Born to Be Ch. 07

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After losing the bet, Ashley has to face the music.
14k words
4.61
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Part 7 of the 12 part series

Updated 10/06/2023
Created 03/07/2019
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A.N. Return to the strap on!

If this isn't my favorite chapter so far, it's definitely one of my favorites x)))

Buuuut chapter 8 is preeeetty awesome too ;D I know I'm a whore.

The Following Contains: Interracial between a tall black lady and a crossdressing femboy. Which in conclusion creates a formula of strap on penis being inserted into femboy bottom. Also with toy play of the buzzing sort. Solve for X.

Please enjoy :3

*****

The night was pretty restless for little Ashley, after the intense wrestling match between himself and Selena, when the afterglow of the sex wore off and the two of them went to bed. His eyes were wiiiiiiide open in horror as he realized what a complete dummy he had been for challenging her to a wrestle. And also the consequences of the bet, what he'd have to do loomed over his head throughout the whole night.

What little sleep he got was wracked with images of his sadist girlfriend terrorizing him all day with a vibrating instrument of doom. And when he awoke, he could literally feel her eyes baring down onto the side of his face over him.

Normally Ashley was the one to wake up first with Selena sleeping in, not as much of an early bird as he was. But the tables certainly turned today as he felt her imposing form leaning over him, grinning down at her tender morsel she was about to spend all day defiling with just the push of a few buttons.

He tried to pretend he was asleep for as long as he could, thinking that he could hold off this daunting task as long as possible. But the alarm clock definitely wasn't going to allow that to happen.

Plus, it seemed as if Selena was awake and ready to slap the alarm off immediately, because when it sounded, it only rang for maybe a second before he heard her turn it off. Then the weight of her on that side of the bed slowly shifted over to linger right over him. She was leaning on her elbow and looking down on his tiny form, trying to fake his way out of getting up.

And for a moment or two, it seemed like that might happen when she didn't immediately try to rouse him. Ashley foolishly getting his hopes up only to have them bombed out of the air at the sound of her voice. "Goooood mooooorniiiiiing." Selena's grin possibly could have fooled a passing bystander, appearing to be innocent and nothing more than a bright, white smile of kindness.

However, after living with her for several months, Ashley had easily identified it as a ruse. That smile she stared at him with was full of evil intent. The intent to devour, destroy and consume.

I made him tremble in sheer terror and sooomewhere deep down, delight. "Good... good morning...honey..."

"Biiiig day todaaaay..." She said, her fingers dancing through his hair. "You ready?"

Ashley tried to think up an excuse, to say anything other than the word yes in that moment. His imminent fate seeming so close now, "Would...you believe me if I told you I had an upset stomach?" He made up on the spot.

"Hehehehe! Nope!" Selena shot him down and slapped his butt, "Now up! Up and at'em. Big booty filled day!" She mocked him, hopping up and out of the bed over his body. Poor Ashley whimpered and tried to just dissolve into the bed, hoping maybe he would phase into the mattress and Selena would just forget about the bet. "Cooome oooooon no hiding!" The blankets were yanked away! Flying off the bed spectacularly, exposing Ashley's naked, curled up form. She was like an excited child trying to rouse her parents from sleep on Christmas morning!

Once again Ashley whined at her, "You don't have to be a weenie!"

More excited laughter from Selena, "I won't be a weenie if you stop being a butt!" She countered him with, "Now up! Don't make me pull you out!"

"Hnnnnnggh!" Ashley again whined, "Babyyyyy..."

"Get that cute butt up and out missy!" He felt a quick swat to his bottom, jolting him, "I'll do it, you know I will!"

"Ugggh!" Ashley groaned finally unfolding himself from his fetal position. "I'm up I'm up!" Selena tossed the bundle of blankets back onto the bed as a huffy puffy Ashley sat up and hopped off the bed in his little pink, silk nightie. Crossing his arms in an adorable pouty face, framed by his beautiful locks of bed head hair. "You're so mean."

She shrugged, "Don't be a sore loser babyyyy, I won fair and square, and now you know what it's time for..." She looked at him with those predatory eyes.

