Examining my vaginal training progress

As you may know, Mistress gave me the task to train myself to be able to insert vaginally. I have been doing this task daily for almost two months and managed to go up quite successfully in dildo size. I’m genuinely surprised that I’m being successful. I can actually move a dildo inside of my vaginally without pain, even if the initial insertion still hurts.

Examining my progress

Mistress was over at my flat and said I was to show her my progress with the dildos.

She cuffed my hands together, then told me to come on her lap with my elbows leaning on the arms of the couch so that she’d have good access to my bum hole. I like it when she asks me to present part of myself to her, while sort of sitting on her lap. It feels very intimate and a little humiliating at the same time because I know she’ll get to see my bum hole super up close.

She started by putting lube on my clit and vaginal hole, which was a little unexpected because I thought she was simply going to put the butt plug inside of me. Instead, she seemed to start exploring my clit and gently stroked around it in such a way that it felt pleasurable and it made me relax into her touch. Then she put her finger inside of me, which surprisingly didn’t hurt, but I was taken by surprise. I felt aroused by the idea that she’d simply decided to play with me for a bit. And the fact that she put her finger inside of me felt like a claim of ownership (because I don’t allow anyone else to do that).

Her touch went from gentle to more arousing, and soon after my clit became a bit too sensitive to know whether this was still enjoyable to too much. She was clearly getting a response from me by this point, and that in and of itself was enjoyable for me too. Again, it felt like she was just having fun with her “toy” and if it meant she enjoyed it more by stimulating me too much, I only enjoyed the thought of it.

At the same time, it felt quite significant that I enjoyed the sensations of her touch at the start of it, because I haven’t really been able to enjoy sexual intercourse with other people when I am being touched. I can’t relax and feel too much pressure to enjoy it, I guess. But I feel so at ease and safe around my Mistress that I’m apparently able to enjoy these sensations.

Inserting the butt plug

She then finally inserted the butt plug (which is always a pain, because the inflatable one is so flexible that it always wants to slip out.) But once it was in and she inflated it I could immediately feel it. Whether I can cope with the sensation depends on how constipated I am at the time (lol, sorry but maybe relatable for some people?) Turns out today, was not the best day for an inflatable butt plug for me. However, that made Mistress enjoy it all the more!

She inflated it several times until I was making clear noises of agony. After a few seconds, she deflated it again, then held onto my body so I couldn’t get away and re-inflated it and again, I felt like I would never be able to cope with this. It’s funny how I can so easily take x amount of strokes of the cane but struggle with a little inflated butt plug. It just gives me this really awful sensation in my stomach. I can deal with it better if the inflation isn’t as quick and I’m given some breaks, but my god. And she wasn’t even inflating it that often. I know I have taken far, far more in the past.

After de-inflating it once more, she started inflating it again and as the inflation increased she started biting my butt. It was a wonderfully, agonising sensation and dare I say a welcome distraction from the butt plug! I never used to like being bitten but I love it when Mistress bites me nowadays. It’s literally something that I have come to crave.

When she let out the air and inflated the butt plug a fourth time, she stopped fairly soon with the inflation.

“You can go use the dildo’s now.”

The small dildo

While I am able to use the bigger dildo now, I still insert the middle dildo first so as to open the opening and ease myself into it. Unfortunately, it still hurts to insert the smaller dildo too, but the pain goes once it’s inside. It’s similar with the bigger dildo and maybe the pain of initial insertion will simply never go.

With the tail of the pump attached to the inflatable butt plug between my legs, I sat down on the floor and leaned against the wall. I felt rather self-conscious doing this in front of her, though not to a point that I couldn’t enjoy it (which perhaps was the case when I first had an orgasm in front of her and I felt too nervous about it). Instead, I kind of liked this idea of exposing myself like this in front of her.

I inserted the smallest dildo and moved it in and out for about 20 seconds before removing it.

“If that’s the only show you’re going to give with the other dildo too I will definitely inflate the butt plug some more,” Mistress said.

“No, Mistress, I just use this to open my hole… So I can use the big one…”

She looked at me slightly sceptically, but seemed to accept it for now.

The bigger dildo

I inserted the blue dildo and while it hurt a little bit, it didn’t hurt as much as it usually does when I’m on my own. Of course, I anticipated this might go easier when I’m aroused and when I’m around my Mistress I’m always aroused.

For that reason, I was able to immediately start moving the dildo in and out and it wasn’t hurting.

I asked her if this motion was okay, or if I should speed it up a little. She wanted me to speed it up a little bit and said that I should try and move it in different directions. Right, left and up. Different directions? I didn’t realise there were different directions other than in and out, lol. 

She wanted to know what felt good to me. Moving it upwards didn’t do all that much to be honest. And angling it to the right or left didn’t make a massive difference either. However, I get quite a pleasurable sensation when it goes in deeper and the thrusting motion seems to do it for me.

Adding the wand

She gave me the wand to use on top of the dildo and my feeling of arousal instantly increased. For about a minute or so, I wondered if this meant she wanted me to have an orgasm because if she didn’t I was probably going to struggle. There seems to be something about the dual stimulation of the wand and the dildo that makes an orgasm come on a bit more forcefully if that makes sense.

I eventually just asked her and she said something like, “yeah, why not.”

It felt a little like she wanted to see what it looks like when I’m doing it. I have been sending her all these videos but why watch them when you can see your Slave do it in person for you?

When I was first masturbating with the wand and dildo I kept looking at my vagina, so as to focus. In order to get close to an orgasm, I still need to really focus my mind on it and the best way for me to do that is to stare “into nothing,” which just so happens to be my vagina in this case.

But as some time passed, I started glancing up at her watching me, which made me feel awfully shy but equally more aroused.

Then when I started getting closer to an orgasm, I tried to keep looking at her because watching her watch me and see the joy on her face made me enjoy it so much more.

But then when I got really close to an orgasm I couldn’t help but look away because I needed to focus in order to let it happen.

I made noises that I would have previously been too embarrassed to make and had a pretty good orgasm in front of her. Once it finishes, I removed the wand but still kept moving the dildo in and out. Surprisingly, it didn’t hurt to continue moving it about, which due to the tightening of the muscles is often the case.

Testing other motions

I asked her if she wanted me to continue to which she said yes.

Just a moment later, she came over from the couch and took over. She showed me what it would probably feel like if she were using a strap-on on me, which is a different motion than the in and out one I automatically seem to do. Again, it felt surprisingly pleasurable. She tried out some other motions and I told her what felt nice and what didn’t do too much.

It was nice that she controlled the dildo now. Once again, it felt intimate; perhaps because I don’t allow anyone else to do this and while this used to be such a painful experience for me, it’s now become pleasurable with her. I always tense up as soon as anyone even comes close to my opening but in this case, I could let her move it around however she wanted.

I guess now it’s just a matter of continuing using the dildo every day so that I remain relaxed. I wonder when Mistress will use an actual strap-on on me!

Xx Mila

If you are interested in watching my daily vaginal training videos, they can be found on my Onlyfans.