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Paul’s Double Penetration

Category: Anal Sex
08.10.2019
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This was way better than what she’d been expecting…

Tara had been looking for “something new” for a long time. She had married her childhood sweetheart straight out of college and thought that he was everything she wanted. She assumed marriage was a place to indulge all of her sexual fantasies and that her husband would want to join her in them. He instead became even more reserved. Sex, when she could convince him to, was short, boring, and very vanilla.

It wasn’t that Tara was that kinky of a girl, but having sex in the same two or three positions the rest of her life was not what she wanted. After six years of marriage, some counseling, and an obstinate refusal of her husband to try anything new, Tara gave up and asked her husband for a divorce.

Tara had been pretty vocal about the reasons for her divorce, and had expected her friends to help her find someone new, a “playmate” to live out her fantasies with. Her friends tried to set her up with pretty much anything that moved – the unattached friends that she’d known for years and never been attracted to, creepy guys, ugly guys, smelly guys… it was as if her friends weren’t listening to the fact that she was being more selective this time around and instead they just wanted her settled back down. Tara knew she was going to have to find her new playmate on her own.

She started looking online, at first with simple, flirtatious sites like craigslist and Adult Friend Finder, but eventually some more kinky options. Erotica sites, sex sites, even a couple of BDSM ones. Tara had always felt like she was a bit on the short and chubby side, but more than made up for it with her curves. She quickly learned that the number of men looking to fool around far exceeded the number of women, and that there were plenty of men who “loved” her and her DD boobs, so she could be as picky as she wanted. And oh did she need to be! There were plenty of copies of her boring husband trapped in sexless marriages, mixed in with some strange men. She didn’t want her boobs trapped in a car window. She didn’t want to lose her anal cherry to a large man who’d make her beg and cry for lube before pushing himself into her. She just wanted some fun. And then, she received a message from Paul.

Each e-mail exchange was more erotic than the last. Their short exchanges quickly went from innocent and friendly to anything but. Each time she described a fantasy of hers, he somehow made it hotter. She mentioned wanting to be in a threesome. Paul shared that he was bisexual and happy to explore other people with her. She mentioned how badly she wanted a man to eat her out until she came. He told her how much he loved giving oral, especially when it included his own cum dripping from her. She mentioned that she liked the idea of having her partner watch while she masturbated for him. He replied that not only would he like to masturbate along side her, but would love it even more if they left a window open so that others could hear. She really liked that he just wanted to play, and wasn’t interested in marriage or anything deep.

When they got to the point of exchanging pictures, Tara was happy to see how attractive Paul was. He appeared to be pretty average height and weight, with a slightly cocky stance and smile that made her smile. He obviously worked out, but wasn’t overly muscular and had the sweetest layer of flesh covering any possible bony spots.

Their relationship quickly progressed to phone. One night, while talking about fantasies, Tara mentioned how her ex-husband was very ass-shy. Wouldn’t let her near his crack, let alone touch his asshole. Paul was silent, and for a moment Tara was worried that she might have said something wrong.

“Are you kidding me?!?” Paul exclaimed, “I would love for you to play with my ass. Rub it, finger it, even use a toy and fuck me! I love both teasing and penetration.”

Tara felt herself growing aroused, “Would you ever let a girl fuck you with a strap-on?”

“Actually, I have been fucked twice with a strap-on and once used dildo on myself until I came. I have never told anyone this, but I even rode it to see what it would feel like. I loved it! So if you’re ever going to ask to fuck my ass the answer is yes.” Paul replied. Tara could tell that this conversation was turning him on, too.

Tara had always wanted to fuck a guy with a strap-on. She loved the idea of being in control, of being able to feel the sensation of thrusting into another person. At that moment, she knew she had to meet Paul, if for nothing else than to live out this fantasy.

“Can you go on your computer? Let’s go online and pick out some toys together,” Tara suggested, and Paul was happy to shop with her. They looked over a few sites, both getting more and more aroused as they looked at different options, and finally picked out a simple black padded harness that could accommodate a range of dildos and vibrators. In addition to the rather slim, five inch dildo the harness came with, Paul also suggested a slightly thicker than average, six and a half inch realistic looking one complete with balls.

“You really want to go that big?” Tara asked.

