Introductions discussion

I go by Jenna. Or at least, that’s what people call me online; it’s actually the name I use for my sissy alter-ego. I’m a closeted gay crossdresser, so neither my friends nor family know much about my real interests: penile chastity and passive anal sex with men.

I stumbled upon chastity over five years ago via an erotic story, and it’s been exciting me ever since. The first device I tried was the Curve; while it helped me understand myself and my true desires better, it ended up being too big, a bit unsafe, and quite fragile. Still, it served its purpose. I learned that anal masturbation works well for me, and passive sex with men feels much more satisfying than active sex with women. Even though I’m deeply submissive in the bedroom, chastity has never felt like “punishment” or something negative to me—maybe a touch of humiliation here and there, but nothing major. Honestly, I don’t mind suffering; life’s too short for that.

Right now, I’m wearing a custom-made Steelheart 2, though I keep a CB6000 handy for trips. My personal best is 128 days in chastity. However, my big dream is to fully commit to receiving anal sex as my main source of sexual relief. So yes, like many others here, I have fantasies about permanent chastity. I’m currently hunting for a boyfriend or keyholder to help me explore these possibilities…

Hello Jenna! It’s fascinating how often people mention their first device didn’t work out. That happened to my first three too!:D I sometimes wonder about the ratio of those who try just once versus those who go through several before finding the right fit. When it comes to family and friends, I was on Skype with my brother yesterday. He asked what his sister-in-law and I were planning for the weekend. For a moment, I thought, "Well Bro, later we’ll lock up after taking out my chastity device all day, and then I’m going to put on a dress!" But naturally, I didn’t actually say that. Welcome to our community. I enjoy it here and hope you do too. You should definitely keep a journal; they’re perfect for sharing your journey with everyone else. I’d love to read about your experiences—the fact that men of all different types practice chastity is really interesting.