Born to Be Ch. 04

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Ashley tumbles further into girly habits.
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Part 4 of the 12 part series

Updated 10/06/2023
Created 03/07/2019
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A.N. Back at it again with the interracial pegging!!

Thank you all as always for your patience while these chapters come out! And thank you a huuuge amount to my supporters! :3333 you guys make it so I have food on the table and can keep doing what I love!

The Following Contains: Black Amazon Woman on little girly white boy who is progressively becoming girlier. x) Oh and she sticks a strap-on up his booty a lot.

Read it and fap!

*****

"I can't tell you how much it means to me that you're doing all this just to make me happy." Selena smiled behind Ashley, the two of them looking into his reflection in the mirror. "Ugh, just look at you! Sooooooooooo cuuuute!" She gushed.

Ashley kept the dress on for most of the day yesterday, but like a fool, allowed Vanessa to bring him here without any other clothing options aside from the dress. His normal boy clothes were in her car when she dropped him off and she drove away with them. So now he was faced with only the option of wearing something Selena had on hand.

Which consisted of plenty of yoga outfits.

"Ehhh...I don't know...I'm still not sure." Ashley blushed at his reflection. Wearing the rather girly outfit Selena picked out during the yoga shopping. The yellow blouse and tight black yoga pants showed off the amazing feminine figure he sported. Whether he was proud of it or not. After last night, the whole purple dress fiasco, Selena had managed to talk Ashley into trying on another girly outfit and wearing it not just for her. But to actually put it on and wear it the whole day while they both went to work. "I mean I'll happily do it for you but...other people seeing me it's just...what if they think I look stupid."

"Ohh baby." She hugged him from the side, "First off thank you again, thank you so much for trying these things out for me. And second, it doesn't matter what anyone else thinks. I think you're so beautiful." She kissed his cheek. "And sweet." Another smooch.

And another, and another. Kissing over his forehead and face.

It was only the morning after Ashley first dressed like a girl so he was still a little insecure about doing it more, especially outside of the house. So Selena figured a little reassurance couldn't hurt when it came to convincing him that it would be worth it.

Ashley squeezed one eye shut and started to giggle. "Selenaaaa, hehehe! Stoooop..." He playfully protested to no avail.

Smooch smooch smooch smooch "Aaaaand cute!" Smooch, "Aaaaand pretty." Smooch, "And sexyyyy" Smooch smooch.

"Okayyy! Okaaayy I get iiiitt!" Ashley feebly struggled in Selena's incredible hold, obviously no match for her epic grasp. But he truly didn't want to escape her anyway, it was just like a little playful wrestling bout between them.

"Mmmmwah! Plus, the more you wear these cute clothes, the more use to them you'll get. And besides, I think we both know that anyone who sees you dressing like this, will think you're sexy as fuck baby." Selena finished her kiss assault and simply held Ashley in her arms.

He rolled his eyes, "Nah uh."

"Yeah huh!" One last quick peck on the lips that made Ashley blush. "Plus, if you grow your hair a little longer, ooouff...baby you're gonna have people trying to steal you from me."

Ashley smiled, "Well too bad for them, I've only got eyes for you...Daddy." He said, still testing the waters a bit with this new pet name, but finding himself liking it more and more every time he said it.

It also appeared that Selena was also developing increased affection for that term as well, considering she bit her lip upon him saying it. "Nnnf, baby girl...you might wanna hold off on calling me that if we wanna get to work on time." Her arms drifting to a lower point on his body, searching out the booty barely contained beneath those yoga pants and grabbed both cheeks hard. Squeezing the plush flesh, showcasing her obvious desire to take him again.

He giggled a little at her comment and grabby hands, but he couldn't deny, that being called her baby girl...it was so naughty. So taboo and forbidden that it excited him to no end, both in the ways of making his heart flutter and his belly flip. It was cute and protective, while at the same time dirty and lustful.

When all of this started, he wasn't sure if he could handle Selena's antics and her acquired tastes in the bedroom. But now, she seemed to be successfully swaying his opinion to be in favor of those same tastes as well.

She was right though, if they wanted to make it to work on time they couldn't spend a while in the bathroom fooling around. "Okaaay, okay, okay I'll hold off." He tried to lean away from her, "You're right we gotta go, now unhand me you vile beast!" Playfully he batted on her, trying to squirm free of her hold.

