So the months of summer were quickly slipping away. Jimmy and Joanne's relationship continued on two levels: as teacher and student, and as boss and employee. Joanne had partially put the brakes on her young lover. Jimmy would be content to have sex every day with his buxom middle-aged neighbor, but Joanne finally had to admit that he was wearing her out, literally. As much as she enjoyed sex with him, his youthful exuberance, combined with a girthy, nine-inch cock (she measured it), had her walking with a limp periodically.

In fact, Jimmy's mother, Fran, had commented on her obvious impairment when she watched Joanne walk stiffly to collect her mail.

"Are you okay, Joanne? Did you hurt yourself? You look like you are in pain."

"Oh, I'll be fine. It's an old gymnastics injury. I was doing some yoga and must have strained something. I just need to take an Aleve. It will go away if I just lay off exercising for a while." And keep your son's cock away from me.

"Well, if you need something stronger, I have some prescription meds...Vicodin...left over from oral surgery. Let me know. Bill and I are going to our cabin this weekend. I'll tell Jimmy where they are in case you want them.

"Thanks, Fran. I may take you up on that. How long will you be gone?"

"A couple of nights. Jimmy can survive that long on his own."

"Well, if you'd like, I'd be willing to feed him dinner. I would be happy to have the company. I've got a couple of steaks in the freezer I need to use. It would be better than a hot dog or whatever teenagers eat."

"I'm sure he'd like that. I'll mention it to him."

Immediately, Joanne's brain started planning. Jimmy had progressed in his lessons to the point where he rarely had a premature ejaculation, partially due to practice and partially to the frequency of their fucking. Their sessions were strictly on Joanne's terms, and she had slowed their frequency out of fear that he was going to wear out some of her body parts. Jimmy had the energy of a sixteen-year-old, but now with the stamina of a seasoned pro. And because his cock was so large, she felt like she was getting serviced by a porn star at times. He was a good student–almost too good.

But the chance to spend an evening or possibly an entire night with him caused moisture to form between her thighs. So far, their couplings had been hastily arranged around his job and in between chores. Joanne feared his mother would become suspicious if he was gone for two hours to simply mow a patch of grass in her backyard. Fucking during the day posed the inherent risk that Fran or another nosy neighbor might stop by and wonder where everyone was while they were sweating and grunting on her king-sized bed.

They even had a couple of sessions in her living room and kitchen when temptations and libidos had suddenly overtaken common sense. The possibility of getting caught was part of the thrill. When Jimmy fucked her on the kitchen table in front of a window to her side street, Joanne's orgasm was beyond belief.

But a candlelight dinner and maybe even a shower together after a slow and leisurely romp appealed to the busty neighbor. It would certainly add an element of romance that had been missing during their passionate spur-of-the-moment fucks.

Joanne imagined a night of passion: fucking and sleeping, and then waking up and fucking some more. She couldn't wait for the weekend.

When Jimmy's mother told him that they'd be gone and that Joanne offered to fix him dinner, his head spun at the possibilities. This would be like a date. His teenage libido, combined with recent events, had him in a frenzy. While he was not exactly writing Joanne's name all over his notebook, as teenagers often do, he was fantasizing about a full-blown relationship with his voluptuous neighbor.

"Jimmy! Get those thoughts out of your brain. I'm old enough to be your mother. This is not permanent. This is a summer fling, Honey, and it is not for publication." Joanne feared his teenage crush might doom them at some point. She wanted to enjoy the relationship as much as possible, but not if it risked everything else. What would people say?

Fran, Jimmy's mother, did have her suspicions about her son's enthusiasm to be working constantly for Joanne, but he reassured her it was just business.

"She's actually a taskmaster, but she's paying me well, so I don't mind. I'm saving for college."

Who could argue with that?

Friday finally arrived, and Joanne was busy prepping for the evening. She carefully selected her clothing and made sure she had everything she needed for dinner. She knew Jimmy was a big eater, not including his munching on her trimmed pussy, and so she made sure she had everything covered. They would start with oysters on the half shell (eating them makes me so horny, she had once admitted to a friend), followed by steak and salad for the main course, and for dessert, a delicious chocolate cake. And finally, for a last course, slow, unhurried sex on silk sheets.

She had told Jimmy to show up around six.

She had planned some time to relax following dinner. It would be foreplay, in a sense. Her large-screen TV was set to show a streaming video she had saved featuring a beautiful middle-aged woman seducing a young friend of her son. The scene was shot through a soft filter that gave everything a dreamlike quality. The muscular young actor so reminded her of Jimmy, although Jimmy's cock was undeniably larger.

