Golden Opportunity

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That the breasts he was sucking belonged to a woman older than his mother never entered his mind. In fact, looking at her now, it was hard to imagine how old she was at all. Helen had always kept herself in good shape, keeping the effects of time at bay in a way that most younger women could only envy.

Holding her breasts in the palms of her hand, Helen alternately fed them to Simon. He proved an eager and appreciative student, taking the basics of what she had taught him and quickly improving on them.

"You're very good with that tongue," Helen said as after kissing him long and hard. "I think you're ready for the next lesson."

With that, she lifted herself off Simon and dropped down alongside him on the bed. At her request, he moved to the bottom on the bed, situating himself between her legs. Simon had a good idea what came next, but the idea of doing to a woman what she had done for him earlier was something that had never even entered his wildest fantasies.

If it was one thing all the guys had agreed on when the subject of cunnilingus came up, it was that it had to be the grossest thing they had ever heard of and there was no way any of them would ever do it. Yet, at the same time, none of them seemed to have any problem with the idea that a girl might put one of their cocks in her mouth.

While he was moving to where Helen had directed him to, she undid the small snaps that held the panties to the rest of her apparel. She waited until he was comfortably in position, then let the covering slide free as easily as that covering her breasts had done.

The sight of a woman's sex was something Simon had never seen, even in books. His first reaction, was that it was indeed gross. The hair that surrounded her pussy was a mixture of colors, the majority of which was white and gray. Remembering stories, jokes really, that the guys used to tell about a pussy smelling like fish, Simon was surprised to find that wasn't the case at all. In fact, once he got used to it, it was a sort of sweet smell.

Certain that this was his first real view of a pussy, Helen was content to just lay back and let Simon explore her sex at his own pace. There would time enough when he was ready to continue the lesson. To her satisfaction, it didn't take long at all for Simon to reach out with his hands and begin that exploration.

As his fingers brushed against the damp mound, and then the even wetter place within, Simon's first reaction was how much it felt the same as the time he'd had his hand down Cindy's pants in the backseat of his father's car. Somehow, he thought it might be different, given that Helen was so much older and all. If there was a difference, he hardly had enough experience to tell what it was.

Remembering what Cindy had said about her clitoris, Simon carefully explored with his fingers until he found it. It was a lot easier, he thought, when you can see what you are doing. Soon finding his prize, he began to gently massage it with his fingertips.

"Oh yes, right there," Helen offered, impressed with his show of initiative. So much so that she decided to just let him go on his own and see where it led.

Simon continued to play with his new discovery, paying careful attention to Helen's reactions as he gently probed her inner reaches. Once certain he had pretty much mapped it all out, he decided to take a major step further and try what all of his friend, and himself, had swore they'd never do.

"Oooooo," Helen moaned loudly as Simon reached forward with his tongue and guided it between his fingers to brush against her clit.

It was different, of that he was sure, but no where near as bad as he had imagined. The gross factor quickly gave way beneath the cries of pleasure his actions were producing in the woman beneath him. Even more eagerly than before, he began to work his tongue in earnest, treating her excited nub the same way he had earlier massaged her nipples.

For a total amateur, especially one doing this for the first time, Helen decided that Simon wasn't half bad. He'd managed to quickly overcome any initial reluctance and give it his best effort. All he needed was a little seasoning and some helpful hints.

Hints which Helen was more than happy to give, speaking in the same soft, gentle tone she had used to instruct nine-year-old in the activities they needed to master to earn their Cub Scout badges. Her own fingers replaced Simon's as she helped guide him to the right spots, explaining how to improve his performance. There might not be a merit badge in the offing, but she was sure he wouldn't be disappointed at the outcome of his efforts.

Adding her own touch to his, Helen quickly brought herself down a well traveled path that she knew would lead to a climax. She helped carry herself all the way to the threshold, then withdrew her hand and let Simon continue on his own.

Realizing what she had done, he doubled his efforts and was pleased to feel her body respond. Laying her head back and closing her eyes, Helen savored the moment and looked forward with anticipation to what she knew was only brief heartbeats away. Making a woman climax for the first time was something a young man would always remember, and she wanted nothing to distract him from that goal.

The seconds passed and an orgasm was upon her. Not the sort a more experienced lover might produce, but pleasing nevertheless. Especially since it was his first.

Feeling her body quake beneath him sent similar tremors across Simon's chest and he almost thought his heart might stop beating. Such was his excitement. But his heart went on, and when he remembered to do so, so did his breaths. Lifting himself from between her legs, he was met with a look of contentment on Helen's face.

"Did I really make you come?" he asked, remembering overhearing someone say that some women fake things like that to make a guy think he had.

"You certainly did," Helen assured him, thinking that it was indeed the truth, even if he had some help along the way.

"Wow," Simon heard himself say.

