My mom tried to pick out nice, modest outfits but the store owner insisted on the sluttier clothing. He told her that it was more her style. These, of course, are the outfits my mom would be getting to buy at half price. Her new wardrobe was coming together quickly.
 After demonstrating the outfits for the fashion show, she then had to wear the outfits around the store, starting with the first and changing into the next one every 20-mins until she's finally walking around the store in lingerie. Women don't make eye-contact with her but they did check out her outfits, examining the tag and wondering if they should buy them. The guys, however, check her out for other reasons. They perve all over her, touching the outfits, closely examining her tits and ass and remarking how they might buy the outfits for their wives. My mom smiles professionally as the perverts get handsy, feeling the fabric and tugging on the tags to better see the price. "Jumbo-sized, eh? Looks great! Can I pose for a picture?"
 "S-sure," my mom answered, her mouth frozen in a big smile.
 The man slung his arm tightly around my mom's bare waist, pulling her hips against his side. My mom did her best to keep smiling as the man reached down and grabbed the tag hanging off her left tit, holding it up for the camera to see: "Jumbo Sized."
 During her next shift at work, her boss praised her modeling at the mall clothing store. He told her she had a real talent for it "now that you have the right tits for the camera," and he offered to set her up with one of his modeling agent buddies. It was the best news my mom had heard all year. She agreed instantly. Her boss continued thrusting his cock between her legs.
 There was a special 'bring your daughter to work day' that week. Since she didn't have any daughters, she thought it might be to take me instead.
 "But, mom... I'm a boy," I protested pathetically.
 "Of course, everyone knows that! But it would be good for you to come to learn a bit about how the business world works!"
 I did want to get a bit of experience and see how the studio was where my mom worked. I agreed. Since Vanessa was interested in joining the news channel world as a weather-girl, it was an invaluable experience for her to join along too. The pair of us went to the studio that evening.
 "Hi everyone, this is my daughter!" My mom said as she presented me with a laugh, enjoying seeing me squirm with humiliation. "It's just a joke," she whispered beneath her chuckles. I sighed as I saw Vanessa giggling with a hand over her mouth.
 My mom led Vanessa around the studio, introducing her to all the executives and directors. They looked her up and down with hungry eyes.
 "So, you want to be a weather girl when you get older? I think you'd make a GREAT addition to our studio," Becky's boss said as he shook Vanessa's hand. Vanessa had an excited, grateful smile on her cute face as she shook the boss's hand.
 "I would LOVE to work here, and maybe follow in BB's footsteps," she gushed excitedly. I kicked my feet at the floor as I stood by the wall, pretty much unnoticed, except for the occasional joke about me being BB's 'daughter.' Vanessa got all the attention, and she loved it. She whispered excitedly to me how great it was to get these inside connections. I reluctantly agreed and supported her.
 My mom's meeting with the 'model casting  agent' the following week went great - for the agent. My mom was eager from the getgo - this was her lifelong dream, she didn't want to squander her chance - and the agent picked up on her desperation. He spoke to her about modeling and slowly pressured her into going past her limit. "You know, there's just not really much interest these days if you're not willing to do tasteful nudity."
 "I guess if it's tasteful, I'd be okay with it," she answered naively.
 A few minutes later she was signing her first contract. She felt pressured by the agent and barely looked over the pages she signed, naively trusting it to be a fair contract. She didn't even read the numerous clauses she had to initiate. She tried to keep a professional manner as she signed document after document. Little did she know she would be under contract for a thing called 'live modeling' where she would basically be working as a camgirl, stripping her clothes and talking dirty to clients as they jerked off to her online.
 And the clauses she initialed? She was under contract to the CamStudio for a year, and she was barely getting paid. It wasn't all webcam stuff, the studio also took pictures of her.
 The photo-shoots always started with her wearing ridiculously skimpy outfits and posing in all sorts of ways. But, as the photoshoot went on, she had to strip more and more until they were taking pictures of her naked while she had to spread her legs, hold one of her large tits in her hands and hold up a peace sign with the other. That pose became her signature shot, included at the end of every photoshoot. 'Tasteful nudity' indeed.
 A month later she was signing a new contract for more money, in return for agreeing to use dildos during the cam sessions. Two months later she signed her first deal for full licensed filming. It included starring in 10 adult videos. A day later she was staring in her first porn video (that she was aware of). A week later she was filming her first live anal scene. Eleven months later she was a well-known pornstar, putting out new explicit videos every few weeks. She did everything: Lesbian scenes, double penetration, blowbangs, rimjobs, and even 'entirely anal, 0% pussy' gangbangs. She was known as 'that pornstar who was too stupid to use a fake name before getting into the business.' Her other known name was 'Butthole Becky.'
