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Chapter 3 by Nicegent42
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Scene 3
Scene 3
Moving across the living room Greg was feeling more steady in the heels than he did the day before. It was so odd to be wearing clothes that felt so light on his body, yet feel so confined in them. The bra straps dug into his shoulder, the current girdle he wore was like this super tight skirt that had tabs coming down that he had to attach to seamed stockings, that his mother made sure he kept straight. Unlike the first time she dressed him up he was also wearing a corset that looked more like it was made for bedroom play then wearing under clothes like he was now. What he did know was that the thing kept his back straight, making it difficult to do much of anything. His mother just told him to breathe from the top of the chest and that he would get used to it. The green pleated skirt wasn’t bad, it actually felt great when he moved with the softer lining underneath. The stockings were a pain in the ass, but they too felt nice on his smooth skin, not that he would admit this to his mother or anyone ever. The biggest pain was the pair of black four inch pointed toe heels he was wearing. They had a large buckle and strap around his ankle and he had been instructed to not try and take them off.
“Genna, if you take these off one more time before I tell you too I swear I will find a pair of six inch pumps and padlock them on your feet, you will even have to sleep with them on if you don’t behave yourself, young lady!” The threat was one thing, and one he believed she would carry out, his mother seemed deadly serious about them needing this to come through. The young lady and missy talk were truly getting to him though. He had agreed to this foolishness, the stakes were real for him too if this didn’t go through, and he really wanted that money. Still though, she could at least acknowledge he was her son. “Your shoes are just sooo cute! I just love that dress on you.” Greg said to no one as he walked around the room. He didn’t have to just practice walking, moving, sitting and looking happy all the time, but he needed to practice sounding like a girl named Genna too.
“Your walk is much better than yesterday Genna. I guess spending a day with your thighs taped together taught you something about walking like a proper lady.” That was another thing he had to be. She wanted him to not only pretend to be Genna, but be a proper lady. She had him brushing his hair out a hundred times every night, practicing makeup and doing his nails. He couldn’t believe it when she moved his computer desk out of his room and into the garage to make room for a vanity of his own. If that wasn’t bad enough she added a little paint to his room, the white walls were fine and normal for anyroom, but when she added a bubblegum pink glossy paint around the room where the walls met the ceiling it changed everything.
“What if your grandmother wants to come see your room? I think we might be able to find a poster of a shirtless fireman or something like that at a box store. That might be enough, but maybe a stuffed animal or two. What is your favorite animal, Genna?” When she had asked the question it bothered him because any answer he gave would just end up as a stuffed animal. Him not answering ended up getting him more than a few stuffed animals and her deciding his favorite animal was a giraffe.
All of that was before, now he had seemed to get some control over this bizarre training week. Like she was saying his walk was better, well girlier, but he still had a long way to go on his voice or so she said. “Mom, if I'm doing better can I just sit down for a bit?”
“Hmm, you may sit. So long as you sit like a proper lady.” Sitting with his leg crossed, one leg over the other was not the most comfortable way to sit, but it was a lot easier when his member was tucked back. “Here, take this magazine and read to me out loud about last year's winter fashion. The magazine is a little old, but it will do plenty to keep you in the right frame of mind and practice your voice.
Outside Marcus had been walking up to the house to see what was going on with his friend, and hopefully he had seen reason. Movement caught his eye through the main window in front of the house, the curtains were drawn, but with the gap he thought he saw a young woman walking around. Instead of going to the front door he moved closer to the window and heard the voice of Mrs. Abella and Greg and then the voice of a girl. Peeking in the window through the gap in the curtains he couldn’t believe what he was seeing. A pretty dark haired girl was sitting prettily on the sofa reading from a magazine, but as she read out loud he heard the voice of his friend every so often. Each time he did the girl earned a chiding from Mrs. Abella. “Genna this is exactly what I keep telling you that you have to keep talking like this so you don’t mess up. What would happen if your grandmother heard such an ugly male voice coming from such a pretty girl?”
“Holy shit…” Marcus whispered to himself as he pulled out his cell phone and took a few photos. Greggory The Terror was dolled up like a girl and while he knew he was coming over here to find out and try to talk him out of his plan, it still took his mind a few seconds to figure out why. He never would have thought Greg would do something like this for one of his pranks, but this wasn’t exactly a prank. He wanted to hear this from the source and thought how good it would be to catch it all recorded.

Moving up to the front door Marcus knocked three times and waited. When Mrs. Abella answered the door he gave a friendly smile to the older woman. She was a beautiful woman, he and many schoolmates would agree she was a milf. Not something Greg liked anyone saying around him. “Hey I just came by to talk with Greg.”
It wasn’t lost on him that she closed the door just a little at the mention of her son’s name. “He went out of town till next week, something about a job or a concert. He is always leaving with little notice, you know how he is.”
He could imagine she was being protective of her son, of course if she was dressing him up as a girl to scam his grandmother it sounded more like using than protecting. “Maybe you could just tell him I’m here. He told me about the little scam you plan on running. If she is his grandmother couldn’t you just ask her for a loan instead of trying to steal it from her?”
Cynthia’s face darkened as she looked at the eighteen year old boy in front of her. Her son spoke too freely, even if this was his best friend. He had gotten in trouble almost as much as her son, sure he claimed it was Greggory’s fault, but she doubted everything could be put on his shoulders alone. “Listen here Marcus, I put up with you and your influence on my son enough, but I will not have you sticking your nose in family business. I don’t know what tall tale my son told you but throwing a party for my mother in law is not a scam. Now I suggest you head home, unless you want me to make a few phone calls and make life a little worse for you.”
The pure venom that dripped from her words caused Marcus to take a step back. He knew she was a powerful woman and wasn’t going to call her bluff. In this neighborhood the police always arrived in less than five minutes and if he could get the police to listen to the recording he was making things would be fine, but considering who she was… the police might arrest and then ask questions later. “Got it, I’m umm… gonna head out then “ He said, holding up his hands at chest level as he took a few more steps backwards, before turning around and walking away from his friend's house. “Threaten me, will you! If you or Greg think you are going to get out of this scott free, you have another thing coming…”
As he walked back to his house Marcus looked at the photos he had of his friend dressed up as a girl. He didn’t take a good look before, but now he was really surprised at how pretty the girl in the image was. With the way she was sitting he could make out the top of stockings, the girl wasn’t just pretty, she was sexy.
“Who was at the door, mom?” Greg asked coming out of his feminized bedroom that he hid in when he heard someone at the door.
“Nothing you need to worry about Genna, mommy took care of it.” Put a little fear of god into the boy and he went running. She should have taken a more serious hand in raising her son before, she just didn’t have it in her to keep such a tight grip after Jackson passed. A mistake of the past, she was going to get everything taken care of. Greggory was going to act the part of the perfect daughter, Brandi would give them the money they needed to get them out of the hole she had gotten them in and then she could mostly go back to ignoring her. Maybe she would have Genna give her a call every now and then to stay in touch so that she stayed in the will. Greggory wouldn’t like that, but if she threatened him with a monthly visit instead of a phone call he would comply.
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Blackmailing the Scammer
Chapter 1
Greg and Marcus had been friends since second grade and Greg loves to pull pranks. The fall out of Gregs numerous pranks often fell on Marcus. When Greg's mother devices a scheme to her mother-in-law by disguising her son as a girl. When Marcus finds out, he forms a plan of his own. This is a spin off story from Jordan's Job.
Updated on Oct 22, 2022
by Nicegent42
Created on Jun 19, 2022
by Nicegent42
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- 13 Chapters
- 13 Chapters Deep
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