Josh's Journey Ch. 04

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! This is Part 4 of a series. This part also includes a description of anal sex.

Also, a big shout out and THANK YOU to Volunteer editor who helped me get this in line with the rules and correct some grammatical and syntax errors!!!

Finally, ALL characters in this fictional story are over 18 at the time that any events described in the story take place.

"Mama, how old were you when you sucked your first dick?" Emily asked.

Emily was sitting on the floor at his mother's feet. It was one of his favorite places to sit. Especially when she'd worked at her part-time job and wore pantyhose and pumps all day. He loved to slip her shoes off of her tired feet and rub them, then pull them to his face to sniff the musty scent and rub the nylon hose against his face.

The question caught Edna only slightly off guard. She smiled as she remembered. She paused the movie they were watching.

"Well, that's a rather blunt question," Edna laughed. "But since you asked, it was the spring semester of my freshman year of college. So I was 19."

"Did you like it? That first time?" Emily persisted.

"Yes, honey, I did," she said. "It was something I'd been thinking about, and us girls sat around in the dorm talking about such things. Some of them had already done it, but most of us hadn't. Just talking about it kind of turned me on, so when I finally got the courage to do it I liked it."

"Did you let him cum in your mouth the first time?" Emily asked.

"Well, it wasn't so much that I let him," she laughed. "He just did."

"Did you like it?" Emily asked.

"Not at first, no. It wasn't that I didn't like it, it was that it surprised me. I wasn't expecting it, so I pulled back and let it drip back out of my mouth," Edna answered.

"So when did you start liking it? Because you do like it now, right? I mean, the other night with me you said it tasted wonderful."

"Yes, I did," she responded. "And yours does taste wonderful. I guess I pretty much liked it that first time, and it grew on me from there," she admitted. "How did you feel about it the other night when I put yours in your mouth? Did you like it?"

Emily nodded. "Yes, I did. It surprised me, but when I swallowed it I liked it. But I've tasted mine before. Just not that much of it all at once. Does it all taste the same?"

Edna shook her head. "No, it depends on the man. What they eat and drink, if they smoke, lots of things affect the taste of it. But, overall, I guess I've liked them all."

"It's not just the taste," she continued. "It's the act of letting a man do that. I probably shouldn't tell you this, but it always made me feel slutty, and, well, I kind of liked that feeling."

"Were you a slut, mama?" Emily asked.

"No, honey," she laughed. Then she hesitated. "Would you be disappointed in me if I was?" she asked.

"Oh, no, mama," he told her. "I wish I could be a slut. I tend to hang out with girls a lot at college, and I know which ones are sluts. Sometimes I wish I could be like them. I wish the boys wanted to be with me like they want to be with those girls."

"Do any of those boys know about Emily?" Edna asked. "Or, for that matter, any of the girls?"

"I don't think the boys at college know. A few of the girls kind of know," Emily admitted.

"Well, I'll tell you the truth. I was kind of a slut back then. I was away from home so I didn't have to worry about my dad finding out, and I considered myself a grown woman."

"I would suck just about anyone, but that's all I did. The girls who let boys fuck them were the sluts when I was in college. Girls like me who would give a blow job were just considered a fun date," Edna giggled.

"The sluts I know from the dorm let the boys fuck them," Emily told her. He turned to look up at his mother. "Mama, if I had a pussy I'd be a slut. I think. I think about sex a lot."

"That's the boy in you, Emily," Edna said gently. She reached down and stroked his long hair. "Most young women don't think about sex all the time."

"I wish you had a dick so you could teach me to suck it," Emily said as he laid his head on his mother's thigh.

"You don't need me to teach you, baby," Edna said, still stroking his hair. "When the time comes, you'll know what to do. Is this something you're thinking of doing soon?"

"Maybe," Emily said. "I want to."

"Do you have someone to do it with?" Edna asked her son.

"I think so," Emily said. "Um, you remember my friend Paul."

"Yes, I remember Paul," Edna said. "So have you and he, uh, have you, uh, done things?"

Emily nodded, rubbing his face on her silky hose. "Yeah, last month when we first got back home from college we were at his house talking about sex and stuff, and what we had done with the college girls. You know we never did anything with the girls we knew from here," he told her.

"So while we were talking Paul showed me these adult movies he found in his garage. We think they were his dad's. Anyway, we watched some of them and got kind of horny so we jacked off together. But that's all we've done."

"So, does Paul know about Emily?" Edna asked.

Emily nodded. "He knows I like to wear your panties and dress in your clothes."

"Has he ever seen you dressed in my clothes?"

Emily shook his head. "We've always been at his house at his house, and his mom's things won't fit me."

Edna laughed. "No, I guess not. She is a rather large woman."

Emily giggled. "That she is. She's pretty, though."

Edna smiled. "Yes, she is pretty. I'm glad you can see that in her. Most people just see a fat woman."

Emily nodded. "I know. I think Paul was surprised when I said she is pretty."

"So you and Paul talked about his mom being pretty? Did you talk about me, also?" Edna asked.

Again Emily nodded. "Yes. We both think you're pretty and sexy."

"Um, does Paul know what happened with us the other night?" Edna asked nervously.

Emily shook his head. "No. I haven't talked to him. And, uh, well, I think that should be our little secret, don't you?"

Edna breathed a sigh of relief. "Yes, I think we should keep that just between us."

"So, are you wanting to invite Paul over and introduce him to Emily and suck his dick?" Edna asked.

"I'm thinking about it. Or go to his house as Emily."

"So why go there instead of him coming here?"

"His mom's going to be gone next weekend," Emily told her. "He has some adult movies. He said I could some over and watch them with him and, um, that it would be okay if I brought something to wear."

Edna nodded. "Ah, I see. More privacy there. I was going to offer to go out somewhere for the evening if you wanted me to."

Emily nodded. "I think Paul will be more comfortable at his house than here," he said.

Edna nodded. "Well, I don't have any objection to it. Will you drive over there dressed pretty?"

"I want to," Emily said. "But it kinda scares me. I mean, if anything happened it would be bad if I was dressed pretty."

"True. It's kind of a big step for you," Edna agreed.

"But I really want you to help me with my make-up, and I want to be pretty for him when I get there instead of having to change and try to do my own make-up after I get there," Emily said.

"Well, you decide what you want to do. If you want to put your make-up on here, I'll help you do it."

"Thank you, mama," Emily said. He moved up beside her on the couch and kissed her on the cheek.

"Mama?" he said. "Um, well, I have this, um, this fake dick and, um..."

"You want me to show you how to suck it?" she asked.

Emily blushed. "Yes."

Edna laughed. "Go get it. Um, have you used it on yourself, in your ass?" she asked as he stood to go to his bedroom.

He stopped to look at her. "Yes. Is that a problem?"

"Only if you didn't wash it really well," Edna laughed.

Emily laughed. "I always wash it with dish soap and water," he told her as he turned to go to his bedroom.

When Emily returned with the silicone dildo complete with balls Edna was amazed by how realistic it looked and felt. She had seen pictures of them online, and had considered ordering one for herself... a much bigger one than what Emily returned with. Edna took it from him and looked at it closely to make sure it was clean.

"So, do you ever suck on it?" Edna asked him.

Emily nodded. "Sometimes I pretend I'm sucking a real one while I, um, you know..."

"While you jack off," Edna finished his sentence for him. "Honey, you are going to have to stop being embarrassed to talk about things with me."

"I know, mama, but it's hard. I mean, you're my mom!"

"So, show me how you suck it," Edna said, handing the fake man parts back to her son.

Emily blushed, but he held the tip of the dick to his lips. He kissed the tip, then opened his mouth and slowly pushed the dick in. When he felt the tip of the dick at the opening to his throat he had to stop and breathe, then he pushed it on in until the balls rested against his chin. He couldn't hold it that deep very long before he tried to gag and pulled it back out.

"Very nice," Edna said as she watched the 6" dildo disappear between his lips. She noticed that she could see his teeth scraping along the topside of the rigid shaft.

"You have to keep your teeth off of it," she said softly. "Make sure it's your lips he's feeling."

As Emily worked the dildo in and out of his mouth he wrapped his lips around his teeth. His mother nodded her approval.

"That's better. But not so much with the lips. Here, let me show you." She took the dildo from her son and put it in her own mouth. Emily leaned in and watched closely to see how his mother was making sure her lips were in contact with the dick.

His dick was already hard in his panties, and watching his mom suck the fake cock to show him how caused his pre-cum to start leaking.

Edna pulled the cock out of her mouth and handed it back to him. "Now you try it again."

Emily took the cock from his mother. He opened his mouth wide, like she had, and when the dick was between his lips he closed them down so that his teeth weren't on the silicone shaft as he worked it in and out of his mouth.

"Much better," she smiled. "I knew you wouldn't really need my help. Sucking a dick is just something that comes naturally to a woman."

Emily smiled that his mother referred to him as a woman. He closed his eyes and worked the silicone cock in and out of his mouth, wishing it was the real thing.

He felt Edna moved off of the couch to kneel between his legs. He raised his ass up to let her push his dress up around his waist and pull his panties down to his ankles. He moaned when he felt her hot mouth engulf his leaking cock.

Edna gripped her son's rigid shaft and held it out from his body. She lowered her head, enjoying the contrasting scents emanating from him. She could smell just a hint of musk mixed with dried pee, and the soft lavender of the bath soap he'd used earlier, and the strong scent of his pre-cum that had made a wet spot in his panties and smeared around the mushroom head of his hard dick.

She opened her mouth wide, just like she did on the dildo, and closed her lips down on his hard shaft. She ran her tongue around the bulbous head, tasting the tart pre-cum, looking forward to the stronger tasting fluid she knew would soon follow.

Emily pushed his hips up to meet his mother's mouth. He used one hand to work the silicone dick in and out of his sucking mouth and put the other on the back of her head to fuck his dick in and out of his mother's sucking mouth.

Emily tried to mimic his mother's movements, shoving the fake dick deep in his mouth, even into his throat when he felt her push her face down to his pubis, then swirling his tongue around the mushroom shaped head when she pulled back and ran her tongue around his own head.

He worked the dick in and out of his mouth when she bobbed her head up and down on his throbbing shaft.

Edna moaned as she sucked her son's hard cock. She could taste the steady stream of pre-cum flowing out of his slit, and feel the shaft throb against her lips. She looked up and watched him work the dick in and out of his mouth and heard him moan, too.

She knew he was wishing the cock in his mouth could cum, and she knew the one in her mouth was going to explode soon. She put a hand under her skirt and rubbed hard on her pantyhose and panty covered pussy while she worked her lips up and down his shaft and swirled her tongue around his head.

Emily's legs stiffened straight out, holding his feet off of the floor. His hand on the back of his mother's head held her mouth down so that his pulsing head was at the back of her tongue and her nose was against his smooth pubic bone. He held the silicone dick deep in his own mouth so that the wrinkled silicone balls were against his chin.

His balls twitched and his cock throbbed, sending rope after rope of thick cum into his mother's mouth and down her throat.

Edna moaned and swallowed the musky fluid flowing from her son's throbbing cock. At the same time her inner muscles spasmed and she felt the crotch of her panties and hose slowly get wet with the juices flowing from her pussy. She let Emily hold her head down, breathing through her nose, swallowing when she needed to, until she felt him relax.

When his legs relaxed and his feet touched the floor again and his hand slid off the back of her head. She sat back and looked at him. He still held the silicone dick in his mouth. She moved on top of him, smearing cum from his still oozing cock on the front of her black dress. He pulled the cock out of his mouth when her face was close to his and smiled at her.

"That was so hot!" he said breathlessly.

Edna pushed her lips against his and pushed her tongue into his mouth. Emily moaned and kissed her, tasting his tart, musky cum on her tongue and lips. When she was sure he'd gotten a good taste of cum she pulled her face back from his.

"Yes, it was," she said.

Emily put his arms around her and pulled her to him, hugging her tightly.

"Mama, is it okay that I want to have sex with someone else?" he asked. "I won't if you don't want me to."

Edna lay her head on his shoulder. "Yes, baby, it's okay. You need to experience it. Especially with a man. That's an experience I can't give you, and it's something you need to do."

That wasn't the answer she wanted to give him. She wanted to tell him... to scream- 'no, no, no! You can't do that! I want you all to myself!' But she knew she couldn't. She knew she had to let him try some things, especially with a man. She knew she would keep smiling and help him prepare to go be with his friend Paul, if that worked out. Or with another man if it didn't.

She pushed herself away from him. "I need to go change my clothes," she said. "I got my dress and hose and panties all wet a few minutes ago."

Emily giggled. "I thought I could feel something damp on me. I wasn't sure if it was you or me."

"Honey, all of yours went down my throat!" she laughed as she stood up. "And there was a lot of it this time!"

Emily sat up and looked for his panties. "I know," he said. "Thank you, mama."

He pulled his panties up his legs and tucked his now soft equipment into the pouch, then followed his mother to her bedroom. He sat on her bed to talk to her while she nonchalantly pulled the dress over her head, then her slip.

Emily could see that the panties and hose were soaked. "Looks like you had a lot, too," he laughed.

Edna laughed. "Yes, I did. I guess cock sucking lessons makes us both horny."

"Um, do I need to, um, do anything for you?" Emily asked.

Edna shook her head. "No, dear. That was good enough to satisfy me... for a few hours, at least."

Emily laughed.

Edna hung her dress, slip, hose and panties over the drying rack, then stood naked in front of the vanity to take her earrings, necklace and other jewelry off. She was still a bit surprised by how comfortable she was being naked in front of her son.

"So, let me ask you," she said as she brushed her hair. "Are you planning to do any more with Paul besides suck his dick?"

"Like what?" Emily asked. "Kiss him, things like that?"

"Well, that," Edna giggled. "But what I meant was, what if he wants to fuck you?"

Emily blushed. "I'll let him if he wants to," he said quietly.

"Do you know how to prepare yourself for that?" Edna asked as she pulled a sundress over her head.

"What do you mean? I know I need to have some lube. I've read about that in stories."

"Yes, you do. And you also need to make sure you are very clean... on the inside," Edna said as she sat beside him on the bed.

"You mean like do an enema?" Emily asked.

"That is exactly what I mean," Edna said. "You don't want him to pull out of you with brown stuff on his dick, do you? That kind of ruins the romantic mood. I know that from experience."

"You do?" Emily asked.

Edna laughed. "Yes. It happened to me once. A boy in college... it was our first real date and I didn't really intend to let him fuck me anywhere except my mouth. But things got a little hot and I wouldn't let him fuck my pussy... I was still a virgin then... so he wanted to fuck my ass and I let him even though I hadn't cleaned first. He pulled out and there was poo on his dick and, well, it kind of smelled and... he ran to the bathroom and got sick and I had to go in and clean his dick while he was throwing up."

They were both laughing as Edna told the story.

"So did you have a second date with him?" Emily laughed.

Edna was laughing harder. "No. He would hardly talk to me on campus after that. But as far as I know he never told anyone about it."

"Okay, so, point taken," Emily laughed. "Don't get fucked if I haven't cleaned. Um, mom, I've never done that."

"I know, dear. I'll show you how."

Emily kissed his mother on the cheek. "Thank you, mommy," he said. "I love you so much."

"I love you, too, baby," Edna smiled.

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

Later that night Emily was alone in his room while his mom watched tv. He picked up his phone and called Paul.

"Hey, buddy, what's up?" Paul said when he answered the phone.

"Not a lot," Josh answered, using his normal voice. He'd been using a little softer, higher voice as Emily the past few days. "Um, is your mom still going out of town this weekend?"

"Yeah," Paul answered. "So you want to come over to watch the movies?"

"Yeah, yeah I do," Josh said. "And, uh, you still want to see me dressed?"

"Yeah, I kinda do," Paul said. "You going to bring something to put on?"

"Yeah, something like that," Josh smiled. "I've got a little surprise for you."

"Oh?" Paul asked. "What?"

"I'll show you when I get there Saturday. What time you want me there?"

"Mom is leaving first thing in the morning," Paul said. "So, probably about anytime is okay. Say, sometime mid-afternoon or so?"

"Yeah, that'll work," Josh said. "I'll call you before I come over just to make sure she's gone."

"Okay, that works," Paul said. "See you Saturday!"

Josh could hear the excitement in Paul's voice, as if Paul sensed this Saturday would be something more than just watching movies.

"Yes," Josh said. "See you Saturday!"