was dating. If I said boyfriend, there would be a certain expatiation that Jamie wasn't going to meet but that wasn't fair to him, he hadn't chosen to have boobs!

"Look, I'm seeing someone and that's all you need to know. I can't exactly bring anyone home to this freak show." Dad flipped me off for that, grinning all the while. When the word about me fooling around with Cass had reached home, he'd called me into the garage and we talked while idly taking apart an engine. While his eyes were on the machinery, he spoke calm and clearly, letting me know that as long as I was safe and happy, he didn't give a flying fuck who I was seeing. I just had to be ready for the rest of the world to give me shit for it. Wise words from someone who swore enough for three people.

"Man, my life sucks! Gen's having fun in college and I'm stuck here!" Ty pouted, driving his fork into a half devoured slab of ham, lower lip pooching out in a remarkably childish manner. I'd been gone for a few months and while it felt longer, it was clear my younger brother hadn't grown up too much.

"Fun? Alright, tell me how fun my usual day sounds: Get up, go to class, find time to eat then go to work, come home, remember to eat then do homework til ya pass out. Then do it again four more days til the weekend, which ya spend workin' or doing homework on top of trying to have a personal life so I don't fuckin' lose it!" Locking eyes with my little brother, I reached over to his plate and poached a roll, Ty seemingly rethinking his whole life thanks to my tirade.

"Good to know some things never change." Mom chimed in, swirling her glass of water as she looked from me to Dad.

"Yeah, that shit sounds familiar. Fuckin', between me working at the shop and her going to school, we'd barely get to see each other some weeks. Hell, I'm pretty sure ya were conceived at Dick's, one night I was workin' late and ya Mom shows up with some McDonald's..." Aiming a wicked smile at his wife, my Father made exaggerating kissing noises as Ty feigned gagging, shaking his head as I shrugged. Wasn't too surprising to learn, if true.

"How romantic." I chimed in, already calling myself a hypocrite, dry humping Jamie in the back of my car after grabbing Burger King or talking about anal over breakfast. I really was my father's daughter.

"It's the thought that counts, especially when there isn't much money to spare." I nodded and Mom gave me a knowing look before turning her gaze to Brooke. "Try and remember that, Juliet." Rolling her eyes, Brooke looked back at me and picked her next words carefully, a skill Ty lacked.

"Is it that bad for you and your... Significant other?" Brooke asked, with pity in her voice. However, I'd started laughing at her careful handling of me not telling anything about Jamie and couldn't stop.

"Give it a break Brooke, you'll be dealing with the shit soon enough." As a freshman in high school, she had a year or two before needing to find a job or get good enough grades to stack up scholarships and that last was probably wasn't going to happen.

"Ya could be helpin' me in the shop, waitin' for the Ford Pinto someone brought in to explode!" At that, Dad started cackling as Mom sighed, rubbing her temples.

"I swear to Christ Almighty if I see another mechanic kick that rear bumper, ya'd better hope it kills us all!" Getting myself back under control, I resumed eating as the usual scene played out, Dad feigning innocence he couldn't quite pull off as Mom rattled off a list of stupid shit the guys at Dick's had done. So Thanksgiving as usual.

Once we were done eating and the food was stashed in the fridge, I crashed on the couch to an old black and white movie. Waking up refreshed a few hours later, we all went to the garage and Dad put on some classic rock as I picked up a broom. It was one of the few times a year all us kids could be gathered in one place without running off to a friend's house and so cleaning began. Sweeping, then scrubbing the fresh oil stains in the hope of making then fade into the hundreds of others that littered the concrete, then going over the tools with rags and degreaser, sometimes uncovering a faded logo from under the grime.

While it might not have been any one else's idea of a good time, I relished the chance to be here and do it again. Sure, there were new stains and tools I didn't remember but it was familiar and known, time worn. When Dad called it a night, I had that warm glow of satisfaction my job at the gas station never gave me.

