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Chapter 23 by Nicegent42
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The morning and the quiz
By the time Bailey got out of the guest shower, his shower for the week he once again reinforced the scents of jasmine and rose oil from the shampoos and lotions he has to put on after the shaving. A task he was not keen on at all. After it all though the memory of the dream had mostly faded, only lingering bits were something about Megan being a witch and him having red heels.
Showering with breasts and ones he couldn't feel was interesting, it was like he got to feel up a girl with nice C cup tits whenever he was alone. He may have jerked off right there in the shower if he didn’t hear Mandy knock on the door reminding him, they had places to be.
Patting himself dry like he was taught he wrapped the towel around his waist and stepped out into the hall only to be caught by Mandy once again. “Young lady, we talked about this. No daughter of mine is going to walk around exposing herself.” she said pulling the towel up and lightly pushing Bailey back into the bathroom. “I will teach you how to wrap your hair later, but for now we have to blow it dry.” she said opening the cabinet below the sink and rummaging around till she came out with her spare hair dryer. After a quick blow dry, she stood behind Bailey brushing his hair out just like last night.
The feeling was relaxing for Bailey even if the scenario was ridiculous. “We will be brushing this every morning and evening at least forty times with this natural bristle hair brush, not one of those plastic ones, that will ruin your hair.” she said happily smiling at the blonde hair with each stroke. If it didn’t feel so good to have her do it, he may have complained, but mostly he just wondered why he never had her do it before. “Off you go now, get changed for the day and I will be along shortly to help with your makeup.”
Tossing the large fluffy towel on the bed Bailey knew what the first task was, he needed to tuck again. He pulled out the Unclockable Tuck kit and followed the directions adding the pad to the sticky substance and sticking it to his skin just above his privates, a process that would be painful if he wasn’t hairless. He then pulled it back and pushed up gently with his other hand to push his testicles back inside his body and sealed them in with the sticky T tape it was called and when he did it correctly as shown he was able to use his thumb to create a crease at the center like a woman should have. The process was not painful, but was as always uncomfortable and the kit said it would even hold in water, perfect for the day. With himself sealed away he opened his drawers to get a swim suit and had a thought. Mandy wasn’t told they were swimming today and Candi wouldn’t be telling Megan anything. He smiled and put it away thinking he could just say he forgot and maybe they could spend the day watching tv. Sure it would be shows he didn’t like, but that is a far better than what was currently planned. To really sell it he needed to make sure he looked good. Pulling out some white lace cheekini underwear and a white lace push up bra he put them on. The push up bra really bothered him, he didn’t want these things on his chest to look bigger, but he was not spoiled for choice. At least with the tuck kit the lace panties weren’t be rubbing on him arousing him all day. Today was the first real day he got to dress himself as a girl and he kinda wish he didn’t just make the decision to do it well, but best to do this than wear a bikini all day. Pulling blue blouse from the closet that had sparkly bits around the chest and a criss cross weave by the shoulders instead of sleeves he pulled that on and looked for a decent bottom. Deciding on the black jean button up skirt from the day before he was proud of himself. It looks like something Candi would expect him to wear, the saddest part was the shoes. Other than a single pair of sneakers that would not go with the outfit he was left with heels, so he grabbed a pair of strappy gladiator looking blue sandal heels. “Why are all the heels so stilettos, dammit Megan.” he cursed under his breath and quickly redirected his thoughts, less they alone summoned the witch here. Before he went to Mandy, he needed to do something with his hair and he started to try to recreate what he did yesterday, but without the video it was difficult so he got little more than half way done and just put the rest into a pony tail. Turning his head in the mirror he decided it looked good.

Walking over to Bailey’s room fully dressed for the day minus her heels she looked into see the feminine sight of Bailey admiring his hair that he had braided and put up. She was reminded once more how hard he was trying for her, making the mistakes earlier with the towel seem like normal unthinking gaffs. “Aww Bailey, you look beautiful like a princess.” she said happily walking in with a makeup case. Bailey only scrunched up his face at the comment. “You know it is a compliment sweetie, my father God rest his soul use to call me that.” she said putting the case down on the vanity and squatting down behind Bailey so their cheeks touched looking into the mirror together. “With the way you look now it is easy to see why this is working. You have green eyes to contrast my blue, naturally darker eye brows and I have a longer face, but we really do like we could be related. You know how I always wanted kids, I know this is only pretend and something you did not want, but for this week. I am happy to have you as my daughter.” she said hugging the disguised man and then kissing him on the cheek.

“Now in this case I have some makeup you can keep in here, some of it is mine. Some of it is what Megan brought over from your cousin Becky. Let us get you looking even more pretty for the day. Like they say, a lady should never go anywhere without putty on her face.”
You are lucky to have clear skin Bailey so you don’t need to much, but we all have bad days. What you do need to know about is some basics, you need to have eye liner, mascara and lipstick, anything more only makes it better. I will try to get off work on time tonight so I can touch you how to do your own makeup. Aww do you hear that Bailey; I just love saying things like that out loud.” she ended the lesson with another hug. On the way out the door Bailey tossed a few more of the pills from Megan into the purse he was borrowing from Mandy, then popped one in his mouth and one of the vitamins from Candi dry swallowing them both.

Soon enough the two girls were in the two thousand and eighteen Toyota eighty six coupe driving to the hotel where Candi was staying. Amanda watching the morning traffic and Bailey looking down at his phone texting his new bestie. The topic of this morning's rambling was about a Cosmo quiz that she just took and Bailey was doing now about what your dream wedding dress says about who you will marry.
Question 1: Does the dress have any sleeves or straps? Answer: Nope! I’m going strapless.
Queston 2: How long is the skirt? Answer: Floor-length, Obvi!
Question 3: How poofy would the skirt be? Answer: I want a decent amount of poof.
Queston 4: Would you ever something trendy, like a two-piece crop top-skirt combo or jumpsuit? Answer: Nah, That’s not for me.
Queston 5: What’s your shoe game looking like? Answer: Some pretty heels, for sure.
Question 6: Veil or no veil? Answer: yes. I need my Meghan Markle moment!
Question 7: What kind of makeup do you want? Answer: I can never say no to a statement lip.
Question 8: And finally: what’s your main accessory? Answer: A pop of color, like some flowers in my hair.
The results of the quiz were: You’ll marry someone ambitious and romantic!

Bailey groaned and it caught Amanda’s attention so he had to tell her what he was up to. “Oh like Candi found a quiz that would like tell us what kind of man we would marry depending on our answers.” and then proceeded to go over the options he chose. He didn’t want to, but his girlfriend had an amused look on her face and asking him probing questions about his answers. The car ride went from peaceful, to annoying with the quiz to downright dreadful having to talk about how he wanted his wedding dress one day. The trip to the hotel was only about fifteen minutes thankfully, but before he could get out Amanda put her hand on his arm. “Forgetting something?” she said smiling wanting what was coming and to keep him in character. Bailey leaned over and gave Mandy a large hug. “Love you mommy, thank you for dropping me off and have like a good day!” with that he thought he was done but she stopped him again. “Bailey, Mr. Connors is going to give you a lift home. You know how important he is to us, make sure you treat him like how Candi has treated me, with kindness and respect. Make sure you thank him.” Another quick hug was given and a reply. “Like of course mommy, I’m a Best so that is what you can expect from me!” it was a cute line that Amanda just loved. She didn’t pull away right away, isntead watching Bailey strut into the hotel. “I wish Bailey would stop walking like that.” she said pulling out back into traffic on the way to the office.
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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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