The Cad - Cover

The Cad

Copyright© 2001 by Klaude Smith

Chapter 29

Erotica Sex Story: Chapter 29 - Jake loves his girlfriend, Josie, but can't seem to keep from hooking up with other women.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Ma/ft   Fa/Fa   Mult   Consensual   Reluctant   Lesbian   Heterosexual   Cheating   Exhibitionism   Voyeurism   School  

Frank sat in his seat after the bell rang, in no hurry to get up and disturb the pleasant daydream he was having, remembering Cindy's body in his hands from the night before. Around him the other students were collecting their books and chatting away, but he was lost in his thoughts, a goofy grin on his face.

True, his gorgeous girlfriend (he could call her that now, couldn't he?) hadn't yet yielded to his ultimate request, but she gave every indication that she would eventually. Cindy was just being careful, he told himself. She'd told him that she just didn't want to rush anything. They'd only been dating for a couple weeks, after all.

Maybe he was pushing her too hard, pressing for too much too soon. But it was difficult to hold back when they were together, she was just so sexy. Frank had actually gotten to fondle those awesome breasts again, something she hadn't allowed him to do again since that first night at the party. He sighed, remembering the wonderful combination of soft and firm in his greedy hands.

She'd seemed to get into that quite a bit, actually. It was only when he'd gone too far, reaching between her legs, that she'd shut him down. He'd sort of embarrassed himself, practically begging for access to her forbidden zone, and looking back he knew that she offered the handjob purely to get his mind off of that goal. Sure, it wasn't as nice as a blowjob, but Cindy's hands had done the trick, and he'd shot his wad all over her carpet.

Afterward they'd cuddled and spent the night talking. It was hard for him not to try to make a move on her again, but he really couldn't complain. He felt pretty frigging lucky, remembering how nice it had been to wake up next to her.

"Planning on auditing my next class, Frank?"

Frank shook his head clear and turned to look at his professor, who was addressing him from the podium. Students for the next lecture were filing into the room.

"Um, no sir," Frank stuttered, grabbing his stuff. "Just reflecting on our reading." He grinned, shuffling past the incoming students to get to his next class.


Now, as Frank walked home, he was feeling a tremendous letdown. Cindy had met him after class, as promised, only to tell him that she couldn't see him again tonight; she was going out with the girls. Horny and frustrated, Frank could only meekly acquiesce, settling for the promise of a phone call tomorrow. It looked like he'd be the one administering tonight's handjob.


"Well, he seemed to take that pretty well," Monica said once Cindy had sat down next to her on a bench in the courtyard. She'd seen her talking to Frank from across the yard, aware that the handsome young man was getting the brush off.

"As well as can be expected, I guess," Cindy sighed. "After our little talk this morning I really feel like I should cut him loose, the sooner the better. I don't want to lead him on or anything."

Monica shrugged her shoulders, and Cindy smiled. Cindy was a very attractive girl, Monica thought to herself. Guys like Frank would always be falling over themselves to go out with her.

"I don't know what to tell you about that, sister," she said with a shrug.

"Oh, I'm not asking you to tell me what to do. I'm glad you're willing to listen to me whine, but I'm the one who's got to figure this out." Cindy squeezed Monica's hand for a moment, a gesture of appreciation, then let go. "Hey, is that Anna?"

Monica looked where Cindy was pointing and saw her roommate coming out of one of the school buildings. She waved to catch her eye, and Anna headed over to meet her friends.

"Hey there ladies," the young-looking beauty said cheerfully as she approached. "Last class of the day is over, it's time to cut loose!"

Cindy smiled at Anna. Her bubbly good mood was contagious, and she felt better already, pushing thoughts of Frank out of her mind for now.

"Now that's what I like to hear," Monica said, picking up her backpack. "What's the plan for tonight, anyway?"

"We -- and that includes you too, Cindy -- are meeting Jake at Fat Teddy's in an hour. After that..."

"After that, who knows!" Monica laughed, raising her eyebrows suggestively.

Anna just giggled, and Cindy had to laugh too, though she suspected there was more to their joking around than she understood. They couldn't know about her being with Jake, could they? The idea startled her, but she quickly decided that Jake would never have told anyone about that night, least of all two of Josie's best friends. Still, she wondered what the inside joke entailed.

