The First Time I Cried During a Task

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(Please keep in mind that this post was written a full year ago before the time of publishing.)

Lois and I had briefly spoken a few times over the past couple of weeks but it felt like it had been a while since we’d been able to have a full session with webcam and all. So when she came online on a Monday morning I felt happy but also a bit concerned because Monday was one of my busier days.

However, that Monday, I had been considered skipping class because the teacher wasn’t a great teacher, which generally made the class pretty useless. It was also pouring it down outside and once Lois came online I really felt no desire to attend class. 

We talked a little and her responses were quite slow, indicating to me that she must be busy with emails or something. (Sometimes she had to work but also chatted a bit with me.) I asked her for her opinion on two new black cardigans I’d bought, as I wasn’t sure which one worked better. She said it was hard to say in the vanilla pictures so for her amusement, she said, I was to dress up in the following outfit.

Afterwards, she asked me about my plans for today and I admitted I was considering skipping my class. She didn’t reply to that and changed topics so eventually, I said: “You know, I kind of expected you to tell me to go to class because you always tell me to do the right thing.”

(Side note: there was never an instance where she allowed me to skip or cancel my commitments.)

She said I was allowed to skip class if I’d pierce my skin with needles instead.

I was surprised and felt a rush of excitement in response to the needle idea and joy for the fact she didn’t tell me to go to class?! And then I felt a slight sense of fear. Lois had suggested that we’d pierce my skin with needles over a month ago as a reward for having been such a good slave, but it hadn’t been mentioned since then, apart from me saying that I’d been thinking about it a lot. So when she mentioned it and very directly told me that it was about to happen I was taken by surprise. Needles were also something I’d always been slightly scared of, not because of the needles but the idea of piercing my own skin. Of course, that made me like it more and I liked that Lois liked to push me.

She told me to order a few new items of clothing first, or rather, lingerie/outfits you might wear in a kinky club. I liked it when she wanted me to get something because that strangely felt like she was taking care of me or shaping me further into what she wanted me to be. 9 out of 10 times, the items she tells me to order are items that I’m in someway apprehensive of but then come to like when they get here. As I said, I like that she pushed my boundaries, which that was also a part of.

The next thing she wanted me to do was to put on my nipple clamps with the chain on to turn on the webcam.

I thought of suggesting turning on the webcam prior to putting on the nipple clamps because they usually hurt enough to cause some, probably, funny painful expressions, but I didn’t because I felt like I should just do what she said at this moment. 

She asked me if my flatmate was home (she wasn’t) and how I felt if she told me to go through her stuff.

This wasn’t the first time Lois had made me go through a friend’s stuff and so with that experience in mind, I didn’t feel all that much about it. I would never do it personally as it feels intrusive and it is not a turn on for me in any way. More importantly, though, it didn’t really matter how I felt because doing what she told me to was more important. I thought it was obvious that this was how I felt nowadays so I didn’t really understand why she had asked me. I guess it was just to gauge if this was still my response, or to compare my current response to the time when she told me to wear my friend’s dirty underwear.

Anyhow, she told me to go to my friend’s room and show her what it looked like. My friend struggled with depression, which is one of the reasons why her room was quite messy and she hadn’t yet unpacked entirely since moving in over a month ago.

Lois was interested in her collection of heels but my flatmate’s shoe size was about 1.5 ft smaller than mine. Yet, Lois told me to put on her stilettos, saying that surely I would find a way to manage.

I did manage to get my right foot in with a lot of effort and pushing, which hurt my toes tremendously. It’s not fun wearing a shoe size much smaller than your own! But no matter what I did, I couldn’t get my left foot in, which is a size bigger (or maybe, thinking about it, half a size? Anyway it’s bigger) than my right foot (I know, super inconvenient).

She then wanted me to look into my friend’s laundry basket and put her dirty panties in my mouth.

So you know, putting your own used panties in your mouth is one thing. It’s something I was mostly used to by then (although I no longer wore panties at that point so). But putting someone else’s used panties in your mouth… is… eh…

It’s disgusting thinking about the fact that they were used but it’s also that they are someone else’s and you can smell their scent. It’s not like I usually dislike people’s scent but smelling it on the panties is… well… definitely a reminder that it’s their panties. When I put them inside of my mouth I struggled not to gag because of the idea alone. Doing it though earned me another ‘well done,’ which was then followed by:

Lois: “Can you fit in another pair?”

