My Boss is a Cougar

I feel myself blush.

"Okay, yes I, umm, have noticed what goes on in this office."

"Yes, I've made sure of that."

"You have?"

"Yes, I've been noticing you from your first day. It's not just about looks. I mean, you are incredibly attractive. I brought in Mark from HR, not because I think he's attractive. He's enough, but I did it to show you first hand what goes on."

"Well it definitely worked."

"You have the mind for this kind of work. And that's what I like about you. You have the appearance that backs up your professional talents. I admire that, but I wanted to test your patience. I'm sure the other guys have told you what I do, so I wanted to see if you would wait."

She unbuttons her cardigan and takes off her earrings. I say nothing, just watch.

"And now it's finally your turn."

She closes the blinds.

My head is racing. This is actually happening, it's actually fucking happening. My dick is hard as a rock and I can already feel some sweat. I know I should be happy, but I'm actually just nervous as hell. How am I supposed to tell her that I've never done this before? Would she just end it? What would happen? But I can't keep it from her. I'm excited, but I also want to just open the communication early.

"Wait Clarissa, I just have to tell you. I've never done this before."

"Russ, it's fine, not a lot of people have fucked their boss."

"No, it's not that, I have never...had sex...before."

"Oh, I see." She says softly.

"That's fine, I don't mind, I can guide you through it." She reassures me.

That was the biggest hurdle I thought I'd have to overcome, but she blows it past like it's nothing. Sometimes in this terrible world, the most terrible things are our own thoughts. It turns out to not really matter in the long run.

"There's some lube in my top desk drawer, how about you take off your clothes, and find it."

I do what she says. I take off my shoes, shirt, and slacks. I'm not the most built guy, but I think I give off a lean persona that is still enticing and enough to work with. I reach into her top drawer and grab the KY Lubricant. I've only seen this stuff in stores, never held in person. I grab it and I look up at Clarissa. She's laying on the couch, completely naked. She had this glow to her skin, and her hair was a perfect accent to her skin tone. Her tits looked immaculate and her soft yet enticing eyes felt like she could see right through me. She was my boss, but she was beautiful.

"I'm ready." She faintly whispered.

"Oh alright." Still a little flustered from seeing her like this.

"Yes, come over here and we can begin."

I walk over to the couch and she sits up. She reaches up to grab the back of my neck, and she draws me in closer to her. She kisses me for a few moments. I have had a few kisses in my life, but they weren't this good. She knew how to work her tongue, and all I could do was act like a dog who had some peanut butter. Clearly not the best at this.

She laughed.

"Alright, I can take it from here for a bit."

She releases my neck and she goes for my dick, first giving me a short hand job before going in and sucking me off.

"Sorry, my hands are a bit cold."

"No, you're fine" I say with almost half a breath.

It felt amazing, all these sensations running through my blood. I totally understand the appeal behind this. She goes faster and harder, and it takes all of my energy to remain composed. Maybe this is another test. She stops after a bit.

"Okay, now it's time. Here's what I want you to do. Put some lube in my hand, and have a seat on the couch.

I do as she says. I open the cap and pour a little bit into her hand. She starts spreading it around her pussy, and I take a seat. Since I'm hard as a rock, Clarissa simply crouches on the couch and sticks my dick right inside her. Then she starts just grinding on it. As she's facing me, I start to suck on her tits. That seemed like the appropriate thing to do, and I wanted to do it. I had been admiring her tits for awhile now, ever since I saw her, and while they were in front of me, I had to indulge. They were nice, plump, not too big, and delicious. I can feel her vividly, I'm inside every bit of her, the lube is really helping. I can see why there are so many stains on this couch. After a few minutes, I'm surprised I haven't bust yet, but so far so good.

"Let's change it up some. I'm gonna stand over my desk. I want you to find the hole, and then go at it."

Her instructions weren't condescending at all. She was genuinely helping me and made me feel like an equal. For my first time, this was going very well. I did what she asked. My dick was super slippery but I think that was an advantage. She leaned over her desk and spread her legs. Breasts on her keyboard. I find the hole, and I can definitely feel the inside of her. Then I start doing my thing. Thrust after thrust after thrust. Even though it's my first time, I feel pretty good about this. I'm only doing what seems natural and what I've seen on the Hub. I haven't finished yet and we're just having fun. In this moment, we aren't boss and subordinate. We're just two people having a connection after a shared existence of being in the same place at the same time. I can hear her gasp and moan a bit. She grabs the edge of her desk tightly. She's a smart woman, so I don't know for sure if this is just a bit or if she's genuinely enjoying this. All I know is that sometimes, I overthink the moment and think too much. I need to enjoy life, I need to live in the moment. Not everything is an angle. Sometimes there's not a deeper meaning. Sometimes, the meaning is that you're just fucking your boss.

"Damn, you're pretty good. Are you sure you've never done this before."

In between grunts, I let out "Thanks...I'm just trying my best."

"Well I want to try something else. I'm gonna get on my desk, I want you to do exactly what you've been doing."

She gets up from leaning on her desk and is now just laying on it.

"Okay now stand close to me, and sort of lean a little bit so I can rest my legs on your shoulders."

I follow her instructions, and I'm insider her once again. Her ankles are resting on my shoulders and I take deeper thrusts now. My arms are wrapped around her thighs and I'm able to keep going at a constant pace. I find that I'm not really doing much at all, but I can see it's doing a lot for her. She's biting her lip and looking up at the ceiling. Once in awhile she would smile and look at me. I'm getting a little tired at this point. For a minute, we both stare at it going in and out, in and out, in and out.

"When you're about to cum, let me know."

"Yes ma'am"

After a few more thrusts, I inform her accordingly.

"Okay, now right before you do, pull it out and cum on my chest." She says.

"Okay" I say.

I pull out, stroke for a few seconds, and cum right on her stomach and chest. I breathe deeply and grunt with each rope, and there were quite a bit, I hadn't jerked off in weeks. The buildup after a hand job, blowjob, and 3 positions was massive. We share a moment together looking at my work.

"Good job, that was amazing. There are some tissues on the table there." She points to the right where a small table is. I grab a few and wipe away the cum from her chest.

"Such a gentleman too." She says with an endearing smile.

I laugh, "Thanks"

I go to put my clothes back on, then she suddenly says. "Not yet, please indulge me."

She gets up, doesn't put her clothes back on, and lays on the couch. "Join me Russ."

How can I say no?

I move to the couch, and I sit with my back resting on her chest. She raps her arms around me, we're both still fully naked, but at least the blinds were closed. For a few minutes, we sit in silence. Just sharing a space, sharing a moment in time, every once in awhile, she would stroke my hair or something, or kiss the back of my head. Then she breaks the silence, with 6 simple words, "I've never kissed an employee before."

My life before this job was non existent. I had no life, nothing really, a few friends but nothing important ever happened. I wasn't anyone. I tried to break out of that shell, do something new and exciting. So I got a job, a job I enjoyed with fun people, and an even better boss. She made me feel important, she made me feel special, and she felt just as good. With this experience, I feel a greater sense of confidence. Because at least now I know, that at least one person likes me. That will keep me going, and it will keep me going back to Clarissa's office.