Born to Be Ch. 09

"Ooooh a maid outfit." Ashley nodded, feeling like he should've seen it coming. Kind of fitting seeing as how he does all the cleaning around the place anyways. He giggled a little to himself at that and began to undress, he had to swap out his red thong for a black one earlier since he had made a mess of it in the kitty outfit. He hoped this one wouldn't be soiled as well, but who knows when it comes to Selena.

He put the whole thing on and looked at himself in the mirror, adjusting the head dress a little so that it sat right and looked over the...slutty...sexy maid looking back at him! "Oh wow!" He thought, plus with the black heels on, he was actually a few inches taller! He'd worn some high heels that Selena had provided him before but only out of her supply, which were too big for him.

Walking in them was a little bit of a challenge but they looked so good on his feet, and the added three inches to his lackluster five foot form was something he delighted in greatly!

With this outfit on and ready to go, he unclipped the feather duster and headed out into the bedroom again, ready to see the look on Selena's face.

Not even being revealed to her for a minute she sat up more on the bed and shouted, "Oh my Lord in Heaven you're hired!" Ashley laughed, swearing that he almost saw her eyes actually turn into a pair of throbbing hearts for a moment.

"Why thank you!" He giggled with a big smile. Then approached her on the bed, making each step carefully and calculated enough so that he didn't stumble and embarrass himself. Then turned his back to her and gasped, "Oh my! It looks like someone has spilt something over here. I'd better clean this up." Taking a step away and doing a full bend over while pretending to use his duster on the floor. The skirt part of the maid dress hiking up and giving the ebony woman a full upskirt view of her slutty maid.

"Oh wow yes you are hired so hard. I think there are a few more spots that need to be cleaned too, right there, there and there." She said, pointing to a few spaces around him but not even looking at the carpet. Just staring at his gorgeous thong clad ass. The bubbly cheeks barely allowing the black line of the thong to be seen between them.

The boy giggled some more at her comment, almost a little too much though as he nearly stumbled in the heels. If anything, he was going to use this outfit to practice walking in them. They looked really good! But he played it cool still and continued to walk to each invisible spot on the floor that needed to be cleaned. "Oh yes! Of course Monsieur!" He spoke in a fake french accent. Not even knowing what the word he said was, he'd just heard it in movies all the time so he figured he'd add that into their little game. Selena clearly approved as she continued to watch him move. Watching the little black thong with every opportunity he gave her in each upskirt. All the way until the final 'mess' was cleaned up, Ashley stood upright and spun around. "Next outfit?"

"Take your pick my french maid." Selena gestured to the array of outfits. There were still five to go through, and this was fun! Ashley was enjoying this little modeling experience more than he thought he would.

He quickly picked up another, then grabbed the edges of his skirt and lifted them, giving a little curtsy. "Merci beaucoup!" He threw in, which that phrase he knew, then spun about heading back to his unofficial changing room.

"Oh yeah, I'm paying for you to take french lessons and learn how to speak it, and then I'm fucking your fucking brains out in that baby." She said to Ashley's back while he walked away.

But upon hearing this, he turned about and put a hand over his mouth with a little gasp in faux shock. "Monsieur!" Mockingly pretending to be aghast at her words. Little did she know, Ashley nearly squirted in his panties hearing her talk like that. Saying how she was going to fuck him, after the little lewd display he put on, it always turned him on. He got excited so easily these days. And he could cum so many times without needing to take a break.

Almost like how girls could cum multiple times and still want more...

Regardless, he re-entered the bathroom and disrobed again, neatly placing the maid outfit back into its package and going for the next one. In this bag, he first noticed a lot of frizzy tinsel like objects. Putting him off for a moment when he didn't immediately see the clothing portion. So he took those out first, and that's when it hit him at what costume this was.

Those tinsel things, they're pom poms, and beneath them he could see an extremely tight looking blue crop top with the numbers 69 on the back, and a short short skirt that would barely reach his wrists at his sides. Along with white converse sneakers and blue and red striped knee high socks.

And Ashley's heart started to pound, a cheerleader costume, "Ohhh my Gooosh Selena you're so baaaaad..." Pulling out one piece at a time, if his clit wasn't hard enough before, it was now! And he eagerly started to unwrap the clothing to put it on. This was so exciting and dirty! He wanted to dress in these costumes all the time!

