Like a Virgin: Part 2

I'm ready, please, and so is my ass....

I’m ready, so please do what must be done to my pussy ass….

I can remember the moment precisely, the exact words that came out of my mouth when my shrink began our regular weekly session by asking how I was feeling:

“I need to be filled.”

The words just spilled out of my mouth.   I hadn’t rehearsed, I hadn’t reflected.   Never had I acknowledged this feeling, much less articulated it:

Yes, I wanted — indeed, needed! — to be fucked in the ass.

Until that moment, this carnal desire was a well-maintained secret, especially to me.  My consciousness always felt a disdain, disgust even, toward anal sex.  It seemed to have about as much appeal as a prostate exam or colonoscopy.   Plus it was dirty.

But now, having lived full-time as a woman and ingested girlie hormones for nearly a year, I suddenly felt empty, incomplete.  Not psychologically, but physically.   Deepthroating — which I loved! — would never satisfy my hunger.  I needed something more, much more.

The shrink always looked especially wise when he nodded, and he was now nodding vigorously.  “What do you mean exactly?” he didn’t have to ask.  Not only did he understand, but also I was apparently validating all his long-held theories about male-to-female transsexuals.

So it was that, with the good doctor’s tacit encouragement, I began my anal experiments: tampons, butt plugs, beads, dildos, enemas, lubricants….

My boyfriend at the time, very patient and practiced, helped.   The fact that he had a so-enormous-it-was-scary cock helped, too, curiously enough.  Sure, it was plenty painful, particularly at first.

But I can’t begin to communicate how incredibly exciting it was to keep the visual image of his huge, thick, hard cock in my mind while he plowed me.

About Joy Saint James

Day job in Big Banking. Elsewhere I'm @ScholarlySlut, whose essays and erotica have appeared in various print anthologies and websites. Email:

41 responses to “Like a Virgin: Part 2

  1. JeanetteCD


  2. But toys come with no emotional baggage!

  3. I must say Joy. what you experienced is beautiful and painful, in a Loveing way.
    The extacy, of the desire, to be fucked for the first time, is the opeing of new passge to your body and your heart and your soul.
    its great, you had some at that time be very compassionate you, physicaly, with careness.
    and the careness, to make you feel everything you ever wanted to feel inside you.
    That moment will last forever in your mind ,heart, soul, body.
    Your hunger for desires of feeling the flesh, of someone to fill you with total extacy, of love in your body, is a fantasy, that became reality for you.
    It seems your shrink, gave you good insights and encouragement, to fill your , heavenly body, with no meantal, fears………
    Its a tradition to to most to use , toys of such, to practice for the first time, and wait for that true moment of actualy being filled with a hard cock, inside you.
    What you have experience , Some can only dream of haveing that, and especialy, for the first time, with someone who is compassionate to your body and heart and soul….
    Now you have passed the virgin gate, so your journey is now, to seek, one who is pure in the heart and body and soul, to love you, and to cherrish you forever.

    because I know I would…. Sincerely zarkye

  4. Al

    You are remarkable.
    I am at a loss to describe the array of feelings you evoke in me. in this short entry you have made me feel incredible empathy, intense lust and jealousy.
    I will try to be as honest and truthful in my response.
    You allow me understand what it is to be you in at least one tiny moment of your life. It feels so intimate and so beautiful. You make me feel overwhelmed with desire, it is almost to much to handle but it is exquisite! I promised to be honest so I will admit I am so jealous of your then boyfriend because he got to love you and be your first and I assume he was also loved by you. I hope he valued that. I am sure he did but I must believe he could not possibly value you the way I would.
    Thank you for really putting yourself out there for me. I know its for others as well but I don’t want to think about that right now.

  5. Rakteem

    U made me speechless. That’s sheer grace.

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  22. The Sin Doll

    Wonderful words. Thank you for putting this out there!

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