When the doorbell rang, she excitedly glanced over her preparations and opened the door to a smiling teen dressed in neatly pressed chinos and a Hawaiian shirt with a bold palm tree design. Joanne smiled, and once Jimmy was inside, she closed the door and kissed him. She was wearing a low-cut blouse and slacks that showed off her beautiful ass.

"You look very handsome, Honey. C'mon in. Let's sit outside and have a drink before it cools off. I'm having wine, but I have soda, non-alcoholic beer, or sparkling water for you. Nothing illegal, Sweetie. Sorry. Besides, I want you unimpaired for what I have planned later."

She winked and licked her lips temptingly. Jimmy's brain–and his pants–were bursting with anticipation.

She led the way, her stiletto heels clicking on the tile floor. She had the oysters on ice and ready to serve, as well as a variety of drinks for Jimmy and chilled wine for herself.

Jimmy had never tried fresh oysters before, and the way Joanne sensuously ate them was not lost on him. When they were gone, the couple slipped inside, and Joanne finished preparing what turned out to be a fabulous meal.

"God, this steak is fantastic, Joanne. You are a great cook, along with everything else you do."

"I'm not sure what 'everything else' might be, but I'll take it as a compliment. We need to relax after all that food. Do you mind if we watch a little TV? I picked out something special for us."

Together they snuggled on the couch, and Joanne started the video she had saved. At first, Jimmy was unsure what kind of movie was playing. The credits seemed innocent enough, but like all porn, it was only minutes before two naked bodies were writhing in a passionate embrace. The scene was not as raw as most of what he jacked off to late at night. The female actress was attractive, but clearly an older model, and the man who was currently eating with her was muscular and handsome, yet with a youthful face. He looked like a hung teenager.

Regardless, Jimmy soon sported a raging erection. Joanne lightly rubbed him through his pants but made no effort to go beyond that. Jimmy casually fondled her big breasts that pressed into him.

"Notice there are no tattoos, no choking, no slapping asses. This is a step above the raw, wham-bam style porn. It's almost romantic. I can enjoy this kind of porn. Lots of kissing and teasing. And notice that her boobs are real. She's busty but not a circus attraction. No balloon implants for her."

Eventually, the couple got around to fucking, and even that was slow and deliberate. They tried various positions, taking breaks for the woman to fellate and kiss her lover from time to time. And then this happened.

"This part is hot. Watch what she does."

The young man was behind her, fucking her doggie style with lots of close-ups of his large cock sliding in and out of her clinging labia, when the woman turned her head with a wry smile and moaned a suggestion. Joanne turned up the volume.

"Would you like to fuck my ass? I'm a virgin there, at least no cock has been there before. I've been saving it for you."

"Really? You want me in your ass? Yes. If that's what you'd like."

She reached for something off-screen and handed him a flip-cap tube.

"First, put this on my ass and your cock. Don't be shy. Use lots. You're a big boy."

He applied a clear gel as instructed and spread it with his fingers over both body parts, and then placed the head of his penis in the tiny opening of her ass. He pressed his hips forward, but his cock only slid up between her cheeks for several tries.

She reached behind and gripped his shaft and rubbed the crown of his cock against her anus before slowly pulling him forward and pressing her hips back until the crown finally disappeared inside her ass. The tight sphincter resisted at first, and then all of a sudden, he was in her.

"Ungh," she grunted at the initial penetration, but then she relaxed and, eyes closed, concentrated on the mix of pain and pleasure his cock provided.

"Wow, that's different. No, no...it's good, Sweetie. Yes, just like that. You fuck me so good."

Joanne was smiling and squeezing Jimmy tightly in her excitement.

"What do you think, Jimmy? Isn't that sexy? God, it turns me on to watch this. Is that something you would like–fucking a woman in the ass, Honey? I'm not sure if I'd like it or not, but never say never."

Jimmy was unsure how to respond.

"Um, yeah. I guess I never really thought about it. If that's something you want to try...sure."

"We'll see. In the meantime, let's just fool around a bit. Okay?"

She stroked his rock-hard cock through his pants and then unzipped him and pulled out his thick cock after a struggle to get it through the fly. Jimmy was fondling her big breasts through her blouse and kissing her full lips, before she stopped and smiled at him.

"You know I love your big cock, Jimmy. Tonight, we are going to take our time and enjoy each other. Summer is winding down, and this experiment may have to stop. No, don't say anything. I can't make any promises. I will always cherish my time with you, teaching you, teasing you, and yes, even fucking you. You have become a wonderful lover. And for tonight, I was thinking that maybe you would want to spend the night with me? You'll have to leave early in the morning before the sun comes up, so no one sees you leaving. Would you like to do that? That gives us more time for whatever comes up, like this big sausage in my hand."

