A Gender Swap Roleplaying Game

Story Info
A young couple tries to spice things up with role play games.
4.6k words
4.74
34.4k
77
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

David and Alice were a young couple who had been together for quite some time. Recently, they felt that their relationship needed a little excitement to keep the spark alive. David came up with an idea of spicing things up by introducing roleplay games into their bedroom activities.

Initially, Alice was hesitant about the idea, but she eventually warmed up to it after seeing how excited David was about it. They decided to explore different scenarios and characters during their roleplay sessions.

To make it more realistic, they even got costumes and outfits that would help them get into character better. Sometimes they would try out new costumes based on popular TV shows or movies while other times; they would attempt to create their own unique looks from items in their wardrobe.

Alice loved dressing up in various costumes as she felt like a completely different person each time they played these games. On the other hand, David enjoyed playing his part as the man in charge of every situation.

Overall, this experience brought them closer than ever before and added some much-needed fun and excitement to their relationship. It was something that both of them looked forward to doing whenever possible!

One day, Alice had a wild and crazy idea that she just couldn't shake. She suggested to David that they try doing a gender swap. However, David didn't seem too thrilled about the idea at all. He expressed his concerns and hesitations towards it.

-

I hope you enjoyed this story.

xoxo Nathalia

"I just don't understand why you're so against it," Alice complained to David. "I mean, I always put in so much effort into my outfits and appearance for our roleplay games. But you don't have to do much at all. It's time for you to pull your weight and see what it's like on the other side of things."

David shook his head, "It's not that I'm against it, Alice. It's just that I don't feel comfortable dressing up as a woman. It's not who I am."

"But that's the whole point of roleplaying, isn't it?" Alice argued. "To be someone different from who we are in real life? Plus, it'll add a new level of excitement to our games."

"I understand where you're coming from," David said, "but I'm just not sure if I'm ready for something like that yet. Maybe we can try something else first?"

Alice was determined to make the gender swap happen and she wasn't going to give up that easily. She saw this as an opportunity to explore new territories and add some extra spice to their roleplay sessions.

"I promise you, David. It won't be as bad as you think," Alice said, trying to reassure him. "We can start small and see how it goes. And if at any point you feel too uncomfortable, we can stop."

David hesitated for a moment before finally giving in to Alice's request. He trusted her and knew that she wouldn't push him too far out of his comfort zone.

"Okay, let's give it a try," David said, with a hint of nervousness in his voice.

Alice was overjoyed at his response and immediately started planning their next roleplay session.

David and Alice were both of similar body sizes, which made Alice quite confident that she would be able to find something from her wardrobe that could fit David.

As she thought about the upcoming roleplay, she realized that there were a few other items that would make it even more exciting and immersive. She knew that in order to create the perfect atmosphere for their game, she needed to get her hands on those additional props. So without any hesitation, she decided to take matters into her own hands and went shopping the very next day. She wanted everything to be just right - from the costumes they would wear down to every little detail of their surroundings. With excitement building up inside of her, she made sure not to tell him anything about what was happening behind-the-scenes as he eagerly awaited their planned activity together.

The week had been long and tiring, but finally Friday had arrived. Alice and David both returned from work, looking forward to some relaxation time together. They sat down for dinner, enjoying each other's company as they chatted about their day.

As the meal came to an end, Alice couldn't contain her excitement any longer. She turned to David with a sparkle in her eye and asked him if he trusted her. He looked at her quizzically but nodded his head in agreement.

"I want tonight to be perfect, David," Alice said with a smile. "But I need your full cooperation."

David raised an eyebrow in curiosity.

"As you know, you'll be playing the female role tonight," Alice continued. "And I'm more than happy to help you with dressing up and make-up, but there's just one thing..."

David looked at her expectantly.

"You'll have to shave your legs," Alice said, with a hint of hesitation in her voice.

"What? No way!" David exclaimed.

"It will make the roleplay more exciting," Alice protested. "And your hair will grow back anyway."

"But it's such a hassle," David complained.

