Hi, I've disabled comments. This is meant to be fun, and the shitty comments and trolling are tedious. I hope that you enjoy it.
Jill looked out of her bedroom window. She had heard the gate to her driveway opening. Jack, the son of her best friends Su and Tom, had arrived to cut her grass.
Jill was a fifty-five-year-old widow, living alone on the outskirts of a small college town. Her husband Bob had passed away three years ago.
Jill was only now beginning to pick up her life following the death of her husband. God knows what would have happened to her without the support of her friends and their son Jack. Su had been there for her, making sure that she ate properly and looked after herself, and finally persuaded her to get out into the community and start to live again.
She had turned down an opportunity to meet up with an old boyfriend from her pre-marital days. Bob had also lost his mate and had suggested that they see if they could revive their previous relationship. She had thanked him for his offer but had told him that she was not ready to move in that direction.
Jill was a voluptuous lady. Her body had stood up well to the test of time, no doubt aided by not bearing children. She had remained faithful to her husband throughout their married life, although many men had shown interest in her over the years. She had enjoyed the attention but had consistently declined.
Tom and his son Jack had looked after all the physical work around her house and considerable property since Bob's death. Young Jack came over several times a week to do her lawn and garden or shovel snow in the winter. Despite the fact he was attending the local college and had part-time job evenings and weekends.
Jill had noticed unhappiness or possible depression in Jack over the last six months, which was unusual for such an outgoing young man. She suspected it had to do with women. His mother, Su, had indicated that he never appeared to have a steady girlfriend.
He was a good-looking young man, well built with a friendly open face. Jill wondered why girls were not chasing after him. She suspected that she would have been after him when she had been 19 or so. He was tight and muscular, the bulging thighs and tight butt of a young man who had enjoyed sports all his life. She smiled at the slight twinge in her pussy, as she watched him get out of his car.
I headed for the backyard to retrieve the lawnmower as Jill pulled on a pair of tight pants and tucked her breasts into a tight-fitting top. She smiled in the mirror as she applied a touch of lipstick. Here she was trying to look sexy for a young man she had known all her life.
Jill heard Jack finishing up. She stepped out to the rear terrace to greet him. He smiled at her and waved. It was a warm summer evening, and he had worked up a sweat; his tee-shirt was moulded to his upper chest. Jill took in her breath as she felt another surge of warmth in her pussy. 'What is wrong with me,' she wondered.
"Jill, you look great". My eyes ran unashamedly up and down her body. We had always had an open and frank relationship. We were always direct in our exchanges and could say exactly what we felt. The comment was not meant to be a pass at her, just an expression of my thoughts.
"Jack, you have worked hard. Let's have a glass of wine? She smiled. But she did feel good at his compliment. She glanced back as she left to get the wine to see him looking at her ass and legs. She swayed her hips a little, letting him know that she knew that he was looking at her butt.
We sat on the back patio, exchanging chat and stories, much as they had done for many years.
Jill asked, "How is your love life? I never hear much about your girlfriends. Are you too shy to tell me about them?"
"I am afraid there is not much to tell Jill. I don't do very well with the ladies. I have dated a few, but it never seems to get anywhere."
This confirmed to Jill that whatever his problems were, they originated with a girl or girls. "I can't understand that Jack, you are a great looking guy, play sports, excellent student and well-liked by everyone I know. Tell me about it."
"Oh, I'm not sure what to tell you. When things start getting a little more personal with a girl, that's when they start to lose interest," I said, not looking directly at her.
"Are we talking matters of sex here? Some women don't want a guy to move too fast. Are you being too forceful? Maybe just take it slower is all that you need to do."
"Oh no, I don't rush things, and I usually do get to first base," I said.
Jill looked at him closely, "You mean they let you intimately touch them."
Jack was very defensive, "Yes, I get to touch them alright."
Jill said, "And then?"
I didn't look at her when I murmured in a low voice, "It's down to my size."
My reply completely caught Jill off guard. She thought, my god, the poor soul must have a tiny penis; no wonder he looks so down and depressed.