Friday I camped out on the couch in the living room, chipping away at homework and watching old movies with Dad, the kind that rendered the world in black, white and gray. I'd never been interested in this kinda thing before but it really caught my attention, being informed they were called film noir, and I was enchanted by how the world was portrayed without color. The cynical tone was what really hooked me, the leading guys so jaded and weary of it all yet still going forward with what had to be done. I passed out that night to another woman with a troubled past coming to a private eye who was wearily pouring himself a drink before she knocked.

Saturday morning went much the same way until I started gathering up what little I'd brought, Brooke and Ty begging me to stay but I insisted I had to get back to my dorm, using cleaning and finishing up the rest of my backlogged homework as an excuse. Loaded up with leftovers and promising to visit more, I tore myself away and returned to the largely abandoned campus, cold and still.

The little dorm house I shared with Donna seemed dim and forlorn after being home. Even so, it was going to be lively in a hurry once Jamie showed up. I'd been texting him all break and he repeatedly confirmed plans hadn't changed and the time was drawing close now.

Running a nigh scalding bath, I gave my room a quick cleaning before hopping in and shaved everything from my navel down, then did armpits too. Leaving the enveloping steam, slightly light headed from the heat, I ate leftovers as Jamie texted that he was on his way back.

Dumping my plate in the sink, I went to my open closet and looked for what I was going to wear for today's main event. We had the place to ourselves and I intended to use it. Jamie had been coming here to explore, discovering clothing that was useful then what made him feel good. I'd encouraged, enabled and drooled over him doing so but I really hadn't joined in on the fun. He liked wearing push up bras, slinky panties and nylon stockings so odds were good he'd like all that with me in them, too.

I laid out my garb, then dug out Jamie's stuff and set it on the bed. Out from under the bed came the Butt Bag; Lube, condoms and the plug I'd used before being liberated as the rest went back out of sight. Using another rubber to apply lube, I got a finger in easier than last time after a few calming breaths. Playing Dreams again on my phone, the plug slid in on my first try with a groan. Wiping the extra lube up, I sat there catching my breath, keenly aware of there being something wedged in my ass.

A text got me snatching up my phone, muting Stevie Nicks mid word as Jamie let me know he was five minutes out. Heart hammering, I got dressed in what was for Jamie's eyes only then put a shirt and jeans on over that, yanking my shoes and coat on as I walked out and got my car started. I paced in the crisp and clear cold, the plug disrupting my thoughts along with amping me up. Giving it three minutes that dragged forever, I hopped in and cranked the radio, Dead or Alive blaring out as I drove across the campus.

I saw Jamie standing in front on his dorm, typing on his phone as I revved the engine and pulled up in front of him. Rolling the passenger side window down, I saw his red face bend down to peer in at me.

I leered, "Hey there pretty thang. Hear ya wanna stick it someplace naughty!" Somehow going even redder, Jamie yanked the door open and jumped inside, making a shushing noise the whole time. "Relax, there's no one here yet."

"Tom is! How do you think I got back?" I had nothing there and instead rolled the window up and slowly got us moving back to my currently empty place.

"Ya ready?" Jamie nodded, then started giggling, biting his lower lip to keep it all together.

"I feel like this shouldn't be happening. I dunno, after so long without sex that it being this easy? That we talked it over and agreed to it seems... Wrong? Anticlimactic?" Jamie shrugged, his coat mostly eating the gesture but I heard the amused bafflement in his voice.

"Hey, it's one of the perks of being an adult. You want to bang me, I want to bang you, we let each other know and here we are." Reaching over the center console, I took one of his hands as I failed to find anything else to say. So we drove the final stretch to Paint It Black, which might have been ominous to someone who didn't have a butt plug in. Having come this far, it'd take divine intervention to stop me.

Parking, I locked my car and once we were inside, I locked the front door. The couch where Donna was usually camped out was empty, Jamie having noticed on the way to my room. I followed, giddy in the idea that his ill fitting clothing was going to be coming off shortly and I'd get a chance to see his boobs again.

