Modest Mingling

“Oh my gosh, Bitsy?!?”

Bitsy lifted his head just in time to be all but tackled by a blur of periwinkle, lilac, and lavender. Celestia help him - he thought he’d been ready to see her in person, but her jubilant greeting and affectionate embrace brought his anxiety raging back to the fore. Meeting somepony new, even if he’d been chatting online with said somepony for months, had never been his strongest suit.

Only eventually remembering his manners, he halfheartedly returned the hug. “H…hey, Dawn.”

She released him and withdrew as quickly as she’d thrust herself upon him. “It is so, so nice to finally see you - well, actually see you,” she giggled. “I hope you’re hungry, because I sure am.”

As he weakly smiled, his eyes ran up and down her frame. With a luscious, flowing mane, shapely physique, and a broad, welcoming grin, she was just as pretty as her photos had made her out to be - so much so that he’d bitten the bullet and taken her up on her offer to go out for lunch. Though he hadn’t given a reply, unsure of what to say, he gave a small, subtle nod.

“C’mon, we should get moving if we want to beat the lunch rush,” she cheerfully tutted. Without skipping a beat, ignorant to or outright ignoring how tense he was, she reached out, locked hands with him, and turned away. “Trust me, you are going to love Il Piccolo Cuoco! They have got the best pasta I’ve ever had!”

“I…I heard they’re pretty good,” Bitsy lied through his teeth.

While she led him through the parking deck of the monolithic shopping center, he swallowed hard. Buck - this wasn’t going to be easy. He could and periodically would go out to run errands, although that was a far departure from going out with a mare - a young, attractive mare. There weren’t many mares he fancied, and fewer still that would actually talk with him, but he’d be darned if Velvet Dawn hadn’t done both in spades.

“Hold up,” she murmured.

Nearly running into her when she came to a dead stop, Bitsy looked up to her face and froze. She was looking dead at him, and that revelation was terrifying. Had she caught him eyeing her backside? Could he have done something wrong? What was happening? With his apprehension skyrocketing, he fought the urge to start apologizing for what effectively be nothing.

With a scrunched snout and knitted brow, she whipped around to face him. “I just realized something…”

“R…realized w…what?” he stammered, his voice nearly cracking from stress.

She lowered her gaze, hopped back, and accusatory pointed two fingers at his feet. “What are those?!?”

Peering downward, he cocked his head. “My crossbreed sneakers?”

“Dude, you can not wear those scuffed things to a fancy place like the Piccolo Cuoco,” she tutted. “Actually, now that I’m thinking about it, this whole - whatever you’re calling it,” she continued with disdain while flippantly motioning at him. “Yeah, no, we’re going to need to make a pit stop.”

“Pit stop?” Bitsy parroted nonplussed.

“Yeah,” she sighed with no small amount of exasperation. Either out of pity or frustration, she pinched the bridge of her snout. “We have got to get you something more appropriate to wear - for buck’s sake, you look like a nerd.”

Bitsy opened his mouth to defend himself, but remained silent. There were a number of odd things about what she’d just said. First and foremost, he was a bit of a nerd, preferring gaming and whiling away his days online over going out - secondly and just as prudently, her definition of appropriate was perplexing.

Unlike himself, who’d worn a comfy, oversized hoodie and a pair of sweatpants, Dawn’s attire wasn’t exactly what he’d call suitable for being out in public. She looked normal, not outlandish or slatternly in the slightest. Her attire, a sundress and heels, was a far departure from what he’d expected. He’d gotten a pretty good idea of her personality from chatting with her, yet he couldn’t have fathomed she’d be as conservative in real life.

Her bombastic energy was unchanged, her appearance gave him a moment for pause. Online, when she was catering to her fans and viewers, she normally wore something a bit more revealing - nothing overly whorish, although definitely less than what she currently had on. Tapping one foot, she reached out.

As she went to take him by the wrist, he shied back. “I…I don’t have enough money for shopping. If you’d told me that we might -”

“Pfffft,” she cut him off while dismissively waving a hand. “Bits, I got this! You didn’t think I’d ask if I wasn’t willing to handle it for you ~ did you?”

