M/F ~ Cuckold ~ Older Man Younger Woman ~ Age Gap ~ Boss Employee

I Fucked My Secretary… and Then My Business Partners Wanted to, too.

I couldn’t help but want to date her and fuck her. Even though I knew it meant hell to pay from them.

Once I’d arrived home from work yesterday, I’d messaged my secretary Sabrina that she could take a paid day off today. You’d think that she’d be pleasantly surprised since that doesn’t usually happen, but instead she seemed mad and suspicious.

She’d been so jealous lately — ever since the office Christmas party when Seth, Jack and I had hooked up with our curvy new employee Carrie, and even more so since we’d been doing it again. And again, and again.

She knew my reputation as a player and my proclivities for sharing a woman with my friends and business partners, so I didn’t know why she was taking this time so personally… other than the fact that I was way more into Carrie than I’d been into any of the other girls I’d ever hooked up with.

She must have known I was in deep for this voluptuous goddess and so it bothered her more than the meaningless foursomes I’d had in the past.

But I didn’t have time to think about Sabrina lately because my mind was on my upcoming date with Carrie. I’d have to figure out a way to deal with my jealous secretary some other time when I wasn’t caught up in the excitement of getting to see Carrie all on my own, without the other two guys there to get in our way.

This feeling was something certainly new and different for me and I had barely even been able to sleep last night due to the anticipation.

Now here I was, standing outside Carrie’s apartment. I was an hour earlier than the meeting time we had agreed on, but it couldn’t be helped. Since I’d hardly been able to sleep a wink last night, I wanted to hurry up and get the show on the road.

Carrie had left the door to her house unlocked so I entered, thinking she must have meant for me to walk in since she knew we had a date planned. When I got inside, I heard the sounds of water running from the bathroom.

I tried to wait patiently, looking around at the pretty Christmas decorations that Carrie had up on display, but all I wanted to do was jump her bones!

I wouldn’t mind joining her gorgeous, naked curves in the shower, I thought, and so I wandered into her bathroom.

“Carrie?” I called out.

She jumped and nearly screamed out in fear.

“Sorry, it’s just me,” I told her.

“Mr. Vasquez, maybe you should knock next time,” she said harshly.

She was right.

What was I even thinking this early in the morning?

I was about to apologize but she added, “Then again, I did leave the door open for you. So, you might as well join me in here.”

“Great minds think alike,” I said, and hurried to take off my clothes.

I was glad she’d just been kidding. I didn’t want anything to get in the way of the fun we always had together!

When I stepped into the shower, I couldn’t take my eyes off Carrie’s naked curves.

“You have the most Jacktiful body I’ve ever seen,” I told her, looking it up and down. “I just can’t get enough of you.”

I grabbed her waist and pulled her body against mine. Our eyes locked and shortly, our lips did, too.

I immediately went for some tongue action, and she reciprocated the gesture. The warm temperature of the water added to the extreme tension that had already been heating up inside my body.

I knew I was risking my entire company being here, since my partners had already said they would try to oust me if I broke our deal about only sharing Carrie together and instead tried to be with her alone.

And yet as our tongues entwined and our wet bodies pushed up against each other, I felt that it would be worth it.

I would be willing to lose the whole world as long as I could gain Carrie.

Carrie leaned back against the shower wall, and I kissed her nape down to her shoulders and then started licking and sucking on her nipples.

“Oh, that feels so good,” she moaned, and I turned her around so I could get a view of her plump, luscious ass.

I was reminded of the first time I’d caressed it as I got a good view of it while she wiggled it around in front of me. I squeezed and slapped it hard while the hot water poured down on it.

I heard her grunt, and I liked the sound of that. I knew she was good and ready for me now, just like I always was for her. I positioned my hard cock at her entrance and gently poked it into her tight little hole for some teasing.

Seeming like she had had enough, Carrie reached around and grabbed my cock and pushed it further into her warm, wet pussy.

