The Pregnancy Chronicles

The Midlife Crisis

I was living out my midlife crisis in a big way. I divorced in my late 30s, and while my ex-wife had done very well in the settlement, thankfully my big income gains have come in the last five years. I founded and currently run a hedge fund, one that's been very successful lately.

I worked hard, and after the divorce I didn't date, at least not seriously. It was easy to find women attracted to a wealthy, still young-ish, and fit man. Like, I was in every Eligible Bachelor magazine feature in New York. So sex came easy, but I began to get annoyed by the clear angling from women interested in being the next Mrs. Bradford.

So I turned to men. I hadn't fooled around with another guy since my college days, but it was fun to re-explore my latent bi side. New York had seemingly a million hot men eager for no-strings sex. Servicing my cock, or bending over for an anonymous quickie. It became like ordering take out for me, firing up an app after a long day, three or four times a week. No dates, no trying to impress, no bullshit excuse not to call the next day. Just getting my rocks off.

Officer Dinato was the first guy I met in person rather than online. He was a beat cop in the financial district and often popped in my building's lobby during his rounds to chat with the security guard. And, yeah, I noticed him immediately. 5'10" and really fucking built, not bodybuilder competition built, but packed with fit muscle that he clearly kept up in the gym and that filled out his polyester blue uniform very nicely. I estimated him in his mid-30s but he had dimpled cheeks and bright smile that made him look a little younger.

He seemed to notice me, too, always nodding at me in deferential acknowledgement as I walked out. And one night, as I made eye contact: "Have a good evening, sir."

Fuck, he got into my head. I started looking for online dudes with a similar look. Muscular, shorter 30-somethings. I bent them over my sofa and pretended they were a hot piece of NYPD beef I was plugging.

Officer Dinato seemed to be timing his appearance in my lobby more consistently, and I found myself leaving at 7PM each day, wanting to maximize the chance of seeing him.

"Evening, sir," he'd greet.

"Good evening, yourself, officer," I'd reply in return. "Stay safe out there."

"Yes, sir," he'd wink.

It was our little ritual, our routine. Maybe flirty, but on the surface it was innocent enough. Some guys are just gregarious and maybe Dinato liked being an Officer Friendly. And when you're an owner of a downtown financial company, well, you get used to a lot of deference from the city's police force.

Only one day I had to leave the office early to meet a colleague for dinner at 7. I was halfway down the block when I saw my favorite police officer walking my way, his muscled body looking incredible, a smile forming on his handsome face. "Cutting out early today, Boss?" he said.

I stopped a few feet from him. God, he looked even better up close. Brown eyes and dark brown hair, full facial hair shaved skin-close. Arms popping out the short sleeve hem of his uniform, big strong chest. "You bet, officer," I replied. "Got a dinner engagement."

"Hope it's a hot date, sir." Damn, he was flirting all right.

I smiled. "Fraid not, Officer...." I prompted for his name.

"Dinato. Brian Dinato at your service."

"Just a business dinner, Officer Dinato." I felt the compulsion to flirt myself. "I sure could use a hot date, though. In a big way." Then, feeling a rush of confidence, I added, "You think you'd be free some night, Officer?" I didn't even check if the cop had a wedding band on. Hell, at that point it might not have stopped me if he had. I'd been obsessing about Dinato for a couple of months.

The cop gave a friendly chuckle. "You asking me on a date, Boss?"

I had to chuckle at my balls in doing so. "Yeah, Yeah I am." I had no idea how the man would react. Probably not violently or impetuously, because he would have already freaked out by now. Besides, I was reacting to a clear vibe from him.

"That's what I thought," he replied. "I get Thursdays off, sometimes Sundays."

"This Thursday it is." I named my favorite downtown restaurant, one of those places that's nice but not so trendy that I ever had to worry about getting a table. "7:30."

"Looking forward to it, Boss."

