Date: Sat, 20 Aug 2022 19:22:56 +0000 From: Jane Smith Subject: Yuppie Gets A Boy I'm intending to write Yuppie stories as an unconnected series that may end up in any section. Ideas and feedback are always welcome. You can contact me at allseeingpigeon@outlook.com. I read all emails, though I may not respond. I'm on Wickr as allseeingpigeon. I may not be in your time zone. Bear that in mind if you don't get a response from me -- if you set your messages to burn too quickly, I won't see them. Please do not send dick pics without asking first. Seriously, my dude, etiquette. This story is fantasy and has no basis in reality. No, really. It's not a double bluff. Nifty is a vast, invaluable resource, so why not make a financial contribution at http://donate.nifty.org/donate.html ? --------------------------------------------------------------------------- London, the booming Eighties. The name's Gavin McCreith. I'm a 32-year-old stockbroker, and I'm just about as rich as Croesus, which allows me to buy whatever the fuck I want. Fast car; penthouse suite. Coke. Little girls. And -- when the mood strikes -- little boys. My lifestyle brings me into contact with other elite earners. We're all pigs, especially the women. Money brings entitlement. It also makes all your problems go away, one way or another. I've been playing with a woman called Margaret for about six months or so now. She's a high-flying marketing consultant in the City, older than me -- early forties, I'd say, though she slaps me every time I ask -- and she doesn't want to fuck me. Her main kink is humiliating her partners. That's a no-go for me; in any sexual encounter, I'm always in control. But we've come to act as each other's wingman. She's beautiful -- 5'9'', massive peroxide hair, slender waist and large breasts. Not massively big, but a good handful. A deep tan and blazing blue eyes. She's a ball-breaker. A real Iron Lady. If you call her anything other than Margaret -- Maggie, Mags -- she'll slap your face. I'm probably a little in love with her, but it's more what she represents. Power. Control. Authority. We both have a thing for kids, for breaking in virgins. As neither of us want rugrats of our own -- too noisy, too messy, too much a cramp on our lifestyles -- we find parents who are willing to whore out their little angels. Will is a client of hers, a balding, overweight bloke in his early 50s. His son Luke is 9 years old. The mother is, apparently, his kids' au pair. When his wife found out, she divorced him and took their children with her. The au pair dumped Luke on him and fucked off back to Sweden. Will has a big house in the country where he holds his own sex parties. He's been grooming his boy for a few months now. He's taught Luke to suck cock, and to be comfortable having a finger up his tight hole. After a considerable amount of negotiation -- which involved serious amounts of cash and half a kilo of coke -- Will sold his son's virginity. While I was forcing my adult-sized cock into Luke's tiny cunt, Margaret had separately negotiated to fuck his father's arse, to humiliate and dominate him. The whole scenario made me shivery. I spent hours jacking off prior to the actual event, fantasising over how good it was going to be. I didn't touch my cock for a week beforehand, wanting to have a good load ready for the little boy I was going to fuck. Finally the night came around. We didn't waste time with pleasantries or social niceties. We drove down to Will's country house in my Merc, then immediately went upstairs to the master bedroom. Will had a huge bed. The covers had already been stripped off and dumped in a corner. I laid out a couple of lines of coke on a side table. From the twitchy way Will was moving, he'd already started on his own stash, but he was happy to take another big snort when I laid it out. Margaret poured herself a large glass of champagne and sat on the edge of the bed, waiting while I broke a Valium in half and gave it to the boy. He glanced at his father. Will nodded. Luke swallowed the pill. The coke hummed in my system as I watched Will and Luke undress. Will's body was about what you would expect from a man of his age; solid, flabby, stomach stretched out. Almost covering his balls and slowly-rising dick, which grew to an average 6 inches. Margaret loved to humiliate men like him. Luke was beautiful little boy. His hair was blonde and messy, his skin as tanned as Margaret's, his eyes a radiant and innocent blue. I was already picturing his face streaked with tears. Breaking in boys required a slightly different approach than girls, but the first time was always going to hurt -- especially on such a young boy, only 9 years old -- however careful you were. And I wanted to hurt him. And Margaret wanted me to hurt him while his helpless father watched. It was the ultimate degradation. Luke's