Did I just initiate penetration…?

I think I maybe did. Mistress and I were out late last night and this morning we were both in bed still around 8:30 (which is pretty unusual for us). Mistress got up to pee and as I lay in bed with my cock feeling VERY hard I imagined her calling me… ‘Slave, come here and lick me clean’.

That’s probably never going to happen of course, but for some reason the thought popped into my head and made my cock throb even harder. When she came back to bed the sight of her gorgeous naked body only made it worse and soon she was stroking my cock and teasing me while I played with her beautiful breasts.

Well things progressed and Mistress threw her leg over me and started rubbing my cock against her pussy, but at this stage I still felt this was just to tease me. However, it wasn’t long before I had my fingers inside her and then she pulled me on top of her and inside her.

It felt so good watching Mistress laying squeezing her gorgeous tits as I slid in and out of her. I lifted her legs up and started kissing her feet as I fucked her, but all too soon I could feel myself getting a bit close for comfort.

I tried to push it back but it was not having it, and I warned Mistress that I was getting close, unsure of how she would respond. She asked me if I wanted to be allowed to cum inside her, and while I guess the answer should have been ‘whatever pleases you Mistress’, this time it all felt a bit different… I felt like I had initiated this so I wasn’t sure what I was ‘supposed’ to do next.

I told her that I did want to and Mistress told me to cum inside her. I was already close and the second I started to fuck her harder I could feel my cum spurting inside her. Even when I was done Mistress’s pussy was still squeezing my cock and even though it felt wonderful to cum inside her I did feel a slight a pang of regret that it had been over so quickly.

We were debating whether to have our Femdom session tomorrow, but that’s kind of off the table now, I can’t imagine doing a session having cum the day before, we’ve never done that… and it would be weird not feeling at least a little desperate to cum.

Mistress obviously enjoyed our fun this morning, and she’s not really one to hold me to any ‘rules’, even rules that she made and we’ve stuck by for nearly five years. I guess she could easily have stopped me at any point (and she has before), and she obviously wanted me inside her, but I still can’t help but feel that I pushed it from a simple teasing to full sex.

I guess when we do have our Femdom session, Mistress has something concrete to punish me for if she chooses to do so, and that makes four orgasms for me this month, which is the most I’ve had since April 2011 (our very first month of full time chastity).

I wonder where things will progress now, it feels like we’ve deviated from our chosen path, although that’s not strictly true as ‘the path’ was always that Mistress could give me as many orgasms as she wanted… it’s just that up until now she’s tended to keep it to one or two a month.

Obviously I’m not upset about it or anything, I wanted Mistress to control my orgasms and I’m happy for here to allow me as many as she wants. If she wanted to make me cum ten times in a month, or not at all, as long as she decides what she wants then I’m happy.

EDIT: It’s at times like these that I kind of wonder if blogging is a good thing, because when I read this it could easily be misinterpreted. But when I blog on here I can’t help but filter my thoughts through the ‘chastity’femdom’ mindset, I hope Mistress R understands that when (if) she reads it.

EDIT 2: Actually, having thought about this some more, maybe Mistress wanted my cock inside her all along, maybe rubbing my cock against her pussy was her giving me the green light and what I took to be me initiating penetration was nothing of the sort???

4 thoughts on “Did I just initiate penetration…?

  1. The fact you subby men can’t ever stop hemming and hawing over whether you should cum or stay denied is exactly why you need have your cocks and orgasms under control of a strong woman. Just because one month out of like 50 you have cum more often doesn’t really mean anything other than MR obviously felt like it and beyond that you should just feel lucky! You never know when the mood may strike and she makes you go longer than ever before too!

  2. Hi Mistress Marie…
    Third reply…. first one disappeared, second one my thumb caught the mouse mat and deleted in a mili-second! Aaaaaaaaargh.
    You are right of course…. and I hate how negative this post comes across, which is why I commented about how I’m not sure blogging is always positive, because I’m almost hoping Mistress doesn’t read this now because it really comes across like I’m taking something really awesome and moaning about it, which is not my intention at all.
    I’m just a little confused now because I’ve had this rule for 5 years and now I feel like I’ve broken it and that leaves me feeling like I don’t know where I stand…
    I’m not saying Mistress ‘should’ have stopped me, if she wanted me inside her then why should she?
    I guess in my vivid imagination what she ‘should’ have done was when I was licking her pussy clean afterwards she ‘should’ have told me how lucky I was to be allowed inside her and how she hoped I enjoyed it because I was surely going to pay for it later…

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