My Busty Neighbour

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May 16, 2023 // By:analsex // No Comment

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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; Escort Sarıyer 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? Silivri escort bayan I would love it.” I reached for her, but she smiled and pushed him back.

She said, “Now there you are, going for the girl too quickly. Making love should not be a race to the finish. Most women, including myself, enjoy the seduction part. Every move should be only a lead-in to another move. And you should wait for her to respond. First, let me touch you and see if we can get past the first hurdle. Then, think of me as a teacher and forget about getting into my panties.”

Jill was not as objective as she sounded; her blood was racing, and her nipples were hard. But she wanted to keep him calm.

Jill moved closer to Jack on the sofa. She could see his stiff shaft lying along the inside of his trouser leg. She said, “I’m going to touch you now.”

I could barely breathe as I said, “I am hard already.”

Jill leaned into me, allowing one breast to rub on my arm. She let her open hand rest on his bulging shaft. She could feel the heat building in her pussy, as she said, “Let’s not worry what will happen. If you cum it’s okay, nothing lost; you won’t be putting it in me anyway. And I imagine that you will recover quickly enough to try again.”

I said, “I can get hard fast.”

She slowly closed her fingers around the shaft through his pants. Her eyes focused on his as her hand began to stroke him slowly. Finally, she felt him start to throb and lifted her hand. I pleaded, “Don’t stop, Jill.”

“Close your eyes, Jack, think of something else for a while. We want to stretch this out as long as we can.”

With that, she unhooked my belt and pulled down my zipper. She felt me tense as she gently stroked the outline of my cock through my shorts and then quickly pulled the band of his shorts down to allow my cock to pop out. She wound her fingers around my shaft carefully, squeezing it just below the bulbous head. She felt me throb again and released me. Jill was amazed at the monster cock Jack had. If she had been a young virgin, she would have worried about taking it in her tight pussy. She knew then that she wanted it inside her.

She considered herself an expert in hand jobs but had never played this role before. So it might be her and not he who got off first.

“Fuck Jill, that feels so good.”

I lifted my butt as Jill tugged my shorts down, freeing my entire stiff cock and big balls.

“It is exhilarating for me as well,” whispered Jill, “you have a very beautiful cock.”

The monster was so thick there was a two-inch gap between her fingers. My balls were as big as any of the enormous hen’s eggs she had ever seen. I slid one hand inside her top. I cupped her massive left tit. I felt the hardness of her nipple. Jill bit her lip to contain her excitement,

She circled two fingers just below the burgeoning knob and stroked him slowly with the other hand. She remained calm and gave no sign of her inner turmoil. She wanted to suck it but felt that should come later.

“Jill, I am close? Should I cum?”

She pulled her hand away and said, “We are doing well. Settle down and relax and see if we can hold back a little more.”

She sat back and took off her top. Her massive tits looked amazing. There was hardly any sag at all. Instead, her nipples were big and hard. She also pulled her panties off but kept her short skirt on. She wanted to excite him more, but her pussy might be too much to show him now.

“Don’t cum now, Jack. We have gone further than I dreamed we could, but nothing lost if you do cum. We can start again. You have a gorgeous cock. I love it. The size of it so arouses me. You are very desirable. Never forget that, Jack.”

She settled back in beside me, both breasts pressing my arm and chest. Her hand slipped quickly around my cock, and she whispered, “Touch me now, touch my pussy, feel and play with it. You must get to know it and don’t think about getting your cock in it. Just feel and play with it.”

My heart was racing, my fingers trembling as I moved my hand up under her skirt, along the silky skin of her inner thighs and finally to her mound. I thought only of her pussy and not my cock as I felt her smooth mound with two fingers. She opened her legs slightly, and I pushed two fingers inside her slit.

“Now my nipples, women loved to have their nipples sucked as you play with their pussy, make sure you do that each time. Oh, my big boy, your lips are hot and wet.” Her hand started to move on his cock, stroking him gently.

I lifted the hem of her skirt around her waist, but It was too much for me. I then shot my load as Jill wanked me and milked all my cum out of my cock.

We had pushed too close to the edge, and with a sudden jolt, I closed my hand around hers and blew my load. We kissed lovingly, a full open-mouthed tongue-sucking kiss as my cum spurted out.

“Fuck Jill, see what I mean? I thought I had it, and then suddenly just lost it,”

“Don’t worry about that. We jumped some hurdles before you Topkapı escort got off. When you come before your partner, you must perform. You have to consider the lady. She would want to get off, and I certainly do. Give me your hand, and I will show you how to pleasure a woman with your fingers.”

