Josh's Journey

He sat on the bed with the panties in his hand. Before he put them on he raised them to his face and inhaled his mother's musky scent. He felt a stirring in his young cock as he put his feet into the panties and pulled them up so that the soft nylon material caressed his cock and balls and ass. He always got a thrill knowing that the crotch of her panties, the part that had been pressed against her pussy all day, was now nestled against his own cock and balls.

He put on a pair of loose cotton gym shorts and a loose tank top, his standard wear around the house, especially in the evening when it was just him and his mom there. He felt like it was the most feminine thing he could wear without being too obvious to his mom.

He went back out on the patio to get the pitcher and glasses they'd left there earlier. His glass was still half full, so he sat down in the chair and watched the water in the pool shimmer in the moonlight while he sipped on it.

He thought about what had happened earlier. He tried to remember every detail of how it felt to rub his fingers on his mom's pussy, how she had ground her ass down on his cock, how she had stood, her body shaking as the strong orgasm shot through her body.

He wanted her now more than ever. He'd lusted after his mother for a while, sniffing her panties and hose and even her shoes while he jacked off. He'd found excuses to walk into her room when he knew she was changing, hoping to get a glimpse of her body, but satisfied just seeing her in her lingerie... even her white cotton bras and panties.

But he'd actually made her have an orgasm. And even though she hadn't known it, he'd had an orgasm with her. He remembered that he could smell her strong musk when he was rubbing her pussy. He could feel how wet the crotch of her swimsuit got as her orgasm started. Now he wanted to sniff and lick her pussy. He wanted to lick the backs of her thighs up to the crease of her ass cheeks. He wanted to spread her ass cheeks and lick her musty ass.

He felt his dick getting hard in the panties. He was absentmindedly rubbing on the bulge in his shorts when he heard the sliding door open. He jerked his hand away from his crotch, but looked down and saw that the bulge was very noticeable. Well, it was dark. Maybe she wouldn't notice.

"You're still out here," Edna said as she came out to the patio. "I guess I dozed for just a little bit," she laughed.

Josh looked up at her. She still had the swimsuit on, but she'd added a short cover-up. She seemed to think he'd been outside the whole time, and Josh didn't see a reason to tell her the truth. He wondered how much she remembered from earlier.

"Yeah," Josh laughed. "I think you did. Feel better now?"

She sat on the edge of the chaise lounge. She picked up her empty glass, looked at it, and then sat it back down. "Yeah, I do. I guess I sucked the wine down a little too fast and it hit me," she laughed.

"I think so," Josh said. "Are you hungry? Do I need to get you something to eat?" he asked.

She reached for her glass again, and poured it half full of the Sangria.

"No, I'm fine. How about you? Did you get something to eat while I napped?" she asked.

"Yeah, I'm good."

She took a sip of her drink, then looked at him.

"Um, Josh, um, I'm sorry about before," she said quietly.

"Mom, don't," he said quickly. "You have nothing to be sorry for. It happened. I enjoyed it, too."

"I know, but, well..."

"Mom, stop." Mark said firmly. "It happened." He took a big gulp of his drink. "And be honest... didn't it feel good?"

"Well, of course it felt good," she said. "But it's just not right."

"I know, I know," he said. "The rules. Well, like I said before, I don't like the rules. There's a lot of rules I don't like right now."

"Oh?" Edna asked. "Is there something I can help with?"

Josh snorted. "No. You want to follow the rules."

Edna shook her head. "I don't like the rules, either," she said quietly. She took one more sip of her drink before she stood and walked back into the house.

Josh poured the last of the Sangria into his glass and sat in the dim light sipping it, wondering how or if he would ever find a way to tell his mother everything.

As he gathered the empty pitcher and the empty glasses it suddenly dawned on him- she doesn't like the rules, either! She just said so!

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

"You're up and around early for a Saturday morning," Edna said when Josh came into the kitchen/dining area. "Coffee?"

"Please," he said as he sat down at the breakfast bar across from where his mother was sitting. He watched her turn to the counter to pour him a cup of coffee. She was no longer wearing the swimsuit. She now wore an outfit very similar to what he had put on last night- soft cotton gym shorts and a loose tank top.

