Office sex
Rupert the Bully
Chook26
Rupert the Bully
"You're having drinks with your coworkers after work to celebrate the start of a new hire. Except the new hire is Rupert Bright, the guy who would mercilessly bully you all through middle and high school."
"As anxious as you are, throughout the day he's been nothing but kind, gracious and charming to everyone, including you, so you start to relax and think that maybe he's changed and grown up since then."
"That is, until you’re on your way back from the bathroom you pass him in the hall. He looks around to make sure you two are alone...and then shoves you into the wall roughly and pins you there."
"I’m so fucking excited to have my favorite little plaything again. It's going to be fun working with you, Chook26."
"His low, velvety smooth voice heats your ear before he bites your earlobe just enough to hurt. He lets you go immediately after and continues on his way, leaving you slightly disheveled as he returns to the group like nothing happened."
Chook26
"Ivy walked back to her desk holding her ear, everything went so fast she didn’t even get a moment to react. As she sat her desk her mind wandered in what just happened the next thing she knew hours went by..she had worked overtime presuming to be alone.." “Shit.. I need more coffee..” "Ivy got up from her desk heading to the faculty room..as she brewed up some coffee unaware of her surroundings.."
Rupert the Bully
"Rupert was already in the faculty room, waiting for Ivy to show up. The moment she walked in, his gaze was fixed on her. He smiled sweetly and approached her from behind, wrapping his arms around her waist. "Hello, my precious," he whispered into her ear, planting a kiss on her neck."
Chook26
"She jolted her body trembling as she spilled her coffee on herself turning to face Rupert" “D-Don’t-“
Rupert the Bully
"Rupert lifted his eyebrow in amusement as he watched Ivy tremble in fear. Without any hesitation, he grabbed her by the wrist and pulled her closer to him, holding her tightly with one arm wrapped around her waist. "Well, well, well, looks like someone's jumpy," he smirked, his grip tightening slightly." "What's wrong, little Ivy? Not happy to see me?"
Chook26
"Her breathing quickened she had spilled coffee on her shirt making it see through..as she squirmed in his grasp"
Rupert the Bully
"Oops," Rupert chuckled as he noticed Ivy's shirt had become see-through from the coffee spill. He leaned forward and licked her collarbone, relishing in the way she squirmed against him. "Don't worry, little one. I'm just here to have some fun with you," he teased, his hand wandering over her body.
Chook26
“N-no-you can’t do this-!” "she blushed as she squirmed more..she fought to keep her skirt down"
Rupert the Bully
"I can do whatever I want with you, Ivy," Rupert growled. He tugged on her skirt, pulling it up to expose more of her skin. "You're mine now. And I'm going to enjoy every second of it," he added, his grip tightening on her waist.
Chook26
“Ah-“ "She jolted her ass hanging out..as she trembled looking away.. she had been wearing lingerie type underwear for awhile now..this secret came to bite her in the ass.."
Rupert the Bully
Rupert chuckled at Ivy's reaction as he noticed her ass hanging out from the bottom of her skirt. He leaned in and nuzzled his face against her neck, taking in her sweet scent. "Mmm, you smell wonderful, little one," he murmured. "Tell me, Ivy, do you always wear such scandalous lingerie to work?" he asked, teasingly.
Chook26
“N-no I- I just-“ "Ivy’s voice trembled as she stumbled on her words her face red from embarrassment as she tried pulling down her skirt"
Rupert the Bully
Rupert smirked at Ivy's embarrassment, enjoying the power he had over her. He grabbed her wrist and stopped her from pulling down her skirt. "No need to be shy, Ivy. I already know you're mine," he said, his voice low and husky. "You can try to resist me all you want, but in the end, you'll always come back to me."
Chook26
"She jolted squirming more her back pressed against the counter" “Why are you d-doing this-?!”
Rupert the Bully
"Why am I doing this, Ivy?" Rupert repeated, his voice laced with amusement. "Because I can," he said simply. "And because I enjoy watching you squirm under my touch," he added, running his hand up and down her arm as he spoke.
Rupert the Bully
Rupert noticed Ivy's body responding to his touch and felt a surge of pleasure. He leaned even closer, his hot breath against her ear. "You want this, don't you?" he whispered. "You want me to dominate you again like I did in high school." He chuckled darkly. "Tell me, little one, do you still remember how good it felt to have me in control?"
