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Jenny's World - Mike's Trial

Jenny’s World – Mike’s Trial

Mike stood looking at himself in the bathroom mirror, an older face, decorated with a well-kept salt and pepper beard looked back. He had always considered himself to be a handsome man, but that was part of his overall arrogant demeanor. His abundance of confidence had carved him out a good career, rising to the position of district manager in his former company. He spent the following years abusing the authority of his position to coerce many women into sex, and that had now finally caught up with him.

He walked with his lawyer back to the courtroom where his trial was beginning. The same women that he had leveraged all those years were now suing him for it. This was it, it was going to be the end of his life, and he knew he deserved it. Back then, it didn’t seem like such a big deal. There weren’t any women in higher management positions, so he helped a lot of them get there in return for a little sex. Despite the deep regret he felt now, Mike still remembered each of the women vividly.

There were a lot of women Mike pressured into it over the years, all with their special treats, but he held the first one and the last one as the dearest. The first was a beautiful blonde woman by the name of Charlotte, around his age at the time. She had arrived at her interview prim and proper, her hair tucked neatly into a bun. Charlotte was one of two final candidates for the position, with the other being a male. Mike remembered exactly how he expressed the difficulty of his choice to Charlotte and how she pleaded her skills and work ethic, and how she would do anything. The extra money was going to mean a lot to her, her husband, and their kids.

“And what did Mike ask you to do in order to secure the promotion?” The opposing lawyer asked Charlotte as she sat on the witness stand.

“He told me I had certain qualities that the other candidate didn’t have, and that I should use them if I wanted the position,” she answered with a distressed tone.

“What qualities were Mike referring to?” The lawyer asked.

“He was referring to my body,” she answered, her voice stressing more now. “He said that my tits and pussy would guarantee my promotion.”

“And did you accept Mike’s offer?” The lawyer asked.

“I did,” Charlotte stated.

“Why did you agree to this?”

“My husband and I were having financial trouble and the promotion came with a large pay raise. I kept my husband and kids in mind the entire time Mike had his way with me.”

“What do you mean by financial trouble?”

“We were behind on our mortgage and car payments.”

Mike felt immense shame as Charlotte answered each question, hearing for the first time how she experienced their encounter so many years ago. Her point of view was completely opposite of his own, where he remembered charming her into some fun. He remembered the warmth of her body and how she closed her eyes in pleasure.

“Mrs. Charlotte, isn’t it true that your time with my client my consensual?” Mike’s lawyer asked.

“He leveraged his authority over me,” she answered.

“Did you tell Mike, at any point, before, during, or after that you didn’t want it?”

“I did it for my family,” she protested.

“Did you ever tell him no, Mrs. Charlotte?”

“No, I didn’t, but it doesn’t mean I wanted it.”

“Did my client tell you at any time that you wouldn’t be promoted if you denied his offer?”

“He said it would help.”

“Mrs. Charlotte, you stated a few minutes ago that my client told you that this arrangement would guarantee your promotion. Isn’t it true that you accepted his offer for your own benefit because you didn’t want to leave it to chance? Isn’t it also true that you willingly used your so-called qualities to your own benefit?

Mike felt a strange sense of relief and guilt after his lawyer finished questioning Charlotte. Of course, he didn’t want to be painted as some rapist, but he never intended for any of these women to feel the way they do. He continued to hear their stories over the next few days as they called witness after witness. The opposing lawyer set each one up to paint Mike as a villain, then his own lawyer always seemed to reel it back in.

By the end of the week, the plaintiffs rested their case and Mike was surprised that only about half of the women he had propositioned were called. His lawyer explained part of it but insisted that it was better if Mike didn’t know all of the details just yet. Mike sat around all weekend, worried about what the week ahead would bring. His lawyer apparently had quality witnesses that would appear on his behalf, but Mike wasn’t so sure about any of it.

