The Face - Painter
Chapter 13

Copyright© 2012 by rmdexter

Erotica Sex Story: Chapter 13 - A well-hung young man with a talent for shooting lots of cum tries his hand at being a male escort; while on the home-front, interesting encounters with his mother and two sisters develop.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Ma/ft   Consensual   Heterosexual   Incest   Mother   Son   Brother   Sister   Oral Sex   Anal Sex   Masturbation   Size   Big Breasts  

"So, how's Dick the Dick this morning?" I asked, arriving about five minutes early for my 10:00am meeting with the magazine's chief editor, Richard "Call me Dick" Morrissey.

"I'm pretty sure somebody pissed on his Cornflakes again," replied Cara, his administrative assistant. I wondered when 'secretaries' became 'administrative assistants'. More of that 'politically correct' bullshit, I guess. Cara was a sweet woman in her late 40's. She was 'mom-sized' and not really on my MILF radar, but I liked her just the same. I know, it's surprising, a shallow asshole like me can actually be friends with a woman, even if I'm not eyeing them up as a future sexual conquest. Cara had been in this position for a long time, and basically ran the office. She also had a bit of a soft spot for me, running interference for me with Morrissey a number of times.

"Oh great. I barely got my article in on time last Friday. I already know he's going to try and tear me a new one. I don't need him in a bad mood at the same time. Did something happen?"

"Who knows with him? Maybe he missed last night's episode of '60 Minutes'," Cara replied with a shrug of her shoulders. "That article you wrote about the movies being made in town, I read it this morning. There's some good stuff in there."

"Thanks. Hopefully he feels that way too," I replied, nodding toward Morrissey's closed door. Just then, Cara's phone buzzed. She hit the speaker button.

"Yes?"

"Is that Young I hear out there?" I heard Morrissey's grating voice come over the phone. It sounded like fingernails on a chalkboard.

"Yes," Cara replied, sticking her tongue out at the phone and winking at me.

"Send him in. I haven't got all day."

Cara hit the end button as she looked at me and shook her head. I gave her a big smile as I turned and opened the door to the editor's office.

"Hey Boss," I said as I entered the room. I smiled to myself as I looked over at the big bulletin board he had on one wall. There were papers with the ongoing assignments tacked all over it, plus other miscellaneous pieces of information. I'd snuck into his office one day when he was out for lunch and stuck up a picture I'd printed off the internet. It was a print of the cover of Morrissey's album "Ringleader of the Tormentors", with a black and white photo of Morrissey playing a violin. I figured the title was perfect for Dick. Surprisingly, he must have liked it—it was months later, and the picture was still there.

"Close the door and sit your ass down, Young," Dick the Dick replied. I don't think I'd ever heard the guy refer to me by my first name, even the first time I was interviewed. His office was a mess—shit everywhere. I almost laughed out loud every time I came in here. The guy had a brush cut and a big bristly moustache, coupled with a rumpled shirt and loosened tie. He sported the same look of the permanently-frazzled magazine editor every time I'd seen him. He was the epitome of a cartoon character, always reminding me of J. Jonah Jameson from the Spiderman comics. All he was missing to make the look complete was the big stogie, but then again, that would have been politically incorrect nowadays.

"What's up, Dick?" I asked as I slumped into one of the chairs opposite his overflowing desk. I purposely put a slight emphasis on the 'Dick'.

"Young, I really want to thank you for submitting that last article in a timely fashion," he said, his voice dripping with sarcasm. "Getting it in that extra five minutes before the deadline was just so considerate of you." He tugged at his tie angrily and sat back in his chair, glaring at me. I was surprised I couldn't see the steam coming out of his ears.

"I aim to please, Chief."

"Try aiming a little higher next time, smart ass." He still had that irritated look on his face, and my little quip had done nothing to alleviate his sour mood. I wondered if he was gonna lean forward, start banging on his desk, and call me Peter Parker.

"Was there something wrong with the article?" I asked, confident that what I'd given him was pretty good.

"That's not the point," he replied, pointing his finger at me like a school teacher reprimanding a kid. "What kind of magazine do you think we run here, Young?"

"Uh gee, I don't know. Hardcore Nazi porn with an emphasis on amputee midgets partaking in various forms of tit bondage?"

