“First we need to get you shaved up,” said one of the girls. She walked over to a showerhead, which was just on the side of the room—not even in a bathroom.
“I shaved this morning,” Boone said. “Before my flight.”
“Not your face, Mr. Parker. Everything else. Get undressed please.”
Boone hesitated. “What are you talking about? I’m not shaving my body, if that’s what you mean.”
“I’m afraid it’s a rule, Mr. Parker. We can’t let you stay at the resort if you don’t follow the rules. Don’t worry—Tania and I have been doing this for a long time. We won’t accidentally cut you or anything.”
Boone’s heart fluttered. “Why do I need to be shaved?” he asked, his voice cracking slightly. His skin suddenly felt cold, despite the warm weather.
Tania laughed. “Because hair legs aren’t very ladylike.”
And then it hit Boone: they were going to feminize him, turn him into a lady for the lady. This must have been one of those ‘walk a mile in her shoes’ sort of challenges. They did something similar at a work seminar, making all of the guys wear heels for the day so they knew how uncomfortable their female co-workers were at work. It just turned into silly shenanigans, of course, and no one learned anything valuable.
Boone rolled his eyes. “Fine. I’ll play along. But only because I love my wife and apparently I need to prove it.” He walked over and pulled off his shirt. The girls looked at his chest and started to giggle. “What?”
“You’ve got the perfect body for this,” Kate said.
Boone couldn’t believe his ears. Was she insulting him? Did he seriously pay ten grand to be insulted? “Watch your mouth, girl. Don’t think I won’t tell your manager about this.”
“It’s a compliment, sir,” she said. “Or I should say, miss.” She cracked a big smile, and now Boone was seriously confused. Were they mocking him? “Now take everything off so we can get you shaved up.”
Boone stripped down to his boxers. Then he looked around. “My swim shorts are in my suitcase. I think I left it down in the lobby.”
“Take off your boxers, sir.”
“Are you kidding me?”
“Sir—it’s part of your counselling. Don’t worry—we’ve done this dozens of times. We’re professionals.”
Boone looked around in a state of shock. He was still tired from only getting a couple hours of sleep—and he only had about ten hours banked throughout the week. His head was spinning. He still couldn’t tell if they were messing with him or if this was actually part of the therapy. He took a deep breath and then he slipped his boxers down to the ground. “If you take pictures of this, I will sue, and I will win. I know the best lawyers in the country—believe me.”
He stepped forward into the stream of warm water. He closed his eyes to avoid making eye contact with the snickering girls. He knew he didn’t have a small cock—it was larger than average—so they were probably just laughing at the fact he was actually going through with it. Or maybe their laughter was supposed to be part of the counselling, to make him feel vulnerable. If so, it was working. It felt strange when they started running their razors down his legs. It felt even stranger when one of the girls gently lifted up his cock and ball sack to shave between his legs. A moment later, Kate grabbed him by the tip of the penis and held his cock up. She started to gently massage his tip, making his heart stutter. He was starting to get hard. “W—What are you doing?” he said. He wanted to slap her hand away because he figured it was part of some kind of test, but at the same time, it felt really nice. His wife hadn’t massaged his cock like that in months—maybe even years.
“I’m getting you hard so that I can shave around your balls. It’s easier if you’re hard,” she said with a shockingly casual smile. Boone was speechless. He just stared down as she ran her young, gentle fingers around his shaft. She got him hard fast. His legs were squirming and he was tingling all over. She continued to hold his shaft as she gently shaved away his pubic hair. “It’s not going to be easy to keep this thing hidden,” she said to her co-worker.
“We’ll have to tuck it,” said Tania. Then she looked up at Boone. “Have you ever tucked before?”
“I don’t know what that means,” he said. His cheeks were dark red and his mind was still spinning, still slow to process what was happening.
