My First Locktober Diary
While I’m not a stranger to sissy chastity and wearing chastity cages, I’ve only self-locked before and have longed to give control of my sissy clitty over to a partner. This year, I brought up the idea of trying Locktober to my mistress, Goddess Lola Loveblood, and she was thrilled and came up with a full calendar for me!
I will do my best to keep track of my tasks and how each day is going!
Day 1
Tasks
- Take three photos of myself wearing the cage
- Unlock to masturbate on video for 45 seconds five times throughout the day. Lock back up immediately afterward.
I anxiously awaited this day and was excited to lock up in the morning. I’ve been locked up for full days before, so this wasn’t a stretch for me yet, but I’m sure it will be. Goddess had made me cum before the month started, so I was starting fresh. I wasn’t close to cumming after 45 seconds, but it was hard to stop just as I was getting going. I made sure to rub my clitty to sissy porn.
I met my Goddess later in the day in public, and it was really hot when she grabbed me to feel for my cage and played with the black g-string I was wearing. She reached back to pull it up as far as it could between my ass just as two men were about to walk by us. And I loved that she posted a day 1 photo of my caged clitty online. So excited for this month!
Day 2
Tasks
- Take three photos of myself wearing the cage
- Masturbate for 90 seconds without cumming while wearing a butt plug, and record it. Put the cage back on immediately.
Today was more manageable than Day 1 without having to edge repeatedly throughout the day. We ended up doing a virtual session for the second part of my task.
Although I didn’t need to, I decided to do minimal makeup, put on a pink wig, and a vinyl pink bodysuit with pink stripper heels. While I didn’t go quite as hard as I usually do, I still thought I looked hot.
With a pink jewel metal plug in me, Goddess Lola had me edge repeatedly while sucking on a dildo, repeatedly having me choke on it.
And when she was done playing with me, she hung up.
Day 3
Tasks
- Take the cage off to edge three times for two minutes while wearing a butt plug. Do not cum. Put the cage back on afterward.
- Write a 1000-word minimum story about being a submissive slut
After doing a lot of edging and dildo-sucking the night before, I wasn’t feeling in a slutty sissy mood. The great part about Locktober, though, is being “forced” to stay in this headspace and pushing yourself, so even if I wasn’t immediately thrilled, I locked my cage back on (I’m not sleeping with it on, but I plan to try to).
Having to jerk my clitty for quite some time while wearing a plug without cumming was easy for the first two times since I wasn’t super in the mood, but the last time I went for it and tried to get as close as possible. I barely made it. I was so stiff and ready to pop that I narrowly made the two-minute mark without stopping.
I may post the story I wrote. It’s a bit longer, but I had much fun writing it. It was about being a slave to Goddess and watching her get fucked by her bull’s huge cock.
Day 4
Tasks
- Take a video reading the submissive story I wrote yesterday while riding a dildo with the cage on
- Pick out lingerie to wear to bed. Send videos for approval.
Since it was Friday, I decided to get dolled up: I did my makeup, put on a blonde wig, purple strappy lingerie set, and black stripper heels while working up to a medium-sized buttplug, which wasn’t too hard since my sissy pussy had been warmed up the last couple days by wearing small buttplugs off and on.
I gently worked myself down on one of my medium-sized but long dildos and started to grind myself back and forth while I read my submissive cock story from Day 3. It felt so hot and went on for almost 15 minutes. Hopefully, later on in the month, I’ll be able to have a sissygasm this way.
Finally, I sent Goddess a couple of videos before being sent to bed in a flowy black bra and panties set.
Day 5
Tasks
- As soon as you wake up, take a 30-second video of yourself in the lingerie you slept in and send it. Beg for cock throughout the video.
- Write a letter with a minimum of 400 words begging me to fuck you
My Goddess often enjoys sending me to bed in lingerie. The best part of this is you wake up immediately as a sissy slut and know your place. While sleepy and ragged, I got myself up and recorded a quick video about wanting cock.
The day was pretty chill, and I lounged around in a red bralette and matching g-string. I went for a long walk fully caged when I got a text message from Goddess asking me to show that I was still wearing it. I was out in public but found a secluded corner to snap a pic of my pink cage.
After I wrote a letter begging for cock, Goddess had me present lingerie options for bed and wanted videos of me spreading my sissy pussy and sucking on a dildo! A fun way to end Day 5!
