While Chasing Our Dreams Ch. 02.2

Damn. Talk about the long game.

"If you mean, which princess I am most like, I think by default I'd have to say Belle."

"Because you love to read, and you defy social expectations?" My gorgeous friend beamed, stepping into her body and running his fingers down her cheek.

"Well, that, and because I have a taste for big, scary men," Jane snarked back, darting a glance up at me. I had to guffaw.

"I had a feeling you might lean that way," M snickered back. "I like big scary men too." He bent slightly to kiss Jane, and their lips met. Our girl moaned softly as she wrapped him in her arms and kissed him back. God, they both wanted me, and I wanted both of them... That was my revelation.

When they broke apart, Jane was panting.

"But if you meant which princess dress I like the most..." She picked up their conversation as if it has never been interrupted. "Honestly, most of them are too pastel for my color palette. I like bold, rich, saturated colors, and I look best in red. There aren't any princesses with gowns like that. In that sense, I think I'd look best in Snow White's gown, or maybe Ariel's. Merida's too."

"Nothing out of the realm of possibility, baby girl," M held her close. "I'll see you dressed as all my favorites if I get my way." Sticking her ass out, Jane leaned into my prettyboy and hugged him. She walked her fingers up his chest and stroked along his jaw.

"Don't go too hog wild just yet, M," the naughty slut calmed him. "You have all the time in the world to dress me like the princess of your dreams."

"Coincidentally, my biggest fetish," Randy shot over his shoulder. "But in my world, you're the sluttiest princess in all the land!" A ripple of laughter took us, and M eventually took back his collar selection so we could add it to the (soon-to-be growing) pile of goodies we were buying. Jane's choice wound up being green leather with a leaf imprint. Simple but nice, and rounding out her color needs. I sent Randy to the counter with the collars and made Jane return to the sex toys so I could pull M aside for a quick minute.

"I know you're dying to wow her with something expensive and fancy, but our Jane is a very unconventional woman. You're going to have to wait until you see her light up over something. That said, you're in luck." I kept my voice low so the girl in question wouldn't overhear. "She brought us to a place where she obviously loves the merch, so there's bound to be something to splurge on here. Plus, the lady said corsets, M." Those big blue eyes got bigger.

"Corsets! Of course!" M turned fast and bolted. I chuckled, and sauntered back over to Jane, who'd I'd left staring at the dildoes and other fuckables. A fuck toy for my fucktoy. I had some plans. First- Jane was going home with a set of butt plugs and my strict instructions on their use. We'd lose a lot of valuable training time being separated from her, which meant she had to practice, prepping herself with the plugs and maybe a set of anal beads. Taking her ass was a big goal. And anal toys were exactly what Randy was looking at, right by Jane, staring at the big stuff.

"Pick out a 'kit', Randy. Little girl has homework after we drop her off."

"Ooooh! Are you thinking what I think you're thinking?" In response, I nodded.

"Progressively-sized plugs, beads, and lube. And tonight you're gonna show her how to use them properly." Randy hooted excitedly, and Jane squirmed in place. She was meant to be predicting which one of the toys I was going to buy her that very day.

"Master...?" She began tentatively. I shushed her.

"Now that we've gotten to know your body and what you need to get off, baby, we're adjusting your toy collection and your training. I'm actually pretty glad you brought us here because it makes the selection process so much more fun." I leered at her somewhat evilly and made her face the dildoes again. "So tell me, Jane. Which one of these will be yours after today? Which one will I make you fuck for me on command?" My girl visibly shrank, and swallowed.

There were quite a few toys of all sizes, shapes, colors, and capabilities on the display. Vibrating shafts with multiple functions, realistic thrusters, cocks with balls, cocks with no balls, G-spot toys, sleek vibes, jelly toys, chunky and long ones, slim and straight ones... Anything I could want. And I had my eye on something in particular. Nothing jelly, because I'd read they weren't the most body-safe toys, and I didn't want to get her a vibrating or thrusting toy. Something realistic, yes. With balls. Something thick, and long. Jane's pussy was so fucking tight, and if what she said was true, sex with Randy or me might become more difficult for her over time. That meant she needed to exercise her cunt and get it used to big penetration, because believe me, we were going to be stuffing her full.

