Josh's Journey Ch. 05

Warning!! If a description of a mom giving her son an enema will offend or gross you out, don't read this installment of Josh's Journey!

Emily stood between the shower and the toilet, naked, while his mother filled the bag with warm soapy water. He could smell the flowery lavender scent as the bag filled. There were tingles in his stomach as he wondered if Paul would get a whiff of the pretty scent on his ass.

"Now, bend over and grab your ankles," Edna said as she attached the hose to the bag. She was naked, too, having decided that if they made a mess it would be easier to jump in the shower to rinse off than to try to change wet clothes.

She stood beside her son, the nozzle from the bag in her left hand, her right hand on his bare ass. She rubbed her hand around his ass and lower back to help him relax, then ran her fingers up and down his crack.

Emily felt the tingles increase, and felt his cock start to swell just a little. He tried to relax. His mother had put her fingers in his tight back hole a couple of times, and he'd put the silicone dick in it quite a few times. But now, with is mother standing beside him to administer his first "douche", as she called it, his nerves were on edge.

Edna felt his muscles tense when she put the hard plastic tip of the nozzle against his pucker. "Relax, honey," she said softly as she rubbed the tip of her finger around the tight hole. When she felt him relax she put the nozzle against him again and pushed gently. She'd rubbed lube around his hole. She'd also put some of the lube on the nozzle.

She heard him sigh when the nozzle slid easily into him. She held it in place with her right hand and reached up with her left to open the valve to let the scented water drain into him.

"Mmmmm," Emily moaned when he felt the warm liquid filling his bowels. He wondered if this is what it would feel like to have a man shoot hot cum deep inside him. As he began to feel full he felt his cock swelling, also.

Edna noticed the growing dick between her son's smooth legs and smiled. She had never really thought that giving or receiving an enema would turn her on, but she felt a familiar tingling between her legs. She resisted the urge to reach down and wrap her fingers around his now hard cock.

"Mama, it's starting to hurt," Emily gasped as the fluid filled his bowels.

"Just a little more, baby," Edna said as she gently rubbed his lower back and ass. When she saw him raising up on his tiptoes she reached up and closed the valve to stop the flow of water. But she didn't pull the nozzle out of him.

"Now, I want you to clench really hard, and resist the urge to push the water out of you for as long as you can," she said, still rubbing his lower back and ass and upper thighs.

"I can't hold it much longer, Mama," Emily panted. "Please let me empty it out!"

"Just a few seconds more," Edna said. She put her hand on his ass and squeezed his cheeks down around the nozzle. "Just a little more, baby."

Emily was almost crying. "Please, mama! I don't want to spurt it out on you."

"You won't, babygirl," Edna said softly. "I'll tell you when."

"Mmmmm, arrrgggg, oh, mama, I can't wait! Mama! Please!" He was moving, shifting his weight back and forth between his feet, wiggling his ass.

Edna could feel his cheeks trembling. Finally she said, "Okay, I'm going to pull the nozzle out, and I want you to sit down on the toilet before you release. In fact, try to hold it for just a few seconds after you sit down."

As soon as Emily felt the nozzle slide out of his ass he sat down. He clenched hard and managed to hold the water in for just a few seconds before he relaxed and expelled a torrent of fluid from his ass. He sat on the toilet, breathing hard, and realized that he felt empty now, like something was missing.

"Stand up and put your hands on your knees, baby," Edna told him. She patted his ass with toilet paper as she looked at the results of the first rinse, then flushed the toilet. She was happy that the pleasant scent of lavender filled the air above the toilet. She noticed that his dick had started to soften.

"Okay, let's do it again," she told him. "Grab your ankles."

Emily didn't protest. He just bent at the waist and grabbed his ankles again. He looked at his toe nails and noted that they would need to be repainted before he went to see Paul. This time he tensed only slightly when he felt the hard tip of the nozzle against his puckered opening. He moaned just a little when he felt his mother shove the nozzle all the way in.

"It'll be easier this time," Edna said softly as she opened the valve to let the scented water flow.

"Mmmmm," Emily sighed when he felt the warm liquid filling him.

"Does it feel good this time?" Edna asked him. She noticed his dick swelling again.

He nodded. "Yes," he told her.

Edna smiled and nodded and let the water fill him until he started to squirm.

"I'm getting full, mama," Emily gasped.

