A New Number 2

This is another tricky one. I can see benefits to both. Helen helping to manage my other girls would take a huge load off my shoulders, but it would be just as nice for her to have the ability to perform tasks for all of us at all times. I mull the options over a few more times before an interesting idea pops into my head: I wonder what Helen would prefer. Outside of Violet, I've never really considered the girl's opinion when doing one of these. And even with Violet, she ended up wanting me to choose anyway.

The more I think about it, the better of an idea it sounds like. You know what? Maybe I should ask her. Helen has been nothing but helpful to me since I used the remote on her, something I can't say for many of the other girls. Giving her some agency to choose what she turns into feels like the least I can do. I spend a moment thinking carefully about how I'm going to phrase my question, then once I figure it out, I try to subtly hide the remote as I step into the office.

As I enter, I notice that Helen is facing away from me, digging through a filing cabinet. Her position gives me an opportunity to see her nice ass as it's hugged by her pencil skirt. I definitely won't complain about a sight like that.

"Oh, Mr. Anderson. I apologize. Give me just one moment," She says as she hears me enter.

"It's alright, Helen. Take your time. Actually, do you mind if I ask you something?" I respond, seeing this as the perfect opportunity.

"Of course not! Ask me anything you like, Sir. I'm hear to serve you in any way I can."

A small shiver runs down my spine when she says that. I've developed quite the kink for subservient women recently. Or maybe I've always had it and only now is it finally coming to the surface.

"If you had to choose between being able to manage other people or being able to do as much work as you want on your own without needing sleep, which would you choose?" I ask.

"I assume this question is in the context of my employment with you?" She asks.

"Yes, that's right," I clarify.

Helen pauses to think for a moment.

"Hmm... it's not an easy choice, but probably managing others. As long as I would still be work for you, of course. As much as I would love being able to work all the time, having other people to delegate things to would allow me to do so much more for you in the long run," Helen explains.

Well, I guess I can't argue with that logic. It's funny that Helen seems to choose her answer based on which one she thinks would benefit me more. I guess she really does like working for me. Still, I'm happy with her answer. I was actually leaning toward option A myself. I probably was going to pick it before I came up with the idea to ask Helen, so this works out pretty well.

There is a part of me that feels a little bad to do this when Violet has been acting as my second-in-command for so long, but after thinking about it some more, I realize she probably wouldn't mind Helen taking a leadership role. If anything, she might actually like having another person order her around. And besides, just because Helen is in charge of my other women doesn't mean I care about Violet any less. She'll always hold a special place in my heart that no one else ever will.

"May I ask why you wanted to know that, Sir? It was an oddly specific hypothetical. You don't have to tell me, but I can't help but be a bit curious. Am I up for a promotion?" Helen asks as she glances over her shoulder at me. A moment later, she looks back down at the files in front of her.

"Something like that..."

With a decision made and Helen facing away, I take the opportunity to lock in her choice. Since A is tied to the green button, that's the one I hit.

New Attribute Selected

RIGHT HAND

"Once again, I'm sorry for the delay, Sir. I-" Helen starts to say as she turns around, holding a folder in front of her. I assume that was what she was looking for. However, once her eyes lock on me, her voice trails off.

For a moment, Helen just stares at me, her mouth slightly hanging open. She looks me up and down and her face turns red, but only for just a brief moment.

"Are you alright, Helen?" I ask.

"I... um... y-yes, Sir. I'm sorry. I was just distracted by something," She replies as she puts the folder down on her desk before walking around to the front of it. "Have I told you how good you look today, Sir? Because you look fantastic."

It looks like the new attribute is already working its magic. This must be the added attraction she just gained. She's never acted this way around me before. She was always happy to help, but it was always just business before. Now, the look in her eyes is that of a much more personal desire.

"Where are my manners? I haven't even offered anything to you. How can I please you, Sir? I'll do anything you want," Helen practically moans out in a sensual voice.

As she reaches the front of her desk, she leans against it before pulling up her skirt a bit and tugging at her blazer. It's at that moment that I realize something about Helen's outfit that I hadn't noticed until now...

She's not wearing anything under that blazer! And now that I can see her legs, it doesn't look like she has anything on under her skirt either! Wow. And she thought I looked incredible. She may be the oldest woman under my control, but she's still got it. But wait a second... she only just now started to find me attractive (at least I assume), but she had to have her outfit like this before I came in.

"You look so sexy, Helen, but I don't understand. Why are you dressed up like that? I've never seen you in such a revealing outfit before," I say.

"Part of my job is to make sure you're always satisfied, Sir. That includes sexually. I reason that exposing more of my body would help achieve that goal. Besides, it's much easier for me to provide you with relief if I don't have any pesky underwear in the way," Helen explains.

Leave it to Helen to go commando just for the sake of efficiency. I'm about to respond to her, when she suddenly starts speaking again.

"I... I need to admit something to you, Sir. I just realized that I have feelings for you. I don't know why I didn't realize it before, but it has become very clear to me now. I really want to act on these desires, but I'm afraid they may affect our professional relationship. I... I understand if you want to... find a new assistant because of my inappropriate behavior."

Helen looked like she got visibly ill trying to say that last sentence. The remote ensures that she thinks she's my assistant, so the thought of me firing her probably really hurts. I mean, if I did that, it would completely destroy her purpose in life. Aside from not wanting to break this poor woman's heart, I also have no desire to entertain such a ridiculous thought. Like I'm ever going to give up my favorite little worker bee.

