She's the Boss Ch. 02

The rest of my day at work was uneventful. I taught two more classes, one of which was just administering a mid-term exam, and then I headed home to get myself refreshed for my evening with Jennifer. Our lunchtime quickie had left me craving more.

I got to Jennifer's around 6:45. She was clearly not in the mood to fuck around. As soon as her front door closed behind me, she guided me up against the wall in her foyer and dropped to her knees. This get-together was starting in a very similar fashion to our meeting earlier in the day.

"Did you shower after work?" she asked, fumbling with my belt and zipper.

"I did. Wanted to be all nice and clean for our evening together."

"Good. I haven't had enough wine yet to be tasting my ass on your dick." She engulfed my still only half-hard cock, taking it all the way down to the balls and savoring it for a few seconds. I could feel myself quickly becoming fully erect thanks to her talented mouth and throat. I placed one hand on the back of her head, lightly grabbing her hair and gently pressing her mouth back down onto my cock.

"No!" she said, with a sharp slap on my hand. I was a bit surprised, but also more than a bit turned on. "You decided you wanted to be in charge earlier, so I'm taking over for now. No touching. Just stand back and let me have my fun."

After explaining how things were going to go, Jennifer focused on getting my clothes fully removed. First she removed my shoes and socks, tossing them aside carelessly. Then she forcefully pulled my jeans and boxers down, indicating that I should step out of them. My now rigid cock bobbed in her face while all this happened. She teased me by breathing heavily on the head.

"Shirt, too," she ordered. She was really wearing her boss face this time around. I complied quickly.

Now entirely exposed in front of my lovely plus-sized boss, I stood back against the wall as she had told me to do. I folded my hands behind my back to resist the urge to touch. Jennifer remained fully clothed, adding to the power dynamic. Her massive breasts bulged enticingly in her sexy black turtleneck that was at least a size too small.

Maintaining eye contact with me, Jennifer went to work on my cock. At an agonizingly slow pace she worked me all the way into her throat, until my balls rested up against her chin. I almost lost control when I felt her tongue snake out between her lips and tease my balls. She pulled me out of her mouth equally slowly, leaving a strand of saliva lewdly bridging the gap between the head of my cock and her wonderfully hot mouth.

The connection was broken as she started to slowly stroke my shaft, first with one hand and then with both. She stared up at me the entire time, my face likely an equal mix of pleasure and desperation. I needed to cum, badly. I had thought all afternoon about our plans for this evening, and I had known better than to jerk off and deprive Jennifer of her cum. She was a demanding boss.

"Does this feel good? My hands, my mouth, my tongue... do you like this?" She maintained a steady pace jerking my dick with both sexy, chubby hands.

"Yes, Jennifer. I love it. I'm gonna cum so hard for you."

"I don't know if I should let you right now. You were a very, very bad boy earlier today. Remember that?"

"I do." I was loving every second of this. "I remember."

"What did you do that was so bad? I asked you for something, remember?" Jennifer paused her stroking to take my cock about halfway into her mouth, then just as quickly released me and resumed her luscious handjob. She was such a tease.

"You asked me to cum in your mouth."

"Why didn't you do that for me, Tyler? Why didn't you cum in my mouth?"

"Because I wanted to put it in your ass. I came in your ass."

"That's right, Tyler. You came in my ass even though I told you I wanted to swallow it. I did have an amazing orgasm, sure... but that doesn't change the fact that you disobeyed your boss at work." I noticed a change in Jennifer's expression. She was going a step beyond her usual dominant boss face. She looked authentically angry.

"I'm sorry, Jennifer. I was hoping to make it up to you tonight somehow."

Jennifer raised one eyebrow, looking intrigued.

"Good. I've decided that I am going to let you cum right now. Then after dinner we'll have some more activities in the bedroom. You can make it up to me all night."

Not wasting a moment, Jennifer resumed her oral attack on my raging hard-on. Earlier her sucking had been slow and tantalizing, but now she assaulted my cock with her tongue and lips, seemingly desperate for my load. She plunged repeatedly up and down the length of my dick, bringing me close to the edge of orgasm.

"Give it to me. Give me the load I wanted. Cum for me right now."

Almost buckling at the knees, I gave in to Jennifer's demand. I couldn't possibly hold back any more.

"Fuck, babe. Here it comes. I'm cumming." I repeated that handful of phrases in one order or another for the duration of my orgasm. It seemed like I gave her a decent-sized load.

As I tried to return my breathing and heart rate to normalcy, Jennifer did her best to smirk up at me with a mouthful of semen. I smiled down at her, anticipating the moment when I saw her take my creamy mouthful down her throat. I was surprised to see her stand up without swallowing. I'm sure my face betrayed my confusion.

Jennifer moved quickly to pin me up against the wall. She held both of my wrists stationary against the wall while she used her ample body to keep me from going anywhere. Still smirking at some secret joke, she moved her lips towards mine. That's when I got the joke.

Payback. I wouldn't give her a load to swallow earlier, so she was going to give me one now. I started to panic.

"Jennifer, no. Come on, we've never d-..." My protest was cut short, for obvious reasons.

Feeling her lips press to mine, I decided to give in. Not that it would have been easy to get out of the situation if I'd tried. Jennifer was significantly larger than me, and perfectly capable of dominating me physically if she decided to.

Her tongue forced its way between my lips, bringing with it my first taste of my own semen. As both of our lips opened wider, Jennifer began pushing the load into my mouth. As I had suspected initially, it was a lot of cum.

I'll admit that I was in a very weird spot mentally at this moment. On the one hand it was sexy because my boss was dominating me and using me for her own gratification, regardless of my protests. It turned me on. But on the other hand, how did girls swallow this on a regular basis? I had a momentary flash of guilt thinking of all the loads that girls had swallowed for me without so much as a grimace.

As I wrestled with the idea of swallowing my own cum, Jennifer looked on with satisfaction.

"Isn't it tasty? Don't you see why I wanted it so bad today?"

My lack of response was all the answer she needed.

"Do you want to swallow it?"

I shook my head, hoping that Jennifer would ease up on me.

"Okay. Give it back to me then." I was saved. A wave of relief washed over me. As Jennifer had said earlier about tasting her ass on my dick, I wasn't nearly drunk enough at this point in the evening to be experimenting with swallowing my own semen.

Jennifer leaned in to kiss me, and we reversed the process from earlier. I got as much of the cum back into her mouth as possible, leaving only the taste of it behind in my mouth. As soon as the transfer was complete, Jennifer gulped it down happily.

"I'm a good boss, Tyler. That's why this time was just a warning. But let's be clear... Next time you misbehave like that when your boss tells you to do something at work, you are going to be the one swallowing that load."

"Got it, Jennifer. Thank you."

"Okay, now let's get on with our night. Dinner should be almost ready."

*

Our after-dinner antics are a story for Chapter 3.