Beginnings: My First time as a crossdresser (PT 1) - Sex Stories

Beginnings: My First time as a crossdresser (PT 1)

... just like Michelle had done with me so many times before. I tried to roll it down over his cock but it wouldn’t roll down. Eventually I figured out the condom was facing the wrong way and took it out of my mouth and just rolled it on with my hands. So much for my ultra smooth seduction moment! After I got the condom on him I climbed up on his lap and straddled him, I spit into my hand and lubed up my ass with my saliva and lowered myself upon him. There was a lot of resistance at first but finally the head of his cock slipped inside me. My eyes flew wide open as the pain was pretty intense at first! I held myself there with just the head of him in me and waited until the pain gradually subsided. Slowly I lowered myself down on him pulling back up only to slide back down a little deeper each time, eventually I had all of him inside me and loved the feeling. It was hard but not rigid and unyielding like the toys I had played with before, plus it was warm and velvety. It only took a few moments to decide I loved it. I slid ...

... up and down on his cock loving the way he felt in me increasing the speed of my gyrations. After awhile he grabbed my ass and stood up leaving me impaled upon his awesome dick. He gently lowered me down on my back on the carpet next to the fireplace. Putting my legs over his shoulders he started thrusting into me, slowly at first. Soon his tempo increased and he was fucking my ass like a jackhammer. The feeling was incredible! I felt a slow burn starting deep inside me building to a raging bonfire. I knew then that I loved being a girl and taking a man’s cock deep inside me. In that moment I felt completely like I was a female and born for this glory. After what seemed like hours but was entirely too short of a time Tracey cried out thrusting hard into me and collapsed on top of me. After a few minutes he straightened up, sliding his limp cock out of my sensitive ass. “That was great Baby” he whispered “Was it worth the walk?” “Definitely” I replied knowing I would find a way to do this again and the sooner the better!