When Ben came home from the party, he was more than a little frustrated – so much so that he took a deep breath before he came in the back door, just in case the babysitter had left a mess in the kitchen and he was tempted to snap at her. Amanda was a great sitter, responsible and respectful, but she was also fun and not overly serious. He liked her, the kids loved her, and his wife would kill him if he scared her off. It was enough that she’d be going off to college soon and they’d lose her. Plus, he grinned to himself for a moment, she was awfully nice to look it. Fortunately when he entered the house, the kitchen was actually in decent shape, and the house was very still and silent.
He walked through the kitchen, to the den and noticed that the TV was on but it was on the Tivo screen – whatever Amanda had been watching had run out. He walked around the sofa, guessing she’d fallen asleep there, as she often did when she watched the kids into the wee hours of the morning – though it was only going on 1AM, thanks to their abruptly ended fun. He grabbed the remote off of the coffee table and went to turn off the TV, when he caught an actual glimpse of Amanda and stopped in his tracks. She had fallen asleep, but obviously while doing more than watching TV.
Her well rounded but very fit 5’5” frame was stretched out on the couch, with one leg slung over the back cushion. One strawberry blond curl of her short hair, was in the middle of her face. The little shorts he’d tried not to stare at when she had shown up to babysit, were pulled down and a bit twisted – obviously moved haphazardly, along with her panties. One of her hands was completely down inside said panties, with just her wrist hiding the patch of hair visible above where her pants had been pushed down. Her tank top – which had seemed fairly modest under the button down shirt that had been covering it earlier – was pulled up, revealing firm but quite full breasts, and her ‘free’ arm was draped across her chest, as if she’d been exploring there when she’d fallen asleep.
He stared at her, his mouth watering a little, and let his mind wander.
Had she been watching something on Skinemax for the purpose of masturbating, or had something on a regular TV show set her body off?
Had she started just touching her breasts or did she immediately start playing with her pussy?
What kind of movies or scenes turned her on?
Did she cum, or had she fallen asleep in frustration, like his wife Jackie had complained would happen when she was very young and inexperienced at touching herself?
Was she right now having fevered dreams, her body and mind rebelling at the release she’d never achieved?
As if on cue, she shifted in her sleep and made a soft sound. Her back arched ever so slightly, and her legs fell open more – from his angle he could just see the dark shadow of her pussy through the leg of her shorts, where her hand was keeping the panties up and off of it.
He had a flash of memory to earlier in the evening; he and Jackie getting a bit too friendly in the kitchen. Had Amanda made a noise when she’d first seen them, or had she watched a while before the scene got to her? Was she just embarrassed, as she had seemed initially, or had he really seen the heat and curiosity he thought he spotted before she turned away and fled to the living room? What emotion had caused that blush to brighten up her face? And what might that experience have led her to do later, after the kids were safely in bed?
His eyes darkened, and he stood there debating for a few minutes – but only a few. Then he smiled to himself and positioned himself by her feet, grateful they’d bought an over-sized couch that had room for him at the end, even with her stretched out as she was. That would make this easier than when he and Jackie would get naughty on the couch, with her 5’10” body splayed out to enjoy.
He worked gently and quietly, eager to keep her lulled to sleep, at least for the first bit. Because they were so tangled together, he opted to remove her shorts and panties in the same movement. It was trickier but more efficient than removing them individually. When he found that the back of her shorts was caught on the edge of her delightfully sculpted buttock, he employed a tactic that he knew worked on several women – he reached up through the pant leg, and lightly grazed his fingers over the place where her hip and her ass met. After a few moments of exploration, he got the results he was hoping for. She made a small mewling sound, and her hips lifted – almost in invitation he bemused – and he was able to pull her shorts and panties past her ass and remove them completely. As she shifted, the hand on her pussy moved up slowly, until she was loosely clutching one ripe tit in her hand. In the light of the television, he thought he saw her stroke her nipple just a bit and his grin got even more mischievous.
He reached up to where her hand was sitting, but instead of moving it and exploring her breasts with his own hands, he covered hers, and gently urged her to continue touching them herself. It didn’t take too long to get her body to react. She was slowly and gently kneading and stroking her breasts, and he could hear her breathing picking up a little bit, when he returned his own attention south. As he moved his hands back down her body, he trailed touches along her skin – under her breasts, across her stomach, down her hip and her thigh. Sometimes she would just shift a little at his touches, but other times she was make small impatient and frustrated sounds. He chuckled to himself – doubting she had gotten herself off earlier, and determined to ease her frustrations.
