top of page

Jenny's World - Jenny's Coming Out

Jenny’s World – Jenny’s coming out

The show.

Jenny always made it a point to keep her transition secret, except for the few people in her life that did know about it. Once upon a time, this secret was only known by her parents and best friend, Andy. It then extended to her human resource department, her friend Leslie, and eventually, her current husband, Skylar. As more people learned about it, Jenny found it increasingly difficult to keep it secret. Rumors were constantly growing in her job, and her efforts to remain exiled from her extended family were taking a toll. Her parents covered for her with aunts, uncles, and cousins, making them wonder why they haven’t been able to see or talk to her.

Skylar noticed Jenny’s growing concerns over the last few months as people seemed to poke into her life more and more. Just last week, her Aunt Maggie called several times in an effort to speak with her favorite nephew, Jason. Maggie still had no idea about the transition, so Skylar decided to take the call and pose as Jenny’s former self. Skylar could tell how taxing it was for Jenny as they worked together to make the call believable. That night Skylar set the mood in their bedroom for a massage, which was something he loved to do. It gave him access and time to run his hands all over Jenny and enjoy every bit of her perfect body. He used this time to quietly discuss her concerns, and Jenny was able to talk it out while having her stress relieved at the same time. Skylar’s words encouraged her, giving her the confidence to decide it was time to stop keeping it a secret.

With Skylar’s help, Jenny was put into contact with a popular talk show where she could tell her story. They were intrigued immediately, offering her a segment so long as she could provide supporting documents, like medical records, photos, etc. Staff from the show came out later to interview Jenny and everyone that could corroborate her story, including Skylar, Andy, and her parents.

Skylar, Andy, Leslie, Alice, and Jenny’s parent’s all flew out for the day of the show to give support. Jenny sat nervously in the back of the studio while a lady touched up her face with makeup as another guy explained the flow of the segment. Jenny’s parents were introduced on the stage first as an opening to her life. Pictures were displayed from Jenny’s toddler years through the present day, with her parents sharing their stories.

When it was time for Jenny to enter, she walked on the stage in a short black, shape-hugging dress and open-toe heels. It was Skylar’s favorite dress of hers since he loved the contrast of the black against her pale skin. Her fingers and toes were recently tailored with French tips at the salon, which she had visited with Leslie as usual. Jenny took a seat next to her mother on the stage and crossed her legs as she intentionally diverted her attention from the live audience. Instead, she focused on the host while looking back and forth to her parents.

Jenny could feel the eyes of the audience on her, judging her from a distance, forming opinions on her appearance and whether or not her story was true. Her mother even glanced at her daughter’s attire and wished that she had worn a dress that didn’t stop so far above her knees. She didn’t plan on scolding Jenny on t.v., but it was definitely something she intended to speak about after the show, even if Jenny was a grown, married woman.

The host began the conversation, which distracted Jenny from wondering how many people were in the audience, and from the arousal growing within from having so many people looking at her. After hearing Jenny’s account of her forced transition, the crowd burst into cheers of support. Jenny’s eyes filled with tears from the overwhelming sensation of all these people cheering for her. Her mother pulled a tissue from her purse, something that Jenny never got into carrying, nor did she own one.

Skylar entered the stage next, then took a seat beside his wife before holding her hand in his own. This brought comfort, calm, and encouragement to Jenny, making her feel like she could conquer the world. This was it for her; her story would be distributed to the world, no more secret life, no more hiding her past, and no more being ashamed. It was a culmination of every obstacle she had overcome to this point. She thought about the others still undergoing treatment for the same thing and hoped this would help them too.

“Now for the final question,” the host said. “Your transition was much different than what a normal person would expect, is that correct?”

“Yes,” Jenny answered, nodding.

“I’m sure the audience and viewers would like to hear about it, and I believe this is the main reason for your trip to the show,” the host said.

“It is the main reason, yes, and I definitely want to share,” Jenny said. “I’ve already explained how it came to be, but what makes this different is that my body has produced all of the appropriate female anatomy and reproductive organs.”

“So, what you mean to say,” the host said with a smile. “Is that you have ovaries, female genitalia, and the works?”

