Home and Punishment

When Derrick came back to his hotel suite, he smiled seeing the two girls sitting on the couch next to each other, both of them falling asleep leaning on each other while watching RuPaul’s drag race. It wasn’t late, Derrick had left the office a little early to make sure to get Bailey home in time for dinner with her mom. He slowly put his laptop back down on the kitchen table and pulled out his phone and took a photo sending the precious image to Amanda.

Derrick: Looks like they had a good day and wore each other out.
Amanda: Aww, that is the cutest thing I have seen all day. Thank you for sharing.

Walking over to the girls he turned off the tv and leaned down kissing Candi on the forehead. “Hey princess, I’m home.” his teen daughter slowly fluttered her eyes open and looked up smiling a small tired smile and sat up causing Bailey to slump over on the couch waking her up. “I saw the video’s you girls uploaded and I approved them for you Candace. I’m glad you two had such a good day together. I’m sure you two would love to stay together longer, but maybe a sleep over can be arranged another night. For now, I need to get Bailey home.” Candi stood up and stretched before giving her daddy a welcome home hug, while Bailey watched them with half open eyelids not sure of when exactly he fell asleep. Still in his sleepy state Bailey licked his strawberry flavored lips trying to wake up and remembered what Mandy told him this morning about treating this guy like Candi treated her. He thought back to the picnic when Candi hugged Mandy and what she said.

When Candi let go of her dad Bailey gave the larger man a hug himself and stood on his toes to give the man a kiss on the cheek. He wasn’t a fan of what he was doing or the feeling of pressing his lips to another man's body and feeling stubble, but he figured this is what Candi would do. “Thank you for like today, Candi is like the best.” when he said best it caused Candi to giggle and say “No, you are the best.” making a joke about his fake last name.

After they said their goodbyes, Derrick took Bailey home in his rental car. While looking out the window still trying to fully wake up after his afternoon nap he heard the man talking to him. “It is nice to see Candace taking such a strong liking to you, I can tell you both are having fun. She has friends at home, but the two of you seem to have something special. Like this sister thing I saw in the videos, how exactly is she your older sister?” the mention of his gaff made him blush, here he was a twenty-five-year-old man pretending to be an eighteen-year-old girl and referring to a seventeen-year-old one as older. “Umm that like just came out, you see um where to begin. Some boys thought we were sisters and she liked that and she says she is the big sister because she is like half an inch taller than me even though my birthday was like last month and hers isn’t until next week. But like she is more.. Outgoing so she tends to lead.. So that is why she says she is the big sister, but the older thing was like just me saying the wrong word.” Bailey was mentally congratulating himself he navigated that while staying in character, though he wanted to say pushy, not outgoing. “That is my Candance, always taking the lead and I can see why those boys thought that. With your blonde hair and green eyes, the two of you could be twins, not identical, but still.” holding back the groan, no man wanted to be compared to a pretty teenage girl like that and god he hoped he didn’t mention the twin thing to anyone else, the last thing he needed was that to get in Candi’s head.

When they arrived back at his apartment complex Bailey gave Derrick another hug and a kiss to the cheek as he did before. “Thank you again Mr. Connors, I like can’t wait to be able to drive myself.” smiling back at the girl thinking she was talking about when she could get her license he replied. “Think nothing of it, you will be driving before you know it. I’m not so old I don’t remember how excited I was when I got my own license, though from what I understand you don’t have a permit yet, because of bad grades. You going to turn that around next year?” Bailey had no idea what he was talking about, Mandy must have made something up for his background. “Like fer sure, I like to my best but you know how it is.” he said letting out a giggle hoping he sold the act. Keeping Candi convinced was difficult, but keeping Derrick Connors convinced was the real goal and only reason any of this needed to happen. “Good glad to hear it, Candace struggles with school too. Maybe you two could setup study time together online, two heads are better than one.” giving his best fake smile he climbed out of the car. “Sounds like a good idea, thanks gain.” he wanted to slam the door shut in frustration, but was able to contain himself.

Walking up the steps in the blue heels in the silence of the sinking sun he reminded of all the odd feelings. The movement of the breasts attached to his chest, the cool breeze at the end of the day on his exposed legs , the movement of the pigtails and the large hoop earrings. He was just glad the day was over and as he got to the door he remembered once again didn’t have any keys. With a sight he knocked on the door to be let into his own house.