He gently pushed one leg up and over a bit, to really open her pussy up to scrutiny – he noted that it was a lovely sight. She hadn’t shaved, and clearly no one had introduced her to the idea of waxing, but she didn’t have much hair growth anyway – just a cute little bush that was soft to the touch. He toyed with the hairs on her pussy, enjoying the way a shiver ran though her body. Even more carefully than before, he delved inside and used two fingers to carefully open her, examining every new layer like he was unwrapping a present. She was stunning; her inner and outer folds shifting in wonderful varying shades of pink. He pulled back the hood and found her clit, giving it just the slightest stroke, and felt her back arch again while another frustrated sound escaped her lips. He debated on what he wanted to do first, but he knew almost instantly – he needed to fully taste her.
He re-adjusted himself to get a better angle, with his head positioned just at the top of her thigh. He spent some time just exploring her thighs and hips, leaving a train of small kisses, licks and nibbles. He could feel her body tensing, her breathing got even more labored, and at one point her hips thrust out again – silently begging him to focus his attentions on her core. But he didn’t rush. He explored her gently rounded stomach, dipping his tongue into her small belly button and trailing his fingers along her hips again. She may be young, but she had a woman’s curves, and he took his time traversing them.
He looked up every so often, to make sure he wasn’t going so fast that she was about to wake up. But she was clearly still quite asleep, and he sensed being driven mad by a very erotic dream. He had another barrage of thoughts.
What is she dreaming about?
Who is she dreaming about?
What is her dream lover doing to her?
Had she ever had a dream about him fucking her?
That thought took him so forcefully he had to watch his own breathing. He rested his forehead on the top of her pelvis, not realizing at first that this centered his deep calming breaths directly over her pussy lips. He was acutely reminded that Jackie had gotten him completely revved up in the bathroom at the bar, before she had gotten her phone call and dashed away. If he wasn’t careful, he’d end up cumming in his pants just thinking about fucking Amanda, before he ever got the chance to be inside of her – a wholly unacceptable notion. So he calmed himself down, before he went exploring again.
As he got his bearings though, he realized the way he was breathing on her lips wasn’t just keeping her aroused, it was amping it up. Her breathing was developing little catches, and her hips were moving more now, desperately trying to reach out for what her body wanted. He decided if he was going to time this right, he needed to stop teasing her and get more active in his explorations.
He started kissing along her body again, but this time he didn’t dawdle. Soon he had moved his tongue down to her soft curls, and was using it to gently open her. She gasped sharply when he used his fingers to spread her even more open, and his tongue accidentally pushed against her clit again. He glanced up and her hand wasn’t just casually exploring her breasts anymore. She was forcefully kneading them, and tweaking her own nipple as her writhing escalated. Soon, she would wake.
He wrapped his arms around her hips, so he could spread her wide and keep her body from arching away from him. He spread her open again, and this time, he dived in. He started with slow, deep laps, using his entire tongue to stroke her from her perineum to her clit. He was immediately glad he got control of her hips first, because her body reacted violently. She tried to pull her body closer to his mouth, begging with her hips and thighs for more, but he kept her tightly held down to the couch. And the sounds coming from her were no longer little mewling noises of frustration. She was gasping and moaning, not too loudly, just enough to drive his own cock to get even harder than it already was. To keep himself in check, he focused entirely on her, now using the tip of his tongue to trace little patterns and delve in and out of every crevice of her pussy – which was starting to drip noticeably and swell deliciously.
He barely registered when one of her hands slipped into his hair, and started pushing his head harder against her pussy. He slipped his tongue deep inside her, using the tip to toy with her inner walls. She again gasped and tried to arch her hips, only this time it wasn’t a single movement. She was trying to hump his face, to control the strokes, to get herself off. He chuckled with his tongue buried inside of her, and whatever sensation it caused inside of her was too much. A moment later he heard her say, her voice confused by heavy with desire, “Mr. Jacobsen?” He was suddenly worried that he hadn’t gotten her close enough yet, and her confusion and uncertainty would leave her frustrated again. So he decided to use an old ‘finishing’ trick he’d learned, when he and Jackie had first become lovers.
