Bedtime

Taking one of the bottles of the berry smoothie from the fridge Bailey took a sip and made a face. It was better than the other green smoothie, but the kale sure didn’t help the flavor. A few more sips before he let out a sigh and headed to his new bedroom, the clicking of his heeled sandals with every step. Sitting down at his very own vanity Bailey started to wipe the makeup off his face, watching as he saw more and more of his old self appear and yet with the outfit, pigtails, large hoop earrings and of course breast he wasn’t sure anyone would think of him as he used to be if they saw him. With that done he started to undress getting down to just the white panties when he heard Mandy calling from the other room. “You almost ready sweetheart?” before opening the door and seeing Bailey standing there in white panties smooth in front from the tucking kit, breasts hanging free and still wearing the hoop earrings. She saw no trace of her boyfriend in front of her, making what happened earlier a little easier on her mind.

“You going to sleep like that princess?” Bailey looked to Mandy and then back down to his exposed breast, fake or not it was embarrassing. Covering them with one hand he went to the dresser and pulled the first thing he saw, the same babydoll nightie from last night, and pulled it on over his head.

Amanda saw the cute blonde standing before her red faced looking at the ground in her pink babydoll with a little boy in front, her hair in pigtails and the large earrings. “Come sit so I can brush out your hair sweetie.” she said sitting down on the bed and patting a spot beside her. When he sat down, she took the pigtails out and started to brush it with the real hair brush and removed his earrings. “These are pretty sweetie, but you can’t sleep in them.” another blush came to Bailey’s face, this entire thing was uncomfortable. The woman he loved was brushing his hair like he was her child... exactly what he was pretending to be and how he over looked the weight of the earrings. The feeling of the hair actually being brushed felt heavenly, much like how the massage was with Hector earlier. It was odd to know something was wrong in his head, but for it to feel so good on his body. After maybe forty or fifty strokes through his blonde hair Mandy smile and wrapped her arms around him from behind. “There all done princess. “Now time for bed young lady, you had a busy day.”

Amanda tucked Bailey into bed, pulling the sheet and blanket up and put the teddy bear under his arm. “Good night, I love you baby.” she said kissing him on the forehead before turning off the light to the room and closing the door.

Laying there in the girly room Bailey puffed up his cheeks and blew out hard, causing his bosomed chest to shift. It was to have the affirmation that she still loved him, but the kiss on the forehead was not the type of kiss he wanted from his beautiful girlfriend. Nor did he like the throbbing on his backside from her spanking. He wasn’t sure why Amanda liked being spanked in the bedroom, it just plain hurt. Bailey just laid there looking up to the ceiling reflecting on what went down today before deciding he rather distract himself then go through that mess again in his own mind. Pulling his arm free of the stuffed bear he pushed the covers down and leaned over to grab is laptop from the nightstand.

Opening a web browser, he went to click on one of his favorites, but stopped just before clicking on the link remembering what happened last time and the repercussions he was still feeling on his rear. Thinking she may have that on lock down, but he still had his hidden folder of pictures. Clicking on the folder icon he clicked on one of the most accessed folders titled ‘Fonts’ to get to his porn stash. Inside though instead of busty babes, lesbians going at it was pictures of large men with their cocks hanging free and hard. One of them showed a muscle head man having a girl bent over pulling back on a leash attached to a collar she was wearing as he took her from behind. “Ugg.. Guess she found this too, fuck.” he whispered closing the folder. With some contemplation he opened the folder Megan left for him, they might be the point of view of the girl looking at the guy as she goes at him, but he could still see their breast. It would be enough for him to get off he thought. Turning the video on Bailey reached into his panties and stopped, realizing with Mandy coming in the room before he never untucked, the kit was still holding him in place. The video played as he tried to peel the pad back without getting out of bed, but before he could the bedroom door opened. To Bailey he could see the outline of Mandy from the light from the other room.

Amanda was moving between the living room and kitchen cleaning up from the day still dressed as she had from work minus the heels and blazer. When she was considering what to eat, she saw a light from under the Bailey’s door. Walking over she threw open the door and saw the blond teenage girl with a laptop to her side showing the point of view of a woman giving a muscular man a blow job, while Bailey had one hand reaching into her panties. “Bailey Ann Best, I don’t think so young lady.” Amanda walked up and slapped the laptop shut and pulled it from the bed. She saw the wide-eyed stare of her temporary daughter. “You were told to go to bed, you are just asking to be grounded or another spanking. Now do as you are told and go to sleep.” the feminine name cut through Bailey the way she said it with an elevated voice, he was to shocked to respond before she was gone with his laptop leaving him in the dark with one hand down his panties touching the edge of the kit that he was unable to pull off with any quickness from the long nails. Pulling his hand out he slapped the side of the bed in frustration, she was doing what he literally asked her to do.. Keep in line like her child, but never figured she would stop him from jerking off. He sure as hell wasn’t going to sleep in the kit so he started to get out of bed to get it off when he heard Mandy yell from the other side of the bed. “If I open this door and you aren’t in bed with your eyes closed you are getting another spanking miss!” glaring at the door he wanted to tell her this was all over, but stopped letting his mind rule instead his emotions and climbed back into bed and pulled the covers up angerly. He wanted to defy her and just stay awake, his mind imagined how he would show Mandy who was boss when he was not having to pretend to be some prissy girl in heels and makeup. Despite his best effort sleep soon won the battle and his body drifted off into slumber.