Jimmy and Winnie Pt. 01

The scream froze Jimmy's blood. Winnie was always so polite and quiet. He never imagined that she could scream so loudly. Or that she could scream for so long. Most importantly, he never imagined that she would find him hiding in her wardrobe.

Not that he gave it that much thought. It was never a great plan to begin with. Just hide in her wardrobe and watch her undress. Unfortunately once the idea entered Jimmy's head he could not leave it alone.

He had to hide in her wardrobe. He had to see her naked. At least a glimpse of Winnie getting dressed in the morning. He already watched her get up early every morning and waddle to the bathroom through a narrow crack in his slightly opened bedroom door. Then he watched her waddle back after her usual bathroom routine. But then the door closed and that was the end of his voyeuristic adventure. There was no key hole to spy through, the solid oak door closing the view of Winnie's possibly naked body inside. So when he saw the giant wardrobe in her bedroom he knew that it was the best way to achieve his aim.

Jimmy grew up very alone. His father was a good man, but he was also very strict. It was the only way he knew, how to bring up children. They were Puritans and that meant there was very little pleasure to be enjoyed at their household. Jimmy's mother was sickly all of Jimmy's life and she would often spend long times away in sanatoriums and hospitals and hospices and other places of healing. That was the main reason that Jimmy's father relied on help. Live-in help.

There was an elderly woman called Heddy living with them for most of Jimmy's life. She was recommended through the church as a good, God fearing woman and she tried to instil the same thinking in Jimmy. When she passed away, a little over six months ago, his mother returned home from one of her sanatoria stints and tried to run the household, but in just a few months she was sick again and had to return to her sanatorium to recuperate.

Jimmy's Father looked for new people, but the church group matured, and there were no convenient live-in servants to find. He advertised in the paper and after a short interview he decided to hire Winnie. She was nothing like Heddy. Although very religious, she was more evangelical than puritan. She was also black. In her early thirties, she was much younger than Heddy and had a much different outlook on life. Still, she came highly recommended through a legal friend, and that was enough for Jimmy's Father. When he first met her, he was not sure if she was the same person that was recommended, but then he never was a very good judge of people. Still, he trusted his legal friend's recommendation enough to hire her. Looking past her strange clothes, her strange walk and her not so pretty face, he could see that she attended church, was a hard worker and could do her chores without constant supervision. Exactly what he needed.

When Winnie was born, she had a problem with her pelvis and her legs, that her mother could not afford to get fixed and so she would waddle like a duck from side to side when she walked. Even more so, because one of her legs was slightly shorter than the other.

After puberty her hips and breasts swelled up and drooped, her eyes bulged out and her skin broke out in pimples that left scars on her face. She was not pretty by anyone's definition and she knew it. Growing up, her mother prepared her for her lot in life, by telling her that she was not really the marrying material and that she would be better-off looking for a job as a housemaid or a cleaner rather than finding a husband or a more ambitious career.

Winnie was ever-so-grateful to her mother for those words, because instead of looking for fulfilment by marrying the first man that came along, she started working as a cleaner and was very happy with her lot. After more than ten years of cleaning offices at night, she managed to find a job as a housemaid which meant daytime hours and a much cleaner work place. This was her third placement as a maid and for the first time, it was a live-in housemaid with a real live family.

Her previous job was a lonely one. She was looking after a huge mansion that was managed by a bitchy private secretary on behalf of a multi-millionaire that was slowly dying in a hospital. After five years of cleaning the multistorey mansion that was already clean, but had to be re-cleaned to satisfy the bitchy manager, the millionaire finally died, the house was sold and she, the gardener and the cook were all let go. Working for a family and living with them was a good change for the loneliness of the work at the empty mansion.

She liked her new family. She liked Jimmy's Father when she first met him. He scared her a little with his stern demeanour, but she could tell he was a good man. She was not sure about Jimmy. She liked him when she first met him, but he was always a little withdrawn and she found it hard to engage him in a conversation. She was always a good judge of people and was confident that one day she will find what makes him tick. She will learn how to communicate with him. She knew that these things could not be rushed with some people.

