Born to Be Ch. 05

A.N. Back for some black on white! :D

If you want more stories by me look at my profile! All you need to know is there :)

JUST A FUN FACT also, this is not the final chapter, not at aaaaaaaaaaaaall, there's maaaaaany more to come. You'll see why I say that at the end lol, just again letting you know ahead of time, no reason to worry.

The Following Contains: Tall strong black lady making a little white boy her bitch. x3 crossdressing femboy and pegging. Still one of my only futa-less stories.

Enjoy it! :)

*****

Selena really knew how to kick Ashley's booty into gear when it came down to it. Only a few days ago had he come home with an ensemble of girly outfits to start trying on around Selena, and already she had him preparing to wear them in the outside world while they went on a date.

The boy stood now, in the cute underwear he had chosen for this evening, a nice white bra which accentuated his flat chest and gave him the appearance of having tiny A-cup titties under his shirt. And a matching white thong, snugly enclosed around his crotch keeping his boyhood as small as possible and cradling his boy pussy so tenderly.

But the underwear was easy to decide on. It was something only Selena would see so he only had to worry about impressing her. And she did love him in a nice tight thong, so he felt that he was covered in that department.

Only when it came to deciding on the outfit he'd wear that all eyes would be seeing this evening. That's when he had a little more trouble. It was a Friday night dinner date with Selena, Vanessa, and a few other of her friends from work. Mainly to get him out there so that he could start meeting new people. He'd been in the city for about a week now and hadn't really gotten to know anyone aside from his girlfriend and his co-worker.

So this was not particularly a romantic evening with just the two of them, but it wasn't exactly a casual gathering either. The place they were going to was a four-star restaurant with fine table service, open bar and dancing. So it could be considered as formal, but did he really want to break out a high class dress and appear overdressed for something that was supposed to be casual?

He huffed, blowing a lock of brown hair up over his forehead, it grew a little bit longer every day. Something Selena constantly reminded him about, and how much she loved it. She kept tugging on it whenever they had a quiet moment just to sit down between them. It drove Ashley insane, but he also liked it. Quite a bit actually, especially the teasing about how she couldn't wait for her handle bars to fully grow...

Ashley shivered a bit at the thought and focused up. He laid his possible choices for his evening attire out in front of him. Ranging from flirty, to sexy, to classy, and stood over the three outfits with his hands on his hips. Contemplating each with a bare foot tapping on the floor.

There were so many things that he had to factor in to what he would wear, just on how much he wanted to impress Selena with how comfortable he could be in these outfits now that he'd been wearing them for several days now. Even if that wasn't entirely true...But! He also didn't want to upstage any of her friends by trying to look all sexy and flirty!

And God help him if somehow, they discovered he wasn't actually a girl...

"Urrrrg..." Ashley groaned bringing a finger under his chin. "Do I do a skirt? Or...the strapless? No! Nonono, I don't wanna look like a hooker!" Ashley's dilemma resumed, he had one outfit consisting of a cute top with a waist high pinkish-cream colored skirt, another was a long strapless blue dress that glittered a bit around the breast area. And the final outfit was a tank top and jeans...classy. "Gosh how to girls do this?" Before he never worried about outfits, never, of course he made sure he looked good, but now...it was like every outfit while cute in its own right...had some type of drawback to it. Some...thing! That made him shake his head and throw it aside.

Maybe he had gotten too many girly outfits, now he couldn't decide which one to wear and it was driving him crazy!

It was just dinner after all, and nothing extremely fancy. Just a cozy little place with some friends, maybe a little dancing and an evening together to wind down in. Why was he panicking so much over this?

"Okay...come on Ashley...be a man and-...err...I mean...ugh..." He groaned, "What has my life become?" He asked no one in particular as he spun around and threw himself dramatically onto the bed. His light body bounced a little from the soft mattress and he stared up into the ceiling. You think having been dressing all girly like for the past several days would have better prepared him for this, but you'd be wrong.