On Monday morning, Mike’s lawyer began calling witnesses, several of which were women he had made the same deals with. Again, Mike felt ashamed, this time because of the arousal he experienced as he recalled his time with each of the women as they testified. He remembered how he had them on his desk or in his chair, or sometimes even in his car. Each day seemed to crawl by slower and slower, and though much of the testimony was in his favor, Mike wasn’t sure if he wanted to be let off too easily. Maybe he did deserve some punishment for everything.

“The defense calls Jenny Clayton-Mclean.”

Mike felt a spark of excitement at the sound of Jenny’s name. She had been the last woman he ever tried to bargain for sex, and it was because of her refusal that made him realize he needed to change. Still, Jenny had been his all-time favorite employee, solely due to her skills and work ethic. Her physical beauty just happened to be a perk. He watched Jenny walk down the aisle in her high heels, wearing a modest skirt and blouse, her long brunette hair loose and flowing. Mike was happy to see her, not because she was obviously testifying on his behalf, but because he genuinely missed her.

“How do you know my client, Mike?” The lawyer began.

“He used to be my boss at our former company,” she answered.

“Did Mike interview you for a promotion during your time there?”


“Did Mike offer you a promotion in exchange for sex?”


“Did you accept his offer?”

“No, I didn’t,” she answered, looking at Mike.

“But you did get promoted, correct?”

“I did, yes.”

“How did you get your promotion?”

“I went back to Mike’s office a few days later and demanded that he recognize my skill. He promoted me to a higher position than what I was originally training for.”

“Have you ever had sex with Mike?”

“Yes, but not until over a year later.”

“Can you tell the court about it?”

“We were at an annual company party that ended late one night. My car wouldn’t start, and Mike offered to drive me home after the tow truck took the car. I invited Mike into my home, and we had sex.”

“Why did you have sex with Mike that night?”

“Because I had found him attractive from the first time we met.”

“If you were attracted to Mike, why didn’t you have sex with him for the promotion?”

“I was going to, but then I realized I preferred to be promoted based on merit, not my body.”

“Were you assigned as a female at birth?”

“No, I was born as a male.”

“Why do you identify as Jenny today?”

“I still don’t understand it all, but I was forced to change my body to save my life.”

“When you were still a male, do you recall having a belief that women had it easier?”

“I did sometimes, yes.”

“Since you fully identified as a woman by the time you met Mike, and had all the physical capabilities of a woman, why didn’t you take advantage of the situation?”

“I truly considered it at the time,” Jenny began. “If I had done it, I wouldn’t have ever known if I could’ve gotten promoted just from my work.”

Mike felt a comforting warmth as he listened to Jenny speak, happy that he selected her for the job. At the same time, he remembered how willingly she invited him in that night and the way he fucked her over her own sofa. Her pussy had been so wet, hot, and tight. He still couldn’t believe she used to be a male.

“Mrs. Mclean,” the opposing lawyer began.

“You’re married to Skylar Mclean, is that correct?”


“Is it true that you have an open relationship, meaning that you and your husband have agreed it’s okay to sleep with other partners?”

“That’s a very basic way to say it, but yeah, we do sleep with other partners at times.”

“Is it fair to say that your best friend, Andy, is your most active sexual partner apart from your husband?”

“That is fair, yes,” Jenny answered, feeling uncomfortable now.”

“Isn’t it true that you leveraged sex against Andy shortly after your transition? When he refused to be your boyfriend, didn’t you withhold sex from him?”

“That isn’t true,” Jenny answered, trying not to panic, wondering how the lawyer knew so much.

“Mrs. Mclean, isn’t it also true that you’re much more susceptible to sex after drinking alcohol, and that you had been drinking the night you slept with Mike?”

“I slept with him because I wanted to,” Jenny protested.

“Isn’t it true that you had sex with several men at a party after becoming intoxicated?”

“Those men raped me,” Jenny declared with anger filling her voice.

“Mrs. Mclean, you were on video willingly engaging in sex acts.”

“I was drugged by a substance called throb,” she responded, trying to keep her eyes from forming tears.

