Remaking a Boyfriend Pt. 05: Day One

Remaking a Boyfriend Pt. 05: Day One

Ray batted his eyes open to light streaming in through the bedroom window. Allison wasn't in the bed beside him, he assumed she was already awake. His mouth felt sour and sticky; he could still taste the drinks from last night, including the special final one. He rolled out of bed groggily and stumbled into the bathroom.

There, he found a note taped to the mirror above the sink.

"Morning sweetie! I have a special day planned for you. Start by shaving everything below your eyebrows in the shower. -A"

Below the note was a brand new pink women's razor and a can of fruit-scented shaving lotion. Ray stared at the razor apprehensively for a couple seconds before grabbing it and turning on the shower. He let the water heat up, and stood there for a while letting the hot spray massage his body. After washing himself carefully with a loofah and Allison's body wash (his own body washed seemed to be missing, he noted) he carefully applied the shaving lotion to his legs and began running the razor slowly over it. It took some getting used to at first, but after a few minutes he seemed to get the hang of it. In fact, Ray started to really enjoy the feeling of the blades running over his skin, leaving a smooth lane of flesh in its wake. It took two passes on his legs to get them completely smooth, and he only nicked himself once around the ankle.

After that, his arms and chest (which had very little hair anyway) were easy. He took extra care going over his private areas. After a few cautious attempts, he found that pulling his skin taut made everything easier. Finally, he quickly gave his face a once over.

He stepped out of the shower and examined himself in the mirror. He ran his fingers over his body, and felt both excited and a little nervous at the extreme sensitivity of his shaved skin. He opened the door to the bedroom to find another surprise.

Allison had laid out an outfit on the bed, complete with another note:

"Hi Baby! I want you to put these on for me. I know it's a little different but I think you'll look great. Come out when you're dressed, I'm making breakfast! -A"

Assembled on the bed were his chastity cage, a pair of women's jeans, a lacy black pair of panties and matching bra, a t-shirt in a women's cut, and a pair of sandals with a two inch heel. Ray studied them for a few seconds before sighing and grabbing the panties.

After closing the lock on his cage, Ray reached for the panties. The black lace felt incredible sliding over his newly smooth skin and made him a little aroused. He adjusted his caged cock as well as he could, until he felt this bulge was as small as he could make it. He put the bra on next, trying to copy what he had seen Allison do every morning. After a couple false starts, he got it hooked properly and adjusted the straps to what felt right. It had some thick padding inserts that gave him the appearance of small but noticeable breasts.

He went to the mirror on the closet door and examined his appearance. It was an odd sight—he looked like himself, but the mere presence of the bra and panties highlighted all the latent femininity in his features and frame. The long hair, the narrow shoulders—he didn't look like a super model, but he looked plausibly female. The thought was scary, but also a little exciting.

Next he put on the jeans, surprised by how tight they were. For a minute he thought he wouldn't get them on, but after some wriggling he finally got them over his hips and zipped. The tight pants pushed his caged dick between his legs in a way that was uncomfortable, but the bulge wasn't noticeable unless you were really looking for it. After that the t-shirt was easy. The shoes weren't so bad—he didn't have too much trouble balancing, but it was uncomfortable to walk on them and he could tell that it would take some getting used to. After a quick check in the mirror (he really kind of looked like a girl! At least from a distance) he walked out to the kitchen.

Allison's face lit up when she saw him. "Oh my god, baby, you look amazing! Come here and do a turn for me."

Ray walked closer and spun around slowly, his ears burning red with self-consciousness.

"Everything fits so well! Your butt looks amazing in those jeans, and that bra makes it look like you have nice little boobs! All that exercise and diet really paid off, huh? Oh my god, we're going to having so much fun with you." She tugged at the waist of his pants and revealed the top of the panties. "Ooooh I can't wait to see you in those!"

Ray blushed and smiled at her compliments. She had never fawned over his appearance like this before.

They sat down for breakfast. Allison had made them fruit and yogurt parfaits, and of course a smoothie for Ray. He felt weird about drinking it now that he knew about the "special ingredient", but he figured he had already had dozens of them, so one more couldn't hurt.

After they finished, Allison said that she had a present for him presented him with a small velvet box.

"It's a small gift, but an important one," she said. She watched excitedly as he opened it.

