Revenge is Sweet

by sexy_jessie


Henry Stewart was thirty five years old, married to a very attractive woman who'd given him three kids, he owned and ran his own very successful computing company in San Diego, "Stewart Computing", meanwhile he owned a large house in the wealthy small town of River Falls. All in all, Henry was very content with the hand life had dealt him. He was very dedicated to his work and part of the reason for Stewart Computing's success in the past few years had been his dedication and the extra hours that he continually put in. Henry was worried that his extra hard work would disappoint his wife and kids, but instead his wife, Sadie, was one of the people who particularly encouraged him to put the effort in; She would tell him how his hard work was ensuring such a good life for her and the kids and it would be selfish of them to demand more from him. Every time he got home late after the exhausting two-hour drive from San Diego, Sadie was there to welcome him with a big hug, dressed often in some of her particularly sexy lingerie and seemingly desperate for sex. These evenings, Henry liked nothing more than to eat out his wife's pussy which seemed to have been given a delightful warm taste from the anxious time that she spent waiting for him. On those late evenings home Sadie seemed so instantly horny and aroused she would often leap on top of him almost as soon as he came in the door, Henry had no idea what the kids would think if they were still awake. Sadie made such passionate love to him on these evenings that the weekends when Henry tried to instigate sex himself were often limp and lifeless and soon Henry and Sadie were left with just sex on these late weeknights. Not that Henry was complaining, these nights were the best sex ever in his marriage, the normally timid Sadie was turned into an animal who took total control in bed and Henry loved it.

One normal Friday afternoon, Henry had told his wife that he would be working late again and not to expect him back until later in the evening. However by 3 PM, Henry realised that he could find nothing left for himself to do at work and so decided it would be a nice romantic surprise to get home early for Sadie. Excited about the idea he hurried home, the highways were much emptier at this time of day, stopping only to buy a huge bunch of pink roses, Sadie's favourite flowers. Henry pulled his Lexus into the driveway of his large modern house. It felt a little bit abnormal, coming home during the daytime, the sun was shining on the house as Henry got out of the car, and Henry couldn't help but feel a little uncomfortable at the unusualness of his early arrival home. He paused for a moment before the mahogany door of his house for no reason particularly other than perhaps to compose himself a little before unlocking the door. The house was unusually quiet, he looked through the rooms on the ground floor, the kitchen, living room and dining room, nobody seemed to be around. Going into the kitchen he filled a vase with water and unwrapped his roses and put them into the vase. Maybe Sadie wasn't home, maybe she had gone shopping. He had just begun to climb the stairs to the second floor of his three storey house when he heard a noise coming from his and Sadie's large bedroom. She obviously had been too distracted to hear him come in and Henry decided to creep up and surprise her. As quietly as he could he padded to the door-of their bedroom and flung it open to greet his surprised wife.

"Honey, I'm home," Henry began to say before stopping mid-way, a step inside the door. His wife certainly was surprised, but not half as surprised as Henry himself.

Sadie was lying on their bed totally naked, her head thrown back and her legs spread wide. In between her legs, Henry could seethe naked, athletic body of James Stone, their neighbour. James' hands were on Henry's wife's shoulders as he levered himself to thrust further and deeper into her pussy. Her legs were splayed wide open and waved in the air. Sadie was clearly enjoying herself, her small pert breasts stood out proud and erect and she involuntarily moaned in pleasure even as Henry entered the room.

A flush of red crossed Sadie's normally soft face, partly embarrassment, partly anger as she pushed James from between her legs. James looked even more abashed as he sat back and pulled the duvet from the bed to cover his shrinking erection. Henry stood just inside the door, mouth open in shock, unable to speak or even to move for a few seconds so Sadie spoke first:

"You're not supposed to be home for three hours," she said, stalling the obvious as James started to pull on his pants and shirt, Sadie remained sitting naked on the bed.

"I took the afternoon off," was all Henry could think to say, "I wanted to surprise you."


