First conversation with a sissy a couple nights ago online

DoItAgain1144

Virgin
Joined
Jun 19, 2025
Posts
4
Basically title. I found them via Reddit. We chatted. Exchanged some pictures. We sent a couple videos and talked fantasies. We were both new to this. She wanted guidance and someone to push her, guide her. We set ground rules. We chatted some more.

I started with some simple stuff. She said she had only ever worn panties in public. I told her to wear her cage to run her errands that day. She was a good listener.

And at night we chatted together. I told her what to wear. She dressed up in her cage, wearing what I asked, and she watched a video (FPOV blowjob video) that I sent to her while I made her use a vibrator on her clitty. We chatted through it. We came together even though it was all through chat. Shared pictures the whole way through.

And then I went to message her today, and her account was deleted.

And I'm sad.

It took a lot for me to be able to get over the barrier of messaging someone. I've only ever really hooked up with women. I've been pretty dominant in them all. I had plans. I get emotionally involved in these dynamics. It takes a lot of vulnerability for me to show up as a dominant. I'm really cautious about this stuff, which is why after 25 years of looking at gay/sissy/trans pornography I finally decided I wanted to contact someone.

And one night was great. Even though we never spoke in real time, it was only just messages. And even though you'll never see this: Olivia, that was great. Thank you. If I pushed too hard, I'm sorry. If you got scared, I understand.
 
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