A Day of Pain

Anal

A Day of Pain22 year old Spalding Tyll walked home disconsolately, his knapsack hanging off his arm.It had now been 103 days since Mother had allowed him to masturbate, and it was hanging heavy on his young balls.Mother was mad at Spalding…She was going to punish him through humiliation by making him jerk off in front of the hottest cheerleader at Buttermilk Falls High! Or, if he didn’t want to do this, he could just be celibate until he changed his mind. And he was so horny!Spal looked down at his Iphone as he walked. Shit, he needed to write his oldest brother Potter back. Pots was an Air Force captain, and he’d sent Spalding a big e-mail.”I know it’s hard having Mom crack down on you like this.” Pots had written. “It’s really hard for me…Shit, I’m a decade older than you, and I have to be here in Afghanistan on the Honor System. I have to ice my balls down six times a day to stay straight.Also, Mother shipped me a two foot whittled lilac branch, about an inch thick, and told me to find someone to use it on me. Fortunately, one of my enlisted men—Yeah, I wish it was a girl, too—has taken over my discipline, and pulls down my cammies once every couple of days and thrashes me ’til I cry, and that takes my mind off the horniness bullshit…He was amazed when I told him to thrash me, a commanding officer… but he liked the blowjob afterwards… and I also service Maripat, our supply sergeant with my tongue.But it’s tough. But listen to Mom. She knows best.”And Spal’s other two brothers, Boswell and Searcy had agreed with Pots. They’d taken him out to lunch just last week after they’d all played a round of golf.Boswell, an insurance agent was especially urgent to Spalding to toe the line.”My wife makes me jerk off in front of all kinds of people, Spal.” Boz had said quite seriously.”Rosalyn doesn’t even let me cum more than every few months, but she makes me play with my penis in little rituals, usually in front of either her male or female lovers, or once in front of a visiting Jehovah’s Witness.It cuts down on my big ego, which is always dragging me into trouble, you know with drinking contests.Yes, and stupid shit like speeding tickets because I think I’m the king of the road. Supervised masturbation keeps me humble.”Searcy, a Princeton graduate agreed. “Dude, you just have to let go of all that bondage to self stuff.” (Searcy was a philosopher)”Sure, when I was a junior in college I told Mom I wanted to give up my chastity belt, and I expected she’d give me a lot of shit about it, but she just took it off without a word…Stopped disciplining me, too.But within six months I was snorting heroin, slapping my girlfriend when we got into fights, jerking off in bathrooms to Playboy magazine…Damn I was grateful when Mother gave me another chance and locked me back up.””B-but I don’t want to jerk off in front of this cheerleader. I have a big crush on her, and it’s really going to be awful, I think” Spal had told his older brothers. “Don’t you think there should be another way?”Searcy laughed, Boz joining him. “Man, I don’t know about you, but I am happy that Mom is still controlling my orgasms. I’m really afraid of what’s going to happen when I graduate and move away and get a job, and have to find a woman to run things.I’m afraid things are going to get really fucked up!”And of course Spalding had had to agree, his brothers had a point!At school, the girls pranced past him; many of them were his good friends and gave him friendly hugs, which made Spal just crazy with lust.He wasn’t grounded, after all, and he’d actually been on a few dates where there had been lots of necking in Dad’s 2005 Acura…When Jennifer had wanted to go further, Spal had of course had to demur.Shit, he couldn’t remove his pants, right?He couldn’t let the young people of Buttermilk Falls know that he was in a chastity belt.Jennifer was a hottie, but she was also a powerful gossip, and that would ruin whatever “rep” Spal had, and all his luster he’d gathered from being a point guard on the basketball team.And for playing bass guitar in his band “The a****l Keepers”, from being tall and handsome, all that shit would be irrelevant!But Mom was adamant.She wasn’t going to let Spalding masturbate unless he did it in front of Whitney Ponds, the hot cheerleader that Spal had all those pictures of…The girl he would NEVER have a chance in hell of going out with…but he’d always lusted after.And all this because Spal had had the nerve to try and break into his chastity belt with a bobby pin, because he was so desperate to masturbate.It wasn’t like he had a chance in hell—the damn belt was really