Her name was Andrea and we had been dating about 6 months. We had done everything else and one night, while I was feeling her up on her sister’s bed, I told her I wanted to make love. She surprised me by saying yes. We had no protection, but I promised not to cum in her. We started with me on top and all I could do at first was slide up and down her slit. That in itself felt wonderful, but I wanted to get in there. I had used 3 fingers in there before, but I am a bit girthy down there, though only 6 inches long. She was always so wet that we had plenty of lubrication.
We shifted a little and it started to go in, but it was way too tight. As I pushed harder she would scoot back in pain and then apologize and we would try again. She was set on being on the bottom for her first time, but she kept scooting away from me and I was getting frustrated. I got my cock’s head in and that was as far as I could go. She kept jumping off when the pain would hit. I suggested we switch to her on top. She was still way too tight. I loved the way her breasts were right there for me to play and suck on. She had perfect 34C and was 5′ 7″ tall, so we were face to face and it was divine. I could move back and forth a little and it really turned her on. That turned me on and I would stop us when I felt myself about to cum.
We kept wiggling me in farther and farther. Stop and go. I knew I had to be dripping into her, but I did not tell her. She was terrified of getting pregnant and we had no protection. I had to promise not to cum in her, but I knew I had been dripping for a long time. After about 10-15 minutes, I started rocking my hips back and forth. While about a third of the way in, just moving that much and not pushing in more and she just started moaning OOOOOHHHHHH. She was really liking it and I knew she was about to cum and I couldn’t hold back. I told her I was cumming and she jumped off so fast. I honestly did not think she would get off of me. I had one extremely large contraction and the largest amount of semen I had every and have since seen squirted onto my inner thigh in one large plop.
She felt her pussy to see if there was blood, but if there was, the large dripping mess had washed it away. She went to clean up in the bathroom and we made out the rest of the night with some mutual playing. That was the first and last time we tried it. We kept to the mutual masturbation and oral sex that was so fulfilling for us. She would always have multiple orgasms and I still love the way I could get her off.
I was a first in many ways for her. I was the first man to see her naked, the first to eat her pussy, the first to finger her, and the first to give her an orgasm. She was my first in those things too, so she will always have a special place in my heart.
Side note: she had the most interesting bush of pubic hair. It was silky soft and at the top of her slit was an extra thick clump of hair that had to be 5 times thicker than the rest. I don’t recall ever seeing it like that since on any other girls. It was so fun to twirl when I played with her.