Born to Be Ch. 01

The Following Morning:

"Ooohhh...oww...my butt..." Ashley groaned at the soreness filling his booty still. Sleep finally beginning to fade away as he slowly started to return to the waking world, only to unfortunately be greeted first thing by literally a pain in the butt.

"Hmm?" He heard a womanly voice from directly behind him, "Oh! Well, good morning sleepy head." Selena leaned around Ashley to get a look at his face, "You must've really conked out, you slept really late. How are you feeling?"

Ashley tried to roll over to look at the source of the voice, but as he tried he felt a tug at his asshole that made him wince, "Aah! What...oh..." He started to question what was going on, only for a flood of memories to wash through his recovered brain as he glanced over his shoulder at his 'lover' from last night. She still wore the strap on...and it was still inside of him.

"Heehee! Sorry, I went to sleep last night without finishing and I maaaay or may not have woken up just a liiittle bit...still horny." She said sheepishly. And now he took notice to the fact that she was softly moving her body in a gyration. Ashley glanced under the blanket and saw that it looked as if she added some more spit to the dildo to re-lube it up, and was now carefully sawing it back and forth inside him again. "I'm so glad you woke up, I didn't think I could really wait any longer."

"What?" Ashley asked exaggeratedly, "What are...do you...what..." He again spoke in sentence fragments, "We...we had...but...and you're..."

She looked at him with anticipation, seeming to be waiting for him to complete any one of those sentences, and when that didn't happen she interjected for him, "Baby? Are you okay?"

"Wha...I, why are...why are you calling me baby?" It was the only question he could manage to get out.

Her expression then changed from entertained to confused herself, "Um...isn't it obvious? I'm calling you baby because I wanna be your girlfriend?"

And Ashley's brain stopped dead in it's tracks again, "Uh...you...you do?"

"Yeeeeah? Kind of? I mean, why else would I bring you back to my place and have some aaawwesoooome sex with you?" She asked, "I told you I was into you, and last night I showed you how much I was."

The poor boy just stared for a few seconds after that, blinking in disbelief. "If...you wanted to be my girlfriend...you could've just asked?"

Now that made Selena laugh, "Ohhh babyyy." She leaned closer to him and gave him a quick, yet still passionate kiss. "You're so cute!"

Ashley smiled a little bit at that, "Thank you...so are you." Selena snuggled up closer to him and pressed her hips a little closer as well, pushing the dildo back deep inside. "Aaah! Ouuu..." Ashley moaned, "Easy please...easy..."

"Oh, sorry!" Selena apologized.

"It's okay, just still a little sensitive." He told her, "I...I didn't know that anal sex could actually feel so good."

She rested her chin on his side, "Oh Baby...you have no idea. You're with me now hun, and as long as you are, I'm gonna rock your world." She grinned, sending a shiver of both slight fear, and anticipation down Ashley's spine.

He smiled nervously, "Um...heheh...are uhmm...you gonna take it out now?" He asked referring to the cock still crammed inside him.

"Hmm...I dunnooooo...I'm still pretty horny..." She said, looming over Ashley and making him feel very small once again. "You passed out on me last night and left me high and dry, so I think you owe me an orgasm baby boy..."

Ashley shrank beneath her, "I...I do?"

Minutes Later:

"OH FUUUUCKKK!" The small boy screamed as nearly half of his body hung over the edge of the bed. His arm stretched out and braced on the floor while his body rocked from being shunted forward by Selena's hips.

It didn't take much coercing on her part to convince him to go another round with her, tempting him with the memories of the incredible release he experienced from their coitus the previous night. And now here they were, Selena spooning young Ashley from the side, one of her legs laid out flat beneath her with the other supported on the mattress. A hand holding up Ashley's leg in the air and keeping him spread open for her as she drilled his ass for the second time.

This time, she was determined to reach her own orgasm, so she practically jackhammered her hips into the boys booty, slamming the bud of the dildo against her clit and smacking his butt with such force that her hips were practically spanking him. Her teeth chewing her lower lip as a tell-tale sign of her focus and arousal.

