Our First Time Together

As Ashleigh and her friends disappeared into the crowd at the mall, my buddy walked up with his girlfriend, April, and her friend that they introduced as Michelle. The first thing I noticed about her was her breasts, it was everything I could do not to just stare at them. She was about 5’-7” with long legs, curly blonde hair that came just below her shoulders. