4 comments/ 20051 views/ 3 favorites Lucky Jack Learns to Obey By: Sputnik57 He was in his fifties now, she was in her seventies, but her body was as supple and pert as ever. True her breasts were a little saggy now and her throat could not fully conceal the years, but she had looked after herself through her life, and indeed, many men had looked after her too but Jack remained her favourite. She may have aged in years but her authority remained untouched; she was as dominant as ever and enjoyed being serviced just as she liked it. As she sat, naked but for black stockings and suspenders, against the headboard, she toyed with the leash about the willing male's neck as he sniffed and licked her inner thighs and gently lapped at her delicately shaven pussy. She smiled as he gave her the usual obedient attention; she'd have her asshole licked next. "When it's time for me to go, you'll come with me. I want you there in the afterlife to serve and obey. If it's cancer, we'll have a nice little arrangement." Her mature pussy bulged with pleasure as she giggled at the thought. "I shall arrange a hook in the ceiling; I shall also prepare a cocktail of drugs. Before I am too weak to cope, I shall enjoy snuffing you first." She sniggered contentedly as she sensed his cock stiffening eagerly at the thought. "Oh yes, I shall find a nice silky rope and I shall thoroughly enjoy hanging you. I've always dreamed of doing that whilst mid-orgasm. You'll have your hands and feet bound and I shall milk you one final time as you swing." He lapped vigorously at her nicely aroused pussy as he thought of dying for her; he certainly wanted to come now. She was already close to coming with the erotic thought in her head. "When they find us, I shall be lying comfortably on the bed, my favourite vibrator deep inside me, my favourite slave hanging there, having willingly paid the price of worshipping me; a tidy pool of semen on the carpet below, in testament to enjoyment of servitude, even in death." She moaned excitedly and pushed his head down to tend her asshole as she now worked her clit with her beautifully manicured fingers. He humped the sheets excitedly as the tang of her sweetly puckered asshole combined with the thought of being hanged. She moaned with satisfied ecstasy as she came; his tongue deep in her anal tract. He moaned too as his cock spurted in a tribute to her wicked tease; a glorious sense of submission coursing through his body as he spent again and again. The two giggled together as their orgasms subsided. He rubbed her belly as he thought of the rope. "You know I'd willingly go that way, whenever you are ready, but hopefully we'll both be around for a while yet. I wonder if we'll re-live our relationship in the afterlife? " She tugged at his arm and he slid up the bed and cuddled her with the affection that had long existed between them. She smiled as she kissed his forehead. "Yes, that would be wonderful; do remember how naughty I was when we first met? " He giggled again as they drifted off to sleep; his mind going back to 1975... Jack had had the 250 Kawasaki for a year now, but the snarling sound of the three cylinder two-stroke still turned heads as he wound up the throttle, 'showboating' as most 18 year olds were apt to do, at any opportunity, especially when girls were around. He was a working class, blue collar bum and proud of it; this made him very appealing to the girls in the middle class town he chose to frequent. He had a taste for 'classy birds' and left his council-house town for this leafy and affluent neighbouring town to hang out. His 'rough diamond' attitude, earthy good-looks combined with the most exotic250 that was available at the time, ensured he was a favourite with the Fionas' and Beatrices' whose fathers' would definitely not have approved. At the moment, there was one girl in particular who caught his eye; Marcia Fortescue lived in The Avenue, the most expensive street in the town. She had given him racy looks and he had walked her home from the war memorial where they all congregated, on a couple of occasions, sneaking the odd kiss. Her mother had seemed less hostile, almost friendly to him in comparison to the usual rebuffs he'd normally experienced with girls parents; this left him feeling a little bold this afternoon and he rode his bike right up to the house. He removed his crash-hat and rang the bell at the door of the huge house. The door opened and he was greeted with a stern look from Marcia's mother, which quickly developed into a warm smile. This made him feel a little uneasy, though his cock began to rise automatically. He broke the silence. "Err.., hello Mrs Fortescue, I wondered if Marcia was available?" She looked about the entrance to the drive and then to his motorbike. "Could you please park your bike round the corner, out of sight, thank you." Jack thought nothing of this; it was not an unusual thing to ask; people were very particular about appearances in this neck of the woods. He duly wheeled his bike through the gravel and then through agate by the side. No-one would know he was there. Mrs Fortescue smiled warmly again and offered him in. His cock swelled all the more as he watched the rear of the shapely woman; she was about 37 to 40 and very attractive. She took his leather jacket and sat him down at one end of a two-seater leather sofa. He thanked her again, once more addressing her as 'Mrs.' She looked at him warmly. "You may call me Bella; I'm a Belinda really, but that sounds a little pompous." He gulped as he looked down to his nether regions and smiled; she knew she excited him. He now waited nervously for Marcia to make an appearance as 'Bella' now asked if he'd like a drink. "Oh, I'd love a coffee." She now toyed with her collar length hair and pursed her lips. "I like to have something a little stronger at this time in the afternoon; would you like a scotch or rum maybe?" Jack somehow felt compelled to oblige her. "OK, can I have a rum please." She came back with two bottles, poured herself a scotch and he a liberal amount of rum. She then sat next to him and pulled her skirt up a little and crossed her long and elegant legs. "So how much experience have you had with girls? I hope my Marcia is not going to come to any mischief with you; I can see why she might find you attractive." Jack was lost for words at first; Bella had purposely posed two questions at once to wrong-foot the masculine lad who sat before her. She allowed her skirt to ride further up her legs, exposing more thigh and increasing his erection. "Oh, I've had a few girlfriends... nothing too serious. I think Marcia's very pretty." He took a swig of the rum and nearly sent it down the wrong hole; he coughed nervously as Bella now hit him with a bombshell. "Marcia will be so happy to hear that you think she's pretty... when she comes back from France. But I hope you'll stay for a while and keep me company." Jack was dumbstruck as she edged closer to him; he could now feel the warmth of her thighs. "Err yes...Bella...of course." His head swam as he knocked back the rum in a nervous reaction and she quickly poured him another. She smiled wickedly. "Oh good! I shall just go and put some more relaxing clothes on, and we'll have a nice chat about girls and women; I'm sure I can help guide you to what some girls really want." She put her hand on his thigh close to his obvious erection and gave his leg a squeeze as she stood up. He gulped down another drink; he felt like a fly in a web at first, but the drink hit his youthful head pretty quickly. He suddenly relaxed; what harm could come of it?, her mum was obviously lonely with