Lennie and Samantha - Cover

Lennie and Samantha

Copyright© 2025 by dawg997

Chapter 17

Erotica Sex Story: Chapter 17 - An older man, who found financial success later in life after enduring years of anguish, grief, and bitterness, unexpectedly meets a stunning, high-end escort at an upscale bar. Neither had sought love for over a decade, their pasts having long since closed that door. Yet, what they had both stopped believing in suddenly seems possible. Two very different worlds collide.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Fa/Fa   Mult   Coercion   Consensual   NonConsensual   Rape   Romantic   Lesbian   BiSexual   Heterosexual   Fiction   Uncle   Humiliation   Rough   Sadistic   Gang Bang   Group Sex   Harem   Orgy   Interracial   Black Male   White Male   White Female   Anal Sex   Cream Pie   Double Penetration   Exhibitionism   Oral Sex   Prostitution   Violence  

Shauna was nervous. She had played up her escorting experience with Samantha because they needed the money so badly, and figuring there were many women vying for the single position Sam had available, she thought that bragging about her experience would give her a leg up on the competition.

“Sam, if you hire me, you can put me to work immediately. I’ve sold myself many times over to all kinds of men, young, old, white, black, sexy, and out of shape. I can make them all cum hard. I love it when a man loses his cool and blasts a load inside me.”

“It sounds like you’re experienced. Do you want to hit the ground running? There is a gangbang scheduled in a few days. It’s one of my regulars who is holding a bachelor party for his nephew and about twelve or thirteen of his friends. It’s going to be a no-holes-barred event, pun intended,” Sam laughed. “A gangbang like that is hard on a girl, but you can make one hell of a lot of money for a single evening.”

“Really? Fourteen or fifteen guys? What do they expect of me?”

Shauna was both excited and a bit apprehensive. Her experiences years ago always had her pleasuring a single man, or maybe two. Fifteen guys is a lot of fucking and sucking. The first thought she had was how sore she would be the next morning. She thought about the scene, like it was some obscene porn she watched to understand the job she accepted, and took a deep breath. Samantha continued to talk.

“They expect everything. They are all new to the escort service, so even though they had an initial STD test from our registered nurse, that doesn’t clear them to go bareback. They will all use condoms for vaginal and anal sex. They do expect you to give them bareback blow jobs. His uncle Jeffery, however, will completely bareback you because he’s one of our regulars.”

Shauna registered what Sam was telling her and nodded. Her mind shifted back to her college experiences, especially that one gangbang she performed. She would never forget it.

“So yeah, you’re expected to perform as wild as you can. Lots of swallowing cum, multiple guys at the same time, anal. The wilder, the better. This is what we call an ‘unlimited’ gangbang. The guys get to have as many chances with you as they want to, up to three times each. Only about half of the guys go for that many times though, because most guys can’t get it up a third time within a few hours if you are doing it right. In any case, for this show, there is a four-hour time limit. Do you think you have the stamina to deliver?”

“Yeah, Sam. A lucrative gangbang?” She threw her shoulders back and looked directly into Sam’s eyes, her confidence brimming.

“There’s no time like now to make money. I’m an experienced whore. I love taking on multiple guys. If it’s a gangbang you’re selling to these guys, I’m your gal.” She said it with nervous excitement.

“That’s the attitude!”Sam replied. “You’re right, there is no time like now. Girl, you already have the job; don’t feel like you have to prove anything to me.”

“I admit I’m a bit nervous, having not been escorting for seven years. Truth be known, I’ve done a dozen-man gangbang before; I can handle it.”

“OK, Shauna, if you’re sure, I’ll call Taylor and tell her she has the night off.”

Shauna had a look of concern on her face. “I don’t want to steal business from another girl, Sam.”

“Don’t worry about Taylor. She will understand. Like I told you earlier, we work together as sisters to provide our clients maximum pleasure, not in competition with each other. Samantha’s Escort Service turns down more clients than we service, because of our reputation as the best courtesans anywhere. Just provide the best service you can for every client. When you go out as an SES girl, you are representing all of your sisters and the reputation of the service itself.”

Shauna smiled, realizing she was going to get her brains screwed out. She hadn’t had hard, pounding sex in over a year since her husband was injured. It was like going from zero to one hundred miles an hour in an instant.