“Yep, I want it to feel as real as possible. You’re going to look so hot wearing that and fucking me!”

They discussed their schedules for a bit and decided to meet for lunch the following Saturday at a place close to her apartment and, assuming that lunch went well, drive over to her place afterwards to try out their new toys. Tara was a little worried at being intimate with someone who was more or less a stranger, but as the date grew closer she found herself more and more aroused.

That Thursday, Tara came home from work to find a plain, brown-paper wrapped box sitting on her front porch. She immediately started throbbing just upon seeing the cardboard box, knowing full well what was inside. She let herself into her apartment as fast as possible, closed the door, and tossed her things on the kitchen table. She cut open the tape and there were “their” toys, plastic wrapped and ready to go. Tara knew she should probably leave the items in their wrapping, so that she and Paul could explore them for the first time together, but she couldn’t help herself.

She stripped off her work clothes, kicking off her heels and then throwing her black pencil skirt, pink pin-striped blouse, pink bra, and matching pink panties to the floor. She pulled the harness out of the box. Always a practical girl, Tara read the rather useless directions on the box and looked at the picture before stepping into the harness. It was actually simpler than it looked, once she got it on – a buckle to adjust the waist, one for each leg, and a set of snaps to hold the dildo in place. After tightening the buckles to fit over her waist and muscular thighs, she pulled out the dildo that the harness came with, and snapped it in.

Tara walked down the hallway to her bedroom, adjusting to the feeling. She felt a slight heaviness to her crotch, as if she had a penis of her own. The padded front to the harness pushed against her mound, creating a rather pleasant warmth as she moved. She checked herself out in the full-length mirror in the bedroom, turning from side to side, looking at the harness from every angle. Tara liked what she saw. Her short brown hair, still perfectly set in her side-parted, smooth business look. Her blue eyes twinkling, a smile on her face as she traced her hands over her smooth, pale skin to reach down and tug on the dildo. All she felt was a tugging on the back of the waistband, but she liked how it looked in the mirror to jerk herself off. She could feel the throbbing in her pussy even more strongly now, and was pretty sure that she was soaked just from looking at herself. For a moment, Tara wished there was a way she could fuck herself with the strap-on. Suddenly, she remembered the second dildo. She went back to the living room, retrieved it from the box, and returned to the mirror.

Tara parted her legs slightly, watching as the straps of the harness just barely cut in to her inner thighs. She could see beneath her closely-trimmed bush that her labia were already opened and glistening. She needed to masturbate, right there in front of the mirror, with the harness still on. She looked at the dildo. It felt a bit awkward in her hand, with the balls getting in the way of giving her a good drip. But then she noticed the suction cup on the bottom. She pushed it into the wooden floor and wiggled. It stuck. Tara fell to her knees and eased the dildo inside of her, still wearing the harness. She watched in the mirror as the dildo penetrated her, smoothly making its way inside her wet folds. She rode up and down, watching herself. Without thinking about it, she began to stroke the cock in her harness in time to her thrusts upon the cock on the floor. With her other hand, she grabbed her left breast, pulling and twisting the nipple before doing the same to the right one. Tara loved seeing herself in the mirror, her body beginning to flush, a cock in her pussy and one in her hand. She moaned, giving in to the feelings that were beginning to stir from deep within her cunt. The newness of the situation, coupled with the images she could see in the mirror, brought her orgasm on more quickly than she expected. She pounded down on the cock on the floor, riding through her orgasm, screaming Paul’s name before gradually slowing down and letting the dildo pop out of her. She sat down on the floor, panting. Tara couldn’t wait for Saturday.

Finally the day arrived. Tara was feeling slightly nervous as she walked into the restaurant and was seated, but mostly horny. She smoothed her skirt, reveling in the fact that she wasn’t wearing any panties underneath. A couple minutes later, she saw Paul walk in. He seemed even cuter in person. He was taller than her, with short spiky hair. She had a passing thought that he was just the right height to reach up and kiss. Paul took off his sunglasses, scanned the restaurant, and quickly found her. She stood up in order to embrace him.

“Nice to finally meet you,” Tara quietly said in Paul’s ear.

“Nice to meet you!” Paul replied, grinning at her while obviously checking her out. She twirled for him, letting her skirt flair out enough to quickly bare the bottom of her mound, but not so much that she would be on display for the whole restaurant. Paul’s grin grew wider.

