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"A newly divorced woman loses her anal virginity at a festival"

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Sophia caught herself smiling, and while she usually wasn't the most expressive person, she wasn't about to feel bad for enjoying the spontaneous festival experience. The performances were grandiose, with thousands of fans singing and dancing along, but she couldn't bring herself to completely ignore the sadness she felt after ending her marriage.

Almost everyone was half-naked, especially the younger, more daring ladies that wanted to show off their bodies in lingerie and other skimpy outfits. As for her, she didn't have a special outfit for the occasion but didn't want to be the older prude in the crowd, so she decided to leave her pants in the car and make the most out of the last-minute tickets by attending the event in her work blouse, lace thong, and heels.

She carried several extra pounds on her, but her body type was generous in distributing most of it to her ass and thighs to give her a curvy look. However, standing amongst mostly younger attendees, she felt a bit self-conscious about her figure, but nothing that could damper the new aura she had gained after finalizing her divorce that had her wanting to make up for lost time and push her limits.

As the performers on the stage said goodbye to the crowd and gave way to next band, a shirtless stranger walked up next to her and asked, "Hey, what's a MILF doing here all by herself?"

She turned to him, taking a moment to scan him from head to toe, noting his toned abdomen before answering, "Uh, excuse me?"

"Sorry, ya know, just here with my friends and I'm the only one without a date," he explained, clearly showing signs of having downed a few beers.

"Okay, and I'm supposed to believe you're interested in me out of all these girls?" she asked, doing a look around motion with her hand.

"With an ass like that, yeah, I am," he said, continuing to display the boldness that was aided by getting lost in the large crowd and plenty of alcohol.

"What's your name? How old are you anyways?" she asked, relieved that the flashing lights concealed her blushing face.

"I'm Nolan, and, er, old enough to know you want sex tonight," he replied, igniting a spark of arousal between them.

"Oh, is that so? Well, I'm Sophia, and my band is about to come on," she said, giving him a friendly smile that eased his nerves. "You can stick around if ya want."

Not wanting to seem like a chicken in front of his friends, he stayed by her, and watched the performance that naturally eased her into his arms with his bulge pressing against her ass. When her favorite song came on, he worked his hand up her torso, fighting the urge to fondle her and instead caressed her until he worked up the courage to slide his fingers into her mouth.

I want this, I need this, just gotta accept it, she thought, reminding herself that she was a woman free to do as she pleased.

She sucked on his fingers almost involuntarily, lubricating them just like he wanted while he moved her thong aside with his free hand. He slowly removed his fingers from her mouth and brought them all the way down to rub them over her exposed rear entrance.

Her warm flesh melted onto him, giving her kinkier side the opportunity to ask, "So you're an ass man?"

"Fuck yes, I love it," he replied, pushing two fingertips past her sphincter.

She gasped at the intrusion, and said, "Ya know, I'm newly divorced...and I've been wanting to try new things."

"You deserve a good time," he said, holding her tightly with his arm around her waist to push his fingers in deeper.

For the remainder of the band's performance, she adjusted to her new persona while he continued fingering her ass and loosening it up for the real thing.

By the time the band was walking off stage to thunderous applause, she was the one taking charge and leading him to the parking lot. They looked around, unsure of where either of them had parked, and soon gave up in favor of getting between two trucks that gave them the most privacy.

Unsure of how to begin, he leaned forward for a kiss, but she rejected him by placing her hands on his bare chest, "No, I'm not ready for that, sorry," she said.

He smiled, realizing the irony of her decisions, but opted not to trouble her and instead pulled down his shorts to unleash his raging member. She held it in her palm and let out a glob of saliva that landed mostly on his shaft then spread it evenly over his length.

Just as she was going to turn around to get herself in position, her long-repressed wantonness took control of her body and convinced her to make the most of the moment. She took her time running her hands over his abs, noting the contrasting hardness of them against her soft hands, before settling on the concrete below her and opening her mouth to seal her lips around his girth.

"You naughty, fucking MILF," he said, watching her devour his length. "I know you've been wanting this."

She responded by upping her rhythm, stopping only to spit on his shaft to lubricate it sufficiently. He was right, she had always enjoyed busying her mouth and rendering a man defenseless against her prowess.

If solely up to her, she would've continued for a while, but the impromptu scenario had them in a controlled rush. Once she got her oral-craving fix, she bent over against the truck in front of her and presented her ass for its first-ever back door penetration.

He got behind her, salivating at her flesh, while using one hand to spread out her right ass cheek and the other to guide his tip over her circular opening.

She looked up at the night sky, something she loved to do whenever possible, but this time it was about soaking in the moment as a young stud she had just met was about to do something she had never done in years of marriage. She felt liberated, with no inhibitions weighing her down and finally doing something entirely for her pleasure.

"Hmmnngg," she moaned, feeling his tip stretching out the entrance of her unexplored cavity.

He gave her a moment to adjust to the new sensation of pleasurable pain, and gently ran his hands over her ass cheeks to reassure her that he wouldn't hurt her. To his surprise, it was her who pushed back to get more of his inches inside of her.

