The First Ninety Days Ch. 12

Day 55

Jon awoke on Saturday morning with a challenge set for himself. What Caitlyn had said—about bringing a partner to orgasm using only the appendage intended by nature—had stuck with him; he wanted to see if he could do it. And today was Saturday; aside from Marissa Helmsley's wedding to Rob Caruthers, which would require their presence (or, technically, Caitlyn and the harp's presence; but the thing was too big for her to move alone) at 2 PM, they had nothing to do at all. This was the perfect time for some good sex.

Assuming I can make it good.

Caitlyn, of course, slept like a stone; she didn't waken as he extricated his arm and then rolled her onto her back. She was limp and trusting in his arms, her mouth slightly open to admit small, ladylike snores. He clasped her cheek with his hand and kissed her forehead. There were some whose instincts would be to take advantage of her vulnerability; his were to protect her, to shelter her with his efforts and love and his body if need be, to keep her safe from the storms outside. He loved her. He could do nothing else.

In spare moments over the week he had researched this dilemma. The theory was obvious: to bring her as close as he could to orgasm before penetrating her, and then to let his cock do the rest. He knew to slide up her body a little further than normal, to put more direct pressure on her clit; and he knew from Monday's watershed discussion that she was incredibly turned on by his presence bearing down on her. Beyond that was timing, luck and speculation. How close could he get her; and how much of that orgasmic tension would fade away while he maneuvered himself up to penetrate her? How quicklycould he do that? He felt equal to the challenges... But he knew himself well enough to know that it was unearned confidence, that he was flying more or less blind here. Several sites had suggested throwing her legs over his shoulders for the deepest possible penetration and G-spot stimulation; he was sure they were right, but thought it might still be smarter to go with what he knew. After all, despite her flexibility, he didn't think he could rest allthat much weight on her if her legs were up like that—not without hurting her or yanking something out of shape.

Still, this was the kind of challenge he thrived on.

He planted gentle kisses around her brow, her nose, her cheeks, her chin; when she didn't waken, he began to move around to her ear, applying lips and tongue to the delicate ridges and folds, to the pale lobe of flesh below. He did it gently; he had suddenly realized that it might be better if she woke up mid-way through, already turned on before she was even conscious. Though she still slept, he could see that his efforts were having an effect; her breathing was growing steadily deeper, and every now and then she breathed out a sigh and moved a little.

She didn't wake up until he had already paid some homage to her breasts and was halfway down her stomach. Her breathing gave a sudden hitch and she moved convulsively, as though being startled out of sleep; a moment later, her hand landed on the back of his head. "Good morning," she said.

"Good morning," he said in between kisses.

"I was having the most remarkable dream," she said, a smile evident in her voice.

"Good," he said in between kisses. "Just lie back... and let me... make them... come true."

"Mmmmm," she said, a verbal smile. Her hand tightened in his hair.

When he reached her hips, he bypassed her privates entirely, knowing she would have expected him to go there; there was something to be said for anticipation. Instead, he began to kiss her inner thighs, down one leg and up the other until making his procession down to her feet. Besides, she was on the tail end of her period, and, no matter how brave he acted or how he steeled himself, he just wasn't a fan of that salty taste.

As he began to kiss around her ankle (her hand was long gone by now, of course), she said, "You certainly seem to like it down there."

"Well... I guess I do. Anything wrong with that?"

"Umm... They're kind of dirty."

"Why? You wash them when you shower. They smell just fine. Yoursocks don't smell when you take them off, nor do your shoes."

"Yeah, but, Jon—"

He wasn't going to let her hesitation stop her in this case. He took her big toe in his mouth.

She liked it. He could tell, she liked it—her words cut off mid-sentence with a moan, and he saw color flood into her cheeks. Her toe tasted like her fingers did—warm skin with its faint reddish taste—but was a little large for his mouth, so he began to transfer down the row. (This little piggy...) Her second toe curled in his mouth like a big comma, the bulb fleshy and light, with plenty of crevices and folds to explore. Her big toe brushed against his cheek, and from his vantage point here as he knelt at the foot of the bed he could see her pussy beginning to open like a flower, the outer lips parting and the inner petals beginning to show themselves—a sure sign of her arousal.

