For the cute anon…

First of all, I'll tie you up and blindfold you, then I'll throw you on the bed.
Next, I'll wait a bit to see if you get a hardon just from the expectation, and if you do, I'll degrade and humiliate you for it. I'll even grab your balls and give it a gentle squeeze, but just as you start to fear the pain, I'll start lightly jerking you off to get you hard again.
If you start leaking precum, I'll lick it up and give a light suck to your cute dick. But don't cum, or else I'll push my finger into your asshole until I can touch your prostate and get you hard again. I'll also feed you your own cum.
After that, I'll cuddle you from behind and press my cock against your ass cheeks while I caress you. You may not be a femboy, but I'll make you into one, so I'll whispers sweet little things into your ears about how cute you'd look in a dress and with a fox tail buttplug hanging out. Just as you start to relax and fall asleep, I'll lube my cock and push it into your ass until you whimper in pain.
I won't go too hard, though, I just want to keep you scared of what may comes next, so I'll slow down and let your asshole adapt to the thickness of my cock. And now I'll start jerking you with my free hand while the other still caresses your hair and cheek.
Little by little, your tight asshole loosens up, and I start going in and out of you. Your precum collects on my hand, so I get a taste of it then make you lick it up while I push as deep into you as I can.
Your asshole is likely tight since my cock is quite thick, so I'll soon slow down so that I don't cum yet, but now I'll speed up my jerking until you cum, and I'll aim your cock so that you hit your own belly and chest.
Now I'll pull out of your gaping asshole and give your chest many kisses while occasionally licking up some of your cum. Once I reach the last drop, I'll save it and kiss you. It'll be a sloppy kiss because you're scared, and I'll also be jerking your sensitive cock to give you a bit of pain.
Next, I roll you on your back and spread your legs so that I can fuck your ass again while easily jerking you. You will get hard, and I hope its quick, otherwise I'll clamp your nipples for not being slutty enough.
I'm getting impatient now, so I'll fuck your ass harder and with a lot of lube. I'll tell you to warn me if you get near cumming again, and when you do, I'll swallow your cock and gather your whole load in my mouth, then continue to give you a sloppy one while some of it drips drown your cute shaft.
But after giving you enough pain, I'll fuck your ass slowly and give you another cum-filled kiss until it's finally my turn to finish inside your mouth. I'd like to cream your boy hole, but I want you to get a good taste of me so that you never forget my taste.
I'll untie you and remove the blindfold then cuddle while we rest. Next one, you're definitely putting on a dress, and I'll be a lot more rough with you.