“I have it all,” Jenny said quickly, wanting to claim her own story. “Everything works just as if I had been born a girl, I have a monthly period, and I can even get pregnant.”

“Pregnant!?” The host emphasized for effect. “Do you and Skylar plan to have children?”

Jenny and Skylar looked at each other with a smile, their fingers embraced firmly in the other’s hand, then they both looked at the host. “Yes, we do,” Jenny answered.

Jenny’s nerves were running high after the segment ended, and the four of them exited to the back once more. As Jenny stepped into the bathroom to wash her sweaty hands, her mother came in to speak to her. The mom held her eyes on her daughter, making sure Jenny felt better about having the opportunity to fully shed her secret. She then looked down upon Jenny’s short dress, which she left little to the imagination.

“You really shouldn’t wear such exposing outfits in public,” she said to Jenny. “I’m no prude, but certain things should be kept between a husband and wife,” she added.

“Come on, mom,” Jenny protested as she dried her hands. “You scold me for showing a little leg, but it was okay when I told you Skylar took me to a nude beach resort.”

“That’s different,” the mom countered. “You weren’t on national t.v.”

“I’d argue that being completed naked everywhere I went for an entire week is worse, but fine,” Jenny digressed.

Back in the guest area, everyone was waiting for Jenny, each person taking a turn to give her a hug. Andy met her first, embracing his best friend with due support but keeping it appropriate since her parents were around. Andy, Alice, Skylar, and Jenny were in a perpetual open relationship with each other, which they kept a secret. However, with Jenny’s back to everyone, Andy copped a feel of her butt as he lowered his arms away from her, which caused Jenny to give him a light punch to the chest.

Jenny’s father stepped in next, smiling at his daughter as he hugged her tightly. It had taken from the time of Jenny’s transition up to her wedding for him to shed the resentment he had of losing a son, and now, he couldn’t be more proud of having such a brave daughter.

Skylar stood back, wanting to be the last to approach his wife, so Alice went next and gave Jenny a quick but thoughtful hug. The only thing she didn’t like about Jenny was the fact she was married to Skylar, whom she had a tremendous crush on. If it were in her power, Alice would swap places with Jenny in an instant, making it so Jenny would be married to Andy, and her, to Skylar. After all, they had a lot more common as they both worked in law enforcement, and Andy and Jenny had their love for video games.

Leslie was next, who now realized she was the only person there without a significant other present. Having flowing blond hair, bright green eyes, and a model's physique, Leslie could easily find a guy to settle down with, but she still preferred making adult content and keeping her options open. After she hugged Jenny, she stepped back again and kept sneaking looks at Jenny’s dad. She loved his salt and pepper hair, the mature look of his stubbly face, whose recently shaved beard was already starting to grow back, and how tall he was, standing at least six foot five.

Skylar approached his wife now that everyone else was finished. Jenny watched his eyes as he walked up to her, with him being the only person who could make her feel both vulnerable and confident at the same time. Skylar’s eyes glanced down to take in all of his wife’s perfect body, from her thick brunette hair down to her cute, pedicured toes. They embraced each other, Skylar’s warm body and clean scent making Jenny relax. On the other hand, Skylar felt the excitement rush to his groin, which caused his cock to spring to life in his pants. He kissed Jenny’s forehead, then her cheek, before kissing her mouth. The group watched momentarily until Skylar and Jenny’s tongues rushed to meet each other.

That kind of kiss is what Andy longed to have with Jenny right now, and he would have to wait until they were back home before he could have her. Alice shared a similar thought, except that she believed Skylar was too good for Jenny. She didn’t hate Jenny, but Alice always had the underlying feeling that she was superior due to being a natural-born woman.

The hotel was only a few minutes away from the studio, so the group headed back to await their flights the next day. Each couple had their own room, and Leslie had a room to herself. This was to her advantage since she still wanted to put on a cam show for her fans. Leslie prepared the room the best she could, then began the show with some talking and answering questions as she often did. Eventually, as tips came in to meet goals, she undressed and treated her viewers to an erotic sexual display.

