Chapter 8
by Nicegent42
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Scene 8
Scene 8
In his bedroom Aaron sat in his bed, everything from the waist down covered with a heavy frown on his face, the dark circles under his eyes adding to his morose visage. He was doing as he was told with what he had to wear, but wasn’t going to give someone the chance to catch him wearing the very feminine articles. When he got up he no longer was having problems standing in the glossy black seven inch stiletto heels with two inch platform shoes and was able to keep from toppling over when he walked, but he wasn’t exactly graceful like his sister insisted and he was definitely not enjoying the choice of footwear, not his choice, but someones. Wearing the heels to bed to help make them feel comfortable as Evelyn put it didn’t seem to be working, but what it did do was jump his anxiety up as he lay in bed wearing lace panties and fuck me pumps. Not to mention the almost complete lack of sleep, the things were not comfortable to wear at all. Yet every time he was alone he had to put them on and practice walking around his room. Aaron was at least thankful his room was carpeted, not wanting to imagine how quickly he would have been caught walking on the hardwood floor that was in most of the house.
The first day he was **** into the shoes his bitch of a sister pretended like she was helping him, as she made him walk up and down the hallway, the heels on his feet clicking with each step. The sound that he normally found thrilling was turned into something closer to nails being hammered to seal him in a coffin. Now he was in his room feeling like it wasn’t even his space any more, Evelyn just seemed to walk in without knocking and today she brought with her a new way to **** him.
Evelyn had put her ear to her brother's door and only heard the music that he had playing on his computer. The last thing she wanted to do was walk in when the pervert was jerking off, something she was going to put an end to. Throwing open the door like she owned the place she stepped into her siblings bedroom and cocking one hip to the side as she came to a halt in the middle of the room, the black paper bag said the word Intimates in pink with the female gender symbol below it. Her eyes landed heavily on her brother who was sitting in bed with the covers pulled up to his waist as he sat there propped up by pillows as he read a school textbook. “Inspection time.” She declared.
“Eve, can we not? I’m trying to study, I have a quiz tomorrow.” He said, exasperated.
The twenty year old young woman raised her eyebrows slightly before giving a firm one word answer. “No.” Before motioning him to get up. “Little sis, just flirt with a cute boy and get him to give you the answers to the test, it works every time.”
“I’m not…” Aaron stopped himself from saying anything further, it wasn’t worth the aggravation. Closing his book he put it on his night stand before tossing the blankets back to reveal his lower half. His legs were partially on display with the elastic band basketball shorts he was wearing, it being too hot to wear pants underneath a blanket and of course his stepmother's shoes he was wearing were on display and at this point he was sure he had worn them more than her. “Happy now?”
“Mostly, but I think I can turn that frown upside down little sis.” She said holding up the bag in her hand and giving it a little shake.
“Unless you have a folded up piece of paper in there that says you are going to leave me alone and a stack of cash to reimburse me for what you made me buy and what you bought with my own money… yes I know you stole cash from my wallet. So yeah, unless that is in there I’m not interested.” Aaron crossed his arms, knowing damn well that wasn’t what was about to be produced.
“Erin… Erin, Erin, Erin.” Evelyn said as she shook her head slowly from side to side. “I didn’t steal from you. I mean yes I took money from your wallet, but it was to buy those white cotton panties you wanted. I can hardly reimburse you when the money was spent on things you wanted.”
“You know damn well I don’t want any of this you bitch.” He snapped back.
“I really dislike your attitude, little girl but I’m going to ask you one simple question, yes or no. Do you want me having a conversation with Dad about you or for those lovely photos of you getting out?”
“N… No.” He answered, his anger being deflated, wishing his rage didn’t bubble up like that.
“Then you wanted me to buy those for you, because it is either one or the other. So, if and only if it is true, I want you to say thank me for helping you become the good girl you want to be. I mean, it is either that or the alternative.” Evelyn cocked her head to the side, her mouth practically salivating at what was coming next.
Moving his jaw like he was chewing on the words Aaron couldn’t bring himself to even look at his sister. “Thank you for helping me become the good girl I want to be.”
Putting the bag down on his dresser Eve pressed her hands together as she faced her brother. “Little sister, it is a pleasure, truly and on that note I got some goodies for you. Come here and see!”
