Learning with Mommy Ch. 01

"There we go, that's better," his mother said. The brush fit in her hand and she scrubbed tight circles, slowly moving down to his pubic hair. "You were very messy, that was quite a lot."

"Well, it felt really good." It was an understatement, but Jacob still felt embarrassed saying anything more specific than that, it felt too vulnerable to say, "I could have stayed on your breast for the rest of time." It also felt a little melodramatic.

"Turn around sweetie." Jacob turned and finally got to see his mother completely naked. He followed trails of water that originated at her collar bone all the way down to her crotch, where they became droplets caught in her honey-colored hair. He stared at his mother as she shampooed his hair, admiring the gentle bouncing of her breasts. Their gentle motion drew him in like he was in a trance, and without much thought he leaned forward and put his mouth back over her nipple and began to suck and lick again.

"Young man," his mother chided with a giggle, "I'm not done here! We need to get you cleaned up so you can go to bed."

"Sorry, Mom, they're just...they're wonderful."

"Thank you, sweetie." She guided his head back under the stream of the water so the shampoo would wash out, and then began conditioning his hair. As she massaged it into his hair Jacob looked down and continued looking at her pussy. He knew from diagrams in class vaguely what it looked like, but he had never seen one up close. What did it feel like?

"Mom?"

"Yes, sweetie?" She guided him back under the stream and angled his head, so he was looking up at her face. He felt shy again looking her in the eyes.

"Would it be alright if I...touched you...down there?"

She seemed to consider for a moment before asking, "Why do you want to do that?" It wasn't a challenge.

"Well, I guess, I'm curious? I've never seen one," he offered.

"I suppose that would be alright. Here," she took his hand and guided it down to her pussy. "Take your middle finger and gently run it back and forth along the surface." Jacob slowly ran his finger along his mother's pussy. He was surprised at how easily his finger glided.

"It's kind of slimy," he said, more to himself than to his mother.

"That's not very polite, Jacob." His mother grabbed his hand and stopped him. "You shouldn't say that about a woman, it could make her self-conscious."

"I'm sorry, Mom." She released his hand, and Jacob tentatively began to caress her again.

"If you really want to comment, you can say a woman is 'wet,' but always be sure it's clear that this is a positive."

"Sorry, Mom. You are very wet, though."

"Well, that's because I'm aroused, Jacob." Jacob's heart began to pump faster when she said this.

"Is that because of me?"

"Yes, honey," she said with a small smile. She closed her eyes briefly, and he noticed her eyelid flutter.

Jacob enjoyed exploring his mother's pussy, he noticed that towards the front there was a little bud and occasionally when his finger would brush over it his mother would twitch. She reached behind him to turn off the water, and the two of them stood in the shower. Jacob's mother's hands tangled in his wet hair and she closed her eyes again. Jacob continued to slide his finger. Then, his mother grabbed his hand and moved it until his finger was touching the bulb.

"Keep your hand here and do this with your finger." His mother demonstrated on his knuckle the tight circle she wanted him trace. Jacob did as he was told and was rewarded with a look of ecstasy on his mother's face. She scrunched her eyes and bit her lip.

"Sweetie, come lick my nipple again, do what you did earlier." Jacob was happy to accept. He stepped a little closer and wrapped his lips over his mother's nipple and flicked at it with his tongue. He barely had to lean down to reach them.

"Mmmm." She shuddered out with a breath, her grip firmer on his head, pulling his head into her chest. The pressure was almost too much for Jacob. His mother gasped loudly, and her body shook with a violent tremor followed by several smaller ones. Jacob felt the pressure on his head ease, but he continued to play with his mother's bulb.

His mother twitched several times before softly asking Jacob to stop.

"Sorry, Mom."

"No, that's okay, thank you for that." She leaned down and gave Jacob a gentle kiss on the lips.

She stepped out of the shower and grabbed a towel and Jacob followed. It felt funny as he stepped out and looked down to see he had a stiff erection jutting out from his body. It had been only 30 minutes since he came all over his mother and he was surprised to see he was erect again.

His mother looked down and seemed surprised as well, but also pleased.

"Do you need some 'relief' again?"

Jacob didn't want to impose; he felt a little embarrassed that he was so aroused again. "Oh, no, that's okay, Mom."

"Honey." She said it with heavy skepticism.

