Jan 12, 2019
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Sissy Jamie meets her first man for sex!

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Sissy Jamie, an Academy student has written us a very inspiring story of her first encounter. I wish her well for the future sissification progress and hope you all find an inspiration from here 🙂

It was a long time ago that I first thought that getting penetrated versus doing the penetration seemed more appealing. It wasn’t a vulgar thought, it was a real thought. It was the first time I admitted to myself that my assigned role in the world of sexuality was not the role I preferred. I wanted to be the one taken, the one being a source of pleasure because I knew that was going to be pleasurable all on its own.

I didn’t act on this, at least not outside of my fantasy life. But suddenly my best orgasms were the ones where I was focused on a cock inside of me. It was all fantasy and then I discovered a wonderful thing; toys! Soon it was butt plugs and dildos almost every day. I went as far as spending long hours at work with a butt plug inserted. It was great.

But soon I was back to the point of being almost there. I needed more. I started to challenge my thinking and ask myself if I would really receive a man’s cock? I found new fantasies, including the idea of becoming the submissive cocksucker to a dominant female. Soon it was a male I was submissive to. And then it happened. Perhaps I gave off more of a vibe then I anticipated, but suddenly I got asked to meet a man for sex. This was not romantic, it was sex. After about 1000 texts I agreed. We knew each other, he wanted an NSA submissive to take care of his needs.

He came to my house. He looked at me, said “I knew you would say yes” and headed for my shower. My heart rate was that of a marathon runner, but my small dick didn’t lie, I was excited. I decided to be bold and join him in the shower. Within two minutes I was on my knees taking my first cock into my mouth. I knew life would never be the same. We moved to my bed and I got to taste cum for the first time. I think I surprised even him as I swallowed his gift to me.

I lost my anal cherry that evening too. Like a real man, he had both stamina and recuperative powers and I got to be taken like I always dreamed. It was better than I had anticipated. Within minutes I was pushing back and moaning my submission to him. He fucked me for quite a while and when he finally came in my ass he leaned forward as he pressed himself as deep as he could go and said: “you’re mine forever now.” It was true. Unfortunately, he only used me two more times but to this day I would drop what I was doing and return to my knees for him.

I have experimented since then. I am very careful and cautious so this is not a crazy story, but I did find a great man who wanted a guy on the side. Our get-togethers are infrequent, but they always are great. I start on my knees and worship his cock orally and then when he wants, I offer my ass. He takes me from behind every time and fills my ass with his cum. When he has reached peak pleasure, we are done. My little dick goes untouched. I thanks him for letting me pleasure him, and I leave. I am happy and satisfied. I have been the source of pleasure for a man who deserves it. I always crave the next interaction, but they are always on his terms, the way it should be.

It is from this that I have discovered that not only am I a true submissive (I have also gladly taken pain and punishment from a mistress) but that I am happiest when I am the girl, the sissy. I have found myself seeing shapely and attractive women and lamenting that I am not. I have found myself in panties and wishing I had breasts. I have come to the realization that if I looked better I would have more opportunities to serve real men. And that is where this always goes; there are men and I am not one. But instead of fighting that I seek to take my place as the attractive, happy, uninhibited, sexually charged source of pleasure for the real men out there. My mouth is theirs, my ass is theirs, and when I am a full blown sissy I will be able to just focus on them and their pleasure. My old life will be secondary and my new life will be entirely focused on being the best, most available, most attractive sissy there is.

Will I reach this dream? I can’t say. But I know like many others, being a sissy is not a journey I can avoid. It is my destiny and my calling. Will I be the perfect sissy used by many men or owned completely by one? Only time will tell. For now, I focus on pushing past my inhibitions and the norms that are supposed to govern my life and seek my place as a true sissy. The journey is happening and that alone is worth it. Sissy forever, I just need some more time and help to get there.

Author: Sissy Jamie

Sissylover Academy student

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Sissy Stories · sissy training

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