Wow... where to begin. Let's start with being caged no maybe play time or my new rule. Or I know chocolate cake!!!! I love chocolate cake!!!!!

Sorry if I am kinda distracted thanks to getdare user STIBBONS who found my pm dares I now have my medium butt plug in for the night as well as of course my caged little cock which awaits Miss's teasing.

Anyway so being caged I have now cleared the 63 hrs mark and by morning it will be three full days. Days of no touching and really...

Well, I managed to do it this morning. It takes a pretty good amount of me being stupid for Miss to punish me but today I managed to push her over the edge.

A quick rewind. I removed my chastity cageast night do to some health concerns I had from the way I am built. Needless to say when we chattednin the morning Miss was not pleased but... she was understanding at least. She then told me after my shower to recage my little cook and then I could have some dildo as a treat!
...

And so it begins… I was so excited to chat with Miss that (after first asking if I cod play with my dildo) I asked if Miss wanted me in my new chastity cage. Apparently that was a mistake. I was given permission to play with the dildo but only after I had been put into chastity. Well 1 min of fucking quickly turned my cock rock hard and it struggled to grow against the confines of the cage. It hurt sooo much yet was so frustrating because I could not truly get pleasure from it.

Miss...

So... I think I may have duped myself into a very foolish bargain. I was bored this morning and curious so I asked my Miss a few shall we say personal questions.

She did not want to answer. So I decided to make an offer. Miss twisted my words and she turned it into 2 weeks in my coming chastity cage per question. I think I have bargained it down to 1 week per question which will leave me in chastity for an entire month.

I have begun thinking about it and now i realize I...

Do to some life stuff Miss and I did not get to chat or play last night or in this morning. We did spend the day as usual chatting off and on while at work and with me sending the occasional video or picture when I could get away.

Then the afternoon hit and I found the coolest looking role play dare. Miss Lilly's school. I asked Miss permission to enroll in a class or two if that was ok. After checking it out she said I definitely should take the sissy 101 class and the self-control and...

Well I had a pretty good chunk of time free for play with Miss. I had been nervously waiting and finally it was here!!!!

She started off with being plugged while performing some tasks around the house (weeding the front yard was scary due to the loose sweats and black thong). Then she Jessyfied me... I was to look through my sister's clothes for some shall we say "fun". I stumbled upon some tight fitting legging kind a things that ended up being see through too. Miss LOVED them...

I am so excited!!!!! Yet super nervous and a little scared. I am going to be home alone tomorrow afternoon until the next morning. I have already let Miss know and she said she would have to plan a few things.... when I tried to inquire as to what they were well she just said I would have to wait.

The problem is I am one of those people who likes/needs to know what is going on. Otherwise I run countless scenarios over and over in my mind trying to game plan through every possible thing....