His mother dropped the towel and knelt in front of him and put her hand on his hip, mere inches away from his cock. She looked up at him and raised her eyebrows inquisitively. Jacob bit his bottom lip in anticipation and nodded with trepidation. His mother closed her hand around his cock and started to jerk him off.

"I'm going to go a little faster, sweetie, because you have school in the morning." Jacob nodded again as he blew an overwhelmed breath out. He looked down at his breathtaking mother and nearly lost it as she moved her face even closer to his cock, stuck out her tongue and used the tip to play with the bottom of his cockhead. She used quick lapping motions in concert with fast strokes and though he tried his best, Jacob couldn't hold out any longer. He tried to warn his mother but all he could muster was a quick "oh fuck," as cum shot out of his cock and onto his mother's waiting tongue. He watched in awe as cum pooled quickly on her tongue. His mother made sure she got all of it out before swallowing it down.

His mother stood up, grabbing the towel, and began to dry her boy. When he was dry, she looked down at him and pulled him in for a hug.

"Alright," she said. She followed Jacob back into his room and grabbed her robe. "Look at that, not a drop on it," she said as she slid it on.

Jacob got into bed and his mother came to sit on the mattress.

"Sweet dreams, honey." She kissed him on the forehead.

"They will be!" His mother laughed at that as she walked out of the room.

Jacob lay in the dark, basking in the events of the evening. He'd cum twice! And he was pretty sure he'd made his mom cum too. A faint whisper snuck into the back of his mind, "What does this mean? Will it happen again?" the voice said. He did his best to shut it out, focusing on the vivid images of what had happened. Before long the voice was gone, and Jacob drifted off into sleep.

Jacob woke to his mother's gentle nudging, as usual. Except his room was a bit darker than he expected.

"What time is it?" he asked groggily. His mother was wearing a white tank top with buttons that were undone, coyly revealing some of her cleavage, and faded orange cotton shorts that hugged her hips. Her hair was up in a messy bun.

"About 6:00, I know it's a little early, but I just wanted us to have time to talk about last night before you went to school. I think it will be less distracting for you."

Jacob's heart began to sink. "Last night was all it ever will be," he thought to himself.

"Honey, last night was...special." It didn't sound like a good thing. "Last night you made clear to me that you were in a lot of emotional pain, and I wanted to help you as best I could, and that's why it happened."

"Ok." Jacob tried not to sound sullen.

"But you also said something last night that I think we need to address. I heard a lot of anxiety about sex, about your body, about whether you are attractive. Would you say that's accurate?"

Jacob didn't know where this was going. "Yeah. Yeah, I suppose it is."

"Oh sweetie, you're very handsome and there is nothing wrong with you." She said it with such kindness.

"Well, you have to say that. You're my Mom."

"What do you think is wrong with you, honey?!"

This conversation was beginning to get embarrassing again, and he started to think they could've had this talk later in the day.

"I'm. Small. I'm taller than maybe ten girls in my whole senior class, and not by much. I just know that's not what girls want."

"Honey," she stroked his cheek as she spoke to him, "attraction isn't as simple as that. For one, not all women are the same. I know plenty of women, myself included, who are attracted to both tall and short men. So don't take yourself out of the game before you've started playing. You are handsome, and the women worth your time will see that. Secondly, women won't be attracted to men who are apologizing for existing. You've got to have confidence. That's what makes a man sexy. Being confident, being kind, and being intelligent are what makes a man sexy. You are kind and intelligent, we just have to work on your confidence."

"Easier said than done," Jacob thought. "Well, you know, I'd be a lot more confident if I had a bigger dick," he said with a scowl.

His mother smiled and shook her head at him. "And why do you think you need a bigger dick, sweetie?"

"Everybody knows that if it's bigger it feels better!"

His mother sighed with a mixture of frustration and exasperation, "Where you'd get that idea? Pornography?"

Jacob could tell from how she asked that if he answered "yes" she'd explain why that was silly. "Well, I know what you're gonna say, but you don't get it, you've got the body of a..." he was going to say pornstar but thought she might not appreciate it, even though it was a compliment.

His mother cocked her eyebrow up. "You have a great body, Mom. I don't think that's a secret."

"Well, thank you. But let's use me as an example. I get the feeling you like my big boobs, right?" She said this with a smirk.

"...Yeah."