It was different for Jimmy. When he first saw Winnie, he was mesmerised by her. It was hard to tell what made Jimmy that way. Heddy tried to put the fear of God into Jimmy, but Jimmy was made of a different cloth than his Father. Or Heddy. He was a loner and a thinker and he had rich imagination that kept him company through the lonely growing up in the quiet household. School was ok for him and he managed to go through it with no close friends and no social life.

Studying in his second year at the local college at the age of nineteen, he still respected his Father's wishes and would return home straight after classes. He did not drink alcohol, so there was no point to be tempted by going out with his classmates anyway. There were many pretty girls around him at the college but he was unable to ask any of them out. The fear of saying some corny line or getting rejected or humiliated was worse for him then the pain of loneliness. Especially because he would re-live the humiliation in his mind thousands times over and over afterwards. Then there was the fear that the incident would be reported back to his Father and the one main aim in his life was for his Father to be proud of him. Yet the more he tried, the less he felt he achieved it.

So when Winnie appeared at their house, he was besotted. He did not see her physical shortfalls. Her wobbling gait, her misshapen torso, her bulging eyes, her high forehead and her scarred skin. None of those flaws, flaws that prevented Winnie from securing a good husband, seemed to have bothered Jimmy. He did not see her multi-coloured, multilayered dresses as anything other than an opportunity to watch her take some of the layers off when the days warmed, exposing more of her fascinating body to him. In fact her strangeness encouraged him. He felt that she was a lot closer to his "class", than any other girl he ever met. Not social class or racial or any other classification other than beauty. Not that Jimmy was ugly or malformed or crippled in any way. Not physically, but internally, he certainly felt that the girls at the college were well above his "class".

Not that he was considering marriage, dating or even casual sex with Winnie. When Winnie appeared, with her shy and quiet demeanour, her misshapen body and her strange multi-coloured clothes, all he hoped for was to see her naked body. He was waiting for an opportunity to glance her dressed in her night clothes, or leaving the bathroom wrapped in a towel, but her night clothes were always covered by a thick dressing gown that protected any details of her body underneath. So were her trips to the bathroom in the mornings and evenings. So a month of watching Winnie sleep in the room next to his, he was no closer to seeing her naked body then when she first moved in.

All that changed with the sight of the large double door wardrobe in her bedroom this morning and the idea to hide inside it.

The plan worked at the beginning. There was enough room to hide inside. The partially opened door also let him observe the bedroom very clearly. When she walked back into her bedroom and removed her dressing gown he could finally see her night dress. They were equally thick and buttoned up flannel pyjamas. Still Jimmy watched her move about through a narrow crack in the wardrobe doors. Even with the thick pyjamas hiding her body, he did notice the free movement of her large and now unsupported and pendulous breasts, freely swinging and moving under her pyjama top. He was also lucky, because she did not need to go to the wardrobe to prepare her clothes for the day. They were all hanging over the back of a chair and he could just watch her lay them out on her bed. The success of the venture, her freely swinging breasts under her pyjama top and the excitement of the voyeuristic episode he was just experiencing were enough to make Jimmy's cock stiffen up and demand freedom from the containment of his pants.

The need to adjust his pants and to stroke his hard cock was just too much for Jimmy to resist. He attempted to reach into his pants. Unfortunately all movement within the large wardrobe, full of clothes, resulted in rustling and creaking noises. Noises that caused Winnie to stop laying out her clothes for the day and to investigate the source of the noise in the wardrobe. That very quickly led to Jimmy's discovery and Winnie's scream of fright.

After the blood curling scream, Winnie's fright turned to surprise.

"Master James, why are you in the wardrobe?"

But her surprise did not last long. It quickly turned to anger. She was often the target of teasing and jokes from the handsome white kids at school. She was always embarrassed about her misshapen body. That was why she wore her many colours and the many layers of clothes. She hoped it will distract from people looking at her. If they laughed at her clothes, it was something she controlled. They were laughing with her. When they saw her physical deformations then they were laughing at her and she had not defence against that. That was her basis for her anger. Anger that found a sudden and quick outlet.

