Dick Diary Entry: January 15, 2026

I have a very well respectful sub that has been messaging Me probably for about two weeks at this point. They paid ahead for a session when We first started talking. The session was scheduled for one week later. After we talked throughout the week, they decided that 10 minutes was not going to be enough so they wanted to extend to 20 minutes and sent again.

This morning we started talking getting ready for our session later on in the evening, they wanted the session recorded. I let them know that there was an additional fee they sent for it.

We got prepped and ready for the session when it came time to have some fun. I made sure everything was good to go in terms of recording it, and We went over their kinks and fetishes.The session started, they were dressed in the cutest little maid costume with some fishnet tights, an anal plug and they were wearing a flat chastity cage. Now the sub has never came in their chastity cage. I saw this as a challenge.

They had an assortment of plugs, a vibrator and two dildos, one smaller pink one and one very large black one. Kind of laughed and asked them if they bought the pink one first realized how small it was and then really overcompensated with the black one. they smiled and said yes that's exactly it. I started out the session having them model for Me do some sissy poses the normal fun stuff.

After while I had them pull out the medium plug and put in the large plug. I instructed them to sit down flat on the bed, rocking their hips to feel that sensation deep inside of them. Then put the vibrator on the plug and continue to rock their hips. This is something that they have never felt before and they were leaking everywhere through the flat chastity cage.

After I was done with that plug, I told my little sissy bitch that I wanted them to start with the dildo the small pink one. Their ass was so hungry, the little dildo went in so quickly. After ensuring that they were good and ready, it was time to bring out the big guns.

they prepped the black dildo, getting it nice and lubed up, bent over the bed ass facing Me on camera and slowly started to insert this big 12 inch black dick. Through their moans I could see their ass completely swallowing it. The moaning got louder and louder as they were getting fucked. I told them it was time to grab the vibrator.

I command they put it on the lowest setting and put it right on their cage. As the moaning increased, We ended up going overtime in our session, but I wasn't done yet. I wanted them to reach the finish line.

They started grinding the vibrator moaning louder and louder fucking, their ass with the dildo slower and then faster. As I'm telling them how I would peg them and make them My sissy little whore I can see their ass start to go up higher as they are pushing the vibrator on. I asked them are you ready to release for Me? My little sissy moans out along yessss.

Next thing I know it's happening! I start seeing them dribble out of their cage and their body convulsing, shaking twitching, you can tell that they really enjoyed it.

I told them it's time to get cleaned up and they thank Me for the session. After they are cleaned up they message Me and told Me that that is the absolute best orgasm that they have ever had, and they never thought that they would actually be able to come inside of such a flat cage.

This just proves that you can never never underestimate Me.