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Chapter 21
What's next?
Mother daughter time
Bailey sat at his new vanity just having finish writing out today events in his new diary. He had tried to make it sound as much like a little teen girl as possible. He dreaded the idea of anyone reading it and was already ashamed of the idea of even Megan reading its contents. He tried to make the writing as over the top ditzy and girly as possible. Even going so far as to dot his i's with hearts and misspell a few words. As he closed the diary, he took another look around his prison for the week. April had done on heck of a job. The room screamed girl and he absolutely hated it.
After taking care of her work emails Megan remembered the package, she had order should be in the mail box by now. She grabbed her purse and went to check. Reaching the wall of apartment mail boxes, she reached into her purse and pulled out Bailey’s missing keys. Then using them she unlocked the mailbox and removed a small package leaving Amanda’s mail inside. No one needed to know she had the keys. Taking the package in hand she headed back inside.
Just then Bailey heard the front door open. Thinking it was Mandy he rushed out of the room only to find Megan walking in from outside carrying a package.
“Here you go girlie these are the kits I told you I ordered to help you tuck. Why don’t you be a good girl and go try one on I ordered their largest pack so you should have more than enough to keep that little growth of your in check this week.” Megan said with a grin as she tossed Bailey the box.
Reluctantly Bailey did as he was told heading to the bathroom to While he hated having to tuck himself the kit was a much better solution and though still uncomfortable it didn’t feel as bad as his former taping method. He was shocked however with just how good a job it did at hiding him away. Once his panties were back in place, he couldn’t find any signs of his dick. In a moment of horrible realization as stared into the bathroom mirror, he saw nothing but a sexy blonde teen in little red thong. Shuddering he quickly finished redressing before rejoining Megan in the living room just in time to see Amanda walk in the door carrying a pizza.

Amanda was shocked at the sight of Bailey standing before her. She had been expecting to see her boyfriend dressed as a girl. She was not prepared for just how hard it was to see anything of her boyfriend in the blonde teen before her. She was the image of a sweet teen girl and for a minute Amanda let herself believe that she really was her little girl, the daughter she always wanted. She made a decision in that moment. She couldn’t have a real daughter due to her choices in life but for just then one week she would let herself pretend. If Bailey was this committed to the character, then she would fully commit as well and try to be the best mother she could be.
On seeing her Bailey decided to seize on this moment before Megan could get control again. Mandy would surely protect him from any more of Megan’s **** at least he hoped so. Running over to her as fast as his heeled feet would carry him, he hugged her tight.
“Mommy I’m so glad your home. I missed you today. Auntie Megan was so nice to take me and Candi shopping and stuff, but I like wish you could have been there. Oh, and thank you so much for my like totally awesome birthday present. Miss April and her friends did like a super fab job on my room. It’s like mega cute. Come on let me show you.” Bailey said with as much enthusiasm as he could muster.
Before Bailey could get any further Megan spoke up as she gathered her purse. “Well, I think I’ll let you two catch up. As much as I enjoyed my day with my sweet niece and her friend, I do need to get home and I still have a few errands of my own to run. Bailey dear it was a pleasure spending the day with you. I know you can’t wait to show your mother all the cute outfits you insisted on having. You have quite the little fashionista on your hands Amanda. She just got so into picking out her clothes. I think we went a little overboard but like I told Bailey as long as she doesn’t take off the tags it can be returned after this is over. Plus, the full closet is more convincing to anyone who might stop in for a visit.” Megan said to Amanda while giving a Bailey a look that told him he had better play along if he knew what was good for him.
“Ok then I do not want to keep you any longer. I just want you to know how much I appreciate your help today. It really makes me happy to see you two getting along so well. When this is all over, I owe you big time.” said Amanda as she let go of Bailey and set down the pizza before walking Megan to the door.
“Oh, I almost forgot Bailey made plans to spend the day with Candi at her hotel tomorrow so you’ll have to drop her off on your way to work. You girls have a nice evening.” Megan said with a wink to Bailey before leaving.
Amanda then picked up the pizza and may her way over to the table motioning her daughter to join her. “I know your excited to show me your new room and clothes baby but why not sit down and eat first. Megan texted me to let me know about your decision to diet and try and get back in shape. I think that’s a great idea so I got us a small veggie pizza to share for dinner. Now come sit down and you can tell me all about your day.” Amanda said with a warm smile.
Bailey grimaced inside at yet another healthy diet meal but settled in at the table and ate what he was offered with a smile. He then went through explaining how his day had been, keeping to the girlish character he was trapped as. However, choosing to leave out some of the more embarrassing incidents such as the dressing room accident and his new belly piercing.
Amanda just sat and let Bailey spin her tale of the day’s events interjecting from time to time with various questions, and complimenting her on the newly pierced ears. Finally, once the story was complete, she let Bailey show her the newly redesigned bedroom.
Amanda was surprised to say the least as she followed her into the guest room. April had really out done herself.
“So, Miss April like got some people from your work to totally makeover my room mommy. Isn’t it just like super cute?” Bailey said trying to stay in character and not get himself in more trouble. Then handed the note that was left on the dresser for her to read.
He wasn’t worried about Mandy herself if he broke character but he was terrified that she would mention it to Megan and he couldn’t risk what she might do.
“Well, I will have to remember to thank the team. They did a marvelous job. The room really suits you now sweetie and I love the flower design on the walls it is just so you.” Amanda said enjoying the role of mother to a sweet little girl. She loved Bailey her boyfriend but they would have plenty of time together after all this. Her sweet daughter Bailey Ann was only here for a week and she was going to enjoy it while she could.