Marcia gone for a while and it was nice to have a conversation with an older, mature woman. His cock stiffened again as his thoughts of her thighs and she was suddenly there again. His jaw dropped as she sat next to him in a black silk robe, tightly belted at her slim waist; her mature breasts wrapped in the soft material, her nipples poking through. She crossed her legs and the split in the robe went close to her pussy. He started to breath heavily. She smiled seductively and put her hand on his crotch, rubbing his erection unashamedly. "You are going to come upstairs with me now; we'll be so much more comfortable, and I am going to show you how you can best be of service to a woman." His legs went to jelly as she took his hand and led him up the elegant stairway; he was powerless to do otherwise, she already had complete control of him. His cock was ready to burst as he watched her delectably mature ass twist and shimmer in the black silk. She was going to make him hers. Lucky Jack Learns to Obey Ch. 02 Jack followed her meekly into a large and very boudoir-like bedroom; her sweet feminine scent mingled with the perfumed scent of the room, invading his young nostrils and seeming to hold him transfixed as she sat on the end of her bed and crossed her legs, adopting an assertive manner which would not be denied. Jack, though still very young, had always had an unconscious desire for dominant women; as he flitted through the pages of girlie magazines, it was always the pictures of older, authoritative women which made him come the strongest, and he had developed an attraction for those darkly seductive ladies who carried canes etc. He was about to learn that Bella Fortescue was just such a woman. She undid her black silk gown and displayed her full round breasts with a seductive smile. "I'd like you to take your clothes off right now, so I can have a look at you too. You will then tell me about your sexual experiences with girls, and I shall then show you how a woman likes to be pleased." Jack gaped at the gorgeous woman before him and shyly removed his clothes. She smiled with satisfaction as he stood there, his youthful six inches jutting upwards at nearly 45 degrees; she could have hung her overcoat from it without it sagging; she would enjoy watching him shoot his seed for the first time. She asked him to kneel at her feet; he did so without hesitation. She wagged her loose foot at him. "Caress my foot; I find that so soothing when holding conversations about sex." Jack obliged and found that just this action had his cock stiffer than ever; he had no fetish for feet, but the soft contact of the assertive woman's flesh, and the elegant manicured look of her delicately pedicured and brightly painted toe-nails, excited him no end. He could now also detect the odd waft of something more exciting; his prick and balls tingled as Bella's arousal grew. "How many girls have you pleased with that stiff little cock of yours; I know you working-class boys are very forward in that respect, but please; be honest with me, I shall know if you are telling lies and I will not be happy with you." Jack felt very small and immature as he divulged his full sexual experiences with girls. "I've only had sex with two girls before... neither very successful." Bella gave a contemptuous laugh as he continued to caress her warm and smooth foot, his eyes creeping up the length of her beautifully shaped legs, her supple and fleshy thighs, hoping to snatch a glimpse of the pussy which was teasing his nostrils all the more with each passing minute. She was very pleased with his answer; it showed he had not been too corrupted by experience, he was ideal for her purpose; she would mould him just as she wanted him, and he was perfect for her purpose. She pulled her foot from his hand and slowly crossed her legs the other way, ensuring he was allowed a glimpse of her pussy, now wet with arousal; the scent blossomed from it as she crossed, making his cock dribble as it bobbed excitedly. She smiled as she eased her other foot into his hands. "Had you spent the night in bed with either of them?" "No... it's something I've always dreamed of; both my experiences were opportunities taken when the chance was there; my first was on the floor of the girl's parents lounge, and the second was in a field of long grass in the summer." Bella pushed her foot forward into his hairless belly and allowed him to stroke her calf. "Would you like to spend the night with me, all tucked up warm and comfortable?" Jack swallowed hard as he looked the mature woman straight in the eyes. "Yes, I would love that Bella." He blurted out his response almost in disbelief at what he had heard her say; she giggled with pleasure; she loved to tease experienced submissive males; she had developed a taste for this since divorcing her obnoxious husband, at first through simple spite of all men, though this had now developed into a full blown fetish. This youth was a whole new experience, and his willingness to comply with her whims excited her no end; she would enjoy introducing him to her circle of dominant female friends; some of whom would treat him to pleasures he could only dream of. She eased her legs apart and put both feet to the ground on tip-toe. Jack was transfixed by the cleanly shaven pussy before him; he so wanted to come. "What foreplay did you treat your girls to, before you had sex with them?" She pulled the silk from her shoulders and placed her arms behind her, arching her back and displaying her pussy and breasts to best effect. "Did you lick their pussies?" She began to slip a finger up and down her moist slit as she waited for the negative response she hoped upon hope she'd get from the young man. "No Bella, I've never licked a girl's pussy." He gasped as he spoke not daring to believe that this gorgeous and mature woman would demand that he lost his oral virginity on her? Bella smiled with deep satisfaction; her pussy tingled gloriously as the erect and youthful cock before her, dribbled pre-cum visibly, she knew he was on the verge of exploding. "Oh you poor boy, would you like to lick mine?" Jack was stunned to silence and just stared at the delectable pussy which now opened up before him as Bella spread her thighs further. He leaned forward, mesmerised, as she put her hand softly behind his head. She whispered softly and confidently as he nervously leaned toward his succulently scented goal. "Don't worry, I shall show you how it's done; you will find it most natural after a while, and most enjoyable. I shall teach you many things now I have you." Jack could barely control the pulsing in his cock and balls as he gently probed Bella's soft and hot sticky lips for the first time. It was as much he could do to stop himself from grabbing his cock and jerking himself to oblivion there and then; the smell and taste of her moist and aroused cunt was overpowering. Bella giggled softly as she lifted his head slightly. This was so enjoyable, he was so gentle; he would serve her and her friends very well in the time to come, he was definitely hers now; there was no way he could escape from her womanly charms after this. She lifted her thighs as he lapped deliriously at the pungent and wanting nub of her womanhood. She gasped as he licked close, but not close enough to her clitoris. She lifted his head a little more. "There, you be a good boy and caress that little bit near the top of my crack with your tongue." Jack obliged and Bella moaned with pleasure as he found the little bud at the apex of her juicy womanhood; he stretched his tongue and rasped as hard as he could. Despite his cock wanting