He looked at me like I was a piece of shit on the bottom of his shoe, which I actually found pretty hard to dispute after what I'd just said. He shook his head from side to side in disgust, letting me know exactly what he thought. "Not quite, but I'll bring your suggestion up with the board of directors at the next meeting. Try again?" This time he did lean forward with his elbows on the desk, and I knew if I wanted any future work here, I better shelve the wise-guy act.

"Uh ... an entertainment magazine?" I replied, my eyebrows arching up questioningly.

"A professional magazine—that's the kind of magazine we run here." The pointy finger was coming my way again as he spoke. "And I can't be fucking around with those last minute submissions of yours every time I give you an assignment."

We'd been through this song and dance before, and I knew what my next line was. "Okay, I get it. I'll make sure I get the next one in earlier. Sorry about that last one. I was tinkering with it right up until the end. Was it what you were looking for?"

Now that I'd admitted to being a fuck-up, it kind of put him back on his heels. It's hard to stay mad at somebody when they admit to their mistakes. J. Jonah ... er, Dick, was no exception.

"Well," he said gruffly, grabbing a stack of papers on his desk, "it was actually pretty good. There wasn't much I had to cut out. Here, take a look." He handed me a copy of my article, with his red pencil marks on mine as well as the one he held in his own hand. For the next half hour or so, we went over the article and the few changes he made. I was happy. The editing had been minimal, and I actually had to agree with the changes he'd made and the minor revisions he suggested. We also looked at some pictures he'd had a staff photographer take in support of the article. They were good, shots of movies that had been made in Vegas over the last year or so. I knew they'd look great with what I'd written.

"Okay, looks good," I said finally, sitting back in the chair once we'd finished.

"I have your next assignment for you." He pushed some papers around on his desk and pulled out a single sheet with some text near the top.

"Great, what is it?"

"There's been an increase in the number of ads in the various entertainment rags and on Vegas websites lately for male escorts." As soon as his words hit my ears, I bolted upright in my chair. He saw the shocked look on my face and put his hands out in a 'calm down' gesture. "Now ... now ... I'm not talking about the gay publications and websites advertising male escorts for other males—those have been around for years. No, I'm talking about ads directed at straight people, at women basically."

"Oh, umm, okay," I replied, still feeling flustered, but trying to maintain my equilibrium that had just gone on tilt.

"Yes, they seem to be coming even more prevalent these days. I want you to do some investigative journalism and see what this is all about."

"Uh, all about?" I held my hands up as if it was obvious. "Isn't it just about sex?"

"Of course, of course," he replied with a dismissive wave of his hand. "But what's the underlying story behind the sex. What kind of people are these escorts? Where do they come from? How much do they charge? What kind of services do they provide? And what about the women who hire them? What's their story? Are they usually rich married women? Single woman who are sick of the dating scene? Shit like that. You figure it out."

"You're kidding me, right?" I actually wondered if somehow he'd found out about my Face-Painter ad and was just jerking me around.

"Is there a problem, Young? I can always give the assignment to Benning."

"Benning's a hack," I blurted out, knowing Jim Benning's work was notoriously weak.

"But a hack who always gets his assignments in on time." Morrissey sat back in his chair, pleased with his response. He reached over and picked up his phone before looking back at me. "Do you want the assignment or what? I can call Benning right now."

"I'll take it," I replied. He put down the phone. "How much do you want, and when?"

"12,000 words. I want an outline on my desk in ten days, and the finished article in three weeks. And it better be good—AND ON TIME," he said loudly.

"Okay ... okay." I got out of the chair and stood before his desk. "Anything else?"

"Have a nice day. The people in HR told me I need to be nicer to my staff." He turned to his computer screen, his hand reaching for the mouse. "And close the door on your way out."

I made my way out of his office in a daze, the shock of the assignment I'd been given still buzzing through my head. With a brief goodbye to Cara, I made my way outside, pulling out my cell phone as I leaned against Mustang Sally in the parking lot. I punched in the new number I'd put on speed dial and brought the phone to my ear.

"Hello?"

"Deanna, you're not going to believe this..."