Ashley quickly hopped by her, "Wait wait wait! At least let me get dressed!" Putting his hands up in defense, ready to ward off her should she pounce on him. "I have time for that come ooonnn Selena please!? I just woke up please let me get dressed." He was already on the verge of begging her. Her sadistic tendencies giving the poor thing a fear boner in this moment, thankfully hidden in his matching silk g-string.

And although she didn't back off right away, slowly stalking closer and closer to the petite girly boy, practically herding him up against the wall. She could see that he was a little scared to jump right into this dirty act without at least being given a moment to take a breath.

So after a lingering moment of tenseness between them, she leaned away, "Fiiiine, go ahead, but no more stalling! We do have to go to work."

Ashley let out a breath he didn't realize he was holding and hastily rushed off to the bathroom like his life depended on it. "Thank you!" He whispered in a rush before getting inside and slamming the door shut and locking it.

Selena crossed her arms and waited a few seconds...then saw the door slowly peak open. "Need clothes?" Ashley's face was red as a tomato as it sheepishly nodded. His girlfriend chuckled and walked straight for the closet, rummaging around for a bit before returning with an outfit in hand.

He half expected her to approach him with the teeniest tiniest pair of booty shorts and crop top they had, but thankfully that wasn't the case. She chose a rather tame pair of purple yoga pants and milky pink tank top. She also didn't immediately reach in and try to yank him out or reach for him which was a good sign. Perhaps she really was willing to let him breathe for a few minutes.

And he did breathe! Very heavily for several minutes, leaning over the sink, this was so nerve wracking! His hands were shaking while he undressed and slipped into his work clothes, practically moving one inch at a time into them. He thought about trying to shower to extend his time, but the fact of the matter was, he was actually on a time limit here. They needed to be at work in less than an hour, so the clock was ticking on how long he could actually stall and prevent his fate.

He even messed up putting on make up a few times and had to redo it do to his jittery limbs. "Come on girl...relax...you can do this..." He tried to finish his eyelashes. Looking at himself so closely in the mirror. Ashley took a deeeeeeeep breath, held it for a few seconds...then blew the air out his lips. "Okay...you got this." He said to his reflection, nervously trying to pump himself up and failing pretty bad. The poor thing couldn't remember the last time he had been so nervous!

Maybe their first night together comes pretty close.

He had been stalling in the bathroom for as long as he possibly can. Although Selena was certainly not letting him get away with it unscathed. She lingered outside, close enough so that he could hear her heels clicking outside the door. Knocking obnoxiously every few seconds, "Hurry uuuup babyyyyy... we're gonna be late for woooork. You can't stall forever."

"One second!" He called back, hand trembling as he lifted the lip gloss up to his mouth and swiped the brush over his lips. "I'm just...trying to make myself look good!" He made up the excuse, trying to distract from the task which lay before him.

A full day...with a big butt plug...up his butt...

"Remember that time I said you can't be late because I'm your boss and I decide when you go in?" Selena called out again, "Welp I'm cashing that boss card in noooow."

Ashley hopped up and down so nervously, his body a tingle of goosebumps and rampant nerves that felt like an adrenaline shot. "Hnnnnngh!" He whined again, "Okay okay I'm coming!" He finally caved, touching up the last few traces of his beautified face and putting the rest of the makeup away.

With the yoga pants tight to his legs, he spun around and went for the bathroom door. Hand trembling as he grabbed the knob and pulled it open. Immediately coming face to face with not Selena. But the large, purple butt plug, swollen around the base where the electronic component was inside it to vibrate at the press of a button.

His eyes went about as wide as its widest point as her fingernails tapped tantalizingly on the toy. Grinning with evil glee, "Here's your loser prize..."

Each tap practically made Ashley flinch in fear, every nail's click ringing in his brain like a ticking clock. Counting down his hours to live but moving much faster than seconds, his heart beating like a jackhammer with it's rapidness. And for a moment he felt the instinctive desire to just shut the door, but a quick glance downward would show that Selena was smart enough to step into the doorframe so that her feet would block it should he try to shut it in her face.

"Oh my Gosh...oh my gosh..." Poor Ashley was so scared, so nervous, so much so that his little clitty was hardening in his yoga pants. The fear boner becoming stronger and stronger with each second.

"Come along now..." Selena reached out and took hold of Ashley's wrist, gently tugging him by the arm, out of the bathroom and into the bedroom.

