Appointment by Card Only Ch. 01

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Sissy, Madam, and Sub are thrown together at a brothel.
3.7k words
4.47
34.8k
17

Part 1 of the 7 part series

Updated 06/09/2023
Created 07/15/2014
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She had always been so vulnerable, growing up with the other boys it was so obvious she was not like them. Now in their late teens as adulthood announced itself to the others by adorning them with bodily hair and a developing musculature, they laughed at the soft hairless form of the one who was well known to them, but only from an external perspective. The feminine tendencies peaked within her at this time; she found other boys strangely attractive, and something also stirred within the loins of most of those who were acquainted with the soft boy, though none admitted it openly.

Now pretty faced and with thick blonde hair, her soft red lips completing a girlish face, they would have the sweet one accompany them in their masculine jaunts which apart from the public places like shopping malls included the privacy of the woods and fields which surrounded the town; in a makeshift camp in the woods the large and hairy males would make her strip naked, enjoying her tears as she protested in vain. One by one they would produce their eager and erect cocks as they admired her sweetly feminine shape, and the tearful sissy was made to wank them as they laughed at her.

As they shot their hot spunk it was noted that the sissy's little cock stood firm in its own arousal despite the tears; the sweet sense of submissive pleasure readily growing within her. Having eagerly shot their hot contributions upon her downy legs and soft belly, she was left alone to make her own way home, forced to use her underwear to wipe their sticky cum from her soft flesh. On returning home the weeping sissy would lay on her bed and wank as she thought of those cocks, dreaming of being bound and punished as her almost hairless balls tingled in ecstasy and delivered her sissy cream. Alone in the house, she took comfort in wearing her sister's soft panties and tights, admiring herself in the mirror and wanking several times. On following days the smiling males would knock at her door and she was compelled to follow them across the fields to the camp in the woods, her cock as stiff as theirs.

Now alone in her meagre bedsit, Peter had long become Poppy; apart from those she communicated with on sissy websites, nobody other than those at the benefits office knew her true gender. The softly attractive girl spent what little she had on the pettiest clothes she could afford. Her cock bulged in the snug satin panties as she crossed her legs in girlish fashion and finished doing her nails in pink; her benefit was in the bank account, she would go shopping today.

Madam Ruth Palmer smiled as she looked out from the window of her well-appointed detached residence as one of her maids dusted the shiny stilettos she stood in; the dominant woman cut an imposing figure in her smart and tight outfit, her mature womanly curves and breasts expressing her imposing feminine form magnificently. Her brown hair up in a bun, high cheekbones and lined brown eyes adding to her natural severity. She had rid herself of a weak husband and had set herself up as the madam of an exclusive house for the pleasure of gentlemen and gentlewomen alike. She was always on the lookout for fresh recruits to suit all tastes; often arriving home with younger females who she would sample herself in one of the many bedrooms, her dominance was not gender specific. Though most male submissives would be farmed out to one of her many dominant female employees, she would often dominate male clients herself when one took her special fancy.

She pointed the maid to the door.

'That will be all Lucy, you may keep the bed in suite three warm until I return; if I am unaccompanied you will demonstrate your tongue service, if not you will witness and assist in the submission of a new member of our little family; as with any Saturday I have a good feeling about today.' The maid bowed her head in reverence to her owner and with tingling pussy went to the room. Ruth strutted down the grandiose stairway and sneered with pride at a male servant who waited at the foot of the stairs, on his knees with head bowed.

'Car James! If we arrive and return without incident or hindrance I shall allow you to masturbate at my feet.' His cock swelled as he kissed her feet and then hurried away as she walked to the front door. He arrived with the large black Mercedes from the side of the house as she descended the steps and he eagerly opened the rear door for her.

'The Mall Madam Palmer?' She smiled contentedly at the submissive's servility.

'Yes James, the Mall.'

