The Confession Ch. 02

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Jack and Kelly struggle with his admission.
1.8k words
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Part 2 of the 16 part series

Updated 09/22/2022
Created 02/02/2005
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thehumpman
thehumpman
3,019 Followers

Jack spent most of his week following the weekend away from his good friend Kevin, if he did not have practice he devoted his time to the computer in his room. He surfed the net trying to find stories of young men seducing older women, yet none of those really seemed very realistic.

Jack was also very relieved that she did not tell anyone about his little confession in the car last Sunday. He could only imagine what Bill what do to him, Kevin would probably kick his ass, and he would be humiliated at home or at school if anyone knew.

The only conclusion he could make after trying to figure out how seduce Kelly was that he either had to worship her from afar or get her out of his entirely. He had a lot of various pictures of her on his hard drive that he brought up. He looked through the various folders of pictures that he had taken over the last few years. These provided his fantasy materials a good many times while he was alone in his room at night.

With his mother downstairs making supper he opened a folder called "Fun at Kevin's Pool". He was able to sneak a lot of great pictures of Kelly in her conservative blue two piece swimsuit. Kevin undid his jeans and pulled his cock out of his boxer shorts gently fondling hit to get it erect. He leaned back in his chair and closed his eyes mentally imagining Kelly in the blue two piece swimsuit. In his mind his fantasy of his best friend's mom started to play out.

He pictured himself and Kelly being alone by the pool, she was laying on her stomach on her lounge sunning herself. Jack muttered something stupid about looking for Kevin which she replied he's not home. Jack turned to leave when she reached up and grabbed his hand beckoning him to stay.

"Would you rub some lotion on my back Jack." She said seductively.

"Uh okay." He replies.

He dreams he is rubbing the lotion into her shoulders, massaging it in knowing he is doing a good job when he hears a deep moan. His hands in his fantasy go from her shoulders down to her lower to her shoulder blades. His breathing is now in short breaths as the he can almost feel the softness of her skin.

Jack begins stroking his cock faster and faster now; he allows his hands to roam further down her back to her swimsuit clad ass. He gently starts to pull it down the bottoms and……..

"Jack get washed up for supper." His mother calls up to him from the kitchen.

"Oh shit." He moans as he shoots a powerful load all over his keyboard.

"JACK SUPPER!" his mother yelled this time.

"I'm coming mom." He hollered.

Jack grabbed some tissue and cleaned up the mess he made on the keyboard, he hated when he would cum all over like this. He was good about cleaning it up because he did not want his mother to find out. Jack shut his computer down and went to the bathroom to wash up for supper. Later on tonight he would be back on his computer, with his pictures of Kelly Welch and his fantasies of her.

Kelly too was on her computer at her house as well, Kevin was busy doing homework and Bill was working late. She too was searching for information through many different websites on how to deal with her smitten young admirer. She found information that was too clinical for her to understand or explain, she found a lot of motherly type advice that could be considered to be old fashioned and she found the perverted milf stories.

She did not want to embarrass Jack, so she felt that it was a good idea not to tell Bill about what happened. She definitely did not want to tell Kevin, her son and Jack had been friends for so many years. Kelly did not want to tell Jack's parents either, so it was really up to her to nip this in the bud and get him to look for girls his own age.

Kelly read a few of the perverted milf stories she had found, they all sounded so unbelievable to be true. Could anyone possibly believe stories of older women seducing young me she thought? How about the opposite stories where a younger man seduces an under sex housewife? She found Jack to be an attractive young man for his age yet she really could not picture herself having sex with him.

Kelly was surprised to find that she was getting a little wetness on her underwear, the fact that a young man did find her attractive was a little exciting to her. She would never really come out and admit that she found this exciting; she masturbated a few times to the thought of this herself. She was feeling the urge to have an orgasm with the more stories she read while at the computer.

Dinner was in the oven and Kevin was busy with homework, so she erased her history on the computer. She got up from the desk and headed up stairs to her bedroom, Kelly lay down on her bed and she slowly unbuttoned her blouse, and then unhooked her bra. She undid her jeans and slid them down her legs; she put her hand inside her panties and rubbed her pussy.

