Around The Bend - Stage 01

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"I, uh," my new voice sounded strange in my ears and I cleared my throat, fumbling for words. "I need to buy a bra. It's been a while since I've gotten one, I guess, and, I've, um, lost some weight...so I'd also like to get measured, please." I squirmed with embarrassment, unable to look her in the eye. Men didn't ask for help buying underwear. It felt like the first time I had bought condoms from the corner pharmacy when I was still a virgin!

"Sure. No problem," she enthused, turning on sales mode with a practiced smile. "Just have a seat over there. I'll get my tape and see if a dressing room is free."

I plonked down in the chair to wait and glanced around at the few women who were browsing through the racks of the quiet shop. I couldn't get over how strange and new everything was. From being the wrong height and shape to colors looking subtly different. Even something as simple and mundane as sitting down was a completely alien experience from my previous life. I could cross my legs without crushing my balls...in fact, sitting with my legs crossed felt kind of natural with the way my pelvis was now shaped. And the fact that I could feel my pussy squashed against the seat cushion was very peculiar. It wasn't at all unpleasant; it certainly didn't hurt. It was just noticeable...and odd. Like when you suddenly realize that you can feel your tongue sitting inside your mouth. Once you feel it, you have a hard time un-feeling it. I shifted my weight onto one butt cheek to take the pressure off my bits, trying to ignore the sudden warmth igniting between my legs, and wondered if real women ever noticed these things.

Nadia returned presently, "it looks like number 2 is open, if you'll follow me, please."

I felt like an imposter with a bad wig and an obvious Adam's apple as she led me to the small room and slid the curtain closed behind us. It seemed certain that there would be some giveaway, some small clue in my word choice or mannerisms that this woman would pick up on to realize I was actually a man inside this curvy, little body. I couldn't help but nervously grip my hands tightly together behind my back like a naughty schoolboy as I stood in this previously forbidden territory. I licked my parched lips and twitched an insincere smile at the saleswoman.

"Well...?" She motioned at my torso as she pulled a measuring tape from around her thick neck with her other hand.

"Hmm? Oh," I glanced down at my chest and fought back a worried expression, "uh, right. You need me to take my shirt off." I slowly tugged it up over my head, hesitating for a moment before letting my full breasts plop out into view, then I tossed it aside onto the floor. My nipples stiffed up from the chilly air and I realized how chafed and sore they felt from rubbing around the inside of that scratchy sweatshirt.

Nadia took my behavior in stride, an old hand at dealing with odd customers. She whipped the tape around me, pausing a couple of times to mumble under her breath as she read the results, "thirty-two and it looks like...an F cup." She wadded the tape up and tucked it into her pants pocket, "so, what were you looking for?"

I looked confused, "um...a...bra?"

It was a true credit to Nadia's professionalism that she neither rolled her eyes nor clucked her tongue disapprovingly. "Of course, sweetie, but what kind? Full coverage or demi-cups? Do you want an underwire? I don't think you want a platform or a push-up. Convertible straps or regular? Or would you rather have a racer back? Do you prefer tee-shirt bras or something a bit more for the office? Oh, and do you think you'll need any sports bras today?"

"I, uh, I'm not sure. Just...can I maybe try a few different types on?" Option paralysis squeezed my brain blank and I felt like a deer staring into the headlights of an oncoming truck. I thought I mostly understood what those things were from my experience with women, but I didn't want to look foolish just picking one at random and wind up with something I didn't really want. "Maybe one that's kinda full-coverage," I shrugged and felt the weight of my boobs against the flex of my shoulders. "Oh, and plenty of support. They get kinda heavy after a while." Yes, those seemed like good words to say.

Nadia gave an understanding nod, "sure. I'll see what I can find and be right back." She left and yanked the curtain into place behind her, leaving me alone with my thoughts.

I had no idea how I was going to continue to manage this from day to day. Coming to grips with the fact that I was a woman now was no easy feat, but there was no going back. The doctor had told me reversing the process could be fatal, and I wasn't interested in risking death. Damn my curiosity! Ever since spying on my sister enjoying her pubescent bits when we were both too young to really understand everything about sex, I had wanted to know what it felt like for girls. The seeds planted that day hiding in the hallway watching her fingers stabbing into herself and hearing her groans of pleasure had grown into a full-blown obsession and I had spent years daydreaming about the idea. It was difficult to fuel my fetish, too, because most of the men-transformed-into-women stories and videos were targeted at gay men, and I just wasn't terribly interested in dicks. I tolerated having one because it's what I was born with but had always felt like I should have the other parts. The old joke about being a lesbian trapped in a man's body rang true with me, but surgery was out of the question. I had considered and rejected the idea long ago after reading up on what it entailed, so I was resigned to just being who I was and leaving my fantasy in my mind...until I stumbled onto that website.