-=-=-=-

After giving him a few long seconds to savor that knowledge, Helen told Simon to switch places with her and no sooner had be stretched out on the bed, she took his cock in hand and gently gave it a few playful pumps. Her mouth followed her hand and before he knew it, his hard manhood was again deep in her mouth.

"Oh yeah!" he cried as he felt her sweet wetness engulf him.

As she had done before, Helen quickly worked her tongue up and down his shaft, her fingers manipulating the sensitive skin at the base of his cock. This time, however, the object wasn't to make the young man climax but merely to insure that he was as hard as could be. Something she needn't have worried about. Young men his age, she should've remembered, were eternally hard. Just as many young women of the same age were perpetually wet, even if a much smaller number of them would admit it.

Letting his cock slip from her mouth, Helen took hold of the sides of her breasts and pressed them together, trapping his stiffness between them. She vigorously rubbed them up and down, catching the head of his cock with her tongue as it emerged from her flesh, tickling it with darting strokes.

"Ooooo," Simon again moaned, delighting in the effect she was having on him.

"Just hang tight," she said wordlessly to her young lover, "because it's only going to bet better."

Lifting herself even higher, Helen stood halfway up and again reached down to take his cock in hand. Then, holding it tightly, she brought herself back down, placing the tip of his cock against the entrance to her pussy.

Gently she rubbed the two together, satisfying herself that she was sufficiently aroused as not to need any help with what was to come next. Not that she thought Simon would've minded if she'd needed to resort to the small tube of lubricant in the night table. In fact, she'd gotten so good at applying it surreptitiously, most men didn't even notice.

"Ready?" she asked with a smile as she looked down on Simon, her fingers continuing to rub along the sides of his cock.

Simon replied with an equally anxious smile, not wanting to waste words when he was trying to forever memorize every aspect of what was happening.

Slowly, methodically, Helen brought herself down and took Simon inside of her. She could feel his hardness filling her as she moved, content that while she was hardly as tight as she once was, it was more than enough to give the young man a most memorable experience.

"Fuck!" Simon gasped as he felt the weight of her body come to rest against his, signaling that he was totally inside of her.

The weight lasted only a moment as Helen lifted herself up just a few inches and slid back down. A movement repeated again and again, each time with her rising a little higher and coming down more forcefully. A rhythm quickly developed and with it the realization that Simon had just surrendered his virginity.

Talking hold of her thighs with his hands, Simon added his motions to her own, meeting her downward thrusts with ones just as powerful. One thought dominated his brain, he was actually fucking a woman. Her age or who she was didn't matter, he assured himself. He was doing what he was sure none of his friends had done, despite their boasting.

"Oh yeah, baby," Helen assured him as she got more and more into it, "you're doing fine. That feels really good!"

And feel good it did, but as the minutes passed, Helen realized that she was missing a golden opportunity. All of her recent lovers, her late husband included, had been men of her own age. Men who might have had the will, but not the energy to give her the fucking she used to so enjoy. Not that she hadn't enjoyed their attentions, but why let a chance like this go.

"Simon, change places with me," she said, lifting herself off him in a motion so quick as to surprise him that he was no longer inside of her.

Anxious to rectify that, he quickly moved to comply with her request, order actually. Helen dropped onto her back and spread her legs wide, inviting him back inside of her. An invitation he just as rapidly accepted, taking hold of his cock and slipping it past the folds of her wet mound. The return of her warmth against his flesh brought yet another loud moan from the both of them.

Helen was content now to just lay back and let Simon do most of the work. Moving on instinct and the memories of hundreds of late night fantasies, the younger man pumped his manhood in and out of her as fast and hard as he could. Each thrust sent echoes of lust through both of their bodies. Echoes that grew in both frequency and intensity as the clock on the wall passed the minutes.

With her legs wrapped around him, Helen ran her hands up and down his back, stroking his sweat covered flesh. Her own was no less damp. Words of encouragement passed from her lips, urging him onward with assurances that he was indeed doing it oh so right.

Experience and an understanding of what young men were like told Helen that at the rate Simon was going, he wouldn't last much longer. That thought reminded her that there was something else she missed. Getting her lover's attention, she whispered her request into his ear.

At first, Simon was almost reluctant to stop what he was doing. But that disinclination faded almost immediately with the second thought that Helen hadn't been wrong yet about what he would enjoy.

Again their bodies changed position. Helen was still beneath him but she had turned around so that her head was firmly pressed against the pillows and her bottom was raised high in the air. Simon had to back off the bed while she moved, but he was back just as quick, again positioning his cock against the entrance to her delights. As he pressed back inside of her, he remembered from the sex book Josh and the guys had once found that this was called "doggy style." Also, as he again picked up his pace, he remembered from that book that people sometimes used this position to have anal sex. He wondered for a fleeting second what that was like and if Helen had ever done anything like that. Then the second passed as the urgency and immediacy of what was happening drew his complete attention.

"Oh God, oh God!" Helen moaned into the pillow as Simon rammed into her even harder than before.