"Are you guys gonna get something to eat first?" Cindy asked.

"We could," Anna suggested. "What sounds good to you?"

"Well, there's always The 'Nickel," she offered. "I've always liked their salads."

"That sounds perfect," Monica said, standing up. "I'm starving."


Jake had felt his orgasm approaching and didn't hold back, fucking Gretchen with fierce, deep thrusts into her tight little snatch, stretching her beyond anything she'd ever experienced and setting off another wave of spasms in her sexy little body, when he suddenly remembered meeting her.

She'd had long hair back then, nearly down to her waist, and she'd only dressed in bulky, asexual clothing, mostly shapeless flannels and sweatshirts She'd been incredibly shy, at least around Jake. He'd sat in front of her in freshman English, just like she'd said, but he hadn't given her much thought at the time. She was a nice enough kid, he remembered, but she was quiet and awkward around him. Her face was usually mostly covered by her hair, but even then he'd thought she was kinda cute.

The sexy coed bouncing around on his prick now certainly had a different look, but Jake knew she was the same girl. Like so many students, she must have gone through some major changes when she came to college. Jake would have never recognized this wanton, aggressive sorority chick as the soft-spoken, timorous young girl he'd met a year ago.

The shot into her again and again, surprised at the amount of spunk he was able to produce even after his long night with Josie and Anna, but that was the beauty of fucking several different chicks, he figured: variety is the spice of life.

When he finally finished cumming he pushed deeply into her quivering, dripping pussy, loving the feel of her tight inner grip around his thick shaft, and he watched her heaving chest as she struggled to catch her breath.

Gretchen had felt Jake cumming inside of her and incredibly had found herself reaching a new level of orgasmic release, and now she was gasping for air, her body rag-doll limp on the large plastic crates in the alley. Her body still tingled with energy, orgasmic tremors continuing to ripple through her. She looked up to see Jake smiling down at her, and she smiled back at him, licking her lips as she panted open-mouthed.

"Jesus, Gretchen," Jake said softly, bending down to press his lips to hers. She lapped at him with her tongue, still panting, and Jake cupped her perky little tits in his hands.

"Jake, oh Jake," she moaned, wanting to wrap her legs around him once more but momentarily unable to move. "Oh Jake, oh my god..."

Jake pulled back to let her catch her breath, continuing caress her wonderful little globes. It was hard to believe that this sexy little hard-body had been hidden underneath all those baggy clothes back then in freshman English, but he'd never had a good look at her, of course. He moved slightly inside of her; she cooed and let out a small, breathless groan of pleasure.

As much as he wanted to keep fucking this sexy little tart Jake was all too aware that they were in a public alley behind Fat Teddy's, in plain daylight, and that the bars were filling up with more and more students with each passing minute.

"Gretchen, babe," he said, stroking her cheek. "We can't stay here."

Gretchen rolled her head to the side, sucking Jake's thumb into her mouth and suckling it like a baby.

"Mmm, I know," she purred, "but I don't want to move an inch."

He felt her inner muscles rippling around his shaft, squeezing him even tighter.

"Neither do I, honey, but we have to," Jake insisted. He reluctantly pulled out of her sweet snatch.

His cock slide out in one long, exquisite motion, and Gretchen let out a tired sigh. She could feel her inner walls collapsing back to normal as his cock made it's exit, leaving her feeling incredibly empty. She was aware of the copious amount of fluid swishing around deep inside of her, as well as all over her crotch and inner thighs, but her blissful state of contentment was too strong to let her care much.

Jake's cock was glistening, and he knew he'd want to take a shower before he came back out tonight, but for now he just tucked it back into his shorts and buttoned up as best he could. Then he pulled out some bar napkins he'd picked up earlier.

"Sorry, Gretchen, this is the best I have right now."

She felt him carefully wiping up her thighs, and Gretchen finally managed to push herself up to her elbows.

"Thanks, that's okay," she told him, suddenly feeling a little self conscious about Jake cleaning up her dripping crotch. "Here, I'll..."

Jake ignored her, gently wiping around her puffy mound, then gingerly dabbing her wet lips. He figured she might be pretty sore after all that, but he felt a little bad about making such a mess. Gretchen gave in and let him finish, pleased that he was being so nice to her. He gave her aromatic mound a light kiss when he'd completed his task, savoring her pungent musk.