“You’re referring to a drug that circulated in the news for a while that supposedly makes women want to have sex. Are you aware that several studies disprove this drug’s effectiveness?”

“It altered my mental state. I wouldn’t have ever willingly done those things!”

“Which things, Mrs. Mclean? Didn’t you bring a guy home from a club one day just to take his virginity? When you were on your honeymoon, didn’t you have sex with another couple? Haven’t you willingly engaged in the same sex acts numerous times with different men?”

“It isn’t the same thing!”

“Isn’t it true that Mike took your shirt off during your final interview before you told him to stop?”

“Yes, he did,” she answered, feeling her will breaking away.

“Didn’t Mike see and touch your breasts during this time?”


“You say that you were promoted on merit, but isn’t it possible that this encounter was enough to put the odds in your favor?”


“According to your Instagram, Mrs. Mclean, you have almost five million followers. Isn’t it true that you regularly upload risqué content for all of your followers to see?”

“I upload a variety of pictures and videos.”

“Isn’t it true that you use your body to make thousands of dollars a month on Instagram by posting, and even more from sponsorship deals?”

“I create a lot of fitness content or showcase different clothing brands or even video games.”

“Mrs. Mclean. Even before you began receiving income from social media, you accepted money for your body, isn’t that true?”

“No, it isn’t.”

“Do you recall receiving five hundred dollars at your friend Andy’s bachelor party in exchange for showing yourself?”

“That was a game!”

“You were the only woman present at the party and you accepted payment for the guests to see you naked.”

The lawyer presented slideshow evidence to support his line of questioning, containing many pictures of Jenny from her Instagram, many of which left little to the imagination.

“Mrs. Mclean, why did you appear on a national tv broadcast?”

“Because I was the first person to experience what I went through, and I wanted to bring attention to it to help others that might be going through the same thing.”

“How many Instagram followers did you gain after that segment aired?”

“I’m not sure.”

“According to available data, you gained several million followers over the months following that broadcast. A boost in popularity and fame that has helped you increase your income. Mrs. Mclean, you’ve told this court that you denied Mike’s offer because you wanted to advance on merit, but everything you’ve done since then has involved using your new body to get ahead.”

“Redirect, your honor,” Mike’s lawyer said as he stood, then paused to give Jenny a few moments to regain her composure. “The opposing counsel has tried painting you in a bad light due to some ventures that would normally be considered lucky. Why did you leave your previous employer?”

“I was fired,” Jenny answered.

“Why were you fired?”

“I was fired for telling my story on tv. They said it was too much of a distraction.”

“Did you apply for other jobs following your termination?”

“Yes, but no one would hire me.”

“Do you recognize the item in this exhibit?”

“Yes, that is a diary I kept when I first got home from my transition.”

“Would it be a fair assessment to say that a lot of what was written early on details your extreme dislike of the change?”

“Yes, I thought the change was the worst thing to ever happen back then.”

Mike was unable to sleep that night due to how bad he felt for Jenny. Whether he won or lost the case didn’t matter to him now. His life had been made public and all of his indecencies had been exposed. Now, the only woman he tried to do right by had her life picked apart because she came to defend him. He thought about calling or texting her to apologize, but the damage had already been done. He found Jenny’s Instagram on his phone and was happy to see she was living a good life.

To Mike’s surprise, Jenny was in the courtroom again on the day of the verdict. Everyone and their voices were a slow blur as he was ordered to pay a list of damages to each of the plaintiffs. This was a good thing, he thought. He knew he deserved it, and it was about time he was held accountable for his actions. His mind wandered as the courtroom dispersed, not paying attention to anything or anyone while walking out and down a hall to the bathroom. He didn’t come back to reality until a soft voice called his name in the parking lot.

“Mike,” Jenny said, standing nearby.

“Jenny,” he said, smiling at her. “I saw your story on tv, I still can’t believe it.”

“It’s a long story, but it’s all true,” she said.

“Maybe if I’m lucky enough, I’ll get to hear it someday,” he said.

“Why don’t we get dinner, and I can tell you about it today,” she said, smiling.

