First Time 90

I had never really given sex much thought. See, I am very shy and led a very sheltered life. At least, until I met him.

We had met online, on one of those message boards. I can't remember why, but we had started talking and he sent me a message introducing himself. Out of boredom, we started chatting. Soon we became fast friends, and a few months after we started talking I realized that I had a crush on him.

We had been talking about me coming to visit for a while, but as far as I knew, it was only a joke, despite the fact that I'd love nothing more than to meet him. Some time later, I told him that I liked him....and was shocked to find out that he liked me, too. We continued talking, and soon we fell in love. This time we began making plans to meet for real. It was tricky to play -- I'm only 19, and we live a considerable distance apart. But finally, I found myself boarding a plane to be with him.

I arrived at the airport, and there he was, waiting for me. I wanted to rush over and hug him, but my shyness gripped me and all I managed to do was smile and say hi. One of his friends was there as well, and she drove us to his house. He helped me with my suitcase and invited her in, but she declined, saying she had work to do. Together we dragged my suitcase up into the guest bedroom, and then he invited me into his room.

I entered timidly and took a seat on his desk chair; he hopped on the bed. We sat like that, chatting idly for a while...or rather, he talked while I occassionally replied. I think that over a course of three hours I said about ten words. We watched some TV together, and I knew he was trying to relax me and put me at ease; he knew all about my shyness and knew that I was very nervous. Finally, he clicked off the television and pushed his bedroom door shut all the way. He took my hand in his, and looking me in the eye, pulled me gently off the chair and onto the bed next to him. He held me in a tight hug, and there we sat for about 10 minutes.

"I've been waiting months to do this..." he whispered into my hair. I smiled, and finally he let me go. He held my face in his hands, and looked me straight in the eye. I could feel myself melting in his gaze -- there was no mistake, I was truly in love with him. I smiled tearfully, but they were tears of happiness. Slowly he brought my face towards his until our noses were touching, and then we kissed.

As I said, I am very very shy, and have been very sheltered. So much so that at the age of 19 I was still a virgin. I had never even been kissed by a guy. But when I felt his soft lips touch mine, what felt like an electric shock flowed through me. We kissed several times, then he lay me down on his bed and lay down next to me. We lay on our sides facing each other, gently kissing, while he rubbed his hand over my stomach. He worked his hand upwards to caress my breasts, and then down between my legs. I was wearing jeans but still could feel his touch, and he grabbed at my crotch. I jumped slightly, and he smiled.

"Like that?" he asked. I simply nodded in reply. He smiled again, and rolled me over so that I was flat on my back. He lay on top of me and continued kissing me all over, his mouth working down my neck to my chest. I giggled as the kisses tickled me, and he laughed in return. Soon I felt him pulling my shirt up; I lifted my arms and it was gone. He lifted me off the bed and reached around to unhook my bra, which joined my shirt on the floor. Still straddling me, he gazed down at my breasts.

"So lovely..." he said. I blushed; no one had ever seen me without a shirt before. He caressed them softly, first my left and then my right, and then leaned over and started kissing them. He planted his lips all over my chest, before he looked up at me, eyes twinkling. Then he licked my nipples, which made them instantly turn rock hard, and he took them, one at a time, into his mouth and gently sucked on them. My back arched underneath him; I had never felt such a sensation before and it felt incredible. I could feel myself starting to get moist in excitement.

"Now...lets get rid of these..." he said, rolling off me and looking down at my jeans. He swiftly unbuttoned and unzipped them, and in no time they were off, leaving me in just my panties. He laughed when he saw them. "You cheeky little minx!" he said; that morning I had chosen to wear my pink panties that had two large cherries on them. I don't know why, but something had told me to do it. I lifted up my ass, and he deftly peeled my panties off and tossed them to the floor where the rest of my clothing had been deposited.

I was now completely exposed. No one had ever seen me naked before, and my face was flushed bright red. But the embarassment soon gave way to excitement. He paused only to whip off his own clothing, and then he was laying next to me on the bed again. He rubbed my stomach and my tits while kissing me all over, and once he judged that I was nice and turned on, he slowly brought his hand down. He began fingering my clit, softly at first. He worked up the intensity for a few minutes, and then got up and moved down and leaned between my legs. He slowly and gently pushed them apart, and lowered his face towards my pussy. I gasped with pleasure as I felt his tongue snake across my most private parts; he used his tongue to work my clit until I was soaking wet. After a while he went back to using his fingers, and began kissing me all over. With one hand he rubbed and tickled and kneaded my clit, with the other he stroked his cock until I could see that his erection was rock-hard.

Suddenly he was on top of me, shoving me legs apart. I knew what was going to happen and even though I very much wanted it, I was very nervous. He was larger than I thought and I'd heard that having sex for the first time was painful. I was incredibly tense and nervous, and I'm sure he could see that. I tried to clamp my legs back together, but he had already positioned himself between them and was leaning over me. I squeezed my eyes shut as I felt his cock touch my pussy...and then gasped sharply as he pushed it in. It hurt terribly, even though I knew that he was going slowly and trying to make it as painless as possible for me.

"You okay?" he asked. I nodded, wincing. It hurt, but I didn't want him to stop. He slowly thrust into me; I winced and gasped each time because of the pain, but he could see in my eyes I wanted him to continue. However, he stopped before he was completely finished.

"What...?" I asked quietly.

"Don't want to overdo it..." he replied, pulling out of me and kissing me. He went back to fingering my clit, while with his other hand he masturbated himself, quickly bringing us both to orgasm. We lay next to each other, and he grabbed me in his arms and held me tightly against him. We were silent a moment, until I spoke.

"When can we do that again? And this time, can we do it harder?"