The First Ninety Days Ch. 13

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On Valentines' Day, Caitlyn agrees to try anal.
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Part 13 of the 16 part series

Updated 10/08/2022
Created 08/10/2008
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CWatson
CWatson
96 Followers

Day 67

Jon woke up first on Thursday, which meant he could be the one to say "Happy Valentine's Day" first.

"Aww, I wanted to say it first," Caitlyn said, leaning in for a kiss.

"I could fall asleep again," Jon said.

"No, we don't have time," Caitlyn said. They had gotten into the habit (when they weren't abstaining due to arguments) of waking up quite a bit earlier than the alarm, in order to fool around if they wanted. Sometimes they didn't; sometimes, especially of late, they preferred to just lie together and talk. These times were not only some of their best sex, but some of their best love and communication as well—not to mention, sometimes, theironly chances to get in touch with each other all day, especially on Tuesdays and Thursdays when their schedules kept them apart from 9 to 8. When they were fighting, Jon had missed these moments more than he could say, and he was more glad than he could say that they had fallen into this particular habit; it was the best way he could think of to start the day: focused on what mattered to them. Focused on each other.

"Butnext year," she threatened, "you'd better sleep in so I can wake up first."

"Next year?" Jon said. "I didn't realize we were planning that far ahead."

"Well, now you do," she said with a smile. It was a gentle reminder, he knew, that she wasn't going anywhere. She leaned in to kiss him again. "And since I haven't said it yet: Happy Valentine's Day."

For a moment, they just cuddled together, skin on skin, breath on breath.

"Man. I can't believe we can do this," he said. "Before we got married, if we'd been like this, I would've been all like, you know, 'Sex! Let's have it!' But now we can just... Be."

"Yeah."

"I've been looking forward to this for a long time."

"Huh?" She peered up at him. "Not having sex?"

"Yeah." He smiled. "Well, not, I mean, not-having-sex, but... Being in a place and a position where... It's okay not to. Where we know we don't have to be, you know, all over each other, because there will be time. When there's no pressure and we can just... Be."

"Where we can take each other for granted."

"Yeah. This iswhy I was pushing for us to, you know, start getting intimate sooner. So that we could arrive here."

She gave him a sardonic look. "Sweetie, if you're gonna tell me you wanted us to start having sex early so that we couldstop having sex early... I'm not gonna believe you."

"Well, umm... Humph," said Jon, to admit defeat, and they snuggled silently for a few more minutes.

"So," she said finally. "What would you like to do on this lovely first Valentine's Day together?"

"Stay home and make sweet love to you all day long," Jon said.

"And what are yougonna do?"

"Get up, go to work, and make money," Jon said. "And then sit around for an hour and a half until you get home and I can spring my surprise on you."

"Is it a reservation somewhere?" she asked.

"That would be telling," he said, giving her a smile. He wasn't going to let this one out until they got there.

"Can it be changed?"

"Why?"

"Because I talked to Dr. Murray, the orchestra conductor. He says that they aren't doing any of the music that requires a harp today, and I don't have to show up if I want."

Jon blinked. That did indeed throw all his plans out the window. "Umm... It's Valentine's Day. People book these things like six months in advance. I don't know if we can change it."

She gave him a leer. "Well, this is whathappens when you keep secrets from yourwife."

"How am I supposed to make it a surprise if I don't keep it a secret," Jon protested, sticking his tongue out at her.

"Well, umm... Humph," said Caitlyn, to admit defeat. "Just like a man, of course. Makes all these plans, and then doesn't account for new developments. Can't be bothered to..."

Jon rolled his eyes and dove in to kiss her.

They quickly grew amorous, and before he knew it he was suckling at her breasts, feeling her pliant flesh against his face, drawing her nipples into stiff tension. She drew his head in closer, pressing him to her, and somehow they ended up rolled over, with her above him, cradled in the curve of his body, moaning and gasping and pressing herself to him. He didn't have to reach below to check her rising ardor; he could feel the heat, and now the wetness, against the skin of his stomach.

Unexpectedly she backed away from him, maneuvering, reaching for his hand with hers. Then she was straddling him, guiding him in, sinking clear to the bottom in one smooth thrust. She wriggled her other hand and he seized it in hers. Then, supported thusly, she began to ride him.

