A Comforting Best Friend

I had never planned on losing my virginity that night, but this is how it all started. 

My life was perfect, never better. Everything was right and just how it was supposed to be, plus I had the guy that I thought was perfect for me. Kyle and I had dated for a year and a half now! Despite the fact I was so attracted to him with his athletic build, adorable face, and brown puppy eyes we hadn't had sex yet.

I wasn't in a rush even though every time I saw him I felt like running my hands all over his body. We hadn't done anything but kiss and I was content, although sometimes I felt Kyle wasn't. Kyle was 18 and I was 17. He was moving away for college this summer. I didn't understand why Kyle loved me so much, I never found myself attractive. I had long blonde hair that just fell into place everyday, and deep green eyes, small breasts and butt, but in Kyle's eyes I was "gorgeous".

In May the seniors got off three weeks earlier than the rest of the school. About a week after that Kyle asked me if he could come over to talk, and of course I said yes. When he came over he acted really strange, and finally told me that he wanted to take a break from our relationship so he didn't have to worry about cheating on me or doing something stupid. I didn't know what to do so I just told him to leave. I was crushed that he felt that way, and I didn't go to school for the next two days. My friends got worried, and texted me.

My best friend Tommy came over to see me that weekend. He was so comforting and sweet, he was completely different from Kyle. Tommy was beautiful, I just hadn't noticed until now. He was about 6'2: he was very strong, muscly, had messy brown hair pushed to one side just above his light blue eyes, and a smile that could make your heart melt. Tommy and I had been good friends since 9th grade and we could talk about anything, even our relationships.

Tommy didn't date very often, though he would ask me for advice. Tommy was normally single even though girls found him adorable. He was like a big teddy bear. Tommy rushed to my house when I told him Kyle had dumped me. I was so happy to see him as he walked into my room and hugged me.

"Hey, I'm so sorry Autumn," he said as I felt his strong arms grip me tightly.

"It will be okay," I replied sadly.

Tommy stayed for a few hours. We watched TV, laughed, and talked like normal.

He got up to leave and stuttered, "I really need to tell you something."

"What is it Tommy"? I asked concerned.

"Uh we had a really hard test in Anatomy," he said blushing.

I didn't know why he was acting so weird, but we hugged and he left. As school ended we had gotten even closer. We had hung out almost every day. He made me feel better and he made me laugh. Summer began and every day in June and July and August we would hang out, and do stuff together.

Tommy had a pool and one day in June I came over to his house in a very small bikini, not trying to catch his attention because I was still only into him as a good friend. I rang the doorbell and Tommy's giant and friendly smile met me.

We laid in the sun for a bit, tanning out bodies. Then he asked if I wanted to go swimming, so I agreed. I noticed Tommy blushing. I looked at him and he started turning to walk to the pool. I had noticed his swim shorts twitch and a big bulge form. I just ignored it, and figured he was day-dreaming about some girl.

Tommy quickly jumped into the pool and so did I.

"I'm having a good time with you Autumn," he said smiling.

"Me too, you really know how to cheer me up."

Tommy swam over to me and picked me up above the water. I felt his strong hands tickling my sides, and I couldn't stop laughing. Tommy dropped me in the water, and I felt his body against mine. He still had a bulge in his shorts and he quickly swam back under water. I got out of the pool and the day went on like the rest of the summer had gone.

Tommy and I had gone to the movies, the zoo, shopping, a concert and everything imaginable. I was still too naive to realize his feelings for me.

It was the end of August and one night Tommy's parents, and brothers were out of town for the weekend. I came over to watch a movie with him and chill. I rang the doorbell and he answered wearing sweatpants, and a tight fitting Nike shirt. He had a huge grin and swept me off my feet like he hadn't seen me in weeks, even though we had just seen each other yesterday.

Tommy's hair was wet, and he smelled really good so I figured he had just showered. We picked a movie, put it in, and he flopped out on the big couch with the best view. I sat on the opposite couch but about 10 seconds later he told me there was enough room for me so I could actually see the movie.

I laid next to him with my back to him. I could feel his breath on my neck, and feel his body. He put an arm around my waist, and I could feel all of his muscles tense up. I could smell his cologne, and again feel his bulge in his pants. I couldn't help it; I was getting wet, and I didn't know what to do.

The past few weeks feelings started to grow. I finally noticed how genuine and sweet Tommy was, not to mention his god-like body.

The movie finished and I got up about to leave, but Tommy insisted that I stay for a while longer. He smiled but then sighed loudly and said, "Autumn, I have to tell you this, it's killing me. I've been in love with you for going on two years and I have wanted to be your boyfriend for so long. You are the best person I know. You're so sweet and kind, you have the best personality, you make me smile, you're smart and you're so sexy," he finally finished. 

