Golden Opportunity

"It's okay, I understand," Simon answered.

"Well you shouldn't have to understand," Helen said in turn, "what I did was a very cruel thing to do to such a nice young man."

"It's okay, really," Simon insisted. "I guess it was fun just to think it might happen for a while."

"Well, still I feel like I owe you something," Helen insisted.

"Well, you did give me a beer."

"That's true," Helen said as she again reached out and took his hand in hers, feeling if not the same reaction, a not unpleasant warmth that spread back across her. "but I was wondering if you would like something else?"

"Well I already had dinner," Simon said.

"Actually, I was wondering if you might like a hand job, just so you haven't gone to all this trouble for nothing."

"A what?" Simon exclaimed, his face turning pale white, even as he was sure he'd had to have heard her wrong.

Rather than repeat what she'd just said, Helen's leaned forward and proved that there was nothing wrong at all with the young man's hearing.

-=-=-=-

Closing distance between them to less than a foot, Helen reached out and slipped her hand beneath the waistbands of both Simon's shorts and the briefs beneath. Simon let out a loud gasp as he felt her fingers close around his already semi-hard cock. Despite the erotic thoughts that had filled his mind these last twenty-four hours, the young man really couldn't believe this was really happening. That this woman, who had once been the den mother of his scout troop, was now playing with his cock. Up until now, it had all seemed a sort of fantasy, something not quite real.

But as her fingers ran up and down his cock, each soft caress sending flashes of delight across his body, it was soon impossible not to accept it all as real. He could feel himself growing ever harder in her hand as she slightly increased her hold on him and pumped it gently.

"Feels nice, doesn't it?" she asked, not really expecting any answer other than yes.

She settled for a sort of grunt as Simon realized that he was almost afraid to breath, much less speak. The cause of his fear that she might stop.

But stopping was the furthest thing from Helen's mind as worked her way further down and cupped his balls. The phrase, "having a man by his balls," had never been about pain as some people might assume, but about pleasure and the prospect of total surrender to that pleasure. It was a truism she had learned from two husbands as well as a number of lovers before and after. Simon proved no exception as she massaged his most sensitive spots, taking total control of his body.

"Why don't you take off these pants so you can be more comfortable?" Helen suggested.

The suggestion might as well have been a command as Simon quickly responded, standing up and pulled down both sets of shorts in an almost single motion, causing a now erect cock to snap to attention.

"Very impressive," the older woman smiled as she continued to hold and stroke his balls with one hand while running the index finger of the other the length of his young manhood.

"Does this feel good?" Helen closed her second hand and applied a tighter grip around his hardness, pulling him even closer to her. "I'm not hurting you, am I?

"Not at all," Simon replied breathlessly.

"Good, because the last thing I want to do is hurt you," the blonde said as she tilted her head closer and gently blew warm air across the head of his cock.

As her lips brushed close enough to the head of his cock as to almost touch it, Simon was filled with the thought that she might actually do just that. That she might actually suck him off was both thrilling and terrifying. Thrilling because not even Stephen had claimed that Laurie did that to him. Blowjobs were something that everyone had heard about, but no one actually knew anyone who'd actually gotten one. At least no one that they believed. The terror coming from the fear that if she so much as touch him like that, he'd shoot his load then and there.

Then, just as he thought she might actually do it, Helen pulled back and concentrated on just massaging him with her hands. Not that he was going to complain about that in any way. Magic was the only word to describe her touch and each brush of her fingers brought a new and unexpected delight.

"Has anyone else ever done this for you?" Helen asked as she continued to work her fingers over everyone one of his six and a half inches.

"Yes..." Simon gasped, trying hard to enjoy the feelings filling him and at the same time, not lose control.

"A girl?" Helen asked.

"Yes..." he gasped a second time, thankful that she had confined the question to one gender. Back when he had first discovered masturbation in junior high, he and his cousin had talked about it one night, comparing notes and going so far as to do it to each other to see what it was like. If she had asked, Simon wasn't sure he would be able to lie and say no.

