great friend to great lover

For 2 years, my best friend Caden had had a crush on me. I knew this, but never thought I could see him as being more than a friend. I was preoccupied with my boyfriend of 11 months. When I finally got tired of him, I became, again, preoccupied; with Caden’s best friend, Ron. The three months I spent with him were the months in which I lost my innocence. It wasn’t until after we had broken up that I finally lost my virginity to Ron, however. It wasn’t quite the fairy tale scenario most young girls picture their first time being.. Laying lifelessly on your ex boyfriend’s bed as he does little to thrill you while thrusting his half hard cock in and out of your dry pussy giving you road rash after a little while. I’d lost hope of sex being anything exciting with this experience.

Directly proceeding mine and Ron’s relationship, Caden and I started to become closer and closer. From the very start I had always felt the most secure in his arms, but I couldn’t imagine doing anything else with him. He was my sweet, slightly akward, and inexperienced best buddy. So I was thoroughly shocked the night that he pressed his lips hard to mine and began to explore my mouth with his tongue. At first I didn’t know what to think. It didn’t feel wrong, but I was a little nervous about the proceedings. I thought nothing could shock me any more, but he proved me wrong again. Before I knew it, I was laying on my bed with him stradling my hips and holding my arms above my head. Still massaging my tongue with his, I felt his hands begin caressing the curves of my sides and eventually making their way to my breasts. That was more than I could handle for one night.

Things like this continued to happen on occasion. Each time I became slightly more comfortable with the idea, but still unsure. I couldn’t say why I was so reluctant for so long. He wasn’t ugly. His body maybe not quite the epitome of perfection but certainly not repulsive. He had crystal blue eyes that never reflected anything less than love when they were focused on me. I loved playing with his soft mohawk of whichever color it had been dyed that week.

Over the months I couldn’t tell you what was happening to me. I was slowly, but quite surely, falling in love with my best friend. I would find myself with a vibrator shoved half inside of me and my mind wandering to him. For a while I felt very strange, but eventually, I let it consume me.

By the time summer came, I had let go of my hesitance. I wanted him. I wasn’t sure if I wanted all of him just yet. But I wanted to feel his fingers on my skin. I wanted to feel him teasing me and taunting me with playful fingers slowly building me up to orgasm. I was done wondering about these new feelings.

That summer I was leaving to go to Germany for a month. We took every oportunity we could to make out. I was shy to tell him how badly I craved his touch on my naked skin. I was sure that I would leave the counrty without the orgasm I so badly wanted. By some miracle, the night before my departure, we found ourselves left alone in my house. Before I knew what would happen, I had gotten myself wet just thinking about what I wanted.

I’ve learned now not to be surprised by the things he does, but that evening he had a very pleasant surprise in store for me. We were watching a movie on my couch in the dark when he pulled himself on top me and pressed me to the couch with his body. With his lips hard against mine, I felt his hand sliding slowly down my body. It came up underneath my shirt and began rubbing my breast. My nipples had already become hard with excitement as he began lightly twisting them between his fingers. Shortly after, his other hand began to run down my curves, passed my half missing shirt and down to my thighs. He began to rub the insides of my bare thighs which sent me into a fit of desire. I wasn’t expecting this. One by one his fingers found their way underneath my panties and began to circle my clit. My breath deepened as waves of pleasure washed over my body.

This was proving to be quite the send off for me. He released my lips and started kissing the length of my body. He tried to remove my panties, but I hesitated, worried about if my mom suddenly came home. And so I followed him to my room. I didn’t want to seem pushy because I knew he hadn’t done anything like this in many years. As it turned out, I didn’t have to do anything. He rested me over the bed with my legs hanging over the ledge, bent at the knee. I felt the fabric of my panties sliding off of my legs, replaced by soft kisses in my inner thigh. I was a little shy about having my vagina so plainly laid out for someone’s viewing, but was comforted by the darkness. He pulled me thighs apart and moments later, I was consumed by the sensation of his long tongue massaging and circling my clit. Occasionally he would take it between his lips and suck while flicking with the end of his tongue. Not long into this, there was a pressure inside my vagina as 2 of his fingers penetrated me, moving in and out with the rythym of his tongue on my clit. My breathing deepend and became louder and louder until the final moment of orgasm when a deep euphoria flooded my body and sent every muscle in my body into fits.

I spent a long 5 weeks in Germany after that night. I longed for Caden every waking hour. Luckily for us, it wasn’t long after my arrival home that I had the house to myself for a week. In the beggining I had no intention of spending nights with him, but, of course, he spent every night with me. Falling asleep in his arms and waking up to his adorable face.

I had done a lot of thinking during my trip. It was decided that I wanted to take Caden’s virginity. I hadn’t expected that time to come so soon.

We were laying in my bed one night. It was stormy outside. The rain continuously pounded on the window and bolts of lightning would illuminate every tree and hill for miles for a split second while the thunder shook the earth. As usual, we were tangled up in eachothers arms. I hadn’t yet done anything to sexually please him, although I wanted to. I rolled over on top of him and stradled his hips, making sure that his cock was conveniently placed between my legs. I kissed him long and hard ocassionally biting his lip. I could feel the blood rushing to his lower regions and pressing harder against my vulva. I began lightly grinding back and forth against his erection. I would give anything to feel that erection pulsing inside me.

I always felt we had some kind of unseen connection. We always were thinking similarly and I swear he could read my mind. Tonight would only further cement this. He mentioned to me that he had condoms in his wallet. So I rolled off of him as he removed one and slid it over his penis. Laying on the right side of the bed and looking out the window, my skin was crawling with anticipation. Then it happened. He was hovering over me, suporting himself with one hand, the other on his erect cock. He gave it a stroke or two so that it would be hard enough for penetration. He guided it to the entrance to my vagina. I trembled at the feel of his erection on my wet pussy. Then he slowly started to push it inside of me. The first few inches brought me a little bit of pain and I winced, but it was a good pain. When the entirety of his dick was filling me, he moved it back and forth and started the in and out motion. I couldn’t believe I had my best friend’s throbbing penis thrusting in and out of me.

At first, I didn’t expect to get much out of it myself, but within a few minutes, I was getting sensations I hadn’t experienced before. With each pass, I was recieving a very unexpected pleasure. Was I actually going to climax from this? I soon got my answer. Somehow we had coordinated our orgasms perfectly. As I was thrown in to spasmatic fits of pleasure, I felt him tense and knew he had just came inside me. Both of us were surprised at the success of this new act of intimacy and highly satisfied.

He had no experience, but somehow had brought me to screaming orgasm with his penis alone. My sweet, innocent best friend. I took his virginity, and we fell asleep in eachother’s arms that night, tired and in love.