She didn't let go for a few seconds, still growling with a wide toothy grin for a few more moments before she relented enough for him to break free. Clearly wishing she didn't have to though, "You better finish what you just started when we get home."

Ashley wasn't sure if that was a threat or a promise?

But other than that little hold up, the couple resumed what they were doing before. Dressing and getting ready to drive to work, Ashley also having agreed to spend the next several nights crashing at Selena's house until his own furniture made it to his apartment, had agreed to make more plans with Vanessa about taking him back to his place to get some of his stuff while he was staying with Selena.

Of course, he wasn't taking any clothes, but his laptop, his money, some other personal items were going to be collected and brought back with him to Selena's for the time being. Selena couldn't take him there because her shift was much longer than Ashley's time shadowing Vanessa would be, so she volunteered to do it over the phone.

Vanessa also however received a good scolding/prasing from Selena when she called. Chastising her for putting her boyfriend in such an uncomfortable situation for him...but then thanking her gratefully for doing the same thing as now it seemed to only boost the level of passion and trust in their relationship.

So...they called it square for now. But the next time she got an idea like that, Selena would like to be informed about it.

The couple finished preparing for the day and left the house, heading off in Selena's ride to Lunar Lifters, and repeated the same process as yesterday. Parking in her assigned spot, entering the gym and parting ways at the front desk with a kiss goodbye that left Ashley with a longing stare as he watched his beautiful, dominant, kinky girlfriend walk away until she was out of sight in her office.

Only for Vanessa to again, snap him out of his pink haze, and draw him to the back of the desk where he would resume shadowing her.

"So...we have to do this for a full week before I can qualify as working here?" He asked her curiously.

Vanessa nodded, kind of half paying attention in her own seat, examining her nails by holding them up close to her face. "Mhm, yup. I'm supposed to also let you take a few customers on your own a few times before you can be officially labelled as work ready."

It was almost a little jarring how non-seriously she seemed to take her job. But according to Selena, she was very good at it, so maybe she wasn't kidding about it being one of the easiest jobs in the world.

"Okay well...when's that gonna happen?" Ashley asked leaning over onto the desk in front of them.

"Mmmm..." She shrugged a shoulder, "Whenever I guess, I assume you retained everything I told you yesterday?" Ashley nodded, "Then yeah, whenever you're ready just ask to handle a customer and I'll let you take it, see how you handle the job and if you need help I'll be right beside you." She lowered her hand and stretched her arm out far, looking over the work she did on her nails. Ashley hadn't seen them up until this point and now got a good look at the hot pink color of them.

Vanessa, while being a bit...aggressive when it came to things she wanted to do, similar to Selena he supposed, she still seemed like quite the girly girl. Her brunette hair always had a glorious sheen to it and was perfectly straightened reaching just below her chin. And every time he saw her she was always wearing a pretty dress that hugged her gorgeous, curvy body. Even today she wore a dark grey one with some wavy lines barely noticeable in the design of the fabric. With sexy high heeled shoes that strapped around her ankles and between her toes, which since they were exposed, Ashley could see that her toenails were actually painted the same color as her fingernails were. Vanessa clearly dressed to kill.

Her nails though seemed to be giving her a bit of trouble today, at least that's what it appeared like considering she wouldn't stop looking at them.

"Is um...something wrong with your nails?" He finally asked after a while of just waiting and watching her fiddle with them.

She glanced at Ashley, "Hm? Oh, no. Well I'm not sure..." She tilted her head looking at them, "I worked on them last night and I thought they looked mega cute but now I'm thinking maybe I should've gone purple, or creamy..."

Ashley smiled in realization, "Oh, heh, I thought something was wrong with them."

"Nooo of course not, tell me hun what do you think?" She swiveled in her chair and scooted closer to Ashley, holding out both of her hands for him to look over.

"Oh! Um...well..." His eyes glanced down over her dolled up digits, looking at the bright pink color she painted them. Now granted, Ashley didn't know much about nail polish or really make up at all, but he thought that they still looked nice from his standpoint. "I mean...they look good to me."

Vanessa gave a half-hearted eye roll and a slight smile, "Thank you, but gosh, you may be dressing girly now boy but you still don't know much about acting it unless it's taking it up the booty." She teased him again.