Sadie moved out with their three kids. Brad, Abigail and Brock, and stayed with her mother just outside River Falls until Henry could get himself an apartment in San Diego where he planned to move permanently now his marriage was breaking up. Over a lengthy discussion later in the evening of that day, Sadie had come clean and revealed how she had been having various affairs throughout most of their marriage. During the long days when Henry would continue to work late, Sadie would be bored and consistently found her sexual needs uncared for by her husband. She had been sleeping with James, who was also married, on and off for the past twelve years (exactly the age of Henry's youngest son Brock who was blessed with a muscular, masculine physique far more similar to James than Henry himself). Sadie planned to move in permanently with James who was separated from his wife. Henry was devastated but found things had spiralled so far out of his control that there was nothing he could do. After her continued infidelities, Henry knew he could no longer stand to live with Sadie, but he was very distressed about it. More than anything though, Henry wanted revenge both on Sadie herself and on James Stone, the guy who had enticed his wife away.

It was a Friday evening, a week after Sadie had moved out and the large house felt curiously empty of people with Sadie and the three kids all absent. Henry was sat in the room that he had shared with his wife until very recently. The king size bed felt way too large for one and the large room with Sadie's wardrobes still full of so many clothes that she hadn't been able to take away in her mother's little car was a constant reminder of her slender body wrapped in the sexy lingerie Henry loved so much. He opened the drawer to her dresser, it was still mostly full of all manner of different styles and colours of lingerie. He noticed one of his particular favourites, a pink silk teddy. She had worn it when he had got home the Monday before he found her with James, they had made passionate love that evening and Henry now realised that Sadie must still have been horny from James' earlier attentions. Henry now knew the reason why Sadie would be far more passionate on the evenings that he came home late from work and this knowledge was an even greater blow to him. He took the teddy from the drawer and held it to his face, hoping to catch some essence of his departed wife from it. The smell of her delicate feminine perfume lingered slightly over the teddy, Henry enjoyed the touch and feel of the soft silk against his cheek. He had always wanted Sadie to keep some lingerie on as he fucked her as he had always loved the sensual feel of it between his body and hers, a feeling that was now gone for good.

Suddenly, a thought occurred to Henry, a desire to feel the silk lingerie closer against his body. Slowly and carefully he padded across the soft bedroom carpet and drew the blinds closed ensuring not a tiny space of light could be seen through the thick canvas. Then he stripped out of his jacket and tie, throwing them onto the bed. Becoming more excited now he struggled free of his shirt and let his pants and boxers drop quickly to the floor. He now stood totally naked, his exposed cock already twitching a little in arousal as he carefully picked up Sadie's pink teddy from where he had laid it down on the bed and stepped into it. He slowly slid the sensual silk up his legs and pulled the straps up over his shoulders until he felt himself wrapped in the sexy lingerie. His slight frame had always been pretty much the same size as Sadie's and the teddy fit perfectly aside from a clear lack where her chest would be and a growing bulge of his erect arousal at the touch and feel of the pink silk. Although he had always loved women in lingerie, Henry was a little surprised at how excited he was wearing it himself. A drop of pre-cum stained the crotch of his lingerie as instinctively he lay down on the bed and reached his hand down to jerk himself off. Not bothering to remove the lingerie he simply stroked his ever expanding cock through the soft, sensual material. The feel of the silk lingerie between his hand and his cock made him more aroused than he could have thought and soon, without warning, his cock exploded and he blew a huge load of cum all over the inside of his wife's sexy lingerie.

Henry lay back on the king size bed and basked in the joy of what had just happened, never before had he achieved such an orgasm without Sadie's considerable assistance and the feel of the silk lingerie on his body still felt so sexy that he didn't want to remove it and move on from this moment. He looked down at his slender body in the sexy pink teddy and was almost convinced it could have been Sadie's own body, anxious to please him dressed in his favourite lingerie. Suddenly, Henry was struck with another thought, he knew how he could get his revenge on James and Sadie. A dirty smile came to his face at the thought of it and, as he felt his cock twitch with arousal once again, he reached down to jerk himself off once more through the cum stained silk.


