Fixing Jacob

Claire got up to grab another bottle of wine. When she came back she poured herself another glass and also refreshed her daughter's.

"I can't believe this. Holy shit. While sis and I were at soccer camp you were fu... uh, being with Mike?!'

"Oh that was such a wonderful week. I turned that kid into a magnificent lover in no time. But you should have seen that poor boy at first. I had such a hard time getting him inside of me. He just kept cumming everywhere! But when I finally got him settled down oh boy did we have a ball!"

"TMI mom! TMI!"

A brief silence fell over the room that was eventually broken by Claire.

"You know what I think of most Sherry? I think about what would have happened to him if I hadn't done what I did. He might have drifted through life with zero confidence. Probably stuck in a dead end job, married to a woman he can't stand. But no. He's on top of the world and I regret nothing. I mean really Sherry, what am I guilty of? Giving my son unshakeable confidence in himself? I'd do it again in a heartbeat. My only regret is that soccer camp didn't last for two weeks."

Sherry was silent for several seconds and then got up and poured herself more wine.

"This is a lot to take in mom. I mean, what you're saying is just, well...it's crazy. There has to be a better way. Maybe he'll meet an understanding girl or..."

"And maybe he won't. What then? Like you said, it's in his head. And I only know of one way to get it out. And it's a guaranteed foolproof method. Plus, it's a lot of fun for both people! Speaking of which, I can't remember the last time I've heard you talk about a man in your life. I raised you to enjoy sex and have lots of it. I mean, look how beautiful you are? You should be spending a lot of time in the sack with a man. This could help both of you. Knock out two birds with one stone."

"I don't know mom. It's just been difficult getting into relationships since the divorce."

"Who said anything about a relationship," said Claire. "I'm talking about sex. Don't date these guys if you don't want to. But that doesn't mean you can't still have fun with them. And the same goes for your sister Sara as well. I don't think she's been getting any either."

"This is a lot to process mom. I should go," said Sherry as she got up.

Claire walked her daughter to the door, "Sherry, just remember that everything I did was done out of parental love and concern. Being a parent means being willing to do anything it takes. And besides, if you have the added advantage of looking like you do then it would be negligent not to use those natural gifts."

"What are you talking about mom," asked Sherry as Claire opened the front door.

"Sherry, you're extremely attractive. Every man would love to be with you. And I bet all of Jake's high school buddies refer to you as a MILF and definitely wank it to you."

"Mom..."

"You know it's true Sherry. So what I'm saying is, any boy would be thrilled to be ushered into manhood by you. And that includes Jacob. And you know what else Sherry? I've been pretty fortunate to keep my looks as well. I still get plenty of attention."

Sherry stepped out onto the front porch and then turned to face her mother.

"You're beautiful mom, you always have been. But what's your point?"

"My point is Sherry, that if you don't step up and fix Jake then maybe I will. Have a good evening dear."

And with that Claire shut the door on the stunned face of her daughter.

Sherry drove home in a daze. When she got inside she poured herself another glass of wine and sat down to think about everything her mother had said. She didn't see Jacob anywhere which meant he was in his room. She was glad because she was afraid of how she would look at him.

Her phone buzzed and she looked down and saw that she had gotten a text from her mother. She opened it up.

"Just got off the phone with your brother. He has great news. He's done so well financially that he's retiring early. Like I said, I regret nothing."

Sherry just shook her head and put the phone down. She finished her wine and then went to bed.

The next day which was Friday, Jake came home from school still sulking. After dinner he excused himself and went to his room and didn't come out. It was Friday night and usually he was running around town with his buddies getting up to god knows what. Sherry didn't like this recent development at all.

Saturday was more of the same. Jake sulked all day and didn't go out with any friends. Sherry grew increasingly worried for him. At the same time she kept obsessing about what her mother had said. It was true that her brother Mike was the perfect man in every way. Handsome, in shape, amazing, beautiful wife, great kids, and now on top of everything he was retiring early because he had been so successful. And here was her son, moping and not believing in himself. And obsessing over his problem.

By Sunday afternoon Sherry had decided to act. She wasn't sure what she was going to do or how she was going to do it, but she knew she was going to need booze. So she made herself a stiff drink. And then another.

With her second drink in hand, Sherry went to her closet and looked for something to change into. The alcohol was making her feel warm. And knowing what direction she was going in made her feel hot with sexual tension.

She eventually chose a pink, babydoll negligee and put it on. She looked incredibly sexy in it. It showed off plenty of the cleavage of her ample bosom as well as plenty of leg, stopping a few inches down her thighs. She admired herself in the full length mirror, noting how toned her calves looked. Sherry always considered her legs as one of her best features. She then put on a sexy, matching pink robe that came to mid thigh.

She went back to the kitchen and made a third drink. She walked around her house feeling sexy in her lingerie and robe, sipping her drink and thinking about what to do. And then she finally decided on a course of action. She put her drink down and went to the bathroom closet, where she retrieved the bottle of baby oil and also a full sized towel, and then headed to Jake's room.