That about confirmed that Vanessa was aware of his and Selena's bedroom escapades. You think he'd be getting use to all the forward comments by now and not being so embarrassed when someone sends one his way. But that was not the case, he still felt the heat rush to his cheeks and his head immediately darted around to look and see if anybody was close enough to possibly hear what she said. "Vanessa, come oooon..."

She snickered, smiling sweetly at him, "I'm sorryyyy but you're so fun to tease!" She pulled her hands back and spun in her chair almost childishly, keeping eye contact with him as she whirled. "That little blush to your cheeks, and how you duck your head down just...ugggghh Selena you lucky bitch!" She playfully growled up at her boss's office.

Ashley still remained sheepish, "Well...I'm still getting used to doing this for her." He half-heartedly gestured to his outfit. "So... yeah, I really don't know what I'm doing, I just want to make her happy, so I do what she likes. And if that's acting like a... girl... then I will, I'll get better at it I guess with time but, for right now the wound is still fresh." He exaggerated.

She tilted her head at him and blinked a few times, "Okayyy, I'm sorry for teasing so much hun. I just think you're cute and I've been waiting for someone beside me at this job for so long, plus I'm use to the type of friendship me and Selena have. Which you've seen it, we call each other sluts on a regular basis we're just comfortable being bitches to each other." She joked managing to get a little ghost of a chuckle out of Ashley. She then scooted back up, "Okay, serious girl talk for a second." She began scooting closer to Ashley once more. "You wanna make Selena happy, and Selena likes it when her boy toy acts like a girl for her, I dunno know why she's just wired that way. It's almost like she should've been born with a real dick or something right?" She suggested.

Ashley shrugged, "I mean..."

"But anyway!" Vanessa cut that off and went on, "You're cute as fuck Ashley, you gotta know that and you gotta own that too. It's not gonna be enough to just have an ass that won't quit, you gotta accentuate it with feminine wiles that'll drive your woman absolutely bonkers for you. And I mean more so than she already has!"

The teen seemed a little apprehensive still, but at least slightly intrigued, "O...okay...how?"

"Well...I think you have the perfect tutor sitting right in front of you." Vanessa gave him a wicked grin which Ashley instinctively leaned back from, "I think you and me need to take another lunch break adventure today. Especially since our last one ended up such a roaring success." She said cheekily, "And I think while we're out, I can give you a crash course at being girly to please your girlfriend! Starting with something liiiike nails!" She waved her fingers again in his face, flashing her colored tips.

Ashley almost felt the urge to laugh himself at this, and he began to wonder if possibly Selena was putting Vanessa up to all these tasks with him. Probably not but she seemed so enthusiastic and ready to go that he couldn't help but wonder. "My nails?" He asked, "We're gonna...paint my nails?"

"Not us, you are! Hehe, we won't have the time to get you a manicure so I can just get you some basic supplies to use on your own, and show you what's good, what's meh and tell you how to use it so on, so on." She explained.

He looked down at her hands again at that, considering his options. He could always just say no, explain that he's not ready or not comfortable. But he found himself genuinely considering her proposal. Weighing the pros and cons of either nodding his head yes, and welcoming himself to the world of girly, or declining and trying to figure it all out himself while holding onto whatever dignity he had left.

His eyes glanced up to Selena's office again as they had done so many times before, thinking about how she reacted to the dress that Vanessa selected for him, and the purple panties. If she was right about that, maybe she was right about this too. So he settled his gaze back down on her painted nails, "They do look really pretty..." Ashley relented, for some reason, something as simple as coloring the nails on your fingertips could do so much to enhance looks. The human mind was definitely a weird thing.

Vanessa giggled, "Thank yooou again. I love hot pink, but if I had to choose, I think a more... milky pink would definitely look great on you."

Ashley's head dipped sheepishly and he toyed with a lock of his hair, he hadn't cut it in quite a while now, so it reached just below his shoulders. Not that he was complaining of course, both he and Selena talked about it this morning and agreed that they both liked it long, "Ehhhh...I'm still not one hundred percent yet...I mean this is already a pretty big step so far..." He gestured to the bright yellow blouse and yoga pants on him. "Me and Selena are gonna go shopping for more clothes that I can wear for our fun, but painting my nails? Geez...that's really..."

