7. Story Of My Life

~ Audrey ~

“Ouch, ouw ,ouw!”

Audrey yelped and grimaced as she was hunched over the shower. She was attempting to shave areas of her body that she had never touched before. There was a lot of screaming, a little bit of blood, and a whole lot of frustration.

Ah, the things I do for love.

It took her almost two hours to finally finish the job. Once she was satisfied with the result, she moved on to lotion and make up. Audrey was nervous, but more than that, she was excited. She’d read plenty of books about romance, and she had always wondered what making love would feel like. 

Tonight, I’ll finally know. 

By 6 PM that night, Audrey was ready for war. She looked at her reflection in the mirror and smiled in satisfaction. She looked great, she thought. Her long brown hair was curled loosely, her lips were red and plump, and she was wearing a pair of cute lace underwear she bought specially for this occasion. She draped a simple little black dress on top and completed the look with black leather heels.   

This is as ready as I’m gonna get.

Shoving her nervous thoughts aside, Audrey turned to her heels and grabbed her purse. She checked the contents, making sure she got everything she needed. She got her phone, wallet, some make up, a card key to the suite room at the Plaza Hotel, and several packs of condoms.

Audrey had gotten herself on the pill, but seeing as this was her first time, she wanted to be extra careful. All those years of ‘abstinence is key’ really got into her head and a baby, as cute as they may be, was the last thing she needed right now. 

It’s go time, she said to herself as she reached for the door. Time to swipe the V-card.

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“Woah, what is this?” Ashton gaped and dropped his duffel bag on the floor. 

His eyes scanned the marble floor and gold wallpaper all around the room. Audrey stood in her little dress underneath the chandelier, capturing Ashton’s gaze. She smiled a seductive smile, the one she had been practicing all day long.

“It’s our special night, just as promised,” she said as she stalked towards him.

“Damn,” Ashton chuckled, he really couldn’t believe his luck. “Babe, this place is amazing,”

Audrey walked around, circling Ashton’s tall body, and stood right behind him. She put her hands around his neck and slowly slipped him out of his basketball jacket, asking him, “So, how was the game?” and she threw the jacket on the floor.

“It sucked so bad. We got trashed,” he groaned. “I don’t wanna talk about it,”

“Great,” she said as she stood in front of him. “’Cause we’re not here to talk, are we?”

She looked up at him and he looked down at her. His lips twitched into a smirk and his tongue instinctively went to lick his lips as his eyes became clouded. Audrey couldn’t stop the smile forming on her lips as Ashton’s hands landed on her hips. He pulled her closer and his hand traveled to her back, finding the dress zipper. She heard the sound of the zipper being pulled down and she felt cold air hitting her back. The flimsy dress fell and pooled around her feet. 

Ashton stepped back and admired the view. His hands roamed her petite body and stopped at her black lace bra. He let out an appreciative groan as he started massaging her small firm breasts. She tipped her head back and moaned softly. 

“You’re not gonna back out of this, are you?” Ashton asked with his head cocked to the side.

“No,” she said firmly. “Tonight’s the night,”

He smiled at her answer. Not wasting his time, Ashton picked her up with ease and carried her towards the bed. As soon as her back hit the mattress, Ashton’s lips crashed down on her. He kissed her hungrily, like he was desperate for it.

His hands moved to unclasped her bra and he pulled them off of her. His rough calloused hands grabbed her tits tightly, causing her to whimper in pain.

“Ashton…” she protested, pushing him back slightly.

He didn’t mind her protest. He traded his hands with his mouth, his tongue swirled around her nipple and he sucked hard on both of them. His free hands went roam down her body. He cupped her ass cheeks with a firm grip and let out a muffled groan.

“Slow down, Ash…” she said as she sucked in a deep breath.

Ashton did not slow down. He yanked her underwear off completely and staggered back to pull his pants down in one swift move. He hastily kicked them off his legs and pulled his striped boxer underwear off. 

Audrey gasped and took note of Ashton’s length as he started stroking it. They were in a dimly lit room the other night, so Audrey never got a good look at it. He was a decent size, above average, maybe 6 and a half inches. Looking at him now, Audrey could see everything in detail. Everything from the glistening tip to the veins popping on its side.

“C… condom?” Audrey muttered when she saw how hard he was getting.