to spurt, he found hearing the mature woman moan as he pleased her just as pleasurable; submission and servility to women would come very naturally to him, and Bella knew this. Close to coming, she wanted him to do something else for her; as she pulled his sticky face from her pussy she knew he would now be willing to do anything for her. She panted, now impatient to come; she wanted to arrive, knowing her youthful capture knew his future position in life. She focused wickedly on him. "There's something else I want you to lick now." She pointed a sharp finger down to her soft brown ring as she lay back on the bed; Jack was not sure at first, he had not licked pussy before and had thoroughly enjoyed that, but was not sure about licking her asshole. He thought he might gag, but the delectable orbs of her sumptuous ass beckoned him home. Bella became impatient and commanded him sternly for the first time. "Lick my asshole now!" Her words ensured he carried out the task for the first time; she had commanded he do so. His cock jutted rigidly at the recognition of being submissive to a woman, and enjoying it. He sniffed first at the sharp and rich sent of her asshole, and was more than pleasantly surprised; he did not gag, quite the opposite; the honeyed taste of her asshole had him yearning to come more strongly than ever. Bella moaned in ecstasy as she rubbed her rigid clitoris to a satisfying orgasm as the willing youth probed deep into her anus in an ecstasy of his own; he could never have imagined it could taste and feel so delicious; he sniffed at the combined sent of mature cunt and savoury asshole as her finger worked violently at her throbbing clitoris, sending fresh juices down the crack of her cheeks for the willing lad to savour. The act of licking her ass made his own asshole tingle; he knew this was a symbolic act of submission and wanted to be owned by her completely; his cock was ready to spurt for her in any way she chose. Bella erupted in a tremendous and thoroughly satisfying orgasm, squeezing the youth's head between her thighs as she came. She marvelled at the way he kept probing and licking, long after her orgasm had subsided. She smiled with satisfaction and pulled his head away. "Get up here and lie on your back on the bed. It's high time I saw what you have for me." Jack did not hesitate. As he lay on his back, Bella giggled as she straddled his face. His cock pulsed urgently as her sweaty and sticky crotch hovered above his nose, and then shifted forward slightly before descending; his eager tongue was presented with her delicious asshole once more. "I think you've fallen in love with ass-licking already! That will make you very popular with some of my friends I intend to introduce you to. Now we'll see how much cream you have for me." Jack writhed and probed in ecstasy as the mature Bella's delicate hands worked his stiff and eager cock; he would come in no time at all, but would have plenty in reserve for later. He wanted the day never to end; what did she mean about introducing him to friends? As he lay in complete submission for the first time, Bella's beautifully mature body squatting on his face, he went into a delirious ecstatic rapture as his balls pumped like there was no tomorrow, shooting his hot semen high in the air and onto the soft globes of his mistress's globular breasts. Bella laughed victoriously as her new and tender conquest spent over and over, draining his balls in pure ecstasy. Bella licked her fingers clean of the salty mess after the last loops of come had pulsed weakly onto her hand. She lifted Jack and had him kneel facing her on the bed. She kissed him on the lips for the first time, and then reached into a draw by the bed and found a studded collar. "Would you like to be mine?" Jack nodded his eyes and mouth wide; he was willing to die for her. She smiled with satisfaction as she buckled the black studded collar about his neck. "You'll wear this whenever you are in the bedroom with me; it is a sign of my ownership of you. I am going to arrange something to send to your parents, so as they will not worry about you; you shall be indentured into an apprenticeship, which will mean you have to live away from home. It won't be a complete sham; you will enjoy an apprenticeship like no other; somewhat removed from the norm but very pleasurable." She giggled as she pointed to semen dribbling down her breasts. "I think you should clear that mess up whilst I phone a friend to tell her about my new acquisition; I am so looking forward to showing you off." Jack lapped at her silky breasts, tasting his own semen for the first time. His cock began to rise again already, as he teased her still erect nipples and listened to her phone conversation. "Hi, Madeline... yes it's Bella... I hope you're feeling horny today; I have a treat for you over at my house, you'll be so jealous." Lucky Jack Learns to Obey Ch. 03 When the doorbell rang, Bella tossed a pillow to the floor in the corner of the room. "You kneel on that right now, facing the door, and I'll bring my friend up to see you." Collared and naked, Jack was mesmerised by the situation; he did not fully understand submission yet, but his cock stiffened as he was told. He realised this was much more than youthful respect for authority; he was now yearning to be of service to her. he yearned to lick her asshole again as he watched her slip on the black silk robe and watched her beautiful cheeks move as she left the room to greet her friend. He waited, his cock now stiff again as he knelt listening to the murmurs and giggling as the two women came back up the stairs. He took a deep breath as the door opened. Bella walked in with a broad smile on her face as she viewed her new conquest kneeling obediently, and erect, waiting like a puppy. Madeline followed, and Jack's first sight of her made his balls and anus tingle. Madeline was a very severe looking plump woman; she wore a tight skirt and top which accentuated her plump curves, her red hair was up in a bun; she was every inch the assertive headmistress in Jack's eyes. She removed her glasses and moved over to jack, stroking his hair. "Oh he's adorable; I do so like it when you can catch them at a young age; please say you'll let me have some fun in moulding him." Jack's cock bobbed excitedly as he smelled her feminine perfume and listened to her words; he was already resigned to beginning a new chapter in his short life and it got more exciting by the minute. Bella smiled at Madeline and let her silk gown drop, standing naked with erect nipples and looking very pleased with herself. "Of course Madeline! Just why else would I have asked you over? Young Jack would love to lick your asshole while I watch wouldn't you Jack." Jack had little option or little hesitation with his reply; he had gone from never having experienced oral sex, to licking both the sex and anus of a mature woman, and now he would sample the scent and taste of another in one afternoon. "Yes Bella, I..." Madeline slapped his face, more playfully than in spite, much to the approval of Bella. "Yes MISTRESS Bella; we'll have to instil some strict obedience in you right from the word go young man. You shall address all women as 'Mistress' from now on." Jack's balls tingled with a strange pleasure at the chastisement. "Yes Mistress Madeline." Jack's cock dribbled as the stern plump woman undressed before him; her ample breasts were slightly saggy but unbelievable attractive to Jack. Madeline smiled as she furthered the tease, and his training. "Yes Mistress Madeline what?" She dropped her skirt as she said this, and turned with her beautiful round