Nervous girlfriend shares first time anal experience

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After a few minutes I told him I was ready. He pulled the butt-plug in and dipped his tip into my hole stretching it significantly wider than the butt-plug had. I yelped from the pain asking if it was in. He assured me it was just the tip but he would go slow. I continued to whimper the pain consistently getting less bearable and my eyes watering uncontrollably until I cried for him to stop. He pulled out immediately and we stopped. I apologized and explained to him that I didn't think I could do it. I put my robe on and went to wash my face, my mascara had run from the tears and I looked like a racoon.

For the next few months I kind of gave up. I'm just a tiny with a tiny asshole. just wasn't for me. One night, while staying at Sam's I couldn't keep myself off of him, I climbed on top of him and I wanted him to get a good view of my bouncing up and down on top of his dick. I sat in reverse cowgirl and worked his to give him as much pleasure as I possibly could. He slapped my ass with an open palm. I moaned, as much as I love it when he's a sensitive caring lover, I love it even more when he is aggressive taking what he wants and maybe even hurting me a little in the process… in a good way of course. I want it. I crave it. This time he did something a little different though. He didn't give me another good slap, instead I suddenly felt a pop and this thumb circled around the inside of my ass. I was now riding both his throbbing cock and his thumb. My breathing became shallower until I let loud a series of loud cries while my released itself with pleasure.

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After that, anal was on my mind again, and this time I was going to do it right so that not only could I give Sam the pleasure that he deserved from my tight hole while getting another intense for myself. I wanted it bad. So I googled positions and what I could do to make it better. I told Sam what I wanted and used it as dirty talk while we had a quicky before going to sleep that night and an excited glimmer sparked in his eye. After we finished I told him it wasn't just talk, I was serious and exactly what I wanted to him.

The next evening we went to dinner with some knowing full well what we would be doing that evening. It was to focus because I was so turned on by the (in my mind) thing that we were going to do, but I had a drinks to ease my mind and hopefully loosen me up a little. After we left dinner we stopped at the adult store on our way home, a little buzzed I flirted with him while we looked at the walls of toys and helpers on the walls and shelves. We made fun comments about the products and tickled each other as we joked. I loved shopping with him in this store. We got to the anal play section and looked at the different sets of trainers settling on a set of 3 different sizes their tips tapering from small to larger, the largest one being about 1.5 inches at the base. I grabbed a douche, I was familiar with it vaginally, but I'd never bought a re-usable one before, and we also purchased some more numbing cream called tushy-tamer as we were going to his place not mine that night.

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