She stuck a couple of her fingers in her wet pussy and began to finger fuck herself on her bed. Her thumb was gently brushing her sensitive clit as she closed her eyes and thought of when she was younger. Bill had taken her out for dinner and a movie, after the movie he took her to Lookout Hill a popular make out spot.

Bill got her in the back seat of his car and the two of them were kissing passionately steaming up the windows. Bill had her blouse unbuttoned and he was clumsily trying to unhook her bra. He finally got it unhooked and he roughly fondled her small tits like most teenage boys with no experience do.

Bill managed to get his hand up her skirt and inside her panties; he knew nothing of stimulation and began immediately to finger fuck her young pussy. She vividly remembered that night in her memories, despite Bill's inexperience this was the night Bill and her lost their virginity.

"Kelly I have a condom." Bill whispered in her ear.

"Oh god Bill." She whispered back. "I love you."

"I love you too Kelly." He said "I really want to be with you right now."

"I think I'm ready Bill." She said.

With that invitation Bill reached up her skirt with both hands and slid her panties down and off. He clumsily undid his pants and pulled out his cock, he unwrapped the condom and quickly slid it on. Kelly instinctively spread her legs and hiked her skirt up, Bill nervously got between them. The combination of the condom's lubrication and her own wetness allowed his cock to break her hymen and slide into her pussy.

"OOOOhhhhhhh!" she moaned. "Just be gentle Bill, it hurts a little."

"I love you Kelly, I won't hurt you." He said softly.

Bill took his time and was gentle; he made nothing but slow gentle thrusts despite his excitement wanting to go faster. Kelly fell in love with him even more for being gentle with him, once her pussy got accustomed to the foreign invader she wanted more.

"Faster now Bill, oh yes faster baby." She moaned.

This was all Bill needed to hear he pounded his cock in and out of her virgin cunt faster now. He could feel her nails dig into his back and he could feel her body tense from time to time under him. Her loud moans were driving him mad with an animal lust; he had never felt such power as he brought his virgin girlfriend to orgasm.

"Oh yes Bill yes YES YES YES YES." She was screaming as she had an intense orgasm.

"Yes babe I'm going to cum." He said "AAAAAAAAAAHHHHHHHHHH!"

Bill lay on top of her as his cock spewed over and over again in the condom; he laid there and kissed his love. Kelly's body now tensed up on the bed and her hips bucked up high as she brought herself to orgasm over her memory. As she lay on the bed with her eyes closed, relaxing from the intense climax she had just had. She again pictured herself in the back seat of Bill's first car, only this time she looked up from the back seat and it was not a young Bill looking down her. She saw her son's best friend, her new admirer staring down at her.

Kelly opened her eyes quickly; she was brought back to the reality that she had to get this situation with Jack over with and out of her mind.

"Jack." She said aloud.

Kelly freshened up and got down to the kitchen where her son was already seated at his seat for dinner. She got the casserole dish out of the over and put some on two plates for her and her son. She got another plate and put some more on it, she wrapped the plate in foil turned the oven down to keep it warm for Bill.

She brought the two plates over to the table and handed one to Kevin, she took her seat and sat down to eat. They made the usual mother son conversation during the meal and finally she asked him about Jack.

"Where has Jack been lately? She asked.

"He said he has been busy, I don't know he has acted a little strange since the weekend." Kevin explained.

"Has he mentioned why he is acting strange?" she asked

"No, he is probably just nervous with the regional title game coming up." He said "We have to go out of town and play next weekend."

"I almost forgot I will be one of the chaperones for the game." She said. "Too bad it is the same weekend of your Dad's annual sales convention. I will have to tape it for him."

"Is it okay if I ask Jack if he wants to room with us at the motel?" Kevin asked.

"Sure I guess." His mom replied. "I thought his parents are coming?"

"No his Mom and Dad have to go out of town for a wedding the same weekend." Kevin explained.

Kelly knew now she only had a couple of weeks to have Jack learn that a relationship between the older, married, mother of his best friend was not possible. If she could not it would make for a tense weekend staying in a motel room together for a night, even if her son was going to be there too.

thehumpman
thehumpman
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