I hit the expressway again and headed towards home, Gary Numan's 'Cars' blaring from the Mustang's sound system. I loved the sound of the soaring keyboards in that song—perfect for driving, especially with the top down. Deanna had been shocked when she heard the assignment I'd been given, and then she couldn't stop laughing. Once she started, I found myself chuckling too at the absurdity of the whole thing. She ended the conversation by saying she'd better get to work lining up clients in order for me to do my research. We agreed how funny it would be for me to actually be making money from my regular job at the same time I was making money as a professional escort.

I didn't have to meet Andy for lunch until 12:30, so I still had just under two hours to spare. I was having trouble wrapping my head around the idea of the new assignment Morrissey had given me. I still couldn't get over the bizarre coincidence of being handed such an assignment after my recent endeavors as 'The Face-Painter' in the same peculiar niche that I just been asked to investigate. I figured I'd settle down in front of my computer at home and start looking up some websites, to see the nature of some of the advertisements he'd mentioned. I'd probably start by looking at others in the website where my own ad had been placed.

I pulled Sally into my parking spot in front of the condo and climbed out, spying Margaret next door watering her flowers, hose in hand. Fuck, she was a sexy woman. Statuesque and built like a brick shit-house. She had on a pair of those stretchy shorts she seemed to like, the ones that always looked so fantastic on her. The pair she was wearing today were navy blue, the curves of her lush rear end and her long toned legs provocatively on display. Up top she wore a powder blue tank top, the form fitting garment stretched nicely over her round heavy tits. Even from across the yard, I could see the outline of her heavily structured bra beneath her top. Her red hair flowed sensually onto her broad shoulders, the soft locks framing her pretty face. Man, from head to toe, she was all woman—a perfect MILF.

"Hey stranger," she said, giving me a warm smile as she continued with her watering. I looked at her delicate hand holding the hose, remembering how she'd held mine when she'd given me that first hand job just a few days ago. Jesus, she had been good. I thought about the hot session we'd had late Friday night, and how insatiable she'd been.

"Stranger?" I replied. "I just saw you a couple of days ago."

"I'm just teasing you. Did you have a good weekend?"

"It was great, actually."

"That's good." She turned slightly until she was partially in profile, my eyes drawn magnetically to the thrusting shelf of her big tits. "And how's that hamstring you tweaked the other day? Did you find it stiffening up at all over the weekend? You know how much trouble things can be when they start stiffening up on you." I watched as she held the hose in front of her groin and slowly tilted the nozzle upwards, the water spewing forth as she brought her other hand forwards and wrapped them both around the hose. The suggestiveness of what she was doing wasn't lost on me at all. I felt my prick give a little twitch as I looked at her.

"As a matter of fact, I can feel it stiffening up on me right now," I said.

"Oh dear. That's not good." She gave me a pouty look, my eyes focusing on her beautiful lips.

"I have to meet Andy for lunch at 12:30, but this hamstring could be a bigger problem than I thought. Do you think Nurse Margaret would be able to uh ... fit me in during that time?"

She had a mischievous look on her face now. "Hmm, I think Nurse Margaret has an open slot right now that she'd be quite happy to have you fill."

"Well, this must be my lucky day."

"Why don't we step into her office," Margaret said, reaching to turn off the hose.

I followed her into her house, once again diverted from my work by a beautiful woman. Maybe I'd have trouble meeting this deadline too. "Oh well", I thought to myself as I followed her lush swaying hips into her bedroom.

"Why don't you take off those clothes so Nurse Margaret can examine you better? Get undressed and sit on the side of the bed. I think we should really take care of that hamstring before it becomes a more serious matter." She didn't even wait for an answer. She walked into her en-suite bathroom and pushed the door partially closed. I took off my clothes and tossed them onto an easy chair she had in her room, and then sat down on the side of the bed as directed, my cock feeling heavy and swollen already. A minute or two later Margaret reappeared, a towel and her massage lotions in hand. She put them on the bed beside me, grabbed a pillow, and dropped it on the floor right in front of me.

"Now, I don't want to get any of that massage oil on my clothes, do I? Where did I leave my lab coat?" She pretended to look around the room, in search of the missing lab coat. "Oh well, I guess this will be fine." She reached for her waist and pushed her shorts down before daintily stepping out of them. She them crossed her arms and pulled the tank top up and over her head, tossing it aside with her shorts. She stood before me, wearing a gorgeous matching bra and panty set made of brilliant white satin and trimmed with delicate white lace. Her tits were beautifully packed in, her full 40DDs straining at the confining material of the heavily wired bra. Her panties were cut sinfully high on her wide matronly hips, accentuating the full curves of her voluptuous body. I felt a surge in my dick as I looked at her tall buxom figure.

