Greg eventually emerged from the bathroom, freshly shaven, showered, and with a towel around his narrow waist. By this time, his arms had been nearly completely swapped and appeared thinner and hairless. Everything below armpit level looked like his wife Kim's body, but everything above that line was still his own.
Kim wasn't surprised by the continuing transition as her own body looked like her husband Greg's body below her armpits and she was still herself above that.
As Greg walked out of the room, he offered a suggestion to Kim. "Hey, I was thinking. We probably should have bought you a fake beard. Then you could have been the long-haired Linux neckbeard."
"Nah," Kim replied. "Those things always look fake. Even FX makeup artists in Hollywood have a hard time giving actors convincing fake beards. Remember that obvious fake beard that Samuel L. Jackson had in Secret Invasion? I mean, that's a Marvel TV show and even they can't get it right."
Greg shrugged. "Yeah, I guess you're right, Kim. But are you sure about being able to make me look convincing?" Greg asked, glancing at his reflection in the mirror. "I mean, I'm all for trying this, but I don't want to look like a caricature."
Kim smiled warmly, her eyes full of reassurance. "Don't worry, Greg. We'll make you look convincingly like a woman, but not over the top. You'll be elegant and sophisticated. Just trust me and relax." Kim handed Greg a hotel robe. "Why don't you put this on? Then I'll get started. I'll do your makeup first and then you can get dressed."
Greg put the bathrobe on and sat on the desk chair near the foot of the bed. Kim had already spread out all the makeup she had brought with her as well as her earlier purchases on the desk. "I'm your canvas, Michelangelo. Show me what you've got!"
"I'm no Michelangelo, but I'll do my best." Kim leaned down and kissed him before going to get a chair from the table near the window and pulling it back to the desk. Once seated, she began by applying a moisturizer, letting her fingers massage his skin tenderly. Greg closed his eyes, savoring the sensation.
As Kim dipped a makeup sponge into a liquid foundation, she started applying it to Greg's face, blending it seamlessly to create a smooth and flawless base. "You have great skin, Greg," she remarked. "You hardly need any coverage."
Greg chuckled, "Well, thanks for that. Maybe I should start a skincare routine."
Kim proceeded to conceal any blemishes and under-eye circles with a light touch, accentuating Greg's masculine features just enough to soften them. "Next, we'll define your eyebrows a bit," Kim explained, picking up an eyebrow pencil. She carefully shaped Greg's brows to give them a softer, more feminine arch. "Don't worry; it's just a subtle enhancement. We want you to look natural."
Greg chuckled nervously, "I never thought I'd be getting my eyebrows done, but I'm curious to see how it turns out."
As the transformation continued, Kim applied a natural blush to Greg's cheeks and a soft, rosy lip color. She then used a setting spray to ensure it would last throughout the evening.
Next came a neutral eyeshadow palette to give Greg's eyes a natural and subtly feminine depth. With a steady hand, Kim applied a thin line of eyeliner, framing his eyes subtly. "Blink for me," she requested, and Greg followed her lead. She followed up with mascara to add length and volume to his lashes, bringing attention to his eyes.
"Now, for the finishing touch," Kim said, picking up the brown wig that cascaded in waves down to the shoulders. She placed it on his head and then applied some wig glue to the lace front to help it look more natural. As she secured the wig onto Greg's head, she couldn't help but admire how stunning he looked.
"You look amazing," Kim declared, her voice brimming with admiration. "The wig suits you perfectly, Greg."
Greg looked at himself in the mirror, trying to see past the masculine features and imagine the woman he was supposed to become. "I hope I look convincing enough," he said quietly, still feeling uncertain. "What about my voice? That's definitely ruining the illusion."
"Yeah," Kim agreed. "I'll have to do all the talking and will tell people you've lost your voice from cheering too much at a concert and need to rest your vocal chords."
"That sounds plausible." Greg continued looking at himself in the mirror. "I hope my masculine jaw isn't too obvious."
Kim frowned, feeling her own confidence waver. "I know, Greg. It's not easy to completely alter facial features with makeup alone. I was hoping we could achieve a more convincing look, but I might have underestimated the challenge."
Greg's worry deepened, and he stared at his reflection with a mix of admiration for Kim's effort and anxiety about being discovered. "Maybe we should reconsider this whole idea. I don't want to embarrass you or myself," he said, his shoulders slumping.
Kim reached out and gently held Greg's hand. "I understand, and I'm sorry if I got carried away with the excitement. But remember, this is just one night, and we can always leave early if you're uncomfortable. Also, remember that nobody in town knows us so if they think you're really a guy, so what?"
Feeling a bit reassured by Kim's words, Greg took a deep breath. "Okay, let's give it a shot. But if at any point things get awkward or people start looking at us strangely, we promise to leave without any hard feelings," he said, trying to muster some confidence.
Kim nodded in agreement, admiring Greg's resilience. "Deal. And remember, this is about having fun together. Let's focus on enjoying each other's company on our anniversary, regardless of how the transformation turns out."
