*** Legal disclaimer all characters are over the age of 18 ***
I arrived at her apartment, when I knocked the door opened from my knock. It was ajar, so I entered as she wanted me to. I called out "Jane, I'm here". No answer.
I went directly to her bedroom to find her on all fours wearing nothing but a pair of black four inch stiletto heels. She was facing away from me and there were a couple anal toys on the bed next to her.
"First thing is you are going to eat my ass and train my tight little hole for your big cock. If you think I'm ready I want you to butt fuck me and come deep in my ass." Jane commanded.
"I will do my best, have you been practicing with these toys?" I asked
"Yes"
"Do you have a favorite?"
"I love the beads and can only get to the third bead, I see what you are saying about being ready." She continued "I also started wearing the butt plug that's over on the dresser all the time, the internet says it will help train my ass. I just like that I have a dirty little secret while walking around the grocery store."
I smiled "That's sexy."
I knelt behind her and kissed her butt cheeks, she smelled nice. I pulled her cheeks apart and tongued her tight little hole. My cock started getting hard and rested on the soles of her slutty heels.
As I ate her ass my hips moved my cock along the sole of her shoe. There was a roughness about them that my cock liked.
I slid my thumb into her pussy and used it to put pressure on her clit with the knuckle of my pointer finger. With my hand rubbing her clit and invading her pussy, I licked her rosebud. The movement of my hand in and on her pussy started her body swaying, Jane started to help with the motion rocking back into my tongue.
She put her hands back and held her ass cheeks open for me as my tongue slid deeper into her hole.
With my free hand I pinned my cock against her heels by grabbing her foot and my cock in my hands grip.
A quick "oh oh oh oh oh yes please oh yes please MMPH YES YES OH YES!"
As she came I felt her anus expand allowing my tongue to slide inside her.
I kept my tongue as rigid as I could tongue fucking her through her orgasm.
When she stopped I sat up and grabbed her graduated anal trainer, it went from 1 inch thick at the tip to 3.5 inches a the base. The toy is designed to stretch her asshole more and more the deeper it slides in.
I applied plenty of lube and presented it to her anus and she indicated she wanted it. I used the toy in a circular motion to enter her forbidden hole. Once it passed her second sphincter she let out an audible gasp "OH".
I held it firmly and continued to rub her pussy as I never removed my grip on her clit. Again as I rubbed her clit, she backed down against the tool, slowly easing it into her bum.
I said "You have complete control here, the more you push back, the deeper and wider the trainer goes into your ass, do you feel it stretching you?"
"YES"
"Do you like the feeling in your ass?"
"YES OH YES"
"Do you want more? Do you want me to fuck your ass?"
"yes" It was a whisper, but still an acknowledgement that her ass was mine.