secure, Haramidere Escort but Mom was so insulted that Spal would even try…”I am so disappointed in you, Spalding” she’d said grimly.Mother had made Spal strip naked and she’d bound him over a hassock and whipped his buttocks with her wooden spoon.Yes, and then the lead tipped flogger that she used on Dad.Spal’s sister Maisie had watched with amused contempt.Then, when Mother’s arm had gotten tired, Maisie had taken over and used the flogger until Spal had been weeping bitter tears.Maisie was a beautiful girl—she had rich russet curls and full breasts under her snug pink cashmere sweater…But Maisie was a bitch on wheels, and many times Spal had had to bribe her with his allowance and the money he made mowing lawns to keep her from telling the people at college about the way their family “operated”.Maisie was his younger sister, but she had a later bedtime and no curfew…And he’d never seen HER naked, but he was routinely stripped for discipline and punishment, had been his whole life, and she’d seen it all!She’d seen it when Mother dressed Spal in a pink dress and high heels and made him parade with a parasol in front of the house.This after she’d found his computer porn.Oh and she’d seen it w hen Mother had used a strap-on dildo on Spal, to cure him of “attitude problems”.And Maisie had found it hilarious that Spal was so horny. After 103 days of not getting to jerk his dick—nearly four months! Masie was always tantalizing him by walking around in tiny little tops and short-shorts.Sometimes she’d climb on his lap and kiss his neck when he was trying to do homework or program his mp3 player.It was absolute hell.And Spal knew that he would only get a brief jack-off period, even if he did agree to humiliate himself in front of Whitney, it would only be a brief spurt.Yes, and then Mother would probably go back to the old rule—That Spal could next jack off when he got his quarterly report card, and showed up at least a B average!This had spurred Spal to take summer courses—While his friends were surfing and getting drunk on Buttermilk Beach, Spal was in class—Just so he could jerk off in September, instead of waiting for the November report card!One of Spal’s buddies, Nick had pointed out that Spal now had more than enough credits to graduate early, and get away from his strict family, But the truth was, Spalding loved his Mom, and loved Maisie as well. Spalding was planning actually to attend Buttermilk State Law School after college graduation, and continue to live at home.”You don’t have to, dear” Mother had told Spalding. “I’ll give you your keys if you really want to go off to college, but I’m going to supervise you as long as you live here at home.”She had been pleased when Spal had told her that he really wanted to live with her…He had been locked up in chastity since seventh grade, and didn’t know what he’d do if he had unlimited orgasms!One orgasm every academic quarter, usually jerking off in front of the laughing Maisie (who did give him occasional tit-flashes) and Mother…He’d actually probably not jerked off more than twelve times in the last three years!And now of course with Mother’s restriction because Spal had tried to break into his chastity belt, it had been even longer. She’d just ignored his latest report card, which had been very good, and told him,”You lost your chance to onanize dear, when you violated my trust by attempting to break into your belt. You can only masturbate now if you do it in front of the Ponds girl.”And Maisie had thought this was HILARIOUS. She constantly teased poor Spal about it, coming in his room and laughing. “What’s Whitney going to do when she sees what a pathetic little perv you are, Spal? She’s going to tell the whole school about it…You’ll be in the Friend Zone, if that, for every girl at Buttermilk Falls High!”Maisie was so cruel too—Just last night she’d sneaked into Spal’s room wearing only a little T-shirt, no bra, and panties. She’d ordered Spal to take off his clothes, and she’d tied his hands to the bedposts.Then she’d taken the chastity belt key, which she’d filched from Mother’s key ring.Maisie had unlocked Spal’s belt and played with his penis.Then running her long purple nails up and down his stiff dick for an hour and a half.This wasn’t Maisie’s first visit—She’d done this a number of times…Mother probably knew about it, and didn’t mind, because after all, Maisie didn’t let Spalding cum! She just teased him, and sat on his broad chest.Maisie would then would pull back and rub her little crotch up and down over Haramidere Escort Bayan Spal’s stiff, suffering cock…He was so young, and so full of semen, and SHE KNEW IT!”It