Josh could tell she didn't have a bra on, and Edna noticed him looking at her chest as she leaned over the breakfast bar to hand him his coffee. He loved how her breasts swayed when she moved, and how her nipples, even soft, pushed against the thin material of the tank top. She smiled and blushed but didn't say anything.

Josh wondered if she'd looked for her panties from yesterday, and what she'd say if she knew he was still wearing them.

"So, what gets you up and around so early?" she asked as she sat back down with her coffee.

"Paul and I are going to play some disc golf this morning," he answered. "We like to get there fairly early before it gets too crowded."

Edna nodded. "Um, hmm," she said.

"What about you?" Josh asked. "You got big plans for the day?"

She shook her head. "I'm going to be a little lazy this morning. After my shower I'm going to go to the mall. I need a new dress for your cousin's wedding. Do you want me to wait until you get home so you can go with me?"

In his younger days Josh loved going shopping with his mom. He could act like he was looking for something for her, but actually he was looking at things he wished he could buy for himself.

"No, mom, you go ahead without me this time. I'm not sure how long I'll be."

"Okay, honey, if you're sure. I don't mind waiting for you if you want me to."

Josh wanted her to stop offering to wait... because he wanted to tell her to please wait! Or he wanted to call his friend and make an excuse to not meet him and go dress shopping with his mother. Actually he wanted to call his friend and tell him he wouldn't make it BECAUSE he was going dress shopping with his mother. But he knew he couldn't do that.

He gulped down his coffee and hurried out the door before he changed his mind.

Edna looked at him as he drank the coffee and smiled at her. She thought what a cute boy he was... no, a handsome young man. He was a young man now, almost twenty-one, a college student. But when she thought about it, he wasn't handsome. He was cute.

His shoulder-length hair that was the same color as hers used to be, his slender, delicate face, his small hands and feet... and he even had a cute ass for a man! He was definitely cute.

She knew he'd dabbled in playing dress-up in her clothes when he was younger. She suspected he sometimes still did. She'd never said anything because, well, what was it really hurting? When her husband was still alive he'd gotten mad about it when they caught him. He didn't want his son playing dress-up in his wife's clothes! But Edna had kept him from saying anything to the boy.

"It's just a phase," she told her husband. "He'll grow out of it. A lot of boys do it." And to make sure to get his mind off of Josh's dress-up games, she put one arm around his neck and the other hand on his crotch. "Come on, show me what a man does when he grows up!" And it worked every time.

Then Edna thought about last night. Her memory of it was a little hazy, but she remembered enough. Josh had known just where and how to rub her! She wondered where he learned that. He didn't date that often. But when he'd kissed her neck while he circled his fingers around her swollen clit she was quickly lost in her own lust.

Yes, she'd told him it was against the rules. Yes, she'd told him they should not, could not do that again. But she could tell he wanted to. And if she was honest with herself she knew she wanted it to happen again, too.

He had openly said he didn't like the rules. She didn't like them, either. But she couldn't say that. Except that she did. Last night. Was it really so bad, though? In her own mind she was thinking that maybe it wasn't.

After all, he had just touched her outside of her clothes. If he'd shoved his fingers into her swimsuit and put a couple of them in her pussy that would be different. But he didn't. He didn't even try. He just rubbed on the outside of her swimsuit. So what if where he rubbed happened to be directly over her sensitive clit. It was still on the outside of her suit.

Edna realized that she was absentmindedly rubbing her own fingers along the seam of her gym shorts as she had all these thoughts. She shook her head to clear it and got up to get herself another cup of coffee.

She took her coffee cup to the bedroom to start getting ready for her shower. When she took her shorts and panties off she noticed that the crotch of the panties was wet, and a wet spot was visible along the seam of the shorts.

"Why am I so horny?" she asked aloud. Without taking the tank top off she opened her bra/camisole drawer. She reached in the back and pulled out the hard plastic vibrator. She twisted the end of it to make sure it had good batteries, then lay down on the bed.

The vibrator was a long, thin handle, slightly curved at the end, with a vibrating egg on the end. It was hot pink, which was the reason she'd bought it. She'd never had a sex toy before she bought the 'egg', as she called it, so she figured a pink one was designed for a woman.

She lay on her back, her feet flat on the bed and spread apart. She let her knees fall to the sides. She twisted the end of the egg again and moaned as she ran it lightly over her swollen clit. She used one hand to run the vibrating egg over her clit, her lips, even down around her pucker while with her other hand she pushed her tank top up enough to get a hand on her bare tit.

