There's this big-dicked Daddy-type man who used to fuck me, but he's quite demanding and since I haven't been fucked for a while he won't let me visit him. He wants to know my arse is in shape to take his large cock (21cm, so roughly 8½", and with significant girth) as well as some of his toys and whatever else he fancies. He's the one who has previously gotten a slim dildo 42cm / 17" inside me, fisted me, and dropped a length of rather heavy metal chain into my gaping hole, so you can see he's not quite vanilla in his tastes.
(This pic is from the first time he successfully fisted me.)
And me showing up with a hole that's not used to being opened? Well, he's not interested. He gets plenty of offers from guys that are younger and fitter than me, so if I'm not up to the job there's no point in it for him.
Which is fair. We all have our preferences.
Anyway, he DOES want to use my arse again, but he wants me ready. So...
He told me if I wanted his cock again I had to go to a specific address last night at 9pm sharp. It was the house of a friend of his with slightly lower demands, so perhaps he could break me in. That's all I was told.
So I showed up, not knowing quite what to expect. The man let me in, told me to strip down to my underwear and then he put a blindfold and a pair of handcuffs on me. Okay, this seemed to be heading in a good direction, I thought.
He unzipped his trousers and ordered me on my knees to suck him hard. I did my best, and it was definitely growing and growing in my mouth. This wasn't a small one! Perhaps not as big as Daddy's, but definitely well above average... I did my best, and it seemed to be satisfactory, because after a while he was hard as a rock and told me to get up.
He led me into another room, where I was coaxed on to a bed and told to get on hands and knees. And then he presented me with two options: He could rim and finger me open for his cock, or he could just lube up and go straight in. But there was a caveat: Whatever I chose would be reported back to Daddy...
So I knew there was really just one option.
"Good boy", he said after I begged for the cock with no warm-up, and then he was nice enough to shove a bottle of poppers into my cuffed hands so I could at least have a bit of help. Three deep hits, and then I begged for the cock!!! And got it.
Boy, did I get it! He had poured copious amounts of lube on my hole as I was sniffing poppers, and then he rubbed his cock head a bit up and down my crack - and then he went in! Hard... And balls-deep in the first stroke. I didn't even have time to moan or whine, really.
But he was in; I was being fucked. So far I hoped I was doing okay in terms of what would be reported back.
And I was fucked rather furiously and hard, but thanks to the poppers it didn't take me many seconds before I was really, REALLY enjoying it! This man was driving it in me hard from all sorts of angles, hitting every imaginable spot inside me. And, I suspect, doing his best to get me to open up...
He had some stamina, but after a while I could hear him getting close, and then I felt him unload deep inside me.
And... That was it, apparently. I had expected/feared a much harder treatment, but this was just a rough fuck, which I tend to enjoy.
I was led back into the hallway, un-cuffed and told to take of the blindfold, get dressed and leave.
When I got home there was an email from Daddy:
"You seem to have done well, Boy.
But you're not ready yet. Go to his house again tomorrow evening at the same time."
So... I guess tonight I'm going to get fucked again?