She smiled and shook his cock to make a point.

"I'd love to stay here tonight. But I don't see why this has to end. You know I love you, Joanne. It's more than sex."

"Oh, Honey. That's so sweet. We'll talk about it later, but for now, let's go to the bedroom and get naked so I can see if this big bat will still fit in me."

Once in the bedroom, Joanne removed her slacks and blouse but retained her white support bra and panties. Jimmy was down to a smile and nothing else in seconds. They climbed aboard the bed and lay side by side, kissing. She knew Jimmy had a thing for bras stuffed with big tits.

"We're in no hurry, Honey. We have most of the night, and if I know you, you'll probably not sleep much. Which means I won't either. I'll be honest–I want you to make me cum with your tongue, and then later you can fill me with your fertile seed. I bet your balls are full. We haven't made love in almost a week."

Jimmy didn't bother telling Joanne that he emptied his load almost every night, sometimes more than once, both for pleasure and as insurance he wouldn't cum prematurely in case he got the opportunity with her. In fact, earlier in the summer, Joanne had encouraged him to masturbate for that very reason.

After a long period of fondling each other, Joanne removed the rest of her clothing and lay on her back.

"Okay, lover boy. Let's see what you can do with that long tongue of yours. Oooh, yes. That's a great start. That little man in the canoe loves a good licking. Wait a sec."

Joanne slid a pillow under her hips and pulled her knees back so that she was bent almost double.

"That's what years of gymnastics and yoga will do–make men happy. How's the view, Sweetie?"

Jimmy quietly attacked the entire area between Joanne's butt cheeks: her little pink star, her labia, and, of course, her clitoris. Joanne helped by rubbing her little nub in tight circles whenever he was working on other areas.

"Oh, fuck, Jimmy. You know what I like, don't you?

Jimmy steadily used his tongue, lips, and fingers to please his neighbor, and she responded with vivid descriptions not suitable for dinner conversation. She ground her hips in tight circles and pressed Jimmy's face into her groin.

"Oh, Honey. Eat my pussy. You're going to make me cum soon. I feel a big one. God, you are getting your tongue so deep in me, and then when you put your finger in my ass, it gets me to another level. Don't stop, Sweetie. Yes, yes, yes, YES!"

Jimmy increased his efforts with her encouragement, and soon it paid off. He first felt a jerk of her hips followed by several aftershocks, and then a flood gushed into his mouth and onto his face. He continued his ministrations and even intensified them until Joanne finally quit screaming and begged him to stop.

Jimmy slid up and kissed her mouth with his glazed face and lips.

"I love the way you taste, Joanne. If somebody had told me I'd love the taste of pussy, I would have said, 'You're crazy.' But now I know. Maybe it's just you. You are the only one I've tasted."

"I can't say all women taste the same, Honey. But I'm guessing we're pretty similar. I've only tasted one other woman...long story...so I'm no expert. When I'm old and gray, and you've done a survey, you can tell me if I'm right. That was wonderful. Let's cuddle for a while and recharge our batteries before we go to phase two."

They lay in each other's arms and kissed lightly. Joanne stroked her lover gently and worked her lips up and down his body. After a while, she stopped and grabbed a scarf from a chair next to her bed.

"Okay, Honey. A little kinkiness I want to try. Trust me. This will be fun."

She ordered Jimmy to set up.

"First, I'm going to blindfold you. That way, your other senses will be intensified." Joanne tied a bandana over his eyes and had him lie face down on the silk sheets. She used her body as an extra pair of hands and rubbed her breasts over his entire body before touching him with her hands. With small amounts of body oil, she gently rubbed his muscular back and legs, paying special attention to his buttocks. When he coaxed him to turn over, his cock was at half-mast and straining to overcome gravity.

"You need some help, I see. Let's oil this third leg so it's nice and slick."

She worked both hands up and down the shaft until the entire nine inches stood proudly, the helmet glistening. Jimmy felt moist lips engulf the head, and after several minutes of kissing and licking the head, she began sucking.

Jimmy only imagined what the scene looked like. The naked, busty friend of his mother was on her knees, hollowing her cheeks as she stroked and inhaled as much of his cock as possible. Once she got into a rhythm, she rearranged herself so she was astride him with her ass over his face. He reached up and pulled her hips down until he felt her pussy hair graze his nose. He knew what to do next.

Joanne felt his tongue first lick her labia and then slide up and down her slit and enter her ass. She paused her sucking for a moment, closed her eyes, tilted her head back, and moaned. Jimmy had tongued her ass on many occasions before tonight, and she had already climaxed, but there was more to come. The anticipation of what she had planned was making the evening truly special. She didn't want him to stop, but she was ready to move on.