Mike didn’t understand why Jenny would want to have dinner with him, but he gladly accepted her invitation. He had been staying in a hotel for the trial, so he didn’t have much to wear in the way of clothes. At dinner, Mike filled Jenny in on everything that happened since his departure, then Jenny did the same when it was her turn.

“Those idiots should have promoted you, not fired you,” he said.

“I appreciate that,” she said.

“I mean it, Jenny. You were truly my favorite employee,” he said with a sigh. “You did great work.”

“What’s wrong?” She asked.

“You’ve been put through so much because of me,” he answered.

“I’m not worried about a few stupid questions from a lawyer. I know my worth,” she said.

Jenny went on to tell Mike all about her illness and how she went from being a guy named Jason to a woman named Jenny. Having had sex with Jenny himself, he knew full well that she had all of the right parts. The story itself was one of the most unbelievable things he had ever heard, yet he was sure Jenny was being truthful. When the checks came, he insisted on paying for her meal, then felt a slight tug in his chest knowing that he’d probably never see the girl again.

“It was really good to see you again,” he said as they stopped at Jenny’s car.

“It was nice to see you too,” she said, her cute mouth smiling widely.

Mike looked over Jenny’s soft, pretty face, committing it to memory since it was time for him to turn around and leave her. Instead of turning, though, their faces drew closer and closer until he kissed her. He waited for her to jerk away or protest, but that moment didn’t come. The kiss became deeper and more intense until he mustered the willpower to pull himself back. Jenny looked at him with her bright brown eyes, her mouth still slightly open. He recalled the words in the courtroom, that Jenny found him attractive, and that she was in an open relationship. These two revelations made Jenny seem more within reach. He looked into her eyes, regretful that he had ever done her wrong, and happy that she stood up to him back then.

“Why did you agree to be a witness for me?” He asked.

“I only told my side of the story,” she answered.

“There has to be more to it than that,” he said.

“Maybe, but,” Jenny danced around a bit, cold. “We should talk somewhere warmer.”

“We can do that,” Mike said, noticing how Jenny’s outfit was intended to be cute, not warm. “Do you have a place in mind?”

Mike arrived back at the hotel where he was staying, and Jenny parked beside him. Even after all of these years, she still didn’t fall into a category he could anticipate very well. She was young, smart, and driven, all attributes he found attractive.

“Now, tell me why you really came to court,” he said when they made it to his room.

“That’s easy,” she said. “You made offers to all of those women, including me, and we all had a choice. Maybe you’re guilty of something, but not this. That’s my opinion, anyway.”

“You are an amazing woman, Jenny,” he smiled. “They were idiots to fire you.”

“I know you wouldn’t have let them fire me,” she said, smiling back at him. “Here we are, though.”

The ice and awkwardness between them slowly dissipated and Mike eventually began to ask Jenny more about her true past, to which she happily answered. It was until over two hours later that they realized how much time passed. Mike was only in town for a couple more days and intended to use that time to visit some relatives and old friends.

“Did you really mean it when you said you almost took my offer that day?” He asked.

“I was close, yeah. It seemed like an easy decision, but then I didn’t want anyone to see me that way all of the time,” she said.

“Do you know my second biggest regret with you?” He asked. “That I didn’t take my time with you the night you invited me in. I was sure you were going to change your mind if I took too long.”

“We have all night, tonight,” she smiled.

Mike felt his dick instantly jump to life at Jenny’s direct comment. Now that the door was open, he moved close to her, using his position and leverage to lean Jenny back as he kissed her again. He took his time, kissing her lips and neck, his hands touching all the areas of her body he had missed before. She was soft, curvy, and in perfect shape, her hair long and thick. He undid her blouse, surprised to find that she didn’t have a bra on.

“I decided to stop wearing them,” she smirked, noticing his surprise.

