The relationship between Henry and his neighbor, Jodi, continued to grow and develop. Henry was an astute learner and Jodi was an able teacher, not to mention one with a killer body. They both knew that this was a short-term solution to a long-term problem. Jodi was still grieving the loss of her husband, but at least one niche had been filled: satisfying sex.

And Henry was pinching himself. He had fallen into every teenage boy's dreamscape: he was having regular sex with a big-titted, and beautiful MILF who was coaching him to be a wonderful lover. He had almost stopped jacking off as a result. Even though he was servicing Mrs. Haas regularly--usually once a week--he relived those experiences late at night or even early in the morning with his hand wrapped around his engorged cock.

The mental image of her sitting on top of him as she ground her ass into his groin and screamed his name during a climax caused him to lock his bedroom door and pull out his thick prick. Jodi had praised his cock so much that he frequently measured it in various states of excitement with his mother's fabric tape measure. He had to sneak it back into her sewing drawer when she asked him if he'd seen it.

"My sewing tape has disappeared, Henry. You haven't seen it anywhere, have you?"

"Oh, you mean the one I use to measure my cock with, Mom?" he had NOT said to her. It was bad enough that she seemed to suspect something was going on with him.

"You seem to spend a lot of time over at Mrs. Haas' lately. Does she have a special project going on?"

"Yeah, she's teaching me how to fuck her in a variety of positions. Her favorite is doggy style," he thought to himself but instead answered with, "I'm helping her renovate her garage as well as cleaning the pool. She seems to like the work I do."

"Well, I'm glad you are helping her out. It must be tough to lose a husband. You're a sweet boy, Henry. I'm sure she appreciates all that you do."

Henry was careful about concealing his real behavior toward his neighbors from others, especially his family. And as much as he looked forward to his usual Wednesday trysts with Jodi, she encouraged him to date girls his age.

"Henry, you should check out the girls you go to school with. I know you love helping me out, but we both know that this has to end at some point, probably this fall, and as much as I love what we are doing, I want you to have normal relationships as well."

But lying in bed next to her with his cock in her hand and her big tits poking into him, there was little incentive to date other women, especially inexperienced teenagers. Henry had developed a new sense of confidence now that he was no longer a virgin and was learning the multitude of ways to please Mrs. Haas. And it showed. Girls he knew seemed to take a newfound interest in him. He exuded a quiet confidence that was sexually attractive to young and older women alike.

He had harbored a crush on a classmate, Brenda Webster, for some time but never dared to act upon it, and admitted so much to Jodi. With her encouragement, he finally got the courage to ask her out, and to his surprise, she accepted. He later discovered that she had recently broken up with her boyfriend who was cheating on her, so it was a rebound date.

Brenda had been in several of his classes. She was smart and cute, but she also possessed a great pair of lungs, as the boys in his group called them. Brenda Webster had world-class tits for a teenager.

That first date had been a movie and then a soft drink at a local teen-age hangout. Brenda was open and sincere, and he found her easy to talk to. She also seemed genuinely interested in him, and as Jodi reminded him, why shouldn't she? He was handsome and smart. And that first date ended with a kiss, albeit a brief one, But she initiated it. Henry was on cloud nine.

A subsequent date went just as well, and when he finally parked his Bel Air on a hill overlooking the lights of the city, she easily fell into his arms and got a taste of Henry's kissing skills. Before long, they were locked in a sweet embrace and his hands found her perky breasts underneath her sweater. Brenda offered no resistance, only moaning when his fingers found a ripe nipple through the sheer bra she was wearing.

Henry worked slowly, his hands caressing and his lips kissing and eventually he was able to deftly unhook her bra with one hand. Brenda only smiled when she realized how skillfully it had happened before she even realized what he was doing.

"Pretty clever, there, Henry. I might as well get this sweater out of the way, hmmm?"

She reached down with both hands and grabbed the hem, lifting her sweater over her head. Her unfastened bra lifted off those perfect globes and Henry gasped inaudibly. Brenda had the breasts of a goddess: perky cones that needed no support and were capped by dollar-sized pink nipples that pointed directly at him waiting to be sucked. She'd seen other boys react similarly, and she loved the attention, especially when a pair of soft lips found a nipple and sucked on it. The sensation went right to her pussy. Brenda was not a virgin, but she wasn't easy, either. She was selective about whom she fucked. And Henry was looking to be high on the selection list.

"Your tits are perfect, Brenda. My God, even better than I imagined." It wasn't the most clever thing to say, but it was heartfelt.

Brenda beamed. She hadn't had sex since the breakup with her boyfriend except with a plastic dildo she kept hidden in her closet. She hadn't been planning on having sex with Henry, but if he had a condom, she'd at least be tempted.