 Her most famous video was titled: "Ten guys line up to destroy a dumb-blonde MILF's asshole."
 She still had her job at the news studio, too, but things had been degrading there from bad to worse. The 'secret' arrangement between her and the two cameramen had slowly leaked throughout the studio, and all the guys wanted a turn with the gorgeous up-and-coming blonde starlet. My mom knew she had to do her best to keep the secret contained, but it grew difficult. It was not unusual for her to show up to her office only to find that her appointment calendar had six or seven 'meetings' scheduled with different crew members.
 She tried so hard to maintain her status as a professional as she opened the door to let one guy out of her office, all the crew glancing over as she let another in. She closed the door behind him then took her position on the couch while he began to undo his pants.
 Worst still, every few weeks one of the producers would have her accompany them to a business trip somewhere for a weekend. Mr. Richards would remind her how important it was for both of her careers that she kept the producers happy. Sometimes she never even made it out of the limo from the airport before the producer already had her bent over the seat, skirt pulled up to her hips and cock sliding in and out of her pussy. She basically became a weekend call-girl for the executives at the news studio.
 Meanwhile, back

"If he tells anyone, I could lose my job," the teacher said quietly. She didn't have a concerned look on her face, but more a look of annoyance.
 "He's not going to tell anyone," Brad said as he finished zipping up his pants and began taking off his belt. I wondered why he would take his belt off after he finished making love, and not before.
 "How do you know?" She asked, pulling her skirt up to her waist.
 "Because, if he does, I'll share all those dirty videos he's been making of his mom, and he'd be in a lot more trouble than just getting fired," the bully said with a smirk.
 Mrs. Hunter gave Brad an impressed smile. She enjoyed seeing how confident and securely he handled the situation.
 "You're not gonna tell, are ya, little Milksop?" Brad asked in a mocking, degrading voice.
 "No, sir," I answered, looking down fearfully.
 Mrs. Hunter's eyes shifted towards me, and a look of disgust crossed her face. I looked so weak and pathetic, yielding to Brad's superiority. She then reached over the desk and turned the picture frame down on its face, as if seeing me somehow reminded her of her wimpy husband.
 "Let's prove it so that nice Mrs. Hunter feels less worried," he said as he stepped closer towards me, smacking the belt in his hands like a whip. I gulped.
 The young, charming and very beautiful teacher sat at her desk to watch her lover 'handle the situation.'
 First, Brad had me drop my trousers and show off the humiliating cage covering my dicklette. Brad started spilling all my humiliating secrets (often twisting the stories to make himself seem more generous and myself seem more perverted. He only had to tell a hundredth of the degrading things I'd been through and I was already shaking and swearing I'd never tell anyone. Mrs. Hunter was laughing. The situation was much farther than she thought, and now she had no fears about me spilling the secret about her and Brad.
 He finished it off by having me place my hands against the back of a chair as he stepped behind me with the belt.
 *Wack!* The belt ripped across my bare ass, making me scream. I had to sing out apologies for being a perverted peeping tom as Brad whipped the hell out of me his strong arms and leathery belt. Mrs. Hunter continued laughing, enjoying the show. In her eyes, I was the most despicable, disgusting and perverted wimp she'd ever seen. With each swing of the belt, she laughed with joy, glad that I was getting the punishment I deserved. As I belched out my apologies, I reminded her of her husband - the one who looked at porn and couldn't get hard for her - and she enjoyed seeing me whipped even more.
 Multiple beads of tears ran far down my cheeks as the belt left deep, red welts across my buttocks. When the cruel bully was finished, he walked over to the teacher. "Your laugh makes me want you even more," he said as he stepped towards the cute, smiling teacher. She laughed some more, glancing at him with big warm eyes as she did.
 The bully reached down and fondled her breast. "Ooo, round two already?" She said playfully as she ran a finger under his chin. "But..." Her glance shifted from Brad towards me, sitting there blubbering against the chair. "The annoying wimp is still here," she said scornfully.
 "So? He's not gonna tell anyone. He wants to be a perve and watch!"
