Student and Teacher Ch. 11

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And that’s how it began. Almost every night, Damon found himself in Nan’s room—and her bed—as she snuggled and kissed and made each other come. After a week or so, Damon took the initiative to slide from her breasts down to her delta, where—after an initial protest—she allowed him to lick her to a shuddering climax. As before, he continued to lick her after her climax had started, extending it for minutes while seizing her bottom with his hands and giving them a good squeeze.

It took Nan a good two weeks to venture down to Damon’s cock and place it in her mouth. She wasn’t at all sure how much of it she could get in, but Damon assured her that deep throat was not all that much to his taste and that she should just manage whatever she was comfortable with. That was reassuring to her, but then there came the matter of the payoff. She was not at all comfortable with his coming in her mouth, and so she worked out a system whereby she stimulated him orally, then, when she sensed his culmination was approaching, she finished the job with her hand. Sometimes she was spattered on her face by his emission, since she developed a fascination with witnessing it up close and personal; but she seemed to enjoy the sensation of the hot, thick liquid landing on her cheeks, chin, and forehead. But immediately afterward she rushed out of bed to wash her face, coming back to bed sheepishly to apologize for her shyness.

Usually they settled for one climax each, but sometimes they did manage two—or, rather, Damon managed to coax a second one out of Nan, with a suitable interval of cuddling in between.

All this was not entirely satisfactory to Damon, but he made sure not to show his feelings to Nan. When he had once suggested that they “go all the way,” she gave him such a look of terror that he inwardly kicked himself for being such a brute.

She clung to him like a little girl seeking solace from her father, saying, “I’m not ready, Damon. Please don’t rush me.”

“I won’t, dear. I promise.”

After a pause she said in a small voice: “I’m scared.”

“I know you are, and you have every reason to be. It’s a big deal for a girl.”

“You’ve had a lot of girls, haven’t you?”

“Not that many.”

“I hope you don’t get too frustrated.”

“Don’t worry about it. Everything’s fine.”

But, as Damon came home night after night without having probed Nan’s body the way he wished, he began taking it out on Iris. Even when it was not his night to be with her, he would storm back into the house, shed his clothes, and pound the poor woman mercilessly, front and back, until he had worked off his aggravation. After one such night, she registered her own complaint.

“Damon, dear, you’ve got to stop this. You’re really working me over.”

He was startled by her comments, but suddenly realized the truth of his words. “Omigod, Iris, I’m so sorry! I didn’t mean to rough you up!”

“You didn’t rough me up, exactly,” she said, although in fact he had.

“It’s just that she—” He couldn’t go on.

“She’s still reluctant?”


“Well, dear boy, give her time.”

“It’s already been a month! How much more time does she want?”

“You can’t rush these things. She’ll come around.”

“God, it had better be soon!”

Iris looked critically at her lover. “Have you bothered to tell her what you feel about her?”

“What do you mean?” he said sulkily.

“I’m beginning to think that she needs you to express your feelings toward her before she’ll go ‘all the way’ with you.”

“I’ve said lots of times that she’s wonderful and fabulous and stuff like that!”

“That’s not what I mean. I think you know exactly what you need to say. That is, if you really feel that way.”

Damon paused in self-reflection. “I think I do. In fact, I know I do.”

“Well, then, tell her.”

“You won’t mind?”

Iris gave him a surprised look. “Why should I mind?”

“It’s just . . .”

“Damon, I know what your feelings are for me. If you feel the same way for her, well, that’s all to the good. It just shows what a big heart you have.”

“You mean that?”

“Of course I mean it.”

“Oh, Iris, you’re the best!” Damon said for the hundredth time, wrapping her so tightly in his arms that she claimed he was squeezing all the breath out of her.

And so, the very next night, as they were cuddling after having given each other a pretty powerful climax, Damon stroked Nan’s hair tenderly and whispered in her ear:

“Nan, dear, I love you.”

A little shudder ran through her. For a moment she did nothing, although Damon felt her whole body stiffen. Then she slowly raised up her face to his. He could see her eyes brimming with tears.

“Do you?” she asked in a little-girl voice.

“Yes, dear, of course I do.”

“Since when?”

“Since—since almost the moment I met you!” he said impulsively.