"I know, baby," she answered. "Just a little more."

Again Emily stood on his tiptoes. Again he shifted his weight back and forth on his feet.

"Is it hurting?" she asked him.

"Not like last time," he answered as he took short, quick breaths.

"Want me to stop?" she asked him. She could see the bag getting slack.

"Yes," he panted.

She reached up and closed the valve, but didn't pull the nozzle out of him.

"This time when I pull the nozzle out I want you to stay like that and hold it in," she told him. "Wait as long as you can before you sit down."

Emily's body shuddered when he felt the nozzle leave his body. He stayed bent over, his fingers gripping his ankles as he clenched his ass cheeks to hold the water in.

"How long?" he asked, his voice barely audible.

"Just a bit more," she said. She moved so that she would be in front of him when she let him sit down. She put her arms around his upper body. "A little more, baby," she cooed.

"Mama? Please?" his voice squeaked.

Edna nodded. "When I tell you to sit down don't push," she told him. "Just let it flow out of you. Now, sit!"

Emily quickly lowered his ass to the toilet. The flow of scented water flowed out of him as from a faucet. He moaned and felt his pucker spasm a few times, as if trying to stop the flow out.

Edna dropped to her knees in front of him. Her plan was to bend over and take his hard cock in her mouth as he expelled the water. She thought he might expel his cum at the same time. Emily put his hands on her shoulders and his body tensed.

But before she could get his mushroom head in her mouth she felt his hot cum hitting her neck and chest. Two hard shots of his cream hit her before she could clamp her lips down over his pulsing head. Three more hard shots of cum filled her mouth before she felt Emily begin to relax.

She sucked gently, letting the last of his cum flow out of his softening dick into her mouth. Emily let his hands slide off of her shoulders. Edna could hear the last of the lavender scented water dripping from his ass into the toilet.

"Whew!" Emily giggled when his mother pulled her mouth away from his crotch. "Did you know that was going to happen?"

Edna laughed. "I thought it might. I wasn't sure. This is the first time I've given an enema."

"So does that mean we are done?" Emily asked.

Edna stood beside him. "Stand up and let me check," she said. She nodded. "Yep, you're all clean," she said when she looked at the clear water in the toilet.

"Now you need to take a bath using one of my bath bombs, and then we'll do our nails and your make-up. Have you decided what you want to wear?"

Emily shook his head. "I'm not sure if I want to go really casual in a sundress or a denim skirt and top, or if I want to wear one of your nicer dresses with some hose and heels."

"Hmmmm," Edna said as she started the warm water running in the tub and threw a small ball of bath bomb in the water. "Since this is a Saturday afternoon thing, and since Paul doesn't really know it's a date yet, I'd say go casual."

Emily nodded. "That's what I was thinking, too. If he wants to ask me out on a date I'll wear the nicer dress and hose and heels for him." He slid into the warm scented water. Edna sat on the side of the big tub, his cum still clinging to her neck and breasts.

"That's my girl!" she smiled. "I say your new coral sundress that looks so good on you without a bra."

Emily nodded. "That's what I was thinking," he smiled.

Emily shaved his underarms and pubic hair and legs while he was in the bath, then stood and used the shower to wash his hair.

He sat naked in the swivel chair in front of his mother's lighted vanity and let her dry and style his long hair. She used her curling iron to give him some body on the top and some curl around the ends.

Then he sat still and let her apply his make-up. He didn't need a foundation since he had no beard to cover. She put coral colored shadow on his eye lids to match the coral colored dress, just a hint of pink on his cheekbones, and coral lipstick on his soft lips.

Edna did a quick touch-up on his finger and toe nails and he was ready to get dressed. She picked out a pair of her best nylon bikini brief panties for him, and helped him pull the dress over his head without mussing his hair.

"How do I look?" Emily asked, as he stepped back from his mother and held his arms out to twirl around. He had chosen a pair of his mother's simple white sandals to wear with the coral dress.

"You are beautiful," Edna said softly. She went to him and hugged him with tears in her eyes. "You are so pretty."

"Thank you, mama," he said, hugging her back. "Thank you for helping me be pretty."

"Are you going to be okay driving to Paul's like this?" Edna asked. "Do you want me to drive you there?"

Emily giggled. "I'll be fine, mama. I was nervous about it before, but now that I'm all dressed and made up I feel better about it. I mean, to anyone looking, I'm just a young woman out going somewhere on a Saturday afternoon, right?"