Bruce Miller dragged himself from his bed, his cock stiff with the need to relieve himself and with the sleepy fantasy he was having about the stern women that excited him. As he emptied his bladder his bleary thoughts returned to the night before when had disclosed to the boss of a company he had done freelance work for, in a drunken stupor, his need for sexual relief. The gratified boss, pleased with the work which had earned him a large contract, had slipped him a card with an address on it. He had simply smiled and tapping his nose had said how this house catered for any sexual preference he may have; it was an up-market business the cost of which would be way beyond his normal financial resources, the card signed by the owner would allow him a gratis session. His cock remained stiff as he remembered the card and searched frantically through the pile of clothes he had worn last night. There it was; just an address with a signature below it, nothing which disclosed the nature of the business involved. The soft aroma of expensive feminine scent wafted from it, making his balls tingle; 'Any preference catered for' he thought to himself.

Poppy's cock stiffened as she gave a leering man a soft smile as he made way for the pretty girl he saw to alight from the bus. She felt his eyes burn into the soft firm cheeks of her arse as it wiggled in the tight dress when she stepped gingerly down to the pavement in her high heels. She never tired of the thrill she got at being so feminine and being out in public as the girl she wanted to be; her sexuality making her even more feminine than most girls, and the soft figure with small puffy breasts she had been blessed with ensured she gave many male onlookers an instant erection. She yearned to be taken like a girl by a strong and adoring male and had come close to meeting some through the websites she patronised but needed to be sure that they would want her long term and not just for sex, it was a difficult situation but it kept her very horny as she lusted for sweet submission to the right male.

She enjoyed the glances and rude smiles as she ascended on the escalator to the upper tier of the mall, her nipples feeling very sensitive and her tight little anus clenching as she dreamed of being held down and having it invaded by a stiff cock; if only her circumstances were a little more favorable, she could then widen her outlook and get noticed by someone she could truly desire. She minced her soft arse past one of the more expensive stores; she was on a tight budget, and then walked back to it with a smile, just looking could do no harm. Her little cock was stiff and oozing in her tight panties as her pink nailed fingers felt the softness of some black lacy underwear; the price was way beyond her means but oh how she would love to have them against her soft white flesh. There was a coffee shop in the centre of the store; from it a stern woman sat with a male who sipped obediently at a glass of water while she sat cross legged and indulged in a cappuccino. Her hawkish eyes watched the delicate sissy lust over the lingerie; her pussy buzzed as she studied the sweet nubile shape and soft blonde hair. She gave James a stern look.

'You wait here and don't speak out of turn to anyone. If you are a good boy I may allow you to sniff my panties when you wank for me; today becomes more exciting by the moment.' James was in no position to disobey even if he could. His cock boned as he watched his Mistress's large and firm arse bustle toward the lingerie section; he hoped that she was very excited as he thought of being allowed to sniff the gusset of her discarded panties as he wanked at her feet. The stern woman casually edged closer to the sissy and deftly sniffed at her soft hair. It was then that she noted that the pretty hands, though still very dainty and delicate, were just slightly larger than she would have expected for a girl of her stature. Expert in the form of both male and female, having viewed so many, her attention then turned to the shoulder width; thought the sissy's arms were very slender and feminine, the bony shape of the blades and collar bones - although softly proportioned - told her it was very likely this was a boy. Her pussy tingled with excitement.

'These garments are so lovely! I really must try some on. I know this is very cheeky of me, but would you mind coming to the changing rooms with me to give your honest opinion on how they look on? I can't get my chauffeur to do it, that would just not be proper; I would be eternally grateful.' Poppy stood with mouth agape for a moment and Ruth's mature cunt was now gaping to match as she took in the soft red lips, large sapphire eyes, and pretty soft face that looked at her. Poppy blushed and felt compelled to oblige; this formidable looking woman had such a presence about her.

'Oh... Oh OK, I err.. don't mind at all, though I doubt I'll be a very good judge.' Ruth took several items from the rack.

'These are exquisite; which ones will you try on?' Poppy blushed again and smiled softly.

'Oh I can't afford... I mean I was just looking, they are so nice.' Ruth was now even more interested; pretty young girls, and sissies, who were not so comfortably off financially were easier to entice, this one was gorgeous and there were many gentleman clients who would pay good money to be entertained by such a delicate flower. She grabbed her hand and squeezed it gently.

'Oh there are so many young people down on their luck at the moment, and I have more resources than I know what to do with; I will make a gift of that bra you like so much if you'll accept? It's not like you need a huge one like me, if you don't mind me saying!' Poppy was reluctant but she would love to own the lacy bra.

