[Fiction] Cyber Mistress, Part 2 - Reluctance

[Hasjtag]

Read Part 1 here first!

Hi again! Sorry for the long wait. I had some difficulties finding the right pace and the right balance between plot and spice. I let it rest for a while and plan to be a lot quicker with the next parts. As always, your feedback is very much appreciated!

1.

All I can think about is Fenna while I sit here, kneeling in the center of the room. My laptop is open a few meters in front of me. My knees are far apart, my butt is resting on my feet, and my hands are folded over each other behind my back. I try to keep my back as straight as possible. The leather harness helps with that, because it's so tight that I feel every deviation of my posture on all the straps. Especially the one that runs between my butt cheeks and is interrupted by a ring around my scrotum where my chastity cage goes through.

Miss Daisy likes to be specific. Very specific. She made me mark the holes on the harness straps she wants me to use, so I won't go easy on myself by putting it on loosely. This position I try so hard to remain has also been thought to me in detail. Nothing is left open for interpretation. Even though she doesn't see me right now, the webcam can turn on at any second because Skype is on auto-pickup. And when it does, she will notice if I quickly adjust my position, so I make sure to keep my back straight and chin up at all times. I'm not sure if I'm hoping she will be here soon, or she lets me wait. She might even just message me at some point that I'm dismissed without checking in at all. She knows I will do as she says anyway, simply because there's a chance she checks.

2.

I have been here for about 40 minutes when the video call suddenly starts. To my surprise, Miss Daisy shows herself again. This time she has her usual subtle black eyeliner on, and she wears what seems to be a blue dress with lace details. She is even more stunning than she was this morning. I quickly make sure my position is absolutely perfect. I need all the favor I can get from her to have any chance to meet with Fenna this weekend.

"Well, well, look at my little sleepy boy", she greets me with her usual grin
"Good afternoon, Mistress" I say formally, as I'm supposed to

I immediately feel the excitement between my legs. It's embarrassing as I'm sure she can see my chastity cage twitch, but I have no option to hide it. My knees need to stay far apart, and I'm fully exposed in front of the camera. There is no point in trying to hide anything from Miss Daisy.

"I'm glad that you're here," she said as though I had a realistic option not to, "there are a few things I want to discuss"
"Any time, Mistress"
She leans back in her chair, probably just to make me envy how comfortable she is while I'm not allowed to move at all.
"I feel like you've been slacking a bit lately, especially this morning, of course. When I tell you to get up at a certain time, that doesn't mean you can go back to sleep right afterward!"
"I'm sorry, Mistress. I'm not sure what happened."
"Don't worry about it" she replies with a surprisingly sweet voice. I did not expect that reaction.
"I can't fully blame you for it. As your mistress, it's my duty to keep you in check and I haven't done so enough. I've been giving you too much leeway, and I want to change that from now on."
My eyes widen, but I try not to show how shocked I am to hear that. Too much leeway? I feel she has been micromanaging me almost right from the moment we started three weeks ago. What more freedom does she plan to take away from me?
"I will be giving you more tasks to keep you busy in your spare time, that should prevent you from getting bored and falling asleep" she says before I can think of something to say myself. "And I've also found an app I want you to install after we're done today. It gives me real time insights in your phone usage and GPS location. And it works for both you phone and laptop, isn't that cool!?"
I feel some nerves coming up at the thought of it. Normally this fear would be combined with excitement, but right now I have Fenna on my mind, and I would much prefer to be cut some slack instead of the reins being pulled tighter.
"Shoulders!" she says, interrupting my thoughts. I forgot to focus on my posture and quickly correct myself.
"Yes, Mistress. And very cool indeed. I will install it immediately after this" I say, while trying to sound enthusiastic.
"That's a good boy! Now how is my little caged dick doing?"
"Good, Mistress. Though it's getting more and more frustrating each day"
"Perfect. I think you deserve a little treat. Crawl to your room and bring me the dildo, with your mouth of course."
"Yes, mistress"

3.

On my hands and knees I crawl to the bedroom, open the drawer and put the dildo sideways between my teeth. As I crawl back, Fenna keeps coming up in my mind. What would she think if she saw me like this? I try not to think of her. My love for Fenna and my submission to miss Daisy seem like two different worlds that should never come together. With Fenna I just want to kiss and cuddle. If I were with her, I would certainly leave this life behind completely. She should never know, she would be horrified by this. She's way too sweet and pure.
I have to focus on miss Daisy now, like it or not. After I place the dildo on the ground in front of me with my mouth, I quickly use my hands to place it vertically with the suction cup sticking to the floor and get back in kneeling position.
"Good, now lick it for me"
"Yes, mistress" I say right before I bend over and gently caress the tip of the dildo with my tongue. I focus on the head, but sometimes run my tongue by a side or give it a passionate kiss or two. She likes it when I put up a show, and I try my best to look like I like it as well.
"Good slut. Now suck it"
I place my lips over the tip and slowly start to move my head up and down, steadily increasing the rate of motion. Then Fenna appears in my mind again. It makes me so ashamed of myself, I just want to sink in the ground. I realize I could have been on a boat with her if it wasn't for these weird desires that are starting to consume my entire life.
"Deeper!"
For a split second, I consider closing my laptop and leaving this all behind. I'd have a normal life just like everyone else.
But instead, I obey.
"Now it's time to give that little asshole some attention. Get on it!"
I get straight up but with my knees still on the floor. I move forward a bit, so I'm over the dildo that is straight up on the ground. Slowly I drop myself to get my asshole near the tip of the dildo. It's difficult while holding my hands behind my back, but I've had some practice with this. It takes a few attempts until I get the position just right, so the dildo slides inside me as I move down. I get as far as I can, feeling the dildo penetrate me deeply. Then I move up again, so only the head of the dildo stays in. And down, and up... I feel my mind get vague as I feel the arousal take over my body. My cage is so tight it feels like it might explode. If only it did, that would be such a relief. But I know damn well it won't and my dick is going to stay all compressed and pointing downwards in there. I always thought chastity would make me miss having orgasms, but it's actually erections that I miss even more. Every erotic thought (and I have a lot of those) is immediately answered with denial from the cage. It's not that I'm just not allowed to masturbate anymore, it doesn't even allow me to just enjoy arousal.
Fenna is no longer on my mind as I fully give in to the dildo and my submission to Miss Daisy. I would do anything for her right now. Every penetration from the dildo feels so good, and I barely notice my legs getting tired. I wish this was Miss Daisy fucking me right now. In some ways, it feels like it's her. She is the one in control of the situation. She is in control of it all.

4.

"That's enough" she interrupts me.
"Yes miss... thank you miss..." I whimper. I get off the dildo and in normal kneeling position behind it. My body feels like it's made of jelly, and I'm slightly trembling.
"Good boy. Now, you haven't informed me about any plans you have for the weekend. Are there any changes to your agenda?"
"Well, actually..." I begin. Then I pause for a bit. What should I tell her? Making up something else would always have been risky as she might check in on me, but now that I will be GPS-tracked, it's definitely not an option. Or is it? She would know where I am, but not with whom!
"I... I got invited my some friends to go on a boat trip this Saturday. I would really like to go. May I please, Mistress?"
"Hmm, that sure sounds like fun! If you behave well, I will let you go."
"Thank you, Miss Daisy!" I say, while I also feel a strange sense of guilt come over me. This might be the first time I lied to her. What if she finds out? And is it even a good idea to meet with Fenna like this? What if Fenna finds out?
That will be a worry for later. First, I need to install the app and surrender my last bit of privacy to Miss Daisy...