must be hard…get it?” Maisie had said as she rubbed her little panty covered crotch against Spal’s throbbing erection.”I know you just want to fuck me, your little sister, and isn’t that forbidden…forbidden by the Church?”Maisie was a Virtue Girl, in the choir at the Buttermilk Falls Salvation Temple…they had a virginity mission!Then Maisie had lay down next to Spal and just casually rubbed his hard penis and whispered in his ear.”What a hard life it’s been for you, Spal—I’ve watched while Mother gave you cold showers, and punished you by tying a pink ribbon to your dick and made you walk around with a book on your head so you’d learn to be a lady…Just so you’d give up your testosterone driven passion…But does it work, no…””Please, Maisie, can’t you just let me jerk off? Mom will never know.” Spal had pleaded with her.But his little sister had just laughed in his face.Laughing as she’d continued to stroke his desperately bloated penis.”How much would you give me, Spal?” Maisie asked, as one of her adorable russet curls fell over her shoulder.Spal looked at her nipples coming through the tight Hannah Montana T-shirt she was using as a nightie.Spalding rolled his eyes. “I’ll give you twenty-five bucks, okay? I don’t have a lot, but I’ve been working part time at the Quik-Mart, saving for a new electric guitar…I can give you twenty-five, I think.”Maisie had laughed. “No no…that’s not enough. And you have more money than that. Uncle Howard gave you your Christmas money late.You want to cum, you’d better give me more money.”So finally Spal had confessed that he had about one hundred fifty dollars hidden in his sock drawer.Maisie had taken it and tucked it in her panties…And then she’d called down the hall, “Mother, Spalding is trying to bribe me to let him cum!He got me to take off his chastity belt and I feel so guilty!”Maisie had given Spalding a wicked smile.Mother had come into the room, and taken a wire coat hanger out of Spalding’s closet. “You just can’t keep your filthy mind off your penis’s satisfaction can you?” Mother had asked, with gritted teeth.SMACK! TWACK! WHACK!The coat hanger had come down quite painfully on Spal’s thick cock until it was bleeding and tiny. Then Mother had spun Spal over and whipped his ass with her trusty lead-tipped flogger until he was sobbing in his pillow.Mother and Maisie had derided Spal for being a “crybaby” before he’d been locked back up again…Spalding was still covered with welts the next day…Dad was in trouble for something else, and that morning the two of them had been forced to eat out of dog dishes.Yes, crouching naked while the rest of the family, fully clothed, had sat at the table.Spalding knew that Maisie would never give back the one hundred fifty dollars.Yes and if he pestered her for the money, she’d probably do something even more extreme. Once Maisie had brought her bisexual boyfriend home and, with Mother’s agreement, had forced both Dad and Spalding to suck the guy’s dick…Mother had said it would be a “learning experience” for them!Spalding had never forgotten what it was like to have another man’s semen in his mouth, and being forced to swallow. Dad, who had sucked countless dicks of Mother’s assorted lovers over the past twenty years had insisted that Spal would get used to it…But who knew?Now Spalding crossed the street to his house.He saw Darrell Plunkett posting a letter in the mailbox. He recognized Mr. Plunkett from his ChasteBois support group and indeed, he’d mowed the guy’s lawn.”Hey Mr. Plunkett, how’s it going?” Spalding asked in a friendly voice. Darrell looked up and grinned.”How’s it going, Spalding?You missed the last Chastebois meeting.” Darrell lowered his voice when he said this, although the streets in their suburban neighborhood were deserted.”Yeah, we had an away game, and didn’t get back on the bus until seven Sunday night.Hey, it’s none of my business, but how did it go with your secretary?”Spalding was a little afraid to ask this out in the public, but he had to know, as he had a relevant problem.”I ended up doing as I was told!” Darrell said, smiling. “I really feel better now, and I have a new friendship with my secretary. She has keys to my belt, and we sometimes have a few sessions over lunch hour. Matter of fact, Thelma is currently indoctrinating her own boyfriend in our little lifestyle.”Spalding sighed. “I’m still holding out, but I don’t know how Escort Haramidere much longer I can. I think I’d die if Whitney Ponds, the cheerleader found out that I was a naked slave boy at home…But you know, I love my mom and I know she knows what’s best for me, and I’m like, dying to pound my