Born to Be Ch. 03

She also knew all about Selena's fetishes and what she wanted in a man for a long time, and she knew her girl was fawning over this boy and hoping against hope that he was the one for her. And Ashley seemed like he was tempted to take the dive into this crazy world of gender bending fun that Selena had such a good time with, but he was teetering over the edge with uncertainty. Like he just needed that teeeeeeny tiny little push to send him spiralling into it with her so they both could just go all out and have fun together.

"Hmm...I'll tell you what." Vanessa began, "On my lunch break, you come with me to the mall." His head lifted to meet her eyes, "I think I have an idea that'll really help drive what I'm trying to explain to you home. That based on what I see in front of me now and what I've seen with her, that I think you two are perfect for each other." She swiveled in her chair to be face to face with Ashley. "So let's go do a little shopping, and we'll pick up a surprise for Selena, and I can drop you off at her house and send her there immediately after."

"But how will we do that? I don't have a key to her home we just started dating." Ashley said, his nervous disposition already trying to poke holes in her plan.

"Oh I know where that bitch hides the spare." She chuckled, "I told you, known her for a long time." She continued, "But if you trust me on this, you'll see just how much you're perfect for her, and she's perfect for you. One look at you and I know no other guy would be able to fulfill her fantasies like you can. And if you prove that to her, she's all yours baby, and you can be all hers." She sounded very genuine, "Plus, I think this'll help you come to terms with what you want, if you just let me take you for a little mall escapade. What do you say? Sound like a plan?"

Ashley considered her offer for a few moments, glancing up to Selena's office and back down at the curvaceous brunette in front of him. What was this plan of hers? He didn't know, but Selena told him earlier that he could trust this girl. And if Selena confided in her as much as Vanessa claimed she did, then odds were she knew what she was talking about.

Besides, what else did he have to lose at this point?

So he took a deep breath and blew it out his pink lips, "Promise me it's not gonna be a thong?"

Vanessa burst out in a giggle fit at that, "Noooo, no, I'll save the thong buying for Selena. I have something a little...cuter on my mind." She said with a sadistic smirk, again chilling Ashley's bones.

Just then, after a long period of no customers at all, finally someone entered through the glass entrance and turned to log in at the desk. "Oh! Here we go, let's show you the ropes rookie." Vanessa cheerfully said, sliding her chair into place.

Downtown Mall: Noon

The hours rolled on and eventually the clock called for Vanessa to take her lunch break, which meant that Ashley had to as well. She of course notified Selena of this with a text, then took the young trainee out of the Lunar Lifters fitness center and out to her little cream colored Audi car in the lot. They only had an hour for lunch before Vanessa had to get back to work so they scurried around the building a little to make it, before hopping in and driving straight for the mall.

She taught Ashley the few ropes that were required for him to man the desk as well in the hours leading up to this, but truthfully, there wasn't much to learn. A lot of point and click, occasionally scribbling something, and plenty of 'smile and have a good workout sir!'

Even Ashley was a bit underwhelmed by the amount of things he learned. He almost didn't want to believe that she was telling the truth, that there had to be some kind of catch to this position. He'd have to log hours, or right down a complex membership code or something. But nothing came up at least not yet, and he figured he'd have to interrogate Selena later about it.

But regardless, they now practically burst through the doors into the downtown mall, being very mindful of the clock as this was a race against time to get everything in order. "Okay so this way! We've only got fifty minutes before I've gotta be back at my desk so hurry!"

"I'm coming!":Ashley nearly had to jog to keep up with the enthusiastic receptionist. Whatever this idea was, she was extremely excited about it. "I'm not a runner!"

"Oh and I look like one?" Vanessa fired back, gesturing to her curvy body, clad in a cocktail dress and heels.

Ashley shrugged sheepishly.

Vanessa led Ashley through one row after the other, eventually reaching the clothing section of one of the many stores they passed. Ashley felt a bit of relief when he realized they weren't going to the same store that Selena took him to before. But that relief quickly turned into a bit of morbid curiosity as to what exactly was she doing when he realized something. Never once did she even glancing in any of the boys sections, so Ashley just assumed that maybe they weren't shopping for him yet. Maybe Vanessa had to pick something up for her in order for this plan to work.

