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.
I went out to a party last night. It was a business soiree, so of course I looked my very best. I had this long, ruby evening gown on with a neckline that wrapped at my throat like a silk scarf and dangled down my back only marginally covering the plunging back that dipped to hug my firm derriere. He was very obviously the envy of every other man at that party. Married and solo alike, they all found a reason to come talk to him and introduce themselves to me. Some flirted relentlessly, even with him standing right there next to me. The deflections are second-nature. After all, I am here with him, and it’s very disrespectful for these boys to play such games. I kept my hand firmly attached to his arm when such men were fawning over me, and leaned back ever so slightly when his hand would move to the small of my back, as much a reassurance that I was with him as a signal for the men to back off. My favorite part was whispering in his ear between such encounters of all the wonderful things I wanted to do to and with him once we were safely out of the party. Needless to say, he cut out as soon as was socially acceptable. 😉
