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This past weekend, with Angel and I both feeling particularly horny, we found some time to make sure that HERS was taken care of despite the fact that I would still not be unlocked for my own! Keeping in mind that the last time we had much playtime was following a big fight between us, it was very nice to both be going into this completely relaxed and on good terms with each other!

Angel told me that I was free to do ANYTHING I wanted to her that evening–though of course I was immediately shot down when I said that I wanted to be inside her! 🙂 THAT wasn’t happening. Instead, I started off with the usual routine of getting her warmed up with some orgasms via my fingers, tongue, and of course her magic wand! As things began to heat up a lot, Angel requested that I pay some attention to her ass, as it had been quite a while since we had done anything like that!

To backtrack just a bit, before we went on our little anniversary get-away last month, we had begun playing around with several different sized butt plugs, etc. and found that Angel was really enjoying them! She really wanted to try straight-up anal with ME inside her, but of course that could only be done when I was not locked! Well, when I was out of the Queen’s Keep that weekend, we did in fact try that for the first time ever!  I just didn’t write about that aspect of our adventures before, because it didn’t exactly work out quite the way either of us was expecting..

Being unlocked after several weeks in the Keep, I did have some amazing, very intense orgams for myself rather quickly that weekend! Maybe too quickly, because I believe that at least a small part of the problem we had with our anal attempt, was that we were trying to do it while I was still somewhat drained and was having a little bit of an issue getting hard enough again to give it a go! The very first attempt proved futile, so we gave it up until the next day when we could try again.  Even then though, something just didn’t feel quite right. It was almost like we were just going straight for the “prize,” rather than having all of the build-up to it that we normally enjoy when I’m locked! I did eventually get both her and myself lubed up sufficiently and slowly slid myself in. Tight? Yes! Amazing feeling? Of course! But so is regular sex! 🙂 To be completely honest, I personally couldn’t really tell enough of a difference for it to matter one way or the other which hole we were using.. Then, Angel started saying that it was really kind of hurting her, too.  So we stopped.  No big deal, not near the end of the world or anything, it just wasn’t working the way we had thought it might! We just cleaned up and continued having our “normal” fun! We tried one other time later that weekend with the same result, and have steered clear of any more ass play since then… until now!

I didn’t want to go too big too fast, so I grabbed the medium sized butt plug that I know Angel has been able to take well.  A little bit of lube later, and it slipped right in and filled her up nicely! As she was thoroughly enjoying the sensations, I had her turn back over onto her back so I could keep using the magic wand on her as well.  I then confirmed with her that she did previously make the statement about me being free to do ANYTHING to her, and declared that I WOULD be inside her, one way or another! 🙂 I grabbed our cuffs from beside the bed and she made no attempt at all to stop me from tying down both of her hands.  I also slipped a blindfold over her eyes to at least keep her guessing a little bit!

At that point, I had her squeeze her legs together to hold the magic wand in place for a while, so I could take a little time to slip on a strap-on harness over my chastity device.  That’s also something we haven’t played with for quite some time! Once everything was situated I climbed back on top of Angel again, moved the wand out of the way, and proceeded to use the strap-on on her. Being able to watch and feel her body move underneath me as she was being penetrated from BOTH ends was absolutely amazing! The only thing that could make it better would be if I were actually inside her myself, but I also know that then it would have been over and done with much quicker! This way, it truly felt like I WAS inside her, but could keep going, and going, and going…

A few orgasms (for her) later we took a short break, after which Angel asked if I could try the strap-on in her ass! I was a little bit worried about doing that, just from our last experiences, and the fact that this dildo is at least as big (if not a little larger) than me! But, Angel really wanted to see if she could handle it, so we removed her butt plug, added more lube, and gave it a go!  I very carefully and slowly began sliding it in, and was surprised that before either of us knew it, the entire length was in!  At that point I just completely stopped to let her get used to the feeling, but she didn’t need very long! I started thrusting it in and out, slowly at first, asking for confirmation several times that I was not hurting her! She insisted that I wasn’t, and the more her body started responding the harder I started thrusting it!

Angel was clearly in heaven right then, and with the additional help of the magic wand that she was still holding for herself, it was impossible to count how many more orgasms she had in that position! As things started winding down all she could say was how amazing that was, and she did feel a little bad that I couldn’t feel it too! I assured her that I DID feel it, and it was quite a ride making sure that I kept pace with her body as it was moving around all over the place!

As much fun as we had started having while experimenting with anal play before our trip last month, I was very glad to see that one bad experience didn’t just completely turn Angel away from it! She was willing to try it again, and judging from the outcome of THIS weekend I have a feeling that there will be much more of it going forward! That strap-on may even start to get a lot more use, the longer I am locked in the Queen’s Keep!

It’s been a little while since I’ve made this comment, but I am SUCH a lucky man! 🙂

Comments
  1. vinnieh says:

    Sounds like the two of you enjoyed this session. I was turned on reading it.

    Like

  2. pantiewearer says:

    This is the second story I’ve read by you. You are a very erotic story teller and I enjoy your stories immensely I plan on reading this story to my wife and see what her reaction is. I have had the luxury of massaging her anal and licking it also. However penetration has not occurred yet accept what little my tongue can get in

    Like

  3. deepexplorations says:

    Awesome post, and it sounds like an even better experience! Good for you, and thanks for sharing!

    Like

  4. bshowers90 says:

    Very good read this morning! I’m so glad yall were able to make it work, anal orgasms are the best!

    Like

  5. agatagrop says:

    Hahah, nice! I’d like to try this with my boyfriend too. At the moment he is not locked anymore because I had to move to an other city… A long story, but maybe this weekend I could make him wear the cbt and the strap-on at the same time

    Like

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