Dresses and More Dresses

Looking out the windows Bailey watched the traffic of the highway speed around. He couldn’t believe that he was going to the mall again, he had been in that place of worship to the god of shopping more recently than in the last year. He had long since gotten used to being out in public dressed this way, not that he had a real say in any of it, but at least this time traveling in Aunt Megan’s car he got to ride up front. He glanced over to the smiling woman driving the SUV and thought about how gracious she pretended to be before they left.

“Now that we have all the photos of your hair and makeup, the next step is to get some in the right dresses.” Bailey looked at her perplexed, but didn’t say a word about her plans for a dress up game. “Homecoming, Junior Prom. They are big events in a girl's life and just because you were a tomboy doesn’t mean Auntie couldn’t have gotten you a makeover and a pretty outfit.” Megan raised an eyebrow at Bailey still seeing her perplexed. “Bailey honey, we can’t change makeup and hairstyles without spending money at the mall, so we did that here and then I will take photos of you in some pretty dresses and put it all together for the photos and make you look a little younger.” Bailey’s eyebrows went up as it all hit him, with how she was going to photoshop it all together to remake more of his past. “Now I didn’t want to spoil anything for you before, but I made an appointment yesterday for you at the salon as a reward for you if you were good! I’m so happy we didn’t have to cancel, but if you do a few more exercises without complaining I will let you choose what you get done today, isn’t that exciting?” The last time he was at that place his hair got longer and some of it became platinum blonde and while he never looked at all the services they had he didn’t want to know what she would have in store for him. Maybe he could just get his nails redone, or a pedicure, that felt wonderful last time. “Wow, that sounds like amazing! Just tell me what I need to do, Auntie.” He said with excitement in his voice that he sure didn’t feel. “Before we go you are going to get done another page in your math book and I would like you to repeat both of your mottos five times in front of the mirror, but do so with a smile, but I don’t want you to just say them. No, I want to hear you sing them, cause you love them.”

He did as she asked and even danced a little in the mirror as he sang the mottos, last thing he wanted was her to say do it again because she just didn’t think it felt real enough. Now as they pulled into the mall he was happy he did. Aunt Megan loved it, gave him a hug and told him his choices. Turns out he was getting his teeth whitened and the options were having his lips done with filler or something like that or eyelash extensions. He figured the eyelash thing would be like having mascara on all the time and the other would be giving him DSL and that was not something he wanted. So white teeth and longer lashes was the super easy choice. As the car parked Bailey pulled down the little mirror in the visor to check his makeup, a good girl always looks her best. Nothing was out of place and as he looked at his lips he congratulated himself on his foresight for adding the dancing, it was a massive victory not to have that done. “Oh you look fine pumpkin, lets go try on some dresses!” Bailey clapped his hands rapidly to make excited little claps as he smiled large enough to show teeth. “Yay!” Bailey’s face shifted to a serious one as he looked at his Aunt. “But like I can’t be the only one trying on dresses, this is a group activity.” If he was going to have to be dragged through this, then at least he wanted to see the woman in a nice dress. One of the only saving graces to trying on some of the cute outfits with Candi was seeing the girl try them on too. “I think I’m a little old for homecoming or prom, but…” Megan stopped to think and smiled. “Sure that does sound like fun!”

Walking to their first destination, Megan stopped Bailey as she “accidentally” dropped her purse. “Bailey sweetie, could you pick that up for me.” Bailey didn’t even think twice about the request as he stepped closer, putting his heeled feet together and bending over at the waist to pick up the dropped item. A good girl is obedient. “Careful I would like totally die if I lost my purse.” He lied to her. The more he stayed in character the more willing she seemed to be to play nice and he really needed her in a good mood to request she stop fudging going through his phone. Bailey hadn’t even noticed how the dropped purse happened to be around a crowded area with plenty of boys to look at his khaki skirt covered ass as he stuck it in the air. “Oh stop, you would not die, stop being so dramatic.” Megan waved her hand in the air at Bailey as she took her purse back, feeling more than pleased at her niece's progress. She would need plenty of reinforcement, but she was coming along nicely.

Bailey was on his third dress before Megan looked happy. He watched as her face lit up as she waved her hand up and down at Bailey as she stood there in a long forest green sleeveless dress with lace bodice. It was long enough that it touched the floor even in the borrowed three inch heels. “That one suits you so well pumpkin! Let me take a few photos with you posing, oh gosh that is so nice on you.” Bailey moved this way and that acting happy as can be to be her little model. “Thank you Auntie, but I think it is your turn and I saw just the thing!” Bailey hadn’t taken the dress off yet when he grabbed Megan by the wrist and pulled her over to a dress that wasn’t overly sexy, he didn’t want to try that first. The dress was an A-line scoop neck almost knee length with a black lace top and a skirt that puffed out that was an almost gold color. “Oh Bailey, I think I might be a little… mature for that.” Bailey let go of her wrist and pulled the dress off the rack. “Not at all! I could see you wearing this to a wedding or like if your work had a gala. Just think of Charles putting his arms around your waist in this.” Bailey said to Megan holding the dress out. He thought she would look great in it, but like Mommy she would look good in anything… like Mandy, she would look good in just about anything. “Alright, I will try it on while you try on that pink one you picked out.” The pink one you picked out not me he mentally corrected her. “That one is so pretty I just couldn’t help myself.” Bailey giggled as he went along with her fabrication of events. Bailey almost skipped to the dressing room to show just how excited he was, but had to tone it down due to his current heels being a little big on him.