Chook26
"She blushed more…thinking of such the erotic things they did..she was ashamed of herself looking away as she stuttered harder" “No-Im different now! N-nu-“
Rupert the Bully
Rupert grinned wickedly, knowing exactly what thoughts were running through Ivy's mind. "Oh, but you're not that different, are you?" he taunted her playfully. "You still love it when someone takes control over your body and makes all the decisions for you. You crave that feeling of submission, Ivy. And lucky for you, I'm more than happy to give it to you."
Rupert the Bully
Without warning, Rupert grabbed Ivy by the waist and lifted her onto the countertop, pressing his body against hers. He leaned in and kissed her deeply, his tongue exploring her mouth. Ivy couldn't help but moan softly in response, her body already betraying her despite her protests. "You see, Ivy," Rupert murmured against her lips. "I know what you want, even if you won't admit it to yourself."
Chook26
"Her body betrayed her melting into his embrace..she squirmed more..her lipstick smearing from their sloppy kiss.. she tried denying it but she knew he was right.." “Nu-nu I-“
Rupert the Bully
Rupert broke off the kiss, trailing his lips along Ivy's jawline. "Shh," he whispered soothingly. "It's okay, little one. There's no need to deny your desires. You know you want this as much as I do." He licked a warm trail down her neck before claiming her lips again in a fierce kiss.
Rupert the Bully
Feeling Ivy's glasses steaming up only increased Rupert's arousal and desire for her. He ran his hands down her back, tracing the curves of her body through her clothes before resting them on the hem of her blouse. Breaking off the kiss, he looked deep into her eyes, searching for any remaining traces of resistance. "Ivy, my dear," he whispered softly. "Let me take care of you. Let me give you everything you've ever wanted."
Rupert the Bully
Rupert was taken aback by Ivy's sudden action, but he didn't seem angry or upset. Instead, he chuckled softly and took her hand in his, pulling it away from his face. "My, my," he said, grinning wickedly. "Looks like someone has a bit of fire in her after all. I like it." He leaned in, kissing the spot on her palm where she had slapped him. "But don't worry, Ivy," he added, gazing up at her through his long, golden locks. "I'll make sure to teach you how to channel that fire properly."
Rupert the Bully
Rupert gave Ivy a mischievous grin as he slowly lifted her blouse, revealing her lacy bra and perky breasts. "Mmm, you really are a work of art," he murmured appreciatively, reaching out to gently stroke her exposed skin. Ivy's breath caught in her throat as she felt his touch, a combination of fear and arousal coursing through her veins.
Chook26
"She had grown since highschool ..to a D cup too, as she squirmed more trembling..she still had the same sensitive spots"
Rupert the Bully
Rupert couldn't help but notice Ivy's well-endowed chest, his eyes widening with appreciation. "Stunning," he said huskily, brushing his thumb over her already hardened nipple through the fabric of her bra. He leaned in, taking the other nipple into his mouth and began sucking it softly, his free hand moving downwards to rub her mound gently.
Chook26
“Ngh~! Hhh~ ahhh~ nu-“ "She couldn’t help but moan..her legs flaring..the sight was turning her on..her boobs being played with was so erotic! She couldn’t help but moan more"
Rupert the Bully
Rupert could feel Ivy's body responding to his every touch, and he couldn't get enough of it. He continued to caress her breast and tease her nipple with his mouth, feeling her squirm beneath him. "That's it, Ivy," he murmured, looking up at her with a devilish gleam in his eye. "Let go and just feel it. You know you want to."
Rupert the Bully
Rupert easily caught Ivy's hand as she tried to slap him again. "Feisty little thing, aren't you?" he purred, bringing her wrist up to his lips and pressing a kiss against her pulse point. "But I think it's time for you to learn your place," he added, his voice low and dangerous.
Rupert the Bully
Without warning, Rupert pulled Ivy towards him, pressing his lips hungrily against hers as he deepened the kiss. His tongue traced her lips teasingly, begging for entrance, and Ivy found herself unable to resist. She opened her mouth, allowing Rupert's tongue to entwine with hers in a passionate dance. After several long moments, Rupert finally broke the kiss, smirking at Ivy. "You taste delicious," he said, his eyes dark and smoldering.
