Mother Daughter time before bed

Bailey heard the apartment door close as his girlfriend came inside and ignored it and just kept looking down at the little pink book he was currently writing inside with a purple inked pen. Inside he was writing about the events of the day of the perspective of the teen girl he kept seeing in the mirror. He saw Mandy come to his open door, but didn’t look up from what he was doing. Bailey didn’t know if he was more angry or sad that she would cheat on him like that. She was making out with another man right where he could see her. “Baby, it is time to get ready for bed.” Amanda said sweetly as she watched the dolled up girl writing in a little book. When Bailey gave no answer she stepped into the room and repeated herself. “Baby, time to get ready for bed.” Now inside the room she was able to get a better look at what Bailey was doing. “What are you writing in that book?”

With her being so close to him Bailey quickly flipped his diary closed, afraid she would read over his shoulder and could no longer ignore her. Standing up Bailey looked her in the eye, he wasn’t sure if Mandy was able to read the emotions that were brewing within. “I’m not a baby!” he snapped at her before adding “And the book doesn’t matter.” then stepped closer to bed and opened his night stand drawer to toss the book inside. As fast as he could, Bailey closed the drawer to hide the contents he saw within. He wasn’t sure when she had done it, but inside the nightstand was the dildo Megan had made him use and a small bottle of lube. For Amanda it was easy to forget who this girl was in front of her, she was very much reacting like a teen girl not wanting to be called a baby or child. To her Bailey looked like she was hurt and then tried to hide her diary. The expression changed when Bailey looked back at her after hiding her book, it was a look of worry.

Amanda moved over to Bailey and pulled the smaller person into her arms. With Bailey removing the heels and Amanda still wearing her own, she towered over Bailey. “I know you are not a baby, you are a young woman. I am sorry if I hurt your feelings after all you did for me today.” Bailey wasn’t sure why Mandy would say that. Was she fucking with him? Did she no longer see him as a man anymore? He was ready to push her away, when he remembered just a few nights ago when he asked her to spank him and help to keep him acting in character. Bailey could swear he felt the phantom pain of Megan’s slap to his face and Mandy’s slaps to the ass all at once. Pulling back from the hug Amanda pressed the knuckle of her index finger under Bailey’s chin so he would look up at her. She expected him to balk about remark, but instead she only a partial shy smile. “Good, I’m glad you can see that.” Bailey replied the woman before him, doing his best to not let the desire to cry as he played the part of the daughter.

“Thank you, for like umm being a good Mom.” Bailey said stepping away from Mandy looking to the ground to avoid eye contact. “Could you umm, help me?” he said as he turned his back to Mandy and moved his hair out of the way of the button at the top of the dress and zipper. Amanda was more than happy to help, compliments like that made her feel so happy and it made her wonder how much Bailey was enjoying the chance to live as a teen girl. She thought it might have something to do with not having to worry about things, as a teen she didn’t need to consider the bills or how tight money was. Didn’t have to have the stress of searching for a job or the constant disappointment of rejection. Being a girl probably wasn’t ideal, but without those worries she saw someone flourishing. While all those thoughts and more went through Amanda’s mind, she helped Bailey out of her dress and corset.

Soon Amanda could see Bailey removing her makeup, as she stood behind Bailey, humming and brushing her hair. When she was done Amanda knelt down and hugged Bailey from behind as she pressed their cheeks together as she looked into the mirror. “You said you wanted to match my outfit for tomorrow night right? How about you help me pick out what I wear tomorrow, does that sound like fun?” Sitting there in a green babydoll nightie Bailey a smile, the type that touches your eyes with excitement or joy. “I get to pick out what you will wear for dinner tomorrow night?” It took a lot of control for Bailey to not try and kiss Mandy or push her down on the bed as she helped him get undressed. She still looked incredible, and a large part of him wanted to show her, remind her who he was and how he could make her feel. That couldn’t happen though, but her letting him pick out her outfit wasn’t something she was inclined to do. His mind ran through some of the really sexy outfits she had in the closet, that he would love to unwrap her from after dinner, like a present to himself for going through the week. Another option was to pick something conservative so Derrick didn’t get to look at her, after all she would be naked with him after the dinner either way. “Of course you can help pick, you are already borrowing my clothes. Why would I not want your opinion on what looks good, you have always had a good fashion sense.”

