Meeting for dinner

As the Uber pulled into his apartment complex Bailey looked down at his clean shaven smooth legs and the multiple bags at his heeled feet. A day of rest turned into purchasing a pair of way too expensive heels, a choker, more panties and a new hairstyle, then there was the counter with Liam. No, he wasn’t going to think of that path anymore. This time tomorrow he would be back in his clothes, a shaved head and have to dip into his savings to get a new phone, but tonight he was finally going to have Mandy to himself. Derrick might want her, but he would be the one fucking his woman.

“Bailey, earth to Bailey.” He snapped out of his mental revelry where Mandy had only removed her dress and was straddling him. “Huh, what?” With a slight shake of her head Candi pointed out the windows. “Come on girl, your stop. See you tonight.” After a hug Bailey got out of the car with his new purchase to grow the ever growing woman’s wardrobe and made his way to the apartment door. As he pulled out the pink key he gave a silent prayer that Aunt Megan wasn’t there. Stepping inside all the lights were still on like he left them. “Hello, Aunt Megan! Mommy you here?” When no reply came he pumped his arms and danced a little in place in joy that he had at least the smallest moment to himself. The time would have to be spent getting dolled up, but it sure beats that witch being here and coming up with some punishment, like using the dildo, or spanking him again for something that wouldn’t have happened anyhow if she didn’t do this to him. Quickly he grabbed the shoes Candi wanted to borrow and hurried back to her, hating the bra-less outfit more and more with each step. When he handed the shoes to her the teen girl smiled happily looking at them, giddy with excitement. “I just love that we have the same shoe size.” Bailey looked back to the shoe in her hand and smiled. “It has been like amazing, but like how about you keep them.” The smile on Candi’s face brightened. “No way! Are you sure?” Bailey eagerly nodded, happy to lower the girl accessories down, even if it was just by one. “You got me so cute heels today, it is the least I can do.” Bailey tapped the roof of the car as if to say goodbye when Candi rejected the offer. “Hmm, I would. I really would, I love these shoes, but my closet is so much bigger than yours. I promise to get them back to you, okay?” Agreeing with the girl so he could get back inside, he considered maybe he could get some money for the clothes online.

When Amanda came home, she dropped her purse off on the kitchen counter before looking into Bailey’s room to see how she was doing. “Hey princess, how was your day?” It seemed like every time she looked in on Bailey lately she saw her once boyfriend, now daughter sitting at the vanity doing something feminine like doing makeup, or writing in that little pink book with a colored pen. Today Bailey was sitting at the vanity already in the little black corset, stockings attached to the garter belt and applying another coat of red nail polish. What really shocked her was Bailey’s hair. “Oh, hi Mommy! Today was like really a lot, but what do you think?” It was getting harder and harder for Amanda to remember who Bailey was, not just from looking at the pretty teen in front of her, but the way he always acted and talked. “You look beautiful princess. Stand up for a moment sweetie and I will tighten the corset for you.” She expected a little fight or even a grimace, but Bailey only stood up and spun around. “Do you need any other help getting ready?” Amanda watched Bailey flip her much longer locks over her shoulder and smile. “No I got it.”

Leaving the room Amanda gave one last look and shook her head before heading to her room. Wondering what happened to the arrogant man, while Bailey looked at the empty doorway as his girlfriend vacated his room. “Hours, we only have hours left.” Bailey went to take a breath and felt a little light headed, forgetting to adjust for the now tighter **** device. Looking back to the mirror he looked at his reflection and blew on his glistening red nails. He didn’t think the nails needed another coat, but considering Megan was there the first day of all this he thought she might show up to be helpful the last and bring back his clothes. That damned woman was going to make him beg for his own clothes back, he was sure of it. Picking up a brush looked at either side of his face ready to do some contouring. “Time to look pretty.” The process of getting ready for a night out was much more involved than Bailey would have liked, but after slipping on his brand new heels he left the bedroom and saw the master bedroom’s door closed. With a stop at the bathroom to take another dose of those pills, he knocked on the door before opening it. “Mommy, you almost ready?” Stopping just a foot in the room, Bailey felt his breath stuck in his chest as he took in the vision of beauty that was Amanda Best. Who ever said a woman was past her prime in her late thirties had never seen this woman. Bailey was seeing her from the back, but Mandy was leaning over her dresser as she looked in the mirror. Her wonderful ass was on display in the little black dress, from behind it was tight, but went below her knees, though he knew it had a slit up her left leg in the front. “Almost ready pumpkin, oh come here I have something for you.” Bailey wasn’t sure what she had, but hoped it was not some last minute girly gift to remember this all by. What she had for Bailey was a few spurts of her perfume, a scent that drove him wild. Every time he smelled the scent it made him want to kiss and nibble on her neck. “There you go, now you smell as pretty as you look.” Looking to his pretend mom he smiled. “I loved that perfume on you, thank you for sharing.” It was odd, Bailey was the tallest he had been in his life in the towering six inch heels, allowing him to be six foot tall, but even in shorter heels his girlfriend was still just taller than him. “Sweetheart, you look so amazing tonight, would you mind if I took some photos?” Glancing at himself in the mirror Bailey didn’t really want proof any of this was happening, but just earlier today he read the horrible diary to a camera, where Candi was going to upload it for him. “Well if you weren’t, I totally was. Mom, we look hot tonight.” The comment made Amanda laugh as she escorted Bailey to his room.