I was completely red, and not expecting that at all. "Why did you wait so long to tell me?" I asked.

Tommy reminded me I had had a boyfriend for almost 2 years. "Do you feel anything for me?"

I thought about it for a minute and realized I had to respond. "Yes, you have been so good to me and such a good friend, I think I love you, too," I replied.

Tommy smiled and slowly walked over to me and kissed me. It was the softest kiss I had ever felt, he had soft lips and soft hands that held the back of my neck. He pulled away and looked at me. "You have no idea how long I have wanted to do that," he said laughing.

I grinned and kissed him back, and after a few minutes he led me to his room. I had been in his room probably a hundred times but something was very different this time. Tommy's kisses were incredible, his tongue was soft and warm and gave me butterflies. He smiled at me more seductively, and sat on the end of his bed. I followed him and blushed.

"Are you a virgin?" he asked me.

"Yeah," I said nervously.

He smiled and chuckled. "Me, too. I haven't done anything. Don't be embarrassed, I have been waiting for the right girl," he said softly. "Do you want to stay here tonight? 

I grinned, kissed him, and said yes. Tommy's eyes lit up and he playfully pounced on top of me, kissing my neck gently and slowly. I moaned loudly and he laughed and kept doing it.

"Do you find me sexy?" he asked curiously.

"Yes, you have the prettiest eyes and the cutest smile ever, not to mention your body," I answered teasingly.

"Do you find me sexy?" I asked mockingly.

"Yes," he responded. "Everything you do is sexy and your body is too. Are you sure you want to do this?"

I smiled and said, "Yes."

Tommy got a serious look in his eyes, and slowly pulled up his shirt, then mine. I was wearing a bright pink push up bra and little lace panties that matched. I was so glad I wore these rather than my normal tan bra, and random panties.

I looked up at Tommy wondering if he liked what he saw. His eyes widened and he quickly removed his sweatpants and then my jeans. We were both in our underwear staring at each other awkwardly, even though we had seen each other pretty close to naked every day this summer.

Then he began to kiss me again. I could feel his whole body against mine, trapping my small body underneath his. It felt amazing. His hands slowly explored my body, he unclasped my bra, letting my small perky tits spring free. I could feel his penis keep growing bigger as I finally slid his boxers down.

"Wow, that's big," I said without thinking how dumb I sounded. I couldn't stop staring, intimidated. It was at least 8 inches and really wide.

We both laughed and I could help the urge, I reached out gently and touched it just out of curiosity. It was rock hard and just at that one touch Tommy moaned loudly and shuddered. He kissed my neck slowly moving down lower to my belly. Tommy's cold hands ran down my sides, slipping my panties off. He hardened even more when the little lace panties revealed how smooth I was.

"I'll be right back," he said jumping up, and rummaging through his bathroom.

He came back out with a condom on and laid on top of me. He asked once again if I was comfortable. I nodded and smiled. He kissed my forehead and asked me one last time if I was positive I wanted to do this.

"Yes Tommy, please just be gentle," I said shyly.

"Of course," he said.

Tommy slowly started to push into me. It was a struggle and painful. After several minutes he finally pulled himself into me. My eyes were filled with tears and I was squirming at this new feeling in my body. There were juices running out of me, and going everywhere. I couldn't help it, I had never had this happen before.

"How do you feel?" Tommy whispered in my ear softly.

"Good," I said as he wiped the tears from my eyes. I felt my hymen break, and I moaned in pain.

"I'm sorry," Tommy said as he stared into my eyes.

After about ten minutes of slow pain a new feeling began. Shivers started running down my spine. Tommy began to move faster and I could not control the soft moans escaping my mouth.

"Ohhhh, Autumn, this is amazing," moaned Tommy, his eyes rolling back into his head as my hips moved with his.

I guided his hands to my breasts, and he massaged them slowly, never losing deep eye contact with me. His hands were warm and big. He slowly began to go deeper every time and faster. He started to shake and grabbed hold of my shoulders as he came.

Tommy had the biggest grin I had ever seen him have. He started again losing his gentle side. He smiled up at me with his sky blue eyes and long lashes and began to pound me, still with difficulty from tightness. I gripped his strong arms tightly to hold on as he rammed my tiny opening. He teased me, and then finally let me reach my climax.

I screamed loudly with pleasure, my toes curled up and my whole body started to shake. He continued to kiss my neck and finally pulled out slowly. He fell down to the side of me out of breath, and rolled over. He wrapped his big arms around me, staring into my eyes. I had never felt so safe and secure in my life.

"I couldn't have asked for a better first time," he said softly kissing my forehead. "I love you so much."

"I love you too," I replied sleepily.

Tommy held me in his arms and we fell asleep intertwined.