Jenny’s dad was one such viewer, having watched Leslie’s shows for over a year since he heard Leslie mention it to Jenny. He sat in the hotel room chair, watching Leslie on his phone and listening with earbuds while his wife lay reading in bed. Nearly an hour later, he could feel the ache of his erection begging for release as Leslie reached her third orgasm of the show.

In the room adjacent to her parents, Jenny looked down at Skylar, her hands on his firm chest, her legs on either side of him, and her pussy stretched tightly around his cock. Jenny maneuvered her hips slowly to not make too much noise and alert her parents to them having sex. Both of them had gotten worked up on the show. Jenny, due to all of the eyes on her, and Skylar, because of Jenny’s black dress. Not only did the dress show off her curves, but it also stopped halfway down her thighs, which left her legs exposed. On top of that, it was low-cut, so it showcased her cleavage nicely too.

One more room down, Andy and Alice also lay in bed. The same black dress that worked Skylar up had the same effect on Andy as well. Unfortunately, Alice was still sulking over the fact that she hadn’t met Skylar before Jenny; this way, he’d be married to her now, rather than to Jenny. Despite their respective marriages, Alice had used Andy’s attraction to Jenny to her own benefit. She had carefully crafted the plan for Andy to get time with Jenny under the guise of protecting their own marriage. In turn, Alice was able to get time with Skylar. The plan had succeeded better than she could’ve hoped, and now the four of them were in an unrestricted open relationship with each other.

In the morning, Jenny’s parents insisted on breakfast with her, just the three of them, before going their separate ways on their flights in the afternoon. Jenny made sure to wear something modest so she wouldn’t be scolded by her mother again. All enjoyed the time they spent together, but even though Jenny’s outfit wasn’t in question, her mother did question, as always, why Jenny didn’t carry a purse. She went on about the lack of pockets on women’s clothing and that a woman needed to have essential items with them at all times.

After breakfast, the three left the café, and since the ladies were going purse shopping, Jenny’s dad decided to head back to the room. He met Leslie in the elevator, who had come down to eat breakfast in the hotel lobby. Her blond hair was still damp from an obvious morning shower, and her strawberry scent filled the small space of the elevator. The spaghetti strap tank top she wore, along with her hot pants or booty shorts, as some called them, was enough to get the blood flowing in his loins. It was just last night that he had watched her strip down, touch herself, then eventually fuck herself with a dildo. Now that he was standing there next to her, it was hard to imagine this Leslie was the same one from that explicit cam show.

Leslie looked down at her phone, checking her messages and responding to some of her favorites. This also gave her an excuse to avoid looking at her best friend’s dad, whom she had developed a crush on over the years, even with minimal contact. In response to his “Good morning,” Leslie said, “Good morning, Mr. Clayton,” then continued to stare at the device in her hand.

The elevator emitted a ding when it reached their floor, and Mr. Clayton offered Leslie to exit first out of chivalry. To his benefit and weakness, he watched the blond walk down the hallway as her hips swayed and soft thighs swished past one another. His dick was solid in his pants, round two from his lack of release last night. Leslie stopped in front of her door, struggling to retrieve the keycard from the tiny pocket of her shorts. He passed her again, getting another nose-full of her soft, strawberry aroma as he thought about the vivid images of her shaking in her climax.

“I enjoy your shows,” Mr. Clayton stated in his deep, mature voice.

“What shows?” Leslie asked, completely oblivious to the fact that he might be talking about her cam shows.

“Well,” he said, then paused momentarily. “The ones you do for a living, I believe.”

“Oh,” Leslie almost gasped as the realization dawned on her. “You watch them?” She turned to face him now.

“Not all the time, but often enough,” he answered. “I watched the one from last night, and it was certainly magnificent.”

Leslie felt a tear in her emotions. On the one hand, she had a good feeling Jenny’s dad just needed a little nudge, and he’d be all over her, but on the other hand, she didn’t want to betray her best friend. Even as she considered her options, he walked back down the hall toward her. He was much taller, by at least a foot from what she could estimate, one of the things she was attracted to about him. Another thing was his dedication to style. Leslie knew he had only gone to breakfast but was wearing a neat button-up shirt complemented by a matching vest.