"Here we are," Nadia's voice interrupted my brooding a moment before she brushed the curtain aside and entered with a rainbow armload of lace and satin.

"I've got about a dozen different styles and all of them come in several different colors, so I'm sure we can find something here that will suit your needs. Let's start with this one," she held out a plain pink one with big cups. "Nice and basic underwire."

I took it from her uncertainly and tried to remember how I had seen girls do this. My sister used to put hers on backwards so she could do the fasteners up where she could see them, then spun it round and put her arms in. It seemed like it would be better than fumbling behind my back trying to do it up blind, so I gave it a shot and soon had shrugged the shoulder straps into place. A few tugs and twists like how I used to adjust my balls into my shorts, and I had the tight garment fitting somewhat comfortably around my torso. I glanced at my reflection in the mirror and couldn't help but smile as I pushed my shoulders back...I was a good-looking girl and this bra was doing very nice things for my boobs.

"Oh, yes," Nadia nodded sagely, walking around me and pulling at the garment to inspect the fit from all angles. "I think that one's a keeper. Do you like the color? I think it comes in white, black, nude and lilac as well."

"I think pink would be just fine, but it is a little...tight," I replied, shrugging my shoulders experimentally.

Nadia loosened the straps and tugged the bottom downward. Suddenly it felt like I was just wearing a very structured tank top instead of an awkward piece of too-small body armor. "Better?"

I twisted and bent around, reaching up and to the sides, testing my range of motion. I didn't realize just how much weight really was tugging at my back and how badly I needed this support until the unruly fun-bags were strapped down. I looked down at my cleavage and grinned, "much better. I think I'll be wearing it out of the store."

"Well, I do have a few others for you to try on before you go," she dipped into the pile of undergarments and held another out to me. "How about this one? It's got a little more sex appeal with this lace edging."

I sighed heavily and pulled straps down my arms, "fine. Let's see what else you've got." We spent a good hour together trying stuff on me and chatting about different fashion options and trends. By the end of it, I was mentally exhausted from fending off her aggressively suggestive selling, and my stomach was more roaring angrily than growling hungrily, but I finally stood across the counter from Nadia with a bag of bras between us and my phone in my hand, ready to pay.

"Alrighty," she said, tapping entries into her screen. "That'll be...two hundred and fifty-seven dollars and eighty-nine cents."

I blinked hard. "How much?"

"Two hundred and fif..."

"I heard you, I just didn't believe it. I only bought a couple of bras, not an entire wardrobe. There's, what, four of them in there?"

Nadia pursed her lips, looking displeased, and her saleswoman demeanor dropped away frigidly. "I thought so." It seemed I had finally reached the limits of her goodwill. "Our garments are of the very highest quality and workmanship. We do not cut corners in their materials or manufacturing. No cheap overseas sweatshops and slave labor like some brands use. And you're a very odd size that a lot of chain stores don't carry. If our prices are not to your liking, I'm sure you can find something within your budget online." She disdainfully raised one hand-drawn eyebrow as if waiting for me to apologize for wasting her time before I crawled away into the gutter.

I pulled up my banking app and held the phone to the credit card terminal. A moment later, a tiny beep indicated my money had been accepted and the transaction was complete. "Nah, I think I'll go ahead and get the ones I just spent an hour choosing, thanks."

Nadia ripped the receipt from the till before it finished printing, stuffed it into my bag and shoved the sack toward me. "Have a nice day," she said through the clenched teeth of a tightly forced smile. "Do come again."

I rolled my eyes, mumbling "what a bitch" to myself as I left the boutique. My pride may have dented my wallet, but she was right about the quality of her goods. Even though I was still wearing the same baggy, male athletic wear as before, I somehow felt a bit more confident and at ease knowing my breasts weren't jiggling and attracting any more attention than big boobs already do. Not to mention, the support taking some pressure off my back felt pretty amazing. 'How do girls deal with knowing guys are checking them out all the time? It's making my skin crawl feeling like there's eyes constantly on me,' I thought as a guy jogged passed. He gave me a friendly smile and nod as he went by, but I could see his gaze was focused on my chest. I staunchly refused to turn around, but the creepy tingling up my spine told me that if I did, I would see him trotting backward, checking out my behind. My confidence crawled back into its mental cave and I stuck my arm out to wave down a cab. I needed to finish up quickly and get back home before I had a nervous breakdown in the middle of the sidewalk.

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UAlbanyGirl518UAlbanyGirl518almost 2 years ago

The struggle is real! And you captured it almost perfectly. Interesting premise. I’m sad that you’ve chosen not to continue it.

AnonymousAnonymousabout 4 years ago
great story

really enjoyed this first chapter can't wait to see were his curiosity will lead him, is his sister going to be involved with her future development as new woman. i wish i could transition that easily.

sadiexx

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