His confidence had definitely grown a bit, the more he wore them, the more comfortable they became, both literally and figuratively. Girls had some really comfy things to wear, but too many options apparently.

Ashley's head turned to look at one of the options at his side, the strapless dress, then turned his head to look the other direction, the flirty shirt and skirt combo. The jeans and tank top was something he only considered in a last minute act of desperation, he didn't actually plan on wearing them, so he laid on them for now.

Even so, the split decision he had to make was more than enough. As much as he tried to talk it down, this evening was very important. Aside from the yoga clothes outing, he had made very few public appearances deliberately posing as a girl. This was pretty much a make or break moment for this...fetish, he and Selena had.

It either worked and he could pose as a female with the rest of the world being none the wiser, or he'd blow it and feel an insurmountable amount of humiliation.

So his mind drifted to the safer of the two options, the shirt and skirt. If he was caught, with the skirt at least he could take it off and pass the thong off as a speedo. It was a long shot, but at least if the jig was up, he had hope of recovering. If he wore the dress though, it was all one piece, there was no escaping from that.

He shrugged a shoulder, it was a lame way to finally make a decision, but it was better than not making a decision at all. Plus, since this wasn't a one on one date, perhaps it was best that he dressed to impress not just his girlfriend, but the acquaintances she was bringing along.

Ashley sat up off the bed and spun on his heel to look between the outfits again, "Sorry strapless, but maybe another time." He picked up the garment, along with the casual attire and returned them to the space Selena had cleared for him in the closet.

His furniture had still not arrived yet at his apartment, and all his essential belongings had been retrieved from there and brought here while he and Selena bunked together. Although the promise from his moving company that his furniture was on the way did little to deter Selena from constantly teasing Ashley about just moving in with her forever and ever and ever.

He actually rolled his eyes as he hung the clothes back up, she could be so silly sometimes. Although...to be truthful, these last few days of living together had been amazing. They didn't bicker over anything, the cuddles at night were sooooo comfy to fall asleep to. They both loved the same kind of movies and shows on tv, and they worked together now so they could car pool easily.

More than once, Ashley actually contemplated taking her up on that offer...

But no, he steeled his resolve for now, he had yet to prove to the world that he could be fine on his own. And if not to the world, to prove it to himself! That's what his move was for, to show he could be his own person, self-sustaining, and didn't need anyone to rely on.

Only that motivation was drifting further and further from his mind with every passing moment he spent with Selena. His hands trailed down the smooth, silky material of the dress as he thought about it, she was so good to him. She provided everything for him, she cared for him, so pretty, so strong, so protecting...

And how could he forget...the sex was fucking AMAZING.

If you had told Ashley a month ago that he would have some of the greatest orgasms in his life via only anal stimulation, he would have looked at you like you had a thousand heads and laughed. But it was the truth, anal sex was so good...soooo gooooood...

He shook his head, bringing himself out of his day dream about Selena's BBC and exited the closet. The date was in less than an hour, so if he wanted to be ready for it, he needed to get dressed now.

Meanwhile Selena paced steadily back and forth downstairs, jingling her keys between her hands as she impatiently waited for Ashley to get ready to go. She forgot that making Ashley into her girlfriend would come with the drawbacks of girly tendencies. Namely, taking freaking forever to get ready.

This almost made Selena chuckle, but she also felt a nice swell of pride, and happiness in her heart at the thought of it.

Her and Ashley had come so far in such a short time, further than she had ever gotten with any of her previous exes. Maybe that's why she liked Ashley so much, he responded to her in ways that no other boy had. Whenever she revealed her hand about what she wanted when it came to the bedroom, her previous suitors had cut and run. Almost all of them actually...one or two stayed for the strap-on aspect for a while, but were never willing to go beyond that for her. None of them seeming to understand that it was something that she needed. It's just who she was, IS. She didn't want a girlfriend who was a girl...she wanted a boyfriend who liked to dress up as a girlfriend.