With half of his length gripped by her tightness, he pulled out most of it and pushed it back in tenderly. He repeated that a few times, each time giving her more length until it entirely disappeared into her seemingly bottomless hole.

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"Ohhmm, fucckk," she cried, questioning why she had denied herself this pleasure for so long. "That feels so good."

Guided by her body's reaction, he confidently began thrusting into her and alternated spanks on her cheeks, turning them bright red in the process. The licentious ecstasy running through her body manifested itself in the way of her juices running down her thighs.

Any hint of pain was gone, giving the newfound stimulation free rein to build a distinct orgasm deep within her core. The repeated friction on the back of her erogenous zones gave her a quivering feeling in her lower belly that made her sopping, swollen pussy jealous for attention.

"You have a perfect ass," he complimented her, squeezing his fingertips into her soft flesh to show just how much he meant it.

He was mesmerized by the sight of his dick disappearing and reappearing between her ass cheeks. He had set out to fuck the lady with the nicest ass he could find and while he had done that, she was a woman nearly twice his age. He wasn't one to complain, not when he was a huge fan of older women who were willing to push their boundaries.

"Damn, bro, fuck her guts," they heard from behind them, from someone who had walked by without them noticing amid the attention they were giving each other.

He smiled and increased his tempo, switching to faster, shorter strokes that targeted the backside of her G-spot. Her knees buckled and her sphincter clenched around his shaft as her pussy released a short but strong gush of her juices.

"I'm gonna come, I'm gonna fucking come," she warned, feeling a collapsing sensation inside her gaped hole.

He clenched his teeth, mustering the last of his sexual energy to delay his orgasm and give her a few more strokes to push her over the edge.

"Ahhmmnngg, fucckkk," she moaned, welcoming the distinct waves of her first anal orgasm crashing against her body.

Her orgasms were normally accompanied by plenty of squirting but this one was different, it felt more profound and remained at its peak for much longer than her vaginal orgasms. The unrelenting pulsing in her core nearly made her black out, making her legs tremble and both of her holes spasm as if her body was surprised by where the climax had originated.

The repeated contractions forced him to give in, "Uhmnngg," he moaned, contorting his face in response to his load emptying inside her one spurt at a time.

As their bodies returned from their orgasmic heights, he pulled out of her reluctant grip and watched as she quickly fixed her thong to stop his load from oozing out.

She turned to face him with a disheveled yet satisfied look on her face and said, "That was...unbelievable."

"Yeah, it was. Did it hurt?" he asked, following her every move and expression as he pulled up his shorts.

"Hmm, a bit at first but then it felt really, really damn good," she said, unable to hide her smile as she felt she was being interviewed after a porn scene.

He stood frozen for a moment, caught between feeling triumphant and dejected that it was over, then as a Hail Mary of sorts, he closed in for a kiss once more. This time, she allowed his tongue to introduce itself to hers, and he made the most of it by reaching behind her back and getting another serving of her ass cheeks. He palmed them before spreading them to allow his warm load to drool out of her reddened, gaped rear entrance and onto her thong and his fingers. He got as much of it as he could and brought his coated fingers up to her mouth, similar to what he had done while her favorite band was on stage.

She hesitated, not because she didn't fancy the kinkiness but due to her arousal plateauing. She looked around to make sure nobody was near then opened her mouth to clean his fingers, the same ones he had fingered her with, of the cum that had filled her first anal creampie.

"You're really dirty," she said, licking her lips. "But you taste so good."

"Will I see you again then?" he asked, bringing his fingers between her legs to rub her pussy through the soaked fabric of her thong. "I know you want more."

She wasn't ready to answer, so she bought herself more time by resuming their kissing, which for being strangers, showed a display of passion that she hadn't felt in years. After everything that had transpired, seemingly in a blur, she accepted that her new persona was willing to have an ongoing sexual dynamic with someone who made her feel wanted, even if he was much younger.

"You got your phone with you?" she asked, comfortably admitting to herself that she was doing no wrong and it was okay to pursue a sexual adventure.

He reluctantly stopped rubbing her and reached inside his pocket for his phone. She got closer to him to check the time on his phone and took the opportunity to caress his growing bulge while giving him her number.

"We'll have to leave this pending," she said, referring to how their bodies were ready for a second go. "It's really late and I have a long drive home."

"Can't wait to see you again...Sophia. You're wonderful, fucking amazing," he said, unsure of how to show her how over the moon he was about her.

"Likewise, um, Nolan," she said, sharing a smile with him and slightly blushing at the fact she barely knew his name but had giving her anal virginity to him.

He got one final instance to appreciate her main asset then watched her walk away in the direction of her car. Part of him wanted to follow her swaying hips, but he didn't want to appear overzealous and ruin what had been a perfect night. He felt it was best to conserve the energy for their following meeting, one that was sure to match the intensity of their most lustful thoughts and desires.

What a night, she thought, feeling more of his cum dripping down her inner thighs as she relished the warm embrace of the night with the clear, starry night serving as a picture-perfect background.

They were in different stages of their life, that was evident, but they shared the same carefree attitude that led them to fulfilling such an erotic fantasy as strangers and that promised the opportunity to familiarize themselves with each other in ways they could only imagine.

Published 
Written by Issabela
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