Edna smiled. "Right," she said. "A very pretty young woman running an errand on a Saturday afternoon."

"And you've talked to Paul and he's expecting you? Does he know you're going to be Emily when you get there?"

Emily shook his head. "I told him I had a surprise for him."

"Well, I think he'll be surprised. I hope it's a pleasant surprise for him," Edna said. She wanted to ask if he was nervous about coming out to Paul like this, but she didn't want to add to any anxiety he might be feeling.

"I think it will be. When I told him I wanted to come over today he asked if I was going to bring something to wear. He seemed pretty excited when I told him yes," Emily said.

Edna watched Emily pack his ID, money and lipstick in the small purse she gave him.

"So, call me if you're going to be really late," Edna said, walking towards the door with Emily. "Or if you decide to spend the night."

Emily stopped before he opened the door. "I will, mama," he said gently. "Try not to worry too much."

Edna laughed. "I can't help it. I'm sending my little girl on her first real date. I so hope you have a lot of fun."

Edna picked up a small pink bag beside the door and held it out to Emily.

"What's this?" Emily asked.

"Your emergency overnight bag," Edna smiled. "Just a few essentials you might need if your date goes really well. A little lesson I learned early in my college career."

Emily cocked his head and looked at her as he took the bag from her.

"A nightgown, some spare panties, enough make-up to do a touch-up, a plain t-shirt and a pair of pull-on pants. I've made the walk-of-shame going home in the same clothes I wore out. It can be embarrassing."

"Thank you, mama," Emily smiled. He kissed her on the cheek and walked out the door.

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Edna watched him walk to his car. She saw him look around furtively and knew he was checking to see if any neighbors were watching. She glanced at the neighbors' houses, too, wondering how she would react if one of them asked her about seeing Josh looking so pretty.

When his car disappeared down the street she walked slowly to the kitchen and poured herself a glass of wine, gulped it down, then poured another and headed for her bedroom. She pulled her sundress over her head and tossed it on the end of the bed. She reached in her camisole drawer to get the vibrating egg.

She sat in the big soft chair beside the bed and looked out over the pool and yard as she sipped her wine and ran the softly vibrating egg lightly over her pubis.

*************************

Emily felt more comfortable when he finally sat down in his car. He was only a little nervous about driving to Paul's house in broad daylight. He'd convinced himself that if was careful and didn't do anything wrong he'd be just fine.

But as he neared Paul's house he began to get nervous about his decision to surprise Paul like this.

What if he was wrong and Paul wouldn't think he was sexy as Emily. What if Paul just wanted to watch the movies and jack off? What if...?

He parked in the drive in front of Paul and his mom's house and took several deep breaths. He wasn't worried about the neighbors here seeing him. He finally opened the door and stepped out of his car.

Paul was watching out the big living room window. He'd seen Josh pull in and park and wondered why he wasn't getting out of his car to come in. Maybe Josh, like Paul, had been thinking about what might happen if Josh came over and put on a dress and looked at least a little like a girl. Maybe Josh, like Paul, wondered if they might go further than jacking off, or even jacking each other off. Maybe Josh, like Paul, was having second thoughts about all those things.

"Oh, my, god!" Paul said aloud when Josh finally stepped out of his car. Paul didn't see Josh in his driveway. He saw a beautiful young woman in a pretty dress walking towards his door. He moved to open the door on shaky legs.

"Josh?" he said as he opened the door to let his pretty friend in.

Emily smiled. "Please call me Emily," he said.

"Yeah, okay. Emily," Paul said, still staring as he closed and locked the door. "Um, do you want something to drink?"

"Yes, please," Emily said. "Do you have any white wine?"

"Um, yeah, I think we do." Paul turned and went to the kitchen. When he returned with a glass of wine and a drink for himself he looked closely at Emily- the make-up and hair, the painted nails, the cute dress.

"So, what do you think?" Emily asked, laughing.

"Um, I think you're... you're beautiful!" Paul said. "So, I knew you liked to play dress up in your mom's clothes, but I never imagined you would do the whole make up and nail polish thing."

"Thank you," Emily blushed. "Um, my mom helped me... a lot."

"She helped you? So you finally told her you like to dress up?" Paul asked.