Shauna had her carry bag, with multiple pairs of panties and thongs, two sets of lingerie, lots of lube, and four dozen condoms in two different sizes. As she walked up to the huge home in an upscale neighborhood, she took a deep breath and knocked on the door. She could hear laughter and music inside. A man in his early 50s answered.

“You must be London,” the man said, excitement in his voice as he stared at the tall, sexy, light-skinned black woman standing in front of him.

She flashed her brilliant smile and replied, “Yes I am. Jeffery?”

He smiled and reached out to shake her hand. “That’s me. Wow! DJ was right; you are a gorgeous woman. She promised me I’d be impressed, and she didn’t let me down, that’s for sure! I told her I needed a perfect “ten” who was young. I love Taylor, but she is too old for these guys, to be honest. But you, my god! What are you, twenty-two?”

“You’re kind, Jeffery, I’m twenty-eight.”

“Fucking Sam! She did it again! She found another woman who looks younger than her real age. Don’t just stand there. Please, come in. Let me take your bag.”

London was wearing a classy, well-fitting bodycon dress with a low-cut top to show off her massive cleavage and the sexy, light-brown skin of her arms and shoulders. The dress hugged every curve of her body, showing her shapely hips, flat stomach, and tight waist. She stepped into the living room and gave Jeffery a twirl to show off the goods. She slowly slid one hand down the side of her dress over her hip while she flipped her hip to one side in a sexy “look at this!” pose. Samantha’s longtime client looked at her, and his eyes bugged out.

“Holy fuck! You’ve got an incredible body! I could stare at your beautiful face for hours! You’re perfect!”

“Thanks, Jeffery,” London purred. “Is there someplace where I can change and get ready?”

“Sure, let me lead you to a guest bedroom. There’s a full bathroom there, as well. Use it as your own, nobody will be able to access it when you are entertaining. I’ll keep it locked. Come around this way and down the hall, so the boys won’t see you. When you’re ready, just walk out and surprise them. I’ll take care of the music and put on your playlist.” London nodded, appreciating the support front this new man.

“To talk about business for a second, I have a credit card on file with Samantha and expect it to be charged $20,000 as I agreed to with DJ. Of course, that doesn’t include tips from the boys. After looking at you, all I can say is to expect a lot of tips.” Jeffery leered at the beautiful black woman, and London pushed her tits out for his approval, to acknowledge why she was there. He smiled, and she smirked at his smile.

Shauna did a quick calculation in her head. Samantha said the rate the client was charged was $2,000 an hour. Twenty thousand? For four hours? Shit! That’s incredible! Shauna thought.

Jeffery led London through the kitchen to the hallway, bypassing the living room where the party was located. She quickly stripped and slipped on a see-through red lingerie set with red stockings and garters. She pulled the lube out of her case and liberally lubed her ass and pussy, then wiped off the outer area to make it look dry again. Grabbing a box of a dozen regular-sized condoms as well as a dozen extra large ones, she pulled her red thong over her garter, put her 4-inch black heels on, and walked out the door.

Jeffery was waiting in the hallway.

“Oh fuck! You’re so hot! Wait for about one minute for me to get the boys under control, and when the music is turned down and your playlist starts, make your entrance.”

She heard Jeffery yell, “Okay boys, the entertainment is here!” Suddenly the loud talking dropped to a murmur, and the music was turned down low.

Her high heels clacked on the wooden hallway floor. She slowly turned into the living room, and the place erupted.

“Woo! Woo!”

“Will you fucking look at that!”

“Geezuz, what a fucking body!”

“Oh damn! That’s the face of a goddess!”

London held her head high and boobs out as she slowly strolled into the large living room. The furniture had been rearranged so the middle of the room was wide open for her to dance and shake. Couches were on either side, about ten feet apart, with a large easy chair at one end, for the groom-to-be.

“So,” she purred in a sexy, almost hungry voice. “I heard someone is getting married. Now who might that be?”

All dozen guests pointed to a man who was standing in the middle of the room.

“This is your guy! Go get her, Jeremy!” A couple of them shouted, pushing him closer to her. She slowly slinked up to him, shaking her giant, poorly covered tits a foot away, and said, “Come here big boy, cop a feel of these.”

