Juicy Jamie Shares Her Second Anal Adventure-Exit Only Part 2

At age 10, I mastered how to finger my little asshole. If you are curious about that, read Exit Only-Juicy Jamie’s Anal Adventure Part 1! After that first sweet release, I knew that I had to explore my asshole even more. I treated my butthole much like I treated my pussy. I saw it as another hole to play with and to stick everything I could get my hands on in it!  However, this adventure is not about self exploration, it is about the first dick that pushed it’s way past my tiny entrance.

I was 18 and fell in love. My views on anal sex hadn’t really changed all that much. Yeah, I liked sticking fingers in when I wanted to feel extra naughty but actually letting a boy put his meat inside that hole? I was scared and wanted nothing to do with it. My boyfriend decided that because I kept saying no, that he needed to sit me down and explain to me why he felt so strongly about having anal sex with me. Looking back on the situation now, I know it was all a manipulation, but I digress. He told me that he had only done it once before and the girl hated it but that he had never felt so much pleasure in all his life. I decided that because I loved him so much, that I would let him fuck my ass.

He had moved into a new place together and had no furniture. We had a picnic in the middle of the apartment floor on a blanket that he laid out. After dinner, he put the dishes away and gave me a full body massage with baby oil. The massage felt so great that I needed him inside of me. I told him to fuck me. He penetrated my pussy with a force like never before. He pounded me hard until I exploded all over his dick. When he slid out of me, what felt like an entire cup of juice flowed out of me and drenched that entire space from my pussy hole down to the blanket. He took that juice in his hand and began rubbing it in little circles around my butt hole. When he slid his index finger inside, it felt like two of my fingers. “It hurts.” I pleaded with him to slow down and he did. He grabbed my hand, placed it on my pussy and told me to play with my clit “it’ll make the pain go away,” he said. Rubbing my pussy was the last thing on my mind but I complied.

Heat started to build up inside of my pussy hole and it suddenly felt too empty to handle. I started to finger fuck my pussy hole while he finger fucked my ass hole. I could feel his finger pumping in and out between that thin piece of skin separating my holes. It was so hot that I quickly came again, squirting so much pussy juice that it soaked through the blanket entirely.

He took the tip of his dick and slid it up and down my slit until it was poking the entrance to my asshole. An excruciating pain stabbed at my hole while he pushed his way in. He went as slow as he could but my hole was just too tiny for him. “Rub your pussy again,” he said. “My arms are tired,” I told him. Because we were unpacking and hanging pictures, there were boxes and tools everywhere. He picked up this hammer and turned it around. He lined the handle up to my pussy hole and just started rubbing it up and down and then popped the handle right inside of me. He slowly fucked me with the hammer while he tried to get his dick inside of my asshole again. As he thrusted forward, I could feel my asshole finally relaxing and spreading for him. When his dick head was entirely inside of me, I could feel his ridge digging into the smooth walls of my hot asshole. It hurt but the feeling of being totally filled up is like none other. That space inside of me was taken up so much that every time he thrusted into my asshole, I could feel that hammer push up against my g-spot and it felt so delicious that when he asked me if we needed to stop, I begged him not to. Want more details than this?