The penetration was deeper and of a different quality than he was used to, as she guided him towards spots inside herself he hadn't known existed. It was also completely different to be seeing everything; normally he either got the arch and bump of her back, or her face beside his, but now he could see it all: her nipples, taut and still shiny with damp; her breasts proud and erect as she rode him; the smooth flat expanse of her belly and the adorable dimple of her belly button; and even her pussy lips clasping his shaft, pressing against him with every downstroke. He stared at that greedily for a moment before leaning up to attack her breasts again.

Between urine pressure and the incredible stimulation, he wasn't going to last long and he knew it. He asked her to stop, or at least slow down, until he could get some control over herself and last longer.

She gave him a wicked grin. "Who says I want you to last longer?" She ceased her thrusting, but began to move her hips back and forth against his, his cock still trapped inside her and caressed on all sides by her warm, clinging pussy. Jon moaned into the hollow of her neck. "It's Valentine's Day, my dear, and I want to start it off right: with your cum inside me."

The fleeting thought crossed Jon's mind that he might have bitten off more than he could chew; then he was cumming, ecstasy pounding through him as he exploded inside her, held rigid by the sensation as she continued to move on him, sending paroxysms of pleasure through him as he groaned and clenched and spurted up deep inside her, harder and longer (it seemed) than he had ever come before. His whole body felt tight, especially below, as though she had begun to suck him into herself; his heart was hammering within his chest.

He collapsed back against the headboard, spent. After a moment, he felt her lips feathering against his neck.

"Happy Valentine's Day, my love."

"Unhg..." he said. It was about as much coherence as he could manage.

He heard her pleased giggle. "This time, I don't care who notices: this one's staying inside me."

"Unh... Aren't you... Going to school?"

"Yeah, but it's only one class and my lesson. After that, we're going out to dinner."

"Wheremore people see you."

"So, maybe I'll take a shower before then." He heard her grin.

He tried to open his eyes; he didn't really succeed. "You'remuch too chipper for this early in the morning."

She kissed him. "What's not to be happy about? It's Valentine's Day, I'm with the man I love, I have a load of his cum deep inside me where hopefully it'llstay when we're done—and, from the looks of things, I just did such a good job with you that I blew a couple of fuses. I'd call that a good start to the day."

"Well, I'm gladyou're happy.I have to drive a car." This time his eyes opened. "MaybeI should take a shower."

"Wouldn'tthat be a reversal," she said, teasing. She lifted herself off him, and he almost whimpered at the sensation rippling through his still-too-sensitive cock. "Well, there's nothing else to be accomplished here. Up and at 'em, sweetie. We got a long day ahead."

In the shower, Jon woke up fully. He shook out his head and chuckled to himself.I might indeed have bitten off more than I can chew... But at the very least, the ride will be fun. The funny thing is, though, that there's only certain things she's really enthusiastic about. She likes the idea of being dominated, and she likes it when I cum inside her, but mention almost anything else... He shook his head again.Well, that's the way it works sometimes. Besides, both of those ideas are relatively conservative—almost Biblical, in their own way. And the part where she likes me cumming isn't a bad benefit.

When he came out of the shower, Caitlyn was dressed and preparing for her day. "Just so you know," she said, "You're not the only one with surprises."

"Umm..." he said.

"What?" she said.

"Well... Considering you almost killed me just now and we haven't been up an hour yet, I'm kind of..."

"Well, that was one of the surprises, so now you know what's in store," she said, smiling.

Jon was devoutly glad he had stacked a couple more surprises of his own throughout the day. Meanwhile, though... "So you mean I'll be fucked within an inch of my lifemore than once today?"

"Nooo," she said, giving him a patient smile. "Not all of them involve sex.""But some of them do?"

Her enigmatic smile was all the answer he got.

"Man," he said. "I'm not sure whether to jump with glee or run for the hills."

"And here I thought you were the one with the sex drive," she said, grinning.

"Ido have a sex drive. It's just that it's pretty general. You only like a couple of things, but you'rereally into them. It's about the same energy as mine, but, really concentrated."

"Hmm. Fair enough," she said, smiling. "But, in the meanwhile, go on ahead and go to work. You have surprises to look forward to."

"I'd also better fill out a life insurance policy," he said. "Just in case."

She gave him a dirty look, and then snagged him as he was going out the door for a long, lingering kiss. Suddenly she was clinging to him, tears in her eyes.

"I love you so much, Jon," she whispered. "I never thought... I never thought I could be playful like this. I never thought I'd beable to be... This."

He gave her a wry smile. "Crazy and horny?"