"Anyone I might know?" Helen asked further out of curiosity.

"Cindy Lyman," Simon confessed.

"Cindy Lyman," Helen repeated with a laugh, "Well I can certainly believe that. You can't imagine some of the things I've heard about that girl. Then again, maybe you can, since I'm pretty certain most of them are true. Especially since I know some of the men involved."

Despite being almost totally enthralled by Helen's ministrations, Simon didn't miss the fact that she'd said men, not boys. One of the stories he'd heard himself about Cindy was that she'd fooled around with older men, some of whom were even married.

"Did you fuck her?" Helen asked.

"No," Simon quickly answered, the disappointment evident in his reply.

"Really?" Helen responded, the surprise in her own voice equally evident. "Well I would hope she at least gave you a blow job then."

Simon didn't answer, but his silence said that hadn't happened either. It wasn't that he was embarrassed to admit it, he was just too stunned to learn that Cindy was indeed one of those seemingly mythical girls who actually did things like that.

"You've never done either of those things with a girl, have you?"

"No, I haven't," he answered, hoping she wouldn't think him a loser for not having done so.

"Well, I'm sure that none of your friends have either, no matter what they might claim," Helen smiled with assurance.

That made Simon feel better.

"So I guess the question now is, would you like to?"

Even more than before, that question stunned Simon into silence.

"Even if it's with an old lady?"

"I ... I don't think you're old at all," Simon managed to say, much to his own surprise.

"That was exactly the right answer," Helen said as she moved even closer and kissed him right on the lips.

Sometime back, one night while he and the guys were talking about girls and sex, one of them had, for some unknown reason, brought up the subject of older women. The question had been asked, what would it be like to kiss one of them. The consensus, Simon remembered, was that it would be like kissing your grandmother. If asked that question again, he'd certainly have to come up with a new answer. Unless of course he could somehow envision his grandmother snaking her tongue deep into his mouth and exploring the furthest reaches of his mouth.

"Wow," Simon exclaimed when Helen withdrew her tongue.

"Not too icky?" Helen asked with a smile, even as she continued to hold his cock in her hands.

"Not in the slightest," Simon quickly replied.

"Better than Cindy Lyman?"

"No comparison," Simon gushed.

"Well, I have had a few more decades practice than she has," Helen laughed.

Simon tried to laugh as well, having to agree with that assessment. It also occurred to him that there were many other things that Helen had to have had a lot of practice at.

"Are you sure you want to do this?" Helen asked, her voice again becoming more serious.

"Definitely," Simon said with confidence.

"A large part of me says that I'm going to regret this come tomorrow," Helen continued in that same tone, "but then again, I've always been a believer that tomorrow somehow always takes care of itself. So why don't you pull your pants back up and we'll take this up to my bedroom where I'm sure we'll both be a lot more comfortable."

Filled with the realization that every one of his most secret dreams was very well about to come true, Simon did just that with such vigor that he almost knocked himself over when he reached down for his shorts. Helen let him compose himself and then led him up the back stairs to the large master bedroom just above the kitchen.

-=-=-=-

Stepping into the bedroom, Simon barely gave his surroundings a glance, except for the large, king sized four post bed in the center of the room. It was more than twice the size of the one he slept in back home. He was so wrapped up in the thought of what was about to happen in that bed that he didn't even notice when Helen stepped away from him and lit a half dozen candles that were scattered around the room. Once done, she pressed the wall switch she had turned on when they entered the room and the lighting dropped to a soft, half light that gave the room a much more romantic feel.

"Why don't you make yourself comfortable," Helen told Simon as she pulled something he couldn't see from the top drawer of a large dresser. "I'll be back in a few minutes."

As she disappeared into the adjacent bathroom, Simon pondered for a moment just what comfortable meant. Should he take off all of his clothes or just his outer shirt and pants? Getting naked wouldn't seem too forward, he thought. After all, not five minutes ago Helen was playing with his cock. He thought about it another few seconds and decided to strip down to just his briefs.