She slowly moved the egg up and down her slit, moaning and pushing her hips up to meet it. "OH!" she yipped when she pushed the egg inside her wet pussy. "Ohhhh, yessss!" she moaned when she worked it in and out. She pulled the egg back out and moved it in circles around her swollen clit. She pinched her right nipple hard as she pushed the egg harder and harder against her clit.

Her hips were undulating rhythmically, matching the motion of the egg on her pussy. A series of mews and yips escaped her lips. She knew it wouldn't take long.

Suddenly it hit her. Her legs stiffened, lifting her ass off of the bed. The fingers pinched her nipple even harder. She moved the vibrating egg around in circles on her clit. When the first wave of the orgasm hit her she shoved the egg back inside her pussy. She could feel her inner muscles spasm around the egg as wave after wave of orgasm washed over her.

Finally she let out the breath she'd been holding since it started. She released the grip on her nipple and let her hand slide off of her tit. Her legs relaxed and let her ass settle back down on the bed.

She was still very slightly moving the vibrating egg inside her pussy. Her hips were still jerking just a little. She twisted the end of the handle on the egg so it would stop vibrating, but left it inside her. She relaxed, her chest heaving as she regained her normal breathing.

She absentmindedly pulled at the hair on her pubis and wondered if she should trim it while she was in the shower. She relaxed just a moment, then pulled the egg out of her pussy, wiped it down with the panties she'd just taken off, and put it back in the drawer.

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

Josh walked around the disc golf course with his best friend Paul. They'd been best friends since elementary school. They were both considered 'nerds' in junior high and high school... but a lot of the popular guys and girls came to them for help with their homework.

Now they were both in college, and still considered nerds. It just wasn't as noticeable on the bigger college campus. This summer they were both taking extra classes at the local community college to get ahead in their degree programs.

Josh and Paul talked about everything. They had discovered masturbation together. Paul knew about Josh's penchant for wearing his mother's clothes. When Paul was younger he tried to wear his mother's clothes, but she was a very big woman, so nothing of hers would fit him. Even now that he was as grown as he was likely to get, her clothes still dwarfed him.

"You ever think about eating your mom's pussy?" Josh asked as they walked.

Paul stopped and looked at him "Whoa, dude, where'd that come from? Did something happen with your mom?"

"No. I just wondered. I do." Josh said. He wanted to tell Paul what had happened, but he was afraid his friend would think it too weird.

Paul nodded. "Yeah, I've thought about it. Especially when I sniff her panties to jack off."

Josh laughed. "Yeah, me, too. Especially then."

They walked in silence for a bit.

"But if you had the chance, you'd do it?" Josh asked.

Paul thought about it for a moment. "I think so. Maybe. I mean, I like the way her panties smell, but sometimes the smell is a little strong, so, the real thing... I'm not sure. Being big like she is, you know?"

Josh nodded. "Yeah, that makes sense. I think my mom smells really good," he said.

Paul nodded. "I'll be she does. I'd eat your mom. Hope it's okay for me to say that."

Josh laughed. "It's okay. I'm pretty sure I'd eat your mom, too. Even with the strong smell."

They tossed their discs at the next target, then started walking to them for the next throw.

"Do you still wear your mom's panties and things when she's not home?" Paul asked.

"Yeah," Josh said, blushing. Even though he'd told Paul about it a long time ago, he was still a little embarrassed to admit he liked to dress up and pretend to be a girl.

They walked in silence for a while.

"How does it make you feel to dress up in your mom's things?" Paul asked.

Josh blushed again. "I don't know. I like how it feels."

"Do you feel pretty?" Paul asked.

Josh blushed some more. "Yeah, actually I do. I think I look a lot like my mom, and I think she's really pretty."

Paul looked at his friend as they walked. "Yeah, you do. I'll bet you are."

Again they walked in silence for a while.

"I'd like to see it sometime," Paul said.

"What?" Josh asked, not sure what 'it' meant.

"How you look dressed up," he said.

"Oh. Um, ok. Sometime. Maybe." The thought of dressing up for Paul excited Josh. No one had ever seen him dressed up except for the few times his parents had caught him when he was younger. To actually pretend to be a girl around one of his friends would be a thrill.