"But I imagine there are girls at school that you are also attracted to, do all of them have big boobs? As big as mine?"

"Well, no. But that's different isn't it? That's got nothing to do with how sex ends up feeling."

"That's true, but my point is that even if you have a preference for one thing or another, you'll find yourself attracted to people who are different. It all depends. Also, honey," she put her hand on his chest and ran her thumb back and forth, "are you forgetting what happened last night? You made me orgasm without even using your penis."

Jacob could feel the blood rushing to his penis as his mom spoke about last night.

"I won't lie and say that penis size doesn't matter at all when it comes to penetration, but honestly, it's really only significantly below average penises where you start to have some issues. But you're much bigger than that. I've seen and held your penis, Jacob, and I can tell that what you have would fill me up plenty."

More blood rushed to his cock, he could feel it stiffen and lift off his torso, pressing into his comforter. His mother kept going.

"But vaginal penetration is just one part of sex. If you love giving oral sex a smaller penis is much more manageable, and with anal. Well, I would never do anal with a penis bigger than yours."

Jacob's mother clearly didn't realize the effect her words were having on her son.

"Mom, why are we talking about this?"

"I'm going to help you with your confidence. Think of it like sex-ed, but homeschooled. I realize that by sheltering you as much as I did that there are some gaps in your education. I also realize that what you're being taught in sex-ed at school leaves something to be desired."

"I'm a little lost, Mom."

"I want to teach you about pleasure, Jacob, so that this year, or when you go to college next year, and you have your first sexual experience, you'll feel ready. And not only that, but you will make your partner feel respected, you'll turn her on, and you'll make her want even more."

"I mean, I guess that sounds good. But, how's it gonna work?"

"Well, it'll be a little bit like last night," she said playfully. "But last night was your birthday, so it was about you. Some 'lessons' will be about you finding out about you, about finding out what you like and how to communicate that. But other lessons, those will be about me. How does that sound to you?"

Jacob couldn't really believe what he was hearing. "Um, I think that sounds pretty good." Jacob couldn't suppress his grin.

"Oh, good!"

Her response made Jacob realize that she had been kind of nervous proposing this idea to him. If only she knew.

"Thank you, Mom. Thank you, thank you!" Jacob sat up in his bed and gave his mom a hug. Her breasts crushed up against his chest. His sitting up also moved his comforter down his body and when they separated the comforter remained, revealing part of his erection. His mother looked down at it.

"It seems all this talk got you a little excited." She pulled the comforter further down a revealed his entire penis.

"Yeah," he said sheepishly.

"Well, I was going to start our lessons this evening. Buuuuuuut," his mother reached down and surrounded the head of Jacob's cock with her fingers, and as she spoke, lightly dragged her fingernails over his sensitive crown, "I did wake you up early so you weren't distracted with last night hanging over your head. And this seems very distracting."

"I think it would be," said Jacob. His mother's seductive torture made Jacob spasm.

"Well, then, I suppose I should take care of this." She moved her hand down to squeeze Jacob's balls. "We can use this as a learning opportunity, but I'll warn you, other lessons won't be like this. Unless I say otherwise the expectation will be that for every orgasm I give you, you have to give me one back. Understood?" At her question she tugged down on his balls, it was uncomfortable, but in a way that Jacob enjoyed.

"Yes, mom."

She maintained her grip and said, "During lessons you will call me mommy. Understood?"

"Yes. Mommy."

"Good." His mother withdrew her hand and stood up, pulling down the comforter to his ankles. She pulled her tank top over her head and hopped onto the bed in between Jacob's legs. She leaned over his cock and dropped a dollop of spit on it, which she spread with her hand before beginning to stroke her son.

Jacob luxuriated in the feeling; he could get used to this. He looked at his mother and noticed her nipples were poking out. He sat forward and began to play with him, but his mother pushed him back.

"No, no, sweetie. This handjob is already turning me on, if you start playing with me I'll have to finish and we don't have time." She smirked at him. "Don't worry, I'll get mine later."

"Okay, Mommy."

"For now, we're going to work on dirty talk. Do you like what I'm doing right now?"

"Yes, Mommy."

"Tell me about it; encourage me."

"Um," Jacob struggled to think straight with his mother's hand gliding up and down his cock. "Um, I really like it when, whoo, when your thumb goes over the sensitive part on the underside of my cock."

