Scene 9

Scene 9

Sitting at his vanity, Greg slowly pulled one curler at a time from his hair while his phone sat in front of him in speakerphone mode as he talked to his grandma. His mom had texted him earlier in the day saying how he needed to have his hair curled for his first real date. He really didn’t want to remove his father's baseball cap, but he knew there would be hell to pay if his mom didn’t see his hair all curled like she had taught him.

“Are you excited for your date tonight sweetheart?” Greg rolled his eyes, excited was not the word he would use. Terrified, nervous, angry, those were better words.

“Oh absolutely, but…” Holding one of the curlers in his hand Greg looked over at the black dress hanging on the back of his bedroom door. He had been allowed to get something more conservative, at least compared to what he would like to see a girl in on a date. The collar wouldn’t show the breasts of any girl wearing it, not like he had any, the sleeves would stop just below his elbow and the skirt would come down almost to his knees. Still he was going to wear it, a little black dress that cost over two hundred dollars on a date with a boy, specifically his best friend. His grandma had gone all out to make sure her granddaughter looked her best. It made Greg shiver at how much money she had spent. Over two hundred dollars for a dress, seven hundred and fifty for some red leather stiletto five and a half inch pointed toe heels just because it had some name brand of Louboutin, almost a thousand dollars was spent, and that was before she bought jewelry. It was insane and no amount of him saying he didn’t need it persuaded her to stop. She just kept saying how she had so much time to make up for.

“It sounds like you might be a little nervous. I know this is the first time your boyfriend has taken you someplace nice, but there is no reason to be nervous. You will look spectacular in the clothes we picked out, you just make sure to send plenty of photos of the two of you. If I didn’t have a prior engagement I would be there to see you off.” There was that word again, boyfriend. He hated hearing it in any context related to him. Greg hated having photos to document this humiliation, already he had sent at least two selfies to Marcus everyday this week and now the old bat wanted more proof of this twisted endeavor.

“You know me grandma, I never shy away from the camera!” Acting like the cheerful daughter and granddaughter was tiring, especially when his mother was so insistent he stay in character so they didn’t mess up.

“Wonderful dear, I will let you get ready then. Have fun and I can’t wait to see you and Marcus tomorrow. Love you Genna.”

“Love you too Grandma.” Greg ended the call, then slowly closed his eyes, feeling the weight of the mascara on his lashes. If only this was a dream, a nightmare he could wake up from. The promise of money leading him to dress up like a girl, get blow job lessons from his mom and then to turn around and use what he knew on his best friend. Without opening his eyes Greg pinched the skin on his left hand, the small sharp pain didn’t make the world dissolve, it was all terribly real. Opening his eyes again Greg let out a drawn out sigh. He still had half his hair up in rollers, once those were out he would have to brush his hair out and then ramp up his makeup for a nighttime look. “Being a girl is exhausting.” He told himself while looking in the mirror, like the image of the pretty young woman was going to respond.

Before Marcus arrived Greg, as Genna was standing in the living room as his mother paced around him, checking him out like he was a piece of art about to go up for auction. Without asking or saying a word Cynthia pulled up her son’s dress making sure he was wearing the garter belt correctly.

“Hey! Don’t do that!” Greg said pulling the black dress down as a blush came to his cheeks, he had been dressing like this for little over a week now and there always seemed to be a time he felt humiliated enough to cause him to blush.

“Just making sure you are wearing the garter belt correctly Genna, the last thing you want is to have it on wrong, otherwise going to the bathroom would be a much larger hassle.” Greg, no Genna looked gorgeous, her child was about to get more looks from girls than he ever had before, though that could be said about men, though in a different way. “You look beautiful dear, you did a wonderful job with your outfit, hair and your makeup. I love that you even painted your nails to match your shoes.”

“I would hope I look good considering the old woman spent more money on what I'm wearing today than most people pay for rent.” Moving his right hand up to his ear, Greg felt the wide gold cuff bracelet slide down his wrist as he touched the dangling gold earrings with diamonds and garnets.

“Look at the bright side honey, you can always give away the jewelry as gifts to a future girlfriend.” Cynthia said with a smile as she took in the earrings dangling from her feminized son’s ears. Thinking about how much those alone must have cost.

Greg looked down at his legs, dark thanks to the twenty denier dark stockings, his feet ending in a pair of five and half inch stiletto heeled red pointed toe shoes. He would say it was a miracle he could walk in them, but he had felt the pain from the hard work in order to learn the lessons his mother taught him. “Maybe my next girlfriend will have the same size shoe as me too.” He said thinking about offloading as many of the girly shoes from his closet as he could.

“Hoping to share shoes with her?”

“Yeah… wait no. Umm no so I can give her my stupid ever growing heel collection.” Cynthia didn’t laugh out loud at her flustered child, but it was a near thing. She was going to tease Genna some more about sharing a closet when she heard a car pull up in the driveway.

“Here Genna take your purse, it has everything you will need. Now go run along to your room, I will call you when it is time to come out.”

Greg took the offered little red clutch purse, but looked at his mother confused. “But he is right there, the sooner we leave the sooner this is over.”

“If that little terror is going to treat you like his girlfriend, then he can learn some patience while his girlfriend gets ready like every other man. Now get to your room, quickly now Genna.” Greg minced off to his room, opening his purse to see what she crammed into the small container. There was his red lipstick, lip gloss, a pair of twenty dollar bills, two tampons, three of the rainbow flavored condoms and a travel size container of mouthwash. “Just what every girl needs to be ready for her first date.”

