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I met a new guy that I really connected with, and we were meeting almost every day to just hang out. For the first week or so, we did a lot of heavy making out, but we both knew it was time to take it to the next level. So, the next time he came over, I was in a super sexy tight mini, black thigh highs with lace at the top. For an added touch, I wore my pink heart locket tied together with a light pink ribbon. I walked out of the bedroom after getting prepared for Mike who was patiently waiting on the couch, he was all smiles. After another heavy make-out session I helped him remove his pants and shoes but left his underwear on. We kissed some more, and I climbed on top, so I was straddling him, and we started making out even harder. His hands were running all over my body and I started grinding against his hard cock. He had one hand on my back, and another was gripped my ample ass cheek.
Mike was holding me, and he kept telling me how fantastic I looked and smelled. It was so hot, and I was getting very turned on. Slowing unstraddling off his lap, I knelt in front of him, took his underwear off and sucked his cock like it was the best cock in the world! After a while I straddled his lap again and knew it was time to have him inside of me. The further we had gone before was letting Mike finger my sissy hole, now I was whispering his ear that I wanted him to fuck me. By the hardness of his dick, he was ready to start pumping. He grabbed the lube on the end table and poured it on his cock, and I leaned forward so he could better lube my asshole. I scooted up and carefully helped him work his cock in me.
His cock was bigger than most, and it took a few tries but we finally his thick meat in my gurly hole. The pain was much worse than I expected, I thought I was ready for him, but I misjudged the size of his cock. I could only fight through the pain and take it very slow. The pain didn't get any worse as I lowered myself further onto his cock, but once I was all the way to his balls, I really felt him in me. Mike was great the whole time, supportive, taking it slow, and eventually most of the pain passed and I liked how it felt to have him inside of me. I rode him back and forth for a bit, and he grabbed my hips while thrusting in and out. It was almost overwhelming, so I grabbed his shoulders and hung onto my man to catch my breath and we started making out again.
Mike wanted to change positions, so we headed to the bedroom where he placed me flat on my back at the edge of the bed so he could stand over and fuck me. After rubbing more lube on his cock, he pushed my legs back and punched through my asshole again. He was slowly thrusting in and out, complimenting my body and telling me how amazing it felt to be inside me. I wanted to both, pull him closer because I loved what he was doing to me and push him back because he was wrecking my poor sissy cunt. He started thrusting harder and moaned so loud I thought my neighbors would start knocking on the walls. I was sweating and moaning, he was pumping so hard, then with a few last thrusts I felt his cock pulsate and even that was a bit painful. He unloaded every ounce of cum stored in his hairy balls. It was dripping out of my ass, and when he pulled is cock out of me, he wiped his slick cock on my sissy balls. Mike was so smooth, that man convince me to do ANYTHING. It hurt but the rush of pain and pleasure made me want his so much!
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