Ruby

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“Ruby”

17-year old Rob was ready for his first examination of tenth grade. He wasn’t nervous at all. He had been a star in his school throughout and was already expecting top rank again. But thanks to his studious nature, he almost forgot to make any friends in school except a girl in the neighborhood who he usually shared notes with. So Rob was headed for school on the first of his last 7 days in tenth grade. Mom took a second, kissed on his forehead and while wishing him all the best took a lock of hair falling on his cheek and tucked it behind his ear. “You should consider cutting your hair, honey. Are you sure they won’t trouble while writing your papers?”
Rob pushed his mom’s hand away, put his half eaten sandwich back in her other hand and left waving at her without even looking.

In the exam hall, he was a few minutes early today. So he was waiting at the desk with his enrollment number on it when he felt a tap on his shoulder. He looked back over his shoulder to find his neighborhood friend Monika sitting behind. (Monika was not one of the most beautiful girls in the school but her cuteness had something magnetic about her. She was about 5’ 5”, a decent figure with long blond hair that added to her ‘i-don’t-wear-makeup’ look. Rob had met her the day he and his mother moved into her neighborhood. Monika’s mother volunteered to help them get settled and the lonely boy Rob found someone he could call a friend.) “Hey gorgeous! You are early. Nervous? All the best!” Rob missed everything she said after the word ‘gorgeous’ and then without bothering to ask, just smiled and then again turned towards the examiner. “Did she just call me gorgeous?” he thought but his thoughts were interrupted by the examiner as she handed him an answer sheet and a question paper. He was so engrossed in mentally analyzing the compliment or remark that he didn’t even realize when it became houseful. Keep aside his thoughts, Rob focused on the paper and smiled with confidence like it was going to be a cake walk. But like mom doubted, his hair was already troubling him. Each time he tucked his hair away from his eyes, a lock would fall out again. And it was clearly reducing his writing speed. “Any problem, Rob?” asked someone when he looked up to find the examiner Miss Jameson standing next to his seat. At almost 45, Miss Jameson had still maintained her body like she was just in mid-thirties. She was tall and her high heels made her look even taller. In her turquoise color satin silk blouse with short puffed sleeves, a black silk scarf, a tight black pencil skirt, black pumps with 6” heels, her hair tied back in a tight bun sparing a lock to tickle her left cheek, her chic rectangular turquoise color frames and no makeup except a thick coat of creamy red lipstick, she was looking ravishing without overdoing anything. She had all the curves a woman wants and Rob was lost in them when she cleared her throat bringing him out of his fantasies. “Do you need help?” she said and Rob just shook his head and continued writing.

Soon Miss Jameson announced that only 30 minutes are left. Rob was still struggling with his hair. After taking a few trips to and from Rob’s desk, Miss Jameson came to Rob’s desk and asked him to stop writing and stand up. Rob was getting nervous now as he still had a lot to write and thought that Miss Jameson probably doubts that he is cheating. But he saw that she had her purse in her hand from which she had taken out a shiny Swarovski-studded turquoise colored barrette. Before he could speak, she held Rob’s face by his chin and turned it towards her. She took the shiny barrette and secured Rob’s hair to the side with a click. She then took out a simple black clip with a fewer stones and secured the hair on the other side in similar fashion. Rob’s hand went for the barrette when Miss Jameson slapped his hand saying, “Just leave it and get back to writing if you don’t want to sacrifice your top rank worrying about your hair.” The exam bell rang in no time. Monika tapped his shoulder again. “How did it go genius?” Rob was smiling but he was clearly not content. He couldn’t write all of it.