Eventually stopping by a rack with numerous cool colored sundresses hanging from it. She seemed to quickly hone in on a particular purple one. "Oh my gooosh look at this! Yes! I hoped it would still be here. This'll look amazing!"

She said. Ashley smiled at the giddiness she showcased as she picked up the garment, it's colors changing from a lighter purple at the top, to a darker color as it went towards the bottom. The skirt was ruffled a bit and the straps for the shoulders were bare minimum thin. A very cute piece of women's attire, but then realized something. Not to be mean, but Vanessa was on the plus side with her body type.

And that dress was faaaar too small to fit her...

It was at that moment that the clouds opened up and God said, 'this is your destiny Ashley' as Vanessa turned to him and said, "Try this on!"

"Oh come on!" Ashley whined, "That? Are you serious? The yoga clothes was one thing but that's straight up for girls Vanessa!" He backed away a few steps, immediately regretting agreeing to follow through with this plan.

"Did you not hear me back at the gym Ashley?" She countered, "I told you your girlfriend as a very specific fetish that both of you seem to enjoy at least based on her rave sex reviews of you. But you're still holding back from that extra little push that the both of you need to really kick the start of this relationship into something awesome! Come on let me be matchmaker here! Oh...and we'll have to find some cute matching panties to, I did promise no thongs so...cotton or lace?" She bounced a little bit like an impatient child with the dress.

Ashley waved his arms out at his sides, "Does the world not understand I'm a boy!? I'm really at a loss here, like..." He fanned his fingers through his long hair, "I get that she can have a fetish, there's nothing wrong with that but...I'm...I'm not sure I can..."

Vanessa cut him off, "Ashley, the world is not what we're dealing with here. We are dealing with your woman!" She pointed a finger at him, "And your woman likes you in tight and girly clothes, you don't seem to sure about whether or not you're ready to jump into something like that, but I think you are. So I want you to just try this one time, for me and for Selena. And if you hate it, can't stand it, wanna rip the dress off then fine. That's all that's required, we'll never bring it up again and I'm sorry I was wrong." She rambled a little, but continued, "However, if I'm right, and you and Selena share this same fetish and sexual appetite, then you were Born to Be together! And you can thank me later!" She rationalized her plan and held the dress out with her arm fully extended.

Ashley let out a deep sigh, and looked over the dress. It was his size, would probably fit nicely. And if Selena liked girly clothes on him then...maybe just one try would do no harm. Maybe if it made Selena happy then...maybe he could deal with it.

His hand dramatically snatched the dress in one hand. Pouting his mightiest of pouts at his fellow receptionist to convey his dissatisfaction. "I'm not happy about this."

Vanessa cupped her hands under her chin romantically, "Oh the things we do for love."

A few minutes and a changing room that was the least visible to the public eye later, and Ashley was ready to emerge. Vanessa standing outside waiting eagerly to see the fruit of her plan coming to reality.

Ashley removed his shoes and socks so he was barefoot and bare legged as he stepped out of the changing room. The purple dress fitting him, absolutely perfectly, the purple color accentuating his softly toned skin, and showing off his smooth, blemish free shoulders and legs. Even from the front now, it would be easy to mistake Ashley for a girl while he was wearing this.

"Oh...my Gooooosh!" Vanessa squealed while Ashley just stood their sadly in her gaze. "...you are keeping that, I'm buying it. You can say nothing to change my mind! This was a brilliant idea, this is happening!" Vanessa blabbered out as Ashley emerged from the changing room.

His face wore an expression of horror and defeat, trying to remind himself of what Vanessa said. The things we do for love, but again he groaned pitifully, "You've gotta be kidding meeee? I can handle all the yoga clothes, I can understand my girlfriend has needs and desires and such but I mean...THIS?" He dramatically grabbed the skirt of the dress and yanked it about slightly. Unknowingly flashing Vanessa a little glance at the light purple panties he had on underneath it. Vannessa had snatched those up on their way to the changing room and was happy to see he actually tried them on rather than wearing his boring normal undies beneath it.

She tried to tempt him with some white stockings that went up to his thighs and a cute pair of sandals with butterflies on the straps, but Ashley managed to refuse that. Along with the cute ribbon that would be tied into his hair, he was trying the dress and the panties alone, and that was more than enough for one day.

