The First Ninety Days Ch. 13

"Hmm." She pretended to think it over. "But I'm here every day."

"So, every day's like a Valentine's Day to me," he said.

"So, you mean I should send a Singing Valentine to youevery day?" she said.

"No!" He laughed. "That's quite alright, thanks. Besides, I think we'd go bankrupt pretty quickly."

"True enough. Yours must've been evenmore expensive; it included flowers." She gestured to the bouquet she'd gotten, which (for once) looked exactly like the one he'd picked out of the brochure, and which was now resting in a vase. "How did people like it, anyway?"

He told her about it as they drove, and she told him hers. Evidently, she'd been in the middle of her Jazz Theory class, and many of her classmates (not to mention the teacher) had taken it upon themselves to accompany the performer. Then, somehow, they got into some improvising, which of course was the real heart of jazz anyhow; it was some fifteen minutes before the deliverer managed to get out again, but he seemed to have been quite entertained. Caitlyn, of course, had turned bright red once the mushy-gushy song started coming out. "God Must Have Spent A Little More Time On You. Jeez. Laying it on a little thick there, o hubby of mine."

Jon shrugged. "It seemed the best option for causing as much chaos as possible. Not to mention that it's also true."

"Have youseen that music video? You do know it's supposed to be a Mother's Day song, right?"

"Really? With that level of smarminess?"

"Well,I didn't do it," Caitlyn said.

"Good," said Jon. "I'd be extremely concerned if you turned out to have somehow been a former member of 'N Sync. It would certainly explain why you hate them, though."

"Yeah. I was their sixth member. Of course, that was before the sex change."

Jon stared at her. "...Uhh, okay, 'Sad Valentine's Day' moment there."

Caitlyn smirked at him. "Jon, look at the road. You're driving."

Their dinner was not at Rebecca's Parliament. This was not for lack of trying; the maitre d' had informed him that they had been booked solid since November, and that (furthermore) the guest list was so predominantly female that Jon would feel completely out of place. "You know the term 'sausage-fest'?" the woman had said. "Yeah, we have like the opposite problem here." So, instead, Jon had looked up the nicest fondue place he could find. It was unusual, it was exotic, he knew Caitlyn had never been before, and he figured she'd love the richness of the food. Besides, he knew he could sell her on anything that involved a dipping-pan full of melted chocolate for dessert.

It was just as good a surprise as he'd hoped. Caitlyn was delighted with the food choice and particularly seemed to enjoy getting to spear things with the pronged fork. The presence of cheese didn't hurt either. They traded bites over the pot, giggling when one or more of them accidentally dropped something into the dip.

Of course, Caitlyn didn't eat much.

"What's wrong? Does something in the food not agree with you?"

"Silly." She flashed him a radiant grin. "I'm waiting for dessert. So hurry up and finish," she said, "so that we can get to the chocolate!"

Jon gave a theatrical roll of his eyes. "I might've known."

"And then, after the chocolate... We can go home," she said, her voice husky now but no less excited, "and... I can give you your next surprise." She caressed his cheek with a finger; the touch felt electric to him.

"Hmm," said Jon. "Should I get the check?"

"Silly," she said, "not before dessert. But, umm." Her grin widened. "Very soon after it."

Jon rolled his eyes again and signaled for the dessert course.

He had planned to basically attack Caitlyn once they got home, but she fended him off. "Nope! Nope, no no no no. These are very special and fancy clothes, Jon. We gotta get out of them and hang them up properly. Sheesh, what kind of a barbarian do you think I am." She stuck her tongue out at him.

"Don't point that at me unless you plan to use it," he said, echoing her comment. And Caitlyn turned right back to him and gave him that roguish grin: "What makes you think I don't?"

So Jon very carefully got out of his tie and shirt and slacks, and stored them very carefully back in the closet. He had just managed this when Caitlyn reached over and tugged on the leg of his boxers. "Those too," she said. And Jon, starting to get an idea of where this was going, took off his boxers and his socks and got totally naked.

"Should I fold these up too?" he joked, and went across the room to dump them in the hamper.