Ashton fished a silver pack from his pants pocket and grinned, as if to say he got it all covered.

“Hmm, I’ve been waiting for this for so long,” he grunted as he continued stroking.

I bet I’ve waited longer, she said to herself.

After rolling the condom down and pinching the tip, Ashton smiled victoriously and said, “Lay back, babe,”

Audrey nodded and complied. She swallowed hard as he strode towards her and pulled her legs further apart, positioning himself right above her slits. Audrey looked up at him and saw that Ashton’s eyes were hooded with lust. Audrey suddenly felt nervous and scared.

“Hey, wait—“

But before she could say anything, his lips crashed down to hers and he forced his tongue down her mouth, causing her to almost gag. Audrey squirmed to protest, but to no avail. He was kissing her so roughly, Audrey was taken aback. This was not how Ashton normally kissed her. 

Who is this person?

Suddenly and without warning, Audrey felt his tip entering her tight hole and her body jerked in response. It felt weird and uncomfortable, Audrey wanted to move away. Ashton groaned disapprovingly and he held onto her hips and pulled her back, not allowing her to escape this time.

“Ash, it hurts,” she whined as he tried to push himself in again.

“Stay still,” he barked as if it was an order. She was squirming and writhing so much, it was hard for him to enter her. “It’s supposed to hurt the first time,” he said again.

“Ash…” a single tear trickled down her face. He really was hurting her. “Please, slow down…”

Ashton bit his bottom lip and sighed in frustration. He pulled away from her and she sighed in relief. But Audrey’s sense of comfort was short lived because Ashton suddenly said, “Turn around,”

His tone was serious and demanding. Audrey swallowed hard. A part of her wondered if this was too late to change her mind. Audrey could imagine that Ashton would be so frustrated if she did. So although she wasn’t sure about doing this anymore, she chastised herself for chickening out.

No, pull it together! I have to keep going!

And so, Audrey soldiered on. She turned around so that her stomach was on the bed and her ass was sticking out. Ashton gripped her hips and pulled them higher, exposing herself completely to him. Using one hand, he parted her ass cheeks further for easier access. Audrey was squirming again a little, and Ashton responded by tightening his grip.

“I said, stay still!” 

Audrey stayed completely still, wishing he would get this over with quickly and painlessly. Ashton wanted to be inside her quickly too, but the nerves were getting to him, so he got a little soft. He rubbed himself as hard as he could and before long, he was hard again. Not wanting to miss his chance, Ashton pushed himself into her as deep as he could in one hard thrust. She screamed and winced in pain, but he was more worried about getting it in. It took him a little while, but he finally broke her barrier. Once he was completely inside her, blood trickled out of her and Ashton was lost in his desire. His movements were rushed and frantic. He couldn’t help himself.

“Wait, Ashton, stop, it hurts,” she cried.

“It’ll get better. You’re gonna like it,” he kept going relentlessly.

“Ashton… please…”

“Mmm, babe, that feels so good,”

Ashton ignored her cries and pleas. Her voice and tears drowned into the sheets as he kept plunging himself into her. Her nails dug into bed, hoping for some relief, but it only got worse. Audrey scrunched her eyes shut, and though she couldn’t see anything, she could hear everything. The sound of skin slapping and his ragged breaths and grunts.

Ouw. Ouw. It hurts. Hurts really bad.

“Ugh, babe, your virgin hole is so tight, fúck,”

Ouw. Ouw. Please stop. Oh God.

“Oh, “Babe! Oh!”

Ouw. Ouw. Ouw.

Audrey kept her eyes shut and held in the pain. All she could do now was hope that it would be over soon. And maybe the Gods were taking mercy on her, because not even a minute later, everything suddenly ended. It was all over, just as she wished.

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“Welcome to the sinners’ club, sister,” Mikey said in a singsong way.

Audrey rolled her eyes as her two best friends entered her living room. She was lying on her couch in her fluffy onesie pajamas and a wool blanket, doing everything she could to comfort herself after last night. 

Mikey had a bottle of champagne in his hand and he did a little dance, twerking his way to the couch. He was in a celebratory mood, eager to welcome his best friend into the Ho Ho club, he called it. Meanwhile, Olivia shook her head and rolled her eyes, walking behind Mikey with a box of cupcakes in her hand.