Lunch progressed quickly and well. Both Tara and Paul kept unconsciously scooting closer to each other in the booth as they talked over their phone calls and e-mails. Tara noticed a tattoo on Paul’s right tricep, and reached her hand out to move his sleeve up. Paul leaned towards her, so she could see it better, and used the opportunity to place his hand on her bare knee. She smiled up at him, and he began slowly moving his hand upwards. Tara wasn’t about to protest, and spread her thighs slightly to encourage him.

Paul didn’t need any encouragement. He slid this hand up her thigh, under her skirt, and across the top of her mound. He scooted slightly closer to her, and slid one finger between her labia, gently easing between her folds. “Yeah, you’re really wet,” he whispered, as much to himself as to her. He circled around her clit a few times, causing Tara to briefly gasp and close her eyes. She was debating letting him finger her to orgasm right there in the restaurant, when he withdrew. She opened her eyes to find his face within a few inches of hers, his finger in his mouth, tasting her. It was pretty obvious that he liked what he tasted. He withdrew his finger and Tara leaned over to kiss him. She could taste herself on his tongue, and was surprised to find that she liked it.

Paul reached over, grabbed her hand, and placed it on the crotch of his jeans. He quietly said in her ear, “Can you feel how much I want you?” She could feel that he was rock hard and throbbing. They needed to get back to her place before this got out of hand. Paul signaled for the check, they quickly split the bill, and then agreed to meet at Tara’s house.

They reached her building at the same time, Paul pulling his SUV to the curb as Tara parked her sedan in her assigned spot. She unlocked the front door while Paul strode up the walkway to her place. He entered behind her, closed the door, and pushed her against it, kissing her deeply. He reached his hands under the hem of her shirt, about to lift it off, but Tara stopped him.

“Nope, if I’m fucking you, then I get to be the dominant one. Now strip!”

Paul was more than happy to comply. He reached down to the hem of his black t-shirt and pulled it up and over his head, revealing his nicely built, mostly smooth chest. He kicked off his shoes and socks and tossed them into a corner. He quickly unbuckled his belt and pulled it open before looking at Tara. “Ready?” he said, taunting her a bit.

“I know how bad you want to show it to me,” Tara teasingly replied. Paul quickly unbuttoned the button on his jeans and unzipped the fly, spreading the waistband wide. He turned away from her before pushing his jeans and blue briefs down in one smooth motion, wiggling his bare ass at her. Tara was tempted to push him on to his hands and knees right then, but decided to wait. Paul slipped his clothes over his feet and stood to face her. He looked down. She looked down.

Paul’s penis was close to erect, at a slight slant away from his body. He (as she already knew from their e-mails) had very closely trimmed pubic hair, and the hair on his shaft and balls was almost non-existent. He had joked about not being nine inches long like “every other guy online” but she was happy to see a healthy six inches of pink springing back at her, and a slightly larger than average thickness to boot. “Nice!” she thought to herself.

Paul knew Tara was admiring his package, and wanted to get to full hardness for her. He began stroking himself, using a strong, steady pace, obviously enjoying himself as he did so. As Tara stepped towards him, Paul took her hand, firmly placing it on his dick. She slowly moved her hand up and down, amazed at how smooth he felt. His cock had all the usual bumps and veins, and a perfectly formed heart-shaped head, but the skin itself was the smoothest she’d ever felt. She started thinking about how good that would feel inside her and quickly got distracted, entranced by Paul’s smooth, hard shaft.

Paul’s voice broke her out of her reverie. “Will you please strip for me?” Paul asked, “I want to watch you play with yourself before you put on the harness.”

At this point, Tara badly wanted to get naked anyway. She stripped off her top, placing most of her breasts on display in the black plunging bra she was wearing underneath. She reached behind herself to unclasp her bra, and slowly pulled each strap over her shoulder, teasing Paul, before lifting the bra up and off, letting her breasts bounce before his eyes.

Paul’s eyes widened at the amazing sight before him. Her breasts were large and round, with big hard nipples atop each one. Tara lifted an eyebrow, “Like what you see?” She played with her nipples, rolling and squeezing them, before moving her hands seductively down her sides.