Closing the bedroom door behind me, I sat as Jamie gestured to what I'd laid out for him. "Am I that predictable?"

"Ya welcome to anything else I got." Jamie smiled and shook his head, shedding both coat and hoodie.

"Please, that was me trying to be funny." Holding the push up bra he'd worn before, he looked over at the mirror in the corner and I saw a curious expression on his face, one of longing and uncertainty before grinned, seeing me in the reflection. "Wanna watch me change?"

"Nah, I think I'll be seeing most of ya soon enough." Turning my back to him, I waited until hearing his clothing hit the floor before joining him, kicking off my jeans and letting my shirt fall to join them. Hearing my mattress protest, I turned to face Jamie, who was carefully pulling up his pair of stockings. I instantly noticed and blurted out: "Hey, you shaved!"

Looking up, face red, Jamie took a minute to say something.

"Uh, wow." I was in my underwear and he was getting a good look. "Yeah, uh, I wanted this to be the best it could and I like smooth legs so I figured, why not give it a shot?" Walking to him, my nylon clad feet making hushed whispers against the carpet, the plug in me make itself known anew. He watched with huge eyes, pausing in pulling up the left stocking. Leaning down, I ran both hands from thigh to knee and down his calf. There was a nick here and there but overall he had gotten it right and provided another thing I hadn't know I was missing.

Taking hold of the top part of the stocking, I pulled it up to mid thigh where the elastic dug in enough to hold it in place. The lacy black panties were failing to contain Jamie's excitement and I had to restrain from getting it on right there. I wanted this to be the best it could for both of us and there was still a few steps left. God, it was so hard with his boobs right there in my face.

"Make up?" Jamie blinked as I stood up and wondered over to my desk, needing to get out of reach of him. I also needed to make some sense but this waiting, drawing out the inevitable, was making me delirious. "I'm going to put on make up, you want in?"

"Sure? No, yeah, I do." There was eagerness paired with a hesitance that I was coming to recognize from him. Sitting down, that simple act reminding me I was plugged, I did eyeliner and shadow along with lip gloss, then added mascara that I found hiding behind the small mirror I used to apply it all. Jamie watched the whole time, making idle small talk and checking his rack from time to time.

"So how did using one of those things go?" I got up and gestured for Jamie to take a seat, finding a brush and dealing with his hair first. He'd combed it but it needed more attention and the waiting was going to kill me.

"What, the butt plug? It's awkward but not so bad once it's in." Jamie grunted as I worked out all the rats and snags, getting his brunette hair shining in the light. He'd kept up using the conditioner, that much was clear and it benefited him. "I just hope it works."

"I was wondering when you'd put it in..." He trailed off, blushing, as I told him to look up and not move. Eyeliner was applied with a few complaints about how close the pencil had come to blinding him, then mascara and he picked lavender for eye shadow, which I applied. Puckering up when I got the lip gloss, I got that on his, for once, un-chapped lips and he rubbed it in as I had taught him that first time.

"For your information, I put the butt plug in probably thirty minutes ago." His eyes, now rimmed in black, widened in shock and his natural color made it clear blush was built into Jamie and any extra was a waste.

"I, when I was shaving in the bath I got curious, seeing how it's going to be my turn next..." Now a bright scarlet, heavy lashes blinking in rapid succession, Jamie fidgeted until I extended a hand and pulled him to his feet.

"Jamie, I have something up my butt and soon, it's going to be you." His face twitched, as if he was going to laugh or explode but I carried on. "Just say it, whatever it is. I won't laugh, I swear."

"I got a finger in when I was shaving." A shuddering breath and I pulled him into a hug, feeling his nigh naked body against mine.

"How did it feel?" I asked, loving the silky feel of his hair as I ran hands about Jamie's waist as he took hold of my ass. I moaned my approval, losing what little control I had with each passing second.

