Sissy Jamie meets her first man for sex!

Sissy Jamie texting to his alpha male
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 🙂

Sissy Jamie meets her first man for sex!

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

23 thoughts on “Sissy Jamie meets her first man for sex!

  1. Charles Demos says:

    My sexy dominant white ex-wife and her big black dominant boyfriend turned me into a little dicked feminine looking submissive white cockloving crossdressing sissyboy faggot on our honeymoon over 6yrs ago. Since then I’ve been living with her 2 big black dominant friends with huge delicious black cocks as their crossdressing cockloving white sissyboy housemaid and sexslave.

  2. Sissy Julia Love says:

    Thank you for sharing Jamie. I have a lot of the same impediments I’ve put in front of my happiness too. I hope I too can realize my full sissy potential and be the source of pleasure for real men. And in giving that pleasure, realize my own true fulfillment.

  3. Sissy_sara says:

    what a lovely story! I envy your courage. I dont know if Its that I dont dare to take real cock or that I dont want to take real cock. If that makes sense?
    Anyway I am very happy for you! Keep it up girl! 🙂

  4. Cumslut69 says:

    I’m needing some implants and a whole slutty wardrobe and than I wanna get together and join your school until i am trained properly. I’m in my room waiting for a mistress to cuckhold me i love cum filled pussy hole that loves to be molested by a bunch of strange
    Cock. Bring that cream pie home and I’ll take care of your nasty things all day and night with my eager mouth

  5. Jennifermarie says:

    I love being a sissy lady boy. I’ve been taken many times and love every minute of it. I love getting dressed up and going out, one night I was taken by three men sat on dick sucked on other! The other was was between my legs sucking my dick. Then that 8in throbbing cock exploded in my ass and then swallowed the cum from the dick I was sucking then came all into the others mouth. Best time of my life.

  6. Howie says:

    I enjoyed your story sissy Jamie. My desire is to meet a sissy early in transition and training to guide her and mold her into my dream girl. So that she will look stunning in her wedding gown.

  7. Sissy Brittney says:

    Thank you for your honest and wonderful story of the night that you truly became a girl. It was very inspiring as well as comforting to learn that there are other sissies just aching out there who think just like I do.

  8. StaciSmith says:

    Lived reading your story as well as find your truth in the matter. Over had relationships in my past with both sexes. I always found love in the ones where i can just be me. Most of times sadly, it was all me giving and then taking. Would love to find the one i can just give myself to and have it be the forever one. I’m sissy and TS and often times think they go hand in hand. As so close in proximity. Is like we are what we were. We have feelings and want to look and feel our best.

  9. Alan says:

    Well, well, well we can surely see and hear that the MK Ultra mind control and the Monarch mind control Beta sex slave programming is still alive and well being beamed to the populace programming many unsuspecting innocent people who have had their hormones genes and chromosomes altered & made to feel feminine like they are female instead of male ! You should do your research on the history of mind control and the fact the whole world is being beamed with radio frequency neuro-frequency microwave, electromagnetic beams saturating the population with these subliminal programs to make people gay so they will not make babies it is part of the world population reduction program under document 200 issued by Henry Kissinger Secretary of State of the United States under the Nixon Administration , who was working for Nelson Rockefeller & the Rockefeller Foundation to plan the future of the World without your knowledge or consent , or awareness ! Yes you have all been deceived programmed to be a gay sex slave believing you are changing sex from male to female ! What a bad joke !

    • Violet says:

      The only bad joke here is your argument buddy. Even those of us who haven’t done research can recognize that. (I highly recommend you check this site out for some more info, it’s the Child Mind Institute’s official website; And, even if you think it’s wrong, why are you so vocal if we’re so stupid? Are you afraid? Are you trying to suppress something within yourself? Even if that is true that’s OK, I just can’t stand seeing you attack people who did nothing wrong towards you or anyone else for no reason. That said, please have the day you deserve.

      With love,
      Your local trans girl, Violet

  10. Staci306 says:

    Very well thought out as am i truly upset for my actions of last night. Still shedding tears over it all and how it unravelled. All my fault. But regrets. But love the story of outcomes for which the story is about. Like i can relate.

  11. sissy kitty says:

    Hi all,
    i just started the Sissifiction Academy and reading this story makes me more excited to part of this Academy.
    i hope i will be a good siss some day!

    Thank you,
    sissy kitty

  12. beckyharper says:

    What an very well done and fun read this was! I loved how introspective it is! Great job Sissy Jamie!

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