He'd just draped his clothes onto a nearby chair, his socks and sneakers right under it, when the bathroom room reopened. Simon had to roll over to look in that direction and when he did he found himself speechless once more.

Having turned off the bathroom light before she opened the door, Helen stood bathed in the glow of the candles. The outfit she had been wearing had been replaced by a very sexy set of black lingerie. Simon didn't know what most of the things she now wore were called, but he'd seen them in magazines guys passed around school.

If he'd paid more attention to what was written under the photographs that they'd all drooled over, he'd have recognized the main part of her ensemble as a bustier, cut low enough to show a considerable amount of cleavage. Dropping his gaze to below her waist, he recognized the matching panties, even if they were more transparent than anything he'd find in his mother's or sister's laundry. The stockings she wore, attached to the bustier by garters, were equally translucent, as was the long robe that hung open across her shoulders.

"I hope you like it," Helen said as she turned right and left to give a greater appreciation of the outfit and the body it enhanced.

Like was hardly the word that came to mind as Simon felt his cock grow instantly hard against the confines of his fruit of the looms. If Helen had come out of the bathroom totally naked, he'd hardly have been as spellbound as he was right now.

"I said you should make yourself comfortable," Helen said as she took the half dozen steps that separated her from the door to the bathroom and the side of the bed. "I don't think you're very comfortable with your underpants all tight like that." she added with a grin.

Reaching the bed, she sat on the edge of it and taking hold of both sides of his waistband, pulled is briefs down and off. Discarding them on the floor without a second thought, her attention immediately turned to the fully erect cock standing less than a foot away. Her outstretched fingers glided up and down the stiff column, causing Simon to practically jump as her touch sent a electric surge across his now naked body.

A reaction that pleased Helen to no end as she moved even closer and bent down to kiss the crown of his cock. Just as her lips made contact, she slipped her tongue between them and licked off the small pearl that had formed from his excitement.

"Mmmmm, tasty," she practically purred as she closed her fingers around the base of his cock and opened her mouth even wider.

"Oh my God!" Simon gasped as Helen took his entire length into her mouth.

Simon really believed he was about to pass out. None of the things the other guys had said about getting a blow job had been anything close to what he was feeling right now. The touch of Helen's tongue brushing up and down his flesh was heaven, coupled with the almost vacuum like pressure of her lips, he was sure he was going to lose it any second. And if it had been Cindy Lyman doing the honors, he undoubtedly would have. But Helen had decades of experience, not months and knew just went to back off to keep a man from coming. Even a young man lacking anything faintly resembling self-control.

Her hands massaged his balls, applying gentle pressure in just the right places to hinder a climax. Then she would bring him back to the edge once more and start all over again. Helen knew that, unlike most of the men who had shared this bed since her husband had died, Simon would easily be able to climax more than once, but why rush. Better to show him how much fun it could be to take your time. Something most girls his age hadn't learned yet.

Simon had closed his eyes, abandoning himself to the pleasures of Helen's oral talents. He felt his cock sliding ever deeper into her mouth as she began to suck him with ever increasing passion. For once brief moment, he considered the idea that his uncle had to be crazy to have passed this up. But that moment quickly passed, not to return.

Opening his eyes, Simon watched as Helen's head bobbed up and down, her mouth tightly wrapped around his cock. With each upward motion, she almost let his cock slide free, but then took him whole once more in a quick downward plunge. The effect of which on Simon was immeasurable.

Simon had no idea of how long this went on, or that somewhere along the way, Helen had abandoned her efforts to keep him from coming. It was only when the fires within him again brought him to a boil and then beyond did he realize that he was about to enjoy the orgasm that he had been waiting for.

"Oh God, I'm going to come," he managed to say as he felt his climax building, even as Helen's lips and tongue worked even harder on his cock.

An effort that saw the fruits of her labors only heartbeats later as Simon exploded in her mouth. The richness of his ejaculation, so long absent from the men who usually enjoyed her charms, caught her by surprise. But only for a moment as she happily, even greedily, swallowed every drop. It was a prize she had enjoyed ever since the first time she had ever pleased a man in this manner.