"I'm glad you like them. Umm, that feels so nice when you suck on them like that. You're making me horny, Henry." She giggled at her unintended alliteration. "Horny Henry..." she giggled again.

Henry needed no more coaxing. His lips found a ripe nipple between kisses elsewhere, and he began working his hands up her creamy thighs.

Brenda responded by letting her hands roam over Henry until she found a noticeable bulge in his shorts that nearly extended to his knee. Her eyes popped open in surprise. She looked down to see a thick tubular shape ending at the hem of his shorts.

"Jesus, Henry. Is that all you?"

She squeezed it again to be sure. Confirmation in hand, she wondered silently if she could handle all of it. At the very least, she had to see it. As Henry kissed and fondled her breasts, he scooted forward so she could unbuckle his belt and unfasten his shorts. Once freed, he raised his hips and she slid his shorts and boxers to his knees.

"Holy Hanna! You're huge, Henry!" Once again Brenda giggled at her accidental poetic device.

Brenda had discovered with her previous boyfriend that she loved to suck cock. The feel of a stiff member filling her mouth and hand made her tingle with excitement and she loved the power she had over a guy with his cock between her lips. But this was the biggest cock she had ever actually had in hand. She couldn't wait to get it in her mouth.

"Mmmm, I never would have guessed you'd be this big, Henry. Would you mind if I gave you a blowjob?"

Henry couldn't believe his eyes or his ears. This sweet, young classmate that he'd had a crush on was about to suck his cock. Brenda smiled at him and then lowered her mouth until his fat glans was between her lips. Her tongue swirled around the head as she slowly slid her hand up and down his length.

Henry reached down and cupped her perfect breasts as she worked on his cock. He had learned to keep from cumming too quickly with Mrs. Haas through sheer willpower, but watching this beautiful redhead teenager suck on him was almost too much. He also knew from experience how exciting it was to talk dirty during sex, and he tried it on his date.

"Brenda, you look so sexy with my cock in your mouth. Oh my god, your tongue and lips feel so good. I love the way you suck my cock."

But Brenda was only getting started. It had been too long since she'd had an opportunity like this, and she couldn't believe what a beautiful, fat cock Henry had. She had both hands wrapped around it and could barely get half of it in her mouth without gagging. And the thick vein on the back of it was beginning to show the first stages of a huge ejaculation.

"Brenda, if you don't slow down I don't think I can control myself. Oh, fuck, that feels good."

Henry's praise only prompted her to suck harder, and after a minute or two longer, that's all it took. Suddenly his hips bucked and she felt a thick stream of sperm shoot into her mouth accompanied by a loud grunt from Henry. She had tasted cum before, but never in a quantity like this. She pumped his prick in rhythm to her sucking as the milky seed filled her mouth. Soon it was overflowing and spilling onto her hand and Henry's thighs. She continued to pump him and suck, hollowing her cheeks until his cock finally quit pulsing. She ran her tongue around the head and licked her fingers.

"Wow! That was quite a load. I had trouble keeping up but you were good to the last drop. Did you like that?" She giggled in obvious delight over Henry's exhausted smile.

"Fuck, Brenda. That was fantastic. But now it's my turn."

But Brenda then looked up and the dashboard clock registered with her for the first time. A panicked look took over as she realized how late it was. She was sure to be in trouble.

"Oh, shit. Unfortunately, I'll have to take a rain check. Is that the right time? If so, I'm screwed! Metaphorically speaking, I guess. I was supposed to be home by eleven and it's going on midnight."

After confirming the time, Henry quickly pulled up his pants while Brenda returned her clothes to their normal state, and with a quick kiss, they headed back to town. Brenda leaned against Henry and fondled his penis through his shorts.

"Guess I'll have to wait a while for this snake of yours, but I'll be thinking of it. That is if you want to ask me out again."

"Are you serious? Wild horses couldn't keep me away, as the song goes. When are you free?"

"Not till next weekend. We're going to my sister's for a couple of days, but I'll be back by next weekend. I think my folks are going to the cabin so I might have the house to myself. How does that sound?"

"Fucking fantastic. I can't wait."

"Just one thing. Bring a condom. That is if you actually want to do it--you know--fuck me."

"Are you crazy? I'll bring a box of condoms. Pre-lubed. Any color preferences?"

"Just make sure they fit that big boy of yours. I'm happy I got to finally meet the real you."

She kissed him sweetly at the door and went inside. As Henry drove off, he saw the curtains part briefly and someone peek out. He hoped it wasn't an angry parent. Brenda Webster was turning out to be another dream come true...no pun intended.

A few days later Henry was at Jodi's doing his weekly chores. In short order, he had cleaned the pool and balanced the chemicals. What little lawn she had, he mowed and trimmed. His inside chores still awaited, however. As usual, he double-checked to make sure no one was visiting and just in case, he knocked and waited for an answer.