Inside was a small gold necklace with a tiny gold design hanging at the end. Ray examined it and saw that it was script lettering.

"Rachel," he read off with a tone of confusion. He looked at Allison quizzically.

Her grin spread ear to ear as she nodded at him. Suddenly, it clicked for Ray. He was Rachel. Even though he was already wearing women's clothes, the thought of having a female name really struck home for Ray what a huge change this would be. His mind churned as Allison placed the necklace on him and did the clasp in the back. The gold letters sat neatly below his clavicle, above the top of his shirt.

Ray looked up at Allison who, who had her hands clasped in delight. "Thank you, it's beautiful."

"Yeah? You like it? I think it suits you."

Ray nodded.

"Ok Rachel, now get to the bedroom. We have work to do!"

It was incredibly weird hearing Allisons use his new name, and Ray felt like things were moving too fast. But he didn't object, and comforted himself that he just had to make it through the next few days and then all this could go back to normal.

In the bedroom, Allison sat him down in front of the vanity.

"Now, we're just going to but a little bit of light makeup on you for an everyday look. You'll learn how to do this soon enough, but for now I'll show you the ropes."

Ray sat like a statue as Allison expertly applied blush, mascara, eyeliner, and a lip gloss. At each step, Allison explained what she was doing and the proper technique for application. Ray tried to take it all in, but it seemed like a lot to remember.

Finally, Allison stepped back and let him look at himself in the mirror. Ray gasped. Staring back at him in the mirror was someone who was recognizably him, but was also 100% a woman. His cheekbones, his lips, his eyes—all traces of masculinity were hidden. And more than that, he was pretty. "Oh my god," he whispered.

"I know! You look amazing, baby," Allison beamed.

Ray turned his head side-to-side, silently admiring himself in the mirror.

"Now, let's get going! We have an appointment we can't miss!"

"What? You... you want me to go outside like this?" Ray's heart started pounding with anxiety.

"Duh! You look amazing, of course I want to show you off!" Allison replied. "Besides, for this weekend to mean anything you actually have to try living as a woman, not just dressing up in the house."

"But what if someone recognizes me?" Ray objected.

"Like who? Who are you worried about? You don't have a boss or coworkers. And besides, even if we did run in to someone you knew, I doubt they'd recognize you."

Ray realized that she was right: he didn't actually much to fear. Still, he felt tremendously self-conscious as they stepped out of the house and got in the car. Allison drove them to a local strip mall, and parked in front of a nail salon.

"Now, you can let me do all the talking in here. You don't have anything to be embarrassed about, but it is true that your voice might give you away. We'll work on that, but for now if you want to say anything, just use a high-pitched quiet voice."

Ray nodded. "Like this?" he said, attempting to follow her advice.

"That's a good start. Now, let's have some fun!"

They strolled into the nail salon and Allison spoke to the receptionist about her reservation. Ray glanced around nervously, expecting that everyone would be staring at him, but nobody seemed to notice or mind him. After a minute he began to relax and convince himself that he really did look enough like a girl to pass for one.

The receptionist led them to adjacent chairs. Two manicurists came and immediately started working on them. Ray felt a little uncomfortable as the woman grabbed his hands and began trimming his nails, but she seemed to know what she was doing. Allison gave them instructions on shape and color for the both of them, and Ray just nodded. The women didn't speak much English, so he felt no pressure to engage them in conversation.

A few minutes in, Ray actually started to enjoy the process. It was nice to be taken care of this way, and he and Allison traded happy glances at each other while the women worked. They got manicures and pedicures—Allison chose a dark purple color for herself, and a crimson color for Ray. After they were done, Ray marveled at how feminine his fingers and toes looked with nail polish on.

After that they got lunch at a little cafe, and went through a nice stroll through a nearby park. Ray was getting increasingly comfortable being in public by the minute. While they were walking, they passed two guys throwing a football. One of the passes sailed long, and the ball ended up near Allison and Ray. When the guy jogged over to get it, he smiled at them and waved.

"You girls having a good weekend?"

Ray's face turned a deep crimson at once again being taken for a girl by a man.

"The best," Allison responded cheerfully.

"My friend and I are going out to a party later, any chance you'd like to come along?" the guy asked. He was clearly being flirtatious.

