Born to Be Ch. 03

He sounded genuinely confused and even a little upset over the simple purple sundress, like he was more unsure of this moment than any other decision he had made in his life and Selena's heart hurt hearing the conflict in his voice. So she quickly closed the distance between them, stepping up, "Honey, I'm not gonna force you to wear it." She quickly approached her tiny boyfriend and wrapped her arms around him, placing a hand over the back of his hair and resting his cheek against her firm breast. Ashley felt a bit surprised by the sudden embrace but didn't pull away. He gladly accepted it, feeling like a hug was more needed than anything right now. "Listen, baby...I like to fool around, I like to tease, and I think you look sooooooooooooo fucking cute in these kinds of clothes, but I don't want you to be unhappy with them on." She petted his hair a few times. Loving the sweet smell of his shampoo, "I'd only want you to wear these if you wanted to. With the exception of the uniform for the yoga class." Ashley rolled his eyes, of course she had to throw that in. "But I promise, I care about you way too much to force you to do something you don't want to. And yes, Vanessa was right, I do like it when my sexy as fuck boyfriend dresses like this for me. I like it when he calls me Daddy and I like it when he let's me call him my beautiful baby girl." She continued, stroking his long locks lovingly, "But I told you before, I'm not gonna force you to do something you don't want to do. And I stand by that. So if you say the word we can take the dress off right now, return it and use the money to get a pizza or something. And Vanessa can suck a butt" She leaned back and tilted his head up to look at her, "Sound good?"

The big blue eyes sparkled up at her, and that frown slowly managed to turn upside down with a cute smile. Vanessa hadn't been wrong about Selena's apparent love for this kind of attire, but something that Ashley had been wrong about was the idea that Selena would make him wear it. She didn't need him to dress like this for her to want to be with him, and she was willing to completely bypass the girly clothing if it meant making him more comfortable.

And that knowledge alone was like a massive weight lifted off of his chest, he could still do this for her. But he didn't HAVE to, only if he wanted to dress like this for her.

So although Vanessa's plan may have been a bit forward and an aggressive approach, maybe she had the right idea after all.

Ashley felt his heart swell up, Selena wanted him more than she wanted the fetish, and that was more than enough for him to quickly hop up onto his tip toes to plant a quick kiss on Selena's lips in a surprise attack. "Oh! Heehee, hello." Selena giggled. "What was that for?"

His smile was wide and happy now, "For being the best damn girlfriend ever." He gushed, feeling like he made the right decision in taking this leap of faith into the relationship, so he said, "If you like this, I'll happily do it for you. Anything to make you happy...um...daddy." He barely managed to get it out without a little giggle of his own. Now viewing that word as less of a fetish but, trying to think of it as more of a simple pet name. Just like baby, sweetie, honey, or any of those. And that made it a little easier to say.

Selena however, still got excited whenever he called her that, and she quirked a brow, "Really now? You gonna start calling me that from now on baby? Don't make promises you can't keep"

Cutely, Ashley shimmied back and forth, his skirt swaying with his movements, "Iiiiif you like it so much then...I think I could get use to it. Maaaaybeee." He gave her his own flirty smile, suddenly beginning to feel more confident in a freaking dress than he had been for most of his life.

"You are so fucking perfect." Selena said suddenly. "Seriously...I feel so lucky. Really, you're one in seven billion baby. I can't believe I got you."

"Selenaaaaa..." Ashley brushed a lock of hair over his ear, feeling bashful again. "You're the perfect one, and I'm the lucky one."

They both continued to stare happily at each other, exchanging compliments and sweet words of romance and puppy love. Eventually though, Selena managed to do what she always did, and brought the conversation back into the gutter where her thoughts always lingered the most. "So you'll...dress like this for me, a little more?" Ashley nodded again, "Would you also maybe...do that little twirl for me one more time? Cause that was fucking adorable."

That made Ashley laugh, the power that a simple dress and a spin could hold was an amazing thing. And if she liked it so much, he would do it. "Sure I can."