 Before Mrs. Hunter could protest, Brad shoved his mouth against hers. She swooned into his arms. A moment later and they traded places - Brad was sitting in her office chair and she straddled him, her skirt hiked up to her waist. I had to sit there and watch as she mounted him and rode him to a second orgasm. "That's my big, strong man," she whispered as she rocked her gorgeous, fit body up and down on the bully. I watched with pain (my pants hurt too much to pull up so they were still down around my ankles.) Brad's hands roamed over the gorgeous teacher's body, squeezing her buttocks and sliding up her curvy hips and thin waist.
 She continued riding him, the sound of her moans and begs for more were punctuated by soft kisses. Brad got his reward for 'dealing' with me fully.
 The teacher I favored, the one I used to find safety and comfort in from my bullies, had now come to completely detest me.
 Brad and the gorgeous teacher continued their affair throughout the rest of the school year. They'd share sexy glances during classes, flirtatious touching and sly winks in the school hallways, and secret kisses in the teacher's lounge or her office. And after school, they'd fuck like rabbits. They couldn't keep their hands off each other. Not once did I see him try to do anal or indecently grab her breasts. It was sensual, respectful and very erotic. Somehow that made it even worse when he came by my house on the weekends, slapping my mom's ass and saying "why don't you jiggle those fat tits for me, Bimbo?" And my mom would always answer with a huge smile, "Okay! Let's go to the bedroom!" Then, of course, he'd make my mom take it up the ass in her bedroom.
 Since Mrs. Hunter knew that I knew about their affair - and knew I was as harmless as a mouse - she'd even let Brad post me up as a look-out boy, having me stand in front of her office door as I listened to them make love. It crushed me.
 Things at work did not turn out so well for my mom. When she returned to work after the slut-off, the schedule on her wall had an appointment with Mr. Richard as well as an appointment with the camera guys. Her boss fucked her pussy in his office while talking about her up-coming modeling gig. He explained that she would be unable to accept money from the 'Jean’s Boutique' clothing store for the modeling. It would be a breach of her contract with the studio. However, they can pay the studio and the studio can 'lease her out' to model for the clothes store. My mom didn't like the sound of being 'leased out.' It made her feel like a prostitute. But, she was getting her boss's dick rammed up her pussy as they spoke, so she could hardly protest.
 To compensate her for modeling, the clothing store had agreed to let her buy any clothes she models for half-off. The studio will buy the clothes and just take the money out of her paycheck. My mom accepts, remarking how she badly needs a new wardrobe that fits her new figure. The boss tells her what a great move this will be for her career as he continues with his primary task: emptying his balls into her pussy. He smiled as he fucked the dumb blonde starlet, thinking about the new source of income he'd be getting by lending her out as a model.
 Straight from her bosses office, into her closet office for the next appointment: Being double-penetrated by two cameramen as they continue to blackmail her. This time, the cameramen boldly take advantage of her ass. She resisted at first, but they ignore her pleas, reminding her of the blackmail video and telling her to take it. She does. One cock in her pussy, one in her ass. They took turns trying out each hole, a video camera stuffed in her face. She'd never felt more used.
 Afterward, she changes into her embarrassingly slutty outfit for the filming. Today is a series of infomercials on... Birth control pills. Just before she walks on set, Frank shoved a remote-controlled vibrator into her cum-filled pussy.

Brad the Bully Seduces my Mom – The Final Chapters

After the slut off, I cleaned the creampie out of Vanessa's ass while Brad and my mom snuggled in the bed.
 Brad explained the arrangement to my mom, how I'm prescribed to eat cum to boost my testosterone, and my mom thought it was a great idea. I can't even begin to explain the humiliation of licking up Brad's creampie out of Vanessa's ass while my mom and Brad both encourage me on.
 At least Vanessa won the slut-off. The one little bit of satisfaction I can take away from this whole humiliating ordeal.
 "Actually..." Brad's words made me freeze.
 "Vanessa's tight ass felt the best, that's for sure. That's why I dumped my load in there. But, when I look over the points from the entire evening, (he was scrolling through his phone as if he were reading a score) it looks like your MOM got the most slut-points."
 My mom let out a fun little celebratory cheer as Brad announced her as the winner. I started to pout, but Vanessa cut me off, telling me not to worry about it and focus on eating out her creampie. I slunk my tongue deeper in her ass, eliciting a warm smile on her face. "That feels soooo nice! He came really deep in there, so you'll have to lick for a while!"
 Of course, the real reason I was pouting was that that it meant another week without a release from my chastity cage.
 From that night on, Brad's behavior around the house got even worse. He no longer had any inhibition. He would reach out and grope my mom in plain view, whenever he wanted. We'd be sitting at the kitchen table, mid-conversation and he'd walk up behind her, reach around and squeeze her tits right in front of me. "Love these nice fat tits," he'd say as he slid his fingers down her top and groped her breasts.