His heart swelled and a genuine smile graced his muzzle. Dawn was many things, a flirt and tease amongst them, but a miser she was not. She had and would occasionally send her friends and followers gifts that could, at times, be quite expensive - then again, considering how many bits she was raking in with her streams and OnlyMares accounts, she had plenty of disposable income.

“And,” she added, trotting around him and stopping at his side, “you might just be able to help me pick out something cute for myself!”

“Really?” he croaked in surprise.

Nodding her head, she shot him a wink. “Mm-hmm! Now are we gonna get you gussied up for our big date or what?”

“Lead the way,” he chirped while extending one arm.

It had taken him no small amount of time to bolster the courage to actually meet her face to face, and now his confidence was burning brighter than ever. Would anything ever come of this little rendezvous with her? Probably not, no, although it was genuinely uplifting to go out on a lunch date with somepony as sexy and fun as her.

Trotting alongside and only slightly ahead of him, she moved through the cavernous central corridor of the mall. The shopping center was gargantuan, one of the largest in Equestria if Bitsy remembered right, although it was one of his first times actually spending any time in it. On previous occasions when he’d absolutely needed to visit the place, he would typically dart in, find the store he was looking for, make his purchase, and leave like he was on a mission. Simply put, he’d never been a fan of shopping - that being said, shopping with a friend, and an alluring one at that, may eventually change his mind on the matter.

Content to nod and only interject if she asked him a question, he happily listened to her prattle on about the games she’d been playing, the trips she’d made recently, and the petty gripes she had about life in general. As crazy as it may have sounded, listening to her in person was as - no, more entertaining that it was when he was attending one of her streams! He chimed in if and when he could, offering insight or sympathizing with her, until she slowed and craned her head.

“Now let’s ~ what?” she quipped, looking back at him while pulling on his arm.

Bitsy stood motionless and stared into the shop they stood before. While he’d fully anticipated being brought to a clothing store, the last thing he’d expected was for her to bring him to a mare’s boutique. Gripped with indecision, moments from telling her she might have more luck by herself, he closed his eyes.

“Nothing,” he muttered.

Plastering herself to his side, Dawn hugged him. “If it makes you feel more comfortable, we can pretend that you’re my coltfriend…”

Coltfriend - for such a simple word, it held unfathomable power. Maybe he’d been wrong - maybe they could eventually become more than just friends. He wasn’t going to hold out hope for dating her, although the prospect of being friends with benefits proved wildly inspirational. As the fires of his determination roared into an inferno, fueled by hope and the possibility of what may come, he locked arms with her and strolled into the shop.

“Well look at you,” she laughed, “acting all studly with your cute little marefriend! Hey, Trish!”

“Hey, Dawn,” an employee shouted back.

Slipping her arm free, Dawn hastily retrieved a basket by the entryway and motioned for Bitsy to follow. “I’ve already got a few things in mind, if that’s ok.”

“Of course that’s ok ~” Bitsy snickered, “why wouldn’t it be?”

Dawn rolled her eyes as she came to a stop by a display of skirts and garter belts. “Some stallions aren’t comfortable doing this kind of thing ~ can you believe that?”

Shaking his head, Bitsy lied through his teeth. “N…not at all! I guess they’re insecure or something.”

“Right?!” Dawn exclaimed while continuing to browse and periodically pluck articles from shelves and racks. “Honestly, I think you’re right.”

Bitsy watched in awe as she picked items out one after another. Considering she knew one of the employees, and just how familiar she was with the layout of the shop, he had to assume she was a regular - heck, it was almost like she had the entire place memorized. Trailing along behind her, he was led through a circuitous path through the store and ultimately to the very back of the venue.

Glancing into her basket, Dawn bit back a giggle. Bitsy probably - definitely didn’t know what he was in for, but she’d been waiting months for this. He was short, soft-spoken, cute as a button, and everything she’d hoped he’d be. While she had no intention to do anything outright mean to him, genuinely liking the timid little guy, she wasn’t above pushing him to see how far he’d go to indulge her.

She extended one arm to the changing stall she’d stopped beside while offering him the basket. “Personally, I’d go for the fishnets with the matching skirt and top.”

His reaction was nothing short of priceless. As his shocked eyes shot between her and the proffered clothes, her heart began to race. It may have been a little questionable to put him on the spot, although it wasn’t her fault that he hadn’t asked who she had been doing the shopping for.

