Anal Pleasure

Hi, I am nick i'm 21 and I lovee trannies. I have been jerking off to shemales for quite some time now, at least a couple years and I always get really turned on thinking about fucking them. However, for some time now I've been feeling a little curious of how it would feel like to get fucked by a Tranny.

So a couple months a go I started putting a finger in my ass while jerking and watching porn. I started to enjoy it but i think i got most of my pleasure from the jerking and not from the finger in my asshole. Yet still I remained curious of how a tranny gets pleasure when fucked in the ass, and I wanted to continue to explore anal pleasure and maybe someday even get fucked by a tgirl.

I bought a butt plug, a dildo, an anal douche and lube about a month ago in hopes to continue exploring anal pleasure. I started watching a lot of Sissy hypno trainer porn videos and slowly fingering my ass in preparation for the plug. It hurt a little bit but it was manageable and enjoyable because i was still jerking off. A little weed and the sissy hypno trainer videos helped a lot. I then, after douching I moved up to the plug and after a quite some struggle and pain I got it in. Once it was in i found it quite enjoyable, yet i still feel i got most my pleasure from the jerking and not from having the plug inserted in my asshole. However once the plug was completely inside, the pain decreased, although this may be because of the shape of the plug. It is much thicker at the top. But i think most butt plugs are the same in order to recreate the head of the penis. I continued to jerk my cock while having the plug inserted and kept watching sissy hypno training it felt good but then , again, i got the most pleasurable sensations from the jerking and not from the plug.

I still wanted to get anal pleasure for the first time. I felt curious and the thought of having a cock in my ass, (or as they referred to it in the sissy hypno videos; my boipussy) kind of turned me on. so about half an hour to 45 min after having fully inserted the butt plug in my asshole, my boipussy, I felt it was time to try the dildo.