When he had reached the last of her toes, he was tempted to try using his teeth, but some instinct made him resist; perhaps he decided he'd pushed enough for one day. Instead he began to kiss back up her body, switching from leg to leg, once again bypassing her pussy in favor of her breasts. He spent longer here this time, kissing over every inch of them, only leaving them when her nipples were fully erect and he could sense that he was no longer thrilling her in any meaningful way. He was here to build her up, not waste time.

As he approached her pussy for yet a third time, her legs parted to welcome him, but once again he took his time. The heat and scent of her arousal were palpable, but he kissed around her legs and the skin of her crotch, concentric circles that slowly narrowed towards that single velvet spot. He thought about going for her anus, or at least her perineum, but decided she'd been stretched enough for one day. He kissed up and down her outer lips, and then up and down the inner ones, caressing them with his tongue; and then he was there, and, abandoning pretense entirely, he latched his lips in a circle around her clit and sucked.

Caitlyn gave a yelp; her whole body jerked, her knees coming up around his head. Simultaneously her hands landed on his head and shoulders, locking him in place. He was starting to learn some of the signs of her impending orgasm, and many were there—he couldn't actuallyfind her clitoris, it had retreated so far under the hood, and her breathing had gone raw; the flesh of her pussy had darkened in color, and her legs were tense against his body. And her whole body, not just her face, had begun to flush, a sure sign that she was getting close. He added a rubbing element with his tongue, licking up and down in the little patch of flesh he had staked out, and she began to moan.

"Tell me when," he said, taking a moment away from her body. "Tell me when."

"Keep going. Keep going. Oh, oh, oh... Jon, keep—"

This was the critical moment. As her pitch spiraled higher and her body continued to tense, he knew that if he wanted to penetrate her, the time was now. But could he compensate for the sudden disruption in her pleasure?—she wouldn't stay aroused for very long, maybe only seconds. If he was going, he needed to go quickly and he needed to go now.

In retrospect, he wasn't sure how he did it; maybe Caitlyn helped him, somehow, despite her pre-orgasmic delirium. All he knew was that one moment he was hunched between her thighs; the next he was up over her, guiding himself in. He sunk to the hilt in one go, and then moved himself up until his shoulder covered her face, changing the angle to put more stimulation on her clit. Caitlyn grabbed him by the butt and pulled, as though trying to consume him bodily. "Jon— Jon— Do it, do it, oh—"

Three quick strokes, and she was there.

He felt the tremor under him, watched her body seemed to stretch and tense like a spring; then her face went slack with the relief, and he felt the firm clenching of her pussy around his shaft as she shuddered under him, her arms and legs losing their strength, the tension in her face melting into an expression of exhausted joy. The squeezing must have felt remarkably good to him, but he didn't notice; he was too busy watching her come.

Her eyes closed and she relaxed back onto the bed; he kept himself occupied kissing her neck, her ear, her face, even her eyelids until she opened them again and smiled up at him.

"Wow," she breathed.

"I love you too, baby," he said.

"Oh, I love you so much..." She reached up to kiss him. "That was... I see what you mean about... About wanting me to cum."

He smiled. "It was fun for me too. Most of the time I'm down there when it happens, or coming too; I don't get to watch."

"Yeah, no kidding. Remember what Alice Larson said during the session we spent talking about sex?"

"Umm..." said Jon, casting back through his memory. "Some of it." The other college-group kids had been surprisingly mature about it, even Harold—Jon had half been expecting titters and suppressed sniggering.But then, we're none of us eleven anymore. Or even fifteen. "Everybody was looking at us funny."

"Well, weare married," she said. "The only ones who are supposed to have that knowledge, besides Mr. and Mrs. Larson themselves."

"Fair enough."

"What she said was that watching someone orgasm is one of the most intimate experiences a person can have, because you're not completely in control of yourself when you come. Your face and body do things that aren't really voluntary."

"Like having an orgasm."

She giggled. "Yeah."

"No wonder everyone looked at us funny," Jon said, "they were all wondering what we knew."

Caitlyn giggled. At other times she might take offense at this thought; right now, today, she seemed remarkably mellow. Certainly they were having a philosophical conversation while he was still buried to the root inside her.

"I like that idea," Jon said. "I remember thinking it was a good point. It's like a reward for going through all that effort: you get to meet them at the one moment in time when they're completely vulnerable."