Ashley's entire chest had flushed pink from the angle he was at and his mouth was wide open again, crying out in ecstasy from the much rougher treatment she was giving him. Since he had already been gently broken in the night before, Selena was wasting no time in giving it to him harder and rougher this time around.

Not that Ashley was complaining...

He was afraid at first definitely, shocked, surprised, worried, all of the above. But now, as wave after wave of incredible bliss rocketed up his spine and radiated throughout his body, he couldn't deny how much he was fucking loving it!

His little cock was loving it too evidently, it swung back and forth slapping around his pubic area, streams of precum flying and making a mess all over himself as his prostate was once again milked for all that it had.

"Yes! Yes! Oh Yes please! Aaaaahhh!" He didn't even sound like himself while she fucked him, he sounded straight up like a porn star being drilled by a big cock.

Selena had a wild grin on her face, "Yeah, yeah, yeeeah, uggggghhh yess..." She growled through gritted teeth. Ready to finally get her own chance to cum, "Ahhh yeah are you gonna cum for me again baby?"

"OooohhGooooood yeeeeesss..." Repeating the same notions as last night, Ashley's eyes began to roll back, his body becoming easily overwhelmed by the bliss Selena was offering.

"Cum with me baby! Ugh come on...cum with me!" She rutted her hips hard into him, feeling her sopping wet pussy quiver beneath the dildo, "Do it! Come on! Cum! CUM! Uhnn....UUUGGHHHHH!" Selena let out a low chesty growl, hammering her strap on into Ashley over and over as her pussy finally got it's own release.

The boy gasped again, then held his mouth open in a soundless scream as his prick twitched, spilling out a second little load of sperm out over his tummy. Almost pathetically spewing it as his voice finally broke through, "OOOHHHH GOD! AAAGHHHH!" And the pair experienced another first with each other.

Their first, of many to come, shared orgasms together.

Ashley's little seed flying out of his flexing balls, and Selena's pussy juices leaking from within her. The pair relishing in the pleasure of each other's bodies, and both of them bringing their arms up to cling to each other tightly as they grinded and humped into each other to milk the sensations for everything they could.

It was strangely beautiful, so unexpected and yet so...magical in a way. Neither of them expected this to happen, but as they finished riding it out. Selena pulled Ashley back up, and looked at him closely, and he looked at her.

Both heavily breathing and staring into each other, wondering what this was. It was odd, unconventional, fast, and definitely unique, but...they didn't care. Ashley knew this was good, nothing could feel so great, and not be right. Even if she sprung this evening on him unexpectedly, he didn't mind, as long as he got to kiss those incredible lips another time.

And just like that, their lips met for the hundredth time. Ashley's arm cupping Selena's cheek, and Selena's arm hugging his small body closer. It wasn't what either of them expected out of their day, but it was what both of them needed. And they continued to kiss long after several minutes rolled by, just laying in the bed together, tangled up in the sheets and their limbs.

Enjoying this new experience, whatever it may be, and for however long it may last.

Later, Outside Ashley's Apartment:

"This...is so...embarrassing!" Ashley grumbled, trying to tug the oversized T-shirt as far down as he could possibly get it to go.

Selena just smirked cheekily, "Hey I think it looks way better on you than it ever did on me."

During the initial disrobing of Ashley the night before, Selena made sure to make quick work of both his shirt and pants by tearing the shirt open, and ripping the button and zipper off his pants when she jerked them down.

So after the two had finally managed to pry themselves from Selena's bed, Ashley was dismayed to discover his only clothes he brought with him were unable to be worn, lest he let the whole world see his bear chest and underwear since neither his pants or shirt could close.

That was when Selena came up with the perfect solution, she could just let him borrow one of her shirts! Since clearly she was several sizes larger than himself, they would easily fit him like a large coat. At least that was what she pitched it as when the idea first came up, only instead of looking like a coat, the long blue t-shirt just ended up looking more like a dress on the small boy than anything else!

So here they were now, walking side by side in the bright light of morning, or rather Selena walking while Ashley semi-limped along beside her due to the achey sensation in his butt from back to back poundings. All the while with Ashley's calves on display since beneath the long t-shirt he had no pants on.

