Josh's Journey

Warning! While I put this story in the Transgender and Crossdresser section, there are strong elements of Incest/Taboo included. If the combination of crossdressing and incest offends you, please stop reading now!

"Hey, mom, I'm home," Josh Grant called as he walked into the house.

"In here, honey." His mom Edna's voice came from the direction of the kitchen.

Josh dropped his backpack on the dining room table as he walked by it on his way to the open kitchen. He stopped to admire his mom. She was wearing a one-piece swimsuit and standing on a short step-stool trying to reach a plastic pitcher on the top shelf of the cabinet.

He loved how the one-piece suit hugged her body and enhanced her figure, how it squeezed in at her waist and flared out to accentuate her wide ass. He loved how when she reached up the bottom pulled up to let a peek of her white ass cheeks show.

Josh walked behind and put his arms around her to steady her. He pressed his chest and face against her back and slightly rubbed her belly.

"Mom, you know you shouldn't be doing that when I'm not here," he told her. "What if you fell?"

"You mean like this?" she laughed as she leaned back and let him hold her up.

Josh laughed, too. As he set her down he let his hands slide up her front side and brush ever so discreetly against mom's chest.

"Yes, like that," he said. "You could hurt yourself. I wouldn't like that."

She pushed a hand against his chest. "Oh, you," she laughed again. "How do you think I got things from the high shelves before you were old enough to keep me from falling?"

"Hush," he said. "I don't need you being all rational on me. So what do you need the pitcher for?"

She turned back to the counter. "I thought I'd mix up a pitcher of Sangria," she said.

"Oh? You haven't done that in a while. What's the occasion?" he asked.

"Nothing, really. It's Friday. The weather is bearable outside. I thought it would be nice to sit out by the pool. You're welcome to join me if you don't have big plans for the evening."

Josh shook his head. "No plans for me," he said.

She looked over her shoulder and smiled at her college sophomore aged son. "Then why don't you go put on a suit, or at least some different shorts. I'll meet you out there," she said as she poured the ingredients for the Sangria into the pitcher."

Josh reached out and popped her on her soft cheek. He loved how her ass jiggled when he slapped it.

"Be right there," he laughed as she turned to swat at him.

Josh went to his room and stripped out of the clothes he'd worn to class. He could see his 46 year old mother on the patio next to the big in-ground pool. He knew she'd never wear that swimsuit in front of company. Even in front of Josh she usually wore a cover-up until she was ready to lay down on the big chaise lounge to work on her tan.

He absentmindedly fondled his cock as he looked at her though the gauzy curtains. He knew that even if she looked at his window she would only see a shadowy figure. She wouldn't be able to tell he was playing with himself while he ogled her.

The suit was a light tan color, even lighter than the parts of her skin that were tanned. From a distance it appeared that she was nude. It was more like a gymnast's leotard than a swimsuit. The wide straps held the front of the suit in place. There were no built-in cups like in her other swimsuits, so her b-cup tits were held tight against her chest and her big nipples were clearly visible, especially if she got in the cold water. If she raised her arm or moved just right the side of her tit was visible.

At the bottom of the wide piece of spandex that covered her belly was a bikini bottom that barely covered her ass and pussy. The leg openings were high on her hips. The small strip of fabric that ran between her legs was just wide enough to pull into the crease between her puffy lips and her thighs, and the back of the bottom fully covered her ass cheeks only when she pulled them down to the crease between her round cheeks and the backs of her thighs.

Josh couldn't see the curly brown hairs on each side of the strip of fabric covering her pussy, but he knew they were there. He had never known her to shave or even trim her curly pubic hair. If they were to have company for the pool, or go to a party at someone else's pool, Edna would wear one of her more full-coverage swimsuits with a skirt that reached several inches down her thighs and made a bikini trim unnecessary.

Josh enjoyed the inadvertent show she put on for him as she set the pitcher and two glasses on a table, then spread her big beach towel on the chaise lounge, then pulled the back of the chaise up so that she would be in a sitting position instead of laying down.

When she bent over the suit pulled more into her ass crack, exposing more of her cheeks and accentuating her soft, round butt. Sometimes her boobs drooped very near the side of the suit and Josh watched closely for a glimpse of nipple.