Greg smiled, stood up, and hugged Kim. "Don't make me cry! I'll ruin my makeup!" They laughed together.
After the hug, Kim headed to the closet. "Okay, lets get you dressed." She took a navy blue knee length dress out of the closet and held it up. Greg had seen it on Kim before and she had looked stunning in it. "I had planned to wear this tonight, but there's no way it will fit me now. I think you should wear it."
Greg hesitated for a moment. "Won't that show a little too much of my cleavage?"
Kim laughed. "You never seemed concerned when I wore this. Besides, showing a little cleavage should help sell people on the idea that tonight you are a real woman. If you cover yourself up, you'd look more like a skinny guy in drag."
"Okay, you have a point." Greg took the dress and laid it on the bed next to a bra and panties which Kim had already laid out. As Greg started getting dressed, Kim worked on her own makeup. When he attempted to put on the bra, he asked Kim to help fasten the back after fumbling around himself for a minute.
Greg held up the dress and looked at Kim. "Stupid newbie question... Do I step into it or do I pull it over my head like a shirt?"
Kim laughed. "Greg, you've seen me put on dresses how many times and you never paid attention?"
He grinned with embarrassment. "I think I've seen you do both."
"Okay, fair point," Kim conceded. "If it's something like a sundress, I'll usually pull it over my head. The neck usually isn't large enough to step into and I'd have trouble getting it past my hips. If it's got a back zipper like that one, I'll step into it. You should really step in so that you don't mess up your hair."
Greg thanked Kim and stepped into the dress. Once he had his arms in, he turned and Kim zipped him up. He looked at himself in the mirror. "Wow, from the neck down I look pretty damn hot."
"Thanks! That's my body you're complimenting there," Kim said with a laugh.
Greg chuckled. "If I still had my dick, this dress would be tenting out right now."
Kim rolled her eyes. "...and the moment's ruined. You do look great though. I think you're pretty convincing. You'll be even more convincing once our shoulders swap." She ran her fingers along the top of Greg's chest. "I noticed you shaved the top of your chest. Good idea. You really wouldn't want a patch of chest hair above your breasts."
"Yeah, it looked really odd in the mirror when I was shaving my face, so I figured I should fix that," explained Greg. "The downside is that as we swap, you'll end up with a bare patch at the top of your chest. At least nobody will notice since you'll be fully covered up." Greg looked at the bed and noticed there were no clothes laid out for Kim to wear. "What are you going to wear, by the way?"
"I was originally considering wearing the same skirt I wore earlier today along with your long sleeve dress shirt, but realized that it would be more and more difficult for me to pass as a woman as the transition worked its way up my face. I decided I should wear your suit. I'll start the evening with your black dress pants and white dress shirt with my bra underneath. I don't think anyone will think anything of it and I'll look like a woman wearing a business outfit. At some point, I figure it will be easier for me to pass as a long-haired man, but I'm not sure when that will happen and I'm not constantly looking in a mirror, so I'll rely on you to let me know. When it's time, I'll remove my makeup, put on a tie and your suit coat, and hand you my purse."
"That sounds like a good plan, but maybe I should carry your purse from the start," suggested Greg. "It might help convince people I'm a woman. Besides, I've got no pockets with this dress."
Kim shrugged. "I suppose, but don't forget that I also have to convince people I'm a woman up until a point."
"That'll be easy," argued Greg. "Talk. Your voice would convince anyone up until it starts to change."
"Okay, that's true. You go ahead and take my purse," conceded Kim. "Let's put your ID and phone in there. I'll carry my phone in my suit pocket. And believe me, I do want to take my phone. I can't believe we haven't taken more photos of this experience!"
"Who would we ever show them to?" asked Greg. "I don't want our friends to see this. Don't you dare post my photo on Instagram!"
"No, no," Kim reassured him. "This would only be for our private album. It would be nice to be able to look back on this and see photos to remember our first anniversary weekend."
"Okay," Greg agreed. "It's a good thing I trust you."
"Once we're ready, we should go get some lunch", suggested Kim. "I'm pretty hungry. Plus, we can test our appearance in public before venturing out to the hotel Howard is performing at."
"Okay, that sounds fine. I'm not too hungry, but I should eat." Greg slipped his feet into a pair of navy blue shoes with short heels that Kim had placed next to the bed. "I hope I'm okay walking in these," he worried.
"I think you'll get the hang of them quickly," Kim said reassuringly. "That's another reason why I picked the navy blue outfit for you. It has the lower heels."
Kim finished getting dressed, put makeup remover pads in her purse, and handed the purse to Greg. She then took Greg's suit coat and a tie. She rolled up the tie and put it in the suit pocket and slipped her phone in another pocket before hanging the coat off her arm. Standing near the door, she looked at Greg. "Is my lady ready to go get some lunch?"
"Yes, sir!" said Greg with a smile.
The two headed out of the hotel room and went off to find some lunch and test their looks in public.