She gave him a warm, benevolent smile that caused his heart to flip Anadolu Yakası Escort over. Then she said, with the solemnity that only a virgin can manage: “I love you too.”

Damon wasn’t so crass as to think that, after his (quite sincere) profession of love, she would immediately spread her legs and let him go into her. Instead, he was quite content with continuing to snuggle. After a while he snaked his hand down to her sex and began a slow, gentle stimulation that she accepted as a kind of fitting pendant to his words. The climax that came over her after several minutes was quiet but incredibly intense, and in the course of it she had climbed on top of him, his cock sliding between her legs as she closed her thighs around it.

When Nan had come down from her sexual high, she whispered these words in Damon’s ear: “I think I’m ready.”

It was as if an electric jolt had gone through his body. For a moment he didn’t even realize the full significance of the words. Then he whispered back:

“Are you sure?”

It took her more than a few heartbeats to say “Yes.”

“Are you absolutely sure?”

“Yes!” she cried almost violently. Then, more quietly: “Yes. Please do me.”

She made no move to get off of him, so he asked: “Do you want to be on top?”

She looked at him quizzically and said, “No, of course not!” It was as if he’d asked if the earth was flat. She promptly flopped off of him and onto her back, saying: “You be on top.”

Damon didn’t immediately mount her. Instead, he paid due homage to her glorious breasts, sucking and kneading them with such devotion that she giggled with delight. But then, when he rode up her body and got into position, he was dismayed to see a frightened look on her face.

“Just relax, dear,” he said. “Don’t tense up.”

As his cock entered her an inch or two, she let out a little whimper—not of pain, but of the anticipation of pain. And he quickly came up against that silly obstacle that he knew he would have to break through, regardless of whatever anguish he might cause. He hadn’t had a virgin since high school, and had pretty much forgotten what a traumatic experience this could be for a girl.

And so he plunged on in.

The moment he did so, Nan expelled a sharp cry as if she’d been punched in the stomach, and tears sprang from her eyes. Damon cursed nature for devising this ridiculous and seemingly useless membrane (what purpose did it serve anyway?) and tried to make Nan as comfortable as possible.

“You need to raise your legs and bend your knees, dear,” he said.

“Why?” she asked.

“It’ll make it easier for me to go in.”

She followed his advice—and seemed to find the process a little less painful. But now Damon faced a pair of further quandaries. Should he pump her hard and fast, so that he could finish sooner and make her agony shorter even if more acute, or should he go slow and easy, even at the risk of prolonging her pain? And should he go in only a few inches, or should he proceed all the way in? He knew that it wasn’t merely the rupture of her hymen that was affecting her, but the mere presence of his long, thick cock in her vagina—but at some point she would have to get used to the sensation of being truly filled up, so should it be now or later?

He decided to go at a moderate pace but all the way in—but when he did so, he heard her emit a choked cry that wrung his heart. She was clutching his back spasmodically, and he tried to silence her cries by pressing his lips against hers; but he could still hear her moans, proceeding in rhythm with his thrusts. For his part, the velvety softness, warmth, and wetness of her pussy was so rapturous that he came almost at once; but he selfishly held back, extending the experience even if it meant a little more pain for his cherished partner.

But he couldn’t hold out long, and he was soon flooding her with his abundant seed, expelling moans of his own. Then he collapsed on top of her, physically and spiritually spent; and only when she silently indicated that he should get off—and out—of her did he roll over to the other side of the bed.

Once he had recovered, he turned to peer at her. Her face was a grimace of misery.

“That hurt, didn’t it?” he said.

“No, not that much,” she lied as the tears continued to flow down her face.

“Oh, Nan, I’m so sorry!” he exclaimed as he seized her and plopped her on top of him. He did his best to wipe the tears away with the bedsheet, and his clumsy efforts had her laughing shakily.

Then he realized that certain other things had to be done.

“We’d better clean you up,” he said decisively.

And with that, he simultaneously got up from the bed and caught her up in his arms. He knew that the bathroom lay just down the hall from Nan’s room, and he was opening the door to her room when she cried in alarm:

“We can’t go out there naked! There are other people in this house!”

“I don’t think there’s anyone Bostancı Escort out there,” Damon said with unwarranted confidence. As it happened, there wasn’t anyone—at least, no one who saw him dash into the bathroom with Nan in his arms.