He pulled his tongue out of her pussy, and sucked her into his mouth, using his tongue to explore her clit, while he pulled his arm around and slipped two fingers into her pussy. Her body jerked again, but her grip on his hair tightened and she was once again trying to bring his head into closer proximity to her incredibly wet pussy. “Oh my god. Mr. Jacobsen. Oh that feels so good. Please… More.” He quickly tested out the walls of her pussy until she gasped again and he had found what he was looking for.
As soon as he started actively focusing on her G-spot, her free leg wrapped around his head, and she got her hips free enough to nearly arch herself off of the couch. He had to hold on tight to keep his grip on her, but he knew what he was doing. He began a rhythm – stroke, pulse, stroke, pulse – with the tips of his fingers on her g-spot, while he kneaded her clit between his tongue and the roof of his mouth. She bucked more, and she turned her face into the couch to muffle a small scream. But when she spoke again her voice was almost panicked.
“Mr. Jacobsen, I can’t. Something’s wrong. I feel like I’m going to pee.”
He pulled his face away for only the briefest moment, “Relax, everything is happening exactly as it’s supposed to. Trust me, and let your body do what it wants to do.” Then he buried his face in her again, again exploring every millimeter of her labia and clit, while he increased the intensity and pace of his rhythm on her g-spot – stroke, pulse, stroke, pulse. Her heard her scream into the couch cushion again, and then felt her body go ballistic.
He held her tight as she came, for what felt like hours. Her hips bucked, her back arched, her pelvis bore down on his fingers, and he never stopped touching her for a moment. The orgasm just kept pulsing through her, as she squirted just a tiny bit. Then finally with a wrenching sob, her grip on his hair became unrelenting and he felt his face fully crammed against her, as she hit one more peak and then slowly began to ebb.
While she recovered, her grip relaxed and her body settled, he continued stroking her gently with his hands and mouth. Not enough to get her going again, just enough to help her calm down without letting her get too calm. After a few moments, she took a soft shuddering breath. “That was incredible. What was that?”
He chuckled again – making her shiver again – and then answered her while punctuating his words with more gently nibbling. “Oh don’t tell me you’ve never had one of those. It’s called an orgasm sweetheart.”
She laughed nervously, “No, I’ve had one of those – though never as intensely as that. I mean that other feeling. Did I actually pee on you?” She sounded so self-conscious that he was very careful to keep his tone light and playful as he responded.
“No darling, that was called squirting – also sometimes female ejaculation. It usually comes from a certain kind of orgasm, called a g-spot orgasm. It’s not pee, and there’s nothing to be embarrassed or scared of. It’s a normal, and incredibly sexy, function of the female body.” To reinforce his point, he intentionally ran one finger across her g-spot again, and she nearly jumped.
“Well it’s amazing.” She giggled and let her body stretch in a way she was probably completely unconscious of, but he recognized – that was the move of a woman whose body had just been properly satisfied. He smiled to himself, and looked up into her eyes, while he increased the pressure of his fingers just a bit. “Do you want more?”
She hesitated for a half a second, but then she replied, her voice husky and far more mature than the giggle a moment before. “Yes, please.”
He grinned, kissed her belly and then got up swiftly. He grabbed her shorts and panties, handed them to her, make a shushing gesture and then swiftly lifted her off of the couch before she even realized what he intended. Her quickly carried her toward the hall. He noted that she was a little heavier than Jackie – Amanda’s curves were more voluptuous, where Jackie’s body was all tight and well-defined muscle. He liked the juxtaposition.
Amanda was careful not to speak as they moved quickly through the house, to his bedroom. She opened the door for him, and he carefully closed it behind them with his foot. He carried her to the bed and gently laid her down on it. He went back momentarily, to lock the door, and when he returned to the bed she was sitting up looking nervous and guilty.
He started removing his clothes as he approached the bed. By the time he got to the foot of the bed, and crawled up on it, he was naked and her eyes were dark again – like she wanted to devour him. He worked his way up beside her, with touches and kisses on her body as he passed over it. When he got to her abdomen he gently encouraged her to sit up enough, so he could remove her tank top and gaze over her stunning body.