She settled back on the sofa sideways to me, spread her legs and pulled his head down to her tits. “You should always start on the nipples, kiss and suck them lightly.”

I found a nipple with my lips and sucked on it.

“Use your tongue, baby; run around the nipple with your tongue. Good, feel good, suck now. But, ah, the feeling goes right to my pussy, makes it tingle and get wet. The other one now.”

“You should be good for a while. You just got off, so you can probably feel me without losing it,” she whispered hopefully.

She took my hand and guided it to her mound. My fingers toyed with the hairs on her bush. “Yes, yes, play with the pussy, rub it with your fingertips. Good, do you feel my legs soften and part? That’s an invitation. Gently Jack, use your fingers to tease my clit. You have already made it wet and slick. No, don’t thrust them in, slow and easy, along my slit bottom to top. Yes, now use one finger to tease my clit. Just make soft little circles around it. Be easy with it, feel it swelling, oh goodness.”

I could sense Jill slowly surrendering herself to my fingers. I felt in control now, feeling her rotate her hips in response to each move. Finally, she pressed my finger into her slit, and I felt her pussy close and tighten on it.

I bent down and slurped a hard nipple into my mouth. Jill gasped and pulled my head tighter to her, her hips now writhing, her legs closing. I instinctively began stroking and then slipped a second finger in as she spread again.

“Yes, yes, yes,” she moaned as her hips began to drive back and forth on his two fingers now buried deep in her pussy.

For the first time in his life, I experienced the thrill of getting a woman off. It was not lost on me; I realised that touching and kissing her had produced such an erotic result.

Still pressing her hands on top of mine, she slowly opened her legs again. I continued to rub her mound and finger her. Her pussy lips were swollen and trembling. I looked in wonder at this gorgeous woman, her body still trembling.

She reached down and found my cock, stiff as a rod once more. She closed her hands around it and said, “Fuck, look what I have found, ready for more so quickly. But, Jack, do it now, or we may never have the courage to do it.”

With that, she lay back in the corner of the sofa and pulled me up, her tits bare and skirt bunched up around her hips. I fumbled around, suddenly excited again, jabbing at her pussy until she whispered, “Slow down, it’s not going anywhere, take a deep breath, let me show you.”

I slowed down and raised myself over her, supporting myself on extended arms placed on each side of her head. She had room to reach down and guide the bulbous head of my cock to her long sex slit.

“Easy Jack, just go in slowly, try not to think of where it is. That’s right, baby, nice and slow, you feel great, and you feel wonderful in me. Now lay down on me, cover me, feel my jugs against your chest, and make love to me.”

I closed my eyes, my mind now only on the woman beneath him, the feel of her body pressing against mine, her legs slowly encircling my body, trapping me inside the hot wet warmth of her pussy.

I began to stroke her slowly at first but quickly lost it. The natural need to plant my seed in a woman took over. It did not last long. I jammed my cock deep in her and let loose. My legs stiffened, my toes curled, my hands pulled her up against my body, and with some slow grinding strokes, I experienced total relief for the first time in his life.

We lay there for a while, her hands holding my ass cheeks, my mouth on her neck.

I finally lifted off of her and smiled down at her. “Oh, Jill, that was so great.”

Jill said, “No thanks needed, I wanted that as much as you. But we can’t make a habit of it, can we? People would soon find out, and it would not do anybody any good, including your parents.”

“Maybe we could have a few more classes and tips,”

“We are all sticky; you can’t go home like that. Did you ever shower with a woman?” she smiled.

We jumped up and ripped off our remaining clothes, and raced to the shower. Soon they were in a cascade of warm water, taking turns with the soap. The young stud was erect once more. Jill moved behind him, her oiled tits crushed against his back, her arms around him soaping his cock.

Jill whispered, “One more lesson today. I love oral sex, and you should learn about it. So today I will give, and you will receive, but I expect to be the receiver the next time class is called.” She turned me around, facing her, my body protecting her from the shower stream.

She dragged her tits down my body, looking up at me as she did so. I was trembling already. This would not take long. She ran her tongue around the head of his cock. She closed her fingers tightly just below my bulbous head before slipping her lips over and around it. She looked up at me again. I was standing rigid with my eyes closed tight. “Just let go when you want, baby. I’ll look after things I want you to enjoy.”

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