ass in his face as she peeled her panties from the plump and quivering cheeks. Poor jack struggled to get the words out as she caught a whiff of her intimate womanly scents as the sticky panties dropped to her ankles. "Yes Mistress Madeline, I would like to lick your ass whilst Mistress Bella watches." The middle aged woman went down on all fours and spread her cheeks invitingly; Jacks cock was close to spurting of its own accord as he took in the tangy whiff of her asshole and the soft musky scent of her richly aroused and bulging cunt; a tiny tuft of red hair evident on her otherwise cleanly shaven and inviting womanhood. Bella laughed as Madeline wobbled her delectable ass at the boy, who was both learning and enjoying the dominance of the better sex. "What are you waiting for? Lick boy, lick!" Jack yearned to come again as he sampled the beautiful tangy taste of the sternly authoritative woman, the warmth of her delightful folds holding him sufficiently captive on their own. Bella rubbed her pussy as she watched her Jack service Madeline, now she looked at him obliging another woman she was now certain he'd be hers to have as a pet and treat her friends for favours. Madeline moaned with pleasure as Jack licked her asshole in complete submission to her. "Good boy, good boy, I think you've deserved your first treat from Aunty Madeline and your new Mistress." She pulled her soft cheeks way from him and had him lie on the bed. Bella came over and the two giggled as they straddled him. If Jack's sense of enjoyment of submission had been aroused before, it was now completely and utterly exploded into pure heaven. He was trapped below the ample cheeks and delectable ginger pussy of Madeline, as she ground her hot slimy cunt and asshole across his mouth and nose, taking care to ensure his arms were trapped by her luscious calves and thighs; his Mistress Bella sat on his middle and took his cock deep into her hot aroused pussy, and ground away. Jack was trapped and at the complete mercy of the two stern women; he fought hard to stop himself from coming, such was the ecstasy he experienced at being trapped and used as a plaything by two women who had complete control over him. Bella moaned in orgasm, and Madeline groaned and sighed as her beautifully scented pussy and asshole ground more and more urgently on Jack's face. Try as he might to hold back, it was no use; an ecstasy like he'd never known before, wrapped his entire body as he squirmed and struggled beneath his two mistresses, he bucked as best he could as he was held firm by the two dommes. Bella teased on having finished her orgasm. "Good boy, that's it, give yourself up for your new mistress; give your cream to me now, I'm going to have you lick your mess from me when you're done." Madeline seemed to hover and her engorged cunt stuck firmly over his mouth as Jack exploded into Bella's welcoming pussy, which seemed to suck the cream from his balls like a spider devours its bound prey, as he jetted again and again in absolute heaven. The smell and taste of the ginger cunt, the feeling of helpless captivity, along with the warmth of his mistress's cunt and the promise of licking it clean made him shoot like never before. Madeline moaned in ecstasy too and her pussy trickled more juices for Jack to lovingly lap and swallow as he bucked and squirmed in submissive heaven. The two women giggled victoriously as all three orgasms subsided. Bella lay back on the bed, spread her legs and simply pointed sternly at her messy and spent pussy. Madeline stroked Jack's back affectionately as he set to the task of lapping his own salty cream from his mistress's sloppy and pleasured cunt. Madeline was most happy to have been invited. "You've been a good boy. Bella and I will put a letter together to ensure your parents do not worry about you; you're going to have a nice little holiday with Bella at Aunty Madeline's Villa in Corfu very shortly. There are lots of ladies we know who'll be delighted to have you service them; they do so appreciate a young and obedient male who knows his place. Are we going to take him to Deerhampton Manor Bella? He'll have to learn about the more 'severe' treatments t some stage." Jack felt Bella's pussy pulse at the mention of the manor; his cock began to stiffen instinctively as this seemed to have some significance as yet unknown to him. Bella stroked his hair as he continued to lap at her womanhood, eager to ensure every last drop of his cream was licked from her. "We'll see how he develops after some discipline in Corfu first; I'd love to take him to Deerhampton, but I want him to have a gentle introduction first; he's taken to submission so easily thus far." The two women fired up a computer in the corner of the room and began to type out the letter to his parents, from the company that Madeline owned; 'Athena Services Ltd.' Jack was to be apprenticed with the company which would mean he would be stationed away from where he lived and quite often abroad. Jack was made to kneel in the corner, with Madeline's panties over his head; the gusset across his nose to ensure her sweet scent kept him aroused. His cock rose as the two discussed the fact that he would go home for the last time that evening, give the letter to his parents, and report back for 'work' tomorrow. The plan finalised, the two sat naked on the bed once more, and Jack's cock rose rigidly again as they commanded he join them. Lucky Jack Learns to Obey Ch. 04 Jack rode the Kawasaki back home like he'd just passed his test; he was shaking with disbelief at his experience and would take no chances on this short journey, and the return. He took one hand from the handlebars to feel the rustle of the letter beneath his leather jacket; yes, it WAS there -- this had been no youthful wet dream. His parents scanned the letter and wished him luck; they joked he'd been eating them out of house and home anyway. The last night at home in bed was spent with a permanent erection; he sniffed at the shirt he'd been wearing in the hope of getting a faint whiff of Bella. He wanted to wank so urgently as he thought of Bella and Madeline; he wanked every day normally, but managed to refrain, he so wanted to spend at their feet once more. Bleary eyed next morning through so little sleep, he waved goodbye to his parents, having strapped a small case of his clothing to the rack on his bike and put the remainder in his rucksack. He approached Bella's house slowly, half expecting there to be no answer; this must be some sort of bizarre trick to teach him a lesson for sniffing round Bella's daughter. He already had a speech worked out for when he returned to his parents with the adventure over. Before he had time to turn the 250's engine off, a gloved hand opened the gate; it was at this point he noted an Alfa Romeo parked behind the hedge. The gloved hand beckoned him through the gate in elegant fashion; it was strange just how a hand could be so obviously effeminate. Jacks balls tingled as he edged the bike through the gate and turned the engine off, and noted Bella dressed in very horny fifties style casual dress. She pointed to a large shed by the garden wall, its door already open. "Put that nasty smelly bike in there; you'll not need that for the foreseeable future." He took the case from the bike and duly covered it with a tarpaulin to keep it from sight; Bella looked him up and down with contempt as he retrieved the case and she locked the shed door, he could see that she was trying not to smile, as she was obviously pleased to see him. He was taken indoors and made to strip off immediately. Madeline sat sipping coffee and