body was sweetly beautiful. Narrow shoulders, slim arms and legs, and the remnants of a little pot belly. His arse was plump and showed the first hints of turning into something every dick would want to find a home in. I already knew I'd want to fuck Luke again and again, even before I'd taken him for the first time. He held his hands over his goods. "You're a very attractive boy," I said to Luke. "Do you know why Margaret and I are here tonight?" He nodded. At his father's nudge, he spoke. "To have sex with us." My 7.5 inch cock was hard and pressing against my trousers, a damp feeling telling me that it was already leaking. "That's right. And do you know how a man has sex with a boy?" Luke's face was red. "He puts his willy up their bum." His voice was barely above a whisper. "Uh huh." I eyed his naked body. "But most men call their willy a cock or a dick. Move your hands out of the way and let me see yours." Flame-faced, he looked at the floor and let his hands drop. His little dicklet was 3, maybe 3.5 inches, his balls tucked neatly behind. His skin was smooth and unblemished. Beautiful. "Touch your cock, Luke," I commanded. "Wrap your hand around it and start stroking. Show me what it looks like hard." Will was looking down at his son's stiffy as it rose quickly in the boy's hand. When I glanced at Margaret, she was looking at Will, eyes narrowed with predatory interest. Luke's tiny erection was as beautiful as the rest of him. I licked my lips. "Well done. Very good." If he was calm -- if he trusted me -- it would make his resultant pain that much sweeter. "Now, grown-ups call sex `fucking'. So now you know I'm here to fuck you, Luke, I'm going to slide my cock up your bum and fuck you." I was getting myself off on filthy talk. Margaret was a whore for it, and I could see from the way Will's cock strained that he appreciated it too. A surprising amount of parents were willing to sell their children's virginities for obscene amounts of cash. "But do you know why Margaret's here?" "She's not here to have se -- I mean, to fuck me?" Luke asked uncertainly, glancing at his dad before looking back to me. Margaret took over, her derisive laugh ringing through the room. "No, baby boy. I'm here to fuck your daddy." I could almost see cogs turning behind his eyes. "But you don't have a cock." She smirked. "I have something better than a cock. Don't worry, kiddo, you'll get to see it soon enough." Will paled. "You're not going to use that on --" "Don't worry." She flicked a condescending look at Will. "The biggest thing going up your son's virgin cunt tonight will be his dick." She tipped her head at me. "What I plan to use on you will be much bigger." Will visibly swallowed. Fuck, this was going to be so hot. Margaret and I began to undress. I shrugged out of my clothes in seconds, tossing them aside, but she liked to take her time. It was part of her plan. She slipped out of her jacket -- the shoulder-pads giving her that hard executive edge -- and pulled the zip down on her skirt. She let it drop, then slowly unbuttoned her blouse. She wore slut-red lace knickers, a half-cup bra, suspenders, and stockings. She could have been a Page 3 centrefold, any man's wet dream. But however fantastic her body looked, I only had eyes for the little boy staring at her with wide-eyed awe. Margaret fluffed up her already fluffed hair, then opened the overnight bag she'd dumped on the side table. She laid out the contents: - a harness, a massive double-ended dildo, a riding crop, a paddle, and a variety of dildos ranging from finger-width to the size of my own cock. Both Luke and Will's eyes widened. Leaving her to do her own thing, I gestured to the boy. Will put his hand between his shoulder blades and gave him a gentle push forward. He stumbled and I caught him, giving him a reassuring smile. "Let's get up on the bed," I suggested. "I'm going to make you feel good, Luke. OK?" "OK," he said hesitantly. Margaret, meanwhile, took the other side of the bed. She picked up the riding crop and settled against the pillows, her fuck-me stiletto'd feet flat against the mattress. She spread her legs and clicked her fingers at Will. He climbed up on the bed. She tapped the top of his head with the crop, making him flinch. "Lick my shoes," she said softly. "Watch what a real man does to your son." Will shuddered and leaned forward, thick pink tongue darting out as he started slathering at her shiny shoes. Margaret slid a hand inside her lacy knickers and started working her clit, eyes fixed on Will. She didn't really give a shit what I was doing -- it was all about Will's reactions to his debasement. I focussed on the little boy kneeling anxiously in front of me. Still smiling reassuringly, I got my finger under his chin and tipped his head up, then slowly leaned forward and kissed him. His small mouth against