He took a few steps back, and Selena leaned back on the arm of the couch, ready to take in the sight of this little spin. His first one was so quick she didn't really get the chance to take in it's magic. So he raised his arms above his head, lifted one leg off the ground and touched it down quickly to propel himself to the right and spun again. Once more a full three sixty twirl that kicked up the skirt beneath him, only this one was slower and allowed a bit more of a teasing glance all the way up to the top of his thighs where the panties began, in an adorable pirouette that stopped with Ashley flawlessly placing his feet back on the ground, wide silly smile at Selena's lip biting expression.

"Okay...I am aroused." She stated blatantly.

And again, Ashley laughed, both of them shared a childish laugh in the moment with Ashley coming forward to once again throw his arms around Selena's waist and embrace the taller woman in a tight hug.

Selena hugged him back and the couple rocked in place for a few moments, just holding each other. Feeling like they reached a new level of comfortable with themselves in this fresh relationship. A big step for Ashley especially, and his heart felt full in this moment almost as much as when she first took him home after their very first date.

Eventually, they gently pulled back from each other but kept their arms looping their bodies together. Ashley looking up at Selena, and her looking down at him. They shared a look like this for a few seconds, that's when Ashley suddenly said. "All jokes and dresses aside...do you promise to be good to me?"

Selena was almost taken aback by this sudden inquiry, but she nodded, "I promise."

"And you promise you won't break my heart?" He asked also.

This question almost sent a pang into Selena's chest at the mention of it. She couldn't bare the thought of Ashley being hurt, physically or emotionally, even less so if it was inflicted by her. So she looked deeply into his soul, and said as sincerely as she could, "I promise you, I will never break your heart Ashley."

And it felt as if the two were floating, lost in each other and the world was forgotten. That promise was all the boy needed to once again lift himself up as high as he could on his very tip toes, and tilt his chin up searching for a kiss. Which Selena sought to give him by leaning down, and carefully bringing her own thick, full lips to his. Engaging now in one of the most passionate, tender kisses that they'd had to date.

Their lips softly moving against each other, the height difference super noticeable with Ashley barely able to reach her despite rising up as high as he could and Selena having to lower her head into almost an odd craning angle just for them to be able to kiss.

He lifted his arms up higher though, removing them from around her waist and instead hooked them around the back of her neck while hers went lower down, at first rubbing his lower back for a few extra seconds while they kissed, but then began grabbing handfuls of his dress and pulling it up higher and higher until his cute, panty clad, ass was exposed. Her hands quickly moving to it and both grabbing large handfuls of the squeezable flesh.

"Mmh..." Ashley cooed, suddenly feeling the 'whoosh' sensation of being touched like this. His butterflies in his tummy feeling quickly being replaced with butterflies somewhere else. And he didn't stop her, he just continued to enjoy the feeling of her lips on his own, letting her tongue stroke along his and parting his lips to accept it repeatedly. Fully giving his mouth to her, and if her grabby hands were any inclination, he'd be giving his body fully to her again soon too.

Her strong hands gripped his butt cheeks firmly, squeezing and kneading the flesh, toying with it like a moldable clay. She palmed and squeezed his ass while her lips smacked his, dipping her tongue into his moist tunnel and tasting all around. "Mmmhm..aah..." He gasped as they separated, tongues lashing each other a few times without any lip contact in a lewd form of kissing before reconnecting for a few more smooches. Up until Ashley managed to break off long enough to say, "Behh...Bedroom?" He asked breathlessly.

Selena smiled, "Baby...with how cute you look? Nnf...I'm not sure I can wait that long..." She kissed him again and pulled his dress up higher, bunching it at his midsection so she had complete access to his panty covered ass. Both hands grabbing each cheek at the same time and giving them a quick simultaneous slap.

"Mmmmm..." Ashley moaned in delight at the sharp contact. The panties giving him no protection at all from the impact, and waking up all the nerves in that area. Telling them to get ready for play time. He seemed to be much more receptive to spanking now than he was before.

She kneaded his rump again for a few more seconds before pulling on his side shifting their bodies around, but not yet breaking the kiss. She spun them around so that Ashley's back was facing the couch, then shuffled forward to help guide him backwards until his legs touched the cushions.

And quickly getting the message, Ashley sat down on the couch, quickly transitioning to reclining back, and laying as Selena crawled on top of him. Never once did their lips disconnect until finally the both of them were laying flat, Ashley's legs spread just wide enough to accept Selena in-between them.

