Where it happened: My apartment on Valentine's Day
Langauge: English
Sex: Female
Rating: 8
Category: Straight
I had two first times, really. The first probably doesn’t count. I was about to start as a freshman in high school, and my older sister was going away to college. My parents drove her there and left me home alone so I wouldn’t miss the first day of school. The Saturday they left, I was enjoying my newfound, if temporary, freedom. That night, I couldn’t resist going through my sisters room, hoping to find something interesting she left. In the back of her closet, buried inside a large box, was an unmarked shoe box that was sealed tight with tape. I couldn’t resist the temptation, and I carefully opened it, figuring I could retape it and she would never know.
My heart raced as I saw the contents. There was a vibrator, a dildo, and several well-worn paperback books. The vibrator was pink, somewhat flexible, and had a pointed end. I turned it on and almost dropped it as it buzzed quietly. The dildo was huge and lifelike, at least so far as I knew. The tip even had a slit, the shaft had veins, and there were balls at the base. The books were romance novels, but much more explicit than the usual drug store variety. I stayed up all night reading them, feeling excited in a way I had never felt before. I felt wet and sticky between my legs, but I knew it wasn’t my period.
Dawn was breaking when I finally decided I needed to get some sleep. Although I was tired, my eyes wouldn’t stay shut. I took a hot shower, trying to relax myself, but as I washed my nipples and crotch, they begged for more attention. Now I had taken sex ed classes, so I knew the theory of what was happening to my body, but the reality was hard for me to accept.
I closed the drapes and climbed into my sister’s bed, pulling the blankets over my head. I caressed the dildo and the vibrator, rubbing them against my face. Before long, I had slipped out of my pajamas. Even completely covered, my nakedness increased my excitement. Holding my breath, I turned on the vibrator. I touched it to my face, then my chest. The shock of it on my nipples almost made me stop, but I kept on. I knew where I was going, but as I got closer, all those things I had been taught about sex echoed in my ears.
At first, it was just too intense for my tender genitals. I felt like I might have hurt myself when I touched it there, but after the initial surprise, there was no way for me to stop. I pressed the point against my virgin opening. Although I’m now sure only the smallest part of it was inside me (it was certainly less penetration than a tampon), it felt so big and deep, and the beating of my heart drowned out the buzzing. Then it hit me. It was more than I ever expected. I just froze, the pleasure flooding my body with a wonderful heat, seeming to last forever. When it began to fade, I instinctively moved the vibrator around, but that was too much, so I just pressed my legs tightly together, gasping for air.
I felt a little dizzy, like I was floating, and my mind was full of images from the books. I don’t remember falling asleep, but when I woke up, the batteries in the vibrator were dead. I didn’t get much sleep that weekend. School started on Monday, but I kept my sister’s treasures. Over the next year, I became bolder in my explorations, stretching my hymen until on my birthday, I was finally able to get that dildo inside me.
I was one of the “good girls” in high school. I was raised to say “No” to boys early and often. Over time, I would let them get to first base and second base. By my senior year, I would let my steady boyfriend Tom touch me between my legs. Sometimes, he would make me come, other times, I would pretend. I would play with his penis, and he could come in an instant, but I learned to tease him, making it last longer. He would beg me, but was glad I didn’t make him come until he couldn’t stand it any more.
After graduation, we broke up. We knew we were going to different colleges, but he really wanted to go all the way with me, and I still said “No”. I almost gave in once when I finally let him lick me, and that orgasm left me with no will to resist. Fortunately, he came while he was doing me, and I wasn’t even able to get him hard again.
I survived the summer and my first two years of college playing with myself and playing the bases with guys, never signaling them home. Some guys would call me a prude, but I kept the good ones happy with my creative hand work, and for special occasions, I would even suck them. Rob had been in the background for most of that time, always a good friend, sometimes an emergency date, and a couple of times, we went to my limit. But then I would meet someone else who seemed more my type.
The summer before my junior year was a disaster. I had to work two jobs, and had practically no social life. School that year wasn’t much better, as I had a several really tough courses. The only thing that saved me was that Rob was in most of my classes. We studied together, and found ourselves spending the little free time we had together, too. During Christmas break, there was a horrible plane crash on the news, and I thought at first Rob might have been on it. After a few frantic hours trying to reach him on the phone, I heard his voice and burst into tears. After that, I never thought of anyone else.
When we got back to school, I told him how I felt. He said he had been feeling the same way about me almost since he met me. No one else seemed to notice any change, but we told ourselves we were going steady. I told him I was ready to do it all with him, and he confessed that he, too, was a virgin. We decided to do it on Valentine’s Day. My roomate was going to spend the night with her boyfriend, so I made dinner. I think we were both nervous as we finished dessert, but Rob came over, took me in his arms, kissed me, and told me he would always love me. I told him I would always love him, and led him to my bedroom.
We undressed each other, seeing each other completely naked for the first time. As we got into bed, Rob wanted to kiss and touch every part of me. He saved my genitals for last, and as he lightly kissed my pubic hair, I told him it was my turn. I explored his body, surprised to learn how sensitive his nipples were. When I got to his penis, it was fully erect, and he gasped as I touched it. I kissed it gently, marveling at how it felt, warm, firm, and throbbing. I knew I was ready, so I ripped open a condom and pushed onto him (I had practiced with my dildo all week).
I laid on my back and Rob climbed between my legs. He was so gentle as he placed his penis against my vagina. At that moment, it felt so empty, but as he pushed into me, it felt so right to be filled that way. When he was all the way in, some instinct took over both of us. He started thrusting in and out and I raised my knees, opening myself more to him. He moved faster and faster, and it was a little scary, especially when my own body seemed to move with a mind of its own. I looked into his eyes and saw an intensity I had never seen before.
I heard him moan (only later did I realize that was when he came), and I was making sounds I’d never made before. I hugged him tightly, wanting to feel his weight on top of me. Rob’s body felt so hot, and mine was tingling, especially my crotch. My orgasm was so different, maybe it wasn’t an official one. It wasn’t the sharp “WOW!, whew, now it’s over” like when I masturbated. I felt so good for as long as he kept thrusting, wanting more, until he finally slowed down. It felt so perfect, I didn’t want to let him to move off of me, even though he was worried about me being uncomfortable under him.
I finally let him roll off me, and he got rid of the condom. We cuddled and kissed and caressed each other for a long time. We got engaged at the end of that school year, and had a big wedding right after graduation. But Valentine’s Day is still always a special occasion for us.
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