Getting out of the bed Aaron put his heeled feet together like he had been taught before standing and made a few mincing steps closer to his dresser, the heels he was perched in more than making up for the three inches in height his sister normally had over him. His new height didn’t give him any confidence or make him feel domineering, no they did the opposite and when he saw the first thing she pulled out of the bag his eyes would have fallen out of his head if he was a cartoon character with how wide they went. She was holding a bra, a slightly odd looking one, but still she was holding a light pink bra. “No…” She had made him wear a bra the other day when she first made him wear the crazy shoes, but this was different, this was something he was sure she had bought for him.
“Yes.” She said with a smile. “It is a travesty that you don’t have bras little sister, I know you aren’t developed, but if I let this go on little Dotty would be in training bras before you wore something proper on your chest. What I got for you here are two sports bras, they were pretty cheap, but what I got here is called a magic bra, or a magic thick cup push up bra, just the thing you need. I have five of them in different colors so you have some variety and get this, they were on sale from ninety nine dollars all the way down to fifty five! That isn’t even the best part, I signed you for a membership at Intimates and that brought the entire bill down by another ten percent! Don’t you just love your big sis?”
‘Five of them.. Ten percent off of fifty five, plus whatever she spent on the sports bras…’ He quickly did some mental calculations. “You spent over two hundred dollars of my money on bras?” He asked in a tired voice.
“Yep, saved you a pretty penny. Speaking of pretty Erin, those circles under your eyes don’t look good. When we are done looking through your new things, let's get some concealer on you and then we can talk about why you aren’t sleeping.”
“Eve…” Aaron took a step backwards, stumbling slightly, but catching himself before tumbling to the ground. He didn’t have that kind of cash in his wallet, that meant she had taken his debit card. “That is money I have been saving for a car, it is the money mom left me.”
“Please.” Evelyn rolled her eyes. “Mom didn’t leave us anything, that was just money from Dad. You need what I’m getting for you and if you don’t want to spend your money I bet if you hopped in Dad’s lap and gave a pout asking if Daddy would buy his little girl things she needs he would be happy to.”
Aaron’s anger was hardly ever in any real control and it had gotten him into plenty of trouble and seemed to only make things worse with his sister and her plan to strip away his masculinity, but without the control he needed to stay calm it burst forth once more.”You know what Eve… Evelyn Bright the Bitchiest of the Bitches! You can just Fuck off. THen keep fucking off, keep fucking off until you get to a gate with a sign saying you can’t fuck off past here. And you know what!? You can just climb over that gate, dream the impossible dream and keep fucking off forever! That is what you can do.”
The outburst was surprising to Evelyn, she hadn’t heard her brother explode like that, but seeing him clutch his hands into fists, his chest heaving, but doing it all while keeping his balance in those shoes just detracted from it all. Placing one hand to her chest like she was hurt by her words she bit her bottom lip and shook her head, causing her dirty blonde hair to flutter about. “I Just can’t…” She spoke like she was holding back tears. Clearing her throat she then spoke in a much harsher tone. “I just can’t believe the filthy mouth on you little sister. I told you there would be consequences and you just don’t listen. So I got you, and you paid for it, something that will just be perfect to keep you remembering the pecking order.”
Releasing his hands that had been held closed so tightly that his fingers were turning white, Aaron watched his sister look in her bag, the bra she had been holding had been tossed on his bed forgotten. It felt good, so good to say that to her, but that personal victory that felt so cathartic was followed by a feeling of dread. “Hey, ahh I’m just angry, I’m sorry, I didn't mean that.”
Looking over her shoulder Evelyn gave her brother an evil grin. “No, you meant it and sisters have little spats from time to time. I’m sure in the future I will be just as mad at you for borrowing a blouse or dress from my closet that you immediately go and ruin, for now though, you have to pay the piper.” Turning around she held out a pink silicone eight inch dildo with a suction cup at one end that she had just taken out of the packaging in the bag. “Don’t worry this was only about fifteen bucks. I’m surprised you don’t have one already, an eighteen year old girl and doesn’t even own a dildo.”
“The… the… FUCK?!” Aaron didn’t feel like he could move he was in such total shock that his sister whipped out a fucking dildo and commenting on the price like that was what he was worried about.