When she finally settled down on the chaise and poured herself a glass of the chilled mixture from the pitcher Josh shook his head to bring him back to reality. His hand was still on his dick, and his dick was fully hard. He wondered if he should jack it off real quick, but decided not to. He sighed and opened his drawer to get one of his swimsuits.

He wanted to pull out the two-piece women's suit he'd ordered online a few weeks ago. He'd tried it on and worn it around the house when he was home alone and he loved how it fit and how it looked on him.

The top was like a bralette with spaghetti straps. The thin piece of lycra material across his chest hugged his body and allowed his small nipples to show. The top had a piece of elastic that ran across the bottom, just under his tits, and up the sides of them to push them up and towards the middle to create a little bit of cleavage. It was like a training bra made into a swimsuit top.

The bottom was a simple bikini with an attached skirt that barely covered his ass cheeks, but effectively hid his bulge. With is long hair pulled slightly over his face he looked a lot like a flat-chested girl in a conservative swim suit.

But his mom didn't know he had the suit. He was pretty sure she was aware that he sometimes tried on some of her clothes, including her swimsuits, when he was home alone. But he'd never worn anything in front of her, and they'd never talked about it, so he wasn't sure how she'd feel if he wore his new suit to join her for refreshments by the pool.

Maybe they could have a few glasses of Sangria and he could relax enough to bring it up. Maybe she'd tell him to go in and put it on and show her how he looks in it. Maybe she'd tell him he looks cute and should always wear it when it was just the two of them at the pool. Maybe she'd tell him to wear whatever he wanted around the house. Maybe, maybe, maybe.....

But he pulled out one of his men's suits and pulled it up his legs. He liked that the lining in the suit didn't hug his body like his briefs, so it felt almost like going commando. He could feel his still semi-hard cock moving in the loose suit when he walked and wondered if his mom would notice it.

He knew he was wrong to hope that she did, and even more wrong to dream that she would want to touch it. But he was a 20 year old man/child full of hormones. He got a hard-on looking at the women's underwear ads in the Sunday newspaper.

Josh felt almost self-conscious when he saw his mom looking at him as he walked out and sat in the chair next to her. He was sure she was eyeing the front of his suit. She had to have noticed his cock moving and swaying under the soft material of his swimsuit.

Edna poured her son a glass of the potent wine mixture, then refilled her own glass and sat back in the chaise.

"I so enjoy sitting out here and enjoying the sun on my skin when the weather is like this," she said.

"Yes, it does feel good," Josh agreed with her. He admired her legs and her pretty feet with her painted toe nails. He saw the sun glinting off of the stubble of dark hair on her calves and smiled. He loved that she wasn't fastidious about shaving if she wasn't going to be in a situation for others to see it. He wondered if her armpits were stubbly, too, and wished she would lay back and put her arms over her head.

They made small talk about Josh's school, about Edna's part-time job, about friends. Edna drained her second glass of Sangria.

"You need some more wine?" she asked Josh as she reached for the pitcher.

"I'm good, mom," he said. "You got a head start on me."

"That I did," Edna giggled. "And, I need to pee!" She set her glass on the small table beside her chaise lounge and started trying to stand up.

She was a little light-headed from the wine, and swayed just a bit when she stood. Josh reached out and put his hand on her ass to steady her.

"You ok, mom?" he laughed.

She slapped at his hand. "I'm fine. You just wanted an excuse to feel of my butt!" she giggled.

Josh moved his hand. But she was right. He watched her walk to the sliding doors and go in the house. He took the opportunity to adjust his still semi-hard dick in his loose fitting swim trunks.

"Whew, I feel better!" Edna announced when she came back out the sliding doors.

Josh watched her tits bounce as she walked back to the chaise lounge. She saw him looking and bounced a little when she was in front of him. "You like that?" she giggled. Josh could tell the wine was starting to affect her. He'd seen her this way before.

He smiled. "What's not to like?" he asked.

"Oh, I can't believe you like looking at a fat old woman's saggy boobs bouncing," she said as he turned to sit back down on the chaise lounge.

"You're neither fat nor old," Josh told her as he looked at her ass in the high cut swim suit. She'd pulled the legs back down over her cheeks, but he could still see the edge of her cheeks.

Edna leaned over to move the cushion on the chaise before she sat down. When she stood back up she swooned, as if she might fall. Josh instinctively reached up to steady her, and instead of falling she sat down... in Josh's lap.