smiled with satisfaction as she viewed the naked male's obvious excitement. "We'll have you suitably attired for our trip; you must compliment the way we dress at all times. I don't doubt that some of your clothes are suitable." Bella dumped his jeans and t-shirt in a corner, gave him fresh underwear to replace the fresh underwear he'd put on 90 minutes ago and handed him a bag which contained chino-like slacks and a buttoned cotton shirt. The two women smiled with satisfaction as Jack did just as he was told; he blushed a little as he stood naked, his excitement at being there on display to the women only too obvious, he panicked a little as he heard footsteps coming down the stairs; he had no time to put the underwear on. He took deep breaths as the women giggled at him when a sumptuous blonde woman in her early forties strutted into the room on red stilettos, tiny hot pants over black tights. Jack gulped as she strode right over to him and took hold of his erect cock. "OOhhhh! You must be Jack. Why he's adorable, and I'm so lonely with my young Craig up at Deerhampton at the moment." The women giggled all the more as she gently teased his now absolutely rigid cock. Jack panted as her expert teasing of his glans made his knees weak, and he couldn't help but notice her nipples pointing through the fabric of her silky blouse; her full rounded breasts nicely firm without the need for a bra. She looked him in the eye with a wicked glance as she licked her bulging red lips, then turned to the smiling women who were now both enjoying a cigarette as they watched the bewilderment of their new young catch with delight. "Oh please say you'll let him come and warm my bed for me; I've had such a long drive and could do with being pleasured before having a nap on the one hand, and I'm so excited about a lovely domineering couple of weeks in Corfu in just two days from now." Jack panted softly as the mature blonde oozed sexual presence and continued to work his young cock. Within 15 minutes he had gone from doubting he would ever see Bella again, to being propositioned by an extremely attractive woman he'd never even seen before; he was already close to shooting all over her black tights. Bella crossed he legs and gave Jack a teasing smile. "Well Jack? We've told our friend Marie here, how you like to lick asshole and pussy. I think you should go down on your knees and beg permission to service her." The three mature women sniggered at the helpless young male, thoroughly enjoying their control over him and his willingness to be subservient as he sank to his knees and stared at the gorgeous nylon clad thighs before him. Marie sniffed and licked the fingers that had nurtured his bell-end and sneered with satisfaction as she awaited his request to be of service to her. As Jack summoned up the courage to ask, he heard the women giggle as Madeline tapped the table to attract his attention. As he looked at her the redhead looked at him sternly, her dominant thighs crossed magnificently, making his balls tingle. She mimed at him 'MISTRESS'. Jack's anus tingled with a mixture of fear and pleasure as he looked up at the commanding blonde and thought of the trouble he'd have been in on forgetting to address her properly; he did not want to displease any of the women. She sneered at him and put her hands on hips in assertive fashion, Jack's mouth opened. "Please Mistress Marie, I beg you, may I be allowed to lick your asshole and pussy." Bella and Madeline applauded lightly as Marie licked her lips once more and sneered down at her young charge. "Come with me young Jack; you shall help me undress, I may allow you to sniff my panties first, would you like that." Jack could only nod his approval as Marie had him stand and led him upstairs by his erect cock while the other two went through his things, discarding items they did not approve of. Marie walked him to the room she'd been given and felt his cock pulse to full rigidity as he saw the items she'd brought with her, laying on display from her open suitcases; leather outfits, whips, crops and strap-on phalluses were in abundance. "I do so love to dress like a tart when I'm away; you can peel off these hot-pants now, I'm eager to know how your tongue feels, then we'll have a little fashion parade. I so miss my Craig; I always like to have him masturbate for me whilst I display new things I've bought; I shall send him a postcard from Corfu to say I'm not lonely at the moment as I've found someone to lick my asshole. I know he'll appreciate that. Just think, he's probably enjoying a caning right now, and will be so pleased to know I'm being attended to; I know he'll learn to love the sting of the cane during his 'Total Discipline' course at Deerhampton, I shall have to re-stock my rattan supply." Jack knelt and undid her tight denim hot-pants; they did indeed make the mature and assertive blonde look exquisitely tarty. Removal of these revealed the black tights over lacy white panties. Jack's balls tingled as her excited sex gave off its first whiff of arousal through the nylon and lace. She pointed to her feet and lifted each in turn, and Jack removed her red stilettos. She smiled contentedly and pointed to her tights, which Jack duly eased from her torso and rolled down her shapely legs. Marie giggled as she watched his cock bob in recognition of his enjoyment at the sheer feel of the warm nylon and the smoothness of the flesh beneath. She sneered as she enjoyed her control over him. "You will now remove my panties and give the crotch a good sniff; if the scent meets with your approval you must beg to be allowed to lick my pussy and my asshole.' Jack's cock dribbled as Marie removed her silky top and exposed her ample breasts as he peeled the soft panties from her and took in the delicious scent of her exposed womanhood, which was smoothly shaven; her sweet butterfly pink and ready to be sampled. Jack took the panties and shivered a little with anticipation as he viewed the slightly yellowed and moist gusset. Marie giggled softly as he buried his nose in the soft and richly scented gusset. The exquisite scent ensured his cock remained bone-hard. And Marie was delighted as she saw him move the gusset to the rear to sample the delicious tang of her asshole. The erotic mixture had Jack yearning to service the real thing. "I beg you Mistress Marie; please allow me to lick your pussy and asshole." These were simple commands met with simple requests but the reality was that Jack was fast learning discipline, humiliation and submission; he would learn to enjoy being controlled completely and the women delighted in the affirmation of their utter supremacy. The mature and shapely blond slowly lay back on the bed and lifted her knees, offering Jack a mouth-watering view of her delicious pussy and asshole. "You may start with my pussy; I shall tell you when my asshole is to be serviced. When you've satisfied me, we shall have a little fashion parade as promised; I'll see you shoot your cream and then you'll keep me warm while we nap." Jack eagerly climbed onto the bed and put his nose and then tongue to her glistening sex; he was not disappointed with the tantalising aroma and sublime taste of her moist cunt, and Marie was not disappointed with the fledgling slave's attentions to her folds and lips. She purred with satisfaction and toyed with his hair as he gently lapped and sniffed with enthusiasm. Marie pointed her toes to the ceiling as he rasped at the nub of her clitoris; she urgently needed to come now, and eased his face from her slippery pussy. "You'll lick my asshole now; it's so in need of refreshment after being in