“Where are Jenny and Mrs. Clayton?” Leslie asked.

“They went shopping, so I came back here since they’ll probably be a while,” he answered casually, even as his hand brushed several strands of her damp, blond hair.

“Oh, okay, “Leslie managed to say as she experienced a level of nervousness she had never felt with a guy before.

Mr. Clayton looked down at her, his eyes drinking her face and beauty as if she were a cold glass of water in the hottest desert. She felt like a deer in headlights, having been made speechless by a guy for the first time when she had always been the one to wrap them around her finger. She tensed up as he moved his hand to her side, expecting a touch or grope, but he took the card from her hand, scanned it, then opened the door.

The magnetism of their lust drew them close together when the door closed again. Leslie arched her back as Mr. Clayton leaned in; his hands placed themselves on her waist, then they kissed with a quick close of the gap between their height. Leslie found his kiss to be skilled and experienced, one from a man that knew what he was doing. Mr. Clayton found Leslie’s to be soft, sweet, and youthful, her mouth at least thirty years younger than his own.

He picked Leslie up with a strong but gentle motion, then sat her on the bed a few feet away, the same one where she had put on such a sexual display last night. Today, her pleasure, moans, and orgasm would be caused by him. He loosened her shorts and pulled them down her soft legs before tossing them into a chair in the corner. Her panties were removed next and were subject to the same treatment.

Leslie felt her hormones and arousal flare into high levels of poor decision-making, which were the kinds of decisions that would make her fuck her best friend’s dad. She watched him drop down in front of her, then pulled her body to the very edge of the bed so he could reach deep between her legs. She felt his mouth move to her pussy, his lips and tongue beginning a slow but purposeful technique of extracting pleasure and moans from her. This was much different from a guy her age excitedly lapping, sucking, and biting with no clear direction. This finely aged man knew what he was doing, from every flick of his tongue, every nibble of his lips, to every maneuver of his finger, which had now slid inside her.

Mr. Clayton was beyond aroused, his cock more erect than in years. Leslie’s skin was so tight and soft, her womanhood cleanly shaven with folds that layered into perfection and a clitoris that crowned the design like a jewel. He paid the strictest attention to how Leslie responded to him and learned everything that increased or decreased the flame in her loins. Once he had the patterns committed to memory, he was confident that he would make her cum very soon. Just before the ten-minute mark from when he started, Leslie began to verbalize her pleasure. “Oh my god,” “fuck,” and “don’t stop” sprang from her mouth. Her fingers clutched his head with anticipation as he pushed her past the point of no return, his oral skill tugging that orgasm out of her body with authority.

Leslie moaned and writhed with the hot waves of climatic pleasure rippling through her from head to toe. This was the best head she had ever received in her life. Mr. Clayton stood once more as the afterglow took hold of Leslie, and she reached for his pants now, making quick work of them as he had done her shorts. She sat forward on the bed and engulfed his waiting dick, but he stopped her after only a minute or so.

Mr. Clayton would have loved to enjoy a blowjob from Leslie, but he knew their time was limited. He wanted to feel her tight, young pussy, knowing this would likely be the only chance he’d ever get. As they moved to the bed, he placed himself between her legs and soft, creamy thighs. This was his favorite position, so he could look at her face and take in her eyes. He couldn’t help but feel some regret as his cock slid into Leslie’s much younger womanhood. Never in all his years married to Mrs. Clayton had he ever cheated on her. The thought crossed his mind to stop now, get dressed and leave, but the green-eyed blond under him wrapped her legs around his waist and made a delightful moan.

Leslie beckoned Mr. Clayton to take her, wanting him to satisfy her long-time urge to be with an older man. As his hips pumped her tight, fit body, she touched and rubbed her hands on his rough face, feeling every grainy ridge of his stubble. He moved urgently to enjoy as much of Leslie as possible, kissing her lips and neck and even bending to mouth her nipple.

“I’m close,” Mr. Clayton grunted.

“I’m on birth control,” Leslie whispered in a pleasured voice, her legs pulling feverishly to entice him.