"Okay," she said, "all done." She closed the closet door and turned to him, bare as the day she was born. She had shaved recently; except for the patch between her legs, she was smooth and completely bare. Her long brown hair was loose and tucked behind her ears, a few tresses already working themselves loose; some of them cascaded down her shoulders, drawing out the pale perfection of her skin. Though long, her hair did not hide her nipples, nor her large puffy areolas, so tempting to the tongue. Her eyes were wide and luminous, the midnight color of a moon-drenched sky; he could spend years just staring into them.

"Now," she said, crossing the room to him. "Where were we?"

"Something like this," he murmured, and drew her lips up to his.

They stood entwined in the dim light, kissing, she on her toes and he bending down to compensate for the difference in height. His hand was between her legs, feeling the warmth and wetness between, and hers were between his, stroking him into erection; her other arm looped around his waist, his skin burning with her touch. He went to his knees to suckle at her breasts. It was a new dimension for him, to be shorter than her like this; her breasts were at the perfect level for his face. Her mouth opened in a silent 'O'; one arm circled his shoulders, the other hand ruffled his hair; and still he kept his hand busy between her legs, encouraging her continuing arousal.

Soon she was drawing him up, beckoning him. She leaned back onto the bed, her feet still dangling over the side, and drew him between her legs. They had never done it like this before, but the mechanics were obvious; he slid inside her and then bent over to kiss her. They moved together, she rising to meet his gentle thrusts with her legs now encircling his waist, her ankles locked. When he came it was silent, almost anticlimactic, but that was good in its own way; they kissed, staring into each other's eyes, whispering their love for one another, whispering the pleasure of their bodies to each other, enjoying the gentle blush of orgasm as his body pumped out its seed within her. He had cum, but he felt, not sated, but rather whetted for more, ready for greater play. And he could tell that she felt the same way.

"My last surprise," she said to him, "is one that had to wait until now."

"Oh really," he said, smiling. Considering where they were—considering he was still balls-deep inside her, her legs still up around him—it was pretty obvious what the surprise would concern.

"Yes," she said. "I have been thinking, and I've looked it up on the Internet... And... If you want to try, umm... Doing it in my, umm, my tush... Well, I'm willing to give it a try."

He realized his eyebrows were far above his hairline and made a conscious attempt to control them.Those muscles sure get a lot of work when she's around.

"But, a couple of conditions," she said. "You were talking about rules to prevent things from getting out of control, and you were right. So, first rule: If I ask you to stop, you stop. I don't know if it's going to be painful and I don't know if it's even going towork."

"Of course," he said, kissing her. "I wouldn't have it any other way."

"I'm not going tosay 'Stop' unless it's one of those two things," she continued, "but I want your promise regardless."

"Of course," he said again.

"And second, you have to wear a condom."

"That sounds fair to me," he said.

"Okay," she said. "Okay. Then... Well... Let's try it."

So he got up and withdrew from her and they both went to the bathroom.

"What areyou doing?" she said.

Jon pulled out the tube of KY Jelly he had brought from home. "We're going to need this."

"Where'd you get that?"

"I brought it when we moved here. Idid masturbate until we got married, you know."

"We've been living here for over a month and I never found that?"

"Did you know what it was?"

"Okay, fair enough. Now, shoo."

"Why?"

"Well... I wanna go to the bathroom," she said. "I don't think there's very much... Back there..." She gave a covert tilt of her head to indicate. "But whateveris in there, I want itout so that you don't go bumping into it. The thought of you...interacting with that stuff... isn't a turn-on for me, Jon."

"Me neither." He wrinkled his nose.

"I mean, why do you think I'm making you use the condom?"

"Well, safety reasons," he said. "I mean, modern medicine being what it is, we don't have to worry about STDs, but if we did, anal sex would be one of the best ways to share it with the other."

Her eye twitched, but she nodded.

"Plus, it'll probably make it easier, because the latex will keep things smooth."

"You've been thinking about this too," she accused.

"Well, yes," he said. "Sweetie, we're not just talking about just... Sticking it in. There's a whole build-up that goes along with it. It's like making love."

She gave him a faint smile. "Well, you've always been good atthat, at least."