mine was delicious. He tasted of something sweet and fruity, whatever E-loaded sweets his father had given him prior to our arrival. I sucked his tongue into my mouth. He was pliant, letting me control the kiss, letting me nip at his lips. Grasping the back of his head in one hand to control him, I reached out with the other to find his little hard-on. He gasped against my mouth as I touched him. I took his dick between thumb and forefinger and slowly jerked him, enjoying the feeling of such a young, tiny cocklet in my grasp. I loved girls, but boys had their own kind of appeal. I pulled back. "Lay down," I said softly into his ear, licking his earlobe and sucking it. He shivered and lay down on his back, stiff little spike sticking straight up. His cheeks and chin were already pink from my stubble. I was going to eat him up. Margaret got the toe of one shoe against Will's shoulder and pushed him back. He was damp-eyed with arousal, his lips wet and slack. Margaret hooked her thumbs into her knickers and pulled them down and off. I got a good luck at her smooth snatch, already glistening with juices. "Can I have those?" I asked, a wicked idea popping into my mind. She tilted her head to one side, smiled slightly, and handed them over. I took a quick sniff of the gusset -- inhaling the scent of her sopping wet pussy -- then put them beside the pillow for later. Margaret tapped Will's head again with her crop. "Get up here and eat me out. Get your tongue in my pussy and make me cum," she hissed. "I want your son to see you with my juices smeared over your slutty, needy face. Fucking pathetic." Will gasped and planted his face between her legs, immediately filling the rom with wet slurping and sucking noises. Margaret's body stiffened. She gripped his hair in one hand, hard enough that it must hurt him, and used the riding crop to slap his back and sides. He jerked and twitched with every blow, but he never stopped licking her pussy. Soon his skin was covered in small red welts. She wasn't being gentle. I turned my attention back to Luke. He was staring anxiously at his father, his little erection shrinking. That would never do. "Is she hurting Daddy?" he asked anxiously. "Yes," I said bluntly. "But he likes it. He wants it. If he wasn't enjoying it, he wouldn't let it happen, would he?" Margaret dragged Will's head up and out of her pussy. His face was smeared with her juices. "Tell your son how much you're enjoying this," she growled, hitting his back with the crop particularly hard. He yelped, his whole body flinching. "God, you're such a slut for this, aren't you?" "Yes," he moaned, staring helplessly up at her, "I am, I'll do whatever you want, you're so beautiful --" Her crop flicked across his arse. His yelp took on a sharper tone. She rammed his head back down between her legs. "See?" I told Luke. "He's happy. And I want to make you happy in a different way." "OK," he said reluctantly. I knelt in front of him and ran my hands over his body, enjoying the feeling of his smooth, warm skin. He was ticklish, so I ghosted my fingers over his ribs until he was giggling. When he was relaxed again, I sat with my legs straddling his, knees on either side of his calves, then leaned forward and kissed him. It was a slow, deep, slutty kiss. I sucked his tongue. It was easy to put a hand on his jaw and, with gentle pressure, keep it open long enough to spit a clear string of saliva into his mouth. He made a face but said nothing. Did nothing. "Good boy," I said, keeping his mouth open. I spat into his mouth again, then kissed his chin. "Swallow it down." I worked my way down his body, kissing and licking his skin. I sucked each of his nipples in turn, gently pinching with my fingers, interspersing with much harder pinches that made him tense. But he didn't cry out. Beside us, Margaret was moaning and shuddering through her first orgasm of the night, calling Will a worthless cunt-licker. The hard thwack of the crop told me she was really laying into him as she came. I almost felt sorry for him. She was just warming up. I glanced across at her as I kissed and sucked Luke's belly. She'd switched places with Will and was sitting on his face, his big hands holding her hips as she humped against his mouth and nose. She had the crop in one hand and was blindly slapping it behind her, intermittently hitting his legs, his cock, or his balls. His erection hadn't flagged; if anything, it looked harder and redder. He really was a pain slut. Then my sight was filling with Luke's delicious little erection, and I ignored Margaret completely. I opened my mouth wide and gobbled him down, filling my mouth with boy-dick. Luke finally cried out, hips bucking against my face. I held him down and sucked on that treat, swirling my tongue around his tiny cock-head, digging into his piss-slit. Luke was writhing and