_everyone mentioned here is at least 18 years old._
I’ve (M53) invited Joey (31), a pretty girl, to my hotel room. She wants to be good for daddy. Joey goes straight to the bathroom to get ready. She’s already shaved all over, locked up her little cock, and is wearing a big buttplug. Now she’s getting her sexy little body dressed up for me.
I’m sitting in a comfortable chair when she comes out to show off her skimpy outfit. I stroke my cock under my shorts as she dances around and shows me that she’s not wearing panties under her silly little skirt. I pull the plug out and tease her anus with it, then shove it back in place.
Joey knows what to do. She kneels before me and pulls my shorts down my hairy legs. Daddy’s cock is already stiffening and she just touches the head with her tongue to get some precum that’s leaked out. But she’s not here to tease me. We’ve been texting all morning and I’m horny as fuck. I pull her head down by the hair and she starts giving me delicious head. My balls are already full as she attacks my dick like a good little whore. I tell her what a cheap slut she is, sucking me off in the middle of the day in a hotel. Joey murmurs, sending vibes through my supersensitive cockhead.
She knows to jerk me off onto her lips so I don’t fuck up her makeup until later. She pulls me out of her mouth as I start busting my nut on those pretty lips. I’d been edging for a few days, so there’s a lot of cum. A lot. I use my cock to push some of it into her mouth and she licks her lips to get the rest of my sperm so she can swallow for me.
For the next half hour we lay on the bed and watch porn with pretty whores, mainly women getting fucked up the ass. Joey is a good fluffer girl, stroking me to get me hard. I then lay on my stomach and keep watching while she reams and fingers my ass. Finally I’m ready and she gets the lube.
Joey makes a little show of pulling the plug out. She gets on her hands and knees and I lube up her poopchute. She asks me to go slow but that might not be possible. I oil up my cock and press the head against her private opening. She whimpers a little but she’s a good girl and lets me penetrate her sphincter. She squeals in pain as I push all the way in. Her textured rectum is so fucking tight and warm. I pull out and stretch her out a little more. She asks if she can release her little locked-up penis. Whatever floats her boat.
Then push my erection back up her hole and start pounding. The poor little slut will be a little sore tomorrow. Joey asks permission to jerk herself but I say now. I need her to maintain a stable position so I can sodomize her. I pull her head back and grit my teeth as I tell her what a cheap whore she is for daddy, and I make her talk dirty back to me. She’s s little reluctant but she does ok. We’ll work on it.
Suddenly Joey says “oh fuck, Daddy. Oh fuck. Can I please cum? I can’t—“ I tell her, of course it’s ok. Her sphincter tightens, throttling my cock, and I have to push harder to keep using her asshole. She moans as her stiff little pecker begins spurting on the bed.
“You’re going to suck me off and jerk my cum onto your face,” I growl. “Get ready.” I take one final look at my cock pistoning in and out of her backdoor, then I pull out with a wet, nasty-ass sound.
Joey doesn’t want my dick in her mouth right now but she’s going to be a good girl. Straight out of her ass, she takes it and sucks while she’s jacking me. In only a couple of seconds I push her head back a little. The first rope of cum goes just above her right eye as she’s pulling my cock out of her slutty mouth. She jacks the rest off onto her forehead, from where it begins rolling down. I stroke a few last times as she’s holding me—my cock, wet from her mouth and asshole, slipping between her fingers.
Source: reddit.com/r/eroticliterature/comments/12itclf/using_a_sissy_to_get_off_m53m31_i_swear_im