"Yeah, and it's something you only ever share with your lovers, so it really is intimate. Especially if you're one of the people who waits until marriage."

Jon had once cursed his luck at never meeting a girl who was willing to put out. Now, here, with this viewpoint, with this woman, he was actually rather glad. "You're the only person who will ever get to watch me come. You're the only person who will ever know me that way. And I'm the only person who will ever knowyou that way either."

She kissed him. "And that's why I like it when you come inside me without me cumming too. Because I get to just... Experience it. To know you. To really know you, at your most private and intimate moments."

He kissed her back, feeling the warmth of his feeling for her rise inside him. "I love you, Caitlyn."

She wrapped her arms around him, drawing him down to kiss him. "I love you too, honey. Now, about this getting-to-know-you thing..." She wiggled her bum around his hardness. "Isn't there something you're supposed to do when we're like this?"

He pulled his head back to look at her. She was wearing a wicked grin and she kissed the tip of his nose. "Come on, baby. Make me your woman."

It was different now that she had come—a little looser, a little wetter, not quite as warm—and he had a hunch that this might not be entirely pleasurable for her, and maybe not very comfortable either. Nonetheless she cooed her acceptance, drawing him down, pressing up to meet his thrusts, whispering in his ear how good he felt, how much she loved to have him inside her. He held himself up on his arms so that she could see his face; they kissed each other's lips and ears until he came, groaning, holding himself deep inside her, unable to move, held immobile by the force of his pleasure as it surged up through his cock, rushing out into her, like love made tactile and physical; she moaned as it rushed through her, and he imagined his spend inside her, clinging to the folds and crevices around her cervix, pooling inside her body. And as he settled against her again she sighed in deep satisfaction, completely content.

When he woke up again he was soft but still inside her, lying on top of her, wrapped in her arms and legs. She too was asleep, and seemed to bear no discomfort from his weight. Still, it wasn't entirely a comfortable position for him; his neck had a crick from bearing too far forward, and his arms were numb. Despite her protests, he extricated himself from her, rolling onto his back and drawing her with him; unusually, she followed, sprawling out over his chest.

"What time is it?" she asked.

"Not time to get up yet."

"We have to leave at one."

He turned his head to glance at the clock on his side. "It's not even ten-thirty."

She sighed. "Soon."

Silence for a time.

"We'll have to shower."

"Probably."

"I guess I should take extra pains with my feet from now on."

"Might be wise."

"Well... If you really want me to."

"Didn't you like it?" He raised his head to look at her.

"Well... It was... It felt nice, yes. But it was... Weird, too. I mean... They're my feet. I've had them, my whole life; they've just been there. I'm not really used to the idea that they're supposed to be made to feel good."

"Fair enough."

"And besides... I wasn't... I was a little nervous."

"Oh?"

"Jon, Ineed my feet. What if you had somehow... Umm. Damaged them?"

On the one hand, he felt a little offended that she thought he could be so careless. On the other hand, if someone was fooling around withhis feet... They were certainly delicate; he certainly needed them. The possibility of injury might indeed put a damper on his enjoyment.

At the same time, though.... "So, let me get this straight: you want me to dominate you, and take control of the sex, and do whatever I want... As long as it's also what you want?"

She sighed. "Yeah, itdoes sound kind of stupid that way, doesn't it."

He rolled to his side so that he could see her. "On the contrary, that's the only way it sounds sane. I would be worried if you felt any different."

Her eyes lit up. "So you'll do it?"

"Well, let's not gothat far. That fast. Caitlyn, it still doesn't sit very well with me."

"Why not? You know I want it. And you know you want it too."

"Wantwhat? The potential for abuse is just too... I mean, we haven't eventried it and we've already gotten to places where you feel uncomfortable."

Her face grew resolute. "What if I gave you blanket permission. What if I said, 'Tonight you can do anything to me, and I promise to like it.' ...Or at least let you." A new thought: "Ooh, what if I faked it!"

He winced. "That would be an even worse idea. Caitlyn, weren't we just talking about how orgasm is intimate preciselybecause it can't be faked?"

"Tell that to about a million women from here to Eve," Caitlyn said.

Jon winced again. "I didn't know you evenknew about that."