He put down the lid of the toilet, placed her gently on it, and took hold of a washcloth, which he soaked in water. As she looked up at him, with the trusting gaze of an obedient little girl, he parted her thighs and began washing the blood away. Some had already dried on the inside of her thighs, and he made sure to tidy it up while also mopping up her cleft, where bright red blood mingled with his own emission was leaking out.

As he was finishing, she pointed at his own groin and said, “There’s some stuff there.”

He looked down at himself and said, “Oh, yeah,” quickly wiping away the red streaks on his cock. He was going to pick her up again and take her back to her room, but she said peremptorily, “I’m quite capable of walking,” and flitted back to her room before anyone could detect their presence.

They fell back into bed, resuming what had become their usual position—Damon lying flat on his back, and Nan covering most of the left side of his body with her own. It was a position that he and Iris had taken many, many times—and, as he reflected on how much he loved Nan, he also realized that his love for Iris was unabated. In fact, in some strange way this new love had actually increased his love of the older woman. He had no explanation for it; but there it was. Maybe it just showed the truth of Iris’s comment about his “big heart.”

As they continued to cuddle, the inevitable happened—to Damon, anyway. And Nan noticed.

“You—you want some more?” she said shyly.

“We don’t have to,” he said gallantly. The last thing I want to do is to cause this girl more pain.

“I think I can manage,” she said with what Damon thought was reckless bravery.

“Maybe you could ride me,” he suggested.

“What does that mean?”

He smiled at her inexperience and explained. As he did so, she frowned intensely as if digesting a difficult treatise on conic sections. Then she sought to put her new knowledge into action. As she rose up and squatted on Damon’s legs, she peered at his growing cock, took it in her hand, and began the delicate process of inserting it into herself.

“You don’t have to go in all the way,” he said, even though he knew it would be difficult for her to stop halfway.

She bit her lower lip in concentration as she got the tip of his cock into her. Then, unexpectedly, she slid down on it almost to the root, letting out a gasp of surprise.

“Easy!” he said. “Not so fast.”

But the die was cast, and she figured that nothing was to be gained by stopping now. She continued to lower herself onto his shaft, and pretty soon it had magically disappeared into her.

To Damon’s relief, a broken smile spread over her face—perhaps more a smile of accomplishment than of pleasure. She herself looked down at the incredible sight of a cock fully lodged in her pussy.

“Can you . . . go up and down now?” he encouraged.

She had to put her hands on Damon’s chest to do what he asked, but presently she got into a suitable rhythm. He could still see a few streaks of blood as his cock emerged from her cleft, then plunged back into it. At one point Nan arched her back, as if glorying in the sensation of coitus, and that had the heart-stopping effect of raising her breasts and making them seem to swell to even larger dimensions than they were.

There was no way Damon could hold out very long. He loved this position because it allowed a mesmerizing look at his entry into his partner, not to mention the sight—and feel—of her magnificent breasts. And his hands weren’t idle, as he seized her bottom and guided her as she bounced up and down on his cock until he shot his second wad into her, causing her to squeal with delight.

There was a later session when he licked her pussy until she came, lapping up both her juices and his own in the process.

By now both were feeling pretty tired, but presently Damon seemed to get a second wind. It didn’t hurt that, in their next cuddling session, Nan took gentle hold of his cock and played with it as if it were a toy designed specially for her own enjoyment. And that had a predictable effect.

She now seemed to regret her teasing of his member. Looking wistfully at him, she said, “Oh, Damon, I think I’m too sore for another round. Could I finish you with my hand—or my mouth?”

It must have been some imp of the perverse that led Damon to say: “Could we try something else?”

“What?” Nan said.

When he whispered his desire into her ear, she stiffened at once, but otherwise said, in a quiet but shaky voice: “You want to do that?”

“Only if you want to.”

“You’ve done it with other girls?”

“Yeah—a few.” And a lot with a woman named Iris.

“And they liked it?”

“Some of Ümraniye Escort them did.”

“But it’ll hurt, won’t it?”

“I guess it might. But lube will help.”

“What lube?”

He had previously noticed something that would serve without his having to go back to the bathroom. “That hand lotion should work.”