They talked about other things through the next few holes of disc golf.

"Do you ever snoop around in your mom's closet and drawers?" Paul asked.

Josh laughed. "Yeah. I like looking through her drawers to see what all she has. I found a vibrator a few weeks ago. I'm not sure if it's new or if I just hadn't found it before."

Paul laughed. "Yeah, my mom has several vibrators, and even a few dildos. One of the dildos is really big. And black. It looks like a real dick."

"No shit?" Josh asked. "Your mom has a big black dick? Do you think she fucks herself with it?"

"What else would she do with it?" Paul asked.

"Well, I don't know. I just have a hard time picturing your mom shoving a big black dick I her pussy," Josh said.

"Me, too, at first," Paul said. "But after I found her dirty movies I'm not so sure. One of them is a movie of black guys with huge dicks fucking white women. A lot of the women are big, like my mom."

"Your mom has dirty movies?" Josh asked.

"Oh, yeah, several," Paul said. "In fact, there's one you might like. It's about women who dress their men up like sluts and make them suck other men, or bend over and get fucked by other men."

"Wow. Yeah, I'd like to see that one," Josh said. "It sounds hot. Have you watched it?"

"I've watched some of it, just to see what it was. Not really my cup of tea. But you can come over and watch it sometime if you want to. Would you do that?"

"What, let a woman dress me up and make me suck dick?" Josh asked. "Um, maybe."

"So which one is your cup of tea?" Josh asked. "The one with the black guys fucking white women?"

"Nah. I like that one, too. But there's one that gets me going every time," Paul said. He hesitated and blushed. "It's about older women who make younger men do things to satisfy them."

Josh looked at him. "What kind of things? Weird things?"

Paul laughed. "Well, not so much weird things. Well, not too weird. Like, there's this one where a fat woman has a guy on a leash, and she leads him around and makes him eat her ass and pussy and lick her feet... stuff like that. In front of other people."

"Wow. That sounds kind of hot, too," Josh said.

"It is," Paul told him. "And, uh, the one with the fat woman and the guy on a leash... well, except for her face, it could be my mom. When I watch it I, um, well, I pretend it is my mom, and, um, that I'm, um, the guy on the leash."

Josh smiled. "Damn, friend, I didn't know you're so kinky!"

Paul laughed "Me, kinky? You're the one who wants a woman to dress you up and make you suck dicks and bend over to get fucked!"

Josh laughed and nodded. "True."

They had finished the disc golf game and were back at their cars.

"Uh, listen," Paul said. "My mom is going to be gone next weekend. She's leaving Saturday morning to go visit her sister and won't be home until Sunday."

"Good to know," Josh said. "Is that an invite to some over and watch some movies?"

Paul nodded. "If you want to. And, uh, if you wanted to bring something to wear, um, you know..."

Josh nodded. "I'll think about it."

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

Edna walked through the mall, mostly window shopping. She wished Josh had wanted to come with her. She loved to bring him shopping when he was younger. She loved the look on his face as they looked through the pretty clothes to find something for Edna. She knew he was really shopping for himself. She wished that she had bought something just for him back then.

She found the dress she wanted for the wedding quickly. In the first store, actually. She saw it and just knew it was the one. She wished Josh was there to tell her it was the one. He was always so good about telling her how she looked. Sometimes he'd tell her a dress was too frumpy, too old for her. And she'd remind him that she was old. And he'd smile and tell her she wasn't, and that she shouldn't dress like a grandma. She loved those times with him. It was almost like having a daughter to shop with.

But she was at the mall, so she shopped some more.

She found herself looking at cute sundresses. At a particular style of sundress. They were above the knee length, some shorter than others, had one-inch wide straps over the shoulders, and had a gathered elastic bodice. She found one she loved and tried it on.

It was a light coral color, almost pink. The straps over the shoulder were ruffled. The bodice was elastic and fit tight on her chest, and went down to her waist where the skirt then flared out to a full skirt that only reached to mid-thigh. Edna tried it on and twirled around in front of the mirror. She loved how it felt. It made her feel young and girly.

But as she twirled around and looked up at the tri-fold mirror it wasn't her in the dress... it was Josh! And he was cute.

She bought the dress and two others. She bought them for Josh. She wondered why she hadn't done it before. She wondered why she felt a tingle between her legs when she bought dresses for her son.