The sentiment, if not the words, were echoed by Simon. Two minutes ago, he was sure nothing could've felt better but now he had been proven wrong. He could feel her tightness growing around him, even as his climax built to explosive levels. Any self-control had long ago passed, both of them were now just along for the ride. And what a ride it was, one that would carry them across the finish line only a dozen heartbeats later.

Loud cries from both of them bounced against the walls as shared orgasms caused both their bodies to quake. For Helen it was the return of memories held dear, and for Simon the realization of fantasies cherished. It would've been impossible to tell whom had enjoyed it more.

-=-=-=-

Their bodies saturated with the sweat of their exertions, Simon and Helen lay there for the longest time, interlocked with each other's naked body. It was only the chime of the grandfather clock downstairs, chiming the midnight hour, that caused Simon to lift his head from between her breasts.

"Oh shit, I'm supposed to be home by now," he exclaimed as he practically jumped out of the bed.

"Well it's too late to do anything about that now," Helen smiled reassuringly with the voice of experience. "Take a deep breath and lets see what we can do about that."

In the end, after a few minutes thought, all it took was a quick phone call home to say he'd missed the bus. All his mother was concerned about was his safety, and said that she would leave a light on for him as she was going off to bed.

"See," Helen said after Simon had laid down the receiver, "all is well. Now you even have time to take a quick shower before you go. No sense going home smelling like you've been running laps around the park."

Simon smiled at the suggestion, as if laps have ever been this much fun.

As she heard the water in the adjacent bathroom come on, Helen was almost tempted to join him and wash his back, along with anything else that needed washing. But that would make him a lot later than the half-hour he had assured his mother.

Still a little wet, Simon stepped from the bathroom two minutes later and quickly changed back into the clothes Helen had gathered up for him. As she watched him dress, the older blonde haired woman got the impression that he was suddenly embarrassed about being naked in front of her. Trying to make him more at ease, she quickly took a robe from the closet and covered herself as well.

The strange look on Simon's face continued however as she walked him down to the front door. Just before she could open it for him, Simon said he had to tell her something.

"I lied to you," he said, his tone full of emotion.

"About what?" she asked him curious as to the answer.

"When I told you about my uncle," Simon admitted, "about him being injured in the war."

"He wasn't injured?"

"Oh no, he was injured," Simon quickly said, "he has a Purple Heart and everything. He just wasn't hurt the way I said he was."

"Then why did you..." she started to say, but was interrupted.

"He told me that he couldn't..." Simon said, "that he couldn't do ... I mean what we just did, he said he ..."

"It's okay, Simon, I understand," Helen said with a smile.

"Then you're not mad at me?" Simon asked. "I'd really hate it if you were mad at me."

"No Simon, I'm not mad at you."

The relief on his face was clearly evident.

"In fact, don't you worry about your uncle," she smiled even brighter. "I can assure you I won't be bothering him again."

"Gee, that would be great," Simon said.

With that, Helen leaned forward and kissed Simon hard on his lips.

"You, on the other hand, are something else entirely," she said in her most inviting and suggestive voice.

As he stepped through the doorway to the street beyond, Simon could only hope that meant what he thought it meant. But even if it didn't, he promised himself, this was a night he would never forget.

As she watched him from the living room window, Helen found her thoughts running along similar lines. This had truly been a memorable night. The promise to leave Ryan Peterson alone had been an easy one to make because in that moment she knew that both he, and all the men who had been sharing her bed of late were now a thing of the past.

How could she go back to men who rarely satisfied her when her night with Simon had left her feeling twenty years younger. Yes, Simon would have another chance to share her bed, of that she was sure. And not only him. Just the thought of all the young men she knew in the neighborhood, some of which might be just as eager as Simon for the lessons she could teach, was enough to form a wetness between her legs.

That, she smiled as Simon disappeared around the corner, was the real golden opportunity.

END

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AnonymousAnonymous7 months ago

A long build up to the sex. I like your slow approach to his seduction. Every young man should be introduced to sex this way, especially the young men who have Oedipus tendencies. I hope in the next chapter she teaches him how to kiss her while she dominates him by straddling his face. To me that is his duty to thank her for giving him some experience that will also give him confidence with a wife.

Ynotnow69Ynotnow69about 1 year ago

I really liked this story as well. Thank you Ann

AnonymousAnonymousabout 2 years ago

Another Ann Douglas winner!!! This rating system needs a lot more than 5 stars with stories like this one!

TassieTykeTassieTykeover 2 years ago

Another cracker, seems like you make more than one of we old fogies young at heart again.

AnonymousAnonymousalmost 3 years ago

Oh Ann, yet another jewel! You perfectly capture the innocent eagerness of a virgin lad. At the same time you draw with such credibility the portrait of an elderly woman with all of her breathtaking sexuality intact. What fun! I am an old man now but you give me coal I need to stoke the old firebox...Thanks for sharing. I hope you write from equal parts your experience and your imagination. Kalodin

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