***

Dinato showed up Thursday in an ironed dress shirt and khakis. Freshly shaven, hair slicked down with product, a bit of cologne filled my nostrils as we shook hands at the restaurant entrance. He scrubbed up well, but still looked every bit a cop in his build and the way he carried his body as he walked. It was hot.

I honestly didn't know what to expect. I'd never actually been on a date with a guy and it had even been a while since my last date with a woman. But Dinato put me at ease. It was like talking to a friendly guy I met in a bar... maybe we wouldn't normally be pals but at that moment we interacted as friends, as equals.

"This is a pretty nice place," he said as we finished our entrees. "Good choice, Boss."

"Glad you liked it. It's one of my regular places."

He looked like he wanted to change the subject from the restaurant and the food. "Can I tell you something, John?"

"Yeah," I said. He didn't have to ask.

He smiled and motioned for me to lean forward. He did, too, and whispered in a low growl into my ear. "My cop cunt's hungry for your big executive cock."

Holy fuck, that was the last thing I expected from Officer Dinato's lips but as he leaned back in his seat he had a knowing expression. He knew those words worked me up. "Yeah, you like that idea."

I gulped. I was hard in my trousers and my face felt hot with desire. "Fuck yeah, I do," I said in a low voice.

Brian smiled. "I'm good, Boss. You're gonna enjoy it."
I gave a smirk of my own and signaled to the server that I wanted the check.

We made our way back to my condo and once inside we were on each other, making out, groping each other, like sex starved teenagers. I don't know how often Dinato got laid, but I'd been fantasizing too long about nailing his cop ass and the prospect I might drove me wild.

We stripped as we giddily made out way back to the bedroom. Office Dinato's words at the restaurant were wild, but even wilder was the fact he was a skilled and hunrgy bottom. As soon as he plopped back on my bed, he pulled back those thick, knotted legs and showed off a shaved ass.

"Eat out my cop pussy and you can fuck it Boss."

I never felt harder. I got into position and rimmed that officer's hole like it was my last meal. I could feel his muscle body squirm the more I did it, until he finally tapped me on the shoulder.

"I need that cock of yours, Boss."

I nodded and lubed up. I didn't rush it at first, but Dinato's cop hole flowered up and soon I was sinking in. I couldn't help but kiss him deeply as I fucked him hard. I was surprised I didn't nut prematurely but as it was it didn't take long. Just feeling that police office beneath me, getting his own nut had me shooting.

Afterwards, it was all business. Officer Dinato getting up and going to the bathroom to clean up. When he returned he got dressed again and it was like we were just buddies once more.

"I guess that was a one-time thing," I sighed, still leaning back naked in my bed, in a state of sexual satisfaction.

He grinned at me with a cheeky smirk as he buttoned up his shirt. "Up to you. But like I say, I get Sundays off, too."

***

Brian and I had sex at least ten times over the next three weeks. Each time seemed hotter than the last, each orgasm deeper, more powerful. It wasn't a romantic connection exactly, but it was more than I'd experienced with anyone, man or woman, in a long while.

I loved Sundays, when we could fuck a couple times in an afternoon. But the chance to nail him in his uniform after shift ranks in my top 3 all time fucks, for sure.

Still, a nagging thought troubled me. Officer Dinato seemed too eager, too ready for me. Like it was all planned. And it wasn't my personality to avoid addressing it. Over a casual dinner one night, I had to speak my mind, consequences be damned.

"So, Brain... I've been around the block a bit," I started.

"I bet you have Boss," he smiled back, his soulful brown eyes almost melting my resolve.

I held firm. "And, well, maybe I'm wrong, but I get the feeling you're a gold digger."

I expected he'd be shocked or hurt or defensive. Instead he nodded. "I definitely am, Boss. I'm looking for a rich husband."

I was the one caught off guard. "What made you think I was an easy mark for that?"