"Are you spying on me?"

"You want to see what the freak looks like?"

"You wanna take pictures?"

"Publish them for your friends to laugh at?"

She released her pent up bitterness on Jimmy in a torrent of accusations. Internally she realised that she was feeling violated and almost assaulted by Jimmy's presence in the wardrobe. She did not expect this type of behaviour in this household and definitely not from Jimmy. She did not expect it from the young man.

Jimmy was unable to speak. The discovery, the scream and now the torrent of accusations sent his head into a spin and stopped his brain from functioning. At best he managed to shake his head in the negative, hoping that it would explain to Winnie that he had no intention of causing her such distress. They stared at each other, Jimmy unable to speak, Winnie waiting for an answer until the moment was broken.

"Winnie, are you alright?" the heavy silence hanging in the room was broken by a knock and a deep voice from behind the door. It also announced to both of them that Jimmy's Father also heard the scream and had come to investigate. Winnie was about to tell him to walk in to see his son caught 'in flagrante' but one look at Jimmy's face made her change her mind.

Jimmy was not having a good time since the scream. He was completely speechless and he never felt so scared in his life. The scream made his blood turn to ice and his throat dry up. When Winnie levelled all the accusations at him, he was completely speechless and at best was able to shake his head in the negative as a feeble effort to defend himself. When the knock at the door announced his Father's arrival, he knew that all was lost and that his life was about to end. He knew he would not be able to face his Father and that he would rather die than wait for that door to open and for his Father to see him hiding in Winnie's wardrobe. It was this complete panic and hopelessness that Winnie saw on his face and it made her change her mind about what to do next.

"Come in," she announced to the door, but she also quickly closed the wardrobe doors hiding Jimmy inside and out of sight.

"Are you OK Winnie?" Jimmy's father asked, his voice reserved but concerned, as he opened the door, but stopped in the doorway. He saw her only in her pyjamas and was far too prudish to enter the room any further.

"Sorry Mister Kelly, I saw a big spider run under the wardrobe. I got a big scare."

"Spider?" he made a motion to step into Winnie's bedroom, but his prudishness won over the need to rescue a damsel in distress by seeking out and killing the spider. He stopped.

"From the scream I thought you've seen a ghost," Mr Kelly shook his head.

"Well as long as you're alright," he was about to close the door but stopped again, still a little suspicious, but keen to leave her bedroom while she was not fully dressed.

"Have you seen Jimmy this morning?" he asked as an afterthought.

"Jimmy? Yes I saw him earlier today," she stammered a little. Glad that she did not have to lie to her boss. She did see him this morning, just a few seconds ago in her wardrobe.

"He said something about running," Winnie continued. That was also true, although he said it almost a week ago and in a totally unrelated conversation.

"Running?" the Father was surprised, "Well it would do him some good to get some exercise," then he closed the door and walked away, his steps echoing down the corridor, confirming his departure.

Winnie opened the wardrobe again. Jimmy was standing there, white as a ghost, with tears streaming down his face. He was the man given pardon before a firing squad. The firing squad with fingers poised on triggers, told to lower their guns. But now the guns were again at the ready. The finger again on the trigger, but at least it was just Winnie. Suddenly the shock of being found by Winnie was a lot less scary than being discovered by his Father.

"What are you doing here?" she asked again, this time a little less angry. A little less accusatory. Jimmy's mind was starting to work a little better now. Truth be told, he was not sure what his motivation was. He did want to see her body. Her naked body. At the age of nineteen, he felt he should see at least one naked woman before he died. It did not occur to him that maybe he should ask the person first. He did not think that girls were even interested in showing off their bodies. How greatly he misunderstood the fashion industry.

"Did you want to rape me?" she asked and saw the shock in his eyes before his head shook in the negative.

"Did you want to have sex with me?" she asked again, the anger and the voice another notch softer. She saw him again shake his head in the negative, but his eyes betrayed his thinking. She could see that he was now considering it in his mind now.