On her next stroke his mother swiped her thumb. "Yeah, yeah, right there. That feels great."

"Very good, baby. You don't need to be graphic, but being able to say what you like, and make your partner feel like she's doing a good job at the same is a turn on for her, and it will make sex more enjoyable."

"Okay, Mommy, whatever you say."

"Open your eyes sweetie, don't you want to see mommy's breasts?"

Jacob admired his mother's bouncing breasts and the way they moved with her strokes as she gradually increased the pace.

"Mommy?'

"Yeah, baby?"

"I, I really like it when you play with my balls. Can you do that while you jerk me off?"

"You want mommy to play with your balls?"

"Yes, Mommy, please." Her mouth twisted into a devilish grin as she began to massage his balls.

"Does that feel good, baby?"

"Fuck, that feels really good. I think I'm pretty close."

His mother lowered herself down until her head was just above Jacob's cock. "Do you want to cum in mommy's mouth again? Did you like that? Filling my mouth with cum?"

The way she was talking was pushing Jacob to the brink. "Mommy, I'm about to cum!"

His mother stopped stroking him, and tightly gripped the base of his cock. She jutted out her lips and formed a tight 'O' and lowered it down over the head of Jacob's cock. She quickly moved her head up and down and drew her lips inward each time she neared the tip of his cock, keeping a tight, wet seal on his cock. Jacob's hips began to rock and a second later his mother began to slurp his cum down her throat. All told Jacob shot four ropes of cum out before his mother began to slowly stroke his shaft again, coaxing out every last drop.

As she lifted her head up Jacob looked at his cock, there was only the sheen of his mother's saliva. His mother crawled on top of him and gave him a deep kiss on the lips. There was a funny taste Jacob didn't recognize.

"Ugh Mom, what was that taste?"

"That was your cum, Jacob," she said suggestively, as if it were obvious. "One day your mouth will taste like my pussy when you kiss me. Fair is fair." She gave him another kiss and hopped off the bed. She grabbed her tank top off the floor and left his room.

"Time to get dressed, I'll get breakfast on!" she called from the hall.

Niamh Doherty raised her hand and Jacob peeked at her midriff. Niamh was the prettiest girl in Jacob's year as far as he was concerned. She had dark brown hair, bright blue eyes, and fair skin. She was also around Jacob's height, only a little taller. Jacob kept looking at the band of skin between her sweater and her skirt until it disappeared as she lowered her hand. The sweater hugged her petite frame, and Jacob wondered what it would be like to reach up her sweater and squeeze one of her cute, small breasts.

Catching himself in his daydream, Jacob sat up as Niamh finished giving her answer. Jacob found her Irish accent endearing. Niamh had moved to the area a few years ago, and despite being pretty, the popular girls in school decided not to include her. Jacob often saw her in the library at lunchtime.

"How fun would it be to fool around somewhere in all those bookshelves?" he thought to himself. "Wow, what a difference a day makes." Jacob realized how little shame he felt after his daydream. This was new for him. Whereas before his birthday he would feel intense shame about how unrealistic his fantasies were, thanks to his mom, Jacob no longer felt like it was completely out of reach.

"How was your day, sweetie?"

"Good," Jacob got in his seat and his mom began to pull out of the school parking lot. Jacob spotted Niamh as they rolled away from the school and his head followed her until she was out of sight. Jacob turned back to see his mother smirking.

"What?" he asked, blushing.

"Well, who was that?" she said with a laugh.

"Oh, um. That's Niamh."

"She a friend of yours?"

"Um, not really, I guess. We'll wave at each other in the library at lunch sometimes, but I've never really spoken to her."

"What's stopping you?"

"I'm shy I guess."

"I think you should say hi the next time you see her in the library. Just go up to her and ask her about something from class. See how it goes, the worst that could happen is you have a short conversation."

"I'll get the dishes, Mom." Jacob stood and grabbed his plate and went to grab his mother's.

"Thank you, sweetie." She kissed Jacob on the cheek. "Just rinse everything and throw it in the dishwasher. I'm going to change into my PJs but meet me on the couch."

Jacob entered the living room and found his mother lounging on their couch. She'd changed into a set of navy linen pajamas. The top was short sleeved with a collar and buttons, and the bottoms were drawstring shorts, leaving most of her smooth tan legs visible.