So I would definitely consider myself a top and up until now had no interest in bottoming and the only experience I had was extremely unpleasant. Recently though I’ve become curious about bottoming as my boyfriend is vers and I would like to know what all this fuss is about bottoming lol. We’ve tried to have sex twice and I also have a few toys that I can use on my own time, I have plenty of lube, poppers that I’ll use occasionally and each time I’ve cleaned out really well. The issue I’m facing is that every time I try it feels very uncomfortable, yesterday I used a prostate massager which was probably the most comfortable thing I’ve used and actually seemed pleasurable sometimes but if I use anything larger like a butt plug a dildo or my BF’s dick it is very uncomfortable and feel like I need to go to the bathroom and the feeling doesn’t go away. I have tried to stretch myself open to try and relax my ass more but it hasn’t really been working.
Is there anything that I can do differently to try to loosen myself up/make it feel good? I want to be able to feel pleasure instead of constant discomfort and have my ass loosen so I can actually take something.