Training: Vaginal Insertion

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When I was 16, one of my online friends suggested I get a vibrator to try things out. I didn’t necessarily felt the desire to, but what harm would getting a one-pound vibrator do? I think she told me about insertion. I don’t remember all that well, and so I tried it and I just kind of disliked it. Is this what people are raging about? I thought. What’s so great about touching yourself and inserting things?

At the same time, I was a bit curious… or what I was really interested in was BDSM but I didn’t have anyone to play with so I started buying some random toys that looked interesting which included some butterfly strap on insertable vibrator? I think I liked the idea that it could be strapped on and worn under clothes without anyone noticing.

Once I had it I managed to insert it a few times. One time I had it strapped in and sat downstairs in my joggers playing Medabots on my Gamecube and my family was just kinda walking in and out. But overall I didn’t use it much because insertion hurt. So that toy pretty much went out of the window (not literally, I still have it and just never use it).

Then when I got together with my ex we tried a bit of fingering but honestly I just didn’t like it and much preferred clit stimulation, so we also stopped doing that pretty soon.

I never used tampons apart from that one time I went swimming with my ex and was on my period. I kind of swore to never use one again because… unpleasant.

When I met Miss Lois she asked me about insertion a few times, but I was quite unenthusiastic, lol. Cause things were going slow between us anyway (I think we literally mostly talked for 6-8 months?)

Then, at some point I had been on my period continuously for 4 months, which is finally when the doctor was like: okay, maybe we need to have a look at this and figure out why. So she had to take 2 samples for something that would check if I hadn’t caught a certain disease that you can only get if you have sex with a man. Never mind that I’m gay. Guess she had to definitely rule it out (which fair enough… but also why? crying face)

So to get samples she had to insert something… quite deeply and I was lying there on the table with my legs spread, naked, obv. and completely not relaxed! So when she stuck it inside… omg… it was like this shooting pain that I just could not cope with but obviously I had to. Then the second one hurt so much more. It felt like something was ripping inside of me. And it took her ages because she couldn’t get what she wanted?? And then… then she wanted to have a look inside with a idk-what but it required insertion, again. I said that she wouldn’t be able to see anything anyway because I WAS BLEEDING. (Whole reason why I was there??) but she wanted to anyway and I was shaking and nearly crying because it hurt so much. I did not know how to cope. (Side note: OF COURSE SHE COULDN’T SEE ANYTHING IT WAS COMPLETELY POINTLESS).

Anyway. Afterwards it hurt to pee for 6 days. And afterwards I definitely never wanted to have anything inserted ever again. And Miss Lois had heard about this, of course, as it happened x months into us talking. (Side note: the period problem was eventually solved.)

Miss Lois gave me a lot of time before implementing rules or pushing my boundaries. One of the things that she gave me a lot of time on was vaginal insertion. She didn’t push me to do it. Not until she eventually thought that I was ready to try it. And tbh, if she hadn’t ‘pushed’ me eventually I would have never ever tried it myself.

The thing is, it was never just about insertion. We were always also doing other things which helped me relax and then she gave me the task to like, insert a pen or a finger. We did that a few times but we didn’t have a schedule to train vaginal insertion specifically. In fact, after having inserted my finger a few times randomly while doing other play, Miss Lois seemed to have forgotten about vaginal insertion again and I didn’t mind that she had.

But then one day, I was feeling a bit under the weather (I do quite often. Hate my immune system. Yes, I am taking vitamin supplements), but when Miss Lois came online, it brightened my day a bit.

She said that one of her other slaves had said that if I felt sick, Miss Lois shouldn’t use me, but thankfully Miss Lois knew me better than that and we both agreed that I should be used regardless if she wanted to use me.

So she told me to make two of the following:

They are cotton pads with pins struck through them, and they’re kept in place with cello tape.

After I’d made them, she told me to get my white bra and the tightest top I owned.

The only things I could think of owning were a dress I anticipated she wouldn’t like, and a rugby shirt? (which probably also wasn’t exactly what she had been aiming for, lol.)

Miss Lois: “Put the bra on, then put the pads in so they are centred over your nipple with the pins pointing towards your nipples. Then put on the tight dress with the stilettos and take a picture, and then take off the dress, put on your rugby shirt and go back to bed”

She then asked me how difficult it was to cope with the discomfort of the pads on my nipples compared to if I wore clamps. It was easier to cope with this! (clamps are the worst I swear!)

She then told me to get the marker I’d recently bought during another task (wrote about that here) and send her a picture to give her a scale of reference.

Training: vaginal insertion

She asked me if I wanted to be useful tonight while remaining in bed. Of course, I did.

Miss Lois: “Insert one index finger in your vagina, completely to the knuckle. Then show me a picture. Then insert the marker at least halfway into the vagina (you can take your finger out if you want). Take a picture again. You’re only allowed to take the pads out after you’ve taken the second picture.”

So I tried to relax and not panic and tense but… it’s difficult when you’re afraid of vaginal insertion, lol. I managed though… After a little hesitation, I pushed through the pain and pushed my finger all the way inside.

Me: “Why Is my opening so tiny?”

Miss Lois: “Don’t worry. We will stretch it.”

Me: “If this was meant to make baby’s with men then the least the creator could have done was make the openings big enough”

I took out my finger because I didn’t think adding the marker to it would help with the pain. The least I could do is free up some space… but inserting the marker was a lot harder than inserting a finger. It didn’t just slip inside…

I sent this picture and added the text that I supposed this wasn’t far enough. I knew it wasn’t far enough, it wasn’t halfway in. But it really really hurt! It’s like everything inside is trying its hardest to push the marker back out while also giving me this pain that I don’t know how to describe.

