Chapter 1: Jill Shows Brett the Ropes

Jill Ayers is a feisty bundle of adventurous sexual energy. A suburban mother of three, she stands 5’ 6”, 115 lbs. She has lustrous long brown hair. With three teenagers at home, she nevertheless turns the heads of men, young and old. They all want her. She is separated from her husband and is fine with that.

Jill woke up on a warm July Thursday morning with a plan. To begin with, she was horny. A nice summer day was a perfect time to be fucked. She also wanted to get a ceiling plant holder installed in her bedroom without doing any of the work. She had the perfect boy in mind for both goals. Brett Westlake, a casual friend of her son, was 17, 6’ 2”, 160, with short sandy blonde hair. He was buff and strong, in a wiry strong kind of way. He played on the basketball team and kept himself in shape. He had picked up a lot of handyman skills from his dad. He lived only three blocks away and Jill had hired him for mowing and small tasks for a couple of years now. Brett was sensible, calm and a little shy. He and Jill had always gotten along well and she often teased him in a flirty sort of way because he was a good sport. Jill knew that he often glanced at her furtively, hoping for a glimpse of flesh. She made sure that he got some “accidental” looks at her bra or panties, sometimes some bare boob when she went braless, which was often. She in turn noticed the bulge in his pants when this happened. Recently she had deliberately “stumbled” into him and felt his hard cock on her thigh. But it wasn’t her intention to be a tease. She meant to put out.

Jill had been thinking of Brett in a sexy way for about a year. She especially liked watching him mow when he took his shirt off, moving gracefully around the lawn in his running shorts, which were cut pretty close to his groin. She felt very warm all over when his torso was glistening with sweat. Jill often thought about Brett on those frustrating nights when she had to attend to her needs alone. Those nights were occurring more and more often. She knew it wasn’t her because lots of men were hitting on her all the time. Well, she was fed up with just thinking about it. She would have Brett today. She was hot for the D.

When she finished her morning coffee Jill called Brett and asked if he could take care of the plant holder. He didn’t have any other work projects lined up for that day so he said he’d be over in an hour. Jill had already showered so she changed into her hot pink low rise bikini. Both pieces were a little smaller than her real size. That was on purpose. The bikini wasn’t blatantly indecent but the bottoms showed a well-defined ass and a slight trace of her shaved slit below her prominent mons. The bandeau top properly confined her pert 32A breasts. Jill was proud of her small boobs, which were shapely and highly sensitive. No sagging either. Her nipples did strain against the bandeau fabric, especially when she was aroused. You couldn’t look at her in this bikini and not see her sexual charge. Then she pulled on a very thin low-cut white t-shirt that barely covered her bikini bottom. Brett’s cock would be raring to go as soon as Jill opened the front door. Jill could hardly wait. But she did want that plant holder put in. After that she could think about something else being put in.

Brett arrived on time carrying a small tool bag. He was wearing short cut-offs and a t-shirt. As he entered the house Jill could see that he enjoyed her outfit. Rather, he enjoyed her tanned body. He asked, “How are you, Mrs. Ayers? You’re looking good.” Jill replied, “Oh, Brett, don’t be so formal, it’s Jill to you, after all this time. Let’s sit at the kitchen table and have some coffee.”

He said, “OK, Jill, that sounds good.” Then he sat.

Before she went for the coffee, Jill twirled a 360 degree turn and said, “And thanks for the compliment.” She wanted to make sure he got a good look at her ass, which she thought was pretty fine. After she sat his java in front of him she ruffled his hair and took her seat. “Don’t mind my casual get up, I’m going to go swimming later. The pool looks really nice after you trimmed those weeds last week. I hope you don’t mind me running around like this.”

Brett blushed a little and, with a smile, said, “I like seeing you in a bikini, Mrs., I mean, Jill. The house seems real quiet, where is everyone?”

Jill said, “Well, the big old house is empty right now. My husband took the kids up to Green Bay for a few days to see his parents and family. He’ll drop them off Sunday night. He and I are separated, so the house is a little lonely right now. I’ll get by but I might have to talk you into coming over again to keep me company. Maybe I’ll cook dinner for you.” Brett raised his eyebrows and nodded. Jill then told him about the job she needed done, the placement of a plant holder in the master bedroom ceiling between the king size bed and the sliding glass door. She let him know that she had placed a stool in the room and that she could hand him tools and parts.

They went to the bedroom and Brett started to work, using the stool. Jill stood in front of him and watched. When she tipped her head back to see the ceiling, her t-shirt rode up enough that Brett could see the gentle swell of her mound. He thought he was slick but she knew he was looking. He worked hard to not embarrass himself with a boner but he still sported a semi-woody that could not be hidden. He finished his measurements and Jill handed him his portable drill. The stool wobbled just the slightest bit. She reached out and held his hips to steady him although he was in no danger of falling. His semi-rigid cock was right in front of her and only a few inches from her hands. Her goal was so near and yet so far, for now.

As Brett finished up the work Jill went to her dresser and got a crisp $20 bill. She returned to where Brett was working and put the bill in his jeans pocket. As he got off the stool he thanked her for the money and grinned. She brushed his cheek and said, “Look at you, this job got you dirtier than I thought it would. I have an idea, Brett. Why don’t you shower up in the master bathroom and come swimming with me? I sure don’t need that big pool all to myself and it’d be fun to have a handsome young hunk like you for company. Don’t say no.”