He mouthed her nipples, teasing them both with his tongue and teeth while his hands worked her skirt. Soon, Jenny was wearing nothing more than stockings, which Mike left in place. He pressed his mouth to Jenny’s womanhood and put all of his attention forward. Each of Jenny’s little ticks and ques prompted Mike to adjust his speed, angle, or pressure, depending on how she moaned or squirmed. It wasn’t going to be like last time. Tonight, he was going to take his time and enjoy everything she had to offer.

“You’re really good at this,” Jenny moaned.

“I’ve learned a few techniques,” he responded briefly before continuing.

Mike made sure to closely follow Jenny’s body language, then as she began to breathe heavier and squirm more, he focused on remaining steady. No matter how much Jenny moved and bucked, he held his position and continued the pattern with his mouth and tongue. Watching Jenny cum was not only the highlight of his day but the best moment of the year. He loved the sound of her voice letting out moans of pleasure and loved the way she arched her back while in the throes of her climax.

Not expecting any reciprocation, Mike was surprised when Jenny switched places with him. Even though he had successfully gotten into the pants of many women, he never had any of them give him a blowjob. Having this young, absolutely sexy brunette willingly suck his dick was like winning the lottery. She was shy about it either. She was noisy and messy with it, her mouth warm, wet, and hot, making erotic little sound effects. He took hold of her hair, pulling it to one side so it didn’t obstruct the view of her magnificent skills.

Jenny mounted him next. She took her place on top, then positioned his throbbing dick against her wet pussy before sitting down on it. Her insides were just as tight and wet as he remembered. The excitement of it all made it difficult for him to not blow right away. When he was no longer able to will away his orgasm, he stopped Jenny from moving. Instead, he turned her over again, kissing and licking her skin while giving himself a rest. He couldn’t get enough of her soft, smooth skin and tight body, especially her sizeable perky tits and tasty nipples.

“I have a confession, Jenny,” he said while kissing along her stocking-clad leg. “I’ve been in love with you for years.”

Before Jenny could answer, Mike moved between her legs again, his hips lining up with her body to allow his dick to penetrate her. He tried to read the reaction on her face, curious to know if she held any feelings for him in return.

“You shouldn’t be,” she responded, even as he fucked her.

“Do you feel anything for me?” Mike asked, taking his time.

“I don’t feel the same way,” she answered.

“Then why did you hook up with me before, and why now?”

“Because it’s fine and it feels good. It was exciting to fuck my boss.”

“I’m not your boss anymore.”

“It still feels good,” she said, adding in a soft moan.

“Now that you’re here in my life again, I’d rather not leave and never see you again.”

“You know where to find me,” she said.

The thought of Jenny offering him future sessions was enough to ramp up pleasure beyond limits. His motions became quick and rough, transitioning the soft sound of sex to the loud sound of his body clashing into hers. Mike grunted his imminent orgasm and pulled out, triggering Jenny to quickly sit up and move her mouth to his cock. The first spurt hit her face before she managed to put her mouth around him. Jenny looked so perfectly sexy and erotic while swallowing his cum.

Mike woke up sometime in the middle of the night with Jenny sleeping peacefully beside him. It was a remarkable feeling to have a young woman in his bed. He wondered if things had been different, could he and Jenny have ended up together. Maybe if he didn’t force himself on her in his office that day, he could’ve courted her into a proper relationship. The ring on her finger could be his and he’d be able to experience her shining personality and physical beauty every day and night.

An hour later, Mike was still awake, his mind processing endless hypothetical circumstances. On the way back from the bathroom, he noticed Jenny’s phone light up with a notification. His curiosity won over logical judgment, and he picked up the phone to look at it. The phone displayed a standard lock screen which awaited Jenny’s fingerprint. A dark excitement rose deep inside of Mike, knowing that a great deal of Jenny’s life was a single screen away from his viewing. Again, curiosity and excitement won over and Mike began pressing each of Jenny’s fingers to the screen.