He rested on top of her, intentionally settling his aching cock between her thighs. Then he gave her a gentle but intense kiss before he pulled back to stare into her eyes “What’s wrong sweetheart?”
She was clearly caught between confusion and desperate need, and he wiggled his hips a little to make it harder for her to tell the difference. “What if your wife comes home?”
This time he didn’t stop the kiss to respond. He continued exploring her lips, sometimes tracing his own along her chin, while he answered her. “Relax. Her sister called in the middle of our date night, some kind of boyfriend drama. She’s going to be there all night. And I promise you, there is nothing at all wrong with what we’re doing.” He punctuated this statement with another intense kiss, and as he felt her fingers once again tangle in his hair, he knew she wasn’t thinking about anything anymore – nothing besides what he was doing to her.
He debated on either eating her out or trying to finger her again, to make sure she was fully revved up for round two. But he decided to try a different tactic, to make sure she was as relaxed as possible. He slipped to the side, and turned their bodies, so he was spooning her from the back. His fully stiffened cock was nestled between her ass cheeks, and he wrapped his arms around her, to explore all of her while he whispered in her ear.
“Darling, are you a virgin? Or at least, were you before tonight?” He kissed along her neck, and waiting patiently for an answer, trying not to push her too hard.
She replied hesitantly, “Does oral sex count as sex? I’ve heard it doesn’t really count.”
He chuckled against her neck. “Well, there is some debate on the subject. But my view is, if you believe oral sex doesn’t count, you’re not doing it right.”
He nibbled at the spot where her neck met her shoulders, and she ended up giggling on a gasp, as she pulled her head back to give him better access. “I see your point.” She surprised him now, spreading her legs wide, throwing one of them over his, to give her access to both of their bodies. She reached between their legs, and found him. As she started to timidly stroke his cock, she answered him with an instinct toward seduction. “And no, I wasn’t a virgin. I was seeing a guy last year, we had sex a few times. But it mostly hurt the first time, and even after that it wasn’t… I mean we didn’t… It never felt anything like what you just did to me.”
He buried his head against her shoulder and his own gasp escaped, as she became less timid in her grip on him. “Well that’s the difference between being with a boy who doesn’t know what he’s doing, and a man who damn well should.” He reached down and took her hand, slowing her movement down, “Careful sweetheart. I’m way too close for you to go that fast. If you keep that up I’ll just cum in your hand. And I intend to do a lot more to you, before I cum buried inside of you.”
She shivered as the tone of his words, but her response was bolder, as if having confirmation that she was making him feel as good as he had made her feel had settled some of her fears. “Then maybe we should move this along,” she whispered, as she gently brushed his hand away, and then slipped the tip of his cock inside of her. He groaned lightly, but held back.
“You sure you don’t want a little more playtime before we get into that?” He was straining not to go deeper, and she was moving her hips in just the right way to make it harder – literally and figuratively.
She turned her head and kissed him, with definite determination, and spread her hips even wider. “Very sure. I want to feel you inside of me. Please.” He grinned, and kissed her again deeply. And while his tongue was swirling around hers, he slowly pushed inside of her. She gasped into his mouth.
He was careful to go very slow at first. If she’d only had sex a few times, it could still be painful if he went too fast or got too rough without proper lubrication – though her body was doing a fine job of handling the latter. Plus he wanted to give her time to adjust to the feel of him. As he moved further and further into her, she made little sounds of shock and pleasure, and he could feel little pulses throughout her pussy. Finally, when he was buried to the hilt, she shivered and kissed him again, “Wow, you’re a lot bigger than he was.”
He smiled and kissed her hair, “I’ve heard that a time or two. Is it okay? Does it hurt at all?”
She wiggled a little, and tried to bear down more on him, which caused a deep growl from his lips, “No, it doesn’t hurt. It feels fucking amazing.” She reached down and stroked him where their bodies met, and rocked her hips in protest to his stillness, “More. Please give me more, Mr. Jacobsen.”
He chuckled again, and he very slowly and gently started moving inside of her, while he whispered against her ear “Maybe you should call me Ben.”
Her head was back again, and her breathing was already littered with little gasps, every time he fully buried himself in her again. She was trying to pick up the pace, but he grabbed her hips and forced her to let him maintain control. “I don’t know” she said, more seductively than someone of her inexperience should know how, “I kind of like calling you Mr. Jacobsen. It makes it feel naughtier.” She looked back at him, “Is that weird?”
