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Breaking in Kira’s Ass

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Kira shivered as she read the request. There was nothing noteworthy about the invitation itself, but the reputation of these clients preceded them. They were a group of business guys who threw these parties, hired escorts, and were known for their love of anal sex. The girls Kira worked with only had positive reports from working those events, but she hesitated.

Short and full-bodied, Kira had been told her entire life that she had an amazing ass. She had a small, defined waist and her smooth round butt cheeks that swelled lusciously from her flared hips. Although she had always loved sex, Kira had always been wary of anal. Raised in a religious and conservative home, she had ingrained beliefs about it being “dirty” and sinful that still bothered her long after she had abandoned those beliefs.

She was a near anal virgin, except for an instant after her high school graduation party. Kira’s high school boyfriend had been significantly more experienced and he had wanted to have sex. At the age of 18, Kira was still clinging to the belief that she would “save her virginity” for marriage. Another girl in her class had told her about having anal sex as a substitute and said it had felt good, so Kira agreed to give him her “other” virginity. When they tried, he excitedly bent her over the side of his bed and unceremoniously pressed the bulbous head of his cock into her anus sharply. She had cried out, but he thrust sharply in again. She tried to tolerate it, but after it felt like he had fed his entire manhood into her tight backside she couldn’t help but whimper “Are you all in?” “Are you kidding me,” came his reply “you’ve got about 2 inches of me.”

Kira quit anal then and there and decided she preferred blowjobs.

Since completing her BA coursework, Kira had moved to a new city and was loving the attention and fun that came with her life as an escort. Her resolve to preserve her virginity had quickly crumbled in college. It was inevitable- Kira loved to have sex and relished having lots of it with several boyfriends during her time there. Working as an escort, she got paid to see the city and to do what she loved most- fuck.

Still though, sex work had sometimes been difficult when it came to her reluctance around anal. She found that her clientele were respectful but that she couldn’t give them the experience they wanted when so many of them asked for it. It frequently cost her at least a couple of hundred bucks when guys had gotten particularly insistent about putting it in her butt. They loved to squeeze and rub and kiss the firm globes of her ass, but as soon a tongue, finger or thumb brushed too close to her small opening, she always immediately redirected them.

Kira decided to go to the event and stand her ground. She felt slightly nervous about being propositioned for anal but took comfort in her colleague’s feedback that the partygoers were known for being pleasant and respectful of the escorts boundaries. She wore a tight, low-cut top that showcased her large, soft breasts and tight jeans that the top of her buttocks inevitably spilled slightly out of. The party had a relaxed atmosphere and before she knew it, she had an interested customer. Casey, a dark haired ex-rugby player in his 40’s, had worked in real estate for years in New York and had recently made a successful move to their city. The two of them had a couple of drinks bahis firmaları and headed up to the hotel room.

Kira was actually totally excited to fuck this guy. He was hot and she was making $500 an hour to let him do her. Her excitement turned to dread when she heard him say “So…I hope you like anal play.” She felt a pang in her chest as she exhaled sharply and prepared to launch into her usual elevator speech about her limits, but then she thought to herself that this rule had started to really cramp her business.

“Let me think about it for a minute,” said Kira.

“If it makes a difference- I’m pretty great at it. And I’ll pay you more.”

“Here’s the thing,” said Kira “I’ve only ever tried it once, years ago, and I don’t like it. I find it painful.”

“I get that it’s intimidating at first, but if you get through the discomfort, I think you’ll find you like having my cock sliding in and out of your tight, hot ass. I’ll pay you $3000 for the pleasure.”

Kira felt herself get wet when he said that and couldn’t believe what she was hearing- $3000 to finally try anal. She could tolerate it.

“There’s a caveat, though.”

A caviat? She was about to get fucked in the butt. There was more?

“Before I really go in and fuck you good, I’ll lube you up. I’ll stretch your delicate little hole with my fingers and I’ll get you all ready for your anal fucking. But I also love inflicting a little pain with pleasure…I especially love the sensation of breaking in an unprepared, unopened ass with my cock. So before your asshole gets a little love, I want to shove in all 8 inches in one hard thrust…with no lube. It will hurt, but it will be over in just a moment. And then I’ll pull it out and the easy part will start for you.”

Kira felt her stomach turn and a chill go up her spine. She remembered her college boyfriend trying to stuff his dick into her that time and wanted to say no, it was too much. But with $3000, it occurred to Kira that she could afford to take a trip to Milan with her roommate that Spring- she had missed the last 2 annual fashion shows there because of the expense. She reconsidered.

“Okay,” Kira said, trying to keep her voice steady “I’m down.”

Casey looked overjoyed. He led Kira into the bedroom and stacked two pillows on top of each other on the bed.

“I want you to turn away from me, drop your jeans, and slowly step out of your underwear.”

Kira did so. Casey knelt behind her and began to knead her buttocks. He grabbed handfuls of her ass and rolled her cheeks apart and smooshed them together. She could feel him looking at her anus as he dug his fingers into her supple flesh and pulled her buttocks apart. He examined and touched her for a few minutes before telling her to lay on the bed with her hips resting on the pillows. Kira laid facedown over them so that her ass was in the air and Casey knelt behind her. She shivered, anticipating how this would hurt.

Casey savored the sight of her tight, pink, star exposed and offered to him, thinking how in a moment it would be violently opened and stretched wide to accommodate him. He rested the head of his steel-hard cock against her puckered hole and began to push in enough that he wouldn’t slip out when he slammed into her rectum. Kira tensed as she felt the pressure on her asshole as he bore down. She gasped as her kaçak iddaa ring began to stretch to accept his head and continued to groan as it pushed past her clenched muscles.