He moved like his body wasn't his own, like he was standing outside of it and just watching someone else puppet him. Guiding him over towards the bed and pushing his form gently towards it. He spun around so he was facing Selena while she stepped along with him, a look of pure evil on her face.

"S-Selenaaa um...is there anyway we could t-talk about this?" Ashley stuttered as he re-entered his own body, entering the pleading stage as he felt his thighs hit the back of the bed.

"Nope!" She instantly struck that hope down, tapping the huge plug against her palm now like a baseball bat she was about to batter her frail little girlfriend to death with. "Turn around and bend over bitch." She grinned, "Momma's about to get the spoils of her victory..."

Ashley just wanted to crawl out of his body and vanish his essence into the Ether of the universe. It was going inside him, that GIANT THING was going to be in his butt all day long, with his sadistic girlfriends finger on the vibrating trigger.

He'd had butt plugs put in his booty before, courtesy of his kinky girlfriend, but none nearly this big, and definitely not vibrating ones. And also not in public! They were breaching a lot of taboos all at once here, and his insides quivered in both fear and reluctant delight. His petite frame turning almost robotically around for his demanding amazonian girlfriend.

"I...I'll pay you ten dollars to please go easy on me..." He begged now facing away.

"Hands on the bed." This time she just straight up ignored his plea, and went on with the next command. Ashley pouted, even though he knew she couldn't see it, he still felt like showing his embarrassment and how much it was affecting him, But once again, he did as she commanded and leaned forward, placing both palms face down on the bed, bending over and perting out his ass towards her. "There we go..." Selena suddenly reached out and snatched the waistband on his yoga pants and g-string, then yanked them both straight down over the curve of his ass, earning a surprised squeak from him. "Spread those little legs..."

"Hnnnnnngh..." The typical Ashley whine squeed it's way out of his throat as he did what she told him to. Separating his shapely limbs so that his ass was spread open and welcoming her in.

"Heehee! Hmmmm..." She took a good close up look at his ass then, kneeling behind him and placing her face right beside his right cheek. One hand reaching up to feel the smooth skin while her lips kissed the soft cheek.

"T...t...twenty dollars?" Ashley could feel his legs shaking, "Oh God...she's so close...it's so close..."

He could hear the drawer being pulled open beside the two of them, "Sweetieeeee...you're only making it worse for yourself..." She tormented him, enjoying this far too much. He really needed to double check the fine print for every bet they made in the future.

Risking a glance over his shoulder, he could see she had pulled the large bottle of lube they kept bedside out of the drawer and flicked the cap open. He could at least take comfort in the fact that she was going to lube him up before diving in. And she wasn't just licking him like she did when they normally had sex. She probably knew he'd need the extra slipperiness of lubricant since it was going to be a long haul today.

Following her uncapping it, he felt the first kiss of the cold liquid spilling onto his ass crack. Slowly being drizzled onto his hole, followed by her fingers rubbing it in a bit. Ashley bit his lip, the sensation of warmth from being touched there despite the cool temperature of the lube was always so pleasant. He expected her to push her fingers inside to guide the lube in deeper, but she surprised him by instead placing the mouth of the bottle directly against his wet entrance and applying a little bit of pressure. The tip entering him just a little bit, Ashley's eyes going wide at the odd object firmly kissing his entrance.

But then, she squeezed the bottle, and that cold fluid then squirted directly into him. And that...felt strange.

A good strange...but still a little strange. Enough so that Ashley squeezed his eyes shut and gave a tiny, "Ouu!" In surprise when he felt it, the cold slimy substance entering his warm body and slowly sliding into his depths, coating every one of his walls in it's slickness. It actually made his toes curl into the carpet, his clit throbbing with it's hardness which Selena had thankfully chosen not to comment on and embarrass him even further.

An ample amount was inserted into him, Selena squeezed that bottle for a good ten to fifteen seconds before finally pulling it back and dabbing even more on his star. He didn't know how much she put in him, but when he first saw the bottle it was full a moment ago. And peeking behind him again, red faced and panting, he could see that the contents had gone down quite a bit. His face flushing even further with how much of that thick liquid he had just taken inside him.

