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.