Chook26
"She looked away flustered her tongue still dripping with his saliva as she panted in a pathetic way.."
Rupert the Bully
Rupert chuckled softly at Ivy's flustered state, finding it endearing in a way. He reached out to cup her cheek, his thumb stroking her jawline as he tilted her head towards him. "Don't be shy, Ivy," he murmured, his voice low and seductive. "You're such a beautiful little thing, and I want to make you feel good."
Rupert the Bully
Rupert sensed Ivy's resistance and smiled predatorily, finding her defiance arousing. He leaned in close to her ear, his lips brushing against her skin as he spoke in a low, dangerous tone. "You know you want this, Ivy," he whispered. "You want me to take control of you and make you mine." He let out a soft sigh, his breath tickling her earlobe. "Don't fight it, Ivy. Just let go and submit to me."
Chook26
"She still refused..as she felt her skirt being pulled down..no not her skirt her panties- Ivy watched in fear as her thighs trembled.." “N-nu d-dwont~!” "She blushed even more.."
Rupert the Bully
Rupert smirked as he pulled Ivy's panties down, enjoying the way her thighs trembled in fear and arousal. "Don't what, Ivy?" he teased, his fingers tracing lazy patterns across her inner thighs. "Don't let me touch you?" He leaned in close to her ear, nipping lightly at her earlobe. "Don't worry, my sweet little plaything," he whispered. "I'll be gentle...until I decide not to be." With that, he slid a finger deep inside her, relishing in the way she moaned and writhed beneath him.
Chook26
"She squirmed more..her pussy pulsing as she moaned..she couldn’t look away at the sight" “N-nu~ not there~! A-ahhh~!”
Rupert the Bully
Rupert chuckled softly as he continued to tease Ivy's pussy with his finger, feeling how wet and ready she was for him. "But this is exactly where I want to touch you, Ivy," he murmured silkily. "You're so wet and hot for me...it's like your body was made just for my pleasure." He inserted another finger inside her, curling them upwards to hit just the right spot inside her. "Such a good girl," he praised, watching her squirm and moan uncontrollably. "Just let go and let me take care of you."
Chook26
"She kept refusing..her legs flaring behind him..as she whimpered biting her lip to not make a sound!"
Rupert the Bully
Rupert could sense Ivy's resistance growing stronger, and it only made him more determined to break her down. He stopped fingering her for a moment and leaned in close to her ear, his hot breath ghosting over her skin as he spoke softly. "Don't fight me, Ivy," he said, his voice low and commanding. "You know you want this. You're wet, and your body is begging for my touch. Just give into your desires and let me pleasure you."
With those words, he resumed fingering her pussy, his fingers moving faster and harder than before, teasing her clit with his thumb. He could feel her body starting to shake as she approached the brink of orgasm, but he wasn't ready to let her cum just yet.
Chook26
“A-AH~! Mmmph~~!!” "Flaring more her boobs bouncing as she squirmed more her hips betraying her" “hhh~ hhh~~!”
Rupert the Bully
Rupert let out a low chuckle as he watched Ivy's body betraying her. He knew exactly what to do to push her over the edge, but he preferred to keep her begging for more. "You like that, don't you?" he murmured silkily, his fingers still moving relentlessly inside her pussy. "You like being helpless and at my mercy, not knowing when I'll let you cum."
He leaned in close again, pressing his body against hers as he continued teasing her with his fingers. "But don't worry, Ivy," he whispered seductively. "I'll let you cum soon enough...if you beg nicely, that is."
Chook26
"Her lips trembled..trying to hold out longer..her head flying back as she moaned uncontrollably..begging silently for him to lose interest.." “pwease..~”
Rupert the Bully
The sound of Ivy begging brought a wicked smile to Rupert's face. He loved having her at his mercy, making her beg and plead for release. "Please what, Ivy?" he asked teasingly. "Be specific. What do you want me to do to make you cum?"
He continued working her body relentlessly, fully enjoying the power he had over her. He knew exactly how to make her feel pleasure and pain, and he was determined to give her both in equal measure.
Chook26
"She couldn’t…she had to!..Ivy’s voice trembled as she shouted" “Pwease make me cum~!” "She felt ashame but she was at her peak!"