Brett blushed in that cute way of his. He replied, “I’d love that, Jill. I love swimming with hot babes. But I didn’t bring a suit, except my birthday suit!”

Jill called his bluff. “Brett, you bad, bad boy. I bet you think you’re playing truth or dare. I’ll tell you what, if you’ll keep this our little secret, I’ll skinny dip if you will. Join me on the pool deck after you shower and we’ll get to know each other a little better. See ya, stud.” She winked, turned away and walked out of the bedroom. Brett stood in the bedroom agog, almost drooling. Holy shit, had he just scored big time or what? Mrs. Ayers was going to swim naked with him. He couldn’t believe his luck. He’d been hoping to get a glimpse of her in the buff since he was 15. And now it looked like he’d get a lot more than a glimpse. His semi-woody was full blown hard-on. He stripped and headed for the shower, which was going to be a fast one. He didn’t want Jill to have time to change her mind.

Meanwhile, Jill had gone out onto the pool deck with a small cooler of beers. One of her favorite things about the pool was the tall privacy fence. What happened at the pool stayed at the pool. She arranged a lounge chair to face the house. She wanted to see Brett when he came outside. She arranged the other chair to face the pool so they could see each other when seated. She had already discarded het t-shirt. Now she took off her bikini top and sat down. She’d get Brett’s blood stirred up right from the start, although she knew his teen hormones were already dancing. Brett finally appeared, with a towel wrapped around his him, and walked over to his lounge chair. He looked a little dazed. As he sat down, he said, “Wow, Jill, your boobs are gorgeous. I’ve wanted to see them for so long. Just gorgeous.” The bulge in his towel made it clear that he was sincere.

Jill said, “Thanks, baby. They’re small but I get a lot of compliments. Help yourself to a beer. Now there’s two things you have to keep secret. Skinnydipping with me and beer. We don’t want Mrs. Ayers getting into any trouble.”

Brett smiled and said, “My lips are sealed. I can’t believe this is happening to me, not with a beautiful woman like you. I hope I’m not dreaming.”

Jill stood up and said, “Don’t worry, Brett, you can’t dream this good.” Then she turned her back to him and took her bikini bottom off to show off her sweet tanned ass. She even bent forward enough to let him see everything, her rosebud anus and hairless slit. She heard him gasp. Then she turned around with her hands on her hips and asked, “Do you like bald pussy, babe?” Then she stepped forward, “OK, mister, time to get in the water.” As he stood she reached out and tugged the towel off him. He seemed a little startled to be standing naked in front of this woman that he had thought he could never be with except in his wet dreams. Jill took her time admiring his taut young body. What a hunk, she thought. Strong but lithe arms and legs, toned flat abs, full balls lightly covered with curly pubic hair and what looked to her like a 7 inch cut dick. Oh how she wanted that tool inside her, thrusting and squirting. It wouldn’t be long now. “Turn around,” she said. It was her turn to gasp as she ran her eyes over Brett’s pale, tight, well defined ass. Just marvelous. She reached out and slapped one cheek and then took his hand and led him to the pool steps.

As they walked into the warm water, Brett said, “I’ve never seen anything as pretty as your pussy, Jill. I had no idea you shaved. It’s lovely.”

Jill smiled broadly, “I’m glad you like it, baby, I freshened it up just this morning. I woke up thinking that this would be the day I finally got naked with you. I even powdered my little cunt. I’ll let you have a closer look later if you want.” Brett just shook his head, too happy and excited to even talk. Then they actually swam a little. It was a perfect day for it. They each enjoyed watching the other glide through the water and doing a little horseplay that was almost innocent. But the atmosphere was thick with sexual anticipation. Neither doubted how this would end. But hey were patient to let it play out.

After 30 minutes Jill went to the side of the pool on the shallow end and rested, the water line being about half way between her belly button and her peach-like tits. Brett quickly joined her. Jill put one hand on his shoulder and her index finger in the middle of his chest. She looked into his brown eyes and said quietly, “I want to ask you a very personal question, Brett. I hope you choose to answer but you don’t have to.” He nodded his agreement. She went on, “Tell me the truth – are you a virgin?”

Once again Brett blushed deeply and averted his eyes for a moment. Jill loved it when he blushed, he was so cute. Then he looked back at her very seriously and said, “I am, Jill. I act all macho like I’m experienced. I’ve had a couple hand jobs and blow jobs, sort of obligatory after a date, you know? Barely better than wanking off thinking of you. But I haven’t fucked a girl yet.” He blushed again and turned his head.

Jill gently turned his head back so she could look him in the eyes and flashed him a big grin. “Baby, let’s change that today. I’ve wanted you to fuck me for a year. I’ve thought about it a million times. Because you were so young I just didn’t know how to seduce you without maybe scaring you off or maybe you telling someone. But I think you’re mature enough now and I think I make you horny. I know you make me really hot and really wet between my legs. I want to be your first woman and feel your strong manly cock deep inside my pussy, pounding me and stretching me. The good thing about having someone like me for your first is that I know what I’m doing and you don’t have to worry about hurting me or making me bleed. And I won’t get pregnant, that’s guaranteed. Just nod if you want this too and don’t feel pressured or like you’re being taken advantage of.”

Brett nodded but had to speak also, “Oh my God, Jill, I want you so bad it almost hurts. I’ve wanted to fuck you for at least a year too. I always think of you when I jack off and it’s great. Right now I just want to fuck, fuck, fuck you until my dick falls off! I am so fucking lucky that you want me. I want you right now more than anything”