An added bonus was that the crop top squeezed his chest so tightly, it brought his little tits together and gave him something that could possibly be construed as cleavage! And the skirt was so tiny, about half his ass was visible to the world. If he wore this to whatever party was planned... "Oh God..." Ashley breathlessly whispered as he put the socks and shoes on. Then as he headed to the door, he got an idea, just to top it all off, going back to the mirror he grabbed his long hair. Finding one of the ties on the sink and putting it up into a single ponytail! "That'll do it!" He said confidently, then moved for the door.

This time, now less nervous and way more into this, he practically humped out of the bathroom and did a twirl, flipping the skirt up and showing off the other half of his ass that it didn't show off. A pom pom in both hands, he strutted up to a very wide eyed and speechless Selena sitting on the bed.

Smiling ear to ear and bringing his hands behind his back, like a bubbly cheerleader he skipped over, "Hi! Are you the captain of the football team?" Putting on a ridiculously silly, beverly hills girl style voice, he reached out and felt along the side of Selena's arm, squeezing her bicep. Thicker than Ashley's thigh! "Oooouu...such a handsome...strong jock!" Ashley winked at her, "I'll cheer EXTRA for you at the big game tonight!"

"Ohhhhhhhhhh my Gosh baaaaaaabe..." Selena grew the biggest grin, "I...wow I don't have words you look so fucking hooooot." She reached out to feel along the side of Ashley's very exposed thigh, "Fuck yes I'll be your jock if you'll cheer for me."

Both of them weren't very sure whether or not they should laugh at themselves, or get more into the moment. Because they were basically enacting a porno right now, but judging by how horny both of them were getting, Ashley decided to get more into it. "Oh I'll cheer for you...And wait till you see the other girls throw me in the air. Im so small they toss me hiiiiigh up before they catch me... I could never play football like you do..." His hand tracing over her muscles, "You're so big...so strong...and I'm so little and weak..." Flirtation rolling off his tongue.

Selena brought her hand up to Ashley's and took hold of it, "Mmm baby, I'm sure I could throw you around much better than a bunch of bitchy teeny boppers..." She lifted her chin up, a rare occurrence where she had to look up at Ashley due to her position lower on the bed and his standing up.

Again, her words bringing Ashley dangerously close to just squirting right on the spot. The desire filled looks she always gave him, he just wanted to melt in front of her, let her do whatever she wanted to him whenever she wanted.

He swallowed a lump in his throat, "Uhm...so...next bag?" He offered, dropping his cheerleader personality in hopes of stopping this roleplay before he ended up face down ass up.

And his girlfriend knew it, her grin saw right through his attempt to escape. She lifted herself out of her position onto all fours and started to slowly crawl right to the edge of the bed in front of him. "Are you suuuure you don't wanna...cheer...for me right now?" The word cheer definitely sounded like it was taking the spot of something much dirtier in that sentence. "Baby girl..." "I...I..." Ashley stuttered, "I kind of...want to go through all the outfits before...before we...you know..." Hot faced and nervous now he was about to be pounced on again. He took a few nervous steps backwards in fear of this.

Selena just continued to grin, playfully mimicking his previous cat like wrist movement he made when pretending to claw at her. Although she made more of a growl sound rather than a purr, but then she leaned back. "Okaaay, pick another bag you sexy little tease."

Tiiiingllleeees everywhere. Ashley felt like he could breathe again the moment she let up, but at the same time he couldn't get out of there quick enough. "This one!" He said and swiftly spun around, dashing to the bathroom yet again to do another outfit change. Flustered and bothered, that came a little too close with her responsive behavior.

Of course he probably should've expected that with his own teasing directed at her. This was so much fun, but it could also lead to pound town really fast. All the outfits were blatantly sexual, and he was sure whatever was up next was going to be the same. But that didn't mean he wanted to stop being playfully flirty, it just meant that everytime he did, Selena's ability to hold back on wrestling him to the floor and butt fucking him until he saw stars would get weaker and weaker.

Now that also didn't mean he'd never get to try on all the outfits, it just meant it would take longer to do it. So did he just go for broke? Play a character in each outfit? Or just model it and play it safe?

He glanced into the mirror, thinking over each option. Playing it safe was boring, hence why they never used condoms. So why the Hell not, if she fucked him to oblivion, he would go there with a smile on his face!

