I MIGHT PULL THIS ONE AND REDO IT. I THINK I MIGHT BE ABLE TO MAKE IT HOTTER. WE'LL SEE.
Jacob came home from school and entered his house. He gave his mother who was sitting on the couch a half hearted hello and then sulked off to his room. He and his mother were very close and Sherry knew that something was wrong and gave him a few minutes before checking on him. She had been divorced from his two-timing father for several years and had divorced well, not needing to work.
She walked to his door and gently knocked.
"Sweetie, can I come in?"
"Sure mom."
She opened the door and walked into his room. He was sitting at his computer playing a game, but she could tell that he was still emotionally in the dumps. She walked over to his bed and sat down.
"Jacob, please stop playing that game and tell me what's wrong. I haven't seen you this upset in a long time."
Jake shut down the game and turned around to face his mother.
"I'm sorry mom. I don't, uh...I don't think I can talk about it."
"Why not honey? We've always been very open with each other. You know I would never judge you. What's wrong?"
"Mom it's just, at school uh, the other kids they..." he trailed off and stopped talking.
"Jacob what? What are the other kids doing? I can't imagine you getting picked on being the star wrestler and all."
Jacob chuckled, "You'd be surprised mom."
"Wait? What? You're like one of the best athletes and you have tons of friends. How are you possibly being bullied?"
"It's not, I'm not being bullied mom. I'm just being given a really hard time. It's because of this past weekend."
"What happened this weekend? You went out with Cindy on Saturday. Did something happen?"
Sherry was very intrigued to get to the bottom of this. Her son had really filled out over the last two years, and was now a strapping young man and star wrestler at the 175 pound weight class. He had grown into an incredibly good looking kid as well, and combined with his athletic talents it had made him extremely popular. Especially with the girls. He had been casually dating at least one or two girls for the past year.
Sherry assumed he was sexually active and unlike most parents she couldn't be happier if he was. She was extremely liberal when it came to sex and felt that as long as it was safe, people should have as much sexual fun as possible, especially in their prime. She had given Jacob the whole birds and bees lessons, long talks about consent, and also made sure he understood how to use condoms and other forms of birth control. As a mature adult who remembered what it was like to be a kid, she didn't see the point in pretending that sex was something that their 'precious baby' would never do unlike most parents. This free thinking openness had actually come from her own mother and Sherry couldn't have been more thankful for it.
Jake remained silent and stared at the floor.
"Jacob, did something happen on your date with Cindy," Kathy pressed.
Jake kept looking at the floor.
"Sweetheart, please tell me nothing bad happened. We've talked about consent and how no means no so just please tell me that..."
"NO MOM! Nothing like that happened! Hell, it's actually hard to ask for consent when your clothes are being torn off."
Sherry just looked at him with her mouth open, and then finally said, "Wait, so Cindy was the aggressor? What happened?"
Sherry smiled and found it comical that a girl tried to rip her son's clothes off. She had been amazed at just what a beautiful boy he was growing up to be. Squared jaw, puppy dog hazel eyes, and a streamlined, athletic body that was built for action. He was the kind of boy that she used to follow around and pine for when she was in school. And the kind of boy that if she was alone with, she'd have a hard time not tearing their clothes off. Sherry wasn't a big fan of Cindy, seeing the girl as a dumb slut, but she couldn't blame her for being sexually agressive with her Jacob.
This all went through Sherry's mind as she waited for him to reply.
Jake let out a long sigh and then decided to just spill it.
"So Saturday I went over to Cindy's because her parents were out for the evening. I'm sorry I know I told you we were going to a party. That was a lie."
"Jake, I don't give a shit about that. I told you I'm fine with you having sex just so long as it's consensual and safe."
"I know mom, but it's easier just to tell a small lie then instead say something like, 'See yea mom. Cindy and I are gonna bang for the first time! Don't wait up!'"
"Ok, I get that. I actually appreciate that. Now go on."
"I can't believe I'm telling you this. Well, as soon as I got to her house she grabbed me by the hand and led me to her bedroom. We started making out and she tore off my shirt and then unbuttoned my jeans. She then pulled my pants and boxers down to my thighs and... Mom, I..."
"Go on sweetheart. You've told this much, now finish the story."
Jacob sighed and then continued, "She was kneeling in front of me, and said something about it being the biggest she'd ever seen. I was really, uh...I was very, um..."
"You had an erection?"
"Yeah. I was very hard and super excited. She, uh...she reached out and grasped it and I, I...uh..."
"What happened sweety?"
Jacob closed his eyes and put his head down in shame, "I came. It shot all over her face."
Sherry burst out laughing and covered her mouth with her hand.
"Mom! What the hell! This isn't funny!"
Sherry tried hard to stop laughing but couldn't. Finally, in between giggles she managed to say, "I'm so sorry sweetie. I'm really sorry but c'mon. It's a pretty funny scene to imagine."