He shot her a pouty look, "Of course you do! Pervert." He teased her earning a nudge from her hip in retaliation as they walked down the street to his building.

"Hey you better get use to my perviness if you're gonna be working for me!" She teased.

Ashley rolled his eyes, "So...I do get the job?"

"Yessss of course you do. But like I said before, don't think I'm giving up on that yoga position, I think it'd suit you well." She said, "I mean, such a sweet petite figure, nnf...gotta fit you into some yoga pants..."

"Selenaaaa stoooop..." Ashley felt like his cheeks had been flushed for the last twenty-four hours straight all because of her.

And he wouldn't have had it any other way.

But unfortunately, they soon approached the outside of Ashley's little apartment complex. The couple walking up the steps to the front door where Ashley needed to unlock to get inside. He fished through his pants pocket, holding his ruined clothes in a bundle in his arm since he couldn't wear them. "You owe me some new pants, and a new shirt by the way!"

Selena snickered, "Well, maybe I can take you shopping tomorrow for some new clothes? If you're up for another date with me of course." She offered. Ashley looked up at her after finding his keys and paused, looking over her face and the sweet little flirty smile she gave him. "Unless I've been way too forward and you're gonna call the cops on me the second you close the door? In which case I would be very depressed." She joked.

Now it was Ashley's turn to laugh, "Noooo, no. You're fine, yeah you were a little...quick to get me home but...I'd be lying if I said I didn't have a great time." He told her honestly, repeating his own nervous habit of brushing his hair over his ear.

"Soooo...date then?" Selena asked hopefully.

And Ashley gave her his best heart melting smile, "Yes, I'd love to."

Then without another word, Selena leaned in for one more kiss. Reaching out to cup his cheeks and pulled their lips together. Unlike many of her other kisses though, rather than being dominant and overpowering, this time she was slow. Carefully methodical in how she parted their lips, coaxing his tongue out to meet hers and playfully batted it around a little bit. Not wrestling with it and not trying to take control, just engaging in a sweet, goodbye kiss before they parted ways.

Clicking their lips with a nice wet smack as they pulled apart, taking Ashley's breath with it. "Call me." Selena whispered while their lips were still close enough to be touching.

Seeming to be unable to speak quite often around her, Ashley just nodded, his signature response to Selena whenever she floored him with her sweeping techniques.

Finally after that, she took a step back, down the stairs, and then another, and another, taking her time to draw out the distance between the two of them. Ashley watching his dream girl the whole way with a look of longing in his eyes. She must've gotten maybe as far as a hundred feet away before she finally managed to force herself to look in another direction and walk away.
Only then did the wind seem to return to Ashley and he nearly swooned again, practically stumbling back into his front door as he fiddled with the keys to unlock it.

Two or three tires later and the doorknob turned allowing him to walk on wobbly legs through the door and shut it behind him, then lean with his back against the cold surface. His hands coming up to clutch at the shirt covering him, and pulling the fabric up to his nose to smell it. And as he hoped, it smelled just like her, that perfume that enticed and titillated his senses with its sweet allure. It made him never want to take it off.

How could he have become so smitten with somebody so quickly? In just one night, he had given himself to a woman he barely knew, but at the same time felt like he'd known her forever. It was insane that he could feel like he was falling so fast and so hard for someone who literally had surprise anal sex with him!

But he didn't care, his heart was singing at the thought of seeing her again. And he slid on his back down the door and onto the floor with a large smile on his face. Blissfully unaware that the same man who spotted him spinning in his apartment was walking by again, and saw him daydreaming with a t-shirt held to his face and no pants on.

The man just shrugged and walked away.

Ashley was too lost in thought to even noticed, all he could do was keep thinking about the fact that he had a new girlfriend.

Who was apparently, suuuuuper into him.

*****

A.N. I hope you all enjoyed that!

This is the start of a loooong story which will undoubtedly explore themes of feminization, crossdressing femboy, and lots of pegging boi butts. I hope you look forward to it :3

Next Chapter: Try out