The next day was Saturday and Henry arrived relatively early at the house of Naomi Stone, James' estranged wife, he was a little nervous but knew he needed help if his plan was to work and who better to help him than the woman who James had abandoned to go off and have his many affairs. Since their separation, Henry had become better friends with Naomi, for some reason even before he had found James annoying, and over the last week Naomi had been particularly friendly in trying to help Henry get over his wife, especially after learning James was involved. This was why Henry thought Naomi would be willing to help with his plan. James knew that since separating with James, Naomi had enjoyed a lot of sex with both men and women and her open mindedness meant there was another reason why Henry saw fit to trust her with his plan. Despite all this rational thought. Henry was still a little nervous about what Naomi's reaction would be as he stood waiting for her to come to the door, dressed in large, baggy sweatpants and a sweatshirt. Naomi opened the door to him wearing an ankle length black skirt and a dark red halter neck top. Naomi was a black woman, almost six feet tall, with shiny black curls and large breasts that her halterneck barely contained. She ushered Henry into her living room.

"To what do I owe this pleasure, Henry?" Naomi asked as she sat down in a leather armchair and motioned for Henry to do the same.

"I've thought of a way to get back at James and Sadie," Henry said, remaining standing, "But I need your help."

Naomi's eyes lit up at this and she smiled at Henry, "Anything I can do to help," she said.

Henry was drawing the thick, heavy curtains of the living room so people couldn't see in, Naomi looked a little confused but did nothing to stop him.

"Are your daughters in or likely to be back soon?" Henry asked.

"No," said Naomi, still a little confused, "They're spending the weekend with James."

With the knowledge that they were the only ones in the house and that nobody could see in from the street, Henry felt safe to reveal his plan to Naomi.

"Sadie plans to live with James from now on," Henry began and Naomi scowled, "But we both know that your husband can't keep his hands to himself," at this Naomi nodded, "So what we need to do is to catch him in the act with another woman, causing Sadie and him to break up."

"But how are we going to do that?" asked Naomi, "Where can we find a woman to do that for us?"

It was this that prompted Henry to reveal the final, all important, aspect of his plan. He was standing in the centre of the living room, still dressed in sweat pants and a sweatshirt. He kicked off his shoes and hurriedly, much as he had done the day before, undressed, throwing the baggy sweatshirt and sweat pants onto the sofa behind him. Naomi looked understandably a little taken aback at what he was wearing underneath. Henry's clothes were so baggy to disguise that beneath them his body was covered in Sadie's lingerie. Henry was dressed in a sexy black lace basque trimmed with red silk and a matching black and red suspender belt supporting expensive black silk stockings. Naomi appeared wide eyed with amazement at Henry's outfit, but after a few seconds something inside her clicked and a grin spread across her face.

"I've never seen this side to you Henry," she smirked as Henry flushed red with embarrassment, "So, I suppose your plan is to seduce James yourself? I should warn you that I don't think my husband swings that way."

Henry blushed even more at this knowing that he didn't either and that was something that he had to resolve, 'That's why I need you Naomi. I need your help in making me a woman sexy enough to make your husband stray away from my wife."

Naomi's eyes glinted with pleasure at the opportunity and potential this offered her and at that moment Henry breathed a sigh of relief knowing that Naomi would offer all her assistance and help to him and not reveal his secret and embarrass him in front of everyone. Naomi stood up and walked over to wear Henry stood in his wife's lingerie.

"Don't worry Henry," she said, grinning saucily, "We're going to have a lot of fun with this."

With that she took his head in her hands and pulled him towards her planting a passionate kiss against his surprised lips, Pulling away she smiled at him as it was his turn to look wide eyed in surprise.

"Well that beard's got to go for a start," Naomi winked, she looked down and saw the bulge of his quivering cock beneath the black lace lingerie and smirked again, "You're not just dressed like this for your revenge are you?" she said, "You're enjoying this aren't you?"