those tight hot-pants." Jack almost shot his load on the sheets as he took in the sharp and delectable whiff of her softly puckered asshole. Oh how he longed to shoot his mess on the soft sheets as he licked the puckers and explored the tangy hot depths of Marie's hot anal passage. He worked his tongue urgently in the delicious tunnel as Marie tensed her legs as they pointed skyward while she worked her clitoris to the point of no return. Jack could not believe the heaven he now found himself living in, as Marie's asshole pulsed and squeezed his tongue as she announced her orgasm with a long moan. True to her word, Jack was made to kneel on the floor and masturbate while she paraded in exquisitely dominant poses with the articles of clothing and assorted punishers she had ready for the trip. At last she donned a latex cat suit and bent over with her ass in Jack's face; her recently pleasured cunt and the luscious divot of her asshole illustrated beautifully in the second skin of the shiny black latex. Jack could hold back no longer and groaned as his rigid cock gratefully spurted in ecstasy as the dominant woman posed before him, sneering with delight. "Now I have you! Show Aunty Marie how much you appreciate her show; maybe I'll cane you just for good measure." Jack moaned all the more and spent his balls, watching the hot white semen dribble down the black latex made him shoot for what seemed like minutes. He panted to a halt and hung his head, exhausted, as Marie laughed at him. She ensured he licked his mess up, before peeling the latex off and ordering Jack between the sheets. She smiled softly as she held him close and closed her eyes. "Bella, Madeline and I are going to have so much fun with you in Corfu. You really are in for a treat." She giggled as she felt his spent cock try to rise again against her thigh. Moments later they were both asleep. Lucky Jack Learns to Obey Ch. 05 When Jack opened his eyes, Bella was sitting on the side of the bed smiling. His recently spent cock was being nursed to a full erection again by Marie; her scent and the thought of being dominated by her and Bella had him ready to perform again. He had never really given any woman over 30 a second glance before, but would now have the same attitude for women under that age; he was now well and truly enslaved by the scent, smell and divine elegance of mature women, and they would put him to good use. Bella smiled at Marie with a hint of jealousy she could not hide; Jack was her prize and though she enjoyed seeing him please her friends, she knew how males could be entranced by the attractive and domineering blonde. "You make sure you leave some of him for me; I don't want him worn out before the trip." Marie smiled and gave his tingling balls a gentle squeeze, making him gasp. "You were not kidding when you said he likes to use his tongue; he's adorable, and SO obedient. I can't wait to see you parade him on a leash before our friends at Kassiopi." She smiled wickedly as she felt Jack's cock stiffen at the thought of being 'leashed'. His cock stiffened to rigidity as Madeline appeared in doorway in a tight bikini; her camel toe invitingly on show, she smiled wickedly as she saw Jack blush, but unable to keep his eyes from the sumptuous thighs and delicious mound of Venus. "Am I the only one who's trying on my new holiday things like we said we would? I'm so anxious to see our catch in his new things." She giggled and strutted forward, teetering on the new high high heeled sandals she sported, which made her magnificent legs seem even longer to Jack. He was mesmerised as the horny redhead pulled the quilt from the bed, exposing both he and Marie. The blonde shrieked with laughter as the dominant redhead took Jack's arm and hauled he and his bobbing erection from the bed. The other two laughed hysterically as she led him away, casting scorn upon his excited cock. "Oh you rude boy! I've a mind to put you across my knee and give you a good spanking!" This did not help quell Jack's erection, nor did the site of her ample ass cheeks quivering in the bikini bottom as she towed him along; he felt the tight grip of her hand in his, and thought just how welcome a spanking would be. The other two followed, giggling; Marie was draped in a sheet and helped herself to some wine as Bella and Madeline marshaled Jack; dressing him in various casual but smart outfits; they were not necessarily the style of clothes that he would have chosen himself, but the mere fact that he was being told what to wear by the women was a thrill in itself. When they had finished pleasing themselves with what Jack would wear at certain places, he was stripped again and made to kneel in the centre of the room while the women prepared to try their various outfits. Bella stood dominantly before Jack and smiled sternly at his semi-erect cock. "You'll help me strip, and you may sniff my panties while I try on some of my sexier outfits; if you're a good boy and sit quietly I may allow you to masturbate for the three of us, when we are suitably attired." She looked at the clock and smiled. "Yes, plenty of time for you to perk up again before you grace my bed and service me tonight." The women chuckled as Jack's youthful cock quickly developed a full erection again; Bella smirked as he fumbled excitedly with the lower buttons of the fifties style dress which accentuated her full body shape so sexily. She released it from her shoulders and let it drop to the floor, then pointed to her panties with a satisfied grin before removing her bra; her full mature breasts mad Jack fumble with her panties as the other two women stood close, increasing the pulsing of his erection. Her ample breasts were still very round and firm without support, any slight sagginess simply enhancing their mature beauty; she smiled softly and her nipples hardened as she saw his excitement. He swallowed hard as he slipped her panties down her legs; she stepped one foot clear and lifted the panties with the other. Jack took them and willingly sniffed at the beautiful feminine scent of the crotch, his cock now rigid at the delectable smell of mature pussy; he wanted to masturbate there and then. The three women smiled and moved gracefully as they chose various items to pamper themselves with, and tease their admiring onlooker; Jack sniffed, intoxicated by the delicious scent of the panties as he watched the women with aching balls; they bent in various ways, showing their mature ass's breasts and legs as they put on a seductive three woman perpetual strip tease show for their young captive, who they would delight in watching spurt his tribute shortly. Jack's cock was dribbling by the time the women had carefully worked through day wear, evening wear, bikinis and then delivered their final tease by saving their risque erotic wear till last. Jack was gasping with excitement as he was allowed to choose what the three would wear while he masturbated before them; faced with three strutting latex, leather and satin wearing dommes, he was at last commanded to stroke his cock while they sneered down at him in dominant fashion. The three posed and taunted their submissive admire in order to see who would induce his orgasm first; Marie pushed a latex clad leg with shiny spiky boot toward him, Bella swished the air with a cane, and Madeline promised him a thorough spanking if he messed on the carpet. The three laughed in a derisory fashion as he moaned in ecstasy, arched his back, and shot wad after wad of good wholesome semen toward the trio. Jack was made to clean his mess up with Bella's panties, before then being made to kiss their feet and