Moving quickly Eve stepped into her brother's personal space pointing the dildo at his face, less than an inch from his mouth. “The fuck, is what is going to be happening between your new toy and that little mouth of yours. You can’t seem to keep foul language and insults out of it and aren’t smart enough to keep it closed, so now you have something to keep your mouth occupied. Now Erin, open your fucking mouth.” The tone of her voice grew harder the more she spoke. The second his mouth opened even a little she shoved the tip of the phallic object in and grabbed his hand so that he could hold onto it, not wanting to think of the visual image of her holding a dick and feeding it to her sibling. “Hold it there if you know what is good for you or I swear it will go in another hole.”
Aaron felt like he could throw up, the thing in his hand wasn’t colored like anything lifelike, but it shaped like it was, complete with veins and a tight ball sack. He wanted to throw it to the ground like it was a snake or use it as something to bludgeon his sister with, but that extra threat of where she would put it… his sister wasn’ that much stronger than him, or so he thought, but three was no way he would able to run, or properly struggle in the shoes he was in. So, there he stood with the tip of the fake cock in his mouth, ready to throw up or cry, maybe both. ‘Why did I say that to her!?’
Stepping away Evelyn took a calming breath before removing the other bras from the bag and put them away in her brother's top drawer. “Now, we have a few more things to go over Erin.” She said looking back to make sure her brother hadn’t taken the dildo from his mouth. She stopped what she was going to say and focused on what he was doing now. “If you want a more realistic feel you can warm that up. If you do use a bowl of water you heated up, but never and I mean this, never put your toy in the microwave and to change it up you can get some flavored condoms.” She then held up one finger when she saw him start to move. “No, leave that there, you are going to have to learn how to take that… Now I don’t think you are a slut or anything Erin, so it isn’t like I expect you to be deep throating it, but… that would win some points with me.”
Feeling his legs go weak Aaron moved to sit down on his bed, he thought things were bad before, but he had no idea how bad they could get.
Taking the last thing from the bag Evelyn put a box on top of his dresser. “These… what you got here is something special. It is a box of Unclockable tucking kits, it will solve that little growth problem you have between your legs. From what I understand over the course of a day you should only need to use two of these to hide away your bits. Don’t worry you didn’t have to pay for them, this box of ninety cost just over three hundred after taxes. They seem expensive, but to give you that nice smooth front I think they will be worth it. Going forward on weekends and right after school you will be wearing these. I mean if I come into you bedroom in the middle of the night I expect you to be wearing this along with your other little things to help you be your true feminine self.
“Oh.” Aaron said weakly, not sure what else to say before it occurred to him that she hadn’t made him pay for them, an odd thing considering what else she had used his money for. “You bought these for me?”
“Me?” the brown eyed girls said as she pointed to herself. “No, you ordered them or at least someone on your computer ordered them using Mom’s Amazon account. That credit card is set up to auto-pay, so I would imagine she wont know. ‘Unless she looks at her order history.’ She mentally added.
Feeling so very numb the fake dick fell from his mouth and his hand and landed on the floor. ‘I don’t deserve this! Do I?’
“Silly girl, you can’t let this fall on the floor. Now why don’t you pick that up and give it a good rinse off. We can then find a good place to put it, someplace waist level, hmmm. That way you can practice, but I think you should put on your new bra first.” Evelyn said, pointing to the bra she had tossed on the bed. “Oh! And was last thing.” She said faking what she was about to say was an after thought. “From now on if anyone in the family, Dad, Mom and you know I mean Dalila, Dotty or myself tell you that we love you. The polite response is I love you too and by polite I mean what you are going to say back every time or you will be getting a butt plug.”
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Tricked to be a Treat
Scene 1
Eighteen year old Aaron has done some horrible things and is blackmailed by his older sister Evelyn to do little things like her chores in order for her not to tell their parents what he has done and a few made up things just to make it worse. The biggest of them is to be dressed up as a girl for Halloween and to make sure he is ready, she helps him along to bring out his feminine side the weeks leading up to the holiday.
- Tags
- crossdress, crossdressing, feminization
Updated on Nov 19, 2023
by Nicegent42
Created on Nov 19, 2023
by Nicegent42
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