"I'll have to go to the ladies room anyway, but thanks, Jake," she said softly, reaching for her jeans.

She did feel tender, and she'd probably feel pretty sensitive for a long time, but it had been more than worth it. Jake moved her panties back into position, already soaked through with her juice, then helped her slip back into her tight hip-huggers. Then he caressed her breasts once more, kissing each before pulling her bra back into place and carefully snapping the clasp. He reached over and picked up her shirt, holding it up for her. She smiled and pushed her arms through it as Jake guided it back into place, straightening it out as she pulled it down.

"Good as new," Jake said, grinning.

"Better than new," Gretchen said, sliding her arms around his neck. "So much better after that."

She pressed her lips to his and Jake kissed her back, enjoying her soft mouth, her tiny tongue, and she moved her body against his. After a few moments, though, he pulled back.

"Gretchen, mmmm, Gretchen, we need to talk, honey."

Gretchen looked into Jake's eyes, licking her lips but not saying anything.

"This was wonderful, it really was," he began, "but you have to understand, I have a girlfriend."

Gretchen nodded, a trace of a grin on her face.

"So I can't, you understand, well," Jake stumbled over the words. This is the hard part, he told himself, but he had to make sure Gretchen understood. "This was great, don't get me wrong, but I don't want you to think..."

"You mean we're not getting married?" Gretchen asked, her eyes widening as her face took on an expression of innocent surprise. If she hadn't started giggling so soon, Jake would have thought she was serious.

"Okay, okay," Jake said, "I'm just making sure, is all."

Gretchen rubbed her body against Jake's, first rotating her firm breasts across his chest, then grinding her crotch into his as she kissed him deeply once more. She keep her lips close to his as she spoke a moment later.

"Jake, you've got a new girlfriend, you just don't know it yet," she whispered breathlessly into his mouth. "But don't worry, I can wait until you come to your senses."

Jake ran his hands down Gretchen's slender posterior, cupping her round little ass with both hands.

"Gretchen, I'm serious. I don't want you to think I'm going to leave my girlfriend for you just because we've had sex."

"Mmmm, I waited while you were seeing Mandy," Gretchen whispered, "I can wait until you get tired of this one too."

Jake pulled back to look her in the eye, and she grinned at him. This girl was definitely different than the mousy, shy thing he remembered.

"My, you've changed quite a bit since freshman English, haven't you?" he said with a smirk.

Gretchen grinned back at him, cocking her head slightly, looking as sexy as ever to Jake.

"I had to do something to get your attention, didn't I? I've seen you on campus, Jake. You're always surrounded by hotties. I had to do something to steal your attention. I never would have stood a chance with you otherwise."

"I wouldn't be so sure. You were never unattractive, Gretchen, but you were hard to talk to. You were always so withdrawn and shy."

Gretchen bit her lower lip, considering that.

"Yeah, that's true, I'll admit. I could barely say two words to you before; now look at me. I decided to pledge the end of that semester, but it wasn't until one of my house sisters took my under her wing that I really came out of my shell."

"Well, I can't say I'm complaining," Jake said, laughing. He looked at her for a moment. "But still, you know, this sort of thing..."

"Are you going to lecture me now?" She had a coy, challenging look on her face, clearly enjoying their exchange. "You're the one who just fucked a stranger! At least I knew who you were."

"Whoa, alright already," Jake laughed, and Gretchen giggled with him, hugging him tightly. "I'm just saying, I liked the old you too. You know, I was pretty curious about you back then. But you know how it is, you run into a lot of people in college, and the ones that are the most outgoing are the ones you remember sometimes."

"Yeah, I don't remember Mandy being very outgoing with anyone but you," Gretchen teased.

"Did you know her very well?" Jake asked, curious.

"Naw, just from that class. I'd see her on campus now and then and we'd say hello, but that was about it." She shrugged, running her fingers through his hair. "And once I got into the house, well, you can guess how Greek life is. There's not much time for meeting too many kids outside of the system, at least at this college."

"I guess that's part of why that stuff never interested me. Southville's got so much stuff going on, why would you want to limit yourself to just Frat stuff?"

"Oh, it's not as bad as people try to make it seem. I like living in the house, I love my sisters, and I've met a ton of great people, way more than I would have ever met otherwise, I'm sure."