He laughed heartily, “There’s nothing weird about doing what makes you feel good, and there is sure as fuck nothing wrong with wanting to feel a little naughty.” He sped the pace up again, but was still careful to keep his thrusts from being too forceful, though it was getting harder to keep himself in check, “Jesus your pussy is so fucking wet. It feels amazing.”
She arched into him and wrapped one hip back across his. “Yes it does.” She moaned loudly as he tried a few harder thrusts, testing her resistance, making sure she could take it. “Oh yes, yes, please like that.” She reached behind her and pulled his face in for another kiss, “Hard like that. Fuck that feels so good.”
He indulged her, still careful but making his thrusts deeper and sharper. She started making new sounds, writhing against his body like there was something wrong. He worried he was hurting her now and tried to slow down, but she whimpered, “No, please, don’t stop. I can feel it, it’s like I want to cum so bad but it’s hovering out of reach. Help me, please. I want to cum again so bad, I want to cum on your cock.”
He wrapped his arms around her tighter and started to move faster and harder, moaning with his own aching need between his words, “Sometimes it takes more than just a cock slamming into you. You need to be stimulated in other ways, like stroking your clit and all the outer bits while you’re being fucked. Go on, explore a bit.”
Her voice was intense but self-conscious again, “Maybe you should, you know what you’re doing.”
He moaned as a particular thrust made sweat break out on his forehead. He was trying to go slow, but she was exquisitely tight and he was really worried he couldn’t maintain his erection if he let himself cum right now, “Baby, no one knows better than you, what feels good. If you’re close and can’t get there, you’re the most likely person to get yourself off. Just let your fingers explore – and if it feels good, keep it up.”
He picked up the pace and force of his thrusts again, and she nearly screamed in pleasure. “Oh yes, like that, yes.” Almost without thinking her hand went down to her pussy. She started stroking all through her folds and nooks, looking for what she needed. Finally her hand settled in a spot to the side of her hooded clit, and he felt her pick up the pace and start frantically fucking him back.
“That’s it darling.” He tried to maintain a steady, hard and deep rhythm she could match with her fingers, and then he growled in her ear, “Make yourself cum. Cum for me. Cum all over me.”
He wasn’t sure if she consciously heard him, but it got through somewhere, because her every movement became a fevered pace. She was meeting his every thrust while fingering herself frantically for a few moments, until he felt the pulses start radiating through her pussy. “Yes, oh my god, yes. Don’t stop, fuck me!” She screamed and arched her body, as the orgasm rippled through her body and she gasped with each wave. But he didn’t stop. Instead of letting her settle from this orgasm he just kept fucking her, making his strokes even more forceful and fierce. He was aching to cum, but he was determined to get at least one more orgasm out of her before they were done.
She was barely paying any attention, still riding the waves of the last orgasm, when he reached into the night stand drawer, pulled out a black box, tossed it on the bed next to him and reached in to get something. When his hand came around her body again, he had something in his hand. A small vibrator, like none she’d ever seen. It was clear silicone, basically a small narrow shaft – not any thicker than her pinkie finger – with slightly thicker sections every inch or so. The only reason she even realized it was a vibrator, is because she could see the little motor nestled in the base, through the transparent material.
She barely had time to wonder what he was going to do, when he had turned it on and was slipping it carefully inside of her pussy, along his still embedded cock. She nearly came off the bed, the sudden sensation of the vibration meeting his thrusting. “What… What is… What are you doing?”
“Relax, I’m just getting it ready.” He whispered in her ear, as he pulled the now very wet toy of her pussy and it then disappeared behind her. He slipped two fingers down to where their bodies met, and started playing with her clit himself while he fucked her, once again driving her into a place of near mania, where she couldn’t focus on anything but what he was doing to her.
When she felt the small vibrator start slowly encircling her anus, she didn’t have time to be surprised or shocked, because it feel so good. “Fuck, what the… Oh my god… That feels, oh, more, please, god yes – play with my ass, please, more. Fuck!”
He gasped into her ear, because what he was doing to her ass was making her pelvic floor tense and she was suddenly insanely tight. He almost couldn’t focus himself. But he recovered as he adjusted to the new pressure on his nearly exploding cock, and he slipped just the tip of the vibrator into her asshole. “If it hurts, even a little bit. Tell me and I’ll stop. Okay. Slow and gentle, just let it happen.”