Then, Tania grabbed his ball sack in the palm of her hand and she pushed up. “You just get your balls pushed up to where they came from, and then you push your dick back—like this.” Boone suddenly felt a strange discomfort as his testicles shot up into his body. Then he looked down and saw that his ball sack was now just an empty flap of skin. It was an off-putting sight. “I would push your cock back, but it’s really hard right now. Are you going to be able to stay soft once we have you dressed up? Some guys have a hard time staying soft, especially in lingerie. It helps if you jerk off before you get changed. We don’t mind if you want to do that quickly.” They were both looking into his eyes, both with little smirks on their faces, as if they were trying their hardest not to burst into laughter. Surely they were pranking him, trying to see just how stupid he was.
“I’m fine, thank you,” he said. But he really did feel like an idiot, all shaved up and erect in front of two young girls who were almost half his age.
After his shower, one of the girls ran and got some clothes. First, she tossed a lacy piece of lingerie at him. “Put that on first,” she said. He stared at it for a moment, wishing he never went on this trip. Now he was sure that this was all just a test: a test to see if he truly was committed to his wife. For the next week, he had a feeling they would constantly be making him feel embarrassed and idiotic, just to try to get him to snap and give up. But he couldn’t give up. He had to everything they said so he could prove to Lacy that he really loved her.
So he put on the lingerie one piece. It was tight, and it left his whole ass uncovered. He somehow felt even more exposed in the lingerie than he did when he was naked. He looked down at his smooth legs, which looked terrifyingly feminine. “I knew it would look good on her,” one of the girls said.
“Look at those legs. You’ve got the prettiest legs,” said the other girl.
And it was true: looking down, it looked like he was looking at a female’s legs. One of the girls got down on her knees and started rubbing some floral-scented moisturizer up and down. “This will give you a nice shine for the rest of the day,” she said. He didn’t protest. He let the girls have their fun, trying his best not to falter so they wouldn’t get their satisfaction.
Next, they gave him a white sundress. It was crochet on the outside, with a satin lining on the inside. It felt nice against his skin, and it was incredibly light. It completely covered the lingerie, making him wonder why he had the lingerie on in the first place.
One of the girls came over with some costume jewellery. “Put some of this on. And then we’ll paint your nails.” Boone just bit his tongue and played along. While the girls were painting his nails a white shade to match his dress, he closed his eyes and counted the seconds. With each second that went by, he was one second closer to being done with this nonsense.
When he opened his eyes, there was a spread of makeup supplies in front of him. “Is this really necessary?” he asked.
“Of course it is. And after today, you’ll be doing your own makeup, so pay close attention. We’ll do our best to explain everything we do. So we’re going to start with the foundation.” Kate started rubbing some lotion on his face. He tried to follow along with her tutorial, but he was too distracted by the ringing in his ears. He wondered what his wife was currently doing. Was she going through a gender transformation as well? Would they put her in a suit and slick her hair back and make her talk with a deep voice? And then what? Were they just going to role-play all week, pretending to be each other? It seemed so obvious and so lazy.
When he zoned back in, his makeup was nearly finished. Kate was rubbing some pink lip-gloss on his lips and Ta
nia was fitting a blonde wig on his head. She spent a few minutes styling the wig, trying to make it not look like a wig, and she was fairly successful—it didn’t look half bad on his head. In fact, he didn’t look half bad as a woman, with all of that makeup and hair and those fitted clothes. He stood up and felt the cool ocean breeze teasing under his dress and up his legs. It wasn’t the longest dress—not even reaching his knees. It was shorter than every pair of shorts he owned, so naturally he felt exposed. “This is silly. Explain to me how this will make my wife remember that she loves me,” Boone said.
“Just trust the system, Mr. Parker,” Kate said, giving him a slap on the tush. Both of the girls started laughing.
“Okay, so where is she? Can I see her now? We have a lot to talk about.”
“No, not for a few more hours, Mr. Parker. We still have lots to work on. We need to practise your voice and your mannerisms. You might look like a lady, but you certainly are nowhere near acting like a lady.”