When the door opened, he saw Megan with a large smile welcoming him home. “Welcome home Bailey, your mom said she had to work just a little late, but would make it home before too long and we should eat without her. Though after seeing your video on your diet and seeing the boxes that arrived for you.” she said motioning to the empty boxes by the front door. “Don’t worry, I put them away in the fridge for you and let Amanda know how dedicated you are to getting into shape.” Glaring at her he didn’t say a word after what happened last time. “Don’t worry, I’m not staying I just wanted to make sure you could get in, Amanda mentioned how you lost your keys. So, I went and had this made for you.” she held out a pink metal key on a flower keychain. Snatching the key from her he squeezed in his palm or at least went to when he stabbed himself with his long nails. “One last thing before I go diary, I got an email late last night about someone being naughty and trying to go to places they shouldn’t on their laptop, not once but twice. You know those sites aren’t for someone of your age.. If you need some release feel free to watch the videos I gave you. So, you have two options for being punished. You will hate them both. Number one is you pull up your skirt and get thirty spankings right now and another thirty later.” the idea of being hit thirty times was to much, let alone another time. “That is way too much... all I did was try to go to some sites that I go to all the time!” waving her finger in front of the feminized man she stopped him. “No, my lovely niece, Amanda’s ex-boyfriend went to those sites. You do not, and I told warned you about blocking them and still you tried to defy me, that is why you are getting so much.” he wanted to yell he wanted to punch the bitch of a woman, but most of all he didn’t want to be spanked like a child thirty times. “What is option two?”

“I’m so glad you asked. Option two is when Amanda comes home, you tell her how you were bad today, I don’t care what story you spin. But you will tell her how your dad used to spank you to make sure you behaved correctly and it always kept you on the right path and how you want her to spank you now say ten times, then after you will thank her for helping you.” Bailey’s mouth dropped open, on one hand he would get hit sixty times and knowing this woman she would come up with a reason to make that number go up or ask his girlfriend to do it. “I will ask Mandy..” Megan raised an eyebrow. “I will ask mommy to spank me for being bad today.” Megan smile and stood up giving Bailey a light hug. “Good, love you dear. You be a good girl and go grab your diary and sit on the couch next to me, I can’t wait to read about yesterday and today.”

Sitting on the couch with his legs crossed at the knee, still wearing his heels because Megan gave him a tut tut sound when he tried to take them off, Bailey sat next to her writing in with a purple pen about how today went from the perspective of a teenage girl. He wasn’t even halfway done when they both heard a knock at the door. “Stay here pumpkin, I will see who it is.”

Opening the door Megan saw Bailey’s best friend and drinking buddy standing before her. The same man he was planning on running off to Vegas with to spend the money he was hiding from Amanda. “Well, hello there Charles. What can we do for you?”

“Megan, always a pleasure to see a beautiful woman like yourself, I was wondering if Bailey was in. Afraid he hasn’t been returning any of my calls or texts these last few days. Said the five-foot eleven man with dark well-groomed short hair and beard. “Charles, I haven't seen your lowlife of a friend in days either and all of his clothes are gone, but Bailey is here. Just not the one you are referring too.” The man before her gave Megan a perplexed look and looked behind her to see a scared looking blonde girl writing in a pink book dressed up like she was going out on a date. “You look confused Charles, come inside.” she said motioning him in.

Bailey’s panic meter was dialed up to eleven on a ten-point scale, his best friend Chuck was here saying he had been trying to get a hold of him, but he hadn't seen any missed calls or texts and yet Megan that bitch was inviting him inside the apartment. “I’m guessing your shit of a friend didn’t tell you Amanda had a daughter with the same name as him. Well, here she is this is Bailey Ann, she is eighteen. Bailey this is Charles, he was a friend to your mom’s Ex-boyfriend. For his part Charles only laughed at Megan’s statement. “It is a pleasure to meet you Bailey, you are a pretty one just like your mom and aunt here.” Megan was all smiles seeing him squirm and how even his best friend didn’t see him for who he really was. “Well dear, don’t be rude, say hi.”

Remembering rule one and trying not to get caught he smiled sheepishly looking at his friend then to the ground wishing it would swallow him up right now. “Hello sir, thank you for the compliment.” nodding and smiling at the demure girl Charles looked back to Megan. “Megan I know you and Bailey were never a fan of one another, but I think the two of us got off on the wrong foot.” He said holding out his hand to the older woman. “I do go by Chuck to everyone, but if I’m honest I like the way you call me Charles. I was hoping that maybe I could give you my number and you could give me a call if you see my friend or if you ever wanted to get a drink.” the twenty-eight-year-old man hitting on her was not something Megan expected or Bailey for that matter. She took his hand lightly and he shook it lightly before bringing it to his lips and kissing the back of it. “I hope that is a yes.”

Megan blushed, Bailey was surprised to see the forty-year-old being hit on and accepting it from his own best friend. The two of them kept talking for a while and the sight of it was just making Bailey more and more angry. He had nowhere to go, he was sure if he got up and left drawing more attention to himself Megan would punish him for it, or worse something he did would remind Chuck of who he really is. Instead, Bailey just looked down to his diary and focused on his writing. “Oh, that would be lovely. Bailey dear did you hear that. Charles here has a younger brother that is who your mom’s ex sold his old bike to and he thinks the two of you would just hit it off.” Bailey’s purple pen stopped as he looked up in fear and disbelief. “Look at her being shy, don’t worry dear Auntie Megan will set it all up for you, he is twenty-two, and I know how you like to date people older. Though...” she trailed off looking at Charles. “I can see why Amanda dated someone younger for so long.”

