The first challenge of the weekend was to try to successfully insert each of my 3 butt plugs inside my tight little asshole. I was being instructed by someone I trusted.
First he had me try the small one, it was relatively easy 😏 However, when he ask me to push it out with no hands I could not do it!
After the small one, he had me move to the medium plug. This one wasn’t as easy but not bad. Once inserted, he had me remove it half way to pump myself while I admitted that I was a dirty little anal slut. He had me pump my ass like people were watching while rubbing my clit as well. As I got close to cumming I had to beg his permission to finish. I begged and begged until he told me to cum. I made a mess all over 😜
But the task wasn’t done. I had to do what I failed to do previously, I had to insert the small plug back in and push it out without hand assistance. This time I was able to do it easily. Seeing how easy that was, he then asked me to do the same with the medium plug which was much harder. I was almost about to give up, but was able to get it out after a few tries.
Lastly, I had to insert the last and largest plug. He had me look in a mirror to see how gaped my little asshole is now. Still looking at the mirror I had to insert the largest plug and watch it go all the way in. After a few groans I was able to fully insert the largest plug and complete task 1.
I slowly removed the last plug with a smirk, thinking task 1 wasn’t that bad 🤷🏼♀️
