Kinky Key-holding

Posted: August 3, 2015 in Anal Sex, Chastity, Key-Holder, Male Chastity, Orgasm, Orgasm Denial, Sex

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Lately, Angel has been finding a kinky streak within herself that a year ago she probably would never have even thought existed! Maybe that comes partly from keeping her husband (Me!) locked in chastity for longer and longer periods at a time.  Maybe it comes from getting VERY friendly with her magic wand, and therefore getting much more in tune with her body as far as what turns her on and makes her orgams the best they can be.  Maybe it’s a combination of both or something else altogether; but whatever the underlying reason, I’m certainly not complaining about it! Lol

Case in point about Angel opening up much more to trying new things, is with Anal Sex.  I have always had quite a bit of interest in this myself and have even done a fair amount of experimenting with a few different plugs, etc. on  myself. Angel, on the other hand, has always been pretty adamantly opposed to anything back-door related, either giving or receiving. I think she had at least one bad experience with it with an ex or something.. And that is totally fine, as we still come up with plenty of other ways to keep each other happy!  Recently though, Angel has made almost a complete 180 degree turn on that stance! It started a couple weeks ago right before our vacation, and after some of the stuff I wrote about in my “Wand Magic” post. It seems that the wand has become even MORE magical! 🙂

We were having another little session of seeing how long Angel could tolerate having the wand turned on down there completely non-stop and unable to get away from it at all.  For the record, she’s up to about 24 minutes of it now! During this period, she did change positions numerous times, having countless orgasms in each position. At one point she got up on her knees so I was behind her almost doggy-style, but all I was doing was still just holding the wand in place.  Obviously this gives me a perfect view and access to her ass! A couple of orgasms in, I started kissing around her ass, then started a soft massage around the hole with my thumb.  The way her body lurched, I think she even surprised herself by how good that felt and added a lot to the next orgasm to come her way! Talking about the experience later, Angel had even thought at the time that I had actually stuck a finger or two all the way in, so she was even more surprised to learn that it was all from the outside only.  At this point, for the first time in all the years that we’ve been together, Angel actually told me that she wants me to have “all of her,” including her ass.  She just wasn’t sure how I could ever “fit” in there and is a little bit afraid that it will hurt..

First of all, to tease a guy who’s locked in chastity, about being out and having his wife’s ass… Wow, talk about making the cage that much tighter!  Angel knows me well, that I would love to do this some day, but I do also completely understand her hesitation with it.  I assured her that if she really wants to go forward with trying something like that, we would go VERY slow with it, and if anything hurts at all she can tell me and we’ll stop right away and figure it out.  I suggested we start with a skinny, beginner’s butt plug with a ton of lube, and just go from there.  That was it for the conversation at the time, since we were getting ready to go on vacation, but she did mention to me more than once on the trip that she was very intrigued and getting excited about trying some “ass-play!”

Fast forward a couple of weeks.. Vacation is over, and one day after work I made a little detour on the way home to stop by the local adult shop to look at some butt plugs for Angel.  Thinking ahead a little bit to the future (assuming she likes it!) I selected a whole set with three different sized plugs. They are bright pink, silicon, and pliable enough that they should fit pretty nicely inside her. The smallest is only about 3/4″ thick and not more than about 3 inches long. The medium plug has the same diameter but is an inch or so longer, and the large plug looks significantly bigger, both in diameter and length.  It will certainly take some time to work up to that one!

I hid the package next to my side of the bed, to wait for the right time to show it to Angel.  I didn’t have very long to wait! One night over this past weekend we were playing with the wand again and Angel reminded me that the kids will be staying with their grandpa this coming Wednesday night, meaning we will have the house to ourselves.  She suggested we might want to think about “picking something up” for that night, so that’s when I told her I already had! I had Angel take over with holding the wand on herself while I got them out and showed her what we had.  Starting with the small “cute little plug” that we could start with on Wednesday, and I told her that I thought IF she ever works all the way up to the large one, if she can handle that one comfortably then I would bet she’d have no problem handling me, either!

Now that she knew we already had a plug, the idea to wait until Wednesday to use it went right out the window as she wanted to try it THEN! Of course I was happy to oblige, so back into the doggy position she went, STILL holding the magic wand in place! I grabbed the lube, putting an ample amount both on her hole as well as the plug itself, and very slowly started working it inside.  I talked her through it the entire time, getting her to take some deep breaths and fully relax, and asking regularly if she was OK or if it was hurting at all.  It was pretty obvious when the plug hit home and slipped all the way in, as Angel once again lurched forward on the bed with her whole body convulsing almost like a seizure, only it was just one massive orgasm! With her face buried in a pillow, I almost couldn’t tell if she was laughing or crying! Asking her about it later, she thought it must have been some of both, as she couldn’t even really describe the feeling other than being one of the most intense things she had ever experienced!

I know this is getting a little long-winded so I’ll just re-iterate how much our relationship has been evolving, getting better and better each day, ever since I first locked myself into chastity then gave Angel control of the keys! I’m sure this Anal subject will have many more chapters to write about, and it’s hard to say what other kinds of “kinky things” we may eventually find ourselves involved in.  I am such a lucky man!  🙂

Comments
  1. I can only hope that I am able to get to this point with my wife. (Jealous)

    Like

  2. miss agatha armstrong says:

    So exciting

    Like

  3. bshowers90 says:

    Congratulations! This is a huge step for both of you! Anal orgasms are one of the most intense I have experienced! I wish you both great luck and fun with your anal adventures! I can’t wait to read more updates!

    Liked by 1 person

  4. deepexplorations says:

    Good for you both! And thanks for the hot description! That made my day. I’m guessing that the chastity thing, and the magic wand thing have just got her thinking about sex a lot, and orgasms don’t hurt…that’s awesome. On the anal sex front: as a veteran of giving and getting, you’re doing the right thing. I have no idea how big your cock is, but unless it’s enormous it shouldn’t require THAT much stretching with plugs before you get there. Of course the anal foreplay is a big part of the fun, so by all means enjoy. The more turned on she is though the easier it will be to get there. Just take your time and be gentle and the reward will be worth the wait for both of you!

    Liked by 1 person

    • pcguy0681 says:

      Thank you for the input! No, I wouldn’t consider myself to be particularly “enormous” at all, so I really don’t think it’ll be too much of an issue once we get to that point. I suppose eventually, this might be an extra treat from her when she has me unlocked, to find out! 🙂

      Liked by 1 person

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