Charlie’s such a good Sissy Phone Sex slut and doing training with mommy is paying off so much.
Daddy and I decided that maybe it was time to let Charlie have her first client since that… more than a little painful experience the last time she was on stage.
She was a little afraid, not having a real cock in her ass since that night but Daddy and I assured her that she’d be fine.
That this person would be gentle and love her tight little ass and cock.
So, I dressed up my little Charlie. Using a pretty satin pink dress with a sparkly hair bow. I put on a pair of white cotton panties with a matching pink bow on the front and a pair of shiny black mary janes. Before doing a simple and very natural makeup on her. She didn’t need much, she looked so much like her twin sister. Full pink lips, smooth cream colored skin, big blue eyes with long eyelashes, and naturally curly blonde hair.
She was such a sexy little Sissy Phone Sex whore and I could tell she was excited and nervous as her “Date” knocked on the door. I opened it to find our friend, he was a tall man and built like a tower. All muscle, beard, and intimidation.
I had a moment of uncertainty but he was paying us a lot to play with our Charlie so I invited him in. He smiled warmly at our nervous sissy and Carlie said hello with a cute blush and shuffle of her feet.
The man squatted in front of Charlie. “What’s wrong little one? You look scared.”
Charlie blushed brighter and smiled weakly at the man. “It’s… You’re big and…” she looked down shyly at floor, refusing to meet the man’s eyes.
“Well… Why don’t I give you a preview of our night tonight and we’ll see if you’re still scared of going with me?”
Charlie looked at the man surprised. “We can do that?” she looked at me after. “Would it be okay?”
I laughed, “Of course!” I agreed, liking the idea of seeing this man with my little girl.
So the man took Charlie’s hand. Her hand looked so tiny in his and led Charlie to the couch having her kneel on the cushions as he knelt in front of charlie. He lifted her skirt and rubbed his huge hands from Charlie’s little cock to the back. Cupping his ass, finger pressing up and against Charlie’s little asshole.
“Oh…” Charlie breathed, squirming against the man’s hand as he leaned forward. Licking a wet spot along the hardening little cock underneath. His hands moving to pull the panties down to his thighs. Sucking on his middle finger for a moment before returning it to massage against the little asshole. Pushing a finger in as the man takes the entirety of Charlie’s cock and little balls in his mouth. Sucking and licking and making Charlie moan and hump against the man’s face.
It only took a moment for him to cum, but he more than happy to go with the man after that. I can only imagine the amount of fucking that happened that night with my perfect little Sissy Phone Sex slut.
One of my favorite girlie games was fun with my teddy bear. I called him Charlie. He was a huge old bear that my brother won at a carnival game and gave to me. At night I’d climb up on top of him and hump him vigorously, rubbing my bald pussy against his ragged fur. I’d fantasize that he was my boyfriend. I’d even stick my hairbrush handle between his stuffed legs to make a pretend cock. “Fuck me, Charlie.” I’d moan into his fuzzy neck. Of course, he wasn’t alive but he gave me the best orgasms of my life.