Dinato seemed laid back about the whole conversation. "Oh I know you're not the committing type. I just had to take a chance. Ever since you made eyes at me on the street one day." I tried to rack my brain to recall that but couldn't remember such a moment. Brian read my confusion. "Oh you probably don't remember it, Boss, you were just being your normal horndog self," he chuckled.

The man had a way of breaking down my defenses. Still, I was suspicious by nature. "I'm not the first wealthy guy you've made a play for, am I?"

Again, Dinato seemed unfazed. "No, sir, but God's truth, you're by the far the best in the sack. Best hung, too." He popped a french fry in his mouth casually, like we were talking about the Yankees season prospects. It was a trip to see this muscular cop talking so boldly.

"You're something else," I said.

He looked at me and that was the first moment I recognized a vulnerability in his facial expression. "I figure you're a no-nonsense guy, so I'm not going to waste your time playing games. I'm a hot guy and a good fuck. You're rich and could use a guy to look after your needs on a regular basis."

I had to admit he had an appealing logic. Brian noticed I was pondering his words and grinned. "Yeah, you like the idea, Boss. You don't even have to say it."

"What would you get out of it?" I asked, playing out the hypothetical situation. "Early retirement?"

"Maybe, sure. And lots of hot sex," the policeman said. "Only that's not what I'm angling for."

"What are you angling for?"

"I want lots of kids. See, there's this operation that lets men have babies. I want to get it, but it's not cheap."

This was the last thing I expected from this built, butch man. "And you're looking for someone to pay for it."

He nodded. "Not only that. I want a man who can support our kids well. Good education, private schools, sports lessons, all that business."

"What makes you think I want kids?"

He shrugged his shoulders "Maybe you don't, but I've never met a Wall Street exec who doesn't like the idea of his name and lineage continuing."

He could see I wasn't super keen on the idea, so he got a conciliatory expression and added, "Just think about it, Boss. You know I'm a good lay. You just gotta decide whether you want me on a long-term basis." He chuckled a little. "You know, this is probably your last chance to bag a New York City police officer."

He had me there. Still I was guarded. We didn't have sex that night, and it was as if Brian expected me to bid him good night after dinner. I didn't get a text from him the next day, nor the following. I was too stubborn to do the pursuing now, and I didn't want Dinato to get the sense he was going to get a commitment from me. Christ, we'd just been fucking for three weeks.

I went through withdrawals, though. I stroked off thinking about Brian Dinato's round ass, his cute face, his police uniform. And that muscle bod. I came buckets each time.

The kicker was running into him in the building lobby. He was there, chatting with the security guard, just like always. He gave me a flirty look. "Evening Mr. Bradford."

"Evening Officer," I said.

I was horny after that encounter and emotionally worked up. What the hell, there were plenty more fish in the sea. I fired up my app and lined up a hot 30-something guy who lived in Midtown who could host. I fucked the dude wildly, fingers gripping the guy's strong waist like eagle talons, dick pounding rapidly in and out of his guts, feeding off my frustration with Brian, until I finally shot my load deep in the ass of a substitute who never could take the place of Officer Dinato.

I repeated that the next night, finding an anonymous fuck to get my rocks off. The guy, a 20-something analyst who worked on the Street, blew me well and left me physically satisfied but emotionally no better off. I tried to be strong but about 10PM that night, I couldn't take any more. I got my phone and sent Dinato a text. "I miss you, man."

"I miss you too, Boss," was the reply.

I called him, wanting to hear his voice.

"Hey Paul," he greeted, using my first name for the very first time.

"Hey Brian," I said. "You know... you have a way of getting into my head."

"You've gotten into my head, too, Boss," he admitted. "I almost caved and called you first."

This captured me and Donato's dynamic. Playing power games but being very open about it. "What made you stop?"

"I want to get pregnant," he said. I still couldn't match the Staten Island accent and butch voice with those words. "I need to get pregnant Boss."

"I'll do it," I said. "I'll pay for your operation."

"You won't regret it, Boss," he said, a thrill evident in his voice.

Dinato was right: I haven't for one minute regretted it.