Female • 16 years old • Rutherford, NJ
I was dating my first real boyfriend. He had a rep as a bad boy, which made me want him more. He was also a full five years older than me, and at sixteen, that's a big deal, especially to your parents. We'd been going out for a month and a half when my mom sat me down for "the talk." She insisted that guys were going to give me lines like, "I need to have it now," "If I don't get it I'll have blue balls," and "I'll leave you if you don't put out." At the time, I nodded right along and thought how stupid it was for guys to think that they could use such passé lines. They would never work on me.
 Illustration by Thomas Pitilli |
Until one day, when Bill was dropping me off, he used the one that struck fear into me. He said that we'd been going out long enough (a month and a half), and if I didn't sleep with him he would break up with me. Now to me, Bill wasn't just a regular guy. He was a twenty-two-year-old big deal, six-foot-four, with blond hair and blue eyes. I just couldn't see myself fumbling around in the dark with some half-wit at my high school, so I agreed. I thought about what my mom had said, but it didn't settle with me that it was just a line. He meant something to me. I wanted to do it right. At that moment, right after I agreed, my heart was in my throat. I looked at him sitting next to me in his car — at his body in his jeans, his flannel jacket, his big gentle hands as they gripped the wheel — and knew this was it. I was choosing him to do the deed, to turn me from a girl into a woman.
We arranged for "the night" to happen at his house. He didn't live in a household like I did, with two parents who gave a damn. His mom was an alcoholic who kept to herself, and his dad avoided her like the plague. I envied his freedom.
He went to a local drugstore and bought a pack of Trojans, and we went to his bedroom. I was so scared, and as he turned off the lights in the room, he left one on, casting a greenish glow. I took off all my clothes, and he slowly took off all of his. I had never seen his dick before, and it was huge. I touched it, and it was solid, veiny. Terribly frightening, like something out of a Stephen King novel. It grew of its own accord. Now, I wasn't stupid. I knew how reproduction and sex worked, and we had had plenty of makeout sessions, but things had never gone below the belt before. I looked up at him and said, "You're not putting that thing in me." I knew the first time hurt, but this was going to be agonizing. Worse than using a tampon without an applicator.
He smiled, kissed my head, and reassured me that he would go easy on me. Foreplay that night brought on an entirely different meaning — because this was definitely going to go somewhere! I was sick of being the last virgin among my friends, a subject of ridicule, and I kept hearing about everyone else doing it. It sounded so great, so cool, and I wanted to get it out of the way. I kept telling myself it was just a rite of passage. But as Bill's mouth reached my pussy to warm me up, tears slid down my face.
He looked up after a moment, and saw my fear. A sweet smile came over his ruggedly handsome features and he kissed my face, held me, and then put on the condom. I watched it all happen, detached, almost feeling separate from my body, so desperate to record this event in my mind. When he entered me, little by little, it hurt like hell. Worse than any menstrual cramps I had ever felt. I couldn't believe that I would ever come to enjoy sex as a whole. He reneged on the gentleness and thrusted into me more rhythmically, harder, and after awhile I stopped feeling the pain. Something had broken inside of me, and I became engulfed in warmth, wetness. He moaned and gave one last thrust, and I felt his dick pulsing in me. When he pulled out, we discovered the source of my pain relief. I had bled all over him and his sheets. Panicked because it wasn't my period, I cleaned myself up, while he removed the condom (which thankfully hadn't broken).
He wanted to do it again, but I refused. I was sore and scared, and just wanted to get home. He got angry with me, saying that "an experienced girl wouldn't have an issue with this" and that I was acting like a baby. I just lay there and cried, curled up on my side. This sure wasn't how I dreamed it would be. Then he apologized to me and held me — his guilt must've gotten the better of him. "I'm sorry. I forgot that for girls, it hurts a lot. Maybe I was asking for too much of you."
On the ride home, I felt different. Instead of a girl now, I was a woman. But what I really felt like was a scared kid who had gone too far with the wrong guy. He gave me a hug and a kiss, breathed into my tenth-grade hair, "Thank you," and I got out. After exchanging a knowing smile, I went back into the house. Instead of walking with my head held high, I came in slumped in confusion.
We're looking for stories about the first time you had sex. Email with 500-1000 words. (Don't worry, we won't print your name — but please do make sure to include your gender, where you were, and how old you were.) Submissions may be edited.
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