M/F ~ Office Sex ~ Age Gap ~ Boss/Employee ~ Forbidden Sex

I Showed My Secretary that I’m the Boss of Her

It was time to show her that I was in control and she had to work hard for me, whenever and however I wanted her to.

My two friends and business partners and I had been fucking our secretary and it seemed that the three of us — Clay, Seth and me, Jack — were all falling for her, too.

We had had a drinking contest and decided that the winner should be the one to ask Carrie which one of the three of us she wanted to be with for good. I had won, and now I was impatient to ask her.

I’d always been a man who went after what I wanted and it was killing me to not know whether Carrie and I could be together for good, or if she would choose one of them. Or maybe it was just killing me to not have her with me.

I knew I shouldn’t want her like this — she was half my age, and my employee. Plus, I wasn’t usually the kind of man to pine after any woman.

In fact, I was usually one to leave them pining for me after one night together, and then I’d make it a point to never see them again.

But Carrie had me acting the complete opposite way!

So, later that evening after the drinking game that I’d won and which had sealed my fate as the one to ask Carrie for her decision, I called her up and asked her if she could come over to my house.

Luckily, she agreed.

It had started raining again and now the rain was starting to turn into sleet in the cold winter weather.

I sent a private car for her just to make sure that she would be safe getting to my house.

When she showed up, she was drenched.

“You wanted to see me, Boss?” she asked, and there was something flirty in her voice that I really liked.

“Yes, I sure did,” I told her, and suddenly I knew I wasn’t going to be asking her which one of us she wanted to be with — not today.

I wanted to get in those panties of hers and finish what we’d started yesterday at the ice-skating rink.

“I have an indoor pool inside my house. Since you’re already soaked, do you want to go swimming?” I asked, knowing that the suggestion probably sounded like it was coming out of nowhere, and it was.

I hadn’t been planning to do that with her but now that she was here, I just wanted an excuse to get her out of those clothes so I could see her hot naked curves!

“For real?” she asked me.

Her face lit up like a Christmas tree and it was the prettiest thing I’d ever seen.

I nodded, and she immediately grabbed me by the arm. We went to my pool, which had skylights allowing us to see up to the night sky, which was pitch black by now since it was officially winter and studded with stars.

I set up Drake’s latest album to play before diving into pool, naked. From there I watched Carrie remove her own clothes and admired her gorgeous, naked curves like I’d been dying to do. I smiled happily to myself, glad I was the one who had won the drinking contest.

The guys couldn’t be mad at me for being with Carrie when they had said I was supposed to ask her the question!

I loved having her all to myself even for just one evening. And I was hoping she would choose me so that we would have many more evenings like this together. A whole lifetime of them — if I had my way!

Under the sleet that fell onto the skylight and with the sound of the calming music surrounding us, the ambiance was second to none. When I looked back over towards Carrie, I was speechless as I saw her walking in my direction. It was as if the world had turned into slow-mo.

She looked effortlessly attractive. The way she walked with her hair fluttering had me sure I was falling in love with her.

Suddenly I realized the reason that I didn’t want to ask her which one of us she might want to be with was because I was afraid the answer wouldn’t be me, and I didn’t want our time together to ever end!

Her body was a work of art — an easy 10 out of 10!

And I wanted to keep it all to myself, forever.

She had no idea just how beautiful she was, just as she was oblivious to the effect that she always had on both my body and my heart.

“Hey, are you okay?” she asked me suddenly.

I had been so lost in my thoughts of our future together that I hadn’t noticed that she was standing right on the edge of the pool where my arms rested. I looked up and was welcomed by a closer view of her curvy, hourglass shaped body.

She leaned forward with her hands on her knees. Now I got a clearer view of her ample bosom.

Was she doing this on purpose? I wondered.

And then I decided that she probably was. My baby knew just what I liked.

“Are you sure you only invited me over for a swim?” she asked flirtatiously.

I responded by grabbing her arm and pulling her into the water with me. I thought I had reached my quota for teasing her so much. But I couldn’t help it — it was incredibly satisfying to see the effect it had on her. I liked knowing that I got her riled up just as much as she got me riled up.

“Hey!” she protested, her cheeks blushing a sexy shade of red.

“Okay, I’ll stop,” I promised her. “Here, have a drink.”

I reached up and handed her the glass I’d mixed for her before getting into the pool. Meanwhile, above us fog replaced the drizzle, and the mood became more intimate.

“Can I ask you something?” she asked me all of a sudden.

“Sure.”

“I’m just wondering, what’s up with you… and Seth lately?”

Hearing Seth’s name while we were together somehow pushed my buttons.

I hated how they had spent time alone together and that he had had her all to himself.

This would have been the perfect opening for me to tell her we all wanted to be with her for real, and to ask her which one of us she might want to be with, but I didn’t want to spoil the mood.