"Jack, you must know that a lot of guys have that problem; it's not the size that matters; it's the technique that's so important. Have you talked to someone about it?"
"I can't bring myself to talk to anyone, except now with you,"
"What about your Dad? This may run in the family?"
I smiled, "Dad's never even told me about the birds and the bees. But, Jill, I have got a massive cock. I was in the toilet in a bar once with dad. I saw his cock. My cock is twice the size of dad's. When any of my girlfriends see or touch my cock that scares them off. "That would split me in two. That's too big for me". I have heard it all; I wish it weren't so big, then I'm sure that I'd be having an exciting sex life."
Jill couldn't believe what she was hearing. Her pussy was getting so wet. She glanced at Jack's groin. A massive bulge was forming in Jack's trousers.
The discussion was turning both of them on. Jack could see Jill's nipples pushing through the cloth of the top while she squirmed in her chair. Jill noticed movement in his tight shorts, a bulge forming down along the inside of his thigh.
"Don't let this worry you too much. You will soon find a pretty girl who likes a big cock, and a lot of women love a big cock then your problem will disappear."
I said, "Did you have sex before you got married?"
It was Jill's turn to be defensive. She started to deny it but felt that she should be open with him in return and said, "Yes, I did have several affairs before I married Bob. Why do you ask?"
"Well, did any of your lovers have problems like I am having?"
"Not exactly, but first times are never terribly satisfying at that age. It takes a while to become relaxed and comfortable with sex. There was a lot of messing around, and even then, the foreplay was usually better than the sex. One or two guys did get off too quickly, although they were in my pussy when they came."
Jill was thinking about a guy with a massive cock, though Jack's looked thicker and longer. Who was married, but he had given her the best fucks of her life. She still fantasised about his massive cock when she gave herself relief.
"Jack, I think we should let this be for now. However, I am glad that you were able to talk about it with me, and maybe that will help."
"Jill, it was a relief to discuss it with you. I felt so comfortable telling you about my problem instead of having it in my mind all the time. Thank you for that. Can we talk about it again some time?"
They stood up, and Jill put her arms around him and kissed him softly on the cheek, "Of course, Jack, if it helps, then I am happy to chat about it anytime with you."
I could barely keep my hands still as she pressed her breasts against him. Finally, I allowed my hard cock to brush her hip and felt her hesitate. I knew that she had thought it when she returned the pressure. Then I left.
Jill tossed around sleepless that night. She could not forget the exchange with Jack. She was very aroused at the thought of his problems. Ideas flowed through her mind like crazy. Maybe a hand job to get him off. Then he would know that he could get some sexual pleasure. Maybe a blow job, she was sure that she could deep throat his monster cock, she did it often with her married lover. Perhaps she could help him become a more accomplished lover. Maybe she could seduce him. Her cunt was dripping now.
Her slit was slippery and wet as she made little circles around her clit. She slid a finger up inside her pussy and clenched her legs tight around it. She got off for the first time in a long while, prompted by visions of Jack's massive cock buried in her.
I showered when I got home and wanked myself off with the thought of Jill's body wrapped around him. She had always looked pretty. And in recent years, he had often imagined being in bed with her. But now, she seemed more available, and he thought of little else for days.
Later that same week, Jill called and asked me if he could come over for a short while to check out her laptop.
She was wearing a tight top and a push-up bra which made her tits look massive, and her short skirt. Her hair was beautiful, her eyes were bright, and her lips glistened. Jack's hands became hot at the sight of her. He wanted to touch her. Jill showed Jack her laptop. She had forty windows open in her browser. Jack closed them then restarted her computer. All was good.
She invited him into the living room, and they sat side by side on the sofa. But then, Jill got to the point.
"I have been thinking about your problem. And to be honest, our chat excited and aroused me. So straight out, I would like to try and help you. You might overcome it by practising with me. There would not be any pressure for you to be anxious about pleasing me. And I would love to show you some techniques that arouse women."
The thought that Jill had any interest in him sexually had only recently entered his mind, and even then as pure fantasy. "God, Jill, are you sure? I would love it." I reached for her, but she smiled and pushed him back.