Mr. Clayton slowed to think about it, but he wasn’t one to take a chance like that, and he already regretted not using a condom. He felt Leslie’s arms wrap around his neck to pull him into a kiss, her hips bucking against him in a manner his wife hadn’t been able to do in years. As he grew closer and closer to his climax, the urge to finish inside her tried to overtake his thoughts. He gave a final push, ready to let it all out in her wanting pussy; then, at the last moment, he jerked back just in time for his cock to blow it all over her flat, toned belly.

“Yes, I know what a purse is for, mom,” Jenny sighed as her mother explained its uses for what felt like the hundredth time.

“We’re back from the store,” Mrs. Clayton called out as they stepped into the hotel room.

Jenny sat one purse on the table next to the other two her mom had bought. According to her, a woman needed a purse for different occasions and outfits. For the next few minutes, Mrs. Clayton stocked Jenny’s purse with wipes, a small mirror, a hairbrush, several other oddities, and even a can of mace.

“Did you girls have fun?” Mr. Clayton asked as he exited the bathroom, fresh out of the shower.

“Oh, yes, now Jenny can be a little more prepared when out in the world,” Mrs. Clayton responded to her husband.

“Yeah, I can take on anything now,” Jenny said sarcastically. “I’m gonna go check in with Skylar.

Jenny hugged her mom, then received a kiss on her forehead from her dad as she headed for the door. Andy paused at the entrance to his own room as he noticed Jenny come out. He turned, then walked toward her, eyeing the purse hanging from her shoulder.

“Carrying a purse like some girl now, huh?” Andy jested.

“Yeah, and it comes with mace, so I could try it on you if you like,” Jenny retorted with a sharp smirk.

“You’re cute when you’re mad,” he added.

“I’m not mad,” she clarified.

“Anyway, do you want to hang out when we get back home?” He asked.

“Yeah, we can do something,” she answered.

“Okay, cool, see ya in a little while then,” he said, kissing Jenny.

“Yup,” Jenny peeped after Andy’s lips left hers.


It wasn’t long after Jenny’s segment of the show aired that the news of a man being successfully made into a full woman spread. The information leaped from the show onto the internet, then into the news cycles. Jenny found her social media skyrocket to over two million followers, which presented her with both support and hate. The number of dick pics also increased, along with people sending her edited photos in sexual positions or cum on her pics. This made it increasingly difficult to respond to legitimate messages.

About three weeks after the segment's airing, Jenny reported to a meeting at her job’s corporate office. She entered the conference room and took a seat across the table from several older white men. There had already been whispers and rumors about her getting fired, so she had steeled herself in preparation for any bad news. She could feel their eyes on her, judging her in a mix of disgust and curiosity.

On the left sat the company’s vice-president; to his left sat the president, followed by her district manager, the director of human resources, and finally, a company attorney. There was silence as each person fiddled with various papers before them until they all seemed to come to some non-verbal agreement to begin.

“I do believe you know why you’re here,” spoke the president. “You recently appeared on a talk show, and that bit has gone viral,” he added before Jenny could acknowledge it.

“Yes, I did,” Jenny confirmed.

“Since then, our company has received dozens of inquiries from journalists and other organizations, not to mention concerns from our associates and customers. The former is neither here nor there, but we do care about the customer’s perception of our company.” He paused to collect his words, then looked at the lawyer as if to get approval. “This decision has nothing to do with your transition, but you violated your management contract by appearing on television without prior authorization.”

“I didn’t say anything about the company,” Jenny countered.

“Even so, as a manager in this company, you’re looked at as a representative, and you must conduct yourself as such. Because I know of your valuable work ethic, it makes the decision to terminate your employment difficult.”

“You’re firing me?” Jenny asked more out of disappointment than shock.

“We have to uphold our policies and contracts, Jenny,” he responded. “However, we’ve put together a decent severance package for you as a token of appreciation for the work you’ve done. You’ll receive two thousand dollars for every year of service, you’ll get to keep your vehicle, and we will provide you full benefits for a year.”

Jenny could feel tears forming but forced herself to keep from crying in front of them. This was the only job she had ever had, and now her loyalty to the company was betrayed. She could barely pay attention as the attorney went over the paperwork, and she signed off on it.