Her mouth didn't plan on staying away from him for long though, it just simply moved to other spots on him that she loved to kiss. Namely, his slender, sensitive neck, lowering her head again to suck on the pale flesh there and pull the skin into her lips. Surely leaving a hickey or two with her teeth as well.

"Nnff..." Ashley mewled a bit, his neck definitely being one of his pleasure spots, she nipped and suckled, like she had a few times before now. Only this time, it was different somehow, like they had reached a deeper level within each other, and each little kiss felt warmer than the last.

Her lips trailed down his collar bone, running over his shoulder until they reached the strap of his dress. Selena gave him a quick glance before reaching up to take the strap in her hand and carefully pulling it over his slender shoulder, followed by its twin on the other side. Ashley relaxed into the couch and lowered his arms to his sides, hoping to give her easier access to disrobe him.

She pulled the straps down, taking the front of the dress lower over his front until it exposed his naked chest. Smallish boy breasts bared to her now and Selena grinned at her prize, she made a mental note to pick up some A-cup size bras for Ashley's own tiny titties. Not just sports bras anymore.

Then she dove down, wrapping her lips around one of his hard nipples and giving it a good hard sucking. "Uhhn!" Ashley squeaked, "Ooooh...Selena..." He moaned out her name, closing his eyes and loving the warmth of her lips on him there again.

She made an audible suction sound as she released the nipple from her lips, lashing her tongue out at it briefly before leaning back up and looking down at Ashley. Grinning with lustful intent before reaching down beside the couch where she threw down her purse upon entering the house and unzipped it. Fishing around inside until she produced the same black dildo she had constantly used on him.

"Do you carry that thing around wherever you go?" Ashley asked at the sight of it. "Isn't it...dirty?"

"Only if I'm not single." She winked, answering his first question. "And I washed it at your house so, no, we're good to go." And his second one. "But fiiiirst, I have to lube you up baby. And..." She paused then made a show of pretending to look down at her purse, and back and forth at her house. "Oh no! It looks like I left the lube at your house. Silly me!" She placed her hand on her cheek, "I can be so forgetful sometimes."

Ashley quirked a brow, giving her a semi-amused look, "Okay..."

"Hmmm...oh well, I'll just have to improvise I suppose." She said, almost threateningly as her body sank back down onto all fours, crawling lower on Ashley's form until she got to the space between his thighs. Still covered in the light purple panties, but those would be no trouble to remove at all.

She took hold of them with one hand and eagerly began tugging them down Ashley's smooth limbs. He brought his legs together and lifted them up to assist with her taking them off, and spread them apart again as soon as they were removed and tossed away. Revealing the sacred valley of his ass right beneath his little balls, and the precious little love hole that awaited her eagerly. Selena licked her lips and sank down onto her belly, using one hand to apply a gentle pressure to one of his legs, encouraging him to spread them wider as she went in for a taste.

Her tongue poked out of her lips and swiftly dove into her boy toys booty, instantly earning that sweet high pitched gasp from Ashley as the heat of her appendage hit his core. "Haa! ...haaaaaahhh..." One girlish intake of breath, followed by a long hot exhale of sweet relief. Feeling Selena's expert tongue movements already beginning to take hold of him and make him melt into the soft cushions of the couch.

Selena laid completely prone with a faceful of Ashley's delicious booty, her tongue greedily digging into that sweet little star and savoring the taste. Slicking it up with as much spit for lubricant as possible, she breathed hotly on him, moaning a bit herself as she felt her own pussy quiver with the desire to take him now!

But she was patient enough for a little foreplay first. Especially because the faces he made while she rimmed him were more than worth it. She watched from just below his twitching little prick, steadily getting as hard as it could from her attention, as Ashley closed his eyes and enjoyed her lower kisses. His hands almost absentmindedly trailing up his body, over the bunched up dress around his midsection to play with his nipples.

This made Selena nearly moan out ecstatically, watching him willing reach up to play with his breasts like this while she ate out his love hole.

He was perfect. Everything she wanted, everything she needed.

Ashley.

She pushed her tongue firmly against his entrance until she was able to wriggle it inside. Another shocked inhale from Ashley drove her forward, swirling her tongue all around and coating his inner muscles in plenty of lube as she was able to give.