Alice sighed. "It's not fair that I always have to put in so much effort, and when it's your turn, you don't want to do anything."

David considered this for a moment before finally giving in. "Fine, but if I get razor burn, it's on you."

"Deal," Alice said with a grin.

David reluctantly headed to the bathroom, feeling a little self-conscious about shaving his legs and chest. He had never done anything like this before, but he didn't want to disappoint Alice. As he shaved away his body hair, he couldn't help but feel a bit silly.

Meanwhile, Alice was busy preparing his outfit in the bedroom. She had carefully selected every piece of clothing and accessory, making sure it would fit him perfectly. She couldn't wait to see him all dressed up and ready for their roleplay.

After what felt like an eternity, David emerged from the bathroom, feeling a bit strange with his newly shaved skin. Alice greeted him with a smile and showed him the outfit she had picked out.

"You're going to be a sexy secretary tonight," Alice said with a wink.

David looked at her skeptically. "I don't know about this, Alice..."

"Don't worry, you'll look amazing," she assured him as she showed him the white top and pencil skirt she had picked out.

"And I'm going to be your boss," she continued. "I'll wear one of your suits for the roleplay as the man."

David still wasn't feeling too good about it, but he didn't want to back out now.

"Okay, let's do this," he said with a sigh.

Alice led him over to the vanity and asked him to sit down so she could apply makeup. She started by smoothing out his skin with foundation, then added a touch of blush to his cheeks.

Next came the eye makeup. She carefully applied eyeliner and mascara, making his lashes appear longer and more feminine. Finally, she finished off the look with a bold red lipstick that made David's lips pop.

As she stepped back to admire her handiwork, Alice couldn't help but feel proud of herself. David looked stunning, and she knew their roleplay was going to be unforgettable.

"You look incredible, David," Alice said as she admired her work.

David couldn't believe how different he looked. He had never worn makeup before. He felt like a completely different person.

As he was admiring himself in the mirror, Alice brought out a small bag from their closet.

"What's that for?" David asked curiously.

Alice grinned mischievously. "I bought some lingerie for you to wear tonight."

David's eyes widened in surprise. "Lingerie? Alice, isn't this going too far?"

But Alice was already pulling out a lacy bra, slip, and stay-ups from the bag. "I got them just for this occasion. I hope they fit you."

David hesitated, unsure if he wanted to take it this far. But Alice convinced him to at least try it on and see how it made him feel.

With a deep breath, David headed back into the bathroom to change into the lingerie.

David slowly undressed, feeling a bit nervous about what he was about to do. He took off his underwear. As he reached for the slip, he hesitated for a moment before putting it on. It felt tighter than he expected and the material felt strange against his skin, but he tried not to let that bother him.

Next came the bra - something David had never worn before. He fumbled with the clasps at first, unsure of how they worked or where each strap should go. But after a few attempts and some adjusting in front of the mirror, he finally managed to fasten it correctly.

Finally came the stay-ups - another thing that was new to him. He carefully rolled them up his legs one by one, making sure they were straight and even as best as possible. It took a few tries to get them right since they kept slipping down before reaching their intended place on his thighs.

As David stood there fully dressed in women's lingerie for the first time ever, he couldn't help but feel both exhilarated and scared at once. The tightness of the slip still bothered him slightly, but overall everything seemed to fit okay.

Looking at himself in the mirror, David couldn't believe how different he looked with the makeup and lingerie. He felt so different, almost like another person entirely. Seeing the bulge in his panties excited him a bit, but he also felt ashamed for enjoying it.

Despite his reservations, David decided to go through with the roleplay. He knew Alice would be disappointed if he backed out now, and he didn't want to ruin their evening together.

David heard Alice knocking on the bathroom door, asking if he was okay. He hesitated before answering, not wanting her to hear the uncertainty in his voice. Finally, he managed to say that he was fine.

He didn't want Alice to see him like this - dressed up in lingerie and makeup. It felt too vulnerable, too revealing. He told her to wait a second and quickly grabbed a bathrobe.

As he wrapped it around himself, Alice spoke up again. She said she left the rest of his outfit next to the bathroom door and that she wanted to change now as well.