Everything was on the table here. We were going to eventually DP her, take her in all three holes at once, and probably even go for double-vaginal plus anal; maybe even fisting! That hot little slit of hers was ours to use however we wanted, according to Jane, and if we were going to use her both thoroughly and right, well- practice makes perfect.

She'd have to get used to taking big toys and big boys. I was gonna turn this tight-pussy slut into a bonafide size queen.

I think Jane saw the look on my face deepen and twist as my wicked plan took shape. She started to tremble against me. To start, I was gonna need something at least five inches thick. That was roughly about as thick as either me or Randy. Without fucking her for a month, she'd remain too tight and we'd have to start over. With a couple of big toys to use on herself, her flexibility would improve and hopefully our roughest play wouldn't be too much when we did get back together. Beyond that, I really wanted to push her limits, so I needed something even girthier than that- maybe a toy seven inches thick. The key was to increase gradually.

"Um..." She answered me shyly. Her eyes darted from me to the items and back. "I- I don't know, Master. I'm not sure what purpose you're trying to fulfill."

"Guess," I commanded, squeezing her. "What do you think is the first thing I would want to accomplish in your sexual training?" I saw her mind ticking and she perused the display again. Finally, she answered.

"You'll need to prep my a-ass." Her words warbled a bit, and I chuckled.

"Well, you're not wrong, but that's going to be largely Randy's department. That's why he's picking out some toys for you to that end."

"Pun intended?" The scrawny nerd shot back, his arms full of plugs, lubricants, vibrating anal beads and an anal douche kit- presumably to deal with Jane's "squicky" issues. Probably would make her more confident when it came to anal. Sounded like she didn't have very much experience.

"Nope, not intended. Still fun though." I grinned at Jane, who was starting to look glassy- and a bit overwhelmed. To comfort her I wrapped an arm around her shoulders and held her to my chest. "I'll give you a hint, Jane. I need to be able to have rough sex with you and not break you." Her eyes widened in realization. She glanced back over the toys.

"You'll need to buy something big enough to get me used to your size," she finally uttered breathlessly. I squeezed her.

"That's right. Randy's too. We need to stretch those muscles you've tightened up doing Kegels, which means you need a nice, wide, thick and long toy to fuck yourself with while we're not together." I finally reached up and pulled down a light-colored realistic dildo that had a slightly curved shaft, and put it in her hands. It was nine inches long from tip to base, had fake balls attached, and was about five inches around. A size roughly between me and Randy. "You took us in your pussy, you'll be able to take this too."

"Ohhh..." Jane moaned.

"You'll fuck yourself with this just as hard as we watched you fuck yourself with the toys we already bought you." I watched her examine the daunting thing with trepidation until Randy passed by on his way to the counter, and piled it on top of the anal stuff. "Get her extra lube too, bro."

"Can fucking do," he said as he passed by.

"Is it a bad thing that I can't take so much size?" She asked mousily, still tucked into my chest. "Even after a year with Paddy, it just started getting harder. Is there something wrong with me?"

"Oh god, baby, no!" I reassured her, taking her shoulders, making her look up at me. "I can't say what made sex more difficult for you over time with him, but it could've been that you weren't as excited, that there was less foreplay, or just stress that made you tense up. It's not anything wrong with you, Jane, trust me." Little by little I could see her uncertainty cracking and melting away. She felt safe with me, seen and heard. That was vital to building trust and cementing our D/s relationship. "I promise you we're going to take our time, make sure you're always aroused as hell and ready to fuck us. Randy and I both know we're big, and we don't want to hurt you. Thus, practice."

"So you're basically exercising my pussy?" She began, regaining her confidence.

"Exactly." With that I plucked another toy off the wall. A real monster, by her standards. Like the other one's bigger brother. Straight shaft, nice and veiny, big head, balls, and measuring a good twelve inches with a seven-and-a-half inch girth. Now she really shook. "We're going to work you up to this. Do you know why, Jane?" There was a mix of fear and arousal in her expression. "Do you know how many different ways we can fuck you?"

"I... um..." Eyes caught on the toy, she stammered and searched for words until Randy returned.

"Ooh! That's pretty hefty. I think I see where my bro's going with this, Janey."

"In my defense, I don't watch porn," she sputtered. "I know you'll eventually take me one in the ass and one in the pussy, with or without me sucking the third." I nodded.

