First-Time Sex: How I Lost My Virginity
I have already written about two of my personal sex experiences on this blog, My First Anal Sex Experience and My First (Surprise) MFM Threesome, but not about a major milestone in every girl’s life, losing my virginity. It seems a long time ago now, but it’s not something you ever forget.
After Christmas break of my freshman year of high school, a senior boy asked me out. I’ll call him “Jason.” Jason was good-looking and popular, and being asked out by him was a major boost to my self-esteem. I was embarrassed by my Russian accent and still felt socially awkward and out of place. I even went by Lana back then, to seem more American.
Being asked out by a popular senior boy was also a boost in my status among my friends. They tried to get even by warning me that older boys expected sex from girls they dated.That did give me pause. I was no stranger to fooling around with boys, but my sexual boundaries didn’t extend that far. I had gone as far sexually as being felt up by a hand inside my panties, but up till then, only my bra had come off, never my panties. That would change soon.
Going out with Jason was everything I imagined it would be and everything my friends warned me about. He took me to a party at a senior cheerleader’s house. A lot of older boys and girls whom I’d seen around campus, but didn’t know, were there. Jason introduced me to all his friends and almost never left my side. Everyone, except for a few of the girls, was really nice to me. It was one of the most fun nights of my life.
That night also began Jason’s assault on my virginity. It started at the party when we kissed and he slid his hand inside my top, and continued at his house after the party. When we got there, the house was empty. It wasn’t long before Jason was pushing past all my previous sexual boundaries. Not only was my bra off, but so were my panties, and not only was there a hand between my legs, but Jason had stuck a finger inside me, too!
That kind of snapped me out of my sexual trance. I said I had to go home. Jason laughed and asked if it was past my bedtime. His insinuation stung, but I insisted my mother would kill me if I didn’t get home right away. “I thought you were cool,” he said. I promised that I’d make it up to him, but that my mother would ground me if I got home too late.
“At least jack me off,” he replied. “All girls do that.” I never had, but I thought I knew how. It turned out I was wrong. He kept telling me to do it harder and faster. Finally, he came – all over my hand. It was the first time I’d made a boy ejaculate (that I knew of). He took me home after that.
Jason didn’t call me the rest of the weekend. When I saw him at school, he was friendly, but a little distant, it seemed to me. I worried that he was going to dump me after one date! That wouldn’t do anything for my new-found status – or my self-esteem. Plus, I liked Jason and liked being with him. When he wasn’t trying to have sex with me, he was really fun to be with. Actually, his trying to have sex with me wasn’t bad, either. It was just such a big step to take that it scared me.
I decided that I needed to grow up. If Jason wanted to have sex with me, that was sort of a compliment really. He was the best boyfriend I’d had up to then, for looks and popularity. I was going to have sex eventually anyway. If Jason still wanted my virginity, he could have it.
I demonstrated my new maturity by hanging around Jason like a puppy dog as much as I could. I even went to his basketball game and cheered wildly for him every time he touched the ball. That must have given him the idea that I’d had a change of heart. He asked me after the game if I wanted to come over to his house and hang out. I said sure.
Jason hadn’t said that his parents weren’t home, but I wasn’t surprised to find that they weren’t when we got to his house. I had crossed the Rubicon. I wasn’t leaving there a virgin.
Just like after the party, it didn’t take long for us to be in his bedroom making out. I was soon completely naked with Jason down to his tighty whities, and just like before he had a finger inside me. This time it excited me instead of scaring me, though. I saw the bulge straining the front of his briefs and decided it was time.
I lay back on the bed and let my legs fall open. That was all the hint Jason needed that I was ready. He pulled off his briefs, got a condom out of his nightstand drawer, and put it on. That made me feel a lot better. I had thought about condoms, but where was I going to get a condom? It was a huge relief that Jason had one. Now I was really ready.
Jason climbed between my legs. “It’s my first time,” I said. “Don’t worry. I won’t hurt you,” he answered. That turned out to be a lie.
Jason positioned the head of his penis at my opening. I was practically shaking from fear and excitement. Then he pushed in. At first it wasn’t so bad, but when he pushed further inside, it started to hurt. It really hurt. It felt like he was pushing against something solid, like something was ripping inside of me. I must have winced or cried out, because he stopped and asked if I was all right. “It hurts a little,” I lied.. “I’ll go slow,” he promised.
I can still remember when it started feeling good. For what seemed like the longest time, I just lay there wanting it to be over, then it started feeling good, then it started feeling really good – and then it was over. Just as I was beginning to enjoy this amazing feeling, Jason thrust hard into me several times, lay still for a few moments, and then pulled out. It was definitely over, and so was my life as a virgin.
I went to school the next day, and I must have been wearing my I’m-not-a-virgin-anymore smile. My friends surrounded me and pumped me for all the details. Jason didn’t dump me after “popping my cherry,” either. We went out for the rest of the school year and all through the summer until he went away to college.
I experienced a lot of sexual firsts with Jason. Besides giving him my first hand job and my virginity, I also gave him my first blow jobs. Sex got better, too. I began having orgasms. Jason even went down on me. Losing my virginity to Jason really jump started my sexual life. I have a lot of sweet memories of our time together.