So he dug into the next package, but as he did so, he felt like he probably should've seen this one coming. It was so popular and fetishized literally in all porn everywhere. He actually rolled his eyes and shook his head, "Of course, am I not jail baity enough for you Daddy?" Ashley whispered to himself as he pulled the garments out.

A black and red plaid skirt that goes to mid thigh, a white button up blouse with a red tie. Thigh high white stockings and black flats, she even bought a fake school book and a pack of chewing gum to go with it.

He took a moment to think about how he was going to play this one, did he go innocent good girl student? Did he go hardcore nerd? Or did he go bitchy plastic priss? A couple of options in this venue. But it was the chewing gum he felt that gave him the final push on how to play this up, the innocent school girl has been done over and over again. And he's been being sweet and goodie goodie up to this point, so this time, let's go bitchy.

He put everything on, slipping into it all and righting everything in place. Also changing his hair so that he now had two ponytails hanging down on each side of his head like pigtails.

Then stuck three pieces of the gum in his mouth and chewed for a couple minutes, happy that it was actually flavored, and blew a bubble. Letting it pop at first, then resuming chewing. He grabbed up the book, and loudly opened the bathroom door, letting it swing open and hit the wall uncaringly.

He smacked his gum in his teeth and stepped out into the bedroom, trying his best to look bratty and childish, "Hey." He tossed to Selena, standing in front of her with a hand on his hip, blowing a big bubble in front of her that splatted onto his lips when it got too big, then sucked it back in to continue chewing.

"Well hello there." Selena replied, sitting over the edge of the bed now and crossing one leg over the other. "Looking a little bitchy are we?"

"Whatever." Ashley suddenly fired back, a thick tude in the tone of his voice. Selena's eyebrows raised, "And who the heck are you?" He asked nonchalantly, chewing loud and obnoxious.

"We're gonna play this game are we?" Selena smirked, "I am your principal young lady." She leaned back, placing a hand over her knee, playing along. "And you would do well to remember that."

"Oh..." Ashley let his fake attitude drop a little, "I'm sorry I...I didn't know."

"That kind of attitude isn't going to fly in my school. Not on my watch you understand?" She waved her finger at him in a scolding manner. "Now what's your name young lady?"

In the heat of the moment, he couldn't come up with anything aside from his normal name, "It's Ashley." Her stern tone towards him definitely sent a little thrill into his nerves. "I...I didn't mean to be rude. I really am a good girl I promise." He tried to hug his book close to him. "Are you...are you going to discipline me?" He asked half hopeful, half nervous.

"I think I have to to make sure that attitude doesn't stick in my halls miss Ashley." Her voice was stern, but she sent a quick wink his way to keep him calm, reassuring him that they were just playing without breaking character, then curled her finger towards him. "Now come over here."

"O...okay..." He mumbled quietly, stepping over to her. Legs shaking in fear and delight. "Okay Ma'am! I mean..."

Selena smiled smugly, "Good girl, that is how you'll address me from now on while you're in my school got it? Now,..." She snapped her fingers and uncrossed her legs, "Bend over my knee..."

"Yes Ma'am..." Ashley nodded slowly, putting the book down on the edge of the bed, and proceeding to climb over her thick thighs. "Oh God...is she gonna..."

"Good girl...now..." Ashley felt one of her hands land on his back. "In my school, there are three specific rules you will abide by ALWAYS." The back half of Ashley's skirt was lifted up, his thong clad ass exposed to Selena for the hundredth time today, and it was still just as good as the first time. "Rule number one..." He felt Selena's hand take hold of one of his cheeks, gently squeezing... "What I say goes!" Then it was released but quickly followed up with a SMACK!

Selena whacked his booty hard and Ashley's head jerked up, "Aaah!" Yelping in pain, good pain though. The flesh of his butt rippling like the surface of water from such a firm swat. He could feel a single drop of precum leaking out of his clit...

"Rule number two..." SMACK! Another strike to Ashley's jiggly tush. "While you are in my school, you are my bitch!" SMACK!

"Hnng!" Another drop of precum spills. Selena has spanked Ashley a bunch of times, but never like this. He was actually just bent over her knee and being spanked like a disciplined child! He panted heavily, this act was insane, and yet he was getting off on it. "AAH!" Another harsh slap and another girlish yelp. Zero acting on his part, the sound of her hand clapping his booty, the feel of it, and the position he was in was making him just so damn hot.