David took a deep breath and opened the door just enough to grab the bag of clothes. He closed the bathroom door once again and leaned against it for a moment. This whole thing was so new and strange to him, but he couldn't deny that there was something thrilling about it all.

With another deep breath, David pushed off from the door and opened the bag. Inside he found the pencil skirt and the white top Alice had picked out for him. He carefully took

them out and found something else at the bottom - a blonde

wig. David stared at it for a moment and couldn't believe

that Alice had gone this far. He picked it up and ran his fingers through the strands before he slowly put it on.

He continued with the white tank top, pulling it over his head and smoothing out any wrinkles. The fabric felt soft against his skin and he couldn't help but shiver slightly at the sensation.

Next came the skirt. He wondered if it would even fit him - he was slim but not as slim as Alice. But it was stretch material, so it fit snugly around his hips without feeling too tight.

David took a deep breath and stepped back to look at himself in the mirror once again. He couldn't believe how different he looked now compared to just a few minutes ago. With the wig on, he almost didn't recognize himself.

As nervous as he still felt, David also couldn't deny that there was something exciting about all of this. The way the clothes hugged his body made him feel sexy in a way he had never experienced before.

He heard Alice knocking on the door again, asking if everything was okay. David hesitated for a moment before responding, trying to steady his voice. "Yeah, I'm ready," he called out before taking one last deep breath and opening the bathroom door.

"Wow," Alice breathed as she took in his new outfit. "You look absolutely stunning."

David felt his cheeks flush with heat as Alice complimented him. He felt nervous and embarrassed, but also strangely excited. He had never felt like this before and he wasn't sure what to do with the emotions that were bubbling up inside of him.

Alice stood before David, wearing his suit - the same one he had worn to work earlier that day. It was strange seeing her in it, but he couldn't deny that it looked good on her. The shirt and tie fit her perfectly and she wore them with a confidence that made David feel even more nervous about his own outfit.

He cleared his throat and shifted his weight from one foot to the other, feeling self-conscious under Alice's gaze. "You look good too," he managed to say after a moment.

Alice grinned at him and stepped closer, reaching out to adjust his wig slightly. "I wasn't sure if it would fit you, but I'm glad it does," she said with a smile. "You look amazing."

"Thank you," David replied, feeling a surge of excitement as Alice adjusted his wig. "So what's next?" he asked, eager to get started with the roleplay.

Alice grinned mischievously. "I'll be Mr. House and you'll be my secretary Darcy," she explained, leading him towards the living room. "Follow me."

"Alright, Darcy," Alice said, looking over some papers. "I need you to call my wife and tell her not to wait up for me tonight. It's going to be a long night."

David picked up the phone and pretended to dial a number, speaking in hushed tones as he put on his best impression of a woman's voice.

"Hello, Mrs. House? This is Darcy calling from the office. Your husband wanted me to let you know that he won't be home tonight. He's got some important work to take care of."

Alice watched him with interest as he hung up the phone, nodding approvingly at his performance. "Good job, Darcy," she said with a smirk. "Now, I need you to stay here and work on these documents with me. We've got a lot of ground to cover."

David felt a shiver run down his spine at the sound of her authoritative tone. He was really getting into character now, enjoying the thrill of playing this new role. "Yes, sir," he replied obediently, eager to see where this game would take them next.

"Can you do me a favor, honey?" Alice asked, glancing up at David. "I need those folders from the other side of the room."

David felt his face flush with excitement as he heard her use that endearing term. He quickly made his way over to the other side of the room, feeling her eyes on him the whole time. As he bent down to pick up the folders, he could feel her gaze lingering on his legs, and he couldn't help but smile to himself.

He brought the folders back to her and set them down on the table, trying to keep his composure as she flipped through them. This new game was really getting under his skin, and he was starting to lose himself in this fantasy world they had created together.

Alice beckoned David over to her side of the table, pointing at a document that needed his attention. He leaned forward, his heart pounding in his chest as he felt her breath on his neck.