 "Mmm, thank you, babe," she'd answer sweetly, gently rubbing his arm as he grinned his teeth at me and continued fondling her breasts. Anytime he felt like it, he'd spank my mom on the ass or call her his slut. And my mom? She'd answer "Yes, babe?" And get him whatever he wanted, waiting on him hand and foot.
 After the slut-off (and coming to grip with the fact that I wouldn't be getting released from chastity after all. It was so unfair, I did everything I could for it!) Vanessa spent the night at our house. She slept in my bed, but just so we could cuddle. While we were in my bedroom, she spent some time looking in the mirror.
 "Babe... Do you think my tits are small?" She asked softly as she stared at her body in the mirror.
 "What? You're crazy! You have an amazing body!"
 She smiled. "That's sweet, but... I just wonder if breast implants would make me look even better, like your mom..." I cringed as she spoke. The seed had been planted. Brad had said something during the slut-off to make her self-conscious about her tits. Probably comparing them to my mom's. Vanessa continued fondling her breasts in the mirror for a few minutes, a frustrated look on her face before she finally came to bed.
 "That felt so wonderful when you tongued my ass, I can see why Brad likes it," Vanessa said sweetly as she cuddled beside me under the covers. "And you know, my ass is so sore from Brad's pounding earlier tonight... Maybe you'd give it another little tongue-massage before we go to sleep?
 Nothing would have made me happier than to please my sweet girlfriend. She turned around and I slipped under the blankets, planting my tongue in her ass.
 "Uhhh yes, that feels so nice. Keep frenching my ass a while longer. It's so sore. Mmm." 20 minutes later, my tongue still buried in her ass, I heard she was passed out asleep. Looks like I wouldn't be getting any more cuddles after all. Still, I was happy knowing I'd found a way to finally please her.
 After the rain, comes the sun. The next morning was one of the sunniest most beautiful days of the year and my mom and Vanessa both seized it by going to the pool. They spent all morning sunbathing. They gossiped together the entire time, but the only thing I ever heard them gossip about was how great Brad was. Every time I went outside to deliver their drinks or knelt on the ground to massage their feet, they were speaking about how wonderful Brad was, how big his cock was, how strong he looked last night, how fun it was being treated like a toy to such a powerful guy.
 I tried my hardest to zone it out as they gushed and gossiped over my bully.
 During the sunbathing, Vanessa asked my mom if she was happy with her body enhancements (the plastic surgery). My ears perked up, and I glanced up from my post massaging my mom's feet.
 "Oh yes, one-hundred percent!" She answered cheerfully as she ran a finger over her bra. She talked the procedure up, saying how it's given her so much more confidence and all the compliments she's gotten from Sarah, the cheerleaders, her fans, etc. She mentioned how great it's been for her career, how much more likely she is to get promoted now, plus possibly becoming a model soon...
 I don't think my mom realized it but I did. I could see the look in Vanessa's eyes as my mom spoke. It was more than just curiosity, Vanessa was actually considering following in her role-models path. I wished my mom would shut-up about it but she kept going on and on about how great the plastic surgery was. She even added in a sexy whisper and a little wink how much Brad had liked it, too.
 After the morning sunbathing, my mom had to go to the Home Owners Associate (HOA) meeting. It was a meeting where the members from the neighborhood would discuss any local issues, as well as a meet-and-greet for new members of the neighborhood. My mom would be bringing a casserole and going to introduce herself to the new members of the area.
 I didn't know it, but Brad had prepped my mom for it the night before. While I was cuddling with Vanessa, Brad had helped her pick out her outfit. My mom was hoping to recapture her reputation as being a respectable, modest woman and had picked out a lovely but tasteful dress to wear. However, when she showed it to Brad, he objected.
 He told her how important an event like this could be for her career, and she should pick out a dress that shows off her new figure, not hides it.
 "Yes that's true, I hadn't thought of it like that," my mom answered thoughtfully.
 "Something like THIS," Brad said with a mischevious smirk as he held up the dress he found in her closet.
 "Oh, but... I don't even think that would fit with my new breast sizes," my mom answered hesitantly. But Brad insisted. He had her try it on and finally talked her into wearing it. He also pushed for her to brag about her new figure, not hide it. It'd be great publicity for her new career. She should be flirting with the guys (tastefully!) and if anyone asked about her tits, she should proudly boast