"Very true, subbie, but there's more possibilities than even that. Did you ever think about what it might be like to have two cocks in your cunt at the same time?" Her eyes flew open.

"Or that we might fist you?" Randy snickered, holding up his clenched hand. Jane really goggled then.

"That's possible?!" The squeak in her voice betrayed her shock. Randy had to cover his mouth to keep from howling out loud. Instead he managed to squash it down and forced out:

"Oooooh, dirty girl doesn't know about fisting!" I saw her cheeks turn red.

"That can't be possible," she said again, in total disbelief.

"With effort and work, it actually is," I told Jane calmly. Still smirking though. God, so slutty but somehow so innocent! I guess to her, fucking all three holes at once was the ultimate three-men-one-woman sex act. Just you wait, Jane, I laughed in my head. I pictured her eyes crossing as she fell apart with two cocks in her snatch and one in her ass. Sex with three men was going to be so intimate and so dirty for her; I practically salivated imagining her noises and reactions as we introduced her to sex acts she'd somehow never dreamed. "The vagina is pretty amazing, Jane. Think about it- how else would you give birth?"

"Well of course," she replied quickly, an edge in her voice. Like, I do have a pussy, you know. But then she got soft again. There was something in her face, something that made her sad and took her elsewhere for a minute, before she shook it off. "I guess I just never thought about how big a baby's head really is, and I mean, there's like the whole body after that."

"And my fist isn't gonna be quite that big," Randy said, dropping his arm. "Neither are our cocks, even together."

"Sharing your pussy like that will be amazing for all of us, Jane," I rumbled smoothly. "And by training you up, it'll all be possible." Our girl sucked in a deep breath and let it out slowly. She became visibly more relaxed.

"I trust you guys," our girl eventually told us. "I trust you to work me and pleasure and take my pussy in every possible way." Randy let out a groan.

"I feel like I'm missing out over here," M suddenly interjected, coming from behind us with his arms full of corsets.

"Master is going to help me stretch my pussy to take you guys," Jane told him, still blushing.

"Ah! Good plan. You are very small, sweetie. Plus, think about the future benefits! If we help you develop your elasticity, you'll have an easier time giving birth."

"That's probably true, isn't it?" Jane stated. "Huh. I wonder..." There was that look again. I had to press.

"What is it, Jane?" She looked at me like a startled deer, knowing she'd been caught.

"It's just... I've heard stories, you know? About women splitting open from birth? I feel like... I'm so tight, I might not be able to..." Randy and M moved in to comfort her at once, and I stood slightly back, thinking. That was an honest answer, but it felt like there was more to this than she'd said. But, instead of pushing her to tell me and possibly open up something she wasn't ready to discuss, I filed it away in my head and didn't let her know what I'd seen.

"It is scary," I replied mildly. "Birth isn't easy, Jane, but we're going to be there for you during the entire thing when you give us kids. And we can get you ready for it with fun time. That's why I'm buying this." I held up the big dildo.

"Everything comes down to exercise, honey," M said. "We'll take our time working up to double penetration and beyond, and when it's baby time, we'll have thorough birth plans and do everything we can to make it easy."

"Do you know how many pregnancy books I've already read?" Randy put in. Jane embraced them both and smiled.

"You guys make things much less scary." She rewarded them both with kisses, and I added the other toy to our pile. The sales lady was thrilled, keeping up a tab and making sure our purchases were organized and ready to be packed up. She paused me when I turned back to my people, and asked

"I saw your friend looking at the corsetry. Do you need any help with sizing?"

"Not a bad idea," I said, and she followed me back.

While M pulled Jane aside to get measured and to browse the corsets, I took a look at the lingerie and accessories. Randy followed me in to help grab some items of interest, and the two of us assessed the Queen-sized goodies. We scooped up roughly a dozen teddies, body stockings, babydolls, bustiers, and two/three-piece lingerie sets in a variety of colors and styles in the hopes that most of them would fit and look good on Jane. As I brought them to the counter, Randy split off to join the corset brigade. M was busy showing Jane the few he'd picked out. Some gorgeous designs, actually, in a wide multitude of colors. Florals, brocade, plain leather, latex, vinyl, satin, fleur-de-lis, lace, sequins, ruffles... I had no idea corsetry was so varied. Jane was stroking items with her hands, and I saw it on her face for the first time: She wanted. Not like that dress at the Disney store. The wonder and desire were right there in her expression.