Outside the dressing room Bailey held the pink tulle skirt in his fingers as he felt it swish every time he moved his hips from left to right. He was looking at himself in the pink sleeveless dress, the bodice was lace that was full of silver sparkly bits that faded into the tulle skirt that came down to mid thigh. It was a pretty dress and he thought back to his high school prom, when he was at his date's house watching her come down the stairs in her thin high heels and pink dress that looked much like the one he wore now. Though he thought hers was longer than the current one he wore. Thinking back to how she looked he was sure the dark haired girl, Mary… Mary Stewarts must have spent all day at the salon to get her straight mousy brown hair to be at least three shades darker and become a bass of curls. She was so beautiful and he couldn’t wait to hold her close, dance with her and then have her legs up on his shoulders as he had her way with her later that night. Looking at himself now he felt guilty for breaking up with her two days later. He had been so looking forward to that night, but she didn’t even want to go back to the hotel. Bailey remembered being upset at spending the money and how this was a right of passage and she didn’t even want to give him what she owed. What she owed… that was a hard thought for him to swallow now that he had put another man’s dick in his mouth on a date. She was so pretty though, and looking in the mirror at himself and the blue eyed, blonde woman approaching him from behind he knew she agreed with what he saw in the mirror. Aunt Megan knew he looked beautiful in the pink gown. “Bailey, you look wonderful! Do a little twirl for me!” Bailey did as she said pivoting on the ball of his foot as he did a little spin in the black heels that did not go with the outfit. “Thank you! I feel like a princess! Do you really think I look good?” Bailey did another little twirl for her giggling he did. When he stopped he took in the woman in front of him in the dress he had picked out, it looked fantastic on her.

“Aunt Megan, that like looks wonderful on you. You are like so pretty!” Megan gave Bailey a hug, he wasn’t even sure if she thought about it before she did with how rapidly it happened. “Thank you.” The woman’s voice was quite like she was holding something in and when she pulled back he watched her wipe a tear that threatened its release. Megan looked at herself in the mirror, the dress would have to be adjusted or she would have had to find one a size bigger from her bust, but Bailey was right. The dress looked great on her and she could imagine dancing at a party in it on. She was under no illusion that she wasn’t pretty, the attention of Charles the two dates they, well sorta dates were proof of that, but she hadn’t been dressed up in a long time and it was really nice to feel pretty. Pulling herself away from the mirror she looked back to her niece. “Now let's get some shots of you in that before we try on the next outfit.” After taking the photos and shooing Bailey off, Megan took another look at herself in the three way mirror and snapped a few shots of herself. Thinking about maybe putting the outfit on layaway, for her work Christmas party, it was a way off so she wouldn’t have to pay for it all at once.

Bailey got to see Megan in one more dress he picked out, this one had a deep v-neck and a skirt that went to just below her knees and he loved seeing her in it. He was less thrilled with the blue long sleeve blue flared skirt dress he tried on or the red prom dress that had one of those skirts that was short up front, but would drag on the floor if he hadn’t been wearing heels. In each he posed and smiled. The overall experience at the dress store wasn’t nearly as bad has he had expected. Aunt Megan was in a good mood, not once giving him a pop quiz or making him say how he likes to tease and please men while in the dresses. The best part was seeing her in that last dress, wow was she hot. What did surprise him was when she took that first dress he had her try on and brought it up to the register and put it on layaway. The store clerk was much more pleasant to them now then when they told her they were browsing now for Bailey’s senior year. Walking out of the store Bailey figured the best time would be now for his request. “Aunt Megan, could umm.” Bailey fumbled with his words, he had to get this right. “Yes pumpkin?” Megan looked at Bailey who was looking down at the ground and fidgeting with her clasped hands in front of her. “Do you, ahh.. Do you think maybe, you could please let me do all my texting. Please?” Megan pressed her index finger to her lips that had a small smile on it. Bailey was being so demure, not demanding. “If you think you are ready to be your true self with everyone I don’t see why not, but I will be watching and will help guide you from time to time. How about that?” Bailey looked up to meet her blue eyes and gave her a big smile. “That sounds like amazing! Thank you!” Yes! Another victory, Bailey thought mentally celebrating. Megan watched as Bailey closed her eyes and danced a little in place and stifled a laugh at how cute Bailey was. “We have a little time before your appointment, how about we get a nice salad for lunch.”

A salad was not his idea of a lunch, but he was starving and biting into a crisp cucumber sounded delicious right now. “That sounds soooo good!” His mouth already watering, Bailey followed along happily through the mall.