Before Henry could say anything to answer, Naomi had pushed him to the floor, obviously very turned on by the situation herself as she pulled his black lace lingerie aside to allow his erect cock to spring free before pulling off her skirt to reveal her bare, shaved pussy as she wore no underwear beneath it. Henry had little time to take this in before Naomi lowered her pussy onto his cock and began to fuck him. Henry had little possibility to do anything himself as Naomi took total control, riding his cock until, spurred on by the sexy feel of his lingerie, Henry blew his load up into her pussy.


It was two weeks later and Henry Stewart had now moved out of the old house in River Falls where Sadie had moved back in with James and now lived in a spacious luxury apartment on the outskirts of San Diego far closer to where his computing firm was based. Although he still concentrated on working hard during the day at the office, he no longer stayed after hours or took his work home with him. Instead, back at his luxury apartment, he ceased to be respectable, successful businessman Henry but instead became sex kitten Helena. Naomi had helped him perfect his physical appearance and had come over to the apartment each weekend and some evenings to help him become more alluringly feminine in every way that he acted. Naomi had even ensured that the decor of his new apartment was appropriately soft and feminine with plenty of soft pink colours and a big comfortable king size bed, along with a huge wardrobe fall of Helena's sexy clothes that far dwarfed the tiny, plain wardrobe of Henry's suits. Since leaving the house in River Falls, Henry was no longer able to wear Sadie's lingerie and so, with Naomi's help and his own computer skills, they had ordered him a huge new variety of feminine clothes and especially the sexy lingerie he so loved over the internet. Naomi had further insisted that around the apartment in the evenings he had to remain as Helena all the time in order to fully perfect his femininity. By this point, two weeks after he had first worn his wife's lingerie, Henry was feeling fairly comfortable in his girlie form as Helena and, although he had never left the apartment dressed like this, he felt he was becoming increasingly ready for the time when he could go to a bar and entice James away from his new-found fidelity to Sadie. The one thing that preyed on his mind was a worry about how he would have to convincingly passionately kiss James in order for Sadie to catch them together and break it all off with James. Henry had never thought sexually about another guy and wasn't sure whether he would be up to doing this.

It was about seven in the evening of a springtime Friday and Henry was sat on his crimson velvet sofa, just lounging, enjoying the sight and feel of his feminine look, Naomi had had full length mirrors installed in the living area and Henry's bedroom so he could admire himself and note where he was going wrong with his girlish mannerisms. He had not just shaved off his beard (which had excited some comment from his colleagues) but had completely removed all of his body hair so his skin was now smooth and silky all over. His previously masculine legs, now so smooth and hairless, had become long, thin, sexy girlish legs that he stretched out before him as he stretched back on the sofa. The slender elegance of his legs was enhanced by the six inch heeled sandals he was wearing, he was learning to walk in the tallest heels he could and he admired the sexy effect that they had on his calves. Besides these heels, he was dressed in a short leather mini-skirt, he didn't want to cover any of the length of his new legs he loved so much. Besides, he knew that James would admire the sexy, skimpy clothing on him almost as much as he loved it on himself. He was also wearing a large, billowy white blouse that was very thin and airy and through which his black lace bra (stuffed with very convincing internet purchased silicone breasts) was clearly visible. After Naomi's extensive tuition he was able now to apply his own make-up and had done so today in a simple, understated manner with a little pink lip-gloss and some dark eye make-up and mascara to lengthen his lashes. His hair was still fairly short and masculine and so Naomi had given him a blonde wig with little wisps of hair that curled seductively over his blue-green eyes, besides the fact that it made him look far more sexy and feminine the wig also destroyed the last vestiges of anything that might make James suspicious and recognise him.

There was a quick rapid knock on the door and Henry uncurled, cat like, from his sumptuous new sofa and tottered over to the door in his six inch heels. Naomi stood on the doorstep, sexily dressed in a knee length crimson coloured skirt and a figure bugging tight black top, she was carrying a large hand bag and strode into the room without greeting Henry. Henry shut the door behind her and followed her into the living room where she dumped the bag on the floor and dropped onto the sofa. Henry sat down on another chair and demurely crossed his legs in the feminine way that Naomi had taught him with his hands placed in his lap. Naomi smiled at him for the first time and said:

End of part 1

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