She blinked up at him with her beautiful dark eyes. "Happy."

He kissed her back. "I love you too, Caitlyn. Making you happy is what I was put on this earth to do."

"Happy Valentine's Day."

"Happy Valentine's Day."

The first surprise was a Singing Valentine. Jon was in the back along with Nathalie Watts, Jason Belton, Hector Gonzales and Celise Chan—the other trainees, in other words—being lectured on the intricacies of the blood-pressure cuff, when someone cleared his throat from the doorway, and everyone turned to see a man of immense stateliness and immense bulk. "Excuse me," said the man in a resonant voice. "Is this Room 204?"

"It is," said Thuy, the teacher.

"My name is Roger Valentino," the very large man said. His every movement and word carried the gravitas of a Shakespearean actor. "I am looking for Mr. Jonathan Stanford. Is he within the confines of this room?"

Everyone looked at Jon. Jon felt a bead of sweat drip down his face.

"Ahh, I see I have found the right place." The man entered the room. He was of such ponderous girth that Jon had no idea how he would fit through the threshold, yet he seemed to negotiate it as though it were nothing. "I have here a Singing Valentine to be delivered to a Mr. Jonathan Stanford from a Miss Cai— Ah, I beg your pardon, from aMrs. Caitlyn Stanford. Your bride, I presume?"

Nathalie giggled. Jon had to clear his throat before speaking. "Uhh, yes, that would be—" He had the insane urge to say, 'No, that's my mother.' "That would be she."

"Well, then, Mr. Stanford, I beg you attend these words which I shall now sing. And, your beloved urges me to assure you, they are meant from the heart."

Thus he planted his legs solidly, drew a dramatic breath, and began to sing in his rich, resonant voice.

Baby, I'm so into youYou got that something: what can I do?Baby, you spin me aroundThe earth is moving, but I can't feel the ground

People were beginning to laugh, which (Jon had a hunch) was the whole point. Mr. Valentino's voice rang through the room; Jon could see, from the room across the hall, heads popping out, and thought people might be hearing it all the way to the front desk. Even better, Mr. Valentino was overplaying the part: dramatic gestures and facial expressions, and the most exaggerated vibrato Jon had ever heard; he sounded a little bit like an ambulance siren. Jon was beginning to smile himself.

Every time you look at me,My heart is jumping, it's easy to see:You drive me crazy!I just can't sleepI'm so excited, I'm in too deepWhoa-a-a, cra-zy,But it feels all right!Baby, thinking of you keeps me up all night!

At this, Mr. Valentino flourished his cape and gave a deep bow, as though he hadn't just finished an operatic rendition of a Britney Spears song, and everyone applauded, Jon included.Man, how am I gonna topthat! Everything I set up seems so lame in comparison. Though at least the musical Valentine he'd set up involved some flowers.

During his break, he called the restaurant to alter the reservation. Clearly, the gods were smiling on him: the person who had called before him had done so to cancel their 6:30 appointment, which the Stanfords would be able to make if they hurried. So, with a minute left in his break, he called Caitlyn. "Hey baby."

"'N Sync?"

"Yeah."

"You know I hate them." She was grinning.

"Oh yeah? Well,you know I hate Britney Spears."

"It was revenge. I knew you were gonna send someone to sing 'N Sync to me."

He laughed. "Well, the good news is, we're on for dinner at 6:30."

"You got the reservation moved?"

"Yup. Be ready to jump out the door the instant I get home."

"Aww, too bad. I had some ideas about how to spend the the time until our 8:00 reservation."

"Oh?" he said.

"Yeah. But there's no time now. And besides, you said I had to be dressed."

He felt his eyebrows jump. "And was that going to be one of your surprises?"

"Well, I think it would've been surprising, but no, I hadn't planned it; it just occurred to me."

Unfortunately, he didn't think the restaurant would be pleased if he switched back to the 8-PM timeslot. "Well, we'll just put that into playafter we get home."

"Any specifics on clothing?"

"It's a pretty nice place, if that's what you're asking."

"Oooh, splendor and finery." He heard her grin. "Now Iknow it's Valentine's Day."

"I love you."

"I love you. Happy Valentine's Day."

Fortunately, there were no more Caitlyn-sponsored surprises throughout the work day, though Jon did get a little good-natured ribbing from the other staff members. Okay, maybe alot of ribbing. People were still asking about the 'opera singer' when he was leaving to go home. The worst, of course, came from his classmates.