Even as she continued to drain Simon of every last bit of his orgasm, Helen thought for a brief moment of the last time she had tasted a boy this young. She had been a year younger than Simon, and had learned about oral sex from an older woman who lived in the same apartment building with whom she had struck up a friendship. At first, the advice the newly immigrated Frenchwoman had given her seemed quite gross to the younger woman. But soon enough, the passions that filled her when she was alone with Johnny O'Connor broke down her walls of resistance. Trying what Anna Maria had told her seemed a much safer path than spreading her legs and risking pregnancy as some of the other girls did. More so, it made Johnny much more willing to try something else that the thirty year old had explained to her. Something that she now planned to pass on to Simon as well.

"That was fun, wasn't it?" Helen asked as she let Simon's now shrinking cock slip from her mouth.

"That was awesome," Simon expanded. "I never imagined how great that could be."

"Well there are a lot of things I'm sure you've never imagined," Helen smiled as she playing ran two of her fingers up and down his flaccid cock, leaning down to kiss it a last time before letting it go. "Hopefully we'll have time to show you more of them."

"I can get hard again," Simon quickly assured her, thinking that his current limp state was causing her concern. "Sometimes I can get hard three or four times in a night," he added, his tone bordered on being boastful.

"I'm sure you can," Helen said with some amusement, "but there are things that you can do in the meantime as well. Making love is about a lot more than just fucking. Many young men never take the time to learn that."

"Oh I want to learn," Simon quickly replied, realizing that he might never ever get a chance like this again.

"And I'm going to teach you," Helen assured him, "so why don't you just lay back and we'll start on lesson one."

Simon stretched out on the bed, his head against the pillows propped alongside the headboard. Helen lifted herself up and climbed over him, kneeling across his waist, a bended knee on each side of him.

Reaching out with her hands, she ran her fingers across his chest, brushing against the thin layer of hair and rubbing his nipples until they grew hard. Gently at first, she squeezed them, then applied a little more pressure. Simon had never before considered the idea that a man's nipples could be as sensitive as a woman's, but it was a fact he was delighted to discover. Especially when Helen leaned closer and replaced the touch of her fingers with that of her tongue.

"Hmmm," Helen purred as she tickled his nipple with the tip of her tongue, making it hard enough to slip into her mouth.

"Ohhhh," Simon gasped as the older woman wrapped her lips around his nipple, even as she continued to play with it with her tongue.

"I want you to pay careful attention to what I do," Helen said as she let him slip from her mouth and turned her attention to his left side, "because after this, I want you to do the same thing to me."

The lesson went on for at least ten minutes more, with Helen going back and forth, leaving a wet trail between his nipples. The sensations she produced were new and exciting to the young man, causing both a pleasing warmth across his body and a renewed hardness between his legs.

Finally, Helen lifted herself back up and undid part of her outfit. The top of the bustier came free, falling to the side as she covered her now exposed mounds with outstretched fingers. Simon watched intently as Helen squeezed her breasts, rubbing them with her fingers and giving him a quick peak at her nipples and the dark pink circles around them.

Dropping both hands at the same time, she moved just a little closer, so that her breasts hung just above Simons head. Close enough for him to reach up and take matters in hand.

Something he paused several long moments before doing, content to just enjoy his first really good look at a woman's boobs. Oh he'd had quick glimpses of them before, even if they'd belonged to his mother or sister. And of course there were always the girls at the beach who wore suits just tight enough to let their nipples show through.

They were hardly the stuff of the men's magazines he and his friends kept hidden in their rooms, but they were real and more importantly, his for the taking. Closing a hand around each of them, he squeezed them softly, amazed at how soft and warm they felt.

Using his fingers like she had shown him, Simon played with her nipples, bringing them to a length twice as long as his had been. They looked so inviting that he couldn't wait any longer and he eagerly brought his mouth to the closest of them.

Helen let out a loud sigh as his lips closed around her nipple, smiling broadly as he imitated the movements of her tongue.

"Just a little softer," she whispered as he sucked on her breasts, "yes, just like that."