But as she fell silent, digesting all this information, Damon said, “We don’t have to, Nan. I won’t want to hurt you anymore. We can do something else.”

“Hey, I can take it!” she said with sudden agitation. “I’m not a weakling!”

“I’m sure you’re not, but—”

“Go get the lube, then!” she ordered.

He looked into her face, which was a little flushed—maybe from excitement, maybe from apprehension, and maybe from outrage that he had thought her unable to endure this new form of intimacy.

“Okay, ma’am, I’m yours to command,” he said flippantly as he got off the bed and got the lotion.

She reached out for it, but he said, “I’ll put it on.”

That made her blanch, eyes widening a bit. It struck him once again that so many women seemed more troubled by having a man’s fingers probe that delicate area than his cock.

She flopped onto her stomach and buried her face in a pillow, to make sure she didn’t see the process happening. But she did let out a little squeal as his fingers coated her anus with the cold fluid.

She was about to get on all fours—the preferred way of performing this act, she thought—when he told her to lie flat. He gently draped his body over hers and tentatively directed his cock toward the forbidden orifice. She moaned a little but remained motionless. And so he entered her inch by inch—and noticed that her eyes got increasingly larger and her mouth dropped open in a silent cry as he did so. This time he was certain that going into her all the way was unwise, and so he stopped about two-thirds of the way in. But even that was causing Nan to breathe raggedly, with a little whimper emerging from her throat from time to time.

Damon knew that only practice would make this procedure relatively painless, and so he began the slow process of thrusting in and out of her, seizing her breasts as he usually did with Iris. Nan seemed to go entirely passive, and Damon felt that was probably the wisest thing she could have done, even at the risk of feeling as helpless as a sex doll. As his own climax was approaching, he slid a hand down to her cleft and began stroking it—an act that seemed to take her by surprise, if the little high-pitched cry she let out was any sign. By this time he was pounding her pretty hard, and her eyes seemed to be glazed over; and when he came, he saw with delight that she herself was experiencing an orgasm that caused her entire body to shudder uncontrollably, almost causing him to slip out of her. But he was determined to bestow this new opening with all the seed that was in him, and he remained plugged fast in her even after both of their paroxysms were long over.

Only then did he pull out, as tenderly as he could; but his final emergence from her, he knew by experience, was always a little painful, and sure enough she groaned a little as he came out.

They both lay there, he on his back and she on her stomach. Between staggered breaths he asked:

“Did that hurt?”

“Yeah,” she said into her pillow.

“I’m sorry.”

“It’s okay. But I didn’t expect to—you know—” She didn’t need to say it. I didn’t expect to have an orgasm while enduring all that pain. “A really strange feeling.”

“Well, at least you got some enjoyment out of it.”

Suddenly she rolled over and nestled against his side. “More than just ‘some’!”

“That’s wonderful.”

They both lapsed into silence. Then she said, in that little-girl voice that was so entrancing to him: “I’m glad it was you.”

His heart expanded at those simple words. “I love you so much, Nan.”

“I love you too, Damon.”

And with that, they fell asleep.


Damon didn’t see Iris until close to dinnertime the next day, but the reason for his absence from home the preceding evening was not in doubt. When the young man did wander in, drifting into the living room as if walking on a cloud, Iris gave him a wry glance and said:

“So—you rang the bell last night?”

Damon stopped in his tracks and gave his beloved a reproachful glance. “Iris, that’s not very respectful. It was one of the most heavenly experiences of my whole life—and hers too, I hope!” He chuckled reminiscently. “Almost as nice as when we, um, first . . .”

“Yes, I suppose so. But when do I get to meet this paragon of young womanhood?”

Incredibly, Damon had neglected to bring Nan over to the house in the month he had gone out with her. He had made all manner of excuses (“The place is really pretty messy”—which it wasn’t; “Brad’s kinda shy around women”; etc., etc.), but he realized that the time to bite the bullet and introduce her to Iris had come. Not that he felt the need to explain their unorthodox relationship right away, or ever: a girl like Nan was likely to freak out if she knew what went on under this roof.

“I’ll bring her over pretty soon,” Damon said. “But it’s going to be tricky. You won’t say anything when you meet her, will you?”

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