"Weird. It... I, can I try one of the plugs today? Before we get started?" I looked down at him and Jamie, the green of his eyes more vivid by the make up, pleaded without words. "I know it's not my turn yet but I want to know." Kissing his forehead, we joined lips without speaking, desperation pouring off him. I took hold of his butt with one hand as the other slipped up to take hold of a breast, giving the bra a squeeze that generated a moan that passed to me via our kiss.

Taking a few tangled unsteady steps, his stocking clad legs brushing mine and that slinky feeling added to all of the things Jamie was to elevate this ever higher. With a slight push, Jamie fell back on the bed, leaving me standing over him. Strutting to the side, I bent over and pulled out the bag, dipping a hand in to toss the other butt plug at him.

"Get comfy, I'll take care of it." Finding the shirt I'd used before, I tapped Jamie's hips until he lifted them and I laid it out to catch any spillage of lube. Running fingers over his trapped package, he gave a frustrated groan that I understood all too well. Teasing down the panties, I was amazed that everything had been shaved clean and felt the smooth expanse above his straining dick. Slipping his underwear off, I unwrapped a condom and slipped it on a finger, a gesture that was becoming familiar.

"Spread 'em." I said in a gruff voice, Jamie raising an eyebrow and reducing me to laughter. "But no, seriously, spread ya legs." Cracking open the lube, I drizzled some on my finger and then slipped it between Jamie's cheeks, getting a gasp from him.

"It's cold." One look at him made it clear he was too tense for anything to go in there, eyes wide and fists burrowed in the blanket.

"Jamie, ya gotta relax." I grabbed his dick with my other hand, giving it a few strokes. A moan was his response, his hips raising away from my venturing finger. Well, that wasn't working but I wasn't going to give up so easily. Situation myself, I took his dick in my mouth while sliding my finger until I hit close enough to where we both wanted to go. Savoring the yelp I got, my multitasking was tested as Jamie got head and tails at the same thing, spreading the slick gift over what I eventually found.

Sitting on my haunches, I grabbed the bottle of lube and poured too much right behind his balls, then scooped it up the best I could and got it where it needed to be. His cock was pulsing, as if furious it wasn't the center of attention.

"Breathe, relax, take it easy." Keeping my protected digit lightly pressing on his entrance, I shuffled up and kissed him.

"I'm trying. Here, just..." Reaching, he undid the bra clasp and tossed it aside, Jamie's chest on display and it held my attention. Without needing to be asked, I lowed and enveloped the peak closest to me, his back arching at my touch. Falling into a tempo I'd never dare to dream of, I sucked and licked at his breasts while never ceasing my motions down below.

Jamie's breathing evened out, one of his hands idly stroking himself and the other burrowed in the blanket as I smelled the flowery, clean scent of soap while taking my pleasure. On and on tongue and finger worked, the first going round and lapping while the second moved up and down, up and down then applied slight pressure. There was no hurry, everything was eventual. I switched from one breast to the other, getting a murmur of approval for doing so.

A moan rang out as a hot, tight embrace took my finger. Jamie's eyes went wide, the liner doing its job of making them stand out as he looked from me to his lower half. Scooting back down, I took my time slipping more in, second knuckle then all of it was inside Jamie.

Spreading his legs wider, he shifted some then started to speak before I, very carefully, pushed what was in as far as it could go. The rest of my hand was stopped by his bubble butt but I stole what he was about to say from him. I hadn't been sure of what to expect but Jamie's ass was the same as mine: once past that tight ring it opened up and I explored, judging from his expression that I was doing something right.

"I'm going to try another finger, is that okay?" I asked, knowing the uncomfortable awkwardness he was in right now.

Slightly out of breath, Jamie nodded, "Yeah, go for it." I got my ring finger into the condom and soon too was requesting entrance and I watched his dick give a jump as it joined the other. Sliding them both nearly out, I slowly encouraged my fingers back in, the only part of Jamie that still had clothing left on stirring the whole time.