"But it looks so cuuute!" She gushed, "Selena is gonna love to see you in this!" The purple sundress only went down to juuuust above his knees, and the thin straps up top were barely visible on his bare shoulders. No bra underneath which did nothing to help hide his hard nipples.

"Vanessaaaaaaa..." Ashley whined, "This is embarrassing!"

She put her hands on her hips, "Oh come on, are you gonna tell me you don't like how it feels wearing such a silky, soft dress?"

"Stooooooop..." He whined again, looking down at the dress and what he had become. "Are you sure Selena is gonna like this?"

"Yes! Absolutely!" She said proudly, approaching Ashley and reaching out to take hold of his wrists. "You like Selena don't you?" He nodded, "Then you've gotta trust me on this, I know this is crazy, and I know it's definitely not how you probably pictured how your relationship would be going when you first met, but I know this will work. And if both you and Selena are happy, then that's all that matters right?"

She seemed so passionate about this, she must really care about Selena's happiness. He barely knew this woman, heck truthfully who was only just getting to know Selena too, and look at the incredible lengths he was going to try and make her happy.

Maybe that was a sign itself that Vanessa was on the right track with this plan. He looked down at the dress on him again, swaying his form back and forth just a little bit so that the skirt swished with his movements. It wasn't uncomfortable, not at all actually. And the panties under it, they were sooooo soft. And quite adorable, when he slid them up his legs and looked over his shoulder into the changing room mirror, he almost got aroused looking at his own cute butt in them. They covered more of his cheeks then the thongs did, but only just a little.

So maybe, just maybe all of this wasn't as bad as he was making it out to be. Maybe if he gave it a good old college try, maybe he'd find some happiness in a place he never knew to look.

He breathed a slightly shaky breath, then glanced back up at Vanessa, "Okay...what do we do next?"

Vanessa squealed in happiness, excited beyond belief at how Selena was going to react. "Yes! Okay we don't have much time, let me pay for this and get you back to the car. I'll text Selena when we're on the way to give us juuust enough of a head start."

Ashley nodded "Okay, and what am I supposed to do...just wait for her?"

"Yeah sure!" Vanessa nodded happily, "I mean, I think it's pretty obvious what she's gonna do the moment she sees you in this." She playfully poked Ashley's belly, he instantly grimaced and shied away from her touch, still being pouty. "So, since you know she's gonna be coming for that booty, I'd recommend maybe striking a pose on her bed, oooor maybe giving her a little twirl in the dress when she first sees you."

"Ugh..." The tormented boys shoulders fell, "I really hope you're right about this."

She waved her hand, "Honey, I've known this would work since the moment the two of you walked in together." She took out her phone, "I've got an eye for this stuff, I can usually just tell when two people truly are born to be together."

Selena's Residence:

Selena read the text over again, 'Your baby girl has a surprise for you at your house ;) go get her bitch!'

She pulled into her driveway, and put the car in park, looking over her shoulder at the cream colored Audi vehicle she recognized as Vanessa's speed by her down the road. She must've just fled the house in time to not be there when she showed up.

"What the Hell are you planning you devious slut?" She mumbled to herself as she exited her car, then marched with a purpose up the walkway to her front door. Apparently, Ashley was inside with some sort of surprise, and Selena's mind went wild with a multitude of possibilities as to what it could be.

Did Vanessa suddenly turn even and beat the shit out of Ashley and drop him in Selena's bathtub? Did she cheat with Ashley and leave him tied to her bed? Naturally the worst scenarios popped into Selena's head first before the more realistic ones did.

"Oh relax you spaz, she probably just gave him like a goofy shirt or sent him home with a cake or something for me." She tried to rationalize.

But it still made her seriously regret telling Vanessa where her spare house key was, and she reminded herself to either move it or to change the locks whenever she got the chance. Or maybe a keypad, she'd been meaning to install a security system into her home so that would definitely keep that bitch and her antics out.

She made it up her steps and yanked her keys from her purse, then unlocked her front door and quickly entered her house, "Ashley? Baby?" She called out shutting the door behind her. "Are you here?" She took a few steps into the living room, looking around to try and spot him. Throwing her purse over by the sofa uncaringly.

But before she even made it six or seven feet into her house, she heard the tiny, familiar voice of her Ashley softly speak, "Yes...I'm here..."