'Oh I couldn't, it's very kind of you to offer though.' Ruth smiled as she noticed Poppy's pink nails were still feeling the luxurious material.

'I would love to see it on you, just the same! Come with me and then I'll ask you again; there's no harm in you trying it on.' Poppy blushed again as she took the tiny bra from the rack and the dominant woman held her hand firmly, leading her to the changing booths. Poppy was still a little uncomfortable but this was only a middle-aged lady; what harm could she come too? James looked across with his cock stiff and needing that wank more than ever; he had seen his Mistress recruit young girls this way many times, and this one was very pretty indeed; he hoped she'd be a submissive he could tease and receive favour from when his Mistress was not around.

Ruth's cunt continued to tingle as she led the sissy into one of the larger booths and swished the curtain closed behind them.

'I won't keep you too long, no doubt you have people waiting on you.' Quite innocently, Poppy sealed her fate and Ruth knew she would be keeping her for some time.

'Oh that's OK, I live independently; I live on my own, I like it that way at the moment.' Ruth was ecstatic as she slipped out of her tight skirt and blouse; Poppy couldn't help but look jealously on at her superb feminine curves and ample breasts held firm in a very expensive looking bra. Her large womanly thighs were displayed magnificently in stockings and garter belt; Poppy blushed and turned to look away. Ruth laughed aloud to ease the sissy's embarrassment, but sneered secretly in triumph as she looked at the pretty arse which she would shortly own.

'I know, stockings are so old fashioned, but I find it keeps a man keen and makes up for my age.' She quickly bustled into the new things and touched Poppy's shoulder.

'There! What do you think?'. Poppy turned and gave a gentle smile as she viewed a woman whose body shape she could only dream of emulating; her mature curved hips and full breasts poked magnificently in black lace.

'Oh, you look wonderful!'. The stern woman's cunt tingled as she moved forward and held the sissy's soft arms, making Poppy's little cock tingle along with her anus which clenched as though struck by some strange foreboding. Ruth smiled as she felt the sissy tremble, and released the grip on her; she would hold her completely before long.

'Now, let's see you in that bra!' Ruth turned and faced the other way as the sissy eased her dress over her slender shoulders and pulled off her pink bra, replacing it with the black lace. Ruth turned and looked at the sweet sissy; the tiny bra helped enlarge Poppy's puffy little breasts which barely filled the modest cups. Poppy's balls tingled at the deliciously feminine feeling this bra gave her and Ruth gently eased her to look in the mirror; she saw herself standing next to the formidable woman, so sexy in her lace and stockings. Ruth's cunt bulged as she thought of showing her to her gentlemen clients who were very well-to-do; she would keep her 'intact' and gauge their reaction before deciding her fate; the sissy would fetch a good price as a slave to one of her overseas clients perhaps? She snapped back to the immediate situation.

'See how cute you look! You must have it!' Poppy loved it but was still torn at accepting such a generous gift from an absolute stranger for so trivial a service.

'Oh I... I couldn't, it's so nice but...' Ruth placed one of her expensively manicured fingers on the sissy's soft red lips and smiled. She would now effect the capture of her delicious prey.

'You come and have a coffee with me and then decide; I'll at least buy you a drink for helping me.' Poppy felt obliged to accept a coffee; why not? James suppressed his grin as the two emerged from the booths; he knew the routine so well. His eyes met with those of his stern Mistress; he could tell by her flushed face that her panties would be a delight to sniff as he wanked for her, and this pretty young girl was so sweet. Ruth clicked her fingers as the two sat.

'Two more cappuccinos James.' Poppy jumped at little at the commanding bark which came from the woman who had spoken to her so gently, and her balls tingled all the more as the man she was with bowed his head and went to the self-service counter without question. Ruth smiled and put her hand on Poppy's delicately painted fingers.

'I do so love to have men know their place; of course it's easier when you are their employer as well.' James smiled wickedly as he deftly took the phial from his pocket and laced the left-hand coffee with the substance; he loved the helpless look on their faces as they were driven back to a life of sexual slavery, it increased the orgasm he had earned as he indulged in his own submission to his dominant Mistress. His cock was rock hard as he thought of those panties. He returned and the coffee on the left was placed in front of Poppy; Ruth's cunt oozed in her panties as she watched those soft red lips embrace the small white cup and take in the coffee. Within a minute the large blue eyes dilated, Ruth sneered with satisfaction as Poppy tried to speak but could not manage a sentence. The dominant woman took the black lacy items and hung them over the empty chair behind them.

