Trying Anal Stimulation

My boyfriend has been hinting for a few months now that he wanted to try anal sex with me.  My experience with anal sex was with an ex-bf who “oops wrong holed” me once and it hurt like crazy. Since said time, my answer has been a resounding hell no on the rare occasions the subject has arisen. I finally decided to have a conversation with my boyfriend and explained my fear. He was understanding and the subject dropped. Or so I thought. To my surprise, I started thinking about it more and more and decided to do some research into the subject. Everything I read said the same things – anal sex should NOT hurt, use lots of lube, go very slow. I told my boyfriend I would consider getting some small toys and see how it goes before I commit to anything. One night after a few too many rum and cokes he used lubed up his finger and slid it in. It actually took me a little by surprise and it kept burning. I went back to research again and found the same info – anal sex should NOT hurt, use lots of lube, go very slow. I told him the next day that it burned and if that burned there was no way anything as big as him was going in there! He thought maybe it was tobacco residue on his finger that burned but I suspected it was a combination of surprise and the lube we were using which was highly disappointing since it is an organic lube! I decided to order a few super small butt plug toys as well as some anal lube before completely giving up on the idea. A few days later the package arrived and after our daughter went to sleep, we decided to try the smallest one. After warming up with oral and some vaginal penetration he lubed the super small butt plug up and slowly started to insert it. It was the strangest feeling – really indescribable. Slowly, slowly slowly he started to put it in and out a little at a time. After a few minutes the in and out started to feel better and better and he started to go a little faster, and a little faster. I had been using an egg vibe on my clit but it just wasn’t doing it for me. So, I grabbed my rabbit vibe and it wouldn’t go in! The plug apparently was making me tighter than usual which I didn’t think of previously. After about two minutes, I had an amazing orgasm.  Afterwards, I told my boyfriend we should have sex with the plug all the way in since it would make me a little tighter and he eagerly agreed. To be continued……

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