As soon as she closed the car door, the tears she had fought ran down her face like a dam had been broken. The thought of getting fired for expressing herself made her slam her hands on the steering wheel with a loud, frustrated yell. Once the initial rush of emotion faded, she wiped her tears and drove home.

Jenny kicked off her heels as she stepped into the house and then made her way upstairs to undress so she could shower. As she approached her bedroom, she saw the door closed and could hear moans, groans, and the bed shifting on the other side. Jenny remembered today was Skylar’s day off, and he told her that morning he was going to hang out with Alice. Jenny wanted nothing more than the comfort of her husband, but she didn’t want to see him fucking Alice right now, nor be around when they emerge after their session. Jenny turned, then quietly went back down, put on her heels, and left.

Alice was in the heat of the moment, riding Skylar’s wonderful cock and reminding him how it feels to be with a real, natural woman. Skylar loved Alice’s nipple and navel piercings and hoped Jenny would get one or both eventually. However, he never asked her since he didn’t want to pressure her. Alice reached her orgasm and leaned forward to lay on Skylar. She knew he had to be close himself but wanted to keep him enthralled by the tight, wet heat of her pussy for now. It would be better for her if Skylar listened to her words while pent up.

“I sometimes think our marriages should have been the other way around,” Alice spoke in a lusty voice, moving her hips enough to keep Skylar’s mind on her sex.

“What do you mean?” Skylar asked with his hands on Alice’s hips, craving for her to speed up and finish him.

“I’m just thinking how it would’ve been if we were married instead, then Jenny and Andy would be married.” Alice kissed his neck. “They’ve been friends for a long time and would be perfect with one another, and us, we work in the same field, so we have a lot in common. Have you ever thought about it?”

“A little,” Skylar said, “but I love Jenny,” he added quickly.

“You love me too,” Alice responded. “And, I love you. I’m in love with you.”

Alice kissed him, pushing her tongue between his lips to prevent him from answering, her hips shoving back and forth to reinforce her words with pleasure. She felt his cock swell up, a physical reaction that she knew meant how close he was. She slowed to a stop and released the kiss.

“I’m in love with you too, Alice,” Skylar voiced in a pleasured groan, his cock on the verge of exploding in her.

Alice smiled triumphantly, knowing that she had broken a major wall, but didn’t want to push it too far at one time. She moaned for his enjoyment while working her hips again, which made his cock swell up, followed by a burst of his seed deep into her womanly depths.

Jenny found herself sitting at the bar of a small, individually owned restaurant, now on her third glass of long island iced tea. With the place being mostly empty at this time of day, there was less risk of someone recognizing her since she was becoming famous now. She finished her third glass and then asked the bartender for one more.

“Jenny?” A man called as he sat on the stool beside her.

Jenny recognized Nate, the guy who took her to that stupid party where all those guys had their way with her. She had accepted that Nate didn’t have anything to do with it, but she still didn’t like him. Even so, Nate was exceptional in bed, and those memories didn’t let Jenny forget.

“What do you want, Nate? Didn’t I tell you I didn’t want to see you again?” Jenny said.

“Yeah, you told me, but you look pretty down, so I came over.”

“Well, I got fired today, so I guess I do look down.”

“Oh, sorry to hear that,” Nate said with concern. “Let me pay for your drinks at least, so your day doesn’t suck completely.”

“Fine,” Jenny answered.

“I’m sure things will look up for you soon,” Nate said after paying, then slid off the stool to leave.

“Where are you going? Jenny asked.

“I don’t want to make your day worse,” he said.

“You paid for my drinks, so you can at least stay until I’m finished.”

“Alright.” Nate took a seat again. “So, what were you fired for? If you want to talk about it.”

“For going on that talk show,” Jenny answered.

“That’s right,” I did see a clip of that, but it didn’t dawn on me that it was you. In fact, I never believed you were a guy, even when you told me. You make a fine ass woman, though.”

“Thanks, I guess,” Jenny said, upset that Nate’s stupid comment somehow made her feel a little better. “I’m surprised you aren’t mad at me. Loads of people who’ve never even met me have made it clear that I’m scum.”