The sound of bare feet on the tile floor alerted Henry, and soon Jodi's image appeared through the small kitchen door window. Her auburn tresses were tied in a ponytail and she was wearing typical summer garb: a tank top and nylon shorts. The tank top must have been her husband's because it was three sizes too large and her braless big boobs bobbled nicely, a fat nipple occasionally peeking out the side armholes. Henry's cock hardened at the sight of his neighbor.

Jodi opened the door with a smile.

"Hi, Henry. You're looking chipper today." She looked down and noticed his shorts were tented in front, a common site at these weekly meetings. "I see you're ready for some indoor action by the look of that sausage trying to escape your shorts. Come on in and let's see if we can take care of that protuberance."

Henry followed Jodi into the bedroom, where she plopped herself against the headboard and patted the space next to her for him.

"Tell me what you've been doing lately. Oh, and how did your date go? I want to hear all about it."

Henry smiled at the inquiry. His family had only shown cursory interest in most elements of his life, but Jodi seemed genuinely interested in his activities. She was like a concerned mother, except that he was fucking her regularly.

"It was fine." He gave the standard male response to nearly everything. But his smile belied more to the story as he joined her on the bed. And Jodi noticed.

"Oh, come on. You can tell me more than that! Bottom line--did you kiss her? Or maybe even more? Is she cute? I've been wondering what is your type other than old ladies."

The irony of the situation was not lost on either of them. Jodi's motherly intrusion into Henry's life contrasted with the fact that they were about to engage in consensual sex. A kiss from a high school sweetheart paled in comparison to the monkey sex they were about to enjoy. On the other hand, Henry didn't want to spoil his relationship with Mrs. Haas. While he felt secure that he was on solid ground with her for at least the short term, he worried slightly that admitting to a blowjob from Brenda might change the dynamics with his sexy neighbor.

"Yes, we kissed. I'm going to ask her for another date. And, yes, she's cute. She's a redhead but that's not a big deal. I had a good time and I think she did as well." Even though she had a hard time talking with my cock in her mouth.

"That's wonderful, Henry. I think we should celebrate. I have a special treat in mind that I think both of us will enjoy. It's in the den. But first, just hold me and kiss me for a bit. I've been looking forward to seeing your handsome face all day."

In short order, they were wrapped in each other's arms and Henry was kissing and fondling her fat nipples as Jodi massaged Henry's cock through his shorts. After a while, she broke off their embrace and winked at him.

"Follow me." She jumped off the bed and walked to the doorway before turning around and beckoning him with a crooked finger to follow.

When they reached the den, Henry could see that a massage table had been set up.

"I thought it would be fun to massage each other. Only we get to bend the rules a little. No body parts are off-limits. And both the client and the masseuse have to be naked. How's that sound? And I'm going to do you first so get rid of those clothes."

Henry wasted no time getting undressed and lying on the table on his stomach with his head supported by the extension for that purpose. Facing the floor, he closed his eyes and listened as Jodi put on ethereal music and stripped naked. Soon he felt a stream of warm oil on his back and shoulders and a pair of hands slowly rubbing it into his skin.

His muscles relaxed as her hands slowly worked their magic down his neck and back to his legs before returning to his buttocks. Soon he felt the addition of something soft rubbing over his body and realized that Jodi was massaging him with her breasts as well as her hands. As he felt his muscles soften and turn to Jell-O, he nearly fell asleep, but then he felt a slap on the ass.

"Turn over. Here comes the fun part."

Rolling over onto his back, Henry had to refocus his eyes. Jodi was pouring more oil on her hands as she stood completely nude over him. Her nipples stood erect from her slightly sagging breasts, each pointing outward at a slight angle.

After rubbing her hands together, she gently massaged his neck and chest. Henry's cock was only at half-mast, lying on his abdomen and stretching to his belly button. Jodi slowly worked her way toward it and then lightly brushed it with the back of her hand. His penis immediately responded by jerking skyward an inch or two.

"Hmmm, your cock appears to require special treatment. I'll try to remove the tension, but I may have to resort to some special tricks they don't teach you in massage school."

Jodi gripped his penis in her small hand and stroked it gently. With her free hand, she rubbed Henry's testicles after spreading his legs so they could hang loosely between them.

"I love your big balls. I bet they're full of sperm just waiting to shoot out, but let's make sure it doesn't happen too soon. I want to feel all that cum shoot into my pussy, but that won't be for a while."

Jodi had her teenage neighbor in her complete control. As his cock stiffened, it stretched toward the ceiling and Jodi encouraged it even more with kisses and gentle sucking. Occasionally, she stopped to concentrate on Henry's legs and chest, but she always returned to his thick phallus, now ramrod stiff and huge, like some kind of freak Greek statue.