"You find out interesting things on the Internet," said Caitlyn. "And until school started I didn't have much to do. But in any case, that's not what I meant."

"No, it's completely what you meant," Jon said. "You were willing to lie to me to make me happy. And, while it's the thought that counts, I really wish you wouldn't do it." He touched her face gently. "No one's worth that. Definitely not me."

She held his hand against her. "It's because you say those things that you're worth it. But you're right. I won't."

He leaned across the bed to kiss her, and for a moment there was silence; and when they stopped, there were more arms and legs wrapped around each other than before.

"But what if... Jon, what if we established rules?" She took her hand away for a moment to comb a strand of hair from her face. "What if we said, 'Okay, here's what's allowed and here's what isn't.' What if we limited those activities to... I mean, that's kind of what happens anyway, right? Sometimes, like today, we experiment; sometimes, we just do it the normal way. ...Like today too, after we were done experimenting. We can say, 'No experimenting when Jon's dominating me.' "

"That would work," he said, "except that Jon dominating-you-kind ofis experimenting in itself."

"Okay, so, only one kind of experiment at a time," Caitlyn said. "And also, what Zach and Christa were saying about No not meaning anything... And, if things go the way they could, then maybe 'No' would be flying around a lot without it beingmeant to mean anything..." She was turning very red by this point, but she plowed on. Jon wondered just how deep this non-consent fantasy went with her. "Maybe we should establish something where it reallydoes mean No. A, a word, or maybe a sentence. And if I say it, you know that I'm actually uncomfortable and not just faking it."

Jon nodded. "A safe word."

"Yeah. Something I'd never say normally, like... I dunno. 'There are petunias in my meatballs.'"

Jon laughed. "That might be a bit over the top. But it's a good idea to have one. Having rules is the only way to keep things like this safe."

She grinned. "So you'll do it?"

"How can you be so eager about this and so nervous about foot play?" He kissed her before she could answer. "I can't make any promises, sweetheart. But... As long as it seems safe, and like nobody's going to get hurt, I'm willing to look into it."

She squealed and dove into his arms, kissing him madly.

"Umm, Caitlyn, err. Not right now," he said. "I'm not gonna do itnow."

"No one said you had to," she said, in between kisses. "I'm just going to show you how much I love you." And she began to trail kisses down his body, aiming for the member between his legs that was even now beginning to stiffen with heat.

She took her time, kissing around his ear and his neck, and then made an unexpected detour: she stopped to play with his nipples. She had never done this before; it had never occurred to them to try it. But it became instantly clear to Jon that this was something she should try again; and, he wagered, moments later it became clear to her as well.

"Hmm," she said. "He seems to like it."

"Yeah..." he breathed. It was unlike anything he had ever felt before—the warm sensation of her mouth and tongue; the deep pulling feeling that seemed to stretch through his body straight down to his cock; the feeling of her head against his chest, her hair in a shower over their skin. He cradled her closer, urging her on, and she did not disappoint; she began to lick his nipple rhythmically and rapidly, each one eliciting a moan.

"Hmm," she said. "I wonder if, maybe, I can make you come one day just by doing that."

"Darned if I know," he said. "Maybe." It seemed fairly unlikely—he didn't think he wasthat sensitive—but stranger things had happened. Besides, why discourage her from exploring.

He heard her grin: "Should I try sucking onyour toes now?"

Honestly, the thought did not turn him on as much—but mostly because his feet weren't nearly as sanitary as hers. "They're kinda grody."

"Oh."

"Maybe you should wait until after my next shower." He wouldn't mind experiencing it, but hedid mind the thought of inflicting his feet on her. That went beyond cruel-and-unusual.

She smiled and gave his nipple another kiss. "Always good to know my man's looking out for my best interests."

When he came she suspended her mouth over his cock as he'd suggested, using the roof of her mouth to control the splashing; he felt her warm breath ghosting over the head of his cock, her hand firm around his shaft, and gave a great sigh of contentment. There was something to be said for intense sensation, but something also for a warm, relaxing orgasm at the hands of his beloved. He wished he could do that to her; he wished they could ever reach a point where it wasn't a big production for her to come. He wished they could reach a day where he could simply crawl back up to her, as she was doing now, and be thanked with nothing more than a kiss.