"That's so nice of you, but we have plans for tonight."

"Alright, well, our loss." The guy smiled, looked directly at Ray, very obviously moved his eyes up and down Ray's body, and winked.

Ray's heart was thumping as they strolled on until they were out of earshot.

Allison gave him a devilish grin. "I think he liked you, Rachel."

Ray's mouth was completely dry. "No, he must have been looking at you."

"Oh come ON! You're not that dumb. You look hot! You need to get used to it, this is what it's like to be an attractive woman. Male attention is one of the big perks."

They sat on a park bench near a pond and talked for an hour or so. Allison had Ray practice speaking in a female voice as they chatted about work, and the news, and movies. Eventually Allison returned to the obvious topic of the day.

"How are you feeling so far?"

Ray though for a second. "There are some parts that have been a little strange, but it's kind of amazing how comfortable I feel. Like when we were talking just now, everything felt really, I don't know, natural?"

Allison smiled.

"I mean, I'm still not sure about the whole permanent thing," Ray continued. "But so far today has been nice."

Allison reassured him that he wouldn't have to make any decisions until Monday night, and that there was still plenty in store for him that would help him figure things out.

They returned home, and after doing some yoga (the women's yoga clothes now being totally appropriate), Allison informed him that they would be going out.

He showered again, and this time when he got out Allison had a new outfit for him on the bed. Again, there were a lacy pair of panties and a padded bra, but there was also a short, sparkly silver dress, and a pair of black high heels. The dress looked impossibly small, like it would barely cover anything.

"There's no way I can pull that off!" Ray objected.

"Well, we do need to make one adjustment, it's true," Allison replied. She took the key off her anklet and unlocked Ray's cage. "Now that your piercing gauge is big enough, we can give you a more discreet cage." She produced a new contraption from the drawer, this one a wire mesh cage that fit only over his cock with no ball trap. At the end was a hook shaped piece that was designed to go in his Prince Albert piercing, and which screwed in with a special key.

Allison quickly replaced his old cage with the new one. It fit extremely snugly, and prevented his limp cock from expanding at all. No matter how much he pulled, the piercing held the head of his penis firmly "There we go, that you should give you some more freedom. Now you should be able to tuck that little guy between your legs and it'll give you a nice, clean line for your dress." Allison helped him into his panties, positioning his locked penis between his legs and tucking his scrotum back as well as she pulled the silky fabric into position. They fit snugly, and held his balls and dick firmly between his legs. "How does that feel?" she asked as she replaced the old key on her anklet with the new one.

Ray walked around a little to test. "It's a little uncomfortable but I think I'll get used to it?"

Allison nodded. Next came the bra, which again gave Ray the appearance of small breasts. Then she helped him slip the dress over his head. It felt incredibly skimpy—the thin straps at the top left his shoulders and upper chest completely bare, and the dress fell at his upper thigh, leaving what felt like miles of his legs completely exposed. He'd seen Allison wear bathing suits that were more modest than this.

They both gazed at him in the mirror. "Amazing! You have such a beautiful, girly figure Rach!" Allison gushed. Ray just nodded. He did have nice looking legs, he had to admit.

Allison sat him down at the vanity once more, and this time spent half an hour giving him a complete face of makeup. She gave him a sparkly, dark eyeshadow, heavy blush, a deep red lipstick, and even some light contouring. She also teased his hair and used some hairspray to give it more volume. As she got close to finishing, she purposefully blocked the mirror so that he couldn't see himself. When she was done she made him close his eyes, led him in front of the full-length mirror, and guided him into his shoes. The ultra-high heels felt very unnatural, and Ray wobbled a little before steadying himself.

"Now, Rachel, open your eyes," Allison commanded.

Ray obeyed, and his jaw immediately swung open. Staring back at him was a complete fox. A tall, slender woman, dressed to kill, with incredible legs, a toned body, and gorgeous features. He turned his head side to side. He was hot! He felt his dick stirring in his panties, straining against the new cage enclosing it. He narrowed his eyes and pursed his lips, trying out the "fuck me" look that had smitten him so many times before. "Holy fuck!" he said finally.

"I know, baby! I sure you would look good, but I had no idea you would look hotter than me." Allison poked him in the ribs jokingly.