And contrary to what you may find on the internet, it's actually much harder to find someone who liked that kind of stuff in actuality. The fit ebony woman had her fair share of heartbreaks with men who weren't able to fulfill her desires, even when she was willing to forgo them for as long as they needed. So many guys just didn't even want to try for her.

For a long time Selena thought she may actually be alone. Not just for a short time but for the long run, she thought it might just be the way her life goes. Her dream fantasy of having a boy who liked to act like a girl, take it up the butt, and play wifey for her may only be that. Just a fantasy.

People probably would've called her crazy, Hell even Vanessa called her crazy. She was a freaking BABE! Tall, long legs, nice feminine muscles, epic tits and an ass you could suffocate in with a smile on your face. She could've had anyone right?

Wrong...very wrong.

Vanilla relationships just...didn't work. It always felt like something was missing with Selena, like she had fun in some of them, but she knew she would never be all in with any of her previous boyfriends. It was just the way she worked, something in her brain wired her to be this way and for the longest time, she dreaded that it might be a curse that forced her to be single for the rest of her life.

But then...there was Ashley...he came along.

The one 'he' who seemed perfect in every way. The he who liked to be called she, who wore pretty dresses for her despite how taboo it was. Despite if it made him blush with nervousness, he did it for her. He was willing to push his limits and go beyond the comfort zone just so that Selena was happy.

It was like a gift from God had fallen right into her office the moment he first walked in. Even now as she leaned against her front door she felt butterflies in her stomach. Usually she was the one to make him swoon, but this was one of the rare times it was the other way around. When she laid eyes on him for the first time her breath was taken away, she could feel her cheeks getting warm as she thought about it.

She wanted him like mad. When he left her office she went straight home and beautified herself as best she could, breaking out the best perfume, makeup and everything. It had been so long since she had drooled over a boy like this, and it only got better when they got to the bedroom.

Look how far they came, she was waiting for him to pick out his girly outfit for their date tonight. Selena's smile grew even more at the thought, technically their second date, but she still felt as floaty as she did on the first one. Ready to seduce the fuck out of the boy she was falling for...

Falling for...

That thought actually gave Selena pause, so much had happened in so little time but...what Selena actually falling in L word with him?

Her eyes went to the floor and she thought about it, was it too soon to think like that? Hell no! People have fallen in love at first sight before and lived happily ever after, so what was one week when it was actual love they were dealing with?

But it could be just that she was over excited about how she was finally getting what she wanted out of a boy. So her brain and heart were telling her to just lay all her cards on the table so that she didn't lose him! Then again though...what if that wasn't true? What if she did just genuinely have strong feelings for him that could be constituted as...love?

"Coming!" Selena's head shot up out of her daze as she heard the voice of the subject of her thoughts. Immediately pushing herself off the wall and straightening herself out. Her attire consisted of sleek black slacks and a hot white top which accentuated her cleavage extremely nicely. Black high heel shoes that made her height even more intimidating than it already was.

She grabbed up her purse and called out, "Let's go babe, girls are gonna be waiting!" And then, she saw him.

Slowly, he descended the steps, wearing his own pair of high heel shoes, only his were like sandals, with his feet showing and straps going around the ankles and between his toes. The skirt and top he ended up choosing hugging his petite body and growing longer hair framing his face beautifully as it now reached below his shoulders.

Her breath hitched and all previous thoughts about her possibly not being in love were out the window. If that boy descending the steps was the subject of her affection, then damn it she was going to own it!

"Okay...I'm ready." Ashley pulled the skirt up around his waist a little more, nerves setting in more than he had anticipated they would as he descended the stairs. Selena had given him over an hour to get ready and the fact that about eighty-five percent of that time was choosing whether or not to wear this outfit was unspeakably embarrassing. So Ashley just decided to keep that bit to himself as his heels clicked on the wood floor.

Almost wobbling as he was still getting use to the elevated feeling and the arched position of his feet while he wore them.

Selena smiled, stepping away from the door. "Nervous honey?"

