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.