Boone closed his eyes and sighed. He was already humiliated enough—now he had to talk like a girl too?
The rest of that day was spent practising tedious tasks like walking in heels, repeating silly lines of dialogue, sitting upright at the table, crossing his legs—they even made him practise checking his nails. Apparently there’s a feminine way to check your fingernails and a masculine way. Boone thought it was all nonsense, but he played along.
And then something embarrassing happened. While the girls were showing him how to properly take off his dress and put it back on (because there is a masculine way to change clothes and a feminine way apparently) he noticed his reflection. He saw himself in that little lingerie one-piece and his heart stuttered. He really did look good, even though he was missing a bust.
“That is going to be a problem, isn’t it?” he heard Kate say. Then he looked over and saw that both girls were looking at his crotch. So he looked down at his crotch and saw that he was becoming erect. He quickly covered himself, as if they hadn’t already seen everything.
“Sorry,” he said. “I don’t know why that’s happening. I’m very tired. And you’re both in those little tops—not that I was looking, but how can a man not notice?”
Kate shook her head. “Don’t be embarrassed. This happens all the time. Just rub one out and you’ll be fine—or we’ll be dealing with this all day.”
Boone laughed. He felt blood rushing into his cheeks. “I’m not going to rub one out,” he said.
“Sir, please just do it. It will make all of this go by much faster. We have places to be tonight too, you know. We can even help you if you’d like.”
“W—What do you mean?” he asked.
Then Tania walked up behind him. “Maybe we can make it into a learning exercise. While we get you off, try your best to imitate a woman. Come the way that your wife would come if you were fingering her. You do finger her, right?” Tania reached around and buried her fingers into his lingerie, grabbing onto his erection. She grabbed it firmly, making him perk up. Kate stood in front of Boone, looking into his eyes. “Go ahead,” she said.
Tania started to rub. Boone’s heart was pounding. Now he had no idea what was happening. Was this some strange test or were they really trying to train him? It all made no sense, and it was all happening too fast. Boone closed his eyes.
“Does that feel okay?” Tania asked as she began to rub the palm of her hand up and down the underside of his hard shaft.
“Yeah. It feels good. But I’m married. I have a wife. I love my wife.”
“We know, sir. We’re trying to help you.”
She kept rubbing, pressing down hard with her soft hand. It felt good—too good. He started to squirm as his legs began to tremble.
“Pretend to have an orgasm the way your wife would. It’s important. Every good woman knows how to fake an orgasm.”
Boone took a deep breath. He felt so stupid, but he needed to play along. He started to moan.
One of the girls took his hands and placed them on his breasts. “Get your whole body into it,” she said. So he squeezed his flat chest and gently began to sway as he tilted his head back. He continued to moan.
“Your pussy is so tight,” one of the girls whispered into his ear. “I love fingering your tight, wet cunt.”
Boone’s heart skipped a beat. The girls sounded so ridiculous, but it was strangely arousing at the same time. “Shit,” he muttered.
“In your girl voice, beautiful,” one of the girls said.
So he tried to repeat himself with his girl voice. “Shit.” He knew he sounded outrageous, but he kept going anyway. It was actually kind of nice, having his erection rubbed. It wasn’t something he’s ever had before—with Tania rubbing his tip as if it was a clit. His legs buckled slightly and then a jolt of warm euphoria was sent up his spine. “Oh shit,” he said. “I think I’m going to come.”
One of the girls cupped their hand at his tip, ready to catch his cumshot so that it wouldn’t ruin the lingerie. The other girl continued rubbing, bringing him closer and closer to the real orgasm. He let his head fall back and then he let out a long groan. He felt his cock unloading, filling up the palm of her hand.
Then, once he was finished, he opened his eyes and saw that Kate was holding his cum in front of his lips. “Suck it up and swallow it.”