Jake was sitting at his computer shirtless, looking at porn and jerking off. His gym shorts were down on the floor around his ankles. He had several tabs open, all with the stepmother or implied incest genre with an older woman and younger man. He was well into it when he heard his mother knocking on the door.

"Fuck," he murmured while he quickly shut down the tabs and pulled up his shorts.

"Jake, can I come in?"

"Just one second," Jake said as he quickly went to his bed and laid down with his iPad strategically placed to cover his boner.

"Ok!"

Sherry opened her son's bedroom door and walked in. She saw Jake's eyes go wide when he saw her in the robe and looked her up and down and lingered on her exposed legs. It sent a thrill through her. He then fixed his look onto the towel and bottle in her hand.

"What's going on mom?"

Sherry walked over to his bed and sat down on it.

"Sweetie, it's about your problem that you told me about. I think we should work on getting this figured out."

Jacob gave a confused look at the towel and the baby oil.

"Ok. Uh, how?"

"Jake, you're going to need to trust me, ok? I promise I'll never laugh at you or judge you. I just want to do everything I can to make sure you are physically and mentally healthy. And the best way I can do that is prove to you that this problem is really not a big problem at all for a teenage boy. Does that make sense?"

"Uh, I...I guess."

"Jake, you do trust me don't you?"

"Well, yes. You're the best mother ever. I mean I told you about it right?"

"Yes you did. And I'm so happy that you did because now I know what to do. Now, since you trust me let's get started ok?"

Sherry got up and stood before Jacob and kept her eyes on his. She then loosened the robe's tie and allowed it to fall open, revealing the babydoll negligee underneath. She smiled when she noticed his eyes wondering her body. She then shrugged her shoulders, causing the robe to fall to the floor and stood before her son in just the lingerie.

"How do I look Jake?"

Jake was extremely nervous and excited and so he hesitated. There was a ton of sexual tension in the air.

"You look, you look beautiful mom. You look really sexy."

"Thank you Jake. Well, this beautiful, sexy woman wants to help you with your problem. You should probably take advantage of this opportunity don't you think?"

Jake just weakly nodded.

"Remove your shorts Jacob."

Jake didn't move at first but just stared at her in stunned silence. Her eyes were full of love but also deadly serious. He pushed away his iPad, revealing his hard on, which brought a slight smile to Sherry's face. He then slowly slid down his shorts.

"Your boxers to Jake."

Jake gulped, and then slowly slid down his boxers, freeing his cock. Sherry gave a slight gasp when she saw it. Her boy definitely did not inherit that piece of equipment from her useless ex-husband. Jake was sporting an erection that was at least eight inches long, and very thick. It was so hard that it was laying on his stomach.

Sherry sat down next to him and stared at his cock.

"Jacob, you are one lucky boy. Do you understand?"

"I'm, uh... I'm not sure what you mean mom?"

"Jacob, this is one very impressive cock. This is exactly what women want. And I'm not talking about stupid, inexperienced high school girls."

"Really," asked Jake as he broke out into a smile. He liked what she said but wasn't sure if it was just her trying to lift his spirits.

Sherry then took the bottle of baby oil and opened it. She squirted some into her hand and then squirted a line of oil along his exposed shaft, causing him to gasp.

"Now Jacob, mommy is going to get you off. And you are going to cum really quickly. But we are not going to stop. We're going to keep going so that I can prove something to you. Do you understand?"

"Uh, I think so?"

"That's a good boy. Now you just lay back and enjoy this. Let mommy do all of the work, ok sweetie?"

"Ok mom."

Sherry then reached out and took his cock in her hand and slathered the oil all over it, causing Jake to gasp again. She was barely able to get her hand around the whole thing. She then began to stroke him.

"Ahhh...oh god...mom..."

Sherry had not even stroked him more than two or three times and he erupted. He gasped and groaned as he shot his cum straight up into the air, landing down on cock, his mother's hand and arm, and his stomach. He was mortified but all his mother did was show him love and encouragement.

"Oh baby that's it! You're doing such a good job sweetie! Shoot that cum out," said Sherry as she continued to stroke his cock.

"Doesn't it feel good baby?"

"Ah! Oh god...so good mom..."

"Mmmm...don't you just love a good orgasm," she said while she continued to stroke his cock.

Jake was gasping for breath as his orgasm finally subsided. He noticed that his mother's hand was still sliding up and down his oily dick. It felt wonderful. He laid his head back and enjoyed the sensations as she continued to jack his dong.

"Jacob baby? What do you notice sweetie?"

Jake lifted his head and looked at his mother's hand going up and down on his still erect cock.

"Uh, I'm...uh...I'm still hard?"

"That's right sweetie. Your cock is still hard as a rock and ready for more fun. Just think, that stupid Cindy could have had this beautiful thing inside of her, giving her pleasure like she's never known. But she's just too dumb. Cumming too soon is just not an issue for teenage boys. And guess what? We are not done sweetie."

