Son Becomes Daughter Ch. 01

Erica kept her eyes locked onto her son's face as Jenna got up and walked away. "To start, you will no longer wear men's clothing. In or out of this house." She saw his eye widen. "I also, was not flattered that you were wearing my panties. Watching you jack off didn't bother me as much as that you where in my panties. So with that rule being stated, I want you to strip."

Charles could barely understand what was happening. He took a glance at Jenna, who was bringing over all the bags that his mother had purchased the evening before. He pulled off his tshirt and dropped it to the floor. He looked back at his mother and he used his thumbs to hook the waist of this shorts. He smiled and bit as he slide down his shorts and let his raging hard cock out. It was pointing straight at his mother and he stood up and stepped out of his shorts.

Jenna gasped before dropping the bags at his feet. She smiled and bit and stated, "it is bigger then George's cock. And he was good recovery too."

Reaching out she wrapped her fingers are Charles's hard cock. She let you a moan of pleasure as if she hadn't touched a cock in such a long time. Slowly she became stoking his cock. With her other hand she slowly caressed his smooth ass check before giving it a light smack.

Erica leaned back and smiled brightly. "So starting today you will only wear woman's clothes. We've got you started with a few things, but if you need to buy anymore clothes then you'll have to go out to get them yourself or with one of us."

Jenna got down on her knees and continued to stroke his cock. Very slowly she stuck out her tongue and licked the sensitive tip. Erica watched her best friend slowly pleasing her son and she continued with a few more rules

"Now, last night you were given a blowjob from me, but if you want any chance at more then that, you'll have to earn it. That will only be granted to from Jenna. Once Jenna says that you are allowed more then my hand or mouth, we will progress in further. Also, you are not allowed to masturbate without permission. And I don't want you walking around too long with a hard on, so you need to tell us whenever you get hard. We will handle it when we see fit. At this point, your pleasure is in our control."

With that Erica got up off the couch. Charles could feel Jenna stroking his cock as he watched his mother walk out the room. He looked down at Jenna as she wrapped her lips around his cock. She bobbed her head over his cock as she sucked as hard as she could. He was going crazy. After being blown last night by his mother and having Jenna's lips around his cock he was in heaven. The thought of only wearing women's clothing around the house had always been a fantasy of his, and now he was about to live out that fantasy.

Charles looked down at Jenna sucking his cock. She was sucking hard on it and both hands were grabbing his ass cheeks. She was able to take all of his cock down her throat but not as easily as his mother was. Releasing his ass cheeks she took his cock out her mouth. She held onto his cock while she licked slowly down the sensitive underside. She began jerking him off fast as she took on of his balls in her mouth. She sucked hard on it and pulled until it came out with a pop.

She leaned back on her heels and released his cock. Looking up at Charles she said, "stroke you cock. I want you go shoot your cum all over my face and mouth."

Doing as he was told, Charles began stroking his cock. It was extremely slick from all the saliva coating it. He aimed the tip directly at Jenna's face. His hand was jerking his cock really fast. Deep down inside he wanted to shoot his load all over a woman's face and now he had one telling him to do it. He felt his balls swell and he knew it was a matter of seconds before he exploded. And right on que he exploded. The first shot flew out landing in her hair and forehead leaving a trail all the way down her nose. He kept his cock pointed at Jenna's face and his second load blasted out and landed on her upper lip. Jenna opened her mouth and stuck out her tongue catching the last of the cum as it oozed out. She licked the tip of his cock making sure she got it all. Using her fingers she wiped up the cum off her face and began licking them clean.

With a smile she got up and leaned over giving Charles and kiss. She forced her tongue passed his lips making sure he could taste himself. Breaking the kiss her smile brightened even bigger.

"That was almost enough to pass," she said stepping aside. "I'll give you credit, you can really last before you came." She stepped to the side and slapped his ass firmly. "Now go to the couch and bed over."

Not fully knowing what was going on he took a few steps and leaned over placing his hands on the back of the couch. He had never been in a position like this before and it felt awkward. Jenna knew what she was doing. She caressed his ass gently before giving it another firm smack. Very carefully she got down on her knees and kissed a cheek. She ran her tongue from that kiss all the way to his ass crack. She kept running her tongue between his ass cheeks and she used her hands to pry them apart.

His ass was very clean. She massaged his ass cheeks a bit before he spread his cheeks wide. Leaning forward the licked his puckered anus. His puckered hole flinched at the warm wet touch. She continued to run her tongue in circles around his ass and even gently poked at the tight entrance. Sliding her hand closer to his puckered hole she stuck her finger in her mouth getting it wet. With her wet finger she pressed it lightly against the dark entrance. He clinched his anus but with a smack on the ass he relaxed.

"So have you had anything in your ass before?" Jenna asked. "You can use words."

"No Jenna," he replied.

"That's okay," she said. "Me and your mother will be the firsts of many things."

On that note she slipped the tip of her finger into his ass. It was tight and after a few seconds the grip on her finger loosened up. This allowed her to slide more of her finger into his ass until the entire finger was buried in his ass. Pulling her finger back she spit on her finger then slowly reinserted it. She began fingering his ass. Every few moments she would move fuck his ass with her finger harder and harder. Charles was grunting with each thrust of her hand until he began to feel the finger rub over his prostrate. His grunts turned into moans.

Charles was beginning to love the feeling of her finger in his ass. It was sending waves of pleasure and making him feel more like a woman being fucked. He also noticed that his cock was not really going soft but it wasn't fully rock hard either. Then out of no where a wave of pleasure ran up and down his spine. His toes curled and it felt as if he had just came but nothing shot out is cock.

After the wave of pleasure began to fade away and the spinning in his head allowed his vision to return, Jenna slowly removed her finger from his ass. It was still twitching and she sat there watching until his anus returned to normal. She got up and started walking towards the kitchen, leaving Charles in the same position. After washing her hands she came out and saw Charles was sitting on the couch looking through the bags.

"Your mother and I are going to take good care of you after this," she said sitting down next to him. "Everything you need to get started in in those bags. It is a start. We expect you to be dressed and if you need assistance with anything, just ask. Either of us will be here to help. But remember you need to learn to be able to take care of yourself. So start doing research in your spare time, makeup isn't something you learn overnight."

With that Jenna left out the front door.