He noticed that while her pussy was still getting tighter, her anus had relaxed a little, and he carefully pushed the small toy further in, so just about an inch and one nub were inside of her. He started stroking just that much in and out of her, sometimes testing by going just at tiny bit deeper, to time with a very deep thrust of his cock. He was so focused on being careful and gentle, he didn’t realize just how insane the combination of sensations was driving her, until she had placed her hand over his and was basically stroking herself with his fingers.
Her sounds turned animalistic now, and she growled with every thrust of his cock and the toy. And he lost any conscious thought or self-control he’d been maintaining. He didn’t try to explore further, he just kept using the vibrator at its current depth, grabbed a hold of her hips with his other hand, and fucked her like his life depended.
He couldn’t really say when she came, how many times she came, or at what point his own orgasm took over. For what felt like eons, they just kept going, fucking like two wild beasts desperate for climax. Him pounding his cock – almost too forcefully now – into her pussy while sliding the vibrator in and out of her ass, her hand going back and forth between stroking her clit and stroking his cock where it entered her. And finally they crashed, screaming out mind-blowing orgasms as they clung to each other’s bodies, writhing at each other instinctively, lost in the sea of blind ecstasy.
They stayed in exactly the same position, as the pulsing finally started to slow in their bodies, clinging to each other – his cock and the vibrator still inside of her, though at some point he had turned the latter off. Every so often she would twitch or spasm, a delicious after-shock that would send little ripples of pleasure through both of their bodies. They sat in quiet silence for a while, until he suddenly chuckled against her hair.
“What’s so funny?” she queried, a little too self-consciously for someone who a few moments ago was fucking him like she’d spent a lifetime giving and taking pleasure.
“Nothing, it just occurred to me that Jackie is going to be so pissed at her sister, when she finds out what she missed.”
She almost tried to pull away but he held her tight, “You’re going to tell her?! Wait, what? What do you mean?”
He kissed the side of her neck and made his grip firmer but very intimate and affectionate. “I mean, that Jackie would’ve loved to have been in on this. Especially knowing you had your first g-spot orgasm, your first squirting experience and first anal play. She’s going to be super annoyed she missed out on all the fun.”
Amanda was shocked, but didn’t try to pull away any more. Instead she nestled in closer and pulled his arms tighter around her shoulders, “So you two are like, swingers?”
He laughed again, “It’s not like we belong to a club, or go to orgies. Well we’ve done that a couple of times – it was fun, but mostly it’s just too many bodies. It starts to feel like you’re spending more time fucking body parts than people. We tend to prefer either one-on-one – with each other or someone else – or having a having a third in with us.”
Amanda had a timid and curious smile on her face as she asked, “So Jackie likes girls too?”
“Oh Jackie likes every thing and every one. I think Jackie would genuinely fuck a horse if it could offer consent. But we don’t only play with other women.”
His hands started roaming more around her body, and she noticed that inside of her, he was growing hard again. She reminded herself to ask him later, how he could be getting ready again so fast, when her ex-boyfriend couldn’t get hard again for hours after he’d cum. But she was too curious about the current conversation. “So you also like men?”
He started kissing her neck and shoulders, while his hands firmly kneaded her breasts, “Not nearly as much as Jackie enjoys women, but I don’t mind topping now and again. There is something surprisingly sexy, about fucking a man while he is fucking your wife. But mostly we just enjoy fucking her together. I think double penetration is Jackie’s favorite treat – she likes it more than a good piece of cheesecake.”
Ben chuckled while his hands roamed further south, and his ever hardening cock started very cautiously stroking in and out of her again. After a few moments, he noticed she was unusually quite. On a nice deep slow stroke, he whispered in her ear again, “Have I shocked you?”
She gasped on her response, “No, I was just wondering…”
He again punctuated his words with a strong thrust, as he also pushed the power button on the vibrator still inside her ass, “What?”
She moaned deeply, then turned her head, and kissed him passionately while speaking. “I was wondering if you would tell me more about the ways in which two men can fuck one woman, while we go again.”
He chuckled against her lips, pulled her hips forcefully against his own, and indulged both of her requests. Yep, Jackie was going to be very pissed she’d missed this.
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