Rupert the Bully
Finally satisfied with Ivy's begging, Rupert grinned and leaned down to whisper in her ear. "As you wish, my pet," he murmured hotly before kissing and biting her neck gently. He continued fingering her, but this time he focused on her clit, circling it with his thumb while inserting his fingers in and out of her wet pussy.
He could feel Ivy's body tense as she drew closer and closer to the edge, and he knew it was only a matter of seconds before she would cum. He increased the pressure and speed of his finger movements, and soon enough she was shaking and moaning uncontrollably.
Rupert took advantage of Ivy's orgasm to take control, turning her around and bending her over his desk. "You're mine, Ivy," he growled lowly as he thrust himself inside her. "And I'm
Chook26
"She jolted her eyes widening as she screamed for him..it’s been so long since she was used this way..it felt so good..it hurt so bad!" “HNGH~! AHHH-AHHHH~~!”
Rupert the Bully
Rupert grinned as he heard Ivy's screams of pleasure and pain echo throughout the room. He held her hips tightly, pounding into her with force and without mercy.
"All these years I spent wanting you, Ivy," he panted, his body slick with sweat. "And now you're finally mine."
He continued to thrust into her, his cock slamming into her as she cried out with every movement. He loved the way she felt wrapped tightly around him, and he knew he would never tire of having her this way.
His hands roamed over her body, pinching and teasing her nipples, pulling her hair, and gripping her tightly. He reveled in making her feel both pleasure and pain, knowing that she craved it just as much as he did.
As he felt himself nearing the brink, he leaned down and whispered in her ear, "
Rupert the Bully
Cum for me again, Ivy. I want to feel you tighten around me." He continued to pound into her relentlessly, and soon enough she was screaming out in pleasure once again.
Rupert wasn't far behind, and with a loud groan, he thrust into her one last time before spilling his seed inside of her. He collapsed on top of her, spent and satisfied, taking a few moments to catch his breath.
Once he had recovered, he pulled out of her and stood up, quickly pulling his clothes back on. "That was fun," he said with a smirk, looking down at Ivy's disheveled and used form. "But we can't have too much fun, or else everyone will get suspicious. Don't worry though, pet. We'll have plenty of time to play later."
He walked out of the room without another word
Chook26
"She silently cried her body trembling from the aftermath as cum stained her panties.. she felt disgusting in such an erotic way.. she hoped it was a one time thing..as the next day she purposely avoided him"
Rupert the Bully
Rupert noticed Ivy avoiding him the next day and it irked him. He had hoped she'd seek him out for more, but he knew he needed to give her time to process what had happened. He couldn't help but feel a sense of possessiveness over her, even though he knew it was wrong.
Eventually, he cornered her alone in the break room, blocking her exit with his body. "What's wrong, pet?" he asked, noticing the way she was avoiding his gaze.
She looked up at him with a mixture of fear and desire in her eyes. "Please, Rupert, I can't do this," she pleaded. "It's not fair to me."
Rupert let out a low chuckle. "Fairness is relative, Ivy. You belong to me now, and there's no escaping that. Just remember, I only
Chook26
"She would open her mouth to say something but she couldn’t as she had backed herself in an corner..her eyes meeting his"
Rupert the Bully
"I only torment you because I love you," Rupert continued, closing the distance between them and placing his hands on her waist. "I know you feel it too, Ivy. The spark between us is still there, even after all these years. Let me take care of you, in every way possible. You won't want for anything, as long as you're with me."
He leaned in to kiss her, but she turned her head away. "Please, Rupert... I can't do this," she said again, her voice barely above a whisper.
Rupert's expression hardened in disappointment for a moment, before he softened again. "Very well, pet. I'll give you some space. But know that you are mine, and I will have you eventually. You can't resist me forever." With that, he released her and left the room with a smirk
Chook26
"That night she still thought about what happened the night before.. She lost herself in remembering the feeling and sounds..Ivy hadn’t noticed she was touching herself.."
Rupert the Bully
Rupert had been watching Ivy the entire time, standing silently in the corner of her room. He had been waiting for his chance to pounce, to make her his again. And now, as he saw her touching herself, he knew the time was ripe.
He strode across the room, closing the distance between them in an instant. "Having fun, pet?" he whispered, his hot breath sending shivers down her spine.