The boys whooped, clapped, and hollered. Someone turned the stereo up again, playing some hip-hop music with an urban beat that London had never heard before, but it was perfect to slowly shake her ass back and forth. She grabbed the back of Jeremy’s neck, and pulled his face into hers, giving him a scorching wet kiss. The boys went nuts. She continued by pushing his face down to her gigantic tits, mashing his face between them. Still wearing the see-through bra, her nipples began to harden and stick out, rubbing on his face. The boys got even louder. He started groping them while he fondled them, kissing and licking them through the thin material.

She maneuvered him to the chair and pushed him down into it. He fell and yelled, “Oomph,” as the air was knocked out of his lungs when he hit the seat. She gave him the lap dance of his life, grinding her body into his face, encouraging him to grab her wherever he wanted. He sat low in the chair, his legs stretched out, and she lifted a leg over and dropped down to ride his crotch. She gave him a steamy wet kiss as he groped her breasts.

“That’s it, big boy. Take those titties and suck on them. They’re the last set of strange titties you’re going to get. Enjoy them!” She held his head close to hers and whispered in his ear, “I’m gonna fuck the shit out of you, big boy. I’m gonna fuck you so hard, you’re not gonna be able to get it up for days.”

Jeremy groaned but kept sucking and fondling the massive, firm globes.

After a long time groping and licking them, London got up and turned around, shaking her nearly-naked ass in front of his face, and then, standing between his legs, dropped her butt down to his crotch. She kept the beat, her fine ass grinding on him until she felt a hardness poking back into her. The boys were getting out of control, yelling all kinds of nasty things. London smiled and kept it going, egging on the boys. Once in a while, a stray hand brushed over her body, but she never tried to stop them. It just made the temperature in the room hotter.

She got off of his lap and told the guys to sit down if they wanted to touch her. They sought out the best seats on the couch; a few sat on the floor. She started to bump and grind around the room in front of the other guys, letting hands grope where they wanted to. After twenty minutes of sexy shaking her body and letting the guys touch her ass, legs, tits, and tummy, she went back to the groom and shook her ass in front of his face. She reached under the sides of the thong and slowly pulled it down, her ass still inches from his face. As she stayed bent over, Jeremy could see her pussy lips and asshole in front of his face. He reached up and slipped his finger into her pussy, and she moaned and slithered all over the finger.

“Another finger, Jeremy. Slip another finger in my pussy and rub it.” He did exactly that. She moaned again and said, “Now, pull it out and taste your fingers. Do you like it?” The whooping and hollering subsided, and the guys watching the encounter stared and started panting. London had every guy in the place wishing they could be Jeremy. They also knew that soon, they would get their chance with this prime piece of perfect pussy.

While Jeremy slipped his fingers in and out for another taste, London slowly shook her now-naked ass around for the other guys to sample one by one. Each guy had a minute or two to duplicate what Jeremy enjoyed.

Some were too rough, sticking their fingers in her pussy and as she jerked away, telling them, “Hey boys, that’s USDA Prime, so show some respect for it, okay?” She kept her sexy smile as she gave the soft warning. After a couple of times with her backing off a finger that was too rough, they got the message and were more careful when sampling the goods.

After making sure every guy copped a good feel and tasted their wet fingers after sliding in and out of her pussy, she went back to Jeremy and removed his shirt, then untied and tossed his shoes and socks. She pulled him up out of the chair and dropped to her knees, unbuckling his belt and pants. Pulling them down with his underwear to his ankles, she pushed him back into the chair, his cock hard as a rock. She slowly started stripping her lingerie off, then her sheer silk bra, until she was naked except for her garters, stockings, and heels. She grabbed his head and leaned forward, shoving her pussy into his face. The guys whooped and hollered again, shouting obscenities and telling him what to do next.

“Eat that pussy!”

“Finger it, shove it deep into her!”

“Rub that pussy on your face! Get your face wet!”

“That body is fucking perfect!”

London pulled her now-naked body over the sides of his chair, her legs wide and her pussy inches from his face. She leaned forward, shaking to the background music the entire time, and shoved her wet snatch into his face, grinding and rubbing her wet core all over it. In seconds, his face was drenched with pussy juice. London was having as much fun as any of the guys.

“Eat me, baby. Eat that pussy, that prime pussy. Work your tongue inside of me. This is the last strange pussy you’re ever gonna have, honey. Get it, taste it, and go for it. It’s all yours.”