Jake nodded, considering that. He patted her ass one more time, then gently took her arms from around his neck, holding her hands. Gretchen recognized that he was bringing their encounter to an end, but she was okay with that. Still, she didn't want to let him get away just yet.

"So, do you want to go somewhere? We don't have to go to that party; we could go for a drink, or just for a walk or something."

Jake smiled. Gretchen looked at him with such hopeful eyes. She really was an adorable little girl. He stroked her check once more, then ran a finger tip across her full lips. She puckered them, kissing his finger lightly.

"I really can't, Gretch," he said. "I've got some folks waiting for me, and I'm meeting some other friends later on. And besides..."

"Besides," Gretchen finished for him, "you can't really be seen with me around here anyway."

"I wasn't going to say that," he insisted, but he wasn't very convincing.

Gretchen sighed.

"It's okay," she told him. "Really, I understand." She tilted her head at him, looking at him with puppy-dog eyes. "But at least take my phone number, and give me a call sometime, okay?"

"Of course, baby. Of course."


Ally came back into the family room with a handful of sodas and a couple bags of chips. Amy and Fiona were on the sofa, their feet up on the square glass coffee table, flipping through channels on the Tortelli's television.

"We should get some porn off pay-per-view," Fiona said as Ally handed her a can of pop. "There's nothing on to watch."

Amy laughed at the idea, but Ally just rolled her eyes.

"Yeah, right, and who gets to explain it when it shows up on the bill?"

Fiona just shrugged her shoulders, giggling as she winked at Amy.

"Have you guys watched porn before?" Amy asked, tearing open a bag of Dorito's and shoving a few into her mouth. She was hungry but no one had bothered to fix anything for dinner yet.

"Sure, sure," Fiona told her. "Remember that time we stayed over at Ashley's and her parents had ordered that movie -- what was it -- Bright Lights, Big Titties?"

Amy nearly spit out her mouthful of chips, which made Ally laugh as well. Fiona was having fun.

"Yeah, that's the one I'm thinking of. Or was it Shaving Ryan's Privates?"

"No, no," Ally said, "it was Inspect Her Gadget."

Fiona grinned. Amy couldn't stop laughing. She was shocked to hear her sister and Fiona using such language, but that only made it funnier.

"Or was it Good Will Humping?" Ally asked.

"My Best Friend's Wetting!" Fiona exclaimed, pleased to see Amy laughing so hard.

"Caddysnatch!" Ally squealed.

"Porn on the 4th of July!" Fiona countered.

"Oh god, stop!" Amy said, gasping for air.

Ally smiled at Fiona, who winked at her with a pleased grin on her face. Amy was doubled over, struggling to stop her laughing fit. Fiona took the bag of chips out of her hands, nonchalantly taking one out and munching on it. Ally calmly took a seat in the recliner next to the sofa. It was Dad's usual place to watch TV, and she liked sitting there when he wasn't home. She held up her hand, and Fiona tossed her the remote.

Amy took a minute to catch her breath, then regained her composure. She opened her mouth to say something, but Ally cut her off.

"What's Eating Gilbert Grape?"

Amy started giggling again, thought not as uncontrollably this time.

"Stop it," she told her older sister. After a moment she turned to Fiona and asked, "Is that true? You guys watched a porn that Ashley's parents ordered?"

"Well," Fiona said, settling back into the couch with the bag of chips on her lap, "we can only assume. I'm certainly not gonna ask Ashley's dad if he ordered a porn on pay-per-view. But who else could it have been?"

"Ashley says they do that all the time," Ally said matter-of-factly. "It's kinda creepy, I guess, but I don't know. I mean, at least they're watching them together, right?"

"You're assuming Ashley's mom even knows about them," Fiona said, tossing her head back to shake her long blond hair out. "It could just be that poppa's got a brand new bag, if you know what I mean."

Ally dismissed her with a shrug, continuing to flip through channels on cable.

"Ashely says she can hear them in their room watching that stuff all the time," Ally stated. "Maybe her dad gets it on his own, too, but either way he's definitely watching it with her mom."

"Wow." Amy sat back, grabbing a handful of chips from the bag in Fiona's lap. "I guess I just figured married folks, well, you know." She thought for a minute, then turned to Ally. "You don't think Mom and Dad..."