After about five minutes of this, Jodi climbed aboard the table and straddled Henry, his cock shaft sticking up in the crevice between her parted labia and rubbing against her clit, the glans proudly displayed above her thighs.

"Yumm, this looks good enough to eat, but I bet you'd just like to stick it in my tight little pussy. But for now, I'm going to just massage you with my cunt. That sounds so dirty. I bet you never thought your next-door neighbor talked like that, but I can tell that you like it when I talk nasty. Don't you?"

Jodi leaned over and rubbed her breasts over Henry's chest before reaching forward and feeding him a shiny nipple in his mouth. Henry responded by grabbing them and sucking on each nipple in turn, extending them with his sucking action.

"Oh, Honey. Yes! Suck on my big tits. I love that. You're making me super horny."

As she reached forward, Henry's cock slipped under her raised ass and between the crevice of her apple ass cheeks. Jodi sat back and rubbed her ass against his cock. At one point, the slippery head almost entered her anus. Jodi gave a startled scream.

"Oh my! A little early for that. Your cock must have an anal radar. But that hole is going to have to wait. I think you need to massage me for a while. Let's switch places."

Jodi got off of Henry as he stood, and then she lay on the table on her back. She grabbed his stiff cock and stroked it as Henry rubbed oil between his hands.

"I bet you've dreamed of massaging a big-breasted woman before, haven't you? Well, here we are. Don't leave anything out." Jodi parted her legs, exposing her fleshy labia and large clitoris. Her two-finger patch of pubic hair had been recently trimmed. She closed her eyes and smiled.

Henry's cock got even harder, if that was possible, as he massaged Jodi's fleshy tits, pulling and squeezing her huge pink nipples. With his hips by her head, he reached down and parted Jodi's pussy lips and inserted just the tip of his finger inside her when he felt her hand on his cock and she reached over and put his prick in her mouth. His cock was so swollen that she could only get the head between her lips, but thankfully it was so oily that she could stretch her mouth over the glans.

Both of them moaned as they worked on each other. Finally, Jodi removed his cock and begged Henry.

"Oh fuck it, Honey. I can't wait any longer. Just get up here and fuck me. I need to feel you inside me."

Henry wasted no time climbing on the table, ignoring the fact that it might collapse if he were too rambunctious. Jodi raised her knees and as Henry kneeled between them, she grabbed his thick shaft and rubbed the head between her pussy lips before finally pulling it inside.

"Oh, fuck. There it is. Jesus, you feel good. Nice and slow, Honey. You know how I like it. I'm so horny I could come soon. That's it. You are such a good lover, Henry. I love the way you fuck me."

Henry stroked his cock in and out of his middle-aged neighbor, watching the head all but come out ever so slowly before shoving it back in forcefully until his balls slapped against her ass. After fucking this way for ten minutes or so, Jodi rolled over.

"Fuck me doggie style, now. You get so deep that way."

Henry stared at Jodi's raised perfect ass and slowly rubbed his cock against her cunt lips before raising it and rubbing it against her asshole. He wanted to shove it in her ass but knew better and lowered it again and inserted it in her velvety pussy. Jodi was sopping and her pussy made audible squirting noises as he fucked her. She reached back and with two fingers massaged her clit as Henry slammed in and out of her.

Finally, it happened. Jodi let out a scream and her body convulsed. As she jerked forward, Henry's cock slipped out of her and when he went to insert it, it lined up perfectly with her anus. He slowly pushed his hips forward and watched as her pink star opened and his fat cock head, still covered in massage oil, slipped inside. Once the head was in, the ring of her ass shrank around his shaft in a tight grip. He slowly pushed forward until he was all but buried in Jodi's ass.

"Oh fuck, Henry. What are you doing?" Jodi's body gave an involuntary jerk as a response, but her climax overwhelmed her. Instead of letting him slip out, she gripped the sheet on the massage table in her fists and pushed her ass back against him until all ten inches of his cock was in her ass.

"Oh, Honey. Go ahead. Fuck me there. That feels so good with your big cock in my ass. Oh, fuck. Cum in me, Honey. Cum in my ass."

And Henry did. He shot off like a rocket in Mrs. Haas' ass, filling her up with his sticky sperm, buried to the hilt until he finally pulled out. His cock quickly softened and plopped down to the table as a stream of white cum flowed out of her ass, down her labia, and onto the sheet.

Henry collapsed on top of her, exhausted. One more barrier had been broken. What could top this? They lay together breathing hard for some time, Henry's cock nestled between Jodi's butt cheeks.

Eventually, both Henry and Jodi hopped in the shower together. They hugged and kissed, but spoke little. Finally, Henry excused himself. He did not want to admit it, but he had to go home to dinner and small talk with his family after fucking his beautiful neighbor's ass. He was living in two completely different worlds.