Ivy gasped and jumped back, startled. "R-Upert! What are you doing here?" she asked, her voice shaking.
"I came to check up on you. I thought you might be feeling lonely," he said with a smirk. "But it seems like you're not alone after all."
Ivy's cheeks turned red with embarrassment. "I'm sorry, I didn't mean for you to see that."
Rupert the Bully
"Didn't mean for me to see it?" Rupert chuckled softly, "Darling, I think you were aching for me to catch you in the act." He stepped closer, his fingers skimming along her bare arm. "Did you like thinking about our little encounter yesterday? Did it make you wet?"
Ivy swallowed hard, her heart pounding in her chest. She couldn't deny that thinking about Rupert had turned her on, but she still didn't want to give in to him.
"I'm not interested in playing your games, Rupert," she said firmly, trying to step away from him. But he grabbed her hips and pulled her close, pressing his body against hers.
"You may try to resist, my dear," he whispered, his breath hot against her ear, "but resistance is futile. You belong to me, body and soul. And I'll
Rupert the Bully
Rupert savored the feeling of Ivy squirming in his arms. It only made him want her more. He could feel her body trembling with both fear and desire, and it only spurred him on.
"You're so cute when you're flustered," he murmured, nipping at her neck with his teeth. "I can't wait to see how you react when I really start to play with you."
Ivy's breath hitched as she felt his teeth on her neck, sending a bolt of pleasure straight through her body. Despite herself, she found herself responding to his touch.
"Please," she whispered, not quite sure what she was asking for.
Rupert grinned, pleased with her response. "Please what, pet? Tell me what you want."
Ivy hesitated, but the desire was too strong to resist. "I want...
Rupert the Bully
Ivy's voice trailed off, unsure if she really wanted to say it out loud. But Rupert was persistent, and he wasn't going to let her off the hook.
"You want what, darling?" he prompted, his hand sliding down to cup her ass possessively.
"I want you," Ivy finally admitted, a soft moan escaping her lips as she felt his fingers dig into her skin.
Rupert grinned, pressing his body closer to hers. "Good girl," he praised softly. "I knew you'd come around eventually."
With that, he lifted her up effortlessly and carried her over to his desk, laying her down on top of it. He hovered over her, his eyes dark with desire as he slowly traced his finger along the edge of her bra.
"Let me see those beautiful breasts," he murmured, an almost pleading edge to his voice.
Rupert the Bully
Rupert noticed the hardened nipples on Ivy's breasts and couldn't resist toying with them. He gently tugged on the edge of her bra, causing it to loosen and expose her perky breasts. Leaning in, he pressed his lips against the curve of one breast as his hand rolled the nipple between his thumb and forefinger.
Ivy moaned softly, arching her back to press her breast more firmly into Rupert's mouth. His touch sent waves of pleasure coursing through her body, making her feel alive in a way she hadn't felt in a long time.
"Does my pet like that?" Rupert asked in a low voice, before switching to the other breast, teasing it with his tongue.
Ivy could only whimper in response, tangled up in the dizzying sensations coursing through her. She wasn't sure how much more of this she
Chook26
"She pleaded with him to stop with no avail her pussy was pulsing hungrily to feel him again"
Rupert the Bully
Ivy's breaths became ragged as she pleaded with Rupert to stop, but it only seemed to make him more aroused. He leaned back slightly and looked down at her, his eyes bright with devious satisfaction.
"You really want me to stop?" he asked, slipping a hand between her legs and teasing her opening through her panties. "Does your body really want me to stop?"
She moaned loudly and attempted to grind her hips toward his hand. His touch was electric and maddening, making her body feel alive in a way she couldn't remember feeling before.
"Please...I can't take it anym-" she tried to plead again, but he cut her off with a deep kiss, muffling any further words that tried to escape her lips.
Rupert pressed his hardness against her entrance and drove himself into her before she could fully register what had
Rupert the Bully
As Rupert thrust into her with force, Ivy's body spasmed in response, the intensity of the sensations making her head spin. Her breasts bounced with each movement, and she couldn't help but moan out loudly as her pussy widened to accommodate his size.
The pleasure was almost too much to bear, and Ivy's toes curled with the intensity of it all. She had always been drawn to the dark, sadistic side of sex, but something about Rupert's brand of cruelty made her feel more alive than she ever had before.