thank them individually. The three then changed into more comfortable toga like dresses and Jack was invited to sit naked amongst them on the huge leather sofa as they drank copious amounts of wine and discussed their Corfu excursion. Jack was made to feed the three of them with titbits from a Chinese meal which was delivered later, and with nuts etc. whenever the whim took them. They all got slowly inebriated, until at last, a smiling Bella slipped a shiny collar and leash over Jack's neck and led him upstairs to her bed. Bella had him undress her, then mad e him kneel in the centre of the floor whilst she lay on the bed. "You shall now ask permission to lick me all over; I saw you look at my breasts earlier and I think you could do with mothering; you must ask me nicely and I will allow you to suckle on me for a while, before you worship my womanhood with your tongue." Jack was a little tired after the excitement and exertions of the day; the wine he had been allowed had also left him a little worse for wear, but he yearned to lap at her ample breasts and please her once more; the delicious scent from her panties still locked in his memory, his cock rose once more. "Please Mistress Bella, may I be allowed to worship your body with my tongue?" Bella's pussy tingled with pleasure as she noted an almost pleading tone in his voice. She toyed with her erect nipples as she responded. "Good boy! You may come and keep me warm now." She kissed his hair as she pulled his head to her breast as he entered the bed; she moaned with pleasure as she felt his stiff cock on her thigh as he took her hard nipple between his lips and sucked, teasing it with his tongue before moving on to take as much of the delightful fleshy orb into his mouth as he could. Bella slid a finger back and forth through her moist slit and over her eager clitoris as the equally eager Jack licked, lapped and sucked her mature breasts; his cock slipping against her thigh as he oozed lubrication in his youthful excitement. Bella was ready to be serviced; she would now demand to be satisfied. "You'll lick my pussy now; when I've come, you may lick my asshole. You shall disgrace yourself on my sheets and earn a spanking from Madeline; Marie and I will watch you being spanked for your misdemeanor" Jack did not hesitate and licked his way down her supple belly, his cock ready to explode as he caught the divine whiff of her nicely aroused pussy. She took his leash and pulled it tight to ensure he remembered just who was in charge as he lapped at the delicious flaps of her bulging flower. She moaned deeply and raised her legs high, pulling his face hard against her needy cunt with her free hand. Jack rasped his tongue against her clitoris as she had taught him just a day or so before; his cock throbbed as he rubbed it against the sheets and thought of being allowed to cum whilst licking his mistress's asshole. Bella almost screamed with pleasure and her legs pointed rigidly at the ceiling as she exploded into orgasm; Jack lapped for all he was worth as she moaned and wrapped her fleshy thighs about his head. She then sniggered as she pushed his head down to her spicy asshole. Jack was in heaven as he thrust his cock back and forth on the silky sheets as he probed her hot anus; he truly knew his place in life now, and was in submissive ecstasy. Bella was now enjoying her complete dominance over him and delighted in the warmth of his tongue servicing her asshole with absolute obedience. She would help the thrusting slave cum. "I'll have your cream now; I will so enjoy watching Madeline spank you, she will ensure you know pain, and in front of two other women. She'll allow you to lick her ginger pussy if you take your punishment well." She sniggered triumphantly as she felt Jack convulse; he moaned in absolute ecstasy as his tongue went deep into his mistress's asshole and he spurted gloriously in complete submission to her. He shot again and again as he thought of going over Madeline's thighs for his Mistress's pleasure. Bella laughed scornfully to help him empty his balls deliriously as he humped the sheets with the taste and smell of his mistress's asshole exciting him exquisitely. She pulled on his leash when he had recovered and kissed him sweetly, wrapping her thighs about him, they cuddled and slept. Lucky Jack Learns to Obey Ch. 06 The women took great pleasure in treating him like a small child as they stood around him, their full mature bodies displayed and their excited nipples brushing against his flesh as they all padded him dry. They smiled as his cock stood erect while his balls were towelled dry; each mothering him methodically and purposefully, bringing him down to the required and accepted level, controlled and under their authority. Bella smiled as she carefully buckled his collar, having lifted the white shroud over him once more. "Now we'll go and have a few drinks by the pool while we await the arrival of Zeta; she will be so pleased to meet you." He followed obediently and was made to kneel on a cushion facing the table where Bella and the other women sat drinking, taking great care to ensure their young charge stayed fully aroused by displaying their legs and flaunting their breasts through the thin fabric of the thin summer dresses as they looked down on him and discussed an agenda. Madeline grinned at the kneeling male, crossing her ample thighs and brushing her red hair back in the warm Mediterranean air. "I'm so looking forward to having my cunt licked on the beach; so much hot sand for young Jack to shoot his cream onto; I so love making them masturbate for me in the open air, it makes it extra thrilling." Bella giggled. "I want to take him with me to show him the area first thing tomorrow, then he can have some time entertaining us on the beach." Madeline smiled wickedly. "Of course my maid Alcina will be keen to take him with her to have him fetch and carry when she shops for provisions; she has some friends who love to meet the males who come here, I know she loves to take them to a secluded part of the island and have some fun with them." Marie laughed. "That will be a lovely education for him, the Greek girls so love to be headstrong with a male; they get so little opportunity to be themselves, he will love their attitude toward him." Jack's cock pulsed as the girl they spoke of appeared and sneered at him as he knelt obediently away from the women, his place below them fully emphasised. Jack's cock lifted the shroud rudely as he then noticed someone follow her. A severe looking woman with her black hair up in a bun, a tight black dress showing her curved mature body to full effect, ogled the young man with an air of contempt and licked her bright red lips. Alcina maintained eye contact with Jack; she seemed to know that the women had announced that she would have her pleasure of him too. "Mistress Zeta, Madam Madeline. She is most anxious to meet your friends... and the male trainee." The women giggled at her bold but unnecessary statement of the obvious, though Madeline was equally pleased with her growing feminine authority. The maid faltered as she went to leave and turned to her mistress once more. "Please Madam Madeline, may I be allowed to attend his training at Mistress Zeta's? I would so love to see it." Madeline smiled at Zeta and the stern women intervened, excited herself at the prospect of a younger female showing enthusiasm for domination. "You will be most welcome young lady; I shall show you myself how to use the horse-whip and get the best results from it. I know the male will more than appreciate your efforts." She thanked Zeta, gave Jack