"Well...yeah." He replied matter-of-factly, "I've never gone out in public in a friggin skirt before." He comically slapped the sides of the fabric making it bounce up and drift back down revealing the white thong he wore beneath. Only for a split second, but that was all Selena needed to get a vivid image of what their evening was going to be like.

She sighed, "Oh come on babyyy..." She started with a pout and approached her 'girlfriend' for tonight. "You look sexy, and cute, and fuckable, and everyone's gonna be jealous! Pluuuus!" Suddenly she ducked down and swooped her arms under Ashley's tiny body.

"Whaa!" He squealed in surprise as she suddenly swept him off his feet and picked him up bridal style. "Selena?"

"You've got me to take care of you." She grinned wickedly as she held the petite boy like a blushing bride. "Let's go! Off to adventure!" She chanted, practically dancing over to the door with him in her arms. Reaching down and supporting him with her forearm to turn the doorknob and exit the house.

Ashley groaned, "You are absolutely insane." He would've squirmed, or whined about being let down. But this wasn't the first time Selena had picked him up and hauled him around like a doll. She did it both inside and outside of the bedroom to both show off how weightless he was in her strong arms, and also he figured just to show off just a teeny bit.

He could've complained but truthfully, it wasn't a bad feeling. Being lifted into someone's arms, under their protection and in their comforting grasp. Plus...he liked the idea that his weight was so little in her hold that she could easily manhandle him however she wanted and wouldn't break a sweat.

It was sexy...Ashley couldn't deny that. So rather than kick and whine and ask for freedom, he allowed his ebony Goddess to carry him like a trophy wife to the car, she even managed to open the car door and set him down inside without releasing him from this hold. After which she ran over to her side and got in the car as well, eager to drive off to the location of their planned date night!

Said location, was a nice cozy four star bar and grill. The glowing sign above the main entrance read, 'LoJo Diner.' Selena revealed that this name was actually the first initials of the owners mixed together, Louis and John. A couple married for fifty plus years and owners of the restaurant for almost the same amount of time.

No wonder it was such a nice place, it had been going strong and in the same family for literally a generation.

It was well lit by dangling glass lights in the ceiling, multiple polished wood tables and booths lined the walls and corners of the establishment along with a long ninety degree angle bar with dozens of stools to sit on in front of it. Soft music played to a steady rhythm as the couple entered and Ashley scanned about. Clinging onto Selena's hand the entire time for dear life.

In the center of the room was a shiny wooden floor that a few stragglers of people were actually dancing on currently. Not many, a couple or two and just a few other randoms enjoying the tunes. Behind the bar was a long rectangular window that you could see into which lead to the kitchen, and an array of delicious scents wafted from there of freshly cooked meats, steaming veggies, hot foods that could make a vegans mouth water.

At the entrance, the two were greeted by a hostess dressed in a simple yet sweet button up blouse with the title of the restaurant stitched over the left breast pocket.

She welcomed them with a smile, "Hi welcome to LoJo's! Table for two?"

Selena returned the smile and approached, "No actually, reservation for Mills please? Party of six?"

The hostess looked down at the podium by her, and started swiping along what looked to be an integrated tablet of sorts. Meanwhile Ashley continued to do his best to just cower behind Selena, glancing about the restaurant to see how many eyes he had to deal with tonight.

He was fully gussied up! Selena and Vanessa had helped teach him some basics of makeup and the like, his nails were freshly painted, there was a little extra blush added to his cheeks along with some eyeliner to accentuate his eyelashes. And a light layer of lip gloss coated his pretty pink lips to make them shiny, he even wore the sweet perfume he got as well. Full on disguise! And tonight was the ultimate field test to see if it worked.

Glancing about the restaurant, it looked as if there were maybe thirty...thirty-five people attending tonight? It was hard to get an exact head count at the rate that Ashley's brain was going. "Okay...okay keep it cool. Act like a girl...act girly...no one will know! And I don't even recognize any of these people anyway! No one here knows me, I'm not even from this town it'll be fi-OH GOD THAT PERSON LOOKED AT ME!" Ashley mentally panicked as he saw a man in a cowboy hat just glance by his direction.