Tara quickly unzipped her flower-print skirt and let it fall to the floor. She began gently rubbing her mound, then used the fingers of her right hand to spread her labia, so Paul could see how wet she was and get a good view of her swollen clit. She rubbed her left hand over and around her clit, grinding it against her pubic bone. Paul moaned at the sight of her playing with herself for him. She moved her hand lower, penetrating herself, first with one finger, than two. She moved her fingers in and out, at first slowly, then gradually faster, trying to find that sweet spot where she could cum.

“Paul.” she finally asked, “will you make me cum? It takes me a long time with my own fingers rather than a toy.”

“Fuck yes!” he replied and immediately kneeled on the floor, gently pushing her thighs apart and using her skirt as padding for his knees.

Before Tara knew it, Paul’s head was deep between her thighs, his nose pushing on her clit, his tongue deep in her pussy. She had a feeling she was wet before, but now she could see her juices coating Paul’s face as he licked her for all his worth. His hands, which had been on the inside of her thighs, moved upwards, squeezing her ass cheeks. Paul moved the fingers of his left hand gently against her asshole, stimulating the nerve endings there, and with his right hand quickly shoved two fingers deep in her pussy.

“Oh, fuck!” Tara exclaimed, surprised by Paul’s fingers at both orifices. Within moments, she was cumming. Tara leaned forward slightly, putting a hand against the wall so that she wouldn’t fall over. She closed her eyes, giving in to the sensations slamming into her. She felt so good and they hadn’t even really gotten started. As soon as her orgasm began to subside, she felt Paul withdraw his face and hands. She opened her eyes to him using her juices to lubricate his shaft. “Ready for more?” he challenged her.

“I think the better question is are YOU ready for more?” Tara replied, and sauntered off to the bedroom. Paul followed behind, watching Tara’s ass sway as she moved down the hallway. They quickly reached the bedroom, where Tara had laid the harness out on the bed, complete with the larger dildo.

“Where’s the other dildo?” Paul asked, scanning the room, only finding a large bottle of lube on the nightstand.

“It’s sitting on the bathroom counter. Why, change your mind?” Tara countered, teasing him a bit. She didn’t care how big the dildo was; she just wanted to fuck him.

“No, no.” Paul looked like he was about to say something else, but kissed her instead. He helped her into the harness and then stood back, looking at her. “Fuck, that looks beautiful,” he said, and got down on his knees so he could suck “her” cock.

“Oh yeah, make it nice and wet, baby,” Tara said, her voice deep with lust. Paul began fingering her as he ran his tongue up and down the dildo, lubricating it a bit with his saliva.

Tara reached down and traced her fingers along Paul’s jaw line, then gently tilted up his head. “On the bed, on your back,” she purred at him.

Paul practically leapt on to the bed. Tara climbed up, grabbing the lube on her way. She placed a pillow under Paul’s hips, raising his ass towards her. His penis was rock hard, straight up in the air. He moved to stroke it, but she stopped him, “Nope, not yet, I want you to be concentrating on this first,” and, with that, she poured lube over two of her fingers.

Paul watched attentively as Tara reached down and began rubbing one slick finger around his asshole. He writhed under her, wanting penetration. She quickly complied, pushing in one lubed finger to the second knuckle. It went in a lot more smoothly than she expected. Tara looked at Paul questioningly.

“I wanted to be warmed up for you, so after I cleaned things up back there this morning I fingered myself for a bit.”

“Just couldn’t wait for me, huh?” Tara replied, and slid her finger the rest of the way in. She turned her hand a bit, trying to find Paul’s prostate. A moan from Paul and a thin stream of precum told her when she hit the right spot.

“Yeah, you needed me in your ass, didn’t you?” Tara said rhetorically. She added more lube and a second finger, wiggling and twisting her fingers, making sure Paul was stretched enough to receive the dildo strapped into her harness.

“Fuck, yes! Fuck me!” Paul exclaimed, groaning as she fingered him. He lifted his legs into the air and held the backs of his thighs with his hands, exposing his ass as completely as he could for her.

That was all the encouragement Tara needed. She lubed up the dildo, lined the head up against Paul’s waiting asshole, and moved her hips slowly forward. It was an odd sensation. She could feel the change in pressure as the head of the dildo “popped” through Paul’s sphincter muscle. She slowly thrust the dildo in all the way until the plastic balls pressed against his ass. She loved the increasing pressure against her mound as the harness pressed against her. Tara slowly moved her hips forward and back, getting used to the sensation of fucking a man for the first time.

