Age 21: What would you do?
I’m in the process of replacing my entire sissy gear after I purged a month and a half ago, just when I was on the verge of getting fucked. At the time, I was also right before my university exams, and then the post-nut clarity hit.
It started all 3 years ago at 18 when I discovered that u can cum “like” a girl. I thought in that time how much better it would be, to have such an intense orgasm with waves going through your body. I also had a girlfriend then and was a little bit jealous of the orgasm. It all started three years ago, when I was 18 and stumbled upon a YouTube video explaining how to have an orgasm "like a girl" through anal stimulation. At the time, I had a girlfriend, and I sometimes envied her, or women in general, for their intense, long-lasting orgasms. After we broke up, I discovered porn featuring trans girls. That was the "click" moment for me.
This year, I discovered the subreddits dedicated to sissy play and feminization. I’ve even posted photos of myself as a girl, wearing a cage, a breast plate, a pink top to hide the plate, a wig, and extremely feminizing makeup. I also downloaded Grindr and immediately got a huge amount of attention; I’ve even arranged two meetups already. To be a girl, I have to be home alone; my family and friends mustn't find out about this side of me. The whole origin of my transformation into a sissy stems from the fact that, during my early experimentation phase, I could never really climax without touching my clit, or rather, I couldn't climax "like" a girl. Is this experience worth it? During my sessions, I often watch trans girl porn—or better yet, hypnosis videos—to really put myself in that mindset. In September, I’ll have three weeks home alone—the first time I’ve had that since exploring this side of myself. Is this just one facet of who I am, or is this who I’ve actually been all along? That would give me the chance to fully live out this fantasy and even invite men over.
Well, if I do go through with it, you’ll see it here or on another forum, lol.
Posted Jul 26, 2026, 11:50 PM UTC