He was walking home when he heard a car horn. He looked to his left to find Monika and her mother in the car. They offered him a lift and Rob couldn’t refuse even though he wanted some alone time. In the back seat of the car, he was still looking at the question paper in his hand when Monika said, “Hey Ruby! You didn’t tell me how did it go?” Realizing that she was addressing him with a girl’s name, Rob gave her a look that clearly meant ‘shut up’. But that couldn’t keep Monika giggling all the way home. Suddenly, Rob found her staring at him. Before he could ask her to mind her own business once again, Monika pointed at his lips saying, “Your lip is bleeding. It’s cut because of cold I think.” She put her hand in her backpack and pulled out a lipstick sort of tube. “Here, it’s just a plain gloss. It will moisturize your lips and stop bleeding.” To sound more convincing, she added, “Even my dad uses it at times.” Rob was anyway bored with her addressing him like a girl since morning. So to end it, he reluctantly took the tube and applied a coat. Soon Monika’s mother announced from the front that he is home. Rob thanked her for the ride and went inside. He dropped the bag on one side of the couch and threw himself on the other. Mom was in the kitchen and asked from there only. “Hey honey! How was your exam? I have made your special all cheese burger. My boy must be starving.” Saying this she came out holding a big fat burger in a plate when she stopped in her tracks. “Oh my darling! You look so cute in that hair style.” Rob opened his eyes and from his mother’s expressions suddenly realized that he was still flaunting Miss Jameson’s barrette. He quickly reached for it to pull it out when his mom stopped him. “Oh come on! Let me take a good look first.” She took his son’s slender hand into her own and pulled him up to his feet. She was about to hug her when she again stopped and said, “I didn’t know I have such a beautiful daughter too.” She took him into a tight hug. “Nice lipstick too, honey. I have just the matching ear rings for you.”
Rob now recalled how Monika had offered him her lipstick calling it a gloss. He tried to escape his mom’s embrace but she tightened it further. “I am so happy! We can now go get pampered together. Parlor, shopping, spa and what not. Rob was now too embarrassed and wanted to explain, if only she will let him to. But Venessa seemed too happy to have found a daughter. After almost shedding a few tears, she let go of him. Rob was telling her what happened when Monika walked in. “Hey Ruby! Hello Miss Jameson!” Rob gave her an angry look when his mom asked him to be nice. “Rob, is that how I taught you to receive your guests? Now be a good girl and make some space for Monika to sit.” Rob was now getting irritated as his own mom had now joined Monika in the mocking. He was about to leave the room when his mom again said something to add to his embarrassment. “Ruby honey, would you be a darling and make some tea for your friend and your mother?” Rob was about to scream when she added, “I almost had to drive to the other end of the city to get the ingredients for your special cheese burger. And I am too tired or I would have made it myself.” Rob was smart enough to understand the clever usage of emotions by his mother but he thought it’s not a big deal and could do at least that much for her. While all this was happening, Rob again forgot that he was still wearing the barrette, the other clip and the lipstick. Monika had given him a special kind of gloss that changes its shade to a light pink once it is exposed to air for some time. Monika and Venessa were not in the living room when Rob came out with the tea. He kept the tray on the table when he heard them giggling inside the bedroom. He followed the voices and found them in his own bedroom looking at a few skirts of different styles and lengths laid out on Rob’s bed. He knocked the door to announce his arrival. Venessa made him sit down as well. She had an old photo album in her hand, one that even Rob hadn’t seen. Inside, were a lot of pictures of younger Venessa with a little girl dressed in colorful frilly frocks and dresses. “Who is this girl with you in the pictures, mom?” asked Rob. Venessa looked at him and smiled. Just then Rob saw the little girl, in one of the pictures, sitting on a red chair which he now remembered seeing in their store room. Rob held his breath and said, “Mom, please don’t tell me that…”. He couldn’t complete his sentence, when mom almost cried and said, “Yes, my dear. It’s you. That little girl is you.” Monika couldn’t help giggling all this while as if she knows the entire story already. Venessa tried to hug Rob but he pulled back and she continued… “When you were about to born, I was expecting a girl since I had been getting signs and feelings all through my pregnancy period. Not to say that I was happy to be gifted with a gorgeous son like you. You were softer and thinner than boy children your age and were more like cute as the little girls I used to notice in the neighborhood. And since my first wish was to have a daughter, I thought it won’t do any harm to you or to myself if I try and dress you like I would have pampered my daughter. And that feeling made you even more special. I used to get boy stuff for you but mostly I would get dresses and frocks for you. You looked so cute in them that I almost forgot I have a son and not a daughter until you grew up a little and started going out to play with other children. Since you were a late walker, you almost spent the first 5-6 years of your life in frilly satin frocks, colorful dresses and skirts. In fact, you attended first three years of your elementary school as a girl. Then your school informed me that the name and all the details on your school form will become permanent after 4th year. So I controlled the mother in me and put you in an all-boys school. And I am proud that you have turned out to be a great son and a great human. It’s just that when I saw you today in this cute hairstyle and wearing lipstick, it took me back to those wonderful years when I thought I had a daughter and pampered you like a daughter should be. So I stopped you from removing the barrette and the lipstick.” Venessa was completely in tears by now and Rob didn’t know what to do, so he hugged his mom tightly and said, “Sorry, if I was rude mom. It’s just that it’s embarrassing.” Venessa interrupted him again… “But sweetheart, you have always had long hair. That’s the way you like them you said. And that’s why you haven’t cut them in long time. What difference a barrette will make? Besides, it will keep your hair tied and out of the way when you are working and you can keep them loose when you are not doing anything.” She took his chin gently in his hand. “For now, all I wish is if I could get to spend this weekend with my daughter like before.” Rob was about to argue when she shut his mouth putting a finger on his lips. “Shhhhh… Just one weekend honey. I promise I won’t go too far and that you will love it. And I promise I will never ask you for anything like this again. Just one last time gorgeous, only for your mommy.” Saying this she took the barrette out of his hair and started brushing his hair. Rob was like frozen in time and was still thinking when Venessa finished brushing his hair, tied them in a high pony tail with a satin turquoise ribbon and secured the sides with the same barrette, only a little tighter this time. So Rob could feel the barrette and the clip pulling at his hair all the time. Rob was about to take a look into the mirror but Monika had already covered it with a sheet. Venessa kissed him on his cheek and said, “I think we need a retouch here.” And she pulled out a long tube similar to the one Monika had given Rob, only that this one was clearly bright pink. Rob leaned back only to be stopped by Monika. He was about to object when Venessa wiped a tear sitting on the edge of her eye. Rob closed his eyes praying all this was a bad dream but it wasn’t as the creamy sating texture of the lipstick brought him back to attention. Though Venessa didn’t go for an extra coat, Rob found his lips heavier and hard to detach each time he closed his lipstick covered lips. The stickiness made the realization even stronger. Mom then produced a black A-line satin skirt. Rob now jumped off his seat but Venessa pulled him down. This time she gave him a stern look as if he is being selfish and annoying her now. “Come back her young lady or I will make sure that Monika tells all your other friends that you loved skirts and dressed so much that you attended school as a girl and then requested me to put you in an all-girls school. Or be my daughter Ruby for next two days and once this weekend is over, you are free to get back to your dirty boy life, playing in dust and getting tanned in sun.”

