You Win Some, You Lose Some...

Tonight was a definite up and down affair, on the upside Mistress had another epic orgasm with my finger just tickling her asshole until she started to cum. It was amazing and wonderful and I felt so happy to feel her cum so incredibly hard…

Again, afterwards I felt so ridiculously hot, I don’t know what the fuck is the matter with me, I’ve been like this for ages now. It really isn’t that hot and yet I seem to get so overheated so easily. I have had a cold these last two weeks but even so…

I probably should have asked Mistress to tease me another day, because I should have known it probably wouldn’t go so well, but then I’ve been so hard lately that I’ve come to expect it now, so I thought it would probably be fine.

Sadly that wasn’t the case tonight, despite Mistress’s best efforts. She lay down beside me and started touching her pussy, she told me she wanted me inside her and that I should stroke my cock and get it hard for her. If I’d have been thinking straight I should right then have asked if I could put the cock ring on, but I wasn’t thinking straight of course, I got up on my knees so I could get a better look at what Mistress was doing and it was awesome to see her lying there touching herself, I loved every second of it and she looked absolutely stunning.

But my cock was just not playing, it got sort of 80% there, but not hard enough. Mistress took over and it seemed to pick up a bit but then it started to flag as I seemed to get hotter and hotter… eventually I suggested putting on the cock ring but we both knew the moment had passed.

It’s kind of hard to take when it’s so long (actually it’s only been seven weeks) since Mistress has wanted me on top and inside her, and the worst thing is that I know this is going to play on my mind now and it will probably mean using the cock ring again until I can build up my confidence again.

It always seems like these things happen at the most inopportune times, I’m sure if Mistress ever decided to let me take her ass the same thing would probably happen. I just hate the fact that Mistress was being so engaging and it didn’t work out, I really don’t want her to think that I wasn’t into what she was doing because I really, really was…!

I guess I should look on the bright side and think about how hard Mistress came, it really was absolutely wonderful to feel her cum so hard, and you know, I wasn’t going to use that little trick again tonight… but I’m glad I did.  After all, her pleasure is the most important thing to me (IT REALLY 100% IS) and she was super happy with me there. 

And you know, I’ve been here before, I’ll no doubt be here again, and it will be okay. But it’s hard when it’s not hard enough, if you see what I mean…

Amazingly, Mistress is up to ten orgasms this month already… which is more than she’s had most months in the last year. I really hope we can continue this on for the rest of the month and at least get her up to 13 or 14.