“It’s a little weird, but I’m not mad. And, even though I was an ass to you before, I know you aren’t scum.”

“I appreciate that, but I should get going now,” Jenny said.

“Do you need me to drive you home?” Nate asked.

“I’m not going home yet,” Jenny answered as she stepped down from the stool, making sure she was balanced on her heels.

“If you still have some time, how about I buy you lunch?” Nate asked, glancing at Jenny’s ass and stocking-clad legs as she walked away.

“Okay,” Jenny nodded after thinking about it. Skylar was busy with Alice, Andy was at work, and Leslie couldn’t give her the kind of comfort she was looking for.

Jenny sat with Nate at a booth, and she felt her mood improving as they ate some appetizers and talked. She excused herself as they waited for their main dish, going to the bathroom where her purse would be useful now. She retrieved a small makeup kit and touched up her face, especially around her eyes, since she had been crying.

Nate noticed Jenny’s fresh look, including the shiny coat of gloss on her lips. She didn’t want to talk about herself much, so Nate told her about how he was back in school to become a mechanic. Eventually, Jenny opened up and shared her story about the transition, her life as a girl, and some current events.

“I’m sorry for what happened to you,” Nate said during a silent moment.

“It’s okay,” Jenny started but was cut off.

“No. I knew what kind of people would be at the party, so I shouldn’t have invited you.”

“I should’ve been more diligent,” Jenny said softly. “

They were quiet for a while as they finished eating, and Nate paid the check. His eyes looked down to her neck and blouse at times, trying to look at Jenny’s hidden cleavage, which she noticed but didn’t say anything about. It didn’t matter since her work clothes weren’t much to look at, except her legs and maybe her hips. Jenny didn’t know if it was because of his manners today or because she was tipsy, but she felt frisky now as they sat there. She had planned for Nate to be a friend with benefits back then, but that was short-lived, so she never got another round with him. All she had was the memory of him eating her out on the bathroom sink, then having a quickie before she rushed off to work.

Nate looked up from the table as he felt something brush between his legs, then realized it was Jenny’s foot as she pressed against his crotch. Her toes moved up and down, making his blood flow into a stiff erection inside his shorts. Jenny wasn’t looking at him but was looking at her phone as if her attention was on something important. As Jenny put her phone away and looked up, she pulled her foot back as well. Nate’s expression was filled with lust and anticipation, especially since he knew he’d never get to fuck her again. Now, that seemed to be back on the table.

“What do you have planned for the rest of the day?” Jenny asked.

“Right now, just making sure you get home safely,” Nate answered.

“Why wouldn’t I get home safe?” Jenny asked, confused as to why Nate didn’t take her very forward hint.

“You’re a little tipsy,” Nate answered. “And, as much as I would love to take this further, I’m not going to do anything to put you in a bad place again,” he added as he had to hold Jenny’s foot back from rubbing on him once more.

“Fine,” she responded, then began sulking. “You know, my husband is at home fucking my best friend’s wife right now,” she blurted.

“He’s cheating on you?”

“No. We all agreed to be in an open relationship with each other, but I think Alice is trying to get him to leave me.”

“Why do you think that?”

“It’s just a feeling I have.”

“Is that why you’re here instead of at home?”

“Yeah, I heard them through the door, so I left and came here. I’m supposed to be at work until this evening.”

“Tell you what. Why don’t you come over to my place and crash for a bit?”

Nate’s Place

Nate drove Jenny’s car back to his place since he had walked, and his townhouse wasn’t that far. The inside was nicer than Jenny expected, especially the hardwood floors. Nate introduced her to his roommate, Luke, then showed her to the guest room upstairs, which was just as nice. Jenny looked around at how the place was decorated, from the carpet to the furniture and even the curtains. It was obvious he inherited this place from some older relative because no guys would’ve chosen this décor.

“Do you mind if I take a shower?” Jenny asked as Nate turned to leave.

“Oh sure, I’ll bring you a towel and washcloth.”

“That’s a good catch there, bro,” Luke said to Nate when he came back down. “Fit body and a nice fucking rack.”

“It isn’t like that,” Nate responded as the water could be heard coming on upstairs.