“Or maybe the - you know what,” she huffed, placing the basket in his hand and closing his fingers around its handle, “surprise me.”

“I…I…” he stammered while she traipsed behind him and started pushing him into the booth.

“You’ll be fine,” she giggled. Seeing the downright fearful look in his eye as he peeked back at her, she relented. “Look, how about we have a bet. If the employees in here don’t think you’re passable as a mare, I’ll buy you anything you want in the mall.”

His expression wavered. “Anything?”

“Anything,” she sternly repeated. “A new game console? Sure. Gaming rig? You got it. Some of those Battle Axe miniatures that cost an arm and a leg? They’re yours.”

He held the basket to his chest and pursed his lips while he turned to face her. “What if I can pass as a mare?”

Dawn had hoped he wouldn’t ask, although there was no avoiding it now. “If you pass, which I’m totally sure you won’t, we’ll continue our trip and eventually have lunch.”

“Eventually?” he repeated, gulping.

“I mean, yeah,” she chuckled. “I’m still planning on getting you some new duds - like, good ones that you get to pick out.”

“Promise?” he pressed.

“Cross my heart and hope to fly,” she solemnly stated, going so far as to draw an X over her bosom with a finger. As he turned his back to her, she gave him a small pat on the tush. “Atta colt!”

The moment the door swung shut and locked, she clamped a hand over her muzzle. This was almost too good to be true - almost. Not only was she already having a blast with Bitsy, but she was finally going to see what he’d been hiding from her. Most of her followers would practically bend over backwards to send her selfies, and a few did so literally and without her asking, although he’d politely shot her down every time she broached the subject with him.

She knew what he looked like before he’d arrived at the mall - sure, although every picture of himself he’d sent her had been remarkably modest. Billowing shirts, baggy pants, and sweaters seemed to be everything he had in his wardrobe, but she was going to fix that. Maybe he had a rock hard, adonic body, or perhaps he had a slender, feminine physique - either way, she was moments from finding out.

Waiting a few minutes, far longer than he needed, she gently rapt her knuckles against the door. “You didn’t die in there ~ did ya?”

“N…no,” he softly replied.

She held her breath for a moment, hoping he’d come out, then ran her hand over her face. “Well don’t leave me hanging, dude! I’m on the edge of my seat waiting to…”

Falling silent, she inched back in wide-eyed wonder as the door gradually swung open. Gone was the modestly dressed little stallion - in his place stood a downright slatternly little femcolt. Holding one hand over his crotch in a desperate attempt to keep his exquisitely short skirt covering his loins, he kept his eyes on the floor.

“Sweet Celestia,” she breathed, genuinely taken aback. “You look -”

“Stupid,” he grumbled, his face a vibrant red.

“Amazing!” she quickly and enthusiastically corrected. “Bitsy, I’ve seen some cute colts in my day, but holy heck!”

She gave herself a moment to drink him in. His top tightly hugged his deliciously flat chest, the fishnets ever so slightly pinched his plump thighs, and his skirt - stars above, his skirt wasn’t covering much of anything. Too eager to control herself, she leaned from side to side while inspecting him.

“Gimme a little turn,” she urged, pining to get a look at his backside. Glancing up when he didn’t budge, she noticed the look of consternation on his face. “For me, pleeeeeeeeease.”

With a pained sigh, he reluctantly spun in place. A more prudent mare may have asked him to get an up-close view of his tush, although she wasn’t feeling particularly prudent. Squatting down and gazing squarely at his rump, practically swooning at the sight of the thong entombed in the cleft of his ass, something peculiar caught her eye - rather, a lack of something caught her eye.

“Hold up,” she whispered. “Are…are you a mare?”

Tensing from head to toe, he whipped around and threw himself back against the wall. “N…no!”

Dawn hadn’t been able to see it perfectly, what with his legs barely parted, although there had been a distinct lack of bulge at his groin. Most - heck, every stallion she’d ever seen wearing a banana hammock had their dangly bits neatly cradled in the sheer fabric cradling their junk, although Bitsy didn’t. Undeterred, she shuffled forward and reached for the front of his skirt.