The guys started screaming, the obscenities louder and more foul. She grabbed his hands and pulled them to her tits, swaying above his head. The combination of eating pussy and fondling those massive, firm tits had him harder than nails, and the guys got out of control.

“Eat it, eat that pussy!”

“Grab those tits, those giant fucking tits!”

“C’mon Jeremy, time to fuck that prime piece of ass!”

She turned around and gave him a deep, massive kiss. His face had a look of deliriousness, as if his mind were somewhere else and detached from reality. She bent back over him and reached for his stiff dick, fondling it and then licking it, starting with the head and then going up and down the length until it was sloppy wet. He groaned as she continued.

Making a quick judgment, she reached down to one of the two small boxes near her on the floor—and found—a regular-sized condom with one hand while still jerking him with the other. Without him realizing it, she ripped open the foil with her mouth and put it in, then rolled it onto his hard dick with her mouth. He never realized he had a condom on.

London was that good.

She pulled him out a bit so his head was lying low against the back cushion, making his lap accessible and easy to mount his cock. She positioned herself over his hard-on and slid down in a single, slow stroke. It was easy because she was wet from the excitement. She started humping him, slowly gliding the length of his 6 inches, until she bottomed out. Holding that position for a while, she was able to bend over and give him a deep wet kiss again, their tongues twisting together, trading spit.

His hands found her massive breasts again, and he fondled them as they Frenched. Her pussy was steadily stroking his cock in and out as she rode him as the guys watched the cock slide in and out like a scene from a porn movie. Except this was live and in living color, just feet from their eyes. They became silent, watching their friend fucking this beautiful female body. Jeremy held out as long as he could until he started groaning. London sensed it, and knowing that she had a dozen other men to fuck and suck, she rode him hard until he blasted his big load into the condom. She continued to kiss him and ride him until he started getting soft, and then finished him with one last, deep wet kiss. He just lay there, mind-blown, as was his wad of sperm. The guys started whooping and yelling again.

She rose up and carefully pulled the spent condom off his softening cock. She reached down to twist it, keeping the cum secure as she tossed it to the floor, and then reached down to lick his cock clean. Sucking it like a baby calf drinking from her mother’s teat, she cleaned it completely and then surprised Jeremy by kissing him again, this time with cum on her lips. He didn’t fight it, and the guys cheered again.

“Let me take a break, boys. Can a girl get a drink around here, maybe a whiskey on the rocks?” she queried. Within a minute, a hand appeared with a drink in it. She took it and sipped the whiskey, the cold, mild burn feeling good as it went down. The guys were staring and panting.

“Okay, boys, who’s next?” She finished her drink as the guys struggled to get out of their clothes and some started jacking their cocks. Out of nowhere, a large mattress with a bottom-fitting sheet was tossed to the floor between the couches.

“Okay boys, I’m ready. I can go two at a time, one down the gullet and one up the snatch. Come on, boys, who’s first?”

They jockeyed positions to be first. London lay down on her back, turning to one side as a cock was pushed into her mouth while another cock slid into her pussy, that cock inside another condom. Her pussy was soaking wet, and the sheathed cock easily slid in and out of her. She slobbered onto the cock in her mouth, pulling the seven-incher all the way down her throat, until her nose was buried in pubic hair. When her nose was buried deep in the pubic hair, they cheered again. Within ten minutes, both had cum. She had swallowed the load in her mouth and liked the taste.

“Must eat a good diet,” she thought to herself.

She removed the spent rubber from the cock in her pussy and licked him clean. The two spent cocks were replaced with two fresh, hard dicks. The guys were egging on the two men engaged in fucking her holes, and when they were finished and replaced, the next pair were cheered on as well.

She turned over and was on her knees and elbows, bent over to accept another cock in her pussy while she slobbered down another cock in her throat. The cock in her pussy lasted nearly twenty minutes, but the cock down her throat blasted cum in her mouth within five minutes of getting sucked. She moved around again to toss one guy on his back and mounted his condom-sheathed cock while blowing another guy who was standing beside her. Again, two cocks blasted cum, one in the rubber and one in her mouth. That cock shot bitter cum, as he was a smoker with a bad diet. No matter, she was a whore who was proving she was a world-class cocksucker and fuckhole. Bitter-tasting sperm was simply a condition of the job.