Me: “Em… I can try Mistress.”

(I mean… saying no wasn’t really an option was it? I should always at least try.)

After putting in the first pair, the smell went away pretty quickly because I could close my mouth but this was not the case with the second pair which didn’t fit inside. Trying to push them in made me choke a good few times because I kept on trying and every time I choked, I could smell the scent more clearly and I had to tell myself that I should stop thinking about how this was my friend’s panties.

It was okay that they didn’t go in entirely, but obviously, I had to keep them in.

What followed was me looking through my friend’s room for items I probably shouldn’t find. The thing though, is that my friend and I are pretty close and as I have helped/forced her to clean her room before, I pretty much knew about the things she owned, especially because she recommended me the vibrator she has. It was super easy to find, because where else do you put this than in your bedside table (unless you have a specific box for your toys as I do). (Side note, my friend once asked me if my footstool could be opened (my sex toy box) and I said yes, and then she asked if I had secrets inside to which I very simply also said yes and she said: “You admitted that way too smoothly” (clearly she had suspicions, not the least because I am writing a novel about BDSM hahaha)).

However, I couldn’t find anything else that I probably shouldn’t find and I couldn’t think of anything I knew she owned either. Plus I knew where she kept what items. In my defence, she was similarly invasive on my end. She wanted to know what was in every package that arrived (which often was something sex or kinky related), (she knew that I had an online play partner, though didn’t entirely know what that meant), and she would always look at my desktop to see who I was talking to or what I was editing which often meant I had to quickly hide what I was doing whenever she randomly burst in).

Then Miss Lois told me to insert the vibrator into my vagina…

I obviously felt apprehensive about this. One because it wasn’t my vibrator and two vaginal insertions. But you know, she told me to do it, surely I could just push and force it in. So I tried and it felt like it couldn’t even find the opening. I put my finger inside, which told me I was already a bit tight because my opening sucks, then tried it with the vibrator several times and started to feel stressed because what if I couldn’t manage this?

So I closed my eyes for a second and told myself that I could do this. Just push it inside. It’s fine.

I managed to push it in and it started hurting like hell. I told myself that I should just keep on pushing, knowing that with normal vibrators it would stop hurting once inside. But as I pushed further it started to burn more and more to the point that I started crying and then I couldn’t do anything else but take it out.

My face wasn’t on camera by that point because I had aimed it at my vagina so she could see it go in. And so I kept the vibrator close to my opening, thinking I had to definitely push it in again and hold out this time but I felt so afraid and apprehensive of the pain that I couldn’t push it any further than the very tip and eventually, I dropped the vibrator on the floor and leaned off to the side while holding onto the leg of the desk as I was shaking and feeling like I was going into a breakdown.

It took a minute or so before I pulled myself together. I told myself that I should go back and at the very least tell Lois that I couldn’t do it. So I did and she asked if it was too big instead of (immediately?) telling me to try again.

I told her it had made me cry, which was definitely a first. I don’t know how often I mentioned this, but during really difficult and painful tasks she often told me that I was only allowed to stop if I cried and in all cases I never cried, unable to, somehow. Yet here it had suddenly happened, but I had felt too ashamed to show my face.

She said it was a good thing that I cried as it showed I had really pushed myself and then told me to show her my face.

I don’t really know what it looked like. I know that my face goes back to its normal state to hide that I have cried really quickly. But she reassured me. And once I was okay she told me to make myself orgasm, which made me feel slightly relieved because I knew I could probably do that.

It took me a minute longer than usual (which still was only like 3 minutes?) and it felt good for a few seconds, but I felt too distressed to be truly able to enjoy it. I did feel a lot calmer after my orgasm, however, as it had taken me back to feeling okay, rather than distressed over not being able to insert the vibrator.

Unfortunately, Lois said that she had to go very quickly now, but that I’d done very well and that it was okay that I’d been afraid to show my tears, as well as not being able to insert the vibrator.

The needles were moved to yet another date.

I was happy we’d gotten the chance to play a bit even though it was relatively short. The thought crossed my mind that maybe she was also eager enough to play for a little bit or use me to allow me to skip class. 


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