Dick Diary Entry: January 31, 2026

My sub got a new toy for his wife, but before he gave it to her, he needed to try it out. It was a little vibrator with a clit stimulator and a whole bunch of fancy settings. The session topic for tonight was how he could be the best sissy. We ended up doing a 15-minute cam session.

At the beginning of the session, I instructed him to do a few sissy poses. "Bend over, open your ass, wiggle it," I commanded. I instructed him to rub the vibrator along his clit dick. When I saw that this wasn't doing it for him, I told him to start on his ass. I instructed him not to insert it but to put the vibrator on the lowest setting and rub it against his asshole.

This is where I started my story. I painted a beautiful picture of how I would get him dressed up in a blonde wig, a tight purple dress, and some heels. I envisioned walking him around the bar. I won’t go into too much detail, as it gives away my storyline. From there, we ended up in a room. I told him I was going to pimp him out. The walk around the bar was just to showcase the goods that people were going to use.

The first man walked in, took out his cock, and got him hard. He ended up coming in my sub's ass. The second man walked in and started to use his mouth until he moved to his ass. This is when the third man walked in. Now, he was being spit-roasted. Both men came in their respective holes and left.

Last but certainly not least, Daddy came in with his big, thick black cock. He started to use my sub's sissy mouth to get him hard before moving onto his ass. This is where I began painting vivid imagery. I described in detail how he was being used by this big, thick cock. His body started to convulse as his ass was being fucked harder and faster with his toy. I could see his body clearly shaking.

As I continued to get more detailed about how he was being fucked, I could tell he was on the brink of coming. I kept painting the imagery of how he was about to experience his first sissygasim. If you don't know what a sissygasim is, it's when a sub comes strictly from anal stimulation. I knew I had him right where I wanted him. I maintained all the detail, watching him convulse, shake, and truly enjoy himself.

I whispered softly into the camera, "When you feel it, just let go." Next thing I knew, there was a big pool of cum that landed on his stomach. At that moment, I knew he had achieved it. He couldn't stop thanking me for finally giving him the freedom to be who he truly is. This solidified for him that this was what he truly needed to be in life: a big sissy.

Never underestimate the power of mental domination. Without me painting the picture for him and him being very open-minded, he would have never achieved this. Mental domination plays a huge role in any type of domination, regardless of whatever kink or fetish it is. There is always some mental play involved.

Stay kinky and open minded.