"Girly?" Vanessa teased, instantly earning that patented Ashley pink blush. "I think we already confirmed that when you do stuff like that your girlfriends pussy gets wet honey."

"Geez Vanessa...do you have no shame?" Ashley asked, feeling like a turtle in the moment from his head sinking so far down.

"Nope!" She said proudly.

And same as yesterday, the receptionist, and the receptionist in training both went about their day at that. Vanessa going over a little bit more of what she'd like to teach Ashley about. Including how to sway his hips intentionally while he walked, how the feminine way he bent over desks could be used as a deadly weapon to getting what he wants when it came to Selena. How little things like playing with his hair, fiddling with his skirt, or biting his lip can be construed into feminine weapons of mass flirtation.

Vanessa almost laughed out loud when Ashley borrowed a notepad from her desk along with a pen and started writing down notes on, 'how to be girly.'

Some time after that though, the lunch break came, and Vanessa once again hurried Ashley out to her car to take him to the same Mall he had been to almost every single day the last week consecutively. With the purpose in mind of purchasing the clothes Selena and he were supposed to go shopping for, because Vanessa insisted that if he let Selena pick his outfits for him, he'd have nothing but sports bras and lingerie.

Ashley wanted to defend her upon hearing that, but he stopped short and kind of had to at least give Vanessa that one. If he knew anything about his girlfriend, he knew that Selena would probably only put him in more yoga outfits and slutty ones.

They drove their quickly, planning to get a lot done in just the hour that they had, and ran inside the building hastily.

Since he had been here repeatedly now, Ashley was getting a much better feel for the layout of the place and followed along with his guide easily. Running straight to the girls clothes section and started to pick out outfits for him.

Vanessa giving her Sage worthy advice the whole time, "Okay now you have a rocking body already, so we wanna make sure to show that off a little bit, but not toooooo much. Some nice booty shorts for hot days and skimpy tank tops for when you're keeping cool and keeping sexy. However that's only a fraction of what your wardrobe can consist of, because you're cute as fuck! That's your main weapon, you wanna play that up in your outfits!" She ranted as they grabbed a cart and rolled down aisle after aisle.

Thankfully rather than just throwing whatever she wanted him to wear into the cart, she actually asked for his approval first this time. Well...with most of the outfits at least. There was still one or two that she just squealed over and threw it in saying he 'haaaaaaaaaad to have it' without giving him any say.

The clothing consisted of dresses, skirts, tight tops, tank tops, booty shorts, leggings, some more yoga pants, socks/stockings, bras, which still baffled Ashley a little bit since he didn't have breasts. But A cup bras would definitely fit him, and give him the appearance of having tiiiiny little titties underneath some of his tighter tops. And of course the best for last...panties.

Selena purchased him a plethora of thongs to choose from, but Vanessa was getting him the cutest pairs of girly underwear that Ashley could practically feel cradling his boyhood just by looking at them. Baby blue, pink, bright yellow, pink again, purple, more pink, red, black, pink, pink, pink. The cart was getting filled to the brim with clothing, even though they knew he wouldn't be able to try them all on in the time span they had available, Vanessa just reminded him to keep the receipt if something didn't fit or didn't look good.

Now Ashley couldn't lie, as much as this was embarrassing to do, YET AGAIN. It still felt good to have somebody going so out of their way to buy so many things for him, he felt like he was being spoiled rotten by two beautiful women.

Plus, something else that also was a bit interesting this time around, rather than looking at the clothing with worry, annoyance and reluctance, Ashley actually found himself looking at the pile with a hint of...anticipation. This pretending to be a girl thing was beginning to become less of a burden and more of an exciting, perverted adventure that made his body tingle.

Like even now in the tight yoga outfit, technically a boy could be wearing something like this too but, as he looked in one of the standing mirrors, lined along the walls of this section of the store, he took a look at himself.

The yoga pants accentuating the swell of his plump ass so much, and the bright yellow color on his torso looking so feminine, that if he didn't know he was a boy, he really couldn't blame someone for thinking he was a girl. He took a glance about the area while Vanessa sifted through some more frilly shirts, it was still in the middle of the week and during the day so the mall wasn't extremely populated with people. But there were a few ladies who had men walking with them through the various aisles of the stores. Picking out certain things for their own selection at home he was sure.