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Chapter 40 by Nicegent42

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Dreams

Bailey opened his eyes and got out of bed feeling the compression of the corset around his body and the height of the heels on his feet. A glance at the mirror on the back of the room decorated for a teenage girl and saw a pretty blonde girl, her makeup done up and wearing a black over bust corset, tiny black panties, thigh high stockings and impossibly high heels. Instead of thoughts of why he looked like this his mind went to why he was awake. The sound of Mandy moaning caught his attention and immediately revved up his arousal. Stepping forward he opened the bedroom door and walked into what used to be his and Mandy’s room. Laying atop the bed he saw his girlfriend dolled up just like he was, with her hand down the front of her panties touching herself, before letting out a soft moan and whispering the name Derrick.

“No, you don’t need him. I'm your boyfriend Mandy and I’m right here!” he said, moving to the foot of the bed. The moaning stopped and Mandy smiled. “There she is, you can come join me if you call me mommy.” Bailey shook his head “No, I’m a man, not your daughter!” he said, stomping his heeled foot. Mandy’s face went back to one of bliss as she continued to move her fingers under her panties. “Too bad, only my daughter can join me.. Don’t you want to join me?” Feeling himself get hornier and hornier Bailey climbed onto the bed. “I do Mommy.”

Crawling between her legs Bailey started to pleasure Mandy with his mouth, the dream logic taking no consideration for where the panties went. “That feels good baby, but it isn’t what Mommy needs.” Stopping what he was doing Bailey looked up suddenly feeling worried. “What does Mommy need?” Placing one hand on Bailey’s cheek, Mandy smiled. “Mommy needs a cock.” Nodding Bailey went to reach down to his own lacy black panties when she stopped him. “No baby, you don’t have a cock. You are a girl, remember? But maybe you want a man’s cock too?” Panic washed over Bailey as he felt the front of his panties not feeling his own dick, it wasn’t tucked away, it just wasn’t there. “Mommy will spoil you, how about you get a new Daddy and fucked at the same time. Mommy doesn’t mind sharing.” Bailey wanted to scream no, but in the room walked Derrick fully naked smiling at the two women on the bed dressed sexy and ready for him.

“How about we have some fun with your Mom princess?” Derrick said, smiling as his hard dick pointed Bailey. Bailey went to flee, but just down the hall he could see Megan in the dark smiling. She was waiting for Bailey to mess up so she could ruin his relationship and beyond her at the front door waiting for him was Officer Cooper, ready to arrest Bailey if he saw him as a man. So instead he looked back to Mandy and then Derrick. “I am Daddy, I want to have some fun.” Derrick was then laying between him and Mandy, leaning over and kissing his girlfriend before turning back and doing the same to him. Bailey’s hand was moved to Derrick’s hard cock while he went back to kissing his girlfriend. Bailey looked away from the sight of Derrick kissing the woman he loved and down to the rigid member than his hand was rubbing up and down. “I always wanted to fuck a mother and daughter at the same time.” Derrick said as Mandy came down and ran her tongue the hard dick before smiling at Bailey. “You can do it too, suck Daddy’s cock, do it for Mommy.” Bailey didn’t want too, but he couldn’t leave the room and he didn’t want to lose Mandy so down he went, taking only the tip of Derrick’s dick in his mouth. The entire thing being way too big for him, much larger than his own. “That’s my girl, you know I always hated giving blow jobs, but you always loved them. Now you can have them whenever you want.” Bailey could feel Derrick’s hand on the back of his head pushing him down, more and more on the huge member. With his mouth full Bailey screamed, he didn’t want any of this. He was just horny and wanted to be with Mandy, not lose his manhood.

Bailey’s eyes snapped open and sat up in bed. He was in his own room, with no light coming in from under the door or the blinds. A look at the clock on the nightstand told him it was three in the morning. He was still wearing the clothes he left the park in, but he could feel the tuck kit had failed at some point as his raging hard on pressed against it pushing on the sticky material. Reaching below the skirt Bailey removed the kit and with it sprang his dick to its full height. Bailey wanted to believe it was just morning wood and not a product of his dream, god he hoped it wasn’t a product of his dream. With the pills he had been taking to keep erections from happening to give himself away he felt like he really needed this, especially after a dream where he didn’t have it at all. Taking himself in one hand Bailey reached over to the night stand for his laptop. Opening a browser he went to go to one of his favorite sites when he saw the site blocked and a warning on the screen. “I hate that woman…” A glance back to his hard dick and then to his computer Bailey opened up one of the videos Megan saved to the computer. He didn’t like the idea of a PoV porn from the woman’s perspective, but at least he could see something. With the video playing Bailey started to give himself a hand job. The video wasn’t much to his liking, but between it and trying to pretend it was Mandy and him in the video he was able to cum, using his own panties to hold his mess. Putting the laptop back where it came from Bailey layed back down and drifted back to sleep thinking he only had to do this for a few more days.

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