It was a Greek guy I had met online. We texted a lot and talked about each others sexual experiences and turn ons. We meet a few times and the sex with him was absolutely awesome.
Some day I told him that I always found the idea of anal very interesting (since I had read a very hot NSFW comic when I was 15), but never tried before. All the guys I’ve been with before told me they would never do it as they thought it was disgusting.
But that guy was totally up for introducing me into anal! I was so excited to try it out.
So he suggested I should buy some butt plugs, and he also sent me some “first time anal” porn videos, and they turned me on A LOT.
The next days I began playing with my asshole when I masturbated.
Oh damn, what did it hurt when I started shoving my dildo inside, so I went to buy some lube (I’ve never needed lube before, as my pussy is always wet – but for anal I noticed that need to be lubed up properly).
As he told me that it would be best for me if I would start wearing butt plugs to “destress” my asshole, I also bought some in various sizes and started wearing one throughout the day. In the beginning it was a very small one for only some minutes, going up to wearing a very large one for an hour or two.