Rob took the skirt from his mom’s hands and showed her and Monika the door so he can change in private. He had just closed the door when mom knocked. He opened it a little and Venessa said, “Ruby honey, be a darling and change your undies. I have laid a fresh pair on your bed.” Rob opened the door after 5 minutes or Ruby did. It seemed from Venessa’s expressions that even she didn’t know if her son was there 5 minutes ago. Rob was now standing wearing his short black t-shirt, a black A-line skirt that ended a couple of inches above his knees and his hair was tied in a very cute ribboned pony tail and he had matching barrettes in his hair. Venessa was all smiles while Monika was gasping. Both the ladies kissed on either side of his face. And while separating her lips from Rob’s face, Monika paused and kissed him gently on his lips. Both Rob and Venessa were in shock. But Venessa was quick to intervene and pulled Monika back. “Get away from my lovely daughter, silly girl. You are spoiling her makeup. She took a tissue to clean the smudging, pulled out the tube and gave Rob two coats of the lipstick this time. “That’s my pretty Ruby! But something is missing.” And without talking further, she left the room and was soon back with a small wooden box. Inside was some artificial jewelry. She first took out a pair of clip on earrings in the same turquoise shade as the barrette and clipped them on his earlobes. They were artificial but they were heavy and studded with big faux diamonds which had two small diamonds each hanging from the bottom making them tickle Rob’s neck each time he moved his head. Then Venessa produced a necklace of turquoise color beads with a huge faux diamond similar to the earrings hanging like a pendant. Next came multiple matching bead bracelets looking like bangles when worn, followed by a sleek watch with diamonds all around the dial and a sleek turquoise leather belt with a Swarosky buckle around the waist. The tshirt, thought the ladies, is spoiling the look. So without asking Rob, the most girly top was pulled out of the closet. It was a satin silk turquoise blouse with ruffles in the front, a sharp collar, and long puffed sleeves with lace around the cuffs. As soon as Rob put on the blouse, it was decided that without a proper padding, the blouse will look loose at the front. So a black bra was produced. Rob almost started crying with all this already gone too far. But mom Venessa wiped his tears, kissed him and took him into a hug. “Don’t worry dear. You will look great. My daughter is going to stun everybody and make me proud. It’s just a bra. And it helps us women feel complete and confident. Besides, you will never know the real joy of all this without a bra.” And while breaking the hug, she continued. “And the day you have your own breasts; you won’t even need this padding.” Rob was now not just made to wear a bra but taught how to wear one as if he was going to wear it every day now. Once he was shown the trick, he was asked to unhook it and wear it back for several times till he had mastered it like any other woman. So a black bra with extra padding, filled with socks, a turquoise satin blouse and a black satin A-line skirt. By now, Monika had left the room saying that she needs to make an urgent call at home.

When Monika was back, Rob was every inch Ruby. He was now wearing eyeliner, mascara, light eye shadow with mixed hues of black and turquoise, multiple coats of bright pink lipstick and sufficient jewelry to match. Monika came back with a pair of black thin strap sandals with 6” heels. Rob was made to practice in several ways, like swinging his hips, keeping books on his head and what not. It took him about an hour to manage walking around in heels without twisting an ankle. He was now given a muscle relaxant tablet popping which Rob slipped into sleep. When he woke up, his hand and toe nails had already been cleaned, filed and painted in turquoise. His feet were encased in the black heels. Just then the doorbell rang. Venessa shouted from the bathroom asking Rob to open up as Monika must have been back. He stood up to find a silver and turquoise purse hanging across his shoulders to the side of his hips. He remembered his lessons – one foot in front of the other. He cat-walked to the door and got the biggest surprise as he opened it. It was examiner Miss Jameson. She extended her hand to shake Rob’s and said, “Hi! You must be Ruby. And it seems that we share the same taste in dressing. Is your mom home? She wanted to see me to discuss about your admission in tenth grade of our school." She then suddenly smiled checking out Rob from head to toe. "It seems we have a lot in common when it comes to dressing." Rob realized he was wearing exactly the same outfit as Miss Jameson.

To be continued...

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Comments

Too funny!

Hey CJay,

What a sneaky bunch of people that surrounds our new girl? Is mom going to get away with this and how is Ruby going to fair when she really didn't appear to be a TG person or even a cross dresser? Guess that's why you're writing and not us.

Good story so far.

Sincerely,

Santacruzman