When just the head was inserted, Casey said “I’m going to shove my dick up your ass now. You’ll suffer less if you relax your muscles. Last chance to back out.”

Kira whimpered as she shook her head no and tried to relax. Having received his confirmation, Casey shifted his weight and tilted his hips down, his cock head still sticking erotically out of her ass. Then he thrust hard, his girth ripping past Kira’s resistance and surging roughly into her rectum. She tried to scream, but no sound came out. It felt like someone had shoved a baseball bat up her ass. She could feel him inside her, spearing her and filling her ass to an overwhelming degree. Her anus was on fire. Kira could hear him breathing raggedly, completely enraptured by the feelings of dominance and her virgin, unprepared ass struggling to contain him.

“Oh my god, Kira,” he said “your ass is incredible.”

Kira couldn’t even respond. Casey gently whispered “I’m going to pull out now.”

She felt his dick pulling agonizingly at the walls of her anal cavity as he withdrew and it stung badly. It had been worse than she thought. Still, she thought, the worst was over now. Casey sat back and began to rub her reddened but still tight asshole with his thumb. It hurt, but felt strangely erotic after the assault. Kira moaned quietly, surprising herself. After her anus got used to being touched, Casey began to put more pressure on it, gently dipping the tip of his thumb into her. She liked it, and subtly pushed her ass back against his digit to accept more. Casey took the invitation and withdrew his thumb, replacing it with his index finger. After circling her asshole for a moment, he pushed his finger back into her passage.

Kira cried quietly, as her rectum was still tender from being forced open a few moments ago, but after a minute or two, she began to push back against his finger again. Casey smiled to himself. Women who say they don’t like ass stuff have never tried it properly. He began to wiggle his finger in her butt and Kira shifted slightly at that discomfort. Casey decided a little discomfort was good for her and added a second finger.

“Not yet,” Kira protested

“Just trust me.”

His two fingers quickly disappeared between Kira’s perfect bubble butt cheeks and found her anus. Casey inserted them with slight effort as she tensed and groaned at the alien, uncomfortable sensation. Despite her anal cavity’s resistance, he began to twist and spread the two digits, slowly opening her up. It hurt a little, but there was some pleasure. Soon, Kira began to hope that he would add another finger, but Casey was ready to fuck her ass. He reached over to the night table and produced a bottle with a long, thin tip. Smearing vaseline on it, he placed the tip in Kira’s asshole.

“What is that?” Kira asked

“Lube,” Casey said, “You’ll like this stuff.”

She felt a surge of embarrassment as Casey inserted the thin, slick nozzle a couple of inches into her back passage and squeezed out a load of lubricant. She felt the cold substance flood her rectum and shivered. He removed the syringe, inserted his cock head into her now loosened butthole, and leaned over her body, supporting himself kaçak bahis on his elbows.

“Slow this time,” he said.

And at a snail’s pace, Casey began to lower his hips and slowly slide his stiff pole into Kira’s slick, twitching anal canal. He stopped for a moment when he was roughly 3 inches in and allowed her to get used to being stretched. She was grateful that he was so attentive as her butt was still sore from being violated before. She felt so full, but this time, she felt a velvety warmth and excitement build in her stomach as he slowly, centimeter by centimeter, fed his thick penis into Kira’s rectum.

When she felt his pubic hair tickling her butt cheeks he paused again, she sighed with relief as she realized she had taken in all of him. The sensation of having a cock in her ass felt more distributed throughout her body- especially her legs and stomach- than when she had one in her pussy. It was strange and overwhelming, but the fullness was intense and intoxicating. Kira’s anus and rectal walls were only slightly sore after Casey’s digital massage and all the lube, but she was shocked to realize that the stinging had begun to feel tingling and deeply erotic.

After a moments pause, Casey lifted his hips, slowly withdrawing most of his throbbing rod from from Kira’s lubed-up chute. Jesus, her ass felt like a hot, silk-lined vice. As he pulled out, she couldn’t stop herself from moaning quietly in protest. She could feel Casey smiling at her pleasure and pushed her face into the bedding to hide her shameful blush. His dick stiffened even more when he stopped to examine Kira’s adorable, spread asshole strangling his cock and framed by the most gorgeous, fleshy globes Casey had ever seen.

Kira was whimpering with anticipation. Casey dropped his hips again, firmly but gently reinserting his length. She squealed in delight that time as a delicious jolt ran from her stuffed ass, through her stomach, and up her spine. He began to fuck her ass, steadily at first and then varying his speed and force. Kira pushed her ass back against Casey, trying to take as much of his dick into her butt as she could. The exquisite stretch made her greedy. Her favorite was when he would withdraw achingly slow before slamming roughly back into her bowels. The mixture of pain and luxurious fullness blew Kira’s mind. She reached beneath her and began to rub her clit; she immediately felt her climax begin to build.

When she came a minute later, Kira felt her rectum spasm, squeezing Casey’s cock in rhythmic contractions as she gasped out sharp, ecstatic cries. The sight of Kira’s ample asscheeks jiggling as she came and the sensation of her back passage milking his dick sent Casey over the edge and he exploded into her, shooting a hot load deep into her truly devirginized ass.

*******

The experience was amazing and the money was great, but Kira always remained conservative and discerning about who she had anal with. It never did become part of her standard repertoire. Kira left sex work 2 years after her anal deflowering to get serious and commit to a new relationship. She married Todd a year later, a successful accountant who was boring, bald, and dependable, and the two of them moved to the suburbs. Friends of Kira’s sometimes wondered how Todd could have possibly made her happy, but he always smiled inwardly when her vivacious beauty outshone him at parties. After all, some of the other wives there maybe like anal, but he was probably the only man in the room who could say his wife loved a 10 inch cock shoved up her perfect, un-lubed ass as foreplay.

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