"Ah yes. I can see you're definitely having a stiffness problem. Let Nurse Margaret help you with that." With a sly smile on her face, she dropped to her knees on the pillow. She popped open the top of one of the tubes of oil and poured a generous of the viscous gel-like goo onto her hand. She rubbed her hands together, the warm citrus scent wafting into my senses as the lubricant started to glisten suggestively on her hands. I looked down at her kneeling before me, my eyes zeroing in on the deep dark line of cleavage between those massive succulent tits of hers. My cock lurched once more.

"Wow, this is definitely a problem." She reached forward with both hands, and I almost swooned with pleasure as she wrapped one around the thickening girth of my prick while her other warm slick hand cradled my sperm-laden nuts. Her circling hand fit wonderfully around my stiffening shaft, her slender fingers working their magic as she started to stroke back and forth.

"Oh fuck, yeah," I groaned, my cock becoming rock hard in no time flat. I leaned back, my arms straight behind me as I looked down at her kneeling between my spread thighs, her mature talented hands working me over. It was so great to have a neighbor like this who was so willing to look after me.

"That's it. Let Nurse Margaret take good care of you." She let go of my swollen nuts and brought both hands to the pulsing shaft. She wrapped them firmly around, one above the other, and then started that slow methodical cork-screw motion, her hot slippery hands sliding from the thick base all the way up to the broad flared head. Up and down, up and down, over and over, with a nice sliding twist that had me climbing the walls within minutes. Oh fuck, was she ever good. She knew just what to do with a cock. I tried to suppress the delicious feelings I was experiencing, but it was useless. I felt my balls drawing up close to my body and knew I was close.

"Oh my God. I'm gonna come already," I gasped, my heart racing as she mercilessly continued to jerk me off, her wonderful hands keeping up the same smooth teasing rhythm she'd been using all along. The contractions started and I felt my stomach muscles flex as I went off, a long thick rope of white cum shooting high into the air.

"That's it. Let it go," she said softly, her hands continuing to stroke deliciously up and down. I shot again, and then again, a fountain of semen spurting high into the air before falling, the gobs and ribbons of milky seed landing erotically on my stomach and her stroking hands. "That's the way. Give Nurse Margaret every thick creamy drop." She kept pumping, and I kept shooting, wad upon wad of jizz spewing forth. Her mature hands felt absolutely fantastic as she continued to jerk me off, her slender fingers pulling as much cum out of me as I had to give. My stomach and her hands were a gooey mess, but I kept coming, until finally, the last oozing wads of silvery cream spurted forth, sliding down from the oozing tip and over her cum-covered hands.

"I better take a sample of this for testing," Margaret said as she leaned forwards and started licking my stomach. I sat there, trying to slow my beating heart as I watched her lick up my cum. She slurped it up wantonly, her lips and tongue searching out every stray drop. When she was finished cleaning my stomach, she started in on her hands, licking the warm milky goo off the backs before sliding her semen-covered fingers deep into her mouth, her lips closing around each slimy digit as she swallowed my potent swimmers. It was incredibly erotic to watch, the sultry wanton look on her face keeping my cock just as hard as it was before I came.

"Oh dear, we don't seem to have solved your stiffness problem," she said, her hand slowly stroking my still-hard prick.

"Now, where is that slot of Nurse Margaret's that she wanted me to fill?" I reached down and pulled her onto the bed, throwing her onto her back as I scrambled between her legs.

"It's right here," she said teasingly, drawing her legs up and letting them roll open as one long red fingernail came down and traced provocatively over the front of her panties. I could see they were soaked, her womanly cleft visible beneath the damp fabric. "You'd better fill that slot in a hurry, before somebody else does."

I reached down and pulled her panties off as her warm womanly aroma filled the air, the intoxicating scent firing my libido even more. I tossed her panties aside and moved between her thighs as she opened her legs right up for me. I leaned forwards and angled my rampant cock down towards her waiting flower, the brilliant pink petals of her labia glistening wetly. I could feel the incendiary heat of her flowing juices as the broad flared head nestled between her parted lips, the sensitive tissues of my glans bathed by her oily juices.