“I got your message,” I said with a chuckle as I finally thrust my dick all the way into her.

I was doing it slowly at first, but the feeling of her tight pussy walls wrapped around my cock got me excited.

I rammed my tool as fast as I could, which made the sounds of her moaning intensify.

Then I used my right hand to cover up her mouth while my left one fondled her big, soft breasts. Peeking out of the shower curtain, I could see our reflection in the mirror, and I loved how hot Carrie looked with her wet hair hanging down into her face while I was banging her.

She licked my fingers, and her expression turned me on so fucking much.

It was a different kind of stimulation than anything I’d felt before!

I could feel the wholeness of my cock fill every space of her pussy. Shortly, I pulled out and spat on my throbbing penis and claimed her asshole.

“You’re so tight,” I said, as I spread open her tiny hole with my huge dick. “And you love when I put my cock in your ass, don’t you?”

“Yes, Sir,” she said, sighing happily. “I love when my boss puts his cock into any of my holes. You feel so good in my pussy and my ass and my mouth.”

Our dirty talk was turning me on even more. I leaned forward and licked her ears before I bit them.

As I pumped harder and deeper each second, I heard her groan in pleasure. I remembered seeing her touch herself as the voyeuristic side of me awakened from watching her drown in pleasure.

The thought of her playing with her pussy while thinking about me and my two best friends fucking her pussy, ass and mouth made my hard cock start to throb.

She obviously enjoyed the sensation because she started cumming, causing me to grab hold of her breasts and play with her nipples while she did so.

“Oh, yes, Boss, this feels amazing!” she cooed, as her hot body shook with the power of an orgasm.

To my surprise, I didn’t last long before shooting my load into her ass. I could usually go for quite a while, when my friends were joining in, but there was something about being with her one on one that made me explode with pleasure.

My toes curled up and I leaned against the same wall of the shower that she was leaning up against as well. I wanted to howl like some kind of animal due to the extreme pleasure I was feeling.

That was fucking amazing!

But Carrie brought my thoughts back down to reality when she said, “I guess we should get washed up and go on this date you wanted to take me on, right?”

“Right,” I said, nearly forgetting why I was here.

It didn’t matter to me what we did, as long as we were together. But I wanted to show her a good time and convince her that I planned to be with her for real, whereas my other two friends were just in it for the thrill of the sex.

I had never fallen in love before and I didn’t think I ever would, but here it had hit me like a thunderbolt and there was no denying it.

Maybe it was something about the Christmas season or maybe it could last all year long.

The only thing I could do was try to follow the feeling and see where it kept taking me!

I had decided to bring Carrie to an amusement park that was open for Christmas festivities for our date. It boasted a theme of chocolate and tinsel.

While I’d been looking her up online in the past, I’d happened to see a few of her posts with theme parks in the background and I knew she’d enjoy getting the chance to go to one during the winter.

“This is amazing. How did you know I love places like this?” she asked when we arrived at the gates.

“Oh, I just had a hunch. I thought you might like it,” I said with a grin.

“Are you kidding me? I love it!” she exclaimed in excitement and dragged me inside.

I was glad that I had brought her here… or maybe not. At first, it was fun to hold hands with Carrie and drink hot chocolate and win her a stuffed teddy bear. We enjoyed looking at all the Christmas decorations and sampling all the chocolate treats, but the most delicious taste of all for me was whenever I kissed her sweet lips, which I did frequently.

So, everything was great at first. But it turned out that Carrie was a hardcore roller coaster enthusiast. Soon I started to feel dizzy as I lost count of how many rides we tried. My stomach felt nauseous, so I suggested that we grab a bite to eat.

As we sat at a restaurant inside the theme park that served steak and salad — much healthier than the funnel cake and fried candy bars we’d sampled outside — I looked at Carrie in amazement.

I couldn’t believe that we were here together on a date. It was almost like she was my girlfriend. And I was starting to wish she was.

I was also wishing that tonight would never end.

