I was really starting to suck Jim when he pulled his cock out of my mouth and proceeded to slap me in the face with it, which made me feel like a good little cocksucker. I sucked on Jim's cock for a few minutes until he told me he had a surprise for me, Jim stood up and stepped completely out of his jeans and walked towards his bedroom. I was worried about following him because I knew what could happen in the bedroom. When we got to his bedroom Jim showed me an outfit he wanted me to wear, it was a short red plaid skirt, matching heels and a black camisole. Jim told me if I wanted to be treated like a girl I needed to dress like one. I told Jim I wasn't sure if I wanted to wear the whole outfit, Jim told me it was too late to turn back now and gave me a whack on my ass which made my dick leak precum. Jim saw how much I enjoyed his spanking so he gave me a few more whacks. The amount of pleasure I got from being spanked was enough encouragement for to try on the outfit. After getting the heels on Jim wanted me to walk around a bit so he could see me in action. I pranced around the room while Jim stroked his cock shaking my ass for him begging for another spanking. Jim liked what he saw and invited me onto the bed. As I walked to the bed Jim grabbed my arm and threw me across his lap. Jim proceeded to lift up the skirt and spank my ass as I layed across his lap. After 10 good whacks Jim proceeded to play with my hole circling his finger around my tight hole. After about a minute of teasing me Jim started to put a finger in me, as I squirmed from pleasure and pain Jim started fingering me harder and harder. Jim pushed me off of his lap onto the bed, telling me he had another surprise. He reached into his bedside table and pulled out a dildo. I was a little scared and intrigued by what Jim was thinking, but before I could say anything Jim slammed his dick back into my mouth, as I was sucking him he started to tease my hole again but this time with the dildo. As Jim pulled his cock out of my mouth he asked if I was ready for toy, but before I could answer he slapped me in the face with his cock and put it back in my mouth.
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