Monday, January 24, 2011

Today is the day

I've never taken a boy's ass with a strap-on.


I've come close. Real close. I had the head of my big purple cock inside babyboy's very tight ass. One thrust of my hips and I wouldn't be writing about this cherry of mine. But I was using the harness and dildo a former girlfriend and I had purchased together. We had selected a length and size we'd both enjoy vaginally. I never thought for a moment I'd use its ample length and girth on an ass let alone a male ass.

The truth is I don't feel compelled to play with every ass I come in contact with. And although I maintain a theory that every male is an ass slut or an ass slut ready to happen, I haven't played with many trained for regular ass play.

They all have tight little pseudo virgin asses. None could have taken the girth of my purple cock.

I have enjoyed watching a few of them suck it, pushing my big purple cock deep into their throats.

And then I broke the harness on the girl. *sigh* Good times.

The purple dildo remained in my toy bag and occasionally made appearances in play such as when I tied my sub to a table and forced him to suck it, then masturbated with it before I forced him to suck it some more.

*sigh* Good times.

Could I have bought another harness and a more reasonable sized cock and fucked a boy's ass before now? Sure. But the truth is I have enjoyed the anticipation of taking a boy's ass for the first time.

Perhaps I've nearly romanticized it. I've waited so long and I want it to be with the right guy at the right time.

I can't even type that without giggling at the ridiculousness of that idea but it's probably true. I've been "saving myself."

And today is the day.


  1. Interesting. For many folks, strapon sex is merely play. I think since you've saved it for so long, whoever you share it with can regard it as a very meaningful act. I've always regarded the act of taking the ass to be very meaningful in a femdom relationship. Being the first makes it even more special.