Dick Diary Entry: October 5, 2025

I had a session with my sub that comes to Me every quarter. He saves up a huge chunk of money so we can have a very long cam session. This time he decided he wanted a two hour cam session and 10 tasks leading up to it.

When he booked the session he put himself in chastity. On the day of the session it will be 10 days. I started on Monday by sending him one task a day and then Thursday I sent him the full list that way he had Friday and all day Saturday to complete as many tasks as he could before we had the session, he ended up getting through seven out of 10 tasks. I was very surprised he even got that much done.

his last task before the session was to get fully dressed up in a sissy outfit and do his make up. I wanted him dressed to the nines. he wore a little black dress with fishnet tights and 7 inch pleaser heels.

One of his favorite kinks is anal training, so I knew that we were going to have a ton of anal toys to play with. This sub is a huge toy collector. He loves collecting toys and wanted me to pick out two toys before we had the session so he could get them ordered and sent to his house. I had him go to the lovense website as those are My favorite toys as they are ones I control from my phone. I told him to get the mini fuck machine as well as Solace Pro, the one that jerks him off. Needless to say, he was very excited about these.

We started off the session with him, taking the plug that he has in completely out and starting with his smallest plug. Now the smallest plug for him is going to be a large size for the normal person. He easily took that plug like a champ. I had him put the plug all the way in, sit up and rock his hips so he can feel the full thickness and length of the plug in the walls inside of him. Then I had him take his vibrating wand and sit on that while he was rocking it was driving him absolutely crazy.

From there we moved on to his plug that looks like a bunch of balls each one getting thicker and thicker. I had him put it in and pull it out over each ball, at that point he was ready to be fucked by this machine.

I had him put a pillow underneath him for leverage and lay down with his heels, fishnets and fully dressed up with his wig still on. I started to fuck him slowly mind you he is still in chastity at this time.

At the beginning of the session, we talked about him coming twice, but first I wanted to get his ass in gear. I slowly started fucking him with the machine, going faster and faster watching his body go absolutely crazy. He could barely hold on his, cage was getting tighter and tighter and he was begging to come at this point.

I told him to get his vibrating wand, put it on his dick while I him fuck him. I told him if he really wanted to come, he would of course have to eat as he couldn't let any of it go to waste.

he was begging to let go, and I counted him down to come. It was a huge load to say the least and of course he ate every last drop. I told him to go collect himself and drink some water, get hydrated and get ready for the next round. He let me know that his ass is very sore and he doesn't know if he can handle anymore but he could definitely come again because we did still have the other toy he wanted to play with.

I told him to keep the chastity cage on for now and put the spread bar on and do some sissy poses. I told him to reach down, grab his ankles and walk around. I remembered he had nipple clamps, so I told him to put them both on and put the chain in his mouth while he walked around the room. It was absolutely hilarious watching him walk around like the hunchback with the spread bar in between his legs and him trying to keep his head down, so the chains wouldn't pull his nipple clamps.

After he took off the bar and then nipple clams I told him to put on his full mask that has sensory deprivation (Vision) as well as a gag in it, take the vibrating dildo and put it on his dick as I allowed him to come out of his cage. watching him get so sensitive I couldn't help but laugh as he was convulsing laying there.

I had him take off the mask and get the final toy that I controlled to jerk him off. I had him put it on, and I stroked him hard fast and long until he begged every last moment to come. The toy ended up slipping off and he couldn't help but beg to jerk until he came and I allowed it.

He came so hard that he could barely move, Exactly how I told him I was going to leave him… fucked in every way, Stretched and tired as fuck. Needless to say he will be looking forward to his next quarterly visit.