While she was occupied—after the toilet flushed, the shower went on for a short time—Jon flicked onto the Internet and did some work of his own. Caitlyn's faith in him notwithstanding, he still had his own concerns. He had tried to prepare for this, of course, but there was only so much preparation he could do before he began to cover the same material over and over. Besides, his main concern was something he would have to face in the moment: the anal sphincter. Simply put, Caitlyn needed to be relaxed about this whole thing. So far she seemed calm, but also deeply determined—and he knew force would not be the answer. In fact, determination seemed to him to be theopposite of what they needed. Instead of tension and force, she needed to be relaxed and completely accepting; after all, what she could accept in her mind, she would be able to accept in her butt.

How do you get a woman to loosen up if she's not entirely sure shewants to?

When she came out of the bathroom, he said, "I have another rule to put in place."

She gave him a skeptical look, but said, "Okay. What is it?"

"I get to call it off at any time too, if I don't think it's working."

She gave him the skeptical look again. "Jon, you put the condom on and then you slide it in. What doyou have to worry about?"

He touched her cheek. "You."

She said nothing.

"Caitlyn, you want to try this, and I love you for it. But just because wewant it to happen doesn't mean it'llwork. If you think things are getting out of hand, you get to call it off, no questions asked. If I think the same thing, I do too. The point is, I don't want you to force yourself to make this work. I don't want you to damage yourself for my sake."

She made a grimace that he couldn't interpret. "Okay." Then she took a deep breath and seemed to set herself. "So. ...How are we gonna do this?"

Setting the condoms and lube on the nightstand where they would be near to hand, he had her lie on her stomach. As he did, he recalled how often he had seen her like this, clothed, and how infrequently he'd seen her like this when she was naked. He almost rarely saw her body, even during sex; most of the time they were face-to-face, or at least spooned together. Now he could see it all: the elegance of her arms and the faint lines of her shoulder blades; the bumps of her spine; the ever-enticing curves of her ass and the treasure below them; the long strength of her legs; and as always the pale flawlessness of her skin. There was a little birthmark above her right buttock. How had he never gotten around to finding it yet?

This would be a seduction, paramount to the one he had managed on their wedding night, the first time they'd ever made love. Today, unlike then, she was much more relaxed and comfortable in sex; today, unlike then, he was attempting to involve an orifice that God had never intended to be penetrated. Even despite her new-found confidence in her own skin, he thought tonight would be the greater of the two challenges.

He began by sprinkling kisses around her face and neck before returning to her left ear, that familiar territory, site of so many explorations and discoveries. Gradually he began to move down her neck and spine, scattering kisses wherever and whenever the whim took him. Then, as before, he began to massage her back.

"Mmmm," she said. "Didn't I promise myself I was going to make you do this to me more often?"

He kissed her again in response.

"Hmm. I can feel your package. It's all dangly."

He was working at her shoulders, sitting astride her hips, his butt on top of hers, and his genitals had come to rest in the small of her back. "Sorry."

"No, it's okay. But, umm, it's all... Limpy."

He chuckled. "Believe me, hon, it won't stay that way."

He worked his way down, finally reaching the base of her spine, and then split his hands to follow the backs of her thighs. He could see from her pussy that she was a little aroused—maybe; not much, and possibly this was an artifact of their previous lovemaking. Nonetheless, she was relaxed and (if his own experiences were any guide) primed to be turned on.

He was right. It didn't take long before her pussy had darkened to a pale, feminine pink and shown signs of wetness. It was a little harder to get to her clit, since it was pressed down against the comforter, but she was instinctively raising her hips and in the end they worked it out. What wasalso hard was getting his fingers into her pussy with his face in the way; he ended up sliding his hand in sideways and curling his fingers, his knuckles pressed against his nose. He felt strangely like a snorkeler.

"Ooh, ooh..." she whimpered. "Don't let your cum leak out. Some of it's still in there."

He stopped. "Did you seriously walk around all day with my cum inside you?"

"Yeah. I totally—ohhh—I totally did. I could kinda feel it, even. It made me feel really sexy. All day." It madehim feel kind of sexy too; he could feel his cock stiffening even further. As if having his nose half an inch from the smell of her arousal wasn't doing enough.

Once she felt ready to him, he left her clit and began the real exploration.

