Jessy's new Clothes and Being taught to be brave
Posted 08-25-2016 at 10:49 PM by pt26
To start off this morning I awoke still plugged with the smallest butt plug. After calculating the time I came to realize that if I waited just a hour and a half longer I could hit a full 12 hours plugged (A NEW RECORD). Anyway Miss and i ended up chatting for a while which ended with me being ordered to the bathroom to remove the small plug and show off the small gape in Her hole. Miss them gave me the privilege of filling her hole with the medium plug for 30 min before again removing and showing off her hole.
I won't bore you with all the details but I ended up going to work for a little bit even though it was my day off. The good news is that it allowed me to pick up Jessy's new clothes! Miss wanted to see her slut right away so I slipped into the hot pink "spandex" shorts in the bathroom at work. They actually ended up being a little loose but according to Miss they make me look like a slutty cheerleader (high praise from Her). So no complaints on that end.
I got home and quickly changed since my sister was home sick. Well that was a mistake. Miss was not happy and I found myself holding a wedgie for 1 minute and then taking 10 pics for Her of her big ass being split apart by the wedgie. It made it difficult to continue baking the cookies I was making but I managed to finish.
Then came the hardest part of the day. Miss wanted a video of me naked, spreading Her hole on our couch. This started a 20 minute or so argument about me being scared the neighbors would see. I trade bartering button no avail. She demanded I obey so I finally took a few deep breathes dropped my sweats and underwear to the floor took my shirt off and shot the video as ordered. I was ssssooooo scared yet turned on at the same time thinking someone could walk by and see. Miss was so very happy that i summoned the courage to do it. I think I was only able to because I let Jessy free. This was such a growing experience for me because I am so scared of doing anything even remotely close to public. I feel like it was a baby step towards more truly public tasks.
I ended up spending the rest of the day hanging out with my sis and watching movies so Miss and I could not play any more. But as I went to bed I could not help it and Jessy came out. So here I am in bed typing this up wearing my sexy white thong under my new hot pink shorts and a t shirt hoping that I stay under the covers and my sis does not see. I want so much to try on my other clothes and model but I want to wait for Miss so she can watch Jessy's first time trying to put a bra on. Hopefully tomorrow I can report back on what it was like!
I won't bore you with all the details but I ended up going to work for a little bit even though it was my day off. The good news is that it allowed me to pick up Jessy's new clothes! Miss wanted to see her slut right away so I slipped into the hot pink "spandex" shorts in the bathroom at work. They actually ended up being a little loose but according to Miss they make me look like a slutty cheerleader (high praise from Her). So no complaints on that end.
I got home and quickly changed since my sister was home sick. Well that was a mistake. Miss was not happy and I found myself holding a wedgie for 1 minute and then taking 10 pics for Her of her big ass being split apart by the wedgie. It made it difficult to continue baking the cookies I was making but I managed to finish.
Then came the hardest part of the day. Miss wanted a video of me naked, spreading Her hole on our couch. This started a 20 minute or so argument about me being scared the neighbors would see. I trade bartering button no avail. She demanded I obey so I finally took a few deep breathes dropped my sweats and underwear to the floor took my shirt off and shot the video as ordered. I was ssssooooo scared yet turned on at the same time thinking someone could walk by and see. Miss was so very happy that i summoned the courage to do it. I think I was only able to because I let Jessy free. This was such a growing experience for me because I am so scared of doing anything even remotely close to public. I feel like it was a baby step towards more truly public tasks.
I ended up spending the rest of the day hanging out with my sis and watching movies so Miss and I could not play any more. But as I went to bed I could not help it and Jessy came out. So here I am in bed typing this up wearing my sexy white thong under my new hot pink shorts and a t shirt hoping that I stay under the covers and my sis does not see. I want so much to try on my other clothes and model but I want to wait for Miss so she can watch Jessy's first time trying to put a bra on. Hopefully tomorrow I can report back on what it was like!
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