“Oh, mommy I almost forgot. Here I got this for you.” Bailey said as she gave Mandy the best mom ever mug. “We played a fun game today with Candi and each bought stuff that like meant something to us and you like mean so much to me I just had to get it.“ beamed Bailey really meaning what he said he didn’t think of her as his mother of course but he did love her and wanted her to know it.
Amanda looked at the mug and then back to Bailey. A tear coming to her eye. “Oh sweetheart I love it! I am so lucky to have you in my life.” She said as she wrapped Bailey in another hug.
“Now I want to see all these new clothes you just had to have. It is ok that you got carried away any girl would with their aunt there spoiling her. Just remember not to take off the tags unless you have too.” Said Amanda in a light admonishing tone.
Bailey quickly set about showing off his new clothes making sure to do as Megan had said and making it sound like he had picked them himself though occasionally mentioning that Candi had pick this or that.
An hour later Bailey was finally showing off the dress he and Candi got for their date. “So, Candi like wanted us to like match for our date because we could like totally be sisters. The boys even like said so.” Before he could keep going though, he let out a long yawn.
Amanda having been thinking about just how much Bailey really seem to know about women’s clothes was pulled out of her thoughts by the yawn. Seeing how tired Bailey looked and remembering that they both had to be up early decided it was time to bring the evening to an end.
“Sweetie I know you are having fun showing me all your little outfits but I think it is time we get to bed. Go put that away and go get changed for bed and I will help you with your hair.” Amanda said.
Bailey at once glad to finally be done with this stupid fashion reveal and be able to change almost agreed before he remembered what kinds of pajamas Megan had made him get. He just couldn’t let Mandy see him in them.
“Oh, mommy that’s like really sweet of you but I’m like totally not tried and I can do my own hair. I thought I might like watch TV or something first.” whined Bailey trying to avoid changing.
“Nonsense you look exhausted and we both have to be up early to drop you off at Candi’s. Now I am going to go change myself and when I get back, I expect to find you dressed and ready for bed young lady.” Amanda said leaving no room for argument as she headed to her room to change.
Bailey just wanted to die of shame but saw no other choice at this point after trying to find something he could stomach he settled on a pink lace baby doll with matching panties. It was still revealing but it was the most modest option he seemed to have. He quickly changed removing his outfit and removing the tuck kit before gently tucking himself into the little thong panties. Looking in the mirror Bailey was torn. On the one hand he absolutely hated this but on the other hand he couldn’t resist staring at the vision of sexiness in front of him. Pink lace just barely covers his fake breasts and the silk bow in front scream girlie while also making him look like a present just waiting for some guy to unwrap. Suddenly realizing he was getting turned on looking at himself he turned from the mirror, just as Amanda came back into the room carrying a familiar teddy bear.

Amanda froze right inside the door way momentarily jolted out of the illusion she had been enjoying all evening. She couldn’t believe what Bailey had chosen to wear to bed. He had always loved when she wore sexy little nighties and now, he stood there in one of his own. He was trying so hard to fill the role he had created even going so far as to sleep in something sexy and girlie just like the girl he had created would. It was simply amazing how dedicated he was to this.
“I saw this and thought you should keep it in here sweetie it was in the picture Derrick first saw of you and it really matches your new room.” Amanda said placing the teddy bear on the left side of the bed. “Now have a seat baby and I will get your hair out of that braid so we can get some sleep.”
Bailey did as he was told blushing and squirming as Amanda stood behind him and gently un-did the braid and then brushing out his hair. While she brushed, she started humming a somewhat familiar lullaby he thought he remembered his own mother humming when he was a child. Stunned and embarrassed at his girlfriend seeing him like this and treating him like some little girl. He had to suddenly fight back tears when Amanda finished and wrapped him in a warm embrace.
“I love you, Bailey.” Amanda said before wiping a tear from Bailey’s face.
“I love you to Mommy" Bailey replied wanting this all to be over so he could show her just how much he loved her as himself not some teenage girl.
“Ok now I think we both need to get to bed morning will be here soon enough.” She said motioning him to the bed. She gently tucked him into bed before turning off the light and making her way to her own bed.
Bailey just lay there fuming after Mandy left. He was a man damn it but she treated him like a baby. Frustrated and fighting tiredness he quietly got up and got his laptop. He needed to feel like a man. He opened up his browser and typed in his favorite porn site. Suddenly a red stop sign covered the screen. Attempt to access Restricted site warning issued. Then the browser was back on the home screen. Bailey cursed but didn’t let the blasted program stop him. Trying instead to just search for one of his favorite types of porn. He typed in busty blondes and hit enter. As soon as he did, he was filled with dread. A second warning sign appeared but this time read second attempt at restricted access. Admin has been notified. Bailey felt fear grip him. The admin would be Megan of course and she would be sure to punish him dearly for going against her. Defeated Bailey closed the laptop and got back under the covers. Soon he gave in to his exhaustion and drifted into a fitful sleep.
As the night wore on Bailey tossed and turned eventually settling into a more natural position cradling the stuffed bear Amanda had left him. He was used to having Amanda next to him in bed and his body just held the bear just as he would when holding her while she slept.
While he slept his body was in turmoil. The three doses of high-level female hormones and the three doses of herbal breast enhancer were mingling and reacting to each other in a strange and powerful way. As Bailey slept his body struggled to hold on before slowly being overwhelmed.
The next morning Amanda went to wake Bailey and found him cradling the stuffed bear she had given him. Her heart swelled at the sight before she bent down and gently woke her with a kiss on the forehead. “Rise and shine sweetie we have another busy day ahead of us.”
Whats next?
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Girlfriend’s Daughter
Friday
A boyfriend finds himself to pretend he is his own girlfriends daughter so she can succeed at the office.
Updated on Aug 27, 2023
by Nicegent42
Created on Mar 6, 2021
by Nicegent42
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- 211 Chapters
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