Emily laughed. "She already knew. The other day when we were playing disc golf she was shopping for a new dress to wear to my cousin's wedding. While she was at the mall she saw this dress and thought I would like it so she bought it for me."

"She just bought you a dress?"

Emily nodded. "She bought me this one and two others. So we talked... a lot... and now she wants to help me be Emily when I want to."

"So, had you already talked to her about, um, Emily?" Paul asked. "I thought you hid your dressing from her?"

"I did. But she just knew. Moms know things like that. Your mom probably knows you want her to put you on a leash," Emily laughed.

"I doubt that," Paul laughed with him.

Emily thought about telling Paul about everything else that had happened, but decided to wait on that for a bit.

"That is so cool," Paul said. "And, um, she knew you were coming to see me today?"

Emily laughed. "Yes, she knows where I am. So don't you even think about kidnapping me!"

Paul laughed. "I won't. Um, hey, why don't you go ahead and have a seat and watch the movie you wanted to see. It's in the dvd player. You know how to turn it all on."

"And what are you going to do?" Emily asked.

"Um, I'm going to run upstairs and take a quick shower and put some different clothes on," Paul told him.

Emily stepped closer to Paul to put his hand on Paul's arm. "You don't have to do that," he said, letting his hand slide down Paul's arm so that they were holding hands.

"Yes, I do," Paul said, squeezing Emily's hand. "Really, you look and smell so great. I'd just be a lot more comfortable if I go clean up some."

"You think I smell good, too?" Emily asked.

Paul blushed. "I think you smell pretty," he said.

"Well, you don't have to smell pretty," Emily smiled. "I'm the pretty one here."

"Yeah, but..." he pulled his hand out of Emily's grasp. "I'll be right back. 10 minutes. Sit down and turn on the movie. The wine is sitting on the counter in the kitchen if you want more. I'll be right back."

Emily laughed but let him go. He kicked off the sandals and sat on his feet like he'd seen so many women do.

He reached for the controls and soon the big screen was showing a man who was dressed in women's clothes, but with no make-up or wig, and a woman who was supposed to be his wife telling him that she was going to invite some of her male friends over and teach him how to be the woman he wanted to be. Emily's cock tingled and swelled at the thought of having a wife who would do that to/for him.

Paul almost ran up the stairs. Josh showing up as Emily changed his plans. He had planned to let the movies do their magic and get them both horny, then if it looked like things were going to move past just jacking off he'd suggest they go take a shower together. Since Josh called and said he was coming over Paul had jacked off several times thinking about being in the warm shower with his friend, with them rubbing their naked soapy bodies together.

'That could still happen,' he thought as he stripped and got in the shower. He had to resist the urge to stroke his soapy cock as he thought about the pretty girl waiting downstairs. The pretty girl he was pretty sure wanted to have sex with him.

Emily drained his glass and went to the kitchen area for more wine. He felt so sexy walking around Paul's house barefoot and in his pretty dress. His cock was semi-hard in his panties, but the full skirt of the dress hid that from view. He had butterflies in his stomach as he thought about what he wanted to do... what he intended to do when Paul joined him in the living room.

When Paul came back down the stairs he turned toward the kitchen to refill his glass. He looked at Emily. "More wine?"

Emily smiled and held his nearly full glass up for Paul to see. "I'm good," he said.

Paul mixed his drink and came back in the living room. He sat on the couch, but not right beside Emily. Emily was sitting so ladylike with his feet tucked under him! Paul stared at the tv screen where the man wearing a dress and garter and stockings, but no wig or make-up, was on his knees surrounded by five naked men with hard cocks. His own cock immediately began to grow. He put a hand on his crotch and rubbed himself lightly.

He looked out of the corner of his eye to see how or if Emily reacted to him rubbing his crotch. He wasn't sure what he expected him to do. The original plan had been for Josh to come over and they would watch the xxx movies and jack off together, and maybe even jack each other like they had a few times this summer. He didn't know why he thought Emily might be offended by him rubbing his dick, but he did think that.

Emily saw Paul sit down and almost immediately put a hand on his crotch. He could see the bulge in Paul's shorts and knew his friend was getting hard. He wished Paul had sat down closer to him. But he didn't.

So Emily decided to move closer to Paul. He scooted over on the couch until his body was touching Paul's arm. He lay his head down on Paul's shoulder and put his hand over Paul's hand, rubbing Paul's dick with him.