"Did you want to watch me undress?" she asked and his non-response was proof enough to her that she hit the jackpot. This was something new. This was different. Here was a very handsome young man, although a little socially awkward, wanting to see her body. Not in a nasty way. In an obviously sexual way.

Winnie was not innocent. She knew men and she had sex a few times in her life. Never for a relationship. Just for pleasure, for sexual satisfaction, for relaxation. Not often. Not with many men, but she certainly was not a virgin. Her last partner was the gardener at the mansion. He was a lot older than her, but she enjoyed sex with him. Jimmy here was different. He wanted to see her naked. Not as a freak show. Because of sexual attraction. Her anger was no longer anger. It was sexual excitement.

"So you wanted to see me undress?" she concluded from her interrogation, not needing Jimmy's verbal confirmation. His face betrayed the fear he felt from being discovered. And exposed.

"Why don't you go watch your girlfriends undress?" she asked, carefully watching for Jimmy's reaction.

"I don't have any girlfriends," he announced, his voice barely audible. She nodded.

"So what do you think is a suitable punishment for hiding in people's closets? Waiting to see them undress. Waiting to see them naked." He shrugged his shoulders in response. He did not know what to say.

"I have the perfect solution," Winnie announced. "We turn the tables around. You undress for me?" The fear returned to his face as he shook his head in the negative. The very idea freaking him out.

"Oh, that is OK. I can just call you father back. Let him think of a suitable punishment." The reaction was immediate. He reached up to his shirt and started unbuttoning it.

"That's better," she said, as she settled down on her chair, watching the spectacle. Soon the shirt was off and she saw that although his skin was pale and white, his body had some natural muscle definition. She realised that it was a first time for her to watch such a handsome young man undress. Undress just for her. She was starting to feel her excitement build up within her, as she slowly shifted from her commanding and condescending tone to one of sexual desire and lust. She was certainly starting to enjoy herself as the familiar warmth and wetness spread between her legs. He had to take off his shoes and socks before he could take of his trousers. Standing in his underwear, he stopped, looking very dejected and feeling extremely vulnerable and embarrassed. He realised just why Winnie was so upset when she found him in her wardrobe.

"I said undress, not tease me," she said in her best commanding voice. "Off with the lot." She said as no longer teasing him with her voice. It was filled with lust. Feeling extremely self-conscious and mainly afraid that Winnie would laugh at the size of his manhood, Jimmy refused to move. Still, the situation had caused him to become aroused and the shorts he wore were not good at hiding his growing erection.

"So you're not going to go all the way?" she said in mock seriousness. She stood up and slowly walked up to Jimmy. He was taller than she was, but her eyes completely dominated him. She stopped in front of him, placed her hands on his hips and as she knelt down she pulled down his underwear. Free of the restriction of his shorts, his cock jumped up and swayed from side to side in its semi-erect state.

"Well," Winnie announced, kneeling in front of Jimmy, his cock swaying from side to side only inches from her face. "Maybe this requires further investigation." She grabbed the base of his cock as Jimmy inhaled his breath from the shock and the immense pleasure he felt. It was the first time he felt anyone else's hand on his cock and the feeling was the best he remembered.

The gentle pumping action her hand started over the base of his cock was at first so slow it was almost painful, but his cock stiffened and her hand started to move faster and faster. He knew he was not going to last long. Winnie knew it too. She stopped. Then it happened. The engorged purple head of his cock, dying for the same love and attention her hand was giving to his shaft, was suddenly touched by a soft, wet, and of so hot tongue as she slowly took his full head into her mouth, and pushed his cock deep into her throat.

Winnie hated sucking cock. In fact it was the first time she took a cook that deep into her mouth. She rarely gave head jobs to her partners, preferring their cock in her pussy, but this felt very natural and very exciting for her. Her usual sexual encounters took place on a bed, in the dark. Each partner free to imagine the other looking better than reality. She did not mind. She knew she was not that special and she knew that her partners were there because neither were they.