"Oh yeah, that's it," she said in a deep breathy voice. She slipped her arms around my neck and pulled my face down to hers, giving me a hot passionate kiss before dropping her head back onto the pillows and looking up at me, her eyes alive with wanton desire. She rolled her hips slightly, making the helmet-shaped head fit perfectly between the gates of her beckoning cunt. "There, perfect. Now give it to me nice and slow. I want to feel every hard inch going all the way inside me."

Not wanting to disappoint her, I flexed back and slowly drove forward, sliding inch after inch of hard thick cock into her oily depths. Yes, at just a couple of years south of 50, she was the perfect MILF neighbor.

"Ohhhnnn," she groaned deep in her throat and her head tilted back as I went deeper. She brought her knees further up, opening herself as much as possible for my slow merciless onslaught. She was luxuriously hot and incredibly wet, the steaming oily tissues inside her parting reluctantly as I slowly flexed forward, until the final few inches disappeared, over 10" of steel-hard cock buried inside her.

"Oh my God. I absolutely love how big and hard you are," she said as she looked into my eyes, a fine sheen of perspiration breaking out on her forehead. She looked incredible, her shimmering red hair framing her pretty face attractively. She had a wicked little smile on her face as she looked at me and spoke, "Just stay still for a minute. Let me work it, okay?"

"Whatever you'd like," I replied, letting her know I was willing to do whatever she wanted. She rolled her hips slightly, and I could feel my rigid prick settling just a fraction of an inch deeper into her. She started to work the muscles inside her mature talented cunt, and I felt a wonderful massaging sensation as she tightened down. A luxurious rippling seemed to roll in delicious waves along the full length of my buried cock as she started to really work it with that talented cunt of hers. Oh man, this woman was incredible. I'd made love to many women in my young life, but the only one I could compare to Margaret was my mother. Both of these beautiful mature women were absolutely amazing lovers. I guess there was a lot to say for experience.

"Oh, that feels so good inside me," she cooed, bringing her legs up and wrapping them around me, her heels crossing over my backside. She flexed her hips up and rolled them in a slow tantalizing circle as she continued to work me over with the muscles inside her.

"Oh fuck, Margaret," I said, unable to take her delicious teasing any longer. "That feels incredible." I started to move my own hips, settling deep in the saddle as her cunt continued to squeeze and pull at me. She smiled at me like a sultry enchantress as I slowly drew back, the hot oily tissues inside her clinging to my withdrawing dick possessively. Her cunt-lips nibbled at the broad tip as I pulled almost all the way out, and then slowly drove the full length into her once more.

"Yesssssssss," she hissed as I powered my way all the way into her, the hot folds of flesh inside her pussy enveloping me like a hot buttery glove. I pulled back and drove it into her again. With her legs crossed over my back, she lunged back at me, thrusting her hips upwards as I really started to fuck her. I gave her good hard long strokes, knowing she loved it when I touched bottom every time. She was breathing rapidly, her mouth gaping open and her eyes closing in bliss as the delicious waves of pleasurable sensation rolled over her. She was still wearing her bra, her 40DDs delightfully enhanced by the sexy garment. I loved the look of a spectacular set of tits beautifully on display beneath a sexy bra. I was in no hurry to have her take it off. Her bra-encased tits looked sinfully erotic, the upper swells jiggling and shaking sensually as we fucked, her stiff nipples enticingly visible through the shiny white satin. Perfect. With my eyes feasting on that mouthwatering set of tits, I flexed back and then slowly drove forward, angling my rigid prick up so I was concentrating on the hot slick tissues on the roof of her vagina.

"Oh God, that is so ... that is ... OH FUCKKKKKKKK," she moaned loudly as she started to climax. I felt her fingernails clawing at my back as she started to convulse and gyrate like a wild thing. Her hips were twitching and bucking as her orgasm overwhelmed her. I held on to the excruciatingly delicious ride, my body moving with hers as I fucked her deep and hard. I felt like I was riding a bucking bronco, her wide matronly hips pistoning themselves up and down recklessly, my hard thick cock rubbing fiercely against the hot folds of flesh inside her.

"Jesus, this woman is something else," I thought to myself as her mature flexing body had my balls drawing up in anticipation of my oncoming climax. She must have sensed it, because she quickly spoke up.