When Charles left, he was told how Bailey was recently given her own phone, the one that once belonged to Amanda’s ex once he was out of the picture the phone was on her family plan so he wasn’t going to take it with him. While Bailey saw in the phone how his old friends' number was blocked and notifications for it were turned off. Instead of yelling and freaking out at the idea of Megan trying to setup him up on a date with a kid who looked up to him he focused on his writing. He was so focused that he never even noticed Megan leave. What brought him out of his focus was the door opening and Mandy saying “Good evening honey, sorry I had to work late.” This day was to much and he got up and minced as fast as he could in his heels to hug his girlfriend a few tears in his eyes. “Today, was like so hard... please just hold me.” with one arm pinned by the hug Amanda put down her bag and hugged Bailey back. “Tell me about your day sweetie, I heard you made a plan for your diet with some smoothies, I am proud of you for doing that instead of just winging it. Now come on, let usgo sit on the couch and you can tell me about your day.”

Opening up and telling Mandy about his day he had just finished telling her about how he had to babysit and how little Mikey didn’t want to let go of him when he remembered the whiskey he drank and Megan’s punishment. “Umm.. Mommy I need to ask for your help. You like said you would help me stay in character and it is like super hard. This is not something that I like.. Would do. But today I messed up and almost got caught.” Amanda put her hand on Bailey to show support. “I umm drank someone Derr.. Mr. Connors whiskey and Candi almost caught me. I just needed something to help take the edge off and it was right there.”

“Of course I will help you, what can I do to help you stay in character Bailey?” looking down at the floor before grimacing. “Well like my mom and dad used to spank me when I got out of line and it always put me back on the right path. The thought of getting another spanking tended to keep me from making the same mistake. Could you umm.. Give me ten spankings for drinking when I’m not supposed to be old enough to?” Amanda took a deep breath, it was request she was not expecting. Her own parents did it to her or she got the wooden spoon. “Sure honey.. Why don’t you lay across my lap.”

Hiking up his skirt and exposing his pantied bottom Bailey already read in the face lay across his girlfriend's lap ready to be punished because of that bitch Megan. When the first strike came down Amanda flashed back to one evening in the bedroom with Bailey. He had always been the controlling type and doubly so in the bedroom, and she went with it for the most part. She was the boss or a boss at work and had to make the decisions, sometime it was nice to be the one not having to come up with everything and be the submissive one for a chance. That night her hands were bound in a leather set of cuffs that were chained to the headboard with her legs spread apart by a bar attached to her ankles. She had her hair up and the only clothes was an over bust corset with garter belt attached to sheer black stockings and tall six-inch heels. She was on her knees on the bed ass in the air as Bailey spanked her.

“Tell me you have been a bad girl..” Bailey whispered to her.

“I have been sooo bad, I need to be punished.” she replied playing along with the bedroom game. A hard slap came to her ass before he continued. “Tell me you are my little slut and you want me to punish you.” he said slapping her ass again. “This slut needs to be punished, spank me!” she called out before a few more slaps came down. “That's right you do need to be punished, but we can’t have the other neighbor complaining about how loud you are my little slut.” he said putting a red ball gag into her mouth and latching it behind her head. Amanda remembered being spanked again and again, and while she wanted the game to end the gag kept her from saying so, all she could do was make noises. “AHMMJMM” she would try to call out for him to stop, but he only replied with “OH you like that don’t you.” before giving another swat. She wasn't’ sure how many times he spanked her before he turned her over to start to fuck her hard. The game should have been over, sure they were going to have sex but the spanking wasn’t supposed to go on that long and has he drove is cock in her over and over again she was lost in a world of both pleasure and pain and the feeling of being helpless.

The two of them had done some bondage after that night, but never again did she agree to the ball gag.

Smack, she laid her hand down hard on Bailey’s back side for the eleventh time. “Now that was one extra for you to remember this lesson missy. You are just lucky I do not ground you for what you did. For now though you will apologize to me for misbehaving, drink one of your smoothies and go get ready for bed. I will be along shortly to brush out your hair.”

Holding back some tears Bailey nodded and looked down at his phone seeing a text from Candi. The time on the screen said Seven thirty-five. “It's like still early though, I was hoping to spend more time with you.” Amanda stood up and fixed her skirt. “When teenage girls get in trouble they go to bed early, now go get your smooth and march on to your room missy.” the words were firm and commanding, like how he was sure Mandy spoke to her employees when they did something wrong, a way she had never spoken to him before, though his own words she was now trying to make sure he played his part as her daughter, all because Megan couldn’t keep her nose in her own business.