groaning. Opening my jaws further, I managed to get his tight balls in my mouth too. "Listen to that noise," Margaret was saying, her voice rough and unsteady as she rode Will's face. It was a wonder he could hear anything around her thighs. "A grown man is sucking your son's cock. He's going to make him cum any second now. That's what a real man does." She slapped the crop down on Will's hard cock. His yell was muffled against her cunt. Luke shuddered and moaned, his high, boyish squeals of pleasure intensifying. I knew he'd had dry orgasms before -- Will had told me about them, in detail -- so this wasn't unexpected for him. I sucked until his frantic hands pushed at my head. I let his swollen little cock and balls slip out of my mouth. "Delicious," was all I said, getting my hands under his thighs. Before he could react, or even recover, I pushed them up and back, exposing the tiniest little boyhole I'd ever seen. I dove on his hole as greedily as I had on his dicklet. Luke squealed again and kept on squealing, bucking against me. I held him down as I drilled my tongue aside his arsehole. It was so tight I had to spit and slobber all over him. It was the must fucking beautiful thing I'd ever seen. Margaret was screaming her way to another orgasm, riding Will's face and smothering him. He was thrashing now, clearly being deprived of air, barely even grunting with pain as she slapped his thighs with the crop. I worked my finger into Luke's tight preteen hole, coating it in spit and then slowly sliding it inside him. His squeals intensified. He was shaking uncontrollably as I found his boy-button and worked it with my fingertip, taking malicious delight in working him past the point of sexual comfort. Finally I pulled out, letting him slump back against the bed. He was panting, flushed, and streaked with sweat. I sat back on my heels and just stared at him, enjoying the beautiful sight. The bed dipping caught my attention. Margaret had got up and was moving over to the toys on the table, the inside of her thighs slick with juice. Her pussy lips were puffy and swollen. Fucking sexy in her own right, but only a pretender when I had this delicious little boy trembling in front of me. Will was gasping for breath, his big belly rising and falling. His thighs, cock, and balls were covered in red welts. His face glistened with pussy juice. "Did he pass out?" I asked as Margaret stepped into the harness. "Greedy bitch couldn't hold his breath long enough," she said dismissively as she tightened and adjusted the straps around her legs and waist. I wasn't fooled -- she'd wanted him to pass out. There was a massive fucking thrill in making someone pass out from lack of air. It was dangerous. But so was taking coke. So was giving half a Valium to a kid. Everything we did was dangerous. And did we care? Fuck no. Nothing mattered except pleasure. "You've sucked your daddy's cock before, right?" I said to Luke. A timid nod was his only reply. "Good. Show me what he taught you." He scooted out of the way and let me settle against the pillow. He lay down between my spread legs, draping his arms over my thighs, my straining erection right in front of his face. Margaret moved back to the bed, double-ended dildo and bottle of lube in hand, and smacked Will around the face. His eyes fluttered open. "All fours," she growled. "I'm going to fuck your needy cunt and show your son what a greedy bottom bitch you are. And I want you to watch as a real man fucks his mouth." Will let out a soft whine, half-way between pleasure and misery. The thin line where his deviant sexual kink lived. Will rolled awkwardly onto all fours. His fat stomach hung down beneath him, his cock leaking strings of precum onto the bed. Luke started lapping at my dick, working his tongue around the head. I let out a sharp hiss. "Good boy," I said. "That's good. Keep going." He licked all around the head, getting his tongue over my shaft, dipping down to work on my balls. His wet slurps filled the room. As Luke licked my dick as if it was a lollipop, I watched as Margaret worked one end of the massive dildo up and down her soaking snatch, coating it in her juices. She pushed it slowly inside her until it reached the middle point. Her eyes fluttered. Her fingers fiddled at the place where the dildo joined the harness, fixing it securely in place. When she was done, a thick, 9-inch monster jutted out from her pussy. She picked up the paddle and stalked back to the bed. "Open your mouth," I said hoarsely to Luke. "Now, boy." I reached down and squeezed his jaw to emphasise my point. The head of my cock slipped between his stretching lips. He knew to keep his teeth out of the way, I felt that immediately. I jabbed my hips up in instinctive response, making him cough and pull back. I let him do that. He wiped his mouth. Will was watching us, eyes