Jessy Time and some serious stretching....
Posted 08-31-2016 at 06:33 PM by pt26
Well I had a pretty good chunk of time free for play with Miss. I had been nervously waiting and finally it was here!!!!
She started off with being plugged while performing some tasks around the house (weeding the front yard was scary due to the loose sweats and black thong). Then she Jessyfied me... I was to look through my sister's clothes for some shall we say "fun". I stumbled upon some tight fitting legging kind a things that ended up being see through too. Miss LOVED them and I was tasked with taking several pictures and short videos showing off my thong clad ass through the leggings.
I was then ordered into my frilly pink set and asked if I wanted some cock. I begged and pleaded Miss to fill her little sissy up. I then spent the next few hours fucking myself in various positions I won't bore you with all the details but thought I would share 1 in particular.
I was to attach the dildo to the floor so I could lay back over it and ride it deep inside but so Miss could have the perfect angle of my moaning face and ass. By this time i was so horny I was bouncing and fucking deep, hard and fast. Then I began feeling it deep inside kinda beneath my balls. A strange feeling of pleasure it slowly began to build tingling up towards my cock. I suddenly realized... I may be able to cum from this. I kept going harder, faster the feeling building when "shit" the stupid dildo popped out. I also came to my senses realizing if I orgasmed Miss would be VERY upset. She was pleased and allowed me to edge several times after.
Since I was loose she decided it was time.... so, I went and grapped the large plug and my lube. For my tight ass this thing is HUGE at its thickest point it's bigger than 3 of my fingers but in a circle (if that makes sense). Well I tried and I tried and I tried but I just could not get it in.... it's just too big right now. I was sooo disappointed because I had really tried to get it in and actually came pretty close. Miss had even said she may let me cum if I got it in but alas include not.
So, there it is an afternoon of being Jessy and some attempted stretching. If anyone has any tips for getting it in they would be greatly appreciated.
Miss's slightly stretched and horny Sissy slut,
Jessy
She started off with being plugged while performing some tasks around the house (weeding the front yard was scary due to the loose sweats and black thong). Then she Jessyfied me... I was to look through my sister's clothes for some shall we say "fun". I stumbled upon some tight fitting legging kind a things that ended up being see through too. Miss LOVED them and I was tasked with taking several pictures and short videos showing off my thong clad ass through the leggings.
I was then ordered into my frilly pink set and asked if I wanted some cock. I begged and pleaded Miss to fill her little sissy up. I then spent the next few hours fucking myself in various positions I won't bore you with all the details but thought I would share 1 in particular.
I was to attach the dildo to the floor so I could lay back over it and ride it deep inside but so Miss could have the perfect angle of my moaning face and ass. By this time i was so horny I was bouncing and fucking deep, hard and fast. Then I began feeling it deep inside kinda beneath my balls. A strange feeling of pleasure it slowly began to build tingling up towards my cock. I suddenly realized... I may be able to cum from this. I kept going harder, faster the feeling building when "shit" the stupid dildo popped out. I also came to my senses realizing if I orgasmed Miss would be VERY upset. She was pleased and allowed me to edge several times after.
Since I was loose she decided it was time.... so, I went and grapped the large plug and my lube. For my tight ass this thing is HUGE at its thickest point it's bigger than 3 of my fingers but in a circle (if that makes sense). Well I tried and I tried and I tried but I just could not get it in.... it's just too big right now. I was sooo disappointed because I had really tried to get it in and actually came pretty close. Miss had even said she may let me cum if I got it in but alas include not.
So, there it is an afternoon of being Jessy and some attempted stretching. If anyone has any tips for getting it in they would be greatly appreciated.
Miss's slightly stretched and horny Sissy slut,
Jessy
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