“So glad to finally have you on our side,” Mikey gave Audrey a quick kiss on the cheek before sitting down. “Now it’s your turn Liv, get yourself on Tinder or Coffee Meets Bagel and get them bagels,”

“Ugh, ew, I don’t even wanna know what that means,” Olivia shuddered.

“Don’t,” Audrey warned her. “It’s not worth it,”

“What? Was it bad?” Olivia asked.

Audrey was trying to reach the box of cupcakes on the table, but even reaching out her hand made the muscles in her back tighten. She winced in pain as Olivia pushed the box towards her.

“It was… awful. And I was hurting the entire time. The entire three minutes,” Audrey sighed and she finally reached her favorite red velvet cupcake.

“That short?” Mikey asked.

“At least it was short. That was the best thing about that night,”

“That bad?” Olivia asked.

“Imagine someone shoving their entire five fingers into your nose. Just jabbing at it. Now that times a hundred,”

Olivia glanced at her fingers and placed them in front of her nose. She almost stuck them in too, if it wasn’t for Audrey’s quick hand that slapped it away.

“It was like moist flesh rubbing aggressively over an open wound…” Audrey shivered as she remembered the experience.

“Oh, honey, it’s not supposed to hurt that bad, is it?” Mikey grimaced.

“I don’t know, you’ve done this before, you tell me,” 

“Baby girl, we have different holes, different sets of equipment,” Mikey said matter-of-factly. “Did you use any lube?”

“No, was I supposed to?”

“Yeah, if your cat’s not wet enough, or if your man’s not makin’ it rain, you know what I mean?”

“How do I know if it’s wet enough?”

“Girl, you’re barking at the wrong tree here,” Mikey put both his hands up in surrender. “The Lord knows He did not give me those parts,”

Audrey turned to Olivia and the girl only shrugged, “Don’t look at me. All I’m picturing is a cat under the rain,”

It was hopeless asking her two best friends for sex advice. One of them was gay and a thirteen year old girl would be more experienced than the other one.

“Ugh. And it was so awkward... There were limbs… everywhere,” she shuddered.

Suddenly, the thought of Caspian Vanderbilt offering her tips crossed her mind. She didn’t want to admit it, but she was secretly regretting the fact that she never got those tips.

“It’s not Ashton’s first time, is it? Isn’t he supposed to be able to… help you out?” Mikey asked.

Audrey thought it for a moment. Ashton had mentioned that he lost his virginity back in high school. Supposedly, he had plenty of experience with this already. But as she remembered moments from last night, she realized how different Ashton was compared to his normal self. 

“Maybe he was just nervous... I don’t know,” she shrugged.

“Hey, it’ll get better,” Olivia smiled positively. “Just like everything in life, practice makes perfect, right?”

“Does that mean I have to do it again?” Audrey groaned and smacked herself into a throw pillow. “Why don’t you just shoot me in the head and get it over with!”

Her friends couldn’t help but laugh a little at Audrey’s expense. After all, best friends were the ones that would laugh at your misery, but stayed the entire night with you afterward. 

“Damn, for the first time in my life, I’m so glad I’m not a girl,” Mikey huffed.

“And for the first time in my life, I’m so glad I’m still a virgin,” Olivia followed.

Audrey shook her head and buried her face with more cupcakes. As much as she regretted what happened last night, she couldn’t do anything to change that. And more than regret, Audrey was disappointed. She thought her first time with Ashton would be magical. After all, their love story was like something out of a fairytale book.

She was walking mindlessly down the halls at school one day, and a guy bumped into her, causing her to drop her books. He helped her collect her books and introduced himself, “Hi, I’m Ashton. Nice to meet you… or to bump into you,”

He had one of those smiles that could get you weak in the knees. It was impossible for Audrey not to shook his hand and said, “I’m Audrey. Nice to bump into you too,”

Ashton was like one of those prince charming guys she would about in books. He was sweet, caring, and ambitious, everything she wanted in a man. The past six months with him were some of the best times of her life. She had such high expectations, so it was a huge letdown that the sex turned out to be… blah. 

Oh, God. I’m so going to hell for this… and I didn’t even cúm.

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- - - - - To Be Continued - - - - -