"Wow, someone must really love you," Celise said. She had an accent, if not much of one, but the straight black hair and yellowish skin were a dead giveaway. "Either that, or have a lot of money to blow on you."

"How'd you get someone to like you that much," Jason asked him. "You secretly a hypnotist or something?"

"Hell, how'd you getmarried," Nathalie said, grinning. "You're, like... What, twenty-two?"

"Twenty-four," Jon said.

"Shit, man, I'm twenty-eight," said Jason.

"He must've taken her to Vegas and got her drunk," Hector laughed.

"Or got her pregnant and had to marry her," Nathalie said.

"Or maybe it was an arranged marriage?" Celise said.

Jon decided to laugh about it. "You all are just jealous."

"Pfft. Of getting tied down?" Jason laughed. "Hell no, man; freedom's where it's at."

"Yeah, but, he gets it regularly," Celise said, nodding in Jon's direction. "Doesn't have to go out to a bar and get a girl all liquored up."

"Ha," Jason said, his teeth startlingly white in his dark face. "LikeI got to get a girl drunk to get her interested inmy johnson." He was grinning.

"Oh, you don't?" Nathalie said, laughing. "No wonder you don't get any."

"Hey now, don't be giving a brother a hard time," Jason said, with a transparent attempt at wounded dignity.

"So what actuallydid happen, Jon," Celise asked. "Now that we've impugned your reputation and that of everyone at this table. You're notthat old. How'd you get hitched so quickly?"

Jon gave them the condensed version of it; their breaks weren't all that long, after all. For the most part, his coworkers seemed impressed.

"But don't tell me you're gonna take that shit lying down," Hector said. "She sent some guy in to sing bad music at you? You so pussy-whipped that you just gonna take it?"

Jon grinned. "I did the same to her."

"Britney Spears?"

"Worse. 'N Sync."

"Holy shit, man!" Hector exclaimed. "If you're divorced by tomorrow morning, we'll know why."

"I think the only thing colder would be to send someone to sing Eminem," Nathalie said.

"Excuse me!" said Celise.

"Or Whitney Houston, that song fromThe Bodyguard or whatever," said Jason. He pitched a screechy falsetto: "And I-iiiiiieeiiiiii..."

"Excuse me!" said Hector.

"You're in the wrong key," Jon said, deadpan. And that was how break went: with laughter and bad music all around.

Caitlyn, as he'd requested, was waiting and ready to go when he arrived home. "Where were you? That took a little longer than normal."

"Traffic," Jon said, grimacing. "At least we'll get the carpool lane together."

"What do you think," Caitlyn asked, spreading her arms. Her hair was up in a complicated knot, and she had dressed stylishly and well, in a night-black gown that somehow stayed demure despite the way it hugged her figure. The blue highlights brought out her eyes; the little fringe on her shawl swung as she moved. Jon, who had planned on a polo shirt and some khaki slacks, made a note to dress up a little more.

"I think that you must've gotten home and spent the entire time deciding what to wear," Jon said, grinning.

"No, I also decided whatyou should wear too," Caitlyn said, grinning. She gestured to the bed, where (indeed) a dress shirt, tie and pressed slacks were waiting for him. "We'll match."

"Cool," said Jon, smiling. "Do you know how to do a tie?"

"Yeah," she said, her smile vanishing, "don't you?"

"I barely ever wear one," he said.

"It's amen's accessory."

"Istill barely ever wear one," he said.

She rolled her eyes and brushed past him into the room. She had it ready by the time he had the other clothes on. "I'm gonna have to teach you this. How are you going to tieme up if you can't even tie yourself?"

Jon blinked. "I'm tying you up?"

Caitlyn beamed at him. "I sure hope so."

Jon shook his head and smiled. "Let's at least have dinner first."

"Mmm, dinner," she said. "You said it's a surprise. Where are we going?"

"Didn't I say it's a surprise?"

"Yes."

"Well, it's a surprise." He stuck his tongue out at her.

"Don't point that at me unless you intend to use it," she said.

He gave her a leer. "Who says I don't?"

She stepped close, entwining herself into his arms, and kissed him. "Happy Valentine's Day."

"Happy Valentine's Day. You know, you do realize that saying it over and over doesn't make it true."

"So? Whatelse am I supposed to say? Okay, then:Saaaaad Valentine's Day." She made a puppy-dog pout.

"Besides. With you here, I don't need anything else to make it a good day."

CWatson
CWatson
96 Followers