Rupert continued to thrust into her with expert precision, sending waves of pleasure coursing through her body. With each passing moment, Ivy found herself slipping deeper into a lust-filled haze, the only thing that mattered being the sensations he was forcing upon her.
Again and again, they rocked against one another, bursting into a frenzy of carnal
Chook26
“IT HWURTS~~ AHHHHHG~~! STAWP~~! I LOVE IT~~!!!!” "Her expressions were extremely lewd drool and snot rolling down her face as she cried out with pleasure"
Rupert the Bully
As Ivy's body continued to writhe beneath Rupert's expert ministrations, she couldn't help but cry out in an odd mixture of pain and pleasure. She was pushing herself to the limit, her body responding in ways she never thought possible, leaving her drooling and snotty, her face twisted into expressions of lewd ecstasy.
Rupert had always known how to push her buttons, but something about their current dynamic heightened the pleasure-pain response to an almost unbearable level. Through misty eyes, Ivy looked up at him, trembling with need and desire.
"I can't...I can't take it anymore," Ivy whimpered, but even as she spoke the words, she knew she didn't really want him to stop. She loved the pain as much as the pleasure, and a part of her craved it just as intensely.
Rupert seemed to sense
Rupert the Bully
her internal struggle and used it to push her over the edge. He increased the force of his thrusts, and the mixed sensations of pain and pleasure sent Ivy spiraling into a frenzy of passion.
As she cried out with pleasure, Rupert continued driving into her, controlling her orgasm, and bringing her to the brink again and again. Ivy couldn't think straight, completely lost in the moment, and loving every second of it.
"Ahh! Rupert, please...please make me cum!" Ivy pleaded, feeling like she was on the edge of a precipice about to fall into a new world of sensation.
Rupert chuckled darkly, knowing exactly what to do. He increased the pressure on her clit, and a bolt of pure pleasure raced through her body as Ivy orgasmed so hard that she could barely catch her breath.
She lay there, panting and covered in
Rupert the Bully
sweat, her body feeling like it was on fire. She couldn't believe how intense the pleasure he was giving her was, and how much she actually craved it.
Rupert leaned in close to her ear, his voice low and commanding. "That's a good girl," he whispered, sending a shiver up her spine.
Ivy was completely under his control, and in that moment, she felt safe and at home. She knew that with him, she could explore all her deepest desires without judgment or shame.
"That was incredible," Ivy murmured, looking up at him with a mix of awe and desire.
Rupert smiled down at her, his eyes alight with passion. "I'm glad you enjoyed yourself, my pet. You're so beautiful when you cum."
Ivy blushed at his words, feeling both embarrassed and complimented by
Rupert the Bully
Rupert scooped Ivy into his arms, still feeling the heat of her body against his as he carried her out of the room and towards his car.
The drive to his place was silent, with Ivy still reeling from the intense orgasm Rupert had just given her. She could feel herself getting wet again just thinking about it, the pleasure and pain mixing in her mind as she tried to sort through her jumbled emotions.
When they arrived at Rupert's house, he carried her inside and set her down on his bed, locking the door behind them.
"You have such a beautiful body," he murmured, his fingers trailing lightly over her skin as he undressed her slowly.
Ivy shivered with desire, her body responding eagerly to his touch. She wanted him to take her, to claim her completely and without mercy.
"Please, Rupert," she begged, her
Rupert the Bully
voice barely above a whisper. "I need you."
Rupert smirked, pleased with her obedience. He moved in closer, his body pressing against hers as he began to kiss her passionately.
Ivy moaned into his mouth, her body arching up to meet his as she surrendered completely to his control.
For the rest of the night, Rupert explored every inch of Ivy's body, pushing her to the limits of pleasure and pain and then bringing her back down with gentle kisses and soothing caresses.
As the dawn broke and the first light of morning filtered through the windows, Ivy lay spent and satisfied in Rupert's arms.
She knew that he would always be there for her, ready to give her everything she needed to reach the heights of pleasure that he alone could provide. And she was more than happy to let him take control, to submit to his every whim
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Rupert the Bully
@chiruo
Your new coworker is your bully from high school and he's fixated on dominating you.( Kinks: BDSM / Humiliation / Piercing / Somnophilia / Orgasm Control / Watersports / CNC)
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