A good, thorough fucking

It had been awhile since I’d been able to give Sounder a real fucking.  We were both eager for that to change.

And from the very first moment I bent him over the island in his kitchen, and slid a finger in him, he was every bit the eager anal whore you’d expect a sissy to be.  Pushing back against me, humping himself on my hand, wanting to be filled up, it was really hot.

I always love watching him squirm.

It was especially hot once I got him in the bedroom and started putting toys in him.  I will never get tired of watching him fuck himself on whatever’s in him.

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I can’t wait to take a picture like this, but with a real cock inside him, instead of a toy.

At first, he was so tight.  It had been too long since I’ve really had my way with his pussy, so I was gentle.  I started small and gradually worked my way up in size.  Because I’m so totally nice like that.

All I know is that he’s going to make a man very happy when I put a real cock inside him.  And how awesome are backless panties?  The more he wears them, the more I love them.  So sexy, so convenient.

I don’t even have to undress him, all I have to do is bend him over.

When I finally switched to my strap-on, the look on his face as I filled him up was priceless.  It had been awhile since he’d had anything that big in him.

I turned him onto his back, pushed his knees up, exposing that tight, pink ass, and rammed my cock in.

He looks damn good with something in him, by the way.

I don’t think it was a full minute before he came.  And then came again.  And again.

We’ll definitely have to work on his stamina.  He starts getting exhausted and raw after about ten orgasms.  He’ll have way more than that when he’s fucked by half a dozen men.

Eventually, though, I had mercy on him, and decided to play with my clothespins, instead.  You know, because I’m nice like that.

 

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Super nice

He really is so adorable when he’s in pain.  And the best part about clothespins is that they hurt more coming off than they do going on.  Makes it easy to drag out the pain, really savor those reactions.

And he’s got a new hypnosis recording to listen to every day.  I’m going to brainwash him into a mindless sissy fucktoy.  He’s going to dream about being gangbanged, he’s going to crave men’s cocks in him.

Eventually, it will even seep into his everyday life.  He’ll be at work and see a hot guy, and an image of that guy bending him over his desk and fucking him will flash through his mind.  He’ll imagine what that man’s cock will taste like.  What it’ll feel like to have it throb in his mouth as it shoots down his throat.

Just a quick flash.  But they’ll start happening more and more, until that’s the norm, until he doesn’t remember what it feels like not to picture men fucking him.  He’ll forget what it feels like not to crave a man’s dick inside him.

It’s going to be so much fun, it really is.

6 thoughts on “A good, thorough fucking

  1. Coyote from Orion says:

    So apt that Batman is on the TV right now calling Alfred cos he’s tripping.

  2. Tonydallas says:

    Good stuff. You’re boys are very fortunate to have someone like you.

  3. Hapa says:

    Best part of my day so far. Gotta say I’ve enjoyed hearing about Sounders transition for the last year or so. Any chance his gangbang happens sooner than later? Dying to see him take the next and most meaningful step.

  4. Drew says:

    Thank you Domina Jen, what an honor it would be to be trained by you

    Drewtoserve

  5. your sissy is lucky to have a Mistress who wants to use hi, like a slut..all of sissies want that. love the backless panties. cannot wait for the sissy to be filled with real cock…love looking at cock in a sissy…ashley cox

  6. slave sindee says:

    Wow that is really hot and exciting. There must be hundreds of sisiies wanting to serve You. he is one lucky sissy

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