Half way through Locktober, I WAS let out of the Jailbird twice, for a full blown orgasm each time. So I won’t be able to say that I was locked completely 24/7 for the entire month, but each time out was so short (maybe about 30 minutes TOTAL) that I’ll just add a note and not even reset the counter on my Current Status page.

Angel does like the idea of Locktober, but it just so happens that our anniversary falls during the same month. And as previously written, I surprised her with a trip to a place with a private pool inside our suite! (re-read that story here in case you missed it!) I had joked with Angel before we left, that this surprise was probably going to have her so turned on that it was going to be a “panty-dropping moment” as soon as she saw what it was! Her response was “Oh, we’re going to Hugh Jackman’s house?!” Dammit.. Guess I’ll have to settle for SECOND best panty-dropping surprise for her! Lol

But nonetheless, we obviously had LOTS of sexy time together last weekend, of which there will be many more details written here in future posts! I was locked for the vast majority of time, but Angel made comments on several occasions that before we left she wanted to have me out and actually have REAL sex in the pool for a change! I blew that off and kept redirecting her attention (with more orgasms, of course) as long as I could, but after all she IS the one ultimately in control of whether or not I am allowed out of chastity!

Here’s the thing. As amazing as I knew it would be, I didn’t necessarily think that I DESERVED to be out. During my three months of freedom this summer, I realize that I may have been a bit “bad” as written on my post “Confessions of the UN-Chaste.” I promised myself that this weekend at Sybaris, if/when Angel tried to let me out, I was going to come clean to her about all of it and let her decide if she still wanted to do it or not. However, Sunday evening as we were swimming together, Angel came over to me and slipped the key into my hands making VERY clear what she wanted! I couldn’t possibly ruin that moment, so I held my tongue and did not make good on my promise to myself.

Don’t get me wrong, it felt absolutely AMAZING to be inside Angel in that environment! It seemed like somehow the water was making me last a bit longer too, as I was able to keep thrusting harder and deeper until Angel had a full TWO orgasms that session before I really felt myself losing control! All in all I wasn’t out for very long at all before locking back up and handing her the key on the way to shower and head out for some dinner that night.

The next morning, Monday, we were down to the last several hours of our very peaceful (and kinky!) vacation. Angel started telling me that she kind of wanted me once more, but that I would have get out of the pool and go back to the bedroom to retrieve the key that time. She told me where it was and I did find it right away, but came back asking if she had brought both of the keys with her or just the one. She told me where the second one was in the suitcase, seeming puzzled thinking that maybe the first wasn’t in the place where she had thought it was.. Acquiring the second key as well, I finally put my big reveal plan into action. Of all the fun, sexy things that I had planned for the weekend (and even already implemented most of!), I kind of dreaded this particular moment, not fully knowing how Angel might react.

In the past we have played with online services like EmlaLock, uploading a picture of the combination to a realtor’s lockbox, and not being able to gain access to it until a designated time has passed. Quite some time ago, I went ahead and set the lock to some random combination, and had a picture of it in a safe location on my computer that I wouldn’t look at. Over time I’ve COMPLETELY forgotten what that combo is, as it is no number that I ever use for anything! When I locked myself up at the beginning of Locktober, I went ahead and started an EmlaLock sesssion at the same time, uploaded that file, then permanently deleted the picture from the computer. I’ve left the lockbox open since then, but as soon as it gets slammed shut there will be no opening it until we get the code back!

So I went back to the pool to find Angel, carrying the open lockbox with both keys to my Jailbird inside. Getting back into the water, I got down as far below my Mistress as I could, and began my speech. I told her that I didn’t necessarily feel that I deserved to be let out, and that if she agreed with that by the time I was finished talking then she had every right to just slam the door of the lockbox and the keys would be very securely out of reach for a considerable amount of time! I went on to say that there was probably a reason behind her observations that I tended to be far less horny when unlocked, and that it was because of a fair amount of “self-indulgence” that I tended to get caught up in sometimes. Angel didn’t react much, but I couldn’t help notice her pursing her lips together a few times while I spoke.

After a few questions from her along the when/where/why/how variety, it was the moment of truth. Angel reached over to the lockbox and… pulled out one of the keys for me to go ahead and unlock myself again anyway!!

“Are you sure?” I asked

“Oh, you ARE GOING to be locked again!” Angel replied. “But it’s not always about you.. This is for ME!”

The tone in her voice at that moment was unlike ANYTHING I’d ever heard from her. Different than she’s ever spoken to me, the kids, or anybody! It was strict, demanding… extremely self-confident! If we weren’t standing in 5 feet of water at the time I think I would have immediately melted at her feet to the sound of her words.

The cage had gotten so tight at that point that it was a bit difficult to remove, but we managed. As Angel took me deep inside of her for the second time in as many days, I said “Thank you, Mistress. I know that I don’t deserve this in the least!” After a little while, Angel decided to switch tactics a bit since she also wanted to feel what it was like to have “real sex” on the swing that we had brought too! (Yes, a swing. Stay tuned for a future post for more on that!) So we exited the pool, dried off and Angel leaned back into the swing and let her body sway back and forth as I took her for the last time of this year for sure, and it will be well into 2019 before the opportunity may ever present itself again. Luckily I did manage to hold out long enough for Angel to get another orgasm out of it, but watching her lose control of herself as the new sensations wash over her… Wow, that still just totally does it for me EVERY time!!

When we were finished, Angel left me to clean up and lock up. I took the lockbox back into the bedroom and placed it next to Angel. She asked how long we would be without the keys if we did this, and after I told her she proceeded to push the door of the lockbox closed, sealing my fate.

Angel continues to give me a little bit of grief from time to time, embelleshing on the fact that she’s still getting all of the orgasms now as “payback” for all of the ones that I had without her before.. But she has also told me that she wasn’t REALLY that pissed about it. Actually thought it was kind of hot that I did that while thinking about her!

So how long WILL I be locked up this time with absolutely no means of release? Well, the EmlaLock session was set to randomize the duration, with the earliest that I’d be unlocked being Valentine’s Day and the latest my Birthday in mid-June. So effectively 4-8 months from now! That’s a pretty wide range, and I have a feeling that we will definitely hit a chastity record for us during this time!