Tara grabbed on to the top of Paul’s thighs, pulling him against her as she moved back and forth. Paul let go of his legs and reached for Tara’s hips, helping pull her even deeper in. She kept moving with relatively slow, even strokes. She alternated between watching Paul’s ass get penetrated, and look of pure bliss on his face. He looked like he was enjoying this as much as her, if not more.

Tara moved her hands slowly down from Paul’s thighs. He watched intently, hoping she might touch his cock, but instead she moved to just either side of it. Her hands roamed up his chest until she reached his nipples. Just as she thrust in deeply, she grabbed both of them and pulled slightly. Paul bucked against her, loving the additional stimulation. She arched her chest forward, and Paul took the hint and reached for her breasts. He followed her lead, pulling on her nipples as she pulled on his, rolling them between his index fingers and thumbs as she did the same, pinching them as she pinched his. Even though Tara hadn’t touched his cock once, Paul was getting very close to orgasm from all the stimulation he was receiving.

“Tara, can I finish on top?” Paul pleaded.

“On top?” She looked at him, slightly quizzically.

“Just lay back.” Tara decided to see what Paul had in mind, and reluctantly withdrew from his ass, leaving his asshole red and slightly gaping. They switched positions. Tara spread her legs, expecting Paul to move between them, but instead he put his knees on either side of her hips and ever so slowly eased himself down on top of her, impaling himself on the strap-on.

Tara smiled. “Ahhh, on top. I like it. I want to watch you ride me.” Tara placed her hands on Paul’s hips, steadying him as he moved up and down on top of her, stroking his dick to the same rhythm. He gradually moved faster, pushing himself on to the dildo, stimulating his anus and prostate with each stroke. His hand moved along his smooth cock faster, too. Tara could tell from the tightening of his fist that Paul was about to cum.

“Cum for me, baby! Cum all over my tits! Come on, cum while I fuck you.” Tara took control now, using her hands on his hips to pull him on to her, while simultaneously bucking up from underneath him, trying to push the dildo in as deep as she could. She went hard and fast, working to bring him over the edge.

Within a few strokes, Paul came. The first shot landed on the side of her neck. The next landed between Tara’s breasts, slickly moving down her cleavage. Paul continued to spurt all over her belly and breasts before finally finishing with one last dribble that ran over his hand. Paul leaned forward, letting the dildo pop out of his ass, before lying alongside Tara and helping her remove the harness.

Tara turned to face him. They kissed and cuddled for a bit, then Paul licked along Tara’s earlobe, removing a trace of cum, and gently whispered, “I’ll be right back.” He got up and headed towards the bathroom, harness in hand.

Tara looked down at herself. She was covered in cum pretty much from her chin down. Paul had warned her that he tended to cum a lot, but this was ridiculous. “I really should go clean myself up,” Tara thought to herself, but wanted to take a moment to recover. She was already feeling slightly sore, given how she’d used her leg muscles in a new and very satisfying way. She was also still really horny after fucking Paul. She rolled on to her back, intending to get up, when Paul walked out of the bathroom.

Paul had strapped on the harness, switching the larger dildo out for the smaller one. He’d somehow moved and folded the padding so that the slim dildo rested about an inch above his semi-erect penis.

“What are you…” Tara started, and then she realized what Paul had in mind and her eyes widened.

“You didn’t think I’d cum and then leave you there, with your pussy still needing a good fucking, did you?” Paul said, stroking his dick as he walked towards her.

Actually, that was exactly what Tara had been thinking, though she had loved thrusting the strap-on into Paul. “Well, I hadn’t really thought…”

“Roll over,” Paul said as he made his way on to the bed.

Tara rolled on to her belly. Paul could see the juices from Tara’s pussy running down the inside of her thighs. “Well, I definitely don’t need any lube there,” he chuckled to himself. “On the other hand…” he joked, as he traced his fingers up her crack, and lazily traced around her asshole.

Tara pushed her ass back towards him. After getting so turned on fucking Paul, she needed penetration, not just teasing.

