Nervous girlfriend shares first time anal experience

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For the next few months I kind of gave up. I’m just a tiny girl with a tiny asshole. Anal 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 ass bouncing up and down on top of his dick. I sat in reverse cowgirl and worked his cock 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 body released itself with pleasure.

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 orgasm 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 friends knowing full well what we would be doing that evening. It was hard to focus because I was so turned on by the taboo (in my mind) thing that we were going to do, but I had a couple 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.

When we got home I excused myself to the shower with a bottle of room temperature water and the douche and ran myself a warm shower. I put my hair up as not to get it wet and filled the douche to the brim. I squeezed lubrication on the nozzle and inserted it into my anus letting the water fill my cavity. I squatted in the shower and waited for my body to naturally expel the water. It felt like my backdoor was spitting. I repeated this as directed until the water was clear, and honestly until I felt clean enough to do it. Already I was feeling more confident going into my next sexual encounter with anal. I took some of the Tushy-Tamer and rubbed it both around and as deep inside my anus as I could. I wanted to give it a chance to work before it was time.

I sauntered into the room lit by a dull lamp wearing only my nightgown. Sam greeted me by slipping his hand under the lace and cupping my plump breast. He squeezed it so my nipples protruded out further before pushing the fabric to the side. He began sucking on my nipples. I love sucking his cock so I sat down on the side of the bed and slipped his boxers down to reveal it standing upright. I put one hand around it before taking it entirely in my mouth. I hit the back of my throat hard over and over again so it felt like it was about to bruise.

He pushed me further onto the bed and I lay on back pulling my knees up higher to reveal my anus. He took his thumb and rubbed inside my soaking wet cunt while he reached over to the nightstand where the three anal trained were lined up by size, waiting to be inside me. He went to grab the first one and I stopped him. It wasn’t much bigger than his thumb or my first butt-plug, I was sure that I would be able to take that one no problem and I guided his hand to the larger one. He looked at my like he was asking if I was sure and I nodded.

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