"No it's not! It was awful!"
"Baby, why is that so bad? It happens, especially to young boys who get excited. I mean, what happened next? She cleaned up and then you two had sex?"
"No! She was mortified and she freaked out. Said she couldn't believe that I just blew a load on her and couldn't even wait until I was inside her. She kept saying what a loser that I was. I apologized and apologized but she just kicked me out. I guess I'm just going to be a virgin forever."
Sherry was surprised to hear that her son still had his cherry. She had assumed that a kid as good looking and as popular as he was would have definitely been sexually experienced by now.
"Jacob baby, Cindy's not very bright is she? I mean, isn't she in the dumb classes?"
"Yes mom. She's dumber than a box of hammers but she's so hot."
"Well, that's it then. She's not very bright and she's also very young and inexperienced. If she was any smarter she should have known what she was dealing with. A young stud who's erection probably didn't even go down at all. She should have just taken you to bed and had a lot of fun. But she's dumb, so what's the big deal?"
"Mom, before I even got home she had told all of her friends. And now at school everyone is teasing me about being a premature ejaculator. The girls all point and laugh, and the guys are calling me 'quick draw.' It's awful! How am I going to ever get another girl after this?"
"Oh baby listen, this is just high school. It feels like the whole world but it's really small. This will all simmer down. You're so good looking and popular. You're going to get other chances. I promise."
"Mom, you don't understand. This isn't the first time."
"What do you mean Jacob? You've had this problem before?"
"Yes. I mean the circumstances were different but I just can't seem to control myself. Whenever Cindy and I would have make out sessions and grind on each other, I'd always cum in my pants. Like, almost every time. Only she didn't notice, or was too dumb to notice. And last year, when I met this one girl after the game from the other school. She was going to go down on me in the car, but I came before she was even able to put her mouth on me. I'm afraid I'll never have a successful encounter. And it's in my head now. Every time I get close I can't stop thinking about how I'll screw it up."
This last part concerned Sherry. She was a psychologist by training and understood how bad things could be once they became a mental obsession. But sexual dysfunction was not her specialty and she was at a loss for a solution. So all she could do was be reassuring.
"It's going to be fine sweetie. I promise. We'll get through this ok? I'm sure we can get this fixed. Now, I'm going to get started on dinner. I'll call you down when it's ready."
Sherry rose and went to leave. She stopped at the door and turned around.
"Jacob, thank you so much for being honest with me. It makes me so happy to know that you trust me with these things. We're going to get you through this. Just let me figure this out ok?"
"Sure mom," said Jake, assuming that she was just trying to keep his chin up.
Jacob watched her leave and admired her shapely legs and nice, firm butt as she walked away. This was something he had found himself doing often lately. He always knew that his mother was attractive, but it all changed last summer when she wore a bikini to the local pool. It was a very conservative bikini, but it still showed off her very attractive shape.
Sherry was thirty eight and resembled the actress Kathleen Quinlan when she was Sherry's age. She was extremely attractive in a girl next door sort of way. She kept her light brown curly hair short, just off the shoulders. She did lots of yoga and also swam and played tennis to stay in shape. She had large, firm breasts, a slim waist, shapely legs and a firm, juicy ass. And it wasn't lost on Jacob's friends at the pool that day.
The following Monday at school, more than a few of Jacob's friends teased him about how they thought of his mom in her swimsuit as they pulled their chains that weekend. He took it in stride since he wasn't the only student who got teased for having a hot mom. But it did make him feel different about her. She was a MILF. And worst of all she had started to invade his fantasies when he had his nightly and morning jerk off sessions. He never intentionally fantasized about her, but she would always appear somehow in the sexual fantasies racing through his head. And now he found himself constantly sneaking glances at her. And when he watched porn, he found himself more and more watching MILF and mature categories.
That evening they ate dinner and managed to discuss everything but the topic that was hovering all around them. When dinner was over, Kathleen told Jacon that she was going to his grandmother's house for a quick visit and would be back later.
Claire fixed herself and her daughter a glass of wine and they both sat down on the couch to talk. Claire was on her third glass and feeling good.
Claire was fifty eight and incredibly good looking. She looked like an older version of her daughter. She had put on weight and filled out as she got older, but she wore it extremely well. She had a thick but firm ass and large tits. Her legs were thick but with very nice shape with strong calves and thin ankles. She got plenty of glances when she went to her grandson's wrestling matches in her khaki shorts and sleeveless blouses. She kept her reddish brown hair straight and cut into a bob. She spent a lot of time at the pool and kept tan all year long.
"Ok, dear. What's so important that you needed to come visit, not that I mind of course."
"Mom, it's Jacob. He's got a problem and I'm not sure what to do about it."
"What's the matter with my grandson? Is Jake ok?"
