Deep Throating and Insertion

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(Please keep in mind that my dynamic with Lois ended over a year ago and this was written a while ago.)

The conversation between Lois and I started by her reflecting on how I’d been doing well, in response to thoughts I had written to her earlier. Then she immediately followed it up by a command.

“Wear 244, 232 and 229 and send me a picture.”

I can’t remember if I mentioned this before but a task she gave me about 2 weeks prior to today was to take pictures of all the outfits I owned and to sort them in folders. As you can imagine, doing this took me a few days. Number 224-254 was assigned to the Lingerie & Others folder. In addition, she wanted me to wear my heels. Unless she wanted different shoes, it was a given I had to wear these.

“Back.”

“No. Do better.”

I was a bit at loss as to what was wrong with the pictures. I’d given her two, hadn’t I? And it showed the back that she’d asked for- oh… My heels weren’t in the second picture. She confirmed this when I asked and I apologised, saying that I should have thought of that.

Five minutes passed and she didn’t say anything past that I should have indeed thought of that. I wasn’t sure what to do until I realised that she probably wanted me to redo it. I asked her, then realised my mistake for asking and added the question if I shouldn’t have already actively done it.

“Yes. I have been wondering why it took you so long.”

Shit… She’s going to punish me. Two mistakes already. Why didn’t I think of this? I shouldn’t be making these mistakes! I apologised and she said I should be proactive, noting I’m happiest when I’m proactive because I’m the best slave when I’m proactive.

 

“Would you say that picture is in focus?”

Aaaaaahh what am I doing, that’s mistake number 3!

“Will you re-do it on your own or do I have to tell you?”

Aaaaaaaaaaahhh, she’s clearly not happy about this. I’m going to be punished. Help, I’m going to be punished! I had, however, already re-taken the picture because she didn’t need to tell me. I mean, her remark was definitely just to rub it in.

“Bend forward over your bed and take a picture of your ass.”

“Lower. Your shoulders should be below your hips. And the heels need to be in the picture.”

I tried pushing myself down lower on the bed, which makes taking a picture really difficult. Moreover, it’s impossible to get the heels in like that. Bending down like that meant that my legs would be longer, which meant they fell outside of the mirror. I knew that she wouldn’t accept the excuse though and eager to avoid another mistake I realised I had another mirror stored away elsewhere. I quickly sprinted through the house (as much as possible in stilettos) and put the mirror in front of the other.

I thought I had been quite clever solving this issue but she didn’t say anything about the change in mirror. Instead, she just told me to bend over, touch my toes and to take a picture of my ass. I asked her if she still wanted me to wear my heels. I then realised my mistake and added that I was asking just because she had said to touch my toes. Then added that I got what she meant now plus an apology.

“Do you at least feel silly asking these questions?”

“I do Mistress.”

“Good.”

So relentless! In my head, I was thinking ‘it’s because it’s late (past 12 AM) and I’m sleepy,’ but I didn’t voice this, knowing she’d see it as an excuse and I didn’t want to make yet another mistake lol.

“Pull the hold-ups up and spread your legs a little.”

Shit was that another mistake? I clearly remembered the session when she wanted me to take pictures in different outfits while I had the hot sauce on my clit. Every time I made another small error, including forgetting to pull these things up and so really, I should have learned!

“I want to see your upper body more centred between your legs.”

“Your mirror is absolutely disgusting and dirty.
Sit down on the edge of your bed and spread your legs.”

I told her that I didn’t use this mirror and that I only got it from the spare room because the other one couldn’t capture my legs too when lying down on the bed and there I made a mistake.

“What was wrong with your last message?”

I actually wasn’t entirely sure lol. I didn’t accept what she had said? I tried to explain something, which wasn’t irrelevant? It sounded impolite? She said it was an excuse. Mistake number 5?? I started wondering when she was going to say that I had to get punished. Instead, she wanted to see how deep I could get the dildo into my throat.

(A while before this took place, Lois gave me the task to learn how to deep throat and since I’d been practising. I was going to write a post about that, but it’s not going to happen. So anyway, by this point, I was able to do it with the small dildo. I was able to push the second smallest one in all the way but not keep it there long. The one pictured below is the second smallest.)