But he wasn't out of the woods yet, he could now see her drizzling the lube over the butt plug. Spinning the material around in her fingers to coat every inch of it, rubbing it in and smearing it all over even the tiny neck of the pug, then adding some more. She was truly using a large amount of lube for this, more than he's ever needed before.

Then...she got off her knees and stood up...

"OhGodohGodohGodohGod!" Ashley's hands gripped the blankets in a death lock, his heart racing faster than ever before. This was the moment, he looked forward, unable to watch his imminent doom heading for his asshole.

He could feel the weight of her knee pressing on the mattress beside him, followed by the presence of her body coming down and looming behind himself. Ashley couldn't recall the last time he was so scared and turned on.

Her teeth nibbled onto the side of his ear, and he heard Selena's sweet little giggle echo through his brain, setting every nerve on edge and every goosebump on his flesh to rise up. He squeezed his eyes shut, dreading and dying for the entry to happen.

However to his shock, he didn't feel the push. Not even the light touch or tap of the toy on him, just Selena coming in close behind him.

"You know honey..." Selena leaned over his shoulder, the tense Ashley peaking open an eye as the penetration he was waiting for was yet to come. "I know we made a bet, but I love you more than any silly plug play." She said with a reassuring smile. "And I know I've been teasing you but if you're really not into this, we don't have to do it. I'd rather forgo the whole bet than actually make you uncomfortable in doing something you don't want to do." She offered, a comforting hand rubbing his back.

It took him a moment to open both eyes and look over at Selena's genuine stare, "You...you mean that?"

She nodded, "Of course. I can see your nervous, you've been shaking this whole time. And we can always do something less kinky if you're not ready." She leaned in to kiss his cheek, "Honestly, it's okay."

There were a few moments after that of just silent breaths between them, until slowly but surely, Ashley finally came down from his tensed up state and let out a sigh. His body relaxing and moooost of his worries quelled. But now that she had told him this, another thought came up in his mind. "Well crap, now I have to do it!" Ashley lamented in his mind, looking into those big brown orbs. The fact that she was offering this way out to him, content to do anything else to make him feel safe and secure warmed his heart. How she was willing to give up her prize just to make him happy.

He loved it...and kinda hated it. Because looking at her face now, so sweet, kind, and genuine. He couldn't kill her fun, and even though he was super nervous, it wasn't EXTREME nerves. With his heart pounding telling him to get the Hell outta there. It was excited nerves, butterflies if you will.

So he blew some air upwards, causing some bangs to drift in the wind. "Just put it in my butt already." He said with a shake of his head.

"Are you suuuure?" Selena teasingly gave him oooooone more chance to back out.

"Yes! Just do it please before I change my miiiiind!" Ashley whined again.

She raised and lowered a shoulder, "Very well baby...here we go..."

And that's when he felt the first touch, the size of the plug practically mimicked the strap-on cocks she used on him a million times. Both in length and in girth, only maybe just a few inches shorter...maybe? He was sure he'd be able to tell when it was all the way inside him that's for sure.

He blew more air out of his lips as she rolled the plug over his hole, gently pushing...pulling back, then doing it again. Repeating this a few times, with extra care to loosen him up, make his little pussy weaken, make it want to accept her gift. She always provided it with such sweet things, so of course it would gladly open up for her.

It felt nice, like always whenever she played with him back there. He bit his lip, waiting for when the pressure became more than just gentle pushes, he knew it was coming...just had to wait for it...wait for it...wait for it...

When Selena finally decided now was the time to insert it, she gave the plug one more good twist so that it practically corkscrewed its way inside of him. The lube around every corner only helping it to begin slipping its way along. Ashley felt the first push, and it felt veeeeeery much like Selena's cock starting to fuck him. The tip was different though, rather than shaped like a mushroom it was smooth, similar to the pink dildo they used on occasion.

Only it didn't just stay a single girth though...it widened, after the first couple of inches it grew wider...and wider...

"Nnnnf!" Ashley squeezed his eyes shut again while Selena softly shushed him. It was probably gonna be the thickest thing he'd taken yet, even though it was only a little bit thicker that her black dildo. It was still a step up and was going to be a stretch for the poor girly boy.

Eventually, she got to the fattest point on the butt plug, he just needed to get through this part and it would slip right in and stay nestled inside. "Okay baby...just one more push and you take it all..." She whispered beside him. "Are you ready?"