Miss Lois: “Is it halfway? You know your task. We do not negotiate tasks.”

*Inserts crying face emoji*

I mean… I knew I had to do it, I just didn’t know how. How were people able to deal with this sort of pain? It scared me. And as written above, it seemed like it actively made my body work against me.

3 minutes later I managed.

She then told me to make myself cum and to keep the pin pads in, for now, to help distract me from the pain. I couldn’t really feel the pins anymore to be honest, because the pain in my vagina was overpowering.

A few minutes later she asked me how I was getting on but I was struggling. She allowed me to stop as it had been meant for my relief, and wasn’t another punishment. (I was still on my meds at the time, so I hadn’t been able to cum since starting them. It had made trying to cum a bit of torture.)

I was allowed to go to sleep then, which felt kind of needed. But I’d been happy that she had used me regardless of my sickness.


3 Days later

As usual, Miss Lois and I had like a 4-hour conversation before she eventually then told me to get up, get naked, put on the stilettos and squat as low as I possibly could and to take a picture of it.

I asked her if I could go to the toilet first, but I had to squat first. She told me to put my legs much wider apart, and then to also put my feet wider apart. I was then allowed to go to the toilet (thank god! rather than having to pee in another container again). However, she told me that when I came back I had to put on my hood, put in my gag, butt plug and take another picture.

As you can see on the picture above, I was holding in the butt plug, afraid that it would fall out, as it does sometimes.

I was dripping wet by this point.

She told me to sit down so that the plug wouldn’t slip out, and to put my finger up my pussy. It was quite easy to put it in but it still hurt a lot to push it through the opening. She asked me what happened if I moved my finger back and forth without taking it out completely, which got more painful the longer I did it for.

So then she told me to put the heel of one of my stilettos in my pussy…

This hurt more than inserting my finger because the bottom of the heel has some sharp edges and… let’s just say that I didn’t enjoy it.

She told me that I should be feeling very horny right now, though. Which, to be fair, I did… but it also felt like my vagina was on fire.

I was then allowed to take it out and put the heel back on.

We then talked some more until eventually, Miss Lois had to go to bed, and I was quite ready for bed too.


We later moved onto inserting vibrators. It seems like it’s just, still, my opening that is tight and once something is past there it’s okay. Unless you start moving it in and out, lol!

She had me turn the vibrator on inside and tried to see if I could orgasm but I couldn’t because after just a few minutes the vibrations inside became too painful.

However, as time passed and I did this a few more times, it became less bad apart from the inserting bit.

Then she told me to get this Distance remote control insertable vibrator and I was quite scared of this purchase. No longer specifically because of the pain (although still a bit), but more so because I was afraid I wouldn’t be able to insert it (because of the pain) and therefore disappoint. I told her, of course and explained why after she asked.

Miss Lois: “When I tell you to insert the vibrator what will you do?”

Me: “Insert it I guess, Mistress.”

Miss Lois: “So nothing to worry about, is there?”

I mean… I guess? but also no? LOADS OF WORRYING.

She had also asked me to get an Inflatable butt plug.

Miss Lois: “It would also work in your pussy and mouth potentially.”

Me: “Yes Mistress.”

Miss Lois: “Isn’t that exciting?”

Em… sure… super exciting.

So then she told me to put the inflatable butt plug in my mouth and blow it up on video. She wasn’t satisfied with how much I’d pumped it up and told me to do it again and to keep pumping it, also mentioning how she looked forward to seeing me struggle with it (on video).

I certainly didn’t manage to keep it in when I started choking on it, but that satisfied, haha.

Then she told me to insert it in my pussy.

It still hurt because I was probably tense… that comes with being nervous, right, lol. But it wasn’t really a problem to get it in.

Afterwards, I had to pump it up of course. She didn’t say how much. I was happy I got to decide that, but I always feel like I should push myself so I don’t think it necessarily helped me that I could decide? She wanted to see my face while I was doing it so I filmed it as I was pumping it.

It hurt a lot.

Here’s another picture even though you can’t see any difference. It just looks weird. But the difference is that it now stayed in without me having to hold it. Another difference is that I felt full.

She asked me if the pain went away after a bit, which in a way it did but one certain area just kept on hurting. However, at first I felt unable to cope but then I was sort of ok dealing with it if I sat completely still and pretended it wasn’t there.

So of course, the next thing she told me to do was walk in my high heeled knee-high boots up and down the room three times on camera.

She complimented my walking.

Miss Lois: “You walk well on heels now.
Absolutely no comparison to what it was like.”

(Hehe, yay!)

So actually, I didn’t feel the butt plug much while walking and it hurt more when I sat back down.

We then changed to webcam and I’m not sure what we did exactly.

Then, a while later the eventual day came where I had to insert the vibrator and to my surprise, it worked! Exactly as she had said… when she told me to I just managed (although it was very, very painful).

Since then, it helped to know that I could do it despite the pain and it started becoming less painful. However, even now, it still hurts to insert it at first and it still hurts to move something once it is inside.

However, loads of progress!

Xx MLSlavePuppet

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4 Replies to “Training: Vaginal Insertion”

    • MLSlavePuppet

      I have no idea tbh. I had to go to a sexual health clinic for the period issue and the woman there said that there are many women that are very tight and she suggested going to sexual therapy or something
      But right now insertion isn’t that bad anymore, only if something goes in and out in and out. It’s just the opening? ?‍♀

      Reply
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