“Maybe sit at your vanity and pretend to be touching up your lipstick.” Amanda took a few more shots of Bailey before it was time to go. The idea of having a few shots of his sexy girlfriend was something he pressed for, but the best he could get was a few photos taken of the two of them, mother and daughter happy and ready for a night out. Bailey held the small clutch purse between his two hands looking down at the ground, watching his shadow move in the remaining light of the Friday sun as they waited for the Conners to show up to the restaurant. It wasn’t the first time Bailey had been to places that had front door valet parking, but it was the first time he had done it wearing a dress. More than once this week he felt like everyone was looking at him, but as a worker opened the door for him he felt uncomfortable. The thought of asking if they could go sit at the bar crossed Bailey’s mind, but he knew the option to imbibe anything alcoholic was not an option. The last sip of **** ended up getting his ass slapped by Mandy and while that wouldn’t happen again, he knew a drink tonight was off the table. So he stayed silent just watching the diminishing shadow as the two of them waited for the rest of the party to show up.

Sitting in their car Derrick looked to his daughter. “Are you ready to head inside?” Candi who was touching up her mascara in the small mirror on the back of the sun visor stopped what she was doing and gave her father a quizzical glance. “It takes time to look proper, Miss Best will understand. I might be able to hurry if I knew my Daddy was in love. Are you in love Daddy?” Derrick wanted to give his daughter a flat look. “Candace, that isn’t appropriate.” He then looked away from the girl, unable to hold in his smile. He wasn't some kid with puppy love and knew it was something that had to grow and be fed. But the connection with Mandy was real, he was going to give this his best shot. When they got out of the vehicle Derrick saw his daughter bursting with energy and her trying to contain herself and stop from skipping forward. “Here let me see.” He said for Candi so that she turned and looked at him, bouncing on the balls of her feet a little. Derrick leaned a little to the left and then the right as if he was inspecting her. “Hmm well you do look pretty, so the time was well spent. No promises on not trying to rush you out the door in the future though. We were never on time for anything with your mother, so why not continue the trend.” He saw his daughter give him a full toothed smile. “Time well spent, not a second wasted. Now come on, you are making us late.” Rolling his eyes he followed.

To the side of the front door a few steps back from the valet attendants Derrick saw the best girls waiting. He saw Mandy spot him right away, and even from this distance he was happy to see a small smile come to her face, while Bailey was at her side spacing out. He wondered if she had ever been tested for ADHD, and wondered if it frustrated her to have trouble focusing. When they got closer Candi couldn’t contain herself anymore and rushed forward as quickly as she could in her heels and was happy the ground was even considering his daughters lack of coordination at time and how tall her shoes were. When his eyes moved from Candace they look to Mandy and went right to her blue eyes and couldn’t help himself from increasing his pace just a little While Bailey stayed still for Candace to go to her, he saw Mandy take a few steps to meet him part way. Just a few hours ago the two of them were holding one another in bed and it felt like it was too long. Derrick gave her a quick hug, taking just an extra second to enjoy the feeling of her body pressed into his before giving her a kiss. Stepping back he looked the gorgeous woman up and down at her choice of outfit. “Mandy, you are ravishing tonight. I wish I could see you everyday.” He could make out the blush on her cheeks, he loved seeing her react to his compliments like she wasn’t used to getting them. “Thank you, but did you mean, you wish you could see me like this every day? Because that would take a lot of time, are you prepared to make sure I get paid even though I will be late to work?”

“No, Mandy. I meant what I said. I wish I could see you everyday.” The blush hadn’t vanished from before and she held her hands to her cheeks as it increased. “Though I think I could authorize that if you are willing. As Candace told me, it is time spent, not wasted.” Amanda looked away from Derrick over to the girls behind her, wanting to look anywhere, but at this man until she could get herself under control. “She does look wonderful tonight.” Amanda said feeling Derrick step up behind her and wrap an arm around her waist and take her hand in his. “All three of the princesses I get to accompany look beautiful this evening. All three match one another, the real challenge I have is picking who I shall dance with first this evening. The stubble scratched her cheek a little as he gave it a quick kiss before whispering. “Shall we go inside?” Her initial reply was to maneuver so that she was still holding his hand and could move in to give him a kiss with just the hint of tongue. “Who to dance with first, Princess Candace, Princess Bailey, or Princess Amanda. If your goal was to impress me, it might be cute to see you with either of our daughters, but you run the risk of me feeling jealous for not being chosen first. Choose wisely.” She heard Derrick chuckle a little at her playfulness. “I did say it was a challenge, but I think I have an idea. I also can't help but notice our girls have the same hair style now. Candace is awfully fond of you, better make sure you take home the right girl tonight. I wouldn't put it past them to swap outfits like this is the old parent trap movie.” The comment made Amanda laugh, she knew for a fact Bailey was not going to go for that.

The four walked inside and felt the cold air wash over them, it was cranked up high to fight the Nevada summer heat. Inside just ahead was a check in station that the girls rushed up to. “Reservation for Connors Best family!” Candi said happily. Off to their right was a large bar, to the left were several small tables. This area was for people coming in to enjoy the live music and have small plates. The group was led forward down a few steps that had a polished brass hand rail in the center to a level of booths. If you kept going down one more level there were more tables in front of an open dancing area and a stage that had a string quartet accompanied by a piano.

The place was like taking a step back in time and each of them took a moment to appreciate the hidden gem. The smooth music filtered through the room in a way that made it easy to listen to and quite enough to hold a conversation. Bailey looked around and wondered how much money Derrick was going to spend tonight, and felt lucky he no longer had to compete for Mandy with him after this was over.

I attempted to edit the photos of the dresses, adding the belts, and the choker for Bailey. Sorry it isn't great quality, did my best I swear :)