"Ooooh! That one's so pretty!" She gushed over a purple Mardi Gras-themed item, complete with feathers and golden detailing. "But this one is totally my style..." she said, darting over to an emerald green one with black pinstripes. "And this one! Ooooooooh!" A loud squeal of pure excitement escaped and I caught Randy's saucy grin. She was easily just as boisterous as he was. M was moony and delighted, pointing out designs and holding them against Jane's torso to get an idea of how they would look. He'd found his groove again. The search continued until I heard a throaty gasp, and Jane went dead still. We all paused, watching intently. She reached forward to draw a corset into her hands. It was black, with the body being a subtly shiny cloth material- very classy. It was the metal hook type, meant to be clasped and then tightened (as we learned during this stint). I think what caught Jane's eye, though, were the embellishments.

Embroidered in serious detail, the corset had lush roses- red blossoms with green stems and thorns- and skulls. Really well done, too. Randy whistled. Jane's expression was lit up with delight. I looked toward M. His expression was amused, maybe a little quizzical. He sighed, shaking his head, but was smiling.

"That's the one, isn't it?" Jane turned. "You want it, Jane?" I saw her check the tag on the side. Size? Price?

"First things first," she said.

Minutes later, the shop clerk was lacing her into the skulls-and-roses emblazoned corset, and Jane was adjusting her breasts as it went (the "fluff and tuck" method, she said), but she was smiling wide. From what I could see, it fit. First the woman had to loosen the ties in the back, then put it on Jane and clasp the hooks. Apparently this was an "overbust" style, meaning that it would support her breasts without the use of a bra. Since she was already wearing one, the try-on here wasn't going to be too serious. It was just to give the precious little slut an idea if the thing would fit. As her waist narrowed and her breasts were pushed up to spilling over, I noticed how well the corset matched her whole outfit. Probably not an accident, considering. She really did look damn good in red and black.

Once it was on, strings tucked, the feisty sub examined her reflection and clapped with glee. She turned to us, excited, and showed off the incredible figure she had that was enhanced by the garment. Cocking one arm on her hip she slyly grinned, and asked:

"So... What do you think?"

"It looks damn good," I groaned, my voice harsh.

"No blood in brain," Randy blurted out, staring her up and down.

"Sweetie, can I be honest?" M began, and I saw her smile dip. He didn't let her fret too long, though. "I can tell we have different tastes in style, and I definitely wouldn't have expected skulls and roses, but my God, honey. It's gorgeous." He stepped close and caressed the raised design, then up the hooks and across Jane's cleavage. "It looks perfect. Suits you exactly, and... I love it." M lifted her chin with his fingers. He lowered his mouth and took her in a smoldering kiss. Jane moaned and melted against him.

"I think our golden boy has become a man," Randy quipped at my side. "He was used to dating those soft society girls. The really prim and sweet ones, you remember? He's never been with a girl like Jane."

"Yeah, she's really more like the adventurous, alternative types you usually go for," I replied, "a bit more of an edge."

"An edge?" My bro snorted. "There's a bonafide goth in that girl's heart. I once asked her what three fictional characters she was a combination of, and she said Sailor Moon, Max Black from 2 Broke Girls, and Wednesday Addams. With a side of Lydia Deetz!" When M and Jane broke apart, I heard her giggle.

"Randy's right," she copped. "I never like, dressed goth, because I love vibrant colors and archaic styles, but if you dive deep enough in me, you'll find a taste for horror, too much information about torture, execution methods and serial killers, and an abiding love for the works of Edgar Allen Poe." M blanched, obviously caught by surprise. She smirked, and reached to his cheek. "Can you live knowing your princess is a warrior queen, forged in bloody history and dark literature?" The blonde prince grasped her hand.

"Yes," he replied firmly. "I get why you like Merida the most, honey. You're a princess who chooses her own path, one who will defend herself and others. You're not... some helpless damsel."

"Do you ever think about how many of the earliest Disney princesses are just that? Subservient, helpless, pretty, domestic fainting maidens that have to be rescued from evil by men? Some of them sexually assaulted in their sleep?" Her forthrightness struck M again but he stayed upright. His face paled, though. "I mean, we even know Ariel can write. Why the hell didn't she write Eric a letter?"