"Oh stop, I'm hot but I'm not that hot."

"We'll just see who gets more attention at the club tonight."

Ray's heart did a flip-flop at this news. Walking around outside earlier had been fine, as he wasn't trying to attract attention. But dressed like this, in a nightclub, he'd be the center of it.

Allison got ready quickly, throwing on a red miniskirt and a black off the shoulder top. She did her makeup, gave Ray a couple of her simple gold bracelets and a spritz of perfume, and they were ready to go.

"Wait, one last thing, let me get a picture of us hotties," Allison said.

She and Ray posed in front of the mirror, trying out a few different positions. Ray was amazed as Allison scrolled through the photos. He could tell that his posture wasn't perfect yet, but in a couple photos he looked just like the kind of hot young women he drooled over on Instagram.

They took a shot of vodka to get the night started, and Allison ordered them a car. The driver dropped them off outside one of the trendiest nightclubs in town. There was a line outside, but Allison strolled to the front and gave her name to the bouncer. He eyed them both lecherously as he let them through. As they entered, Allison whispered in Ray's ear.

"It'll be loud in here, so if you need to talk just keep your voice high-pitched and no one will notice anything. You don't have to do anything you're not comfortable with, but I want you to have fun and really give this a try."

Ray nodded as they passed from the dark entryway into the main room lit by many different moving colored lights. Music throbbed, and there was already an enthusiastic crowd on the dance floor. The hostess led them to the small booth near the bar that Allison had reserved.

Allison got them some girly drinks from the bar, and for a while they drank and scoped out the scene. There were plenty of beautiful people in the club that night, but Ray could tell that he and Allison were turning heads. Men were already sneaking glances at their table.

"So, who're the hottest guys here?" Allison asked matter-of-factly.

Ray slowly surveyed the room. "I think it's striped shirt, rolled sleeves and his friend in the green. Across the room to my right."

Allison took a quick look at the guys Ray had identified.

"Oooh. Great choice. I agree. Which one do you think is hotter? Striped shirt?"

Ray blushed. "How did you know?"

"I don't know, he just seems like the kind of guy you think is handsome. Clean cut, built. Really masculine."

Ray shrugged. "I guess so."

"Do you think we can get them to dance with us?" Allison asked with a smirk.

"Wh... what? I don't want to dance with a guy! I can't dance with a guy! He'll totally know I'm..."

"Oh, stop! First of all, there's no way he'll know. Just keep your legs together and face away from him when you're close together and he won't feel anything unusual. And what do you mean you don't want to? It's what girls do, and it's fun! You have to do it if you're really giving this a try."

"Ok, fine, but even if I wanted to, there's no way they'll dance with us. They're already talking to girls over there."

Allison's eyes sparkled as a smile spread across her face. "Rachel, those girls are sevens. We're tens. Finish your drink and come with me."

With that Allison slammed the rest of her cocktail. Ray did the same, heart pounding as Allison grabbed his hand and dragged him across the floor. They stopped a few feet away from the guys, and Allison started dancing, wiggling her hips seductively. Ray tried to follow her lead.

After less than a minute, Ray saw Allison catch the eyes of the guy in the green shirt. Like a shark, Allison snapped at the opening. She smiled at the guy and edged closer to him.

"Hi, I'm Allison, and this is Rachel! What're your names?" she shouted over the music.

The guy in the striped shirt turned from the girl he was talking to and looked at Allison, and then at Rachel. There was a clearly a second of calculation for both men about whether they should respond to Allison or continue talking to the other girls.

"I'm Kyle," the guy in the green shirt responded.

"And I'm Steven," added the guy in the striped shirt.

"Nice to meet you guys! We're celebrating tonight, it's Rachel's birthday!"

The double entendre made Ray blush. At this point Kyle and Steve had clearly turned away from the other girls, who were staring daggers at Allison and Ray.

"A birthday? That calls for shots!" declared Steven.

Ray shook his head emphatically, but Allison was already yelling in agreement.

It seemed like Ray only had time to blink, and Steven peeled off to the bar. Kevin directed a question at Allison that Ray couldn't hear, Ray noticed that when she answered she placed her hand on his shoulder and squeezed gently. It was still strange to him to see her be so flirtatious with other men, but it was clear that she found it fun.