wide and wild, mouth hanging open. "Let him do it, Luke," he moaned. "Let him do what he wants." Luke whined, the soft, frustrated noise of a kid who really doesn't want to do something. Tough. I'd paid for this, and I'd paid for the privilege of what I was about to do. Paddle in hand, Margaret had stepped up behind Will and was spanking his meaty arse. He cried out with each hard slap. She put more and more force into it until he fell flat on the bed, shaking and moaning. She kept right on whaling on his arse, alternating between the back of his thighs. Luke got back on my cock. I had the head in his mouth. I gave him a minute to adjust, then pushed more in. He let out a muffled whimper. I put both hands on the back of his head and pushed him down, shoving my cock into his tight throat. He tried to scream and pull off. I held him down. He was choking, thrashing. It only excited me more. I was panting, the feeling of my cock in such a tight tube incredible, the perversity of forcing this 9-year old child tightening my balls as much as the act itself. There was no finesse -- I fucked his throat. And Will was watching. He was sobbing softly now, but he was still watching. Margaret was rubbing his arse with her bare hand, the paddle abandoned, as she bent over to speak into his ear. "What a pathetic little cunt you are," she said, digging her nails into his flesh. He yelped but didn't take his eyes off me and his son. "A needy bitch. You're getting off watching a real man throat-fuck your boy." Luke's body was jerking. A moment later he went limp. He'd passed out. I pulled him immediately off my dick and laid him down. He drew a thin, ragged breath, coughing and choking. He looked beseechingly at his father. But Will -- who was now back up on all fours -- had his eyes closed, Margaret's fingers probing his hole as she smeared lube up inside him. Luke's movements were slow and uncoordinated. He tried to crawl away, but the Valium was taking effect. It was time to take his virginity. I wanted Will to be helpless, Margaret's monster cock pounding his insides, before I took his boy. I held the kid down and waited. Margaret smeared more lube over her strap-on. Will was trembling, his body covered in vicious red welts, but his dick was still hard. "Tell me what you want," Margaret ordered. "I... I want you to fuck me," Will stammered. "Fuck what?" She positioned the head of the dildo at his hole. "Fuck my cunt," he ground out, head dipping. "Fuck my slutty cunt." Margaret leaned forward and grabbed his hair, yanking his head back up. "Watch, bitch! Watch how a real man fucks your son!" Will whimpered as his pleasure boiled over. He shot a load over the bed, his spunk spraying wildly over the sheets before Margaret had even got her strap-on up him. His dick stayed hard, his balls tight. He had at least one more load in him. Margaret pushed a lube-slick hand into the middle of his back, pushing him down, forcing him to spread his legs to give her a better height. When she was satisfied, she started pushing her dildo inside him. Will dropped his head again, huffing and panting with pain. She was being firm rather than rough, moving until the entirely of the dildo was buried up his whoreish mancunt. Never mind Margaret, I was pretty sure I was about to get off on his degradation as well. I watched as she set up a slow fucking pace, something she could keep up for a while. I still had some prep work to do before I could sink my dick where I really wanted it to go. Will was grunting and moaning. I got up and moved quickly over to the table, scooping up the dildos. Margaret picked up the lube as I headed back and handed it over. Luke's body was limp and barely moving as I climbed back up on the bed. The Valium had kicked in. He was pliable and quiet. Aware, but not so much that he could fight back. Not yet. Not until I had him impaled on my cock. I took my time, lubing up the smallest of the dildos (barely thicker than my finger) and working them inside Luke's tiny little starfish. I would fuck him for a minute or two, working him open -- enjoying the way his gape started to increase, the way it twitched -- and lube up the next size dildo. For all Luke's earlier fear, I could see his body was enjoying this, whatever the fuck his mind thought. His dicklet was hard and twitching as I kept tagging his prostate. "You ready yet?" Margaret demanded. She was clearly getting bored. "This slut's about to explode." She slapped Will's red arse, making him yelp and shake. "Yeah." I looked down at the sweaty, flushed 9-year-old in front of me, at the way his legs were spread, the way his boycunt gaped and winked. "I'm ready." Margaret drew her hips all the way back, withdrawing the dildo almost to the tip. Then she slammed all the way forward, driving deep inside him and making Will yell. My balls were tight and