another sneer and then almost skipped back to the villa. Jack's cock was now rock hard and his anus tingled with anticipation as the severe woman strutted over to him to give him her full attention. She stroked his hair and ran her hands around his chest, arms and back. "He is a nice young example, and obviously very submissive; he will train nicely and benefit from it." She sat in a chair and eyed Jack with a wicked smile, and undid the top button of her dress. "I am so hot in this outfit, I do wish I'd chosen something else to wear." Bella and Madeline smirked, they loved her routines. Bella stepped over to her and handed Jack's leash to her. "You know which is my room, I have lots of thin summer dresses up there; take Jack with you and have him help you choose one, he can help you freshen up too." Jack was tugged to his feet and went meekly with the stern woman, who did not decline the offer. His cock remained rigid as he watched her rear ascend the stairs before him, she closed the bedroom door and lifted the shroud over his head. "You may undress me now, I want to see how you move; you shall do so at my command the day after tomorrow, and you'll have a little extra encouragement." She smiled as her young charge fumbled awkwardly with her buttons, her cunt tingling as he eventually managed it, and enjoying the feel of his fingers on the flesh of her torso as he eased it over her soft ass cheeks. His balls tingled as she stood facing away from him and calmly put her hands on her hips, letting him study her mature feminine form in black lace panties, her soft scent making his youthful cock pulse with excitement. "You will remove my bra and then kneel and take down my panties." Jack did not hesitate in doing as he was told and shook a little as he eased the panties down her legs, gasping softly as he viewed her magnificent ass. She kept her long legs straight and leaned forward slightly, then placed her elegant hands slowly on each cheek and parted them, showing him her soft asshole. "I hope you like what you see; the next time you are given this opportunity, you will have learned what it is to be truly dominated by a woman, and will have earned the pleasure; your mistress and the other women will witness your worship, which will make your homage so much more pleasurable. I know you want to sniff my asshole, as l know you are truly submissive; you may do so now." Jack's cock dribbled as he gratefully moved his nose into the warmth of her cleft and sniffed at the rich honeyed scent of her asshole; his mistress, Marie and the stern Madeline had shown him authority which had awoken his submissive craving, but the presence of this severe matriarch held him spellbound and under her absolute control. He yearned to be dominated by her, and his wish would be granted in less than two day's time. He knelt in abeyance and sniffed long and hard, dreaming of the discipline and humiliation he would face before being allowed to do so again. Zeta's clitoris swelled, ready for the further treat he would be awarded before they rejoined the other women; she had dominated many males before, but the freshness of younger ones who were truly submissive was a thrill she never tired of. She pulled away and took his leash, leading him to the bed where she had him kneel at its end, and sat before him. She smiled at his erect cock, and gently rubbed the underside of his balls with her foot before gracefully lifting her legs to the bed, spreading them slowly and exposing a freshly shaven cunt. "You shall have the honour of pleasuring me now, while I think of harnessing you and showing you the delights of being whipped into order; I shall then take great pleasure in watching you masturbate for me, make sure you deserve it." She tugged his leash forward and had him sniff her aroused cunt, then pulled his eager face into the delicious moistness of her gaping cunt; the novice submissive almost shot his load as he tasted her sweet essences, he would willingly be disciplined by her and dreamed of what humiliations he would face. He licked lovingly at each fold and flap, and then felt her urgency as his head was lifted to her attend her budding clitoris, she lifting her legs high and moaning with pleasure. He rasped at the nub atop her sweet slit and she groaned and clasped her broad thighs about his head as she elapsed into a delightful orgasm. She panted with pleasure for a short while, before pulling his messy face away and grinning at him. "Good boy! I think you have earned an extra treat." She left the bed and rang the service bell before returning and lifting her legs. "I think Alcina has become wickedly fond of you, I want her to witness you masturbating; you'll lick my asshole until she attends." Jack had his tongue in the sticky pucker immediately, and sampled the tang of the woman who was to thoroughly discipline him under the hot sun the day after tomorrow; his balls and anus tingled with a strange mixture of fear and curiosity, hoping that the maid would be lax in her duty and allow him time to thoroughly enjoy the dominant's asshole. Zeta pulled his head in tight as she too hoped the maid would not be too efficient, also thoroughly enjoying the warmth of his probing tongue. The knock at the door was answered by Zeta's invitation for the prim maid to enter; the mature woman now sitting with her legs crossed. Alcina came over with a broad smile and then looked down on the kneeling male with a sneer of utter contempt. Zeta smiled down at him and passed his leash to Alcina. "Witness the weakness of the male you will help whip into shape in the arena; he will humiliate himself while you watch, and this will confirm your need to dominate him before an audience." She toed Jack's cock and crossed her arms. "You can masturbate now; we would both like to see how you appreciate your betters." Jack went red with embarrassment as the two giggled when he started to stroke his cock, finding it difficult at first, despite his yearning to come. Alcina made his task easier, pulling his leash tight as the stimulation of his cock overcame his apprehension; his submissive side now enveloping him, enjoying the humiliation of their amusement. The haughty maid ensured he would shoot his seed plentifully. "I will so enjoy using the whip on him, and I have some friends who will enjoy watching him shoot his mess just for them when I take him to our special place after going to town. He is going to have a tan all over his body when he goes home, and he will certainly know how to behave when among girls." She pulled tighter on his leash as he moaned uncontrollably and spent his seed in abundance as the women laughed; he gasped as he looked up at the grinning Zeta, his hot cream spurting repeatedly from his relieved cock, in the ecstasy of his humiliation, trickling down the stern woman's shins and ankles. She pointed to her legs as he panted in recovery after his frenzied delivery. "Let your young mistress see how you enjoy the taste of your own seed. Lick it all up now, and be sure to clean every last drop. " Alcina watched with interest as she loosened her grip on the leash and allowed him to lick his salty mess from the dominant woman's legs; she smiled as she saw Jack's cock remain almost fully erect as he enjoyed the humiliation, she knew she would have some real enjoyment from him when she had him to herself, he would know her spite for sure. Zeta had him kiss her feet before she left. Jack helped her into a cotton sun dress, and his shroud was replaced before she led him proudly back to the other women; a drink would now be most welcomed by him, to relieve the salty taste from his mouth.