Josh quickly set his drink on the table and helped her sit without falling. His arms were around her waist, his hands on her belly. When she sat down her legs were on the outside of Josh's legs, so her thighs were spread apart. Josh's hands fell naturally on the tops of her thighs. Edna leaned back against him.

"Oopsie!" she giggled. "I'm sorry, baby! I hope I didn't hurt you." She wiggled her ass to show that she meant she hoped she didn't hurt his cock and balls.

Josh started to lightly caress the tops of her thighs. "You didn't hurt me, mom," he said.

Josh moved his hands down to the insides of her thighs, still gently caressing her, moving up until he could feel the hair peeking out the sides of her swimsuit. Edna moaned lightly and spread her legs a little more.

Josh moved the fingers of both hands until they were over the thin strip of lycra covering his mom's puffy lips. Edna moaned again.

"No, Josh, you can't do that," she said, her voice raspy. She grabbed his hands, but didn't really pull them away from that thin strip of fabric.

"Why not, mom?" he asked. "Doesn't it feel good?" He rubbed harder at the top of her slit where he knew her clit would be. Edna's hips jerked, and an 'Oh!" came from her mouth.

"Oh, yes, baby, it feels good," she said, her hands still over his. "That's why you... we shouldn't do it."

Josh nuzzled the back of his mother's neck. He knew some of the girls his age liked it when he did that to them, so he figured his mom would, too.

"I like to make you feel good," he said softly as he kissed her neck and ear and moved his fingers in a circular motion around her clit.

Josh had dreamed of doing something like this for a long time. Most of the scenarios he imagined involved him putting tanning lotion on her back and slowly moving his hand between her legs, or waking up behind her to hug her and pulling her back against him as he kissed her neck and caressed her tits, or...

"Josh, no," she said. But she spread her legs wider, and moved her hands up to her tits. Her hips were undulating. She was pinching her nipples. She didn't know why she was allowing it to continue, other than that it felt really good to have another person touch her. She hadn't been touched by a man for over five years, since Josh's dad died.

She lay her head back on his shoulder and closed her eyes, soft moans escaping her lips.

Josh moved in his seat, trying to adjust his now hard cock in his loose trunks. He managed to get it laying against his belly so that when she moved and he moved it was like he was humping her.

Edna pushed her ass back against her son's hard shaft. She liked the feeling of it between her cheeks, pressing the fabric of her swimsuit hard against her puckered back hole. Her hips were jerking sharply whenever his fingers found her swollen clit.

'Just a little more,' she thought as she concentrated on the feeling between her legs. She was so horny! She needed to cum so bad! She was almost there! Those magic fingers on her clit, the hard shaft rubbing between her cheeks like when she was younger and wouldn't have intercourse with the boys, but she let them hump her ass just to keep them satisfied. "Just a little more!" she said aloud.

Edna sat up, then stood up, suddenly. 'A little more?' she thought to herself! 'No, no, no!' That was her son! She stood up to get away from his rubbing fingers.

But it was too late. The first wave of the orgasm swept through her as she stood up. She bent over and pressed the heel of her hand hard against her pubis, trying to stop the next wave. But it was impossible. She squeezed her thighs together. Her hips jerked. Without even thinking she put two fingers on the now wet fabric over her clit and rubbed it.

Josh groaned when his mom stood up so suddenly. He was almost there! He had been humping his cock against her ass while he rubbed her clit. He grabbed his throbbing cock, his hand on the outside of his swimsuit. He squeezed and jacked and moaned when the first spurt of his cum exploded out of his mushroom head. He jacked his hand up and down as shot after shot of cum filled his swim trunks.

Finally Edna's orgasm started to ease up. She was still bent over, her hands on her knees, gasping for breath.

The last of Josh's cum oozed out of his swollen head. He pushed his fingers under the waist band of his swimsuit and got some of his cum on his fingers, then licked it off.

He wasn't sure if his mom was just breathing hard or if she was trying to not cry. He reached up and put his hands on her hips to pull her back down in his lap. She didn't resist, but she didn't lean back on him this time. She perched on his lower thighs with her legs together.

Josh grabbed her glass from the table and reached around her. She took it and took a big drink of the strong wine mixture. Josh picked up his own glass and took a big drink, then took a deep breath. Now it was awkward.