He slapped the hand away. “Get that away from me,” he said. “The two of you are sick.” He felt his face turning a dark shade of red as he reached down and pressed his cock back into his lingerie. “Now I did what you wanted me to do—so let’s get this over with.”
And after a moment of silence, they were right back to practising all of the silly little exercises that would apparently make Boone more ladylike. This went on for hours, and then finally the phone rang. “It’s dinnertime,” said Kate. She turned to Tania. “Do you think she’s ladylike enough?”
“As close as we’re going to get for the day.”
“Well, Mrs. Parker. It was fun. We hope you enjoy the rest of your trip. I hope you were paying attention while we were doing your makeup because I wasn’t kidding when I said they will kick you off the resort if you don’t do your makeup in the morning.”
Boone’s heart skipped a beat. He hadn’t heard her say that—she must have said it while he was zoned out. Would they really kick him off the resort if he didn’t do his makeup? And what if he didn’t talk in the silly girly voice with his wife? What if he didn’t sit up the way they told him to sit up, or to cross his legs the way they told him to cross his legs? What if his wife took one look at him all dolled up and she realized that he wasn’t the man for her? What woman would want to be with a man who could put on a wig and a bit of makeup and look exactly like a woman?
Boone’s heart fizzled down into his stomach. He had a feeling the humiliation was just getting started, and it was destined to end in divorce. All he could do was hope that Lacy would see him and know that he was humiliating himself for her.
“Let’s get you to your dinner,” said an unfamiliar voice. There was an older woman standing in the doorway now, wearing a long black dress as if she was on her way to a fancy event. Boone awkwardly followed her down a long path. His heart was pounding. He still had no idea what they’d done with his wife. And he had no idea what his wife was expecting from him—or what the resort was expecting from either of them.
CHAPTER V
Lacy was already seated at the small terrace overlooking the ocean. And she looked just as Boone expected, with her hair tied back into a tight bun, wearing a dress shirt and slacks and dress shoes. Boone couldn’t help but roll his eyes. She didn’t even look like a man—she just looked like a pretty woman wearing men’s clothes, but the fact that the clothes fit her made them simply look like off-beat women’s clothes. But he bit his tongue and didn’t say anything, hoping that the resort staff would drop the gender swapping nonsense as soon as they realized it wasn’t doing whatever it was they were hoping it would do.
“You look nice,” Lac
y said as Boone got himself seated. She was trying to use a slightly deep voice, but it was far from convincing. It was strange—for Boone, they’d actually tried to make him into a woman. They spent a whole hour perfecting his makeup and shaving away his body hair. But for Lacy, it seemed like more of a game than anything. It almost seemed like she was doing a bad impression of Boone.
“Thanks,” Boone said with his lips pressed thin. He hated using that female voice, but he could feel the presence of one of the resort workers behind him, and he knew that they were listening and judging. “You look… different,” he said. “I prefer you in a dress.”
“You would, you lesbo,” she said, picking up her menu with a smirk. And is that why they flew halfway across the country? Is that why Boone shelled out ten thousand dollars? So they could just goof around?
Boone looked around and noticed a black glimmer on one of the pillars holding up the roof. It was a camera. They were everywhere—and they were probably in Boone and Lacy’s room as well, which meant no sex and no fun. Apparently, this was going to be a week of silly playtime therapy.
Boone leaned forward “So did they glue some hair onto your chest?” he asked. “Maybe they scooped my hair up and just stuck it to you.”
Lacy looked around and then leaned forward. “You aren’t supposed to be acknowledging our actual genders,” she said. And then Boone remembered one of the little blonde girls saying something along those lines.
He laughed. “Seriously?” he said. “We’re going to do this all week?”
Lacy looked into Boone’s eyes. “Do it for me,” she said. And those words reverberated down Boone’s spine and then splashed in his gut. They chilled his skin and made him feel small and afraid. He had to do it for her. He had to swallow his pride and pretend to be a woman, even though he felt so ridiculous. From that moment on, he was a woman, and she was a man as far as he was concerned.
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