"No way," Ally answered reflexively, not turning from the television.

Fiona raised her eyebrows and looked at Amy, then at Ally. Ally looked over at Amy and Fiona staring at her.

"What? I don't know, I guess it's possible, but come on, do you really think so? Can you picture Mom watching porno with Dad? I don't think so."

Fiona had a big grin on her face.

"If they ordered it in the last 24 hours, it'll still show up on your digital cable," she said, tilting her head at Ally.

Ally looked up at the ceiling for a minute, rolling her eyes at the absurdity of it. Then she turned to Amy, tossing her the remote control.

"You know how to check it, right?" Amy nodded, pointing the remote towards the wide-screen TV. "Well, happy hunting. I'm gonna go change into some sweats."

Ally got up out of the recliner and crossed the room, shaking her head. At the last minute, as she was about to leave the room, she turned and called back, "But if you find anything, wait for me!"

Fiona laughed, and Amy chuckled too, but she held the remote without knowing what to do.

"Here," Fiona said, holding out her hand. "I'll show how to see what, if anything, has been ordered."


Jake walked into an empty house, feeling a little guilty about fucking Gretchen. Not that he regretted it per se, it was just that he felt like such a cad. Josie was barely out of town before he had his prick stuffed in some trixie's snatch. Even though it'd been fun, he knew it was wrong.

In some way, he also felt like he'd cheated on Anna, too. It was just last night that he was fucking her sexy little twat, telling her how much he loved her and all that, and here he was hooking up with sorority sluts when he could be making sweet love to his adorable, sexy little Anna. What was wrong with him?

His cock was still swollen, remembering how tight Gretchen's pussy had been. He wanted to fuck her again, he knew. How did he get himself into these situations?

He bounded up the steps, pulling his t-shirt off as he went, and headed for the master bathroom to take a quick shower. He didn't waste any time, quickly soaping up and rinsing off his muscular frame (paying special attention to his cock and balls). He stroked himself a few times, remembering Gretchen's orgasmic spasms, but then focused his attentions towards getting on with the night. He still had to meet Anna and Monica after he bought the little high school chicks their booze.

He threw on a comfortable pair of shorts and a rugby shirt, roughly rugging his hair dry with a towel as he walked out onto the upper deck off his bedroom. This was the smallest of the decks, just a balcony really, that overlooked the others. He saw the lights on down at the Tortelli's house, and decided on a whim to just walk down there to get the girls, rather than calling them on his cell. He slipped on a pair of shoes and went back downstairs, making his way down to the back door on the lower deck.


"Oh my god," Fiona said, unable to suppress a chuckle, "look at this."

Amy had watched as Fiona navigated through the on-screen menus for their digital cable service. She'd always known this stuff was there, but never bothered to really pay much attention to it. The way the system worked, if you purchased a pay-per-view movie, you usually had it in your "queue" for a period of time, 24 hours at a minimum, so you could watch it again. This was convenient, of course, but the other side of the coin was that there wasn't any way to remove something you'd ordered until it expired.

Fiona brought up their queue and sure enough, one movie was still available for viewing.

"Oh, we are so watching that later on tonight!" Fiona declared, smiling at Amy.

Amy didn't want to admit it, but she was quite curious to see real porn. She'd sometimes watched a little of the soft-core stuff that was on the movie channels late night, but none of it was even mildly interesting to her, mainly because the b-grade actors and actresses in those awful movies were obviously not really having sex; the positions the were in just didn't allow for actual penetration. They didn't even show anyone's genitalia. It wasn't like Amy was a perv or anything, but she was curious to see what it looked like when a man's penis was in a woman's vagina.

"Watching what?" Ally asked, coming back into the room dressed in a pair of light jammy-pants and a short t-shirt.

"Porn! Check it out, your parents watched 'Wild Nurses' last night."

Ally's eyes opened wide as she realized Fiona wasn't kidding. There it was on the screen, an adult pay-per-view movie. The screen said it was available for viewing for another 12 hours, so it probably was ordered up late last night. She looked over at Amy, who looked excited by the prospect. Ally wondered if she'd ever seen any porn before. Surely she could find it on the internet if she was interested, she figured. Still...

"You interested in watching that, Amy?" she asked her little sister.

"Um, sure, if you guys are," she answered uncertainly.

Ally smiled, then shrugged.

