The Beginning

I’m going to start this series of fantasy stories about how I would like, or rather, fantasize my journey should be, from the beginning. To begin, we must go back many years to the time when it all began.

As you know, I live with my family: my parents, my sister, and my brother. My sister is the oldest, I’m the middle one, and my brother is the youngest. Like most sissies, I started by grabbing my sister’s panties and putting them on. I don’t know why that turned me on. It wasn’t incestuous at all; it was the fact of wearing panties and the feeling I got from doing it. I was a teenager with raging hormones, constantly watching porn. Over time, conventional porn gets boring; it’s always the same: a man fucks a woman and cums anywhere on her. I moved on to watching anal porn. I was fascinated by watching those women take cock in their asses and enjoying it. I was also left speechless by some gapes after being fucked by a big black cock. I was beginning to become more interested in the sensations women experience than men. Being a man, pleasure comes with orgasm, which only lasts a few seconds. Women, on the other hand, can experience much greater pleasure over a longer period of time. I wondered what women felt when they were fucked and climaxed. I started masturbating with fingers in my ass. When I reached a certain point, it became pleasurable. I kept trying bigger things. I always came while jerking off. Until one day.

After months of using small objects, I saw a large deodorant, like a real penis, and decided to try masturbating with it. It wouldn’t fit. I spent several minutes trying to get my entrance to give way to the object. But to no avail. A few days later, I tried again. This time I was successful. After sucking it and covering it with a lot of saliva, it finally entered. It stung. I held it still for a few seconds. The pain was fading. I started pushing it in and out, without pulling it out completely. It had been so hard, I didn’t know if I could do it again. I felt sensations I’d never felt before. My body was asking me to moan, like women do. My penis was rock hard, even though I hadn’t touched it. I was just masturbating anally, but my cock started to spurt more precum than ever. I pulled it out completely. I rubbed it over the head of my cock, coating it with as much precum as I could. I tried again, and this time it went in easily. I’d learned that precum is the best lubricant there is. Now I was pushing that makeshift dildo in and out completely. I felt like moaning, but I held it in so no one would hear me. Then it happened.

Without even touching my penis, I had the strongest orgasm of my life. I was cumming copiously and feeling a pleasure I’d never felt before with that object stuck in my ass. This orgasmic sensation was longer and more intense than a normal male orgasm. It was my first sissygasm.

From that day on, I became interested in sissygasms and the sissy world. I watched porn of sissies and trans women who ended up cumming without touching their penises. Time passed, and I had two or three more sissygasms. Then I stopped. I was a man, and that wasn’t what men did. I started dating girls my age and having my first relationships. The expectations for my first fuck were huge after watching so much porn and seeing how much those men enjoyed themselves. I didn’t live up to those expectations. I was disappointed. Is that what it felt like to fuck a girl? It was disappointing. Sissygasms made you feel so much better. But they weren’t just for men.

Years passed, and I went to college. I dated a couple more girls, but I didn’t feel fulfilled. There was a year when I was on the back foot and I got back into porn. I watched those sissy videos again; there were many more of them now, and they were better quality. But I didn’t go any further and kept dating girls.

I finished college and started working. I had a relationship for a couple of years that didn’t end well. Do any relationships end well these days? Soon after, I got back into porn. Now there was all kinds of content, Onlyfans had exploded, and many women were now “models.” With every GIF and video I watched, I felt more and more drawn to the idea of becoming a sissy. So much so that I saw myself as less of a man. I stopped masturbating the conventional way and started doing it more woman-style, rubbing my hand over my clitty. When it got completely hard, I would stop until it was limp again, and then I would start again. I was like this for a couple of months until I got to the point where I am now writing this text.

I can say I’ve completely succumbed to the idea of becoming a sissy. The only thing keeping me from my goal is money. If I could leave home and buy my own, I’d start my transformation right now.

That’s why I’m going to write this series of stories about my fantasies.

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