Within 90 minutes, every man had cum inside one of her holes. They took a break, getting drinks and exchanging bragging rights. The uncle pulled her up and gave the nude woman a kiss, remnants of semen from a half-dozen men still in her mouth. He pulled her up and held her as she stood, leading her into his guest bedroom, where she had set up her base from which to operate.

“Hey, Uncle Jeffery, where are you going?” Jeremy shouted as his uncle led the naked woman back to the bedroom.

“I’m going to have my time with this beauty, and since I’m paying for it all, I’m going to have some privacy. We will be back in about a half hour.”

The guys moaned but kept drinking, realizing they were in no position to complain.

“God, you’re beautiful, London,” he said after the bedroom door closed. “I want to enjoy you. I can’t wait to feel my naked cock sliding down that incredible pussy of yours. Fuck you’re hot.”

He tossed her onto the bed, and she bounced on her back, giggling. He never bothered to pull back the comforter, instead stripping quickly and lying down beside her. He gave her another long, deep kiss as he fondled her naked body. After a few minutes, they broke for air. London was curious.

“You watched me suck off a dozen guys and swallow their cum. Doesn’t that bother you?”

Jeffery let loose a deep belly laugh and looked into her eyes. “No, not a bit. Oh, that’s right, you’re new to Samantha’s, aren’t you?”

London nodded, a bit embarrassed she didn’t know something about the escort service she worked for.

“Some of her long-time clients have gangbang parties, and there isn’t a condom in the entire house or hotel suite because we do everything raw. Tasting another man’s cum is something I’m used to. No worries. Now come here. I want to fuck you for a while until I get close, and then I’m going to fuck you in that amazing ass of yours.”

London just smiled and went back at it with him. Samantha had told her she would be doing anal. After a long pounding and her cumming twice, he withdrew his cock and told her to turn over doggie style. She had reached into her bag for lube, but he stopped her.

“No, I want to get my dick wet by fucking your pussy, but first, I want to lick your asshole and that perfect snatch of yours. Fuck, you’re perfect.”

He fondled her athlete-class buttcheeks, staring at her light brown skin, the feminine curves, her two holes. He leaned forward and licked her a dozen times or more, her holes now sopping wet from both of them.

“You have the perfect ass. Sam and the girls have perfect asses too, but personally, I myself would like some milk-chocolate ass. You’re fucking heaven, London.”

London said nothing but smiled and nodded. This man was obviously important to Samantha’s Escort Service. She knew because he footed the entire bill for the evening and also how Sam had described him. Important men who were repeat customers should always get what they want, and Jeffery wanted London’s ass raw and without lube, although there was some remaining before she started for the evening. That’s what he received. She groaned as his eight-inch cock slid into her butthole, but she could tell he was a master, going slow and stopping when he could sense her tension.

After a while, she would relax, and he would continue plunging into her backside. When he was in completely, he held his position, not moving until London started to slowly move up and down on his dick. Before he started pistoning her, he leaned forward, reaching down to her clit and started forcefully flicking her female knob. She climaxed with a scream in minutes. The sex was amazing for both of them, and finally, he tensed up, groaned, and grunted a huge load into her bowels. He stayed hard and inside her long after he came. Finally, he pulled out and laid down beside her, fondling her breasts and kissing her deeply. After that groping, she sat up and leaned over to his soft cock, licking it clean.

“You’re fucking amazing, London. I’m going to have you again and again. Damn, you’re sweet.”

A half hour of kissing, groping, and licking later, the two walked back into the party. The guys had recharged and were ready for another round. It was more graphic and nastier than before, and London loved it. They were double-penetrating her, their sheathed cocks in her asshole and pussy. A couple of times she was riding one cock in her pussy while a second was nailing her ass from behind, and a third guy was standing beside her as she sucked him dry. She was airtight three or four times that night; she lost count in the sexual frenzy. Half of the guys were able to go a third time, but not with the intensity of the first two. London was getting sore and worn out, but she never complained. After the guys finally said they couldn’t get it up, she finally went to her room, kissed Jeffery for a while, who enjoyed fondling her body, and got dressed.

