Shes The Boss Ch 01 1

"Tyler, could I see you in my office for a minute?"

I looked up from my desk to see my boss, Jennifer, standing in the doorway to my classroom. She was looking especially sexy today in a tight green turtleneck that accentuated her massive breasts.

To be honest, every part of Jennifer was big. I've always had a thing for larger women, but Jennifer was by far the largest woman who had ever caught my eye. She was probably around 300 pounds, with a beautiful round face and gorgeous lips that seemed to be pleading for a cock between them. She usually wore her reddish-brown hair back in a ponytail, but today she was wearing it loose. I loved when she did that.

Snapping out of my mini-daydream, I told Jennifer that I'd be right down to her office. Fortunately I had just finished grading the last of my morning class's quizzes, and still had another half hour left in my planning period.

Reaching her office, I knocked on her open door. She got up from her desk and approached me, reaching around me to close and lock the door. When I heard the lock go, I knew this would be one of our fun meetings.

The door was hardly closed when Jennifer dropped to her knees and placed her hands on the front of my jeans, massaging the already growing bulge there. She fumbled briefly with my belt and zipper before managing to get my cock out of my pants, and she immediately started stroking.

"Sorry to disturb your free period, but I forgot my lunch at home and figured you could maybe feed me something." Saying this, she plunged down on my dick, taking me all the way into her throat on the first go. Jennifer was experienced with this.

Suppressing a moan, I closed my eyes and enjoyed the feeling of being deepthroated by my boss. Even after a few weeks, it still hadn't gotten old. I placed one hand on the back of her head and gently followed along with her motions as she lovingly sucked me.

"Jennifer, we are so going to get caught one of these days." My boss looked up at me as she once more took me down to the base of my throbbing cock, then quickly removed me all the way from her mouth. She stroked firmly up and down on my cock, which was now well-lubricated with a healthy coating of saliva.

"No worries. Vanessa is the only one next door and she knows, more or less."

"She knows?! You told her about this?"

Jennifer kept stroking as she smiled up at me. "Well I didn't want to, but she figured it out. She told me one day that she noticed how different I seemed before and after my meetings with you. She kind of implied that she knew what was up. But seriously, don't worry. I've got dirt on her too, so she won't tell. Can I get back to work here?" Without waiting for an answer, Jennifer swallowed my cock again. This time when she had it all the way down, she extended her tongue to lick my balls. I could already feel an orgasm building.

I let her keep this up for about another minute before I decided to change things up. I needed more than just Jennifer's mouth.

"Bend over the desk." I tried to make my voice as dominant and assertive as possible.

"No, I don't have time for that. I just want a little treat from you before my meeting. Maybe after work you can come over. Now, I want the load that I brought you in here to give me." She was using her no-nonsense boss voice, which I found incredibly sexy.

It was tempting to go ahead and just blow my load in her warm, waiting mouth. She was an incredibly talented cocksucker, and I loved seeing her already full cheeks bulging as she swallowed for me. But I also knew that despite her assertiveness, she had a submissive side. I gambled on her being in that kind of mood.

As she moved to deepthroat me once more, I pulled my cock away from her. She looked up at me with a raised eyebrow.

"Something wrong?" she asked.

"No, but I just think that if we're going to misbehave at work like this then we should really make the most of it."

A confused look crossed her face, followed by a look of realization. While she processed my intentions, I forcefully raised her up and spun her around, so she was facing her desk. Dropping to my knees, I lifted her skirt and pulled her panties down to her thighs.

With one massive ass cheek in each hand, I spread her open to expose her tight asshole. With the element of surprise still in my favor, I pressed my tongue to her glorious little hole and began to orally ravish her. I started with short, rapid flicks of my tongue against her puckered hole, followed by several deep plunges as far in as I could go. The first of these elicited an indignant squeal from my boss.

"Tyler, no, we can do this all you want later. I have a meeting in 5 minutes." While protesting verbally, she did nothing to stop me or move away.

"I know. And you're going to sit through that meeting with a big load leaking out of your ass into your panties." I gave her backdoor one more long, passionate lick, making sure to get it nice and slippery. While just using spit for lubrication wasn't ideal, it had worked for getting my seven inches into Jennifer's ass before, and it was the best option currently available.

"OK, fuck, just go quick. I'm serious."

I didn't want to make Jennifer late to her meeting, but I did want to savor this feeling of dominance for just a little bit longer. I pressed the head of my cock to her asshole as I grabbed her hair and tilted her head back just enough to make eye contact. The look on her face was one of mild frustration overshadowed by lust and arousal.

"Just save your breath for the meeting and take this load when I give it to you."

She moaned lightly as I let go of her hair and placed both hands on her ample hips. I pulled her back to me as I slowly, steadily pushed into her asshole. This caused another moan, lower and more guttural. It was difficult with no real lube, but I managed.

I wish I could say that I came almost immediately because I wanted to get Jennifer to her meeting on time, but the truth is that I couldn't have held off if I wanted to. Seeing Jennifer's massive ass split by my hard cock was absolute heaven, and it always made me cum incredibly fast. I like to think I have decent stamina, but not when it comes to Jennifer's ass, and especially not after the incredible deepthroating I had gotten from my boss at the beginning of this session.

As I started to shoot deep into her incredibly tight ass, I felt her body tense up and quiver slightly. My orgasm lasted about ten or fifteen seconds, after which I stayed in her for another half-minute or so, savoring her warmth. Pulling out of her, I was greeted with the sight of my cum beginning to leak out of her.

Jennifer straightened and pulled up her panties, depriving me of any more time to enjoy the visual. When she turned to face me, I was relieved to see a blissful smile on her face.

"Thanks. I enjoyed that. Still want to come over later?"

"Sure, if the offer still stands."

"Of course. I'll make dinner. After that you have a load or two to feed me."

The rest of the day dragged, but that night was worth the wait.

To be continued...