My first time was with my college roommate. We flip fucked my first time. We were both 20 at the time. We had been experimenting with oral sex for about a month. Probably sucking each other half a dozen times. Swallowed my first load of cum from him the night before this event. We were always escalating our experimenting and exploring. Like I said the night before I sucked him to completion and he fell asleep in my bed. We were both naked when we fell asleep.
Waking up in the morning I felt him behind me. He had my cock in his hand slowly stroking me. But I could feel his hard cock between my legs and the tip of his cock rubbing my balls as he rocked back and forth simulating fucking me. My balls felt wet with precum from his cock. I pretended to be asleep and leaned in a little and pushed back to his cock stroking between my legs. This opened my ass a little bit and I felt his shaft rubbing against my hole. This let him withdraw a little and rub his cock head against my virgin ass. Now his precum was on my tight hole. It made me moan. He knew I was awake then. He whispered gently.... “I want to fuck you. Can I fuck you?” I looked over my shoulder and said yes.
He bolted out of bed and went to his room, hard cock swaying as he ran and came back with some lube he uses with his girlfriend. He got behind me again and rubbed some lube all over his cock and tried to push into me, but it hurt too much. I asked him to put some lube inside my ass. I felt him push one then two fingers in me and worked them in and out. He tried his fat cock again and it hurt again. So I go him to lay on his back, pushed some lube into my own ass and applied more to his hard cock. I straddled his cock, I could feel him shake with anticipation, this was the first time for both of us, my cock was as hard as it has ever been and I lowered my tight little virgin hole slowly on his cock. Taking my time, gently in and out until the head of his cock popped into me and it hurt, I held still until I felt I could move. I slowly pushed down on his cock, gently and slowly. The whole process took about 20 minutes of patience, then at one point I realized I had him all inside me and I sat still. I rose up only once and lowered down again slowly and it felt SO good I came all over him.
I relaxed for a minute and I felt him start moving slowly, I noticed my ass was relaxed after my orgasm and I began to ride him. He lasted less that a few minutes but when he held onto my hips and thrust into my ass hard and I felt a man cum inside me !!!!! It made me cum again!!! We went to the shower and played around and he begged me to fuck him. That was my first time!!