She walked out the room and down the hall, wearing her bodycon dress and 4-inch heels. Her hair and make-up were flawless after a quick, 10-minute stop in the guest bathroom. Jeremy was passed out on the mattress, drunk and naked. His friends saw London walking out, and like the Pied Piper leading a pack of lemmings, they all got up from where they were sitting or lying and came to touch her one last time. She recognized what was happening and immediately stopped to take in the admiration, shown by more than a few pokes, pinches, and fondles of her body as she kissed each and every one of them one last time.

“London!” one of the leaders of the pack said to her as he hugged her and rubbed her ass.

“Oh my gawd, thank you! This has to be the best night of my life! It may have been Jeremy’s bachelor party, but unlike him, I didn’t drink my ass off and I will remember you forever! Here, let me give you a tip.” He looked in his wallet and saw eight one-hundred dollar bills, plus a couple hundred in smaller bills. He pulled it all out and handed it to her.

He had an embarrassed look on his face. “I’m sorry, this is all the cash I have. You gave me the night of a lifetime. I could never know that life could be this good. If I win PowerBall and share it with you, will you become my wife?”

She paused for a few seconds and laughed to herself. Nobody else could see her emotion because she was a professional.

“What is your name again?”

“Allen.”

“Allen, I’ll tell you, I’ll consider it, okay? You were a prince helping me by keeping the guys in check and still letting them have fun. And you are hung like a horse and know how to use it. So why would I say no? At least I’ll keep my options open.” She giggled when she said it.

“London, do you have Venmo by chance?”

“No, but a friend of mine does,” she lied. She had a Venmo account, but it was her real name.

“If you give me their account, I’ll Venmo you another grand, and she can give it to you if that’s okay. I want to tip you what you’re worth.”

Shauna was shocked at what he said but decided another grand was worth the risk.

“Sure, the name is ShaunaBritton3, and it won’t be a problem. I’ll call my friend when I’m going home and take care of everything.”

“Great! Hang on for a few minutes, okay?” He turned to the guys, ten of the thirteen were still conscious. “Guys, London needs to get tipped. Open your wallets and give your cash to her; do it now.”

Everyone was so wiped out, both from drinking as well as the most amazing sex they ever had in their young lives, just following their friend’s request. Guys tossed their cash in a pile on the table, from $400 to $2,600. The pile totaled a bit over $12,600.

“Oh fuck, you cheap bastards, except for you, Scott, Stuart, and Steve. The rest of you, pull out your phones now and Venmo London another grand each. Right now, you cheap bastards. This was more than the best fucking sex we’ve ever had in our lives. This is the greatest event of our lifetime. If you assholes don’t tip London what she is worth, I’ll be on your ass about it forever.”

The combination of his influence in their group of friends, their sated sexual imaginations, and their on-coming hangovers made them follow Allen’s demand without argument. In about five minutes, Saundra looked at her Venmo balance and saw it had increased by another ten thousand dollars in addition to his thousand on Venmo from Allen. In total, she had made $23,600 in tips alone. She thought about her meetings with Samantha and remembered she didn’t have to share tips with the house. That meant in addition to the tips from the group and the five grand from Jeffery, she was making two-thirds of twenty grand. Holy crap! That was over forty grand for the night!

There had to be a catch, she thought. No working girl could ever make this kind of cash. She remembered her dealings with her old service when she was escorting as a UCLA student. The owner would always come up with “exceptions” and a big payday would be mysteriously cut in half. Shauna was conditioned to think the same thing would happen again. She was going to talk with Sam immediately when she returned home. “This would tell her a lot about whom I’m working for,” she thought.

After she gave one more round of hugs and kisses, where the men all felt her up, she kissed the sleeping groom and walked out to her car.

She walked into her living room, and Sam looked up, lying with DeShawn. “Oh, hi, honey. How did your night go?”

“Great! Beyond my wildest dreams! Sam, can we talk privately for a minute?”

Sam got up, and they walked into the kitchen. Her voice was low so nobody could overhear her. Which means exactly one person, Deshawn.

“I have a question for you. You had mentioned the splits and everything about getting paid.”

“Yes, dear, I did. Do you have a question about what we talked about?”

“Well, yeah. So according to Jeffery, he paid a flat twenty grand on his credit card through DJ, and that was the retail price for my services without any tips. So I pay the house a third of that and I get the rest?”

 
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