hard. I wasn't going to last long. I fumbled for Margaret's knickers, discarded what felt like a century ago, and balled them up. I shoved them into Luke's barely resistant mouth, watching his eyes bulge with panic. My cock lurched. His fear was better than any aphrodisiac. I was going to hurt him, even with the prep, and every single adult in this room wanted it to happen. I fisted lube onto my dick. Held his legs back, pushing them roughly down against his shoulders. His pliable body offered no resistance. His cunt was a target I couldn't miss, and I positioned myself at that beautiful gape. I shoved my cock in hard, feeling his immediate resistance, enjoying the way his body tensed. Enjoying the sublime pleasure of his scream, muffled by the knickers in his mouth. Margaret was hammering away at Will's pussy, abusing his cunt as she pounded him. I matched her pace, burying myself in the convulsing little boy beneath me, holding him down as I bred him. Tears streaked down his face. I looked at Will. He was crying, too, but whether from his own subjugation or sympathy with his son, I neither knew nor cared. I ploughed his boy, luxuriating in my strength over that of a child's, in the power disparity. Will's hoarse yell rang sweetly in my ears. He came again, fresh spunk splattering over the bed. Margaret followed a moment later, her head thrown back as she groaned. Sweat ran down between her breasts. She hadn't taken her bra off, nor her shoes, and the image she made -- powerful, beautiful, in control of the needy slut writhing beneath her -- was enough to make me cum. I pounded the little boy beneath me and shot inside him, groaning, my body twitching as I filled him up. His muffled screams died down to choked sobs. I pulled out. The gape in his arsehole was beautifully obscene. Cum trickled out of him and onto the sheets. I lowered his legs back down, but moved to one side and pinned his arms. Margaret knew what I wanted next. We'd discussed it at length beforehand. It was a happy circumstance that these particular kinks coincided. She pulled out of Will's abused hole, then slapped his arse hard enough to make him gasp. "Suck Gavin's cum out of your son's pussy," she said, giving him a hard shove that made him fall into the slick mess of his own spunk. "While you're down there, clean Gavin's cock." Will's dick was hard again. Rather than marvel at his staying power -- not possible for a man of his age or condition -- I merely smirked at the knowledge that he must have taken a Viagra. Dangerous, if you take coke at the same time. Not my problem. Will crawled through his own mess and slumped over his son. I flipped the boy over and pulled his cheeks apart. Will buried his face in that gape, tongue lapping at my cum, sucking it out. Luke squirmed. I grabbed Will's hair and tugged his head around to my dick. He sucked it with the same mindless determination as he'd eaten his son's hole, making grunting noises of pleasure. I pushed him away before I could get hard again. Margaret and I had one last privilege we'd paid for. Luke had pretty much passed out now, exhausted sleep rather than unconsciousness. Will rolled over onto his back, hard cock sticking straight up, his own cum slicking his fat belly. Margaret got up on the bed. She straddled Will's head, but rather than lowering her pussy to be eaten again, she pissed on his face. A steady stream of golden liquid splashed into his open and waiting mouth. It spilled out and trickled down his cheeks, soaking into the bed, splashing his neck. She wiped herself down with a corner of the sheets and moved off the bed. Will flogged his dick with merciless speed, so fast and hard I knew it would be sore in the morning. He was groaning, taking pleasure in his continued degradation. There was one more act of degradation. I aimed my dick at his son and pissed on the sleeping boy's face, careful to get the wadded-up knickers in his mouth. My stream splashed over his chin, down his neck, even over his chest. I pulled the soaked lace out of the boy's mouth and shoved it roughly into Will's. Eyes closed, he sucked furiously, yanking his dick until another arc of cum shot over his belly. His movements slowed. His nostrils flared as he struggled to get enough air. He was sucking on the piss-soaked knickers in his mouth. Margaret and I shared a look. I raised my eyebrows in question. She nodded. And like that, we knew it was time to leave. We took our turns in the on-suite bathroom, cleaning our respective dildos, before dumping everything back in the bag. We dressed. As we left, Will had rolled his piss-wet body on top of his son's and was busy fucking his arse, his hand over Luke's mouth. I hesitated, torn by the lure of the depraved. Margaret touched my arm, a clear warning in her eyes. Yeah. We'd got what we paid for. Time to go. But I knew we'd be back.