Waiting in his room Greg started to grow impatient as one minute turned into five and no one had called him or knocked on his door. Standing around in the incredibly high shoes seemed like a bad idea, so he sat down, smoothing his skirt out and crossing his legs to wait longer. The five minutes turned to ten and then fifteen before he had enough waiting. Standing up in a huff he opened and was ready to see what was taking so long when he heard his mothers voice.

“I think I just heard her door open, I told you she would be out when she was ready. You can never rush a girl.” Greg scowled, but took a moment to center himself, he didn’t need his mother pulling him to the side and reminding him how a girl should always be smiling. He had been smiling so much that his cheeks didn’t even bother him anymore and it was becoming much more of a default expression for him, despite how he actually felt. Putting one high heeled foot in front of the other he came out into the living room. He expected his friend or ex-friend to be smirking at him, but instead found Marcus dressed in a black pair of slacks and jacket, with a red shirt and black tie and a look on his face like he had just watched a Hollywood starlet cross his path.

“Wow.. your… wow!” For just a split second Greg found himself appreciating the statement or lack of one. He had spent a long time getting his hair to have just the perfect wavy curls, getting the making to look just right. Even if he didn’t want to put in that kind of effort for a date he didn’t want to be on, it was nice to have his efforts so obviously noticed.

“Just wow?”Greg lightly touched his own cheek, feeling the warmth from a light blush that he really wished he could control.

“Umm yeah, I mean no. Genna you are breathtaking!” Marcus didn’t see any sign of his old friend, just a gorgeous girl. Stepping forward he wrapped one hand around her and went in for a kiss when she held her hand up, touching her fingertips to his lips.

“You are going to ruin my makeup, and Grandma would like some pictures of us.” Marcus didn’t let go of the girl, just looked at her for half a second smiling.

“Can’t disappoint Grandma Brandi.” He said with a wicked smile, knowing all of this revolved around Greg’s Grandmother.

The two stood posing and smiling as they had photos taken, Greg was the only one not happy about the results. Marcus was thrilled to have a girl so beautiful at his side, regardless of how it happened. While Cynthia had to admit the two made a cute couple. She had gotten used to seeing Genna around and she was much easier to deal with than Greg. It was awkward for her to be showing her child how to use a dildo to please a man, but it was also a fantastic change of pace to have Genna help with the dishes or vacuuming the house while she was gone. Something she was never able to get Greg to do. Though even if she was enjoying having a daughter around she was not a fan of Marcus. “Well you two have fun tonight and I do love how you dressed to match.”

Marcus smiled, giving a light kiss to his date's cheek. “She was excited about her heels when she got them and sent me a photo, so I dressed to match.” He said knowing it was more of him telling Greg to send him updates on all the girly things his grandmother was buying him. He knew the shopping trip had to be ****, but he wanted her money. She was giving it to him, just not the way he would like he was sure.

“Did she now?” The idea Greg was showing off the shoes he was going to wear on the date surprised her. For a second it made her wonder if he was one of those boys that liked dressing in girls clothes, it would explain why he took to it so easily. But considering how much she had to cajole and **** him to accept the situation they were trapped in she let the notion go. “Well the two of you have fun tonight and don’t do anything I wouldn’t do Genna.” She gave her feminized son a playful wink knowing exactly what was going to happen. She needed Genna to play along so she could get a hold of Brandi’s money. She would make it up to Greg later, but for now Genna needed to do her part.

Heading out the door the two walked over to the car in the driveway. Instead of Marcus’s beat up old car there was a black BMW coupe. Greg stood there staring at the car as Marcus opened the passenger side door for him. “What happened to your car?”

“It’s at home, Dad let me borrow his car for the night. I told him where we were going and might have shown him a photo or two of my pretty date.” Greg’s eyes went wide as he shook his head, causing his hair and earrings to sway.

“No… no… you didn’t.” Marcus leaned in, kissing Genna on the cheek once again.

“Relax, he only saw the same thing I see when I look at you. A beautiful young woman I am lucky to have as my girlfriend. Now climb on in.” He punctuated his statement with giving Genna a light pat on the ass that had Greg feeling like he was about to pop out of his heels as he hopped slightly from surprise.

“Listen Marky… Marcus. Do we really have to do all this? The girlfriend boyfriend thing, how long have we known each other?”

Placing one hand on Genna’s left hip and the other gently touching her cheek Marcus moved much closer so that his face was only a few inches from hers. “Genna, I actually don’t mind it when you call me Marky and as to how long we have known each other. I can honestly say I haven’t known Genna Abella for nearly as long as I would like to. If you want though we can skip dinner and dancing and just head back inside. We could just spend time in the car right out here, or drive around.” Marcus looked his date in the eye as he spoke softly to her, tempted to press his mouth to her shiny red lips and taste her.

“Ahh… dancing sounds nice!” Greg said freely after glancing down at his best friend’s crotch. He wasn’t sure if he saw his friend’s dick move or get hard or anything like that, but his mind told him that it was. He was able to read between the lines of watching a movie or sitting in the car and wanted out of that much more than eating dinner somewhere nice and dancing. Marcus was often pliable, this confident thing was new. Greg thought that if he played the part of the love sick girl, he could push Marcus and control him like he used to. Give him a little of what he wants and then steer him down the path he wanted. He really hoped that worked otherwise he was going to be tasting one of the flavored condoms, this time wrapped around a real dick instead of one of the fakes his mother bought for him. Thinking about them made Greg extremely happy Marcus didn’t use the bathroom in the hallway, otherwise he might have seen one of them stuck to the wall in the shower.

“So ahh, dinner and dancing.” Greg said wanting to be free from the light embrace, but needing to play his part.

“You are so beautiful Genna.” Marcus said, before giving in to his urges and kissing his new girlfriend. Sliding the tip of his tongue into her mouth, brushing it against her tongue as he tightened his grip on her.