"And rule number three..." Her hand grabbed and squeezed Ashley's booty flesh again for a moment, wiggling it and rubbing it before suddenly she smacked it again, SMACK. "You're..." SMACK "My..." SMACK "Fucking..." SMACK "Bitch!" SMACKSMACKSMACK!

"AAAH! AAAH! AAAOOOHH! AAAH" Once again she brought him over the edge. Ashley came haaaaaard squirting into his thong as she continued to spank him. The precum that had been threatening an orgasm finally bursting out in a series of strong squirts. "AAH! AAOOO! AAAHH!" Every hit enforcing the long orgasm, pleasure pulsing through the young feminine boy with each hit. And the spanks were not rookie by any means, she spanked him hard, but not so hard it was unbearable. Still enough to make him cream his panties though. "AAH! OOOOOH! AAOOOOH!" Without even fucking his ass or touching his cock too.

Selena let out a long hot breath, "Wow, really? You came from getting spanked? Ha. Fucking bitchy slut." Then delivered one more good SMACK to his rear. "Learn those fucking rules, and I'll see you back here tomorrow to make sure you've memorized them, got it?"

Ashley weakly mumbled a reply, "Aaaaahhha...yyees...Ma'am..." Still hanging limply over her thighs in this humiliating spanking pose.

"Nnf...now, get the fuck out of my office you little slut." She patted his ass one more time, then just leaned back on her elbows. Not even bothering to flip his skirt back down, just expecting him to do it himself.

"O...kay..." Ashley replied, his voice tiny and weak from his recent climax. Not acting, he climbed up on wobbly legs, flustered and hot, reaching down to grab his fake book, then stumbling through the bedroom to make his way back to the bathroom again. Not taking another costume bag with him.

When he got inside he shut the door behind him and felt his knees buckle, clumsily dropping the book to the floor, he was so winded and so shocked. There was nothing wrong with how good it felt, Selena didn't do anything bad either, it was just the intensity of cumming from spanking alone was quite a shock to his system. And he had to take a moment huffing and puffing to really re-gather himself.

Just then, he heard Selena call from the bedroom, "You okay honey? Was I too rough?"

He shouted back fast, "No! No baby not at all, it's just...it's just uhm..." He hesitated.

"Ashley? What is it?" Selena pressed, now beginning to sound worried, probably concerned that she had gone too far.

It was embarrassing already, but asking her the question would be even more so. However he had to otherwise she would be left in a perpetual state of worry when he didn't tell her what was going on, so he sighed, "Is it...is it normal...or I mean...is it weird to...to..." He paused, "You know...from just being spanked?" He managed to ask through the bathroom door.

"Oh!" Selena said, sounding relieved, "Nooo baby that's not weird at all! It's hot! It means you really liked it." She called back.

Her words comforting him in the moment, "Okay good, sorry just...kinda was a little intense. That's never happened before."

"Don't worry about it, do you wanna save the rest of the outfits for tomorrow? And just get to bed tonight?" She asked, still sounding a little concerned despite learning that she didn't do anything wrong.

Ashley thought about it for a moment, that spanking orgasm was a good hard one, and he felt pretty content with the amount they tried today. And even though he wanted to get them all done earlier, the sound of taking a break and just calling it with the love of his life sounded pretty appealing. So he replied, "Yeah, that would be nice. I'm getting pretty tired. You sure that's not a problem? I can keep going if you really want to?"

"Noooooo." Selena answered immediately, "I can wait for the rest, this was really fun and it just gives me something else to look forward to tomorrow. Plus I mean it's obvious you're spent." She teased.

"Yeah yeah." He shot back, "Well, I'm gonna get ready for bed then. I'll be out in a couple minutes!"

They went about their settling down rituals then, with Ashley brushing his teeth, stripping down and lotioning up his legs, arms and body. The delicious strawberry scented skin cream that he started wearing for Selena a few weeks back. It smelled great and made his skin even softer than it already was.

With the costumes all put aside or in the laundry, he picked out a big baggy Selena T-shirt to wear and threw it on, abandoning any form of underwear and eventually returning to the bedroom for bed time.

When he came out, Selena was waiting for him outside the door, "Wish you would've told me before you went in there you were getting ready for bed you bathroom hog." She smiled, and started to walk by him so she could get ready for bed too. Oddly enough, she had a big house, but it only had one and a half bathrooms in it. The one in the master bedroom was the one with the shower.