"Don't be silly, Helen. I'm very fond of having you work for me. In fact, I'm very fond of you in general. As long as it doesn't interfere with your work, I would have no problem taking our relationship to the next level," I tell her, which causes her eyes to light up.

"Really? Oh, thank you, Sir! I promise this will only make me work even harder for you! But... aren't you already dating Ms. Garcia?" Helen asks.

"Violet and I have a very open relationship. Actually, I want you to think about Violet for a moment. How do you feel about her?" I throw out, curious to see her answer.

Helen pauses to think. After a moment, a mix of realization and surprise crosses her face.

"Now that I think about it, Ms. Garcia is also very good-looking. She's... beautiful actually. That's so strange. I've never been attracted to women before, but thinking about Ms. Garcia right now has my heart racing. W-when you said you had an open relationship, does that mean...?"

"If you're asking if you can be with both of us, the answer is yes," I respond.

"Hold on... you want to build a harem. I can sense it. I'm not sure why, but I'm certain I'm right." Oh yeah. I forgot that Helen had the ability to sense my desires because of her ON THE SAME PAGE attribute. I'll be honest, it's still a little freaky when she does that.

"Does that bother you?" I ask, seeing no reason to lie to her.

"Of course not. In fact, if you'll allow me to, I'd like to help you. I want you to be surrounded by beautiful women like Ms. Garcia. And me, if it pleases you."

"That sounds like a wonderful idea, Helen. Perhaps you could even serve as the head woman in my future harem." My assistant smiles at those words.

"I would love nothing more, Sir."

I walk over to her and kiss her. I can tell she's not very experienced with kissing, but it doesn't matter. There's something about making out with the dean of my college that I can't get enough of. I know Helen has always chosen to focus on her career over her relationships, but hopefully with time, I can teach her to strike a healthy balance. A minute goes by and we break our kiss. Helen seems a bit upset when our lips part, but she also clearly wants to get the meeting started.

"Alright, Sir. I have a few things I would like to talk to you about. Would you like to use my vagina while talk?" Helen asks as she preemptively hikes up her skirt.

I think that might be the strangest way someone has ever asked me if I want to have sex. Still, I'm not one to say no to a beautiful woman's pussy. After agreeing, Helen tells me to come around her desk with her. Once I do, she immediately bend over and pulls her skirt fully up, exposing her soft ass and waiting pussy lips. Looking between her legs, it seems like she's already wet. Not needing anymore encouragement, I drop my pants and enter her from behind.

"Mmm... now, I've been trying to work on finding potential new revenue streams for you, but I'm having some issues," Helen begins as I plow her.

Wow. I wasn't expecting Helen to still be able to focus while I'm fucking her like this. Aside from the occasional moan, she barely reacts as I repeatedly thrust into her. I have no idea how she's doing it. Honestly, there's something kind of hot about fucking someone who's completely ignoring the fact that you're inside them. Is this why people are into freeuse stuff? If so, I totally get it now.

I have to really focus to try to keep up with what Helen is saying. I'm not exactly used to doing business like this. But at this point, there's no chance I'm pulling out of this MILF's hot pussy. Anyway, I'm pretty sure she said something about revenue. Wait, is she talking about me earning money?

"You see," Helen continues. "I was hoping you would be able to tell me about some of the other... mmm... assets you have available to you. I believe if I knew what else besides me... ah.... you have access to, I could find a way for you to make a profit."

The way Helen says stuff like "assets" and things I "have access to" only makes me hornier. Still, I think I'm able to follow where she's going with this. She must have figured out that I've been concerned about money recently. Another result of ON THE SAME PAGE, I'm sure. She probably doesn't know all the details, like the fact that my mom won't be able to work on account of her thinking she's a dog, but she knows enough to feel the need to do something about it.

So she wants to know what other resources are available to me? Not much honestly. I mean, I am just a boring college student without anything to my name. Well, I guess I was boring. Actually... I suppose there are a few things I technically have access to now... but do I really want to say that out loud?

"You mean like other women?" I blurt out.

Whoops. I didn't mean for that to slip out. God, I really shouldn't be trying to make important decisions while I have my cock inside a woman.

"There are other women? Do you mean like other potential harem members? Besides Ms. Garcia and I?" Helen asks.

"Um..." I mumble, not sure what to say.

"Please, Sir. Don't be afraid to tell me anything. I just want to help you. If you... ooh... believe these other women could potentially be useful to us, I would like to know about them. And I believe I've already made my stance clear on sharing you. I promise... mmm... that I only want to aide you in anyway I can."

As Helen says that, I feel her pussy tighten slightly on my dick. Oh man, that feels so good. I'm not sure if she did that on purpose or not, but she really does always seem to know how best to please me. I grab a fistful of her hair and start thrusting faster, something that Helen doesn't seem bothered by in the slightest. If anything, she seems to get a bit more into it when I do.

As I start to feel my arousal build, I'm left wondering something: should I tell Helen about what's been going on? I don't have to tell her everything, but it might be worth it to give her some information. After all, I did just make her my right hand woman. Her new power doesn't really work if I don't tell her about the women she has control over now. And it's not like I don't trust her. She's probably the most trustworthy, reliable person I know right now. It's almost certainly either her or Michelle.

Okay, I think I know what I should do. Hopefully I was able to fully think this through despite the approaching orgasm. Now all that's left to figure out is what exactly I want to say to Helen...

…oh yeah, and I should also probably figure out where I want to cum...