'I have so many pretty things at home that you will look so much better in; you are such a pretty little thing, and you will be a very popular girl amongst my gentlemen friends.' She put her arm under the table and up the sissy's skirt; Poppy's little cock erected as the manicured hand eagerly fondled it.

'Oh yes, you are very special girl indeed, and we are going to make you even more special.' Poppy stared with a fixed gaze as the two helped her to her feet and walked her to the car park exit; a girl from the store picked up the black lacy lingerie from the chair after they left.

'Some people!'

Poppy was now under Ruth's complete control and could only breath heavily without speaking as the comfort of the car and the warmth of Ruth's caress made her feel so uncomfortable, helpless, trapped. James grinned in the rear view mirror at her glassy stare; he would spunk plentifully with that in his memory. Ruth saw his look and smiled as she worked her panties down her legs, held them up on her shiny stiletto, and then twirled them on her finger.

'You have done very well today James, but you have smiled once too often; I shall have Rowena cane you after you have disgraced yourself at my feet. I will have total obedience from all males.' James gasped and nearly shot his load at the thought.

'Yes Mistress, thank you Mistress.' He drew the car up close to the front door and opened the door for his Mistress and they both helped Poppy from the car. A smiling maid hurried down the steps to take in the new recruit.

'Take her to suite three and tell Mistress Rowena and the other staff to come to the main lounge, James is to be humiliated and punished.' She turned to James, twirling the panties on her finger.

'Park the car James, then go to the main lounge and strip naked; you may then receive my panties and the punishment you have earned.'

James knelt naked and cowering, his cock erect and on display for the delight of the grinning maids and madams of the house; one of which was the strict dominatrix Mistress Rowena. She stood by a low bolstered horse over which James would be caned at her pleasure after masturbating before the female household members. Mistress Ruth strutted into the lounge and walked over to the subservient James. The women grinned as he kissed her feet without the need for the slightest request; he truly knew his place amongst all women and he was in total awe of her power.

'Tell the ladies what you want to do for me today James, then beg for my panties. I want this over with quickly, I wish to go and receive comfort from our new prize. I shall not remain to witness your caning, I am sure Mistress Rowena will administer a thorough thrashing, which is what you deserve for your indiscipline.' The women smirked and chuckled as they awaited the first part of his humiliation; only gentleman clients were afforded any level of respect by the maids and madams, they were all Mistress to male servants, and ritualistic punishment was routine.

'Mistress, I wish to sniff your panties and wank at your feet in honour of your unquestionable dominance. I beg you, let me sniff your panties.' The women laughed and sneered as the naked male was reduced to begging to commit a base act. Ruth smiled with satisfaction as she took the panties and wrapped them about his face, pegging them behind his head. The women jeered as he gasped and snorted through the gusset, his cock bobbing and boning at the intoxicating scent of a thoroughly dominant woman's cunt and arsehole; a thin line of sticky pre-cum dribbled down from his bell-end, delighting the women. Ruth stood dominantly over him as he wanked frantically, snorting eagerly at the sweaty gusset as his hand stroked his bone-hard erection; his submission was complete as he moaned and convulsed, bringing rapturous applause and taunting from the women as he spurted thick loops of hot semen in humiliated ecstasy. Ruth pulled the panties from his head and pointed down to her black stilettos down which white blobs of warm spunk dribbled. He licked his own spunk from her shoes gratefully.

The women applauded again as Ruth walked off to suite three to receive her own pleasure, and Mistress Rowena looped a choking leash over the humiliated male's head and led him on all fours to be caned on the bolstered horse. Two maids gleefully bound his ankles and wrists to its legs, and he was soundly thrashed by the spiteful ginger haired dominatrix, Mistress Rowena. The women laughed as the adult male was quickly reduced to tears, wailing like a child as his exposed and lifted buttocks were striped red-raw. His submission soon overtook his pain and the women applauded again as he enjoyed a second humiliating but satisfying orgasm, brought forth by the savage application of the ginger domme's cane.

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