"If you're going to come, I want it on my face," she purred out breathlessly. Man, I think those were my favorite words in the English language. With those tell-tale contractions starting in my midsection, I quickly withdrew and scrambled up over her until I was straddling her, wrapped my hand around my surging cock and pointed it right at her face. I barely had time for one stroke before a long white rope streaked forward, slamming forcefully against her cheek.

"Aaaahh," she gasped as I fired again, the next ribbon of semen running all the way up her face and into her red hair. I pumped my hand back and forth as I unloaded, flooding her face with a warm fresh dose of milky protein. Strand after strand of silvery goodness spewed forth as I moved the head of my dick from one side of her face to the other. She opened her mouth and I directed one shot right between her ovalled red lips, and then went back to painting, sluicing the spitting jets of white semen all over her. I pumped and pumped, the milky seed raining down upon her face. Finally, as the last tingling shiver ran down my spine, I sat back and flicked the final drops down onto the upper swells of those beautiful tits of hers.

"Oh my God, I love that," Margaret said softly as she brought her hands up and started massaging my cum into her skin. She was a mess. Milky gobs and pearly ribbons crisscrossed her face erotically. Silvery strands clung to her lush red hair, while her sumptuous chest was spackled with random wads of glistening pearly semen. All in all, she looked perfect.

"Connor, you can do that to me any time you want," she said, pushing a wad down each cheek and into her waiting mouth. I helped her by scooping up the warm milky gobs on her chest with my fingers and slipping them into her mouth, loving the feel of her soft lips closing down and sucking at my fingers. Soon, she had it all inside her, a thin layer of shiny semen drying on her pretty face.

"What time is it? I have to meet Andy at 12:30 at Gabriel's for lunch." We both turned and looked at the clock on her bedside table: 11:43.

"You've still got about a half hour before you have to leave," Margaret said softly. "But I think you need a shower before you go." She slipped out of bed and made her way towards the en-suite, reaching behind and unhooking her sizable bra as she did. Just before she went through the door, she stopped and looked at me over her shoulder, and then tossed the bra back towards the bed, allowing me just a teasing glimpse of her heavy round tits in profile. "Care to join me?" With a wicked little smile on her face, she disappeared into the bathroom and I soon heard the shower running.

I sat there with a big smile on my face, blissfully savoring the feeling of post-orgasmic bliss. When I heard her close the shower door, I knew it was time to join her. Margaret's place was almost an identical layout to my condo next door, and I knew she had a big walk-in marble shower like mine, more than enough room for two. I entered the shower and quietly closed the big glass door behind me, savoring the view of her tall mature body standing beneath the pelting spray of the shower. She had both the dual shower heads going, and the space was quickly becoming erotically steamy. She was letting the powerful pellets rain down upon her face and head, her hands raised up beneath her flowing red locks. With her arms lifted up like this, it caused her huge tits to thrust forward enticingly. I felt my fingers just itching to get at them as I moved in close behind her.

"Mmmmm..." She mewed like a little kitten as I nuzzled into her neck, my lips caressing the soft skin of her neck, the alluring scent of her hair wafting into my nostrils. She turned her face towards mine and I kissed her passionately, my tongue sliding deftly into her hot welcoming mouth. We both gave off soft moans as we luxuriated in the feeling of the long sensual kiss. Finally, we parted, both of us gasping. I watched over her shoulder as she thoroughly lathered her hands, and then she passed me the bar of soap. I did the same to my hands, working up a soapy froth before setting the bar back down into one of the little shelves built into the sides of the shower. I slid my hands around her mature body from behind and up over her toned flat stomach, my slippery hands drawn magnetically to those tremendous tits of hers.

"Mmmm ... nice," she purred as my slick hands cupped and hefted those big round beauties. Man, they were heavy. I ran my hands all over them, gently squeezing and hefting, and then allowing my fingers to seek out her sizable nipples. I circled the stiffening buds with my soapy index fingers, loving the slippery warm feel of them coming alive beneath my touch. Her own hands slid down my sides as she reached behind, her soapy fingers caressing my flanks deliciously as her hands made their way towards my midsection. As I ran my hands beneath the massive globes once more and hefted them together, I was surprised to feel another tingling lurch in my cock.

 
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