"Okay, big boy. I think it's your turn. Ready?"

Joanne spun around and, still astride him, raised her ass and placed his cock head inside her. Leaning forward, she let her breasts rub against Jimmy's chest, occasionally leaning far enough so he could suck on her nipples. Then she sat back and placed his hands on her breasts while her hips slowly pumped up and down.

"Go ahead and fondle my tits, but very lightly. Tease my nipples with your fingers. Yes, like that. Feel how hard my nipples get when they are excited. I have really big nipples, I know. I used to be embarrassed by them, but now I love the way they look and the way you look when you see them. My boy magnets. That feels wonderful, Honey.

They continued like this for some time before Joanne slid off of him. She got off the bed, and he heard her get something out of the nightstand. When she got back on the bed, she directed him to get on his knees behind her.

"Okay, Honey. Time for you to go to work. Put that beautiful cock in me from behind. Keep the blindfold on for now. You'll have to do it by feel. Think you can handle it?"

Jimmy laughed as he scooted behind Joanne and gripped his cock. He slid it up and down her ass until he felt the familiar sweet spot. He pushed forward and realized she had put a lubricant of some type in that area, and his cock slipped up and onto her back.

"Too high. Better try again. I took the initiative to add a little monkey grease back there. It should make it easier."

This time, he held the tip where he knew it had to go and pushed his hips forward. The helmet gained purchase and slipped inside her. Her cunt gripped him tightly as he slowly pushed inch by inch inside until his hips met her buttocks. His hands were on her ass for balance, and he reached under with one hand and pulled gently on a fat nipple, distending it.

"Jesus! There you are. Home inside me once again. Remember, slow and unhurried. You feel wonderful, Honey, as you always do. I'm so happy I got to be the first one to feel you like this. Mmm, yes. That's it. Nice, slow strokes. We're going to fuck this way for a while. You can get so deep when you are behind me. Let me know if you have to cum, but you are becoming quite the marathon man, Sweetie."

Joanne quietly complimented her young lover, occasionally adding instructions.

"Okay, time to lose the blindfold and see what you are doing. Nothing like a little kinkiness to add variety. So, Honey, here's what is next. I want you to slip out of me and put your big cock in my ass. See how shiny it is. I lubed up just for this occasion. You are going to have to go really slowly at first. My little ass has been invaded before, but not by anything like you are packing."

Jimmy couldn't believe that he was about to fuck his mother's friend in the ass. Not even in his wildest fantasies could he have predicted this.

He did as he was told, but the disparity between the size of his crown and her little anus was worrying.

"I don't think it will fit, Joanne. It just flattens, and I'm afraid I might hurt you."

"You might have to try several times, but it will go, Honey. And it might hurt me for a second, but then it will be incredible. Trust me."

At her insistence, Jimmy firmly gripped the shaft and pressed the shiny crown of his thick member against the little pink star of his neighbor's ass. Once again, it flattened, but then the orifice expanded slightly, and suddenly, he was in.

"Whew! There it is. I knew you could do it. Wow, that takes my breath away. Just hold it there a sec. Let me get my breath...okay, gently now."

Jimmy pressed forward and watched as inch after inch of his cock disappeared between Joanne's cheeks and into that nether orifice.

"Not too deep, Honey. That's good right there. Wow! I forgot how good that feels. What do you think? Do you like being in my ass? That is a special gift, Honey, that I saved for you. Go ahead and give it to me, Sweetie. Just remember–slow and steady wins the race."

And that's what he did. He watched in amazement as his huge cock slid in and out of Mrs. Smythe's perfect MILF ass. In time, they both increased their moaning and intensity until finally, Jimmy had to let it go.

"Oh, fuck, Joanne. I'm going to cum! I can't hold it another second."

"Yes, you are, Honey. Go ahead. Cum in my ass. Mmm, you are so hard. Let it go. Fill me up."

Jimmy gripped her hips firmly and pressed his groin into her buttocks. Joanne responded in kind and pushed back into him as several huge spurts of cum shot into her ass. She took what she could and then collapsed on the bed, breathing hard with Jimmy still buried in her.

It was several minutes before they caught their breath, and Jimmy's penis quietly slipped out of her. She rolled over and kissed him.

"What did you think? You checked off an item on my bucket list. And wow! That was amazing."

Jimmy only smiled. He kissed Joanne passionately and then gave her a brotherly peck.

"You are incredible," he said. He couldn't believe it. He had just fucked his neighbor's ass. And he still had hours to go before the night was over.

"Better rest up, Sweetie. The night is young.