Sissy Training Phone Sex Pegging Charlie

Sissy Training Phone Sex Charlie is such a pretty boy.

It’d be such a shame if he didn’t use him for his full potential. He’s already been up on stage, used, shown his place and he enjoys everything but the anal.

I take blame for that as his mother though, I’ve been so focused on teaching his sisters how to be good little sluts that I haven’t really focused any of my training efforts on Charlie.

So today we’re going to focus on stretching his ass, teaching him how to be a good little cock slut and sissy for Mommy and Granddaddy.

To get Charlie started we’ve kept him dressed up as a female, as far as anyone outside the house knows I have 4 daughters. With Charlotte and Charlie being identical twins. Of course we know that’s not true, but Charlie has also living stuffed. Pretty little plugs slowly stretching his ass so he’s ready for a cock.

Today it will be my cock, it’s little above average in size and perfect for his training (as it seems all the men who want to take my poor little Charlie’s ass seem to be monsters in the size department.) and I have made sure to put my Charlie in the mind set.

“Ready to have your pussy fucked?”

His cheeks get so red when I start this, his tongue licking nervously over his lips as he lifts the skirt he’s been wearing. I see that one of his sisters put a vibrating cock ring on him keeping him hard and dripping with precum. They were so smart, or mean, I sometimes can’t figure out which but they seem to enjoy sexually torturing their brother as much as I and Daddy do.

“What a naughty little girl I have. Look at that little bitch click leaking already.” I teased, my hand wrapping around the little shaft stroking up and down and making my little sissy whimper. Humping against my hand as I twisted the plug inside of his ass before pulling it out.

“Ready for my cock baby?” I cooed, my strap on rubbing against the puckered asshole. Spreading the lube I had put against the head to ensure a comfortable fucking for my baby boy.

His breath hitched in a way that was both sexy and adorable and he moaned as I pushed the cock head into his tight little ass. I saw it stretch around my cock and I swear he pushed back against me. What a good little slut I have!

“How long ago did the sisters put your ring on baby?” I asked, still stroking his little bitch clit. He had a hard time focusing on anything but all the pleasure but managed a breathless. “Hours…”

“Aw, poor baby, let’s make you cum.” and I felt that little cock twitch in my hand as I started to thrust into my baby boy. My cock going deeper each time until my hips touched his ass.

What a sexy little sissy I have.

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