“So, you’re not going to fuck her?” Luke asked with a stupified look.

“No,” Nate answered. “At least, not today. It’s a long story, and I’m just letting her crash here for a few hours, so no funny business.”

“Okay, okay, fine,” Luke said, very disappointed.

Jenny didn’t want to stay in the shower too long, so she only let the hot water run over her for a minute before washing up, then stepping back out to dry off. She checked the hallway, stepped quickly across and back into the bedroom where she finished drying, then slipped her bra and panties on.

“Come in,” Jenny called out in response to a knock on the door.

“Oh! Sorry!” Nate chimed and adverted his eyes to the floor as he glimpsed Jenny in her underwear.

“It’s okay,” Jenny said softly, still feeling the aroused heat burning in her loins.

“I wanted to see if you needed anything to drink or something,” Nate said.

“Nothing like that,” Jenny answered, wanting him to look at her, undress her, and fuck her. She wanted attention.

“Okay, just let me know if you need anything,” he said, then quickly exited before Jenny could say anything further.

Jenny flopped on the bed, feeling insulted that Nate wouldn’t accept her advances. Guys didn’t turn down women, especially when it came to free sex. Before she could think about it more, sleep took her, and she found herself in a dream. She was back in the restaurant sitting next to Nate, her head in his lap as she sucked his dick. This Nate was much more accommodating to her wants, even going as far as to fuck her right on the table while everyone watched. Several guys were also nearby, jerking themselves off to their carnal display.

Luke slowly pushed the bedroom door open, his excitement spiking as he saw Jenny on the bed in nothing but underwear. She was on her stomach, one leg curled up at an angle. He had the urge to touch her but didn’t want to wake her up. For now, he poked his finger against her knee to make sure she was sleeping. He snapped pictures of her with his phone, hoping that she’d turn over so he could get shots of her tits too.

His dick was raging just from the view of her well-rounded ass and long, silky legs. He had no damn clue why Nate would pass up fucking such a willing slut. The phone beside Jenny on the bed caught his eye, and he picked it up. The wallpaper was a picture of her and who he assumed to be a boyfriend or something. A wave of disappointment came over him at the sight of the fingerprint lock, but that was quickly overtaken as he looked down at Jenny’s easily accessible hands.

Luke placed the phone face up on the bed and carefully moved Jenny’s hand into position, his eyes watching her face for any signs of stirring. His fingers pressed her thumb to the screen and the phone unlocked on the first try. He picked it up and stepped back, only interested in seeing her gallery. There were hundreds of pictures on the phone, sorted into album folders. There were innocent pics and even more risqué photos, but he wanted to see her in true slut form.

Inside the Honeymoon album, Luke found a plethora of nudes, followed by pics and videos of her giving blowjobs and getting fucked. In the For Hubby album, he found plenty of solo Jenny content of her masturbating and talking dirty for Skylar. He knew Jenny was a slut, but damn, was she a talented one too. He hurried from the room with her phone in hand, booted up his laptop, and copied as much as he could from her gallery.

When Jenny finally awoke, there was no daylight left coming through the window. The clock on the wall pointed to nearly 10pm, which she confirmed with her phone. She had a single text from Skylar asking if she was okay, to which she replied, “yes, something happened at work, will tell you when I get home.” She put the rest of her clothes on and headed downstairs, relieved that Nate hadn’t accepted her advances. Now she felt bad for teasing him with no intention of following through.

“There you are,” Nate said as he heard Jenny come down. “Feel any better?”

“A lot better, thank you,” Jenny smiled. “And thank you for helping me make good decisions,” she added.

“Big loss for me,” Nate smirked. “But, I don’t want you to think I’m some kind of predator or something.”

“Well, I need to head home, but maybe we can hang out later,” Jenny offered.

“That’d be great,” Nate said, hoping he would have another chance with her.

Nate watched Jenny as she left the house and got into her car. Once she pulled away safely, he closed the door and turned to hear his roommate, Luke, comment about not fucking Jenny. Luke was upset at the missed opportunity, wishing that he had been the one with the chance to smash Jenny. It wasn’t a complete waste, though, not with all the pics and videos he had gotten from her.


bottom of page