Ashley pinched his nipples while Selena made out with his ass, pulling and tugging them up a bit. Toying with them to feel those delightful little volts of bliss they generated whenever they were tweaked. Coupling that with her tongue slithering about in his anus, Ashley cooed, "Mmmmmmmhmm..." Making long low noises of approval, accepting all that Selena was offering.

She gave his hole a few more good sloppy kisses before pushing up on the couch and looking over him again. Her own face getting sweaty and her breathing heavy, "Ready honey?" She said between pants.

The young boy beneath her released his hard pink nubs as she asked that and brought his hands close together in the center of his chest. He looked down at her legs as she shifted them about to stick them through the loops of the harness, pulling it up and into place, getting ready to fuck. He bit his own lip at the sight, watching her ready that massive fake cock to destroy him with.

Before the sight of it worried him, but now...it only served to turn him on more than ever before. So he gazed up at his ebony Goddess and nodded, "Yes...daddy..."

"Nnnf..." Selena bit her own lip and leaned down over him after clipping the belts all into place. "Fuck I love that so much baby..." She kissed him again, looming over his body in the missionary position now, priming herself to penetrate him.

He kissed back gratefully and tried to spread himself wider, arms hugging Selena around her back, ready and willing to take her inside of him again.

She reached between them, and took hold of her cock, guiding the rubber toy to his wet boy pussy, and rubbed the tip around his entrance in a few swirls. Ashley didn't flinch this time, he only continued to chew on his lower lip in anticipation. At least up until Selena once again locked their lips in a french kiss while she lowered her hips, pushing her strap-on cock into him. Breaching the tight anal ring and sinking right back into its home.

"Mm!" Ashley moaned briefly into Selena's lips at first, the initial surprise of it's entry still intense, but subsiding quickly while she pushed it all the way in. "Mmmmmmmm..." Followed by a long low, throaty moan that Selena greedily swallowed up.

No resistance, no slow adjusting, Selena just sank into him, inch after inch after inch. Pushing her big black dick deeply into her baby boy...

Or rather...her baby girl.

"Mmmm...aaaahhhh..." Selena started to moan into Ashley's lips as well, but as they broke apart it came out into the air around them. "Fuck...you're always so tight baby..." She whispered. Of course, being a strap-on, Selena couldn't actually feel his tight tunnels clenching up around her cock, but she could tell just based on how much strength she had to put into pushing that dildo in every time, that he was practically virginal every time she went in.

"Ooooh..." Ashley cooed again and responded, "And you're...s...so...big..." He managed to get out. "So...big..."

Selena grinned, "You like my big cock baby?"

Ashley nodded, teeth chewing his bottom lip hard, "I like it...I...like your big cock...daddy..."

Now it was Selena's turn to feel that incredible 'whoosh' feeling throughout her chest as Ashley laid out a surprising response to her dirty talk. He'd called her daddy before, but stinging it to a phrase like that just seemed to awaken a lioness within Selena that made her desire to ravage Ashley grow insurmountably.

"Ggrrrgh...that's what I like to hear...baby girl..." She responded. he turned his head away coyly, but looked back at her with a sidelong glance, "Do you like when I call you that?"

Ashley thought about it for a second, he had spent way too long fighting the accusations of him being a girl from all corners of the world. People in passing called him a girl, boys in the locker room called him a girl, and even his girlfriend liked calling him a girl.

Maybe it was true that if enough people accuse you of being something, you eventually start to side with them. He's only human after all, and he can only take so much, so maybe if he just accepted and embraced his feminine qualities, he might be more comfortable dealing with them than ever before.

Plus, the way Selena looked at him, when she uttered those words, with a fire and a passion in her eyes that just read, 'I want to destroy you', it made his body tingle. It made his loins burn with desire, and it made his insides quiver.

Maybe he had liked it all this time? Those goosebumps when he knew he was being stared at or lusted after, the embarrassed blush he always got was just flares of excitement. And maybe he just refused to acknowledge it due to his preconceptions about masculinity and his desire to appear attractive to women. But this girl, who just so happened to be one of the sexiest women he had ever seen, found him so desirable when he was dressed all girly like this.