Her perineum was not a very large area—her genitals being what they were—but he knew she'd probably never been touched there before, not even by her ownself. It was close enough to her asshole to be forbidden territory; it wasn't her pussy; and, he hoped, it wasn't associated enough with her butt that she would protest him using his mouth on it. He had a hunch that fingers wouldn't do it any good.

She shivered and whimpered when he first placed his tongue there, but nonetheless spoke up: "Jon, is that... Is that sanitary?"

"Didn't you wash after you were done?"

"Yes, but..."

"Then I'm sure it's clean."

"Clean enough for yourmouth?"

"It just tastes like soap to me," he said. "I think that's clean enough. Does it feel good?"

"Yeah, it feels fine..."

To judge by her reactions, it was better than just 'fine.' He knew that there was power in places that weren't normally touched during the course of everyday life; he intended to exploit this power as much as he could.

Her anus, of course, was another such zone.

He didn't just plunge in; instead he began walking up her buttocks with his fingers. Her ass was not a place he really paid that much attention to. Certainly it was very attractive to him, in its smooth roundness, but there wasn't a whole lot you coulddo with it; it was just there, with no special features. That was a downside, in his opinion. Nonetheless, it wasn't normal territory for him, and he intended to exploit that.

He traced his fingers over the crease between buttock and thigh, down the top of her crack, in criss-cross lines over the surface of her ass. There was hair here, as there was on him, but not enough to make much difference, besides, that puckered rosebud center was still in full evidence.

Finally, he placed his finger directly on it and began to move it in gentle circles. Caitlyn stiffened when he did so, but after a moment she began to relax.

"Sweetie," he said, "this isn't going to work if you're tense."

"I-I know."

"So... Just concentrate on the sensations. Concentrate on enjoying it. If it ever hurts, tell me. If it doesn't feelgood, tell me."

"Should it feel good?"

"Does it?"

A hesitation. Then, "...Yeah."

"In answer to your question," he said, "itshould feel good. Nobody talks about it, but there's pleasure nerves all throughout the anal sphincter. Doesn't it usually feel good to, you know, go number two?"

"Well... Yeah."

"So, don't worry, it's not like this is something your body wasn't designed to feel."

"Okay, okay. But... Do youhave to make me feel it?"

Jon looked up. She was propped up on her elbows, looking back over her shoulder at him. He suppressed a sigh.So it gets down to this. I did have the hunch.

"No, Caitlyn, we don't have to. There's nothing that says you and I 'have' to do anything. But, if it's okay with you, this is something I'd like you to explore."

"You'd likeme to explore?" she said.

"Well, yes. It's your body, isn't it? Shouldn't you be aware of everything it does?"

Her hooded eyes gave no indication of her reaction to this. "Well... Can you at least come up here for a while? It's all... It's kinda weird to have me up here and then you down there. Especially since I can't see anything."

Actually, that sounded fine to him. What they had done so far was rather clinical, to be honest, and he didn't want that to be associated with it in her mind. This needed to be something warm and emotional. If it was at all possible to make her ass seem romantic, he needed to do it.

Of course, that didn't stop her from freaking out again. "Jon! Don't touch me with that hand! It was just on my butt!"

Jon kept his face straight with an effort. "Caitlyn, did you clean up before we started?"

"Yes."

"Well, it looked like you did a good job. I didn't see anything clinging or dangling down there. I think everything on the surface is clean."

"But... But that's still..."

"I know it is. But that's exactly the point. It's not dirty, or dangerous. It just is."

She squeezed her eyes closed. "Still."

"Do you want me to go wash it?"

She gave him a cross look. "You don't have to take that tone with me."

"I'm not! I'm just asking..."

"Okay, okay. Yeah, why don't you wash it. I'll still be here." She sounded humorless.

While soaping his hand off, Jon reflected on the situation.This isn't turning out right. She isn't having fun, she doesn't like the idea.. Both of us are uncomfortable. Maybe we should give up, or at least try again later. No one says we have to succeed today. There's time. Hell, we'll be married for the rest of our lives. There's lots of time.

When he came out she was curled on her side, silent. He could see her pubis peeking out from between her legs, but there were more important things on her face—annoyance, confusion, sadness.