"That's it," she murmured, running a finger down the page. "I need you to take a closer look at this section right here."

David tried to focus on the words in front of him, but all he could think about was how close they were, how much he wanted her. He could feel her body heat against his back, and he couldn't resist the urge to lean in even closer.

David felt a jolt of electricity shoot through his body as he felt her hand on his butt. He tried to stifle a gasp, but couldn't help the moan that escaped his lips.

Alice chuckled in response, clearly enjoying the power she held over him. "You know, Darcy," she said with a smirk, "I can't help but notice how tight your skirt is. It's almost like you're trying to distract me."

David blushed furiously at her words, feeling both embarrassed and aroused all at once. He played the role of the shy, obedient secretary to perfection, pretending to be hard to get even as he longed for her touch.

"I-I don't know what you mean, sir," he stammered, trying to keep his voice steady despite the desire that coursed through him.

Alice leaned in close to him again, whispering in his ear. "Oh, I think you do," she murmured. "And you know what? I like it."

"How long have we been working together, Darcy?" Alice asked, her eyes fixed on David's.

"Uh, about a year now," he replied quickly, not wanting to break the spell they had created.

Alice nodded thoughtfully. "It feels like longer," she said with a smile. "We make a good team."

David grinned back at her, feeling a sense of pride at her words. He made his way over to the other side of the table.

"What do you need me to do next, sir?" he asked, eager for more of her attention.

"I need you to write down this letter," Alice said, dictating the words slowly and deliberately. "Make sure you get every word right."

"As the head of this company, I demand that our sales figures improve," Alice began dictating. "We need to do whatever it takes to increase revenue and stay ahead of the competition."

David scribbled the words onto the paper as quickly as he could, trying not to make any mistakes.

Alice got up from her chair and walked over to David, who was still writing down the letter. She stood behind him and started massaging his shoulders slowly, feeling the tension in his muscles melt away under her touch.

"You know, Darcy," she said in a low voice. "I've always admired your work ethic. You're so dedicated to your job, always willing to go the extra mile."

"Th-thank you, sir," he stammered, trying to keep his voice steady.

She continued with a sly smile, "You look sexy in that outfit. My wife doesn't dress as feminine as you do. I wish she would."

"Get up, Darcy," Alice ordered, her voice firm but seductive. "I want you to reach over the table for the pen."

David hesitated for a moment, feeling a rush of excitement and nervousness at her command. He slowly stood from his chair and leaned forward, stretching his arm out to grab the pen.

As he did so, Alice moved in behind him and gently grasped his hips, pulling him closer to her body. David could feel her breath on his neck as she whispered in his ear.

"You're such a good girl," she murmured. "So obedient and willing to please."

David's heart raced as he felt her hands move up and down his sides, teasing him with soft caresses. Suddenly, he felt something hard pressing against his butt cheeks. He was surprised and turned around to look at Alice.

"What...what is that?" David stammered, pointing at the bulge in Alice's pants.

Alice just winked at him and asked, "What's wrong, Darcy?"

David didn't know how to take it. He felt like things were going too far. He wasn't gay, but the excitement he was feeling was beyond anything he had ever experienced before.

Alice noticed his excitement and pointed at the bulge in his skirt.

"You like what you see, don't you?" she whispered seductively.

David could feel himself blushing as he nodded his head slowly. He couldn't believe this was happening. But at the same time, he didn't want it to stop.

Alice leaned in even closer to David, her breath hot on his neck. "Do you want to touch it?" she asked in a sultry voice, gesturing toward the bulge in her pants.

David's mind was racing as he considered the question. He had never been attracted to men before, but something about the situation they were in was turning him on like never before.

He hesitated for a moment before nodding his head slowly. Alice grinned and reached down, unzipping her pants and pulling out a large strap-on dildo.

"Go ahead," she said, holding it out to him. "Touch it."

David took the dildo in his hand, feeling its weight and texture. It was soft but firm, with intricate veins and ridges running along its length.

Alice watched him intently as he explored the toy with his fingers, her eyes filled with excitement and desire.

12