"We're not?"

"Oh no. Mommy's not stopping. Mommy's going to prove to you how your problem isn't a problem at all. Now you just lay back and enjoy this ok?"

Jake rested his head back on the pillow and luxuriated in the feeling of his mother's hand stroking his lubed up cock.

"This is such a beautiful cock baby," said Sherry as she opened the bottle of baby oil again and squirted more onto his cock. She then put it down and started to use both hands on him. She took one hand and massaged his balls while she stroked his shaft with the other.

Jake started moaning softly. It was the best sensation his dick had ever felt.

The whole ordeal had Sherry extremely horny and wet and she longed to reach between her legs and give herself some relief.

"Such a beautiful cock," Sherry repeated. "So hard and ready for more fun. My god this dick is going to give so many women so much pleasure. Stupid, stupid Cindy. Such a stupid little girl."

It took Sherry all of her willpower to keep from leaning down and taking Jake's cock into her mouth.

Jake started to thrust his hips in time to her strokes. He began to moan out loud and felt another orgasm building.

"Oh...oh mom...ahhh...oh shit...I'm gonna...I'm..."

"Go ahead baby. Orgasms feel so good don't they? Go ahead and shoot your jizz again sweetie. Mommy isn't stopping. We're going to keep going ok?"

Jake's hips started to buck and he sent another load shooting into the air, falling again on his cock, stomach and her hands.

Sherry continued to pump his cock, wishing she could lean down and put the spurting member into her mouth. But she knew she had to take this one step at a time.

Jake finally stopped bucking and settled back into the mattress and caught his breath as his orgasm ended. Sherry never missed a beat and her hands continued to stroke his meat and massage his balls. He closed his eyes and several minutes went by as he just enjoyed the feeling of her hands on his dick. Sherry then spoke up again.

"Jake baby, take a look hon. Look how hard you STILL are? This eighteen year old cock is still ready for fun. Lots more fun. And guess what sweetie?"

"Uh, we're not stopping?"

"That's right baby. We're not stopping. Cindy could have been getting laid this whole time. What a stupid little brat. I mean just look at this beautiful cock. So beautiful. Such a marvelous pussy hammer."

"Do you mean that mom?"

"Oh yes Jake! This is an absolutely magnificent piece of meat. Look how fat it is? And these bulging veins in the shaft. Any woman would love to have this filling her pussy walls. You're going to be having so much sex Jacob. You're so lucky sweetie."

Her hands on his dick and her words had Jacob feeling like he was floating. He never wanted this to end.

Sherry cooed into his ear and continued to stroke his dick, pausing just to apply more baby oil. She then broke out in giggles.

"What's so funny mom?"

"Oh Jacob, I always noticed your bulge whenever you wore your wrestling singlet. Your grandmother noticed it too. But I had NO idea it was going to be this amazing. This cock is just perfect. I'm so happy that my baby boy has a great package. My baby is going to be just fine. Now you just lay back and continue to enjoy this."

Jake smiled and laid back, loving the handjob and his mother's compliments. He felt like a million bucks. And then he started to feel it again. His hips started to move to her strokes, and he knew it was coming.

"Mom?"

"Go ahead baby. Cum for mommy sweetie."

Jake's whole body tensed up and he shot his third load into the air. Sherry sped up her strokes and encouraged him.

"That's it baby! Cum for mommy! Shoot your load sweetie! That's it! Such a good, good boy!"

Jake finally collapsed back into the bed and closed his eyes. Sherry continued to stroke and looked lovingly down at her boy.

She stroked him for another minute and then stopped and grabbed the towel and wiped them both down. She then looked at the clock on his nightstand and then spoke to him.

"Jacob sweetie. Let's review what we just witnessed here. Mommy stroked your dick and you premature ejaculated almost as soon as I touched you. But we knew that was going to happen because it's in your head and you've been obsessing about it. But what else happened?"

"I stayed hard?"

"That's right sweetie. You stayed hard as a rock and came two more times. I stroked your cock for forty five minutes. Forty five minutes Jacob! And you stayed hard the entire time. That's a lot of lovemaking that stupid Cindy missed out on. See baby? There's nothing wrong with you."

Jake smiled and nodded his head.

"Now sweetie, you get some sleep. Tomorrow night we'll work on this some more ok?"

Jake broke out into a huge smile and nodded his head in the affirmative. Sherry leaned down to kiss him goodnight, but it was an open mouthed kiss and she lingered. Jake pushed his tongue into her mouth and she reciprocated, and they made out for a few seconds. She then broke the kiss and sat up.

"That was nice Jacob. My baby's a good kisser too. You're going to be just fine. Goodnight sweetheart."

Sherry then got up, grabbed her robe and left his room.

Jacob relived the events of the last forty five minutes in his head and wondered what the next night would bring until he eventually fell asleep.

TO BE CONTINUED...