“Just gotta…” she hummed, brushing his hand aside.

Either too terrified to move or in a state of abject shock, he gave her no resistance while she lifted the front of his skirt. A sense of confusion immediately gripped her as attempted to process what she was looking at. There was a bulge within his panties, but it was downright minuscule - almost nonexistent.

Hearing a whimper from above, she came to her senses and retreated. “Dude, is…is that…”

“I’m…” he rasped, his voice barely a whisper. “I’m just s…small.”

His admission confirmed her suspicions in a heartbeat. She’d heard about stallions who were underendowed, having equipment that was ineffectual at best or pathetic at worst, although she didn’t view their lack of girth as a curse - on the contrary, she considered it a cherished, practically saintly gift. Clamping her eyes shut, she drew a deep breath, held it for a moment, then slowly exhaled to calm her frazzled nerves.

There were any number of things she wanted to do, not the least of which was ripping his thong off with her teeth, but she’d have to play her hand cautiously. Bitsy was clearly on the verge of panic, likely mortified that his friend had uncovered some self-imposed flaw of his, and the last thing she needed to do was to make the situation worse. As she slowly and cautiously wrapped her arms around him and pulled him into a hug, she sighed.

“Bitsy, there’s nothing wrong with that,” she quietly noted while stroking his back. “If you promise not to tell anypony, I’ll let you in on a secret.” Backing away, she locked eyes with him. “I like it…”

It was faint, so subtle that even he might not have been aware of it, but the corners of his lips turned up. “You mean that?”

“Totally,” she insisted. “I won’t force you to come out, but I’ll tell you this much - if, and that’s a big if, we go through the mall with you wearing that, you’ll make my week.”

He only hesitated a moment, the inner turmoil he struggled with shifting under the weight of her kind words, and placed a single foot outside the stall. His first timid step was followed by a second, then a third and a fourth, until he was standing just beyond the changing area. There weren’t that many customers around, only a small handful, although the only one paying him any mind was the mare behind the checkout counter.

“Ready?” she faintly inquired as she stepped around to his side.

“Y…yeah,” he wheezed after collecting his old clothes.

Trotting ahead at a leisurely pace, she guided him to the register. Trish, the mare at the counter, wasn’t exactly a friend, although she was nice enough to give a candid opinion; if there was anypony around she trusted to give honest thoughts on Bitsy’s new look, it would be her. As she clutched her purse and sat it by the register, the clerk’s focus lay solely on the cute, dubiously dressed stallion in disguise.

“You know, I’d normally say something about a mare pulling off such a bold ensemble, but you really pull it off!” Trish noted while extending a hand. “Got the tags, hun?”

“I got it,” Dawn interjected. Listing to one side, she pulled the tags from the various pieces of the outfit. “She looks good ~ right?”

Nodding and grinning from ear to ear, Tish snatched the proffered tags from Dawn’s hand. “Without a doubt! Just be careful out there, cutie, because you might have to beat off stallions with a stick!”

Chuckling to herself, Dawn snuggled up to Bitsy’s side. “Not when I’m around, she won’t!”

Bitsy watched the exchange and kept his mouth firmly shut. He’d fully anticipated the mare to laugh at him or ask what in the world he was doing, yet she did neither. Reeling from the interaction and the possibility that he wasn’t as studly as he’d once thought, his mind tried and failed to make sense of everything that was happening.

Strolling beside her, once she’d paid for his new duds, he faltered at the store’s exit. “W…where to next?”

“You tell me, hot stuff!” she guffawed. “Anywhere in particular you want to go?”

There really weren’t any shops he’d been planning on visiting, although a bright neon sign opposite and slightly down the causeway captured his attention. “Is that a Prancers?”

Peering down the corridor, she nodded. “Sure is! Dude, they always have the coolest swag! Wanna go see what they’ve got?”

“S…sure,” he replied.

He kept pace with her while holding her hand. Prancers was a unique store, having everything from novelty garbage to adult products, and it held a special place in his heart. It wasn’t all that long ago when he’d been in high school and visited a similar shop in his old hometown on a regular basis, and he’d be lying if he said he wasn’t curious to see what sort of goodies they’d stumble upon.