Instantly she spun on her heel to turn and see Ashley, peeking shyly out from around the corner that lead into the downstairs bathroom. She could only see one of his hands holding the corner of the wall, his hair and his eyes looking at her. She sighed in relief at the sight of him, "Hey baby!" But then realized that he appeared to be hiding behind the wall, "What are you doing over there honey? What's wrong? Are you okay?"

"I am...I'm okay...I just uhh..." He cleared his throat. "I have something to show you..."

"Oh...okay?" Selena looked very curious now, "Show me what?"

There was a pause after that as Selena tilted her head curiously at her young boyfriend. She could already see the redness in his cheeks reflecting on the white wall paint from here. His baby blues glanced nervously down at the floor one last time before he steeled himself. "Okay...do it for love."

Carefully, Ashley moved one lead filled foot after the other, his bare skin tapping on the cool wooden floor beneath them as he began to step into view of Selena. Moving away from the protection that the wall offered and revealing his feminine attire, no pants, no shirt, no bra, just the dress and the panties underneath it.

His heart was hammering as he walked to his destiny, shyly tilting his head up to look Selena in the eyes as she bore witness to him for the first time dressed like this. His own doe like eyes sparkling in the light of day, she watched them and him move shakily closer to her.

Selena slowly let her eyes wander up from the bottom of her boyfriends bare feet, up passed his smooth, soft calves and thighs, completely bare and exposed to her, up further to the frilly purple skirt section that was attached to a dress. Changing shade from a dark purple at the bottom to a lighter hue at the top by Ashley's chest. Two straps held it in place over his shoulders and at the tip top was Ashley's nervous blushing face, framed by his heavenly locks of brown hair that went nearly to his shoulders. His eyes glistening and scanning her just as she looked over him, searching for any form of reaction that he could glean.

Up until he had enough space away from the wall to swallow the lump in his throat, he gathered as much resolve as he could and tried to ignore any ounce of pride or shame he may have still remaining within him. Then quickly, almost so quick that if you blinked you might miss it, Ashley was standing on one foot, and with a graceful kick, he did a quick three sixty twirl.

Spinning around in front of Selena so she got to see the full dress, his skirt swirling with him and showing off just a tease of his creamy thighs concealed beneath it. Stopping and landing perfectly back on his two feet and swallowing a second lump that threatened to come up in his throat. Selena watched with wide eyes, in shock, confusion and...a bit of amusement as well at this display seemingly coming from out of nowhere.

When she didn't say anything, Ashley started, "I...thought you might like a twirl..." Quickly adding, "Vanessa made me promise to do that." After finishing the twirl, practically mumbling the sentence incomprehensibly under his breath.

He then stood their, hands folded in front of him, and waited to hear her opinion. Nervously twiddling his thumbs and trying to maintain eye contact with his beautiful girlfriend.

The amount of time that passed in silence, with no reaction from her was putting Ashley through physical pain. She just stared at him, lips slightly parted with a barely noticeable ghost of a smile at the edge of her mouth. Was she about to burst out laughing? Was this whole thing an elaborate setup? He didn't know, but waiting for her to say something was absolutely killing him. Did she like this? Was she about to kick him out on the street and out of her life forever? Just what was she going to do?

Thankfully it didn't last forever though as Selena finally said, "Wow...so...I take it Vanessa put you up to this?" She asked, resting a hand on her hip, cocking it to the side while her eyes continued to check out Ashley. Seeming to appreciate this new look he was sporting.

Ashley nearly scoffed at the mention of this being Vanessa's plan, "What gave you that idea?" He tried to joke, feeling that maybe a little humor could help alleviate his humiliation.

"Well..." She began as she slowly looked Ashley up and down once, twice, three times more, openly molesting him with her eyes. "She's got great taste."

He blinked up at her, "Wait...really? You think so Selena..." Ashley replied, his hands fiddling with the front of the dress, "I mean...Yoga pants and the underwear...that's one thing but...I just...I wasn't sure about this." His eyes stayed on the floor, "It's just...for one thing it's embarrassing. I mean, I'm a boy...I must've said that a million times over just the last day and yet it feels like it just goes over everyone's heads. I'm not supposed to dress like this...but, Vanessa told me that you liked this kind of stuff? So I thought that...if it was for you I could maybe..."