But time flies fast when you’re having fun, and it seemed to speed up while Carrie and I were having a blast. Soon it was time to drive her home.

“Thank you for today,” I said, when we go back to her place.

I refused to open the front door of the car yet. I didn’t want our night to end.

“No, thank you. I had fun.”

She looked at me and smiled before asking, “Do you want to come inside for a bit?”

“Would that be okay?”

“Of course. Just make sure to keep your hands off my stuff.”

We both laughed at her joke as I got out of the car and opened her door for her and she got out, too.

“How about some champagne when we get inside?” she asked me. “I have some I’ve been saving for a special occasion, and I would say our first date qualifies.”

“I’d say so, too,” I told her.

I took her hand and squeezed it, glad that she was as happy about how things were going as I was.

Maybe somehow the two of us could work out even though my best friends and business partners wouldn’t like that.

I didn’t want to think about my problems and was just looking forward to toasting to our new “relationship” with Carrie once we got inside.

I was having the time of my life when suddenly, my phone vibrated in my pocket.

“Shit,” I said, pulling it out and looking at the screen for the first time all night.

I’d been having such a great time with Carrie that I had neglected my phone until now.

But as I looked at all the missed attempts to contact me, I saw that someone had been paying attention to me, alright.

14 Messages.

9 missed calls.

All from Seth.

“Is everything alright?” Carrie asked with a worried look on her face as she saw me starting at my phone.

“Yes,” I lied, putting the phone back into my pocket. “I just had such a nice time with you that I didn’t realize I’d missed some business calls. Nothing important, though.”

I told myself that if I believed my own lie hard enough, it might come true.

“Good,” Carrie said, slipping her arm through mine as we finished going up the walkway to her front door.

I’ll worry about Seth later, I thought, while she pushed open her front door without having to put a key in it first. I just want to plunge my cock deep into Carrie’s hot little pussy again right now.

She jumped in fright as soon as she stepped through the door, and I realized that Seth wasn’t going to let my wish come true. He wasn’t giving me the luxury of fucking Carrie while not worrying about him. Because he was right here in Carrie’s living room. And Jack was with him.

“Shit,” she said, breathing a sigh that sounded like it was a mix of relief and fear at the same time, somehow. “I really should start locking my door!”

“You really should, Darling,” Seth said with a crooked smile. “Because now Jack and I are going to have to punish you for disobeying us. And Clay’s punishment is that he’s going to have to watch, because maybe our mistake last time was letting him join in on it. He had too much fun and he didn’t learn his lesson.”

Before I knew it, Jack was pushing me down into a kitchen chair and cuffing my wrists to it.

At the same time, Seth was cuffing Carrie to her kitchen table, so that she was bent over with her head down and with her perfect, plump ass sticking right up in front of my face.

“You have the best seat in the house,” Jack said. “Because you’re going to watch us defile the girl you claim to be falling for. See how much you love her when you watch the filthy ways we punish her for being with you… and how much she’s going to beg us to keep doing more of it to her.”

It was just then that I saw that Jack had brought a bag. He reached down into it and got out a leather whip and a vibrator that was bigger than any of our cocks… and we were all really big and well-hung.

“Let’s see how loyal your little girlfriend is to you when she gets the feeling of this inside her little pussy and ass holes,” he said, with an evil grin on his face. “It’s going to tear her to shreds in front of you, and you’re going to wish it was your cock, but it’s not. And this punishment is better than anything we could do to you financially.”

I was relieved to hear they wouldn’t cause me harm when it came to the business.

But then he added, “Because we know how much you hate seeing something you can’t have,” and I realized that he was right — seeing Carrie’s deliciously pink little pussy and ass hole being taken by someone — and something — other than me and watching her experience pleasure and not being able to join in myself sounded like Hell on Earth to me.

And I was about to have to experience it.

Fuck, I knew I shouldn’t have taken her on a date.

But it was worth it to have her lips, her laughter, her voluptuous body all to myself for just one evening.

I guess that’s what love does to a guy.

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

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