Drifting into Prancers, he marveled at the array of merchandise. It wasn’t exactly the same as the store he used to go to, but it was close enough to tickle his nostalgia. He started when Dawn let go of his hand, dashed to the very back of the place, and waved for him to follow.

“These always trip me out,” she snickered while pointing up at a number of dildos on display. “Do you think ponies actually buy these things from here?”

Bitsy shrugged and cast his eyes down to the floor. “I wouldn’t know.”

“Hey,” she continued, snatching one of the smaller toys from a shelf, “I bet you’ve got this one beat.”

“I…” he trailed off. “Not really, no…”

Placing the floppy little length back on its perch, she grabbed an even smaller novelty dong. “Ok ok ok - I know you’re bigger than -”

“No,” he groaned. “If you gotta know, it’s smaller than any of those…”

Dawn lowered her hand, stood on her tiptoes, and hastily surveyed the shop before leveling her focus back on him. “This is gonna sound weird, but can I see it?”

“Here?!” he bleated, askance.

“Why not?” she countered. “Nopony else is in here, the mall is pretty dead at this time of day, and it’s not like the lighting in here is the best.”

All of her points were valid, although that did little to assuage his concerns. If they got caught, they could get in deep, deep trouble - nevertheless, her charisma and zeal were infectious. Wandering to the far back corner of the dimly-lit shop, keeping a watchful eye over his shoulder, he pulled his skirt up with one hand while tugging at his panties with the other.

“Make it quick,” he murmured.

Practically tripping over herself while scrambling around in front of him, Dawn fell to her knees. The instant she got an unabashed view of his goods, her jaw nearly hit the floor. He hadn’t been pulling her leg about his size - if anything, she’d been led to believe that his package was bigger than it actually was.

Small didn’t begin to describe his goods. With a positively dainty coin purse, appearing like a pair of marbles within a fuzzy little sack, he was sporting maybe - maybe a solid two inches of length. Unable to contain her mirth, feeling as though she was walking a tightrope between insanity and glee, she stifled a laugh.

“No wait,” she asserted before he could cover himself. “I like it - like, I really like it.”

She darted in before he could move. In a word, his equipment was adorable, like a foal’s finger, and it - wait. Gnawing her bottom lip, she exhaled as a revelation dawned on her. She’d assumed he was soft, flaccid from embarrassment, although that was anything but the case.

“You ever popped any cherries with that thing?” she thought aloud before clamping her hands over her muzzle. Peering up at him, she stiffened. His blush had returned with a vengeance, but there was something else - something that hadn’t been there moments prior. Leaning on a hunch, she breathed hotly on his colthood and shivered with delight as a bead of pre-cum formed at the tip of his shaft. “W…who am I kidding, it’s not like you could p…pop a cherry with that if you tried.”

Bitsy made a noise, something like a suppressed moan or whine, although she saw him for what he really was. Though he was acting one way, his body betrayed him. He was as hard as he was going to get, his chest heaved, and his itsy-bitsy - wait…

“Itsy-bitsy,” she mused. “Dude, ok, that is too fitting.”

Staring downward, Bitsy ground his thighs together. He was upset, annoyed, and a good bit fearful, but more than anything he was excited. The thrill that surged through him was as perplexing as it was electrifying, and he honestly wasn’t sure what to make of it. On one hand, a cute girl had her snout a hair’s breadth from his crotch - on the other, he was effectively flashing somepony he just met in the back of a public store!

Running one hand down his hip and to his crotch, Dawn pinched the base of his shaft between her pointer and thumb. “Heh - one finger,” she began, bringing a second digit to his twitching length, “two fingers…”

Simply being touched by her was enough to hammer away at his self composure. He’d gotten off earlier that day, part of his daily rituals before hopping into the shower, yet the pleasing sensations she afforded, paired with her lilting tone, sent him skyrocketing towards release. Struggling to keep his hips from bucking, he remained as motionless as he could.

“Maybe we can get a - awwww,” she lamented, unable to close a third finger around his colthood. “Well, can’t say I didn’t try.”

When she pulled her hand away, Bitsy gave a sigh of relief. If she’d kept that up, there was a very good chance she would have earned an inadvertent facial - unfortunately for him, her torment had only just begun. Swiftly covering his face, not trusting himself not to peek down at her, he covered his eyes as licked her chops.