“Give me a second, baby, don’t worry,” Paul said. “Now spread those cheeks for me.”

Tara laid her chest down on the bed and reached behind so that she could pull her cheeks apart. She felt Paul squeeze a ton of lube down her crack, coating her completely. He began rubbing it into her anus, not really penetrating so much as pushing. It felt so good to Tara.

“Pleeeeeeease” she whined, and Paul complied, gently pushing in one finger.

“Oh, fuck!” Tara exclaimed. Paul hadn’t even touched her pussy since he had climbed on the bed, yet she was already close to cumming. She pushed back against him, wanting to get the fingering over so that he would fuck her. She quickly regretted her decision.

“Ow, that burns a little,” Tara said, unused to the feeling. Paul slid his finger back a little then waited for her sphincter to stretch. He slowly moved his finger in and out, lubing and stretching her, until the burning subsided and the feelings of pleasure returned. Tara looked back at him.

“More?” she said, signaling that she was ready. Paul added a second finger, a bit more slowly this time. As soon as he passed both digits past her sphincter, she hissed, trying to ignore the burn and focus on how good it felt to have Paul’s fingers in her. The moment passed, and Tara was ready for more.

“Okay, I think I’m ready.” Tara said, lifting herself on to her hands and knees, her round ass waving in the air.

“Good, because I am, too.” Tara looked back and saw that Paul was completely erect again, and that both his penis and the plastic one were lubed and pointed at her. She watched as lined up both cocks to try and penetrate her holes simultaneously. Surprisingly, he got it right on the first try and very, very carefully so that he wouldn’t slip out, he pushed both cocks into Tara.

“Oh, FUCK! Oh damn Paul that feels good!” Tara exclaiming, surprised and delighted by how amazingly good it felt to be double-penetrated. She’d tried using two toys at once before, but had always failed. This was so much different. She felt as if her whole body was being filled. Paul continued slowly sliding into her, inch by inch. The slight burning in her ass was being completely overwhelmed by the pleasure of her aching pussy. After fucking Paul, she needed to be fucked. Badly.

Paul buried both cocks to the hilt, and then stopped. He rubbed and squeezed Tara’s ass, letting her adjust to the sensation of being totally filled from behind. With the dildo in her ass, her pussy felt exceptionally tight, and even though Paul had just come, he wasn’t likely to last very long like this. His smooth cock felt wonderful inside of her. He took a moment to get control of himself and then started slowly thrusting back and forth, watching as his cock and the dildo moved in sync in and out of Tara.

Tara quickly adjusted to the feeling and began pushing back against him, wanting him to go harder. Paul stopped playing with Tara’s ass and grabbed on to her hips, thrusting even more deeply into her. The extra centimeter or two was all Tara needed for her orgasm to start.

“Yessss!” she exclaimed, moaning and screaming as she came. Her pussy clenched around Paul’s cock, making her tight entrance even tighter against his swollen cock. Her asshole began to pulse and squeeze against the dildo, making it harder for Paul to continue his steady pace. He tightened his hold on her hips and began furiously thrusting into her, pounding both holes as she continued to cum.

Tara felt like her orgasm had no end. It had spread through her body; first, her ass, then along her belly and thighs, tightening every muscle. She felt like she was orgasming from head to toe, every inch of her in ecstasy as Paul pounded into her. This is what she had so desperately needed and wanted. The hard, strong, mutual lust. To fuck someone like Paul into orgasmic bliss and then receive the same in return. She screamed in delight.

“Tara, I’m sorry, I can’t…” Paul started, unable to hold back any longer. He buried himself into her spasming pussy and came. They finished together, and began slowing their pace, with Paul gently holding Tara’s sides until she laid down on the bed and his cock wetly slipped out of her. He lay on top of her for a moment, the dildo still buried in her ass, before rolling to his side and slipping off the harness.

Tara turned her head to face him. She smiled and simply said, “Thank you.”

Paul kissed her forehead. “Thank you,” he replied, “I think we both needed that.”

Tara laughed, “You think? So, are you going to join me while I take care of some more of my fantasies?”

Paul started laughing. “You bet I am! That was amazing. I can’t wait to see what else you have in mind for us.” With that, both closed their eyes and took a short nap, resting in post-orgasmic bliss, thinking of adventures to come.

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