Since I could do this seemingly alright, as you can see, hehe, she wanted me to use the bigger one… eh. Side note, it wasn’t actually as easy as this picture above suggests. I couldn’t keep that one in long at all and the one she now wanted me to use the one next to the black one.

Okay so anyone who has deep throated will probably know that you have to push at the opening of your throat which is surprisingly small and tight (unless this is just me, in which case joke’s on me!). Add in the extra width and it becomes impossible! Or that’s what it feels like… I told her I didn’t know how to push it into my throat so she told me to lube it (I mean I obviously already had, duh!) and to tilt my head back.

I sent her a picture and it looked like it hadn’t gone in at all.

“Relax and push it in.”

Hooooow am I supposed to relax trying to push this massive thing into my tiny little throat, it hurts!

On the new picture, it looks like it’d been pushed in halfway.

“Much better isn’t it?”

Yes… sure… I guess. But that’s all I can do okay?! No… no, she’d want me to do it again. I can try it one more time surely. And just as I had thought this she said “one last try.” That last try wasn’t much different from the one prior and the picture is almost identical. She then had the brilliant idea to make me put the middle purple dildo onto the mirror with its suction cup and for me to then push it into my mouth. Fuck deep throating, right?

The previous two pictures and the ones I mention below but am not showing will be available on my Onlyfans.

The picture pretty much only showed a close up of the bottom of my face, which showed I had successfully got the dildo in my mouth.

“Can you get more of you in?”

“I’ll try Mistress.”

“I have to apologise for my last message.”

You do? I kept staring at the chat seeing the dots move while racing through my head as to why she would have to apologise. It wasn’t so strange of her to expect another picture, was it?

“Get more in.”

I had to laugh. I instantly understood what she meant, though she asked me if I knew why. It’s because she wasn’t stern enough, which could have caused confusion in that there was an option not to manage or do it. It didn’t matter as such, because I hadn’t seen her question as anything but a command, filling in where she had slipped up and shown her humanity I guess!

I threw up on the third go but kept it in my mouth and managed to run to the toilet where I spit it out. Yes, it’s freaking disgusting! She then wanted me to turn around and put the dildo in my pussy.

(More of those pictures on my Onlyfans.)

My vagina is so tight, this really hurt. I had wanted to ask her if I could use the smaller one instead but knew she would say no and I didn’t want to risk getting punishment, which miraculously I hadn’t yet somehow! Though maybe this insertion was my punishment lol.

I didn’t push my vagina into the dildo as it was attached to the mirror because the logistics of that seemed complicated. Instead, I pushed it in and then attached it to the mirror and I can tell you that the position in addition to having something painful inside of me isn’t great!

When she was finally satisfied with the pictures she wanted us to go on cam so that I could use my wand to have an orgasm in this position…

She asked me if I prefered the dildo in my pussy or in my butt. I told her I thought I should do what would be the most painful, so, therefore, keep it in my pussy. I felt like she was surprised and had perhaps thought (rightly so) that it was really painful for me in my pussy considering I don’t take vaginal insertion well! It didn’t feel like she had asked it to test my answer and it had seemed genuine. But as opposed to earlier in the night I appeared to be fully in slave mode and have remembered all the right ways that she’d taught me.

“Move the camera a little lower.
Put it on the bed facing down.
And pull your hold-ups up, you look like a slag.
A little lower and get your hair out of the way.
Camera a little lower.
Bit higher.
Ok, make sure your skirt does not block the view.”

“Like this Mistress?”

“Yes, not make yourself come.
What are you holding?”

I was holding onto my bed with one arm because it was really difficult to keep balance and to keep on standing. Of course, she wanted me to stop doing that so…

It actually, surprisingly only took me 5 minutes to come (with a lot of effort on my end) and she asked me how it had felt. Well, it had felt like a job, lol. But I was happy enough I had managed and felt pretty accomplished considering my negative feelings towards these dildos!

Xx ML

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