pud, Mr. Plunkett.”Darrell smiled.”I know. It’s hard to do the right thing, Spalding. But remember, your parents love you and know what’s best. And you love them…I remember you telling the group that you’re going to stay here to go to school because you realize that your mother’s chastity training and her physical discipline is good for you.And that’s important. You’re a very mature young man.””So are you saying I SHOULD masturbate in front of Whitney?” Spal said, confused. “I don’t get what you think I should do.”Darrell smiled as he turned away. “You’re a smart k**, Spalding. I can’t tell you what you should do. I know that the decision I made to expose my submissive status to my work inferior did me a lot of good as a slave male.I love my wife and I’ll do anything she asks of me. I hope you can make the decision on your own.”Then Darrell stopped and smiled. “But you are 22 years old, Spalding.If you like, I’ll take you down to Buttermilk Falls Hardware and we’ll buy a bolt cutter and cut the belt off. I’m sure your parents would understand if you want a different life.If you’re afraid of your mother’s retribution, I’ll even help you get an apartment and you can screw girls night and day.Really, but is that really what you want?”Spalding looked terrified.”No no…I begged my parents for this when I turned nineteen, they’d always been permissive…But I knew about their activities!Although I get tempted, I’d never want to rebel to that extent. My folks, except around chastity and discipline are really great people. I know Mother has my best interests at heart. I think I’d better just do what she wants.”Darrell Plunkett grinned as he watched the boy walk off.That’s a k** with a good head on his shoulders!Spalding came to his door, and opened it up. Darrell Plunkett was right. He had to get used to being a slave boy, and adjusting to his slave status.It was what would make him happiest!But when he looked in the living room, he found the decision might have been made for him! There was Whitney Ponds…A waterfall of blonde hair, huge tits, long legs…In her cheerleader uniform, as a matter of fact, though football season was long over.And Dad was kneeling before Whitney, stark naked, slowly rubbing his thick penis. Spal knew that Mom made Dad do this sometimes…Mother wouldn’t let him cum, but she’d have him jerk his dick slowly… It was torment, but saved Mom from having to manually tease him, as she had a touch of arthritis in her left hand.Spal’s sisters, Maisie, Fawn and Tania were on the couch next to Whitney, and they all were laughing their asses off watching Dad.Maisie was the youngest, and of course they all had witnessed the males in the Tyll family and the humiliations….Mother came to Spal and smiled.”Dear, I’m so glad you’re home.Your father has just started, and I suggest you remove your clothes, and Maisie will unlock you and you can join him…Whitney has been waiting patiently.”Whitney looked straight at Spal and said “Yes, that’s right, Spalding. I was raised in a femdom family myself, and I’ve been kind of interested in you.You’re not the best looking guy in the world, but I need a slave boy in my life…Let’s see how submissive you really are…And maybe we can go to the movies on Friday!”Spalding pulled off his sweater excitedly. Things were really looking up!Stripping off his clothes quickly, he stopped in front of Mother, and she unlocked his belt.Then Spal slid into place next to Dad, and began jerking his dick and looking at Whitney with reverence…But then she said…”Actually, Spalding, I’m not just a cheerleader, attractive two-dimensional image of me as you may have…I’m also a drama major, and I just went through this charade to please your sisters and your mom!” All four girls and Mother burst into laughter.”I can’t believe two men would actually take off all their clothes and do this in front of a young woman.And no I didn’t grow up in a female dominated family…I’m leaving now, and I probably will tell this around school, but if you stay the fuck away from me, you little weirdo…I might give you a break on that matter. See you later!”And with that, Whitney flounced out. Spalding began weeping softly, and Dad looked at him with some sympathy…But then they both cringed in pain when Mother rapped their cocks with her lead-tipped flogger.”Sorry boys…you’re getting locked up again. I have changed my mind.You can cum in September, Spalding.Yes if your NEXT report card has all A’s on it, as you’ve shown me you have the ability…And Potter Senior, I think you can hold off until your Christmas bonus!”And that was it for Spalding!

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