"Josh, I'm so sorry," Edna said quietly.

"You don't have anything to be sorry for," he told her gently.

"I'm embarrassed. No, I'm ashamed of myself." She drained the last of her drink and set the empty glass on the table beside them. She stayed sitting there because she didn't want to face her son.

"Why, mom? You didn't do anything to be ashamed of." Josh picked up her empty glass and poured some more of the strong mixture into it.

She snorted/laughed. "Yeah, right. I just sat here and let my 20 year old son Jill me off like a common tramp!" She took the glass from him and took another big drink.

"You're not a tramp," he told her. "Um, mom, can I ask you a question?"

Edna sighed. "Sure, baby," she said.

"Um, mom, did you.... um, did I make you... um, you know... have a, um..."

"Yes, honey, I had an orgasm," she said quietly. "You gave me an orgasm. A really good orgasm." She took another big swig of her drink.

Josh took a deep breath. "I've never done that before," he said quietly.

"Well, you did good for your first time," she laughed. "I guess I should offer to do something for you. Do you need me to take care of you?" She reached behind her and put her hand on the crotch of his swim trunks. They felt damp. She wondered if she had leaked her juices on him while he rubbed her clit.

"Uh, no, mom," he said quickly. "Um, when you were sitting back on me and moving around, um, well, it felt really good."

She nodded. "Okay. Good. I'm not sure I could break any more of the rules tonight."

"What rules, mom?"

"The rules that say moms don't have sex with their sons, and sons don't have sex with their moms," Edna said.

"I don't think I like those rules," Josh said. He was feeling the strong wine mixture. He started rubbing his hands up and down his mom's back, especially on the bare skin near the edge.

"Well, right now I don't either, but we can't change them," she said. She drained the strong wine mixture in her glass. "I think I'm going to go in and lay down," she said. She stood on wobbly legs.

"Are you okay, mom?" Josh asked. He reached out to put a hand on her hip to steady her. "Do I need to help you get in?"

Edna pushed her son's hand away. "No, I think I can make it to my bed on my own."

But when she stumbled again Josh stood and put his hands on her arms to steady her. "Let me help you, mom," he said gently.

Edna nodded and wrapped her arms around his arm and let him walk her to her bedroom. As she sat on the bed and turned to lay on her stomach she looked up at him.

"Lay behind me and rub my back, please, Josh?" she said softly. "I just need to feel loved. Please?"

Josh walked around the bed and lay down behind her. He put one leg against hers and started to rub the palm of his hand lightly on the bare skin of her back. He wanted to push his hand inside the bottom of the swim suit to rub and squeeze her soft ass cheeks, but thought better of it.

He felt his dick start to harden again as his mind wandered to all the sexy things that could happen if he put his hand inside his mom's swimsuit and she liked it. He lay his head on the pillow and closed his eyes as he softly rubbed his mom's back.

Josh forced his eyes open and tried to look around without moving, trying to remember where he was, and why. It came back to him slowly.

He was in his mother's bed... or rather, on it. He'd dozed off while he laid behind her and rubbed her back. Now he was on his back, and his mom's head was on his shoulder. They were covered in a comforter. Josh wondered who got it, him or his mother, and when.

She was snuggled into his side, one arm over his chest, one leg draped over his legs, breathing rhythmically, almost snoring. Josh closed his eyes and enjoyed the feeling of her body against his. They were both still wearing the swimsuits. He looked up at the window and saw that it was dark. He wondered what time it was.

As Josh tried to slowly, quietly ease out of the bed he noticed that as she had twisted around in the bed one of her tits had slipped free of her swimsuit and was in full view. He couldn't help himself. When he was out from under her arm and leg and she was still snoring lightly he reached out and cupped the soft orb. He'd brushed his hands against her tits many times over the years, but this was the first time he openly groped one. He squeezed just a little, and rubbed her hard nipple, until she moaned and started to move. He pulled his hand back and quickly left the room... but not before he grabbed the panties she had left on top of her shorts when she changed into her swimsuit.

Back in his own room Josh stripped off his swimsuit and tossed it in the hamper to be washed. The soft inner liner was stiff and crusty with his dried cum. He went into his own bathroom and used a damp washcloth to wipe away most of the cum that was dried on his lower belly, pubis and thighs.