"What the heck, why not? But let's get something to eat first, I'm starving."

"Good idea, let's order a pizza," Fiona said, getting up. "I don't mind going for pick up at Pizza Deluxe if you call it in."

"Deal," Amy said, reaching for the cordless phone.

Amy got up to step into the kitchen to call, and Ally plopped back down in the recliner.

"You don't mind, do you? About the movie?" Fiona asked her friend. She wondered if Ally thought watching a porn with her little sister was a bad idea.

"Naw, it'll be a hoot. Amy's a big girl, she can handle it."

"Cool. Hey, I'm gonna call Ashley and see if she's babysitting yet. Maybe we could swing by the Davis' later and pay her a visit."

Ally shrugged, giving Fiona a "maybe" look. Then she got up to go into the kitchen with Amy to check on the pizza order.

Amy was just hanging up when she came in.

"It'll be $18. I got some cokes and breadsticks too, hope that's okay."

"Sure, that's perfect," Ally told her. She gave her sister a look. "Amy, you know, we don't have to watch that movie if you don't want to, it's no big deal."

Amy tried to read her sister's face, wondering if she was trying to tell her something. The truth was, she really wanted to see what it looked like.

"Well, actually I'm kinda curious about it," she admitted. "I mean, I've never really seen any real porn, you know? I don't know if I'll want to watch the whole thing, but I want to check out at least a little, you know?"

Ally nodded, putting an arm around her little sister.

"Sure, sure. I'm a little curious too. The only porn I've seen has been pretty stupid stuff though, I've gotta say. I mean, there's the initial shock of seeing naked people doing crazy stuff, but then it becomes kinda dull, you know? Anyway, I'm just making sure you're not doing something just cause you think we want you to. I know Fiona wouldn't mind if you didn't want to watch it. And if you get uncomfortable or grossed out or anything, just say so, okay?"

"Okay, I will. Thanks, Ally." She hesitated. In the next room they could hear Fiona talking on her cell phone with Ashley. Amy wanted to ask Ally about sex, about what it felt like and how much it hurt and was there a right and wrong way to do it, but she couldn't think of any question that didn't sound hopelessly naive. She decided not to say anything.

"I think I'm gonna go with Fiona to get the pizza," Ally told her, unaware of Amy's inner questions. "Did you wanna come with or stick around here?"

"I guess I'll just stay here. I wanna change clothes too, maybe jump in the pool for a little bit."

"Cool. We might swing by the video store too, but we won't be long."

The two sisters came back into the family room as Fiona was standing up, flipping her phone shut.

"She's on her way there," Fiona told them, referring to Ashley. "But it doesn't sound like we'll get to see her later."

"Oh well, there's always tomorrow night," Ally said. "Amy's gonna hold down the fort while we get the grub. You ready to go?"

"You bet." Fiona turned to wag a finger at Amy. "Don't you go watching all that porn without me," she joked, causing Amy to blush slightly.


Josie's plane landed in darkness, the time change working against her already late arrival. She'd tried to get some sleep on the long flight, but it had only been a few hours, and she wasn't tired then. Now, stepping into the hot Caribbean humidity, she felt her energy draining immediately away.

"Darling, I know you're exhausted," Nancy was saying, walking with her across the tarmac. "We just have a few quick meets and then we're off to the hotel, I promise."

Josie sighed. "A few quick meets" was Nancy-speak for at least an hour of glad-handling, introductions and socializing, all designed to get Josie's face in circulation with the modeling big-whigs. It was part of the job, she knew, but right now she wasn't feeling up to it. Still, she bucked up and put on the best smile she could.

"Thanks, honey, I appreciate it," Nancy said sincerely. "Really, I do. You're going to have fun down here, I promise. You'll see."

Josie had already met another model, Amber, on the plane. Amber was taller than Josie and a little more voluptuous, with long, silky soft brown hair that curled around her shoulders seductively. She exuded a detached ambivalence about her surroundings that would have come off as arrogant except for her obvious, kind-hearted nature. She was working on the same shoot, and she and Josie had hit it off fairly well. Nancy fell into shop-talk with Amber's agent as the four women got into the limo waiting for them at the airport. None of them had checked any luggage, as all of the weekend's wardrobe was waiting for them at the hotel, so they were able to get on their way quickly.

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