The phone unlocked with relative ease, giving Mike a view of Jenny’s social media apps, text messages, phone logs, and image gallery. He got back into bed, figuring that if Jenny woke up, it would be easy for her to assume she left the phone on the bed. Her phone logs weren’t exciting at all, but her social media was miles better. There were dozens of incredible pictures of Jenny clothed or showing lots of skin. There were even many pics that Mike was sure pushed the boundaries of the site’s rules. Even so, pictures did little justice after being able to touch and taste nearly every inch of her in person.

He browsed her gallery next, swiping through what was almost identical to the pictures on her social media. However, having had secrets himself, he was fully aware that the phone had a secure folder somewhere. Once he found it, he scanned Jenny’s finger again, then was presented with quite a treasure trove.

There were hundreds of pics and videos that were obviously very personal. Jenny’s expression in the pictures was filled with love as she took these topless selfies. There were videos of her masturbating, showering, painting her nails, talking dirty, and trying on different lingerie. Only a few days ago, there was a video of Jenny sucking a man’s dick from his point of view. The video was several minutes long, ending only after the man pulled out and blew his load on Jenny’s face. This particular album was all videos of her engaging in sexual activities with the man.

Another album contained similar activities, but Jenny appeared to be with a different man this time around. At the end of one video, Mike could hear Jenny moaning to Andy that she was going to cum. A third album contained nothing but clips and pictures of Jenny’s pussy dripping with cum, and a fourth, contained facials. Every video had one thing in common, which was that the man had been recording with Jenny’s phone. He could feel his dick creeping to life again at the idea of Jenny liking to be recorded.

Mike grabbed his own phone now, guilt already burning at his conscience. His cock swelled into a full erection and arousal clouded any remaining good judgment. He placed the phones next to each other, allowing Jenny’s albums to copy to his own phone. Jenny stirred a bit, rolled over, and continued to sleep quietly. When the galleries finished transferring quite a while later, he snooped into her text messages. The most recent thread was with Skylar, who he knew to be her husband.

“Let me know the verdict,” one message said to Jenny.

“I will,” was sent back, followed by, “guilty.”

“I’m sorry to hear that.”

“I’m gonna get some food with Mike, maybe more,” Jenny said.

“It’s a long drive, so don’t drive home if it’s dark,” Skylar replied. “Hope you enjoy yourself!”

Another recent text message was with a guy named Andy, who Mike figured was the other guy from the videos. A lot of the texts were normal, some even nerdy, which surprised Mike, but then there was also dirty talking and sexting. Andy sent dick pics and other nudes, and Jenny did the same. One thing that seemed to be a normal pattern was a new pic of Jenny’s feet and toes every time she had a new style or color. The further back Mike went, the more apparent it became that Andy had a foot fetish. Jenny had sent him many pictures that either included her feet or focused on them. He went back and checked that particular gallery, and sure enough, there was a video of Jenny giving Andy a foot job.

When morning came, Mike decided that he wouldn’t instigate any further sex with Jenny. He had enough content to last him a long time once he got back home. Jenny did instigate it, though. She returned from the bathroom, then kissed him while her hand reached for his dick. Then, just as Jenny was about to dive under the blanket, Mike said,

“Do you think we can record it?” Jenny hesitated and looked at him. “If you want to,” he added.

Soon, Mike was recording Jenny with her own phone, knowing that he’d be added to her hefty library. It felt as if he were being inducted into the hall of fame, one of three men documented on Jenny’s phone receiving a blowjob. He continued to record as they moved on to sex.

“On my face,” Jenny instructed when Mike was about to finish.

He did just that, pulling out in time to release his seed over the girl’s perfect face. It covered her lips, nose, and eyes, and even got in her hair. When all was said and done, Jenny sent him a cloud link to the video and told him not to share it with anyone. They kissed for a final time at the door of the motel.

“I love you too, Mike, but I’m not in love with you. I’m here waiting if you’re ever in town again.

As Jenny drove away, Mike didn’t know if he’d ever see her again, let alone have sex with her. He had other duties and obligations to attend to at home, and those would prevent him from visiting Jenny. Now, his night of fantasy was over, and it was time to face the harsh reality of real life where he was in debt to pay damages to the women he had wronged.


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