“Let’s not talk about Seth right now,” I told her. “Or Clay, either.”

“Okay,” she said skeptically, raising her eyebrows at me. “Whatever you want. You’re the boss, after all.”

“Yes, I am. The boss of you,” I joked, and she smiled as if she liked that I was.

I grabbed a bottle of wine I’d set down next to the ledge of the pool and gulped a bunch of it down in a series of successive swigs. Then I set it back down and pulled her body against mine and kissed her aggressively.

It didn’t take long until she matched my forceful approach of owning her soft lips. I put my hands on her hips while her arms were around my neck and kept kissing her.

With my back leaning against the edge of the pool, she clung to my shoulders and wrapped her legs around my pelvis. I felt her pussy touch my already-very-hard cock. Our tongues swirled as she rubbed her body against mine.

She was trying to take control, and I was the boss, so I held her ass with both hands and dictated the speed of grinding her mound up against my now-rock-hard cock. As I did so, water splashed on our bodies, matching the rhythm of how I was pushing and pulling her body.

I felt her quiver as she released loud moans from climaxing just from our dry humping. Or I guess I should say wet humping!

“I bet you thought I was the one who wouldn’t last a couple minutes,” I teased her. “Since I’m the guy, after all.”

“No. I know you have a lot of stamina and always make me cum a lot. Mind you, I’m just starting,” she said and broke out of my grasp.

Then she waded to the shallow area of the pool. She twirled around, teasing me with the sight of her gorgeous body.

I loved everything she did and said. I wondered what sort of holiday miracle had sent her my way. Because I just couldn’t believe how perfect she was for me.

I followed her, saying, “Okay, apparently you are in charge now.”

While looking at the moon up above us, Carrie held onto the edge of the pool for support while I lifted her legs up and she started straddling my hip. It felt so good to put my cock into her tight, wet pussy. Bending my knees a little, I started thrusting in and out of her.

The sound of the water splashing along with her wetness filled my senses. With our position, I could hear her whimper as her grip tightened on the edge’s surface. I stopped for a bit only to change holes and claim her ass this time.

Under the water which acted as a natural lubricant, I easily slid my manhood inside it. The splatter of water around my balls got me feeling a different kind of sensation. I hadn’t thought I would be fond of having sex in the pool, but now I was. I guess anywhere and everywhere were my favorite places to have sex with Carrie!

Being one on one with her was a fun feeling but I also liked watching her get stuffed by multiple cocks at once. And yet I couldn’t help being jealous of the other two guys whenever that happened.

It was a real conundrum and for now I was glad it was just her and me although I kind of wished that after I got done having fun with her, Seth and Clay could join in, and we could start all over again.

For now, though, I pounded Carrie’s tight little ass hole harder and deeper, as if to remind her that I was way better than the other two. Especially Seth!

“Oh, Boss, that feels so good,” she moaned.

“You love having your little ass hole filled up by your boss’s big cock, don’t you?” I asked her.

“Yes. Stuff me full, Boss.”

“I’m crammed so far inside your ass that I never want to come out,” I told her, as I kept going.

Despite my own feelings on the matter, Carrie seemed a little exhausted from the previous position, so I did pull out of her ass, in order to yank a pool floater closer to us.

She lay down on her stomach on top of the floater. Then I positioned myself and claimed her pussy that was already pulsating from pleasure. I was pulling in and pushing out as fast as the music’s beat.

“Yes, that’s it! Faster, Jack! Faster!” she begged me. “Oh, Boss, it feels so good when you fuck my pussy. I want more of it. Harder, faster, longer! Please, Boss.”

I obliged and pumped harder into her wet cavern until I howled like a wolf from the extreme sensation which sent my whole body wriggling. She and I came at the same time, her pussy getting even wetter and slipperier, as my dick slid all around inside it.

“Fuck yeah, your boss is cumming into your hot little pussy, without even wearing a condom,” I told her.

“Crap. What if I get pregnant?” she asked.

I shrugged and said, “That wouldn’t be the worst thing.”

In fact, if I knocked her up, she could never leave me if she were to choose Seth or Clay instead.

I began to like the idea more and more.

As I pulled my dick out of her pussy, my thick fluids mixed with her cream and the whole mess floated up to the water’s surface.

“Look, my creampie is swimming too,” I told her, and we both laughed.

We got out and lay on the lounger for a while with Carrie’s head resting on my chest. Both of us were looking up at the bright stars in the skylight above us and I was wishing that tonight would never end.

I loved how dirty and fun but also sweet and submissive she could be.

She was definitely my perfect woman and I hoped that Christmas would bring me the gift of her choosing me forever.

Because I wasn’t sure what I would do without her now!

The End… For Now.

Thank you for reading! This is part of my erotic serial on Medium. Click here to continue on to the next part in the Serial.

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