After finishing up Bailey found himself sitting at the edge of bed he once slept in, feet dangling off the side and crossed at the ankles as Mandy pulled dress after dress out. He expected he could just look through it and choose what she would wear, but she was pulling out the dresses and holding them to her and asking what Bailey thought. Mandy didn’t just want a yes or no, she wanted to discuss the outfits and what could go with them. This went from something quick, to something long and drawn out. Not just that, but he wasn’t enjoying his girlfriend treating him like he was some girl fashionista. Some of the outfits Bailey would get lost in thought in as he imagined Mandy in them and what he would do to her, with her in it. The thoughts could never go on long, with Mandy practically demanding his attention. “Okay, now focus honey. I have narrowed it down to these two dresses. What do you think?” Bailey looked at the two options, neither of them were what he wanted her to wear for Derrick, but very much for him. One was a dark green shoulderless dress, the skirt was long enough that Amanda would have **** but to wear tall heels to not drag it on the floor. The thing had a long slit up one leg that she would have to be careful with or give someone a look at her panties. The other was a black dress that had one shoulder, a deep neckline that would show off plenty of cleavage and a skirt that would stop at the top of her calves, and a slit by one leg that went up to mid thigh. “Just those two, what about that lacy black dress with the sheer sleeves?” Bailey tried to counter.

Amanda frowned at Bailey. “The one I wore to your Dad’s funeral? No that is not even close to being right for tomorrow night, we…” Bailey was a little worried she caught on to him wanting her to look much more conservative and why for a second before the little frown turned into a smile. “Okay you had your fun, now stop teasing and help me pick.” The black dress wouldn’t be considered conservative by anyone who saw Mandy in it, but it was less revealing than the other. With a sigh Bailey pointed a red nailed finger to the black dress. “Little black dress is a classic for a reason, maybe add some color with accessories.” Bailey fell backwards onto the bed, thinking it was a false hope anyways to get his pick of what she wore. At least he was able to keep her from wearing that green one. He remembered her getting it for a Christmas party for the office that never happened and how upset she was after spending the money. She even asked him if it was okay if she didn’t return it even though they could use the money and it no longer had a purpose. He had told her to keep it and to think of it as an early Christmas gift from the both of them to her. He would find something else for her to wear that gown to, but out with Derrick was not going to be one of them.

Laying on his back Bailey reached up and cupped one of the breasts that were weighing down his chest. Laying like this reminded him how sore they felt right now. “What do you think of this?” Putting his elbows on the bed and sitting up a little Bailey looked over at Mandy, who was holding up a pair of glossy red open toed pumps and some hoop earrings that were red on the outer rim and gold at inside. Laying back down he rested his right arm over his eyes. It was getting late, he felt drained after the horrible day and didn’t want to give fashion advice. “That looks really good, I love the red, but maybe just a gold necklace too.” he said while trying to fight off a yawn. A moment later he felt the bed move as Mandy climbed onto it next to him.

Amanda got onto the bed and pulled some of the pillows down to them and propped Bailey up. “Okay, we got my outfit, time to find something for you that can be delivered the next day. Ready to do some virtual shopping?” Bailey wasn’t sure where her energy was coming from, but Mandy was down right up beat. “What girl doesn’t like shopping.” Bailey said shifting so he could look at the screen of Mandy’s phone. Forty minutes later Bailey was groaning internally at the excitement his girlfriend had for just purchasing him a new dress. The selected black dress was too short, too tight and the neckline plunged way too much. Something he would rather see someone other than him in and then because Mandy wanted them to match she orders a thin leather red belt that had some little flowers for a buckle. “I liked that other dress, to bad it was out of our price range.” Amanda said giving the sleepy Bailey a hug. “This was fun, now I think it is past both of our bed times. Tomorrow should be a light day for you honey. Some laundry and clean your room, I noticed you did not make your bed today. I expect that to be corrected tomorrow and get your clothes in the wash. Other than that you are free to spend Friday however you want, so long as you are ready to go for dinner on time.” Returning the hug weakly, Bailey slid off the bed and partially mumbled. “Good night Mom.” Amanda smiled at the half a sleep Bailey and called back to the feminized man. “Mom?” She inquired, getting more and more surprised how well Bailey was taking the role. Turning around with half closed eyes Bailey gave a half smile and a partial wave. “Sorry. Good night Mommy.” he corrected before heading back to his room to curl up under the blankets.

Walking back through the apartment, turning off the lights as she goes Amanda stopped at Bailey’s closed bedroom door. Opening it up a crack she could see Bailey already fast asleep under the covers. “Love you too Bailey.” She whispered for closing the door as silently as she could to not disturb her slumbering daughter.