“In a way, you’re kind of lucky,” she teased. “Any mare you hook up with won’t need any throat game for you to screw their snout.”

Merely hearing her say such a thing drove him wild with desire. Mercifully for him, the carpet beneath him, and anypony in earshot, she didn’t spontaneously test her assertion, although she wasn’t finished yet - not by a long shot. Hearing her shift, he looked through his fingers and balked.

“There we go,” she muttered.

At a total loss for words, he lowered his gaze and balked. Holding the tiny dildo to her loins, she wrapped an arm around his shoulders and touched the toy’s flared head to his prick. The cold silicone didn’t feel nearly as nice as her hand, but having her so close made up for the difference.

Thrusting her hips and tapping the dong against his package, she smiled. “Want me to rub that little clit of yours?”

He did - he really, truthfully did, although this wasn’t the time or place for something so lewd. Flashing her teeth at him, she squatted back down and pressed the toy’s base beside his equipment. The comparison of the dildo to his colthood should have - would have angered him, yet all he felt was exhilaration.

“You like this ~ don’t you?” she purred. “Say it, tell me like having that clit bullied…”

Breathing hard, he averted his gaze away from her face. “Uh…uh-huh…”

“See, that wasn’t that hard,” she smugly noted. “I bet they sell strap-on harnesses here,” she noted, glancing up at the shelves next to her. “If I got you one of those, you might just -”

“Hnnnngh,” he groaned through clenched teeth.

Ropes of spunk shot from his colthood, spattering over the carpet and Dawn’s one arm. The ecstasy of his spontaneous release warred with shame, but there was nothing he could do. A line had been crossed, he’d just made a colossal ass of himself, and he may have just ruined a budding friendship.

Blinking in disbelief, Dawn lifted her arm and looked at the strand of jizz covering it. “Dude…”

“I…I’m sorry,” he squawked. “I didn’t - Mmmmph!”

Dawn bolted to her feet, pulled him into a hug, and muzzled him with a hand. “Sorry! She just got a little embarrassed seeing the adult stuff!”

Glancing over his shoulder, Bitsy felt his blood run cold. At some point or another, likely drawn by curiosity or thinking the two were shoplifting, the store’s clerk had come to the end of the aisle. Lifting his hand and wagging his fingers at the employee, a young stallion by the looks of it, she prayed that the guy wasn’t going to come any closer to investigate.

“That was close,” Dawn groused as the clerk shuffled away. “Dude, warn me next time!”

“N…next time?” Bitsy repeated.

“If there’s a next time,” she quickly added, her cheeks darkening in the dim light. “I got some tissues in my bag. Help me clean up and then we can book it.”

He nodded while stuffing his softening prick back into his panties. They hadn’t been busted, and you couldn’t even see the cum on the carpet, but they’d gotten way too close for comfort. Taking the paper towel Dawn offered him, he knelt down and began wiping his mess from the floor.

It didn’t take them long to clean up, and they beat a hasty retreat immediately afterwards. The good news was that the employee seemed so dead inside that they could have probably robbed the place blind without him caring - the bad news was that Bitsy had crossed a line. No matter what happened now, regardless of what she said or did, he’d never forget unintentionally blowing a load in Prancers.

“I don’t know about you, but all that excitement has me starving,” Dawn cheerfully remarked. Lacing fingers with him, she smirked. “Wanna get something to eat, babe?”

“Does…does that really not bother you - you know, the…” he couldn’t finish as he nodded down toward his groin.

Dawn burst into laughter and shook her head. “Bitsy, dude, this isn’t the first time I’ve seen somepony pop, and it probably won’t be the last,” she responded, hugging his side while they continued in the direction of the food court. “I’ll say this, you are a hoot. We have definitely gotta do this again sometime - if you’re down for it, that is.”

“Of c…course I am - er - would be,” Bitsy hastily choked out, his enthusiasm cutting through his trepidation.

As she gently squeezed his hand, a smile gradually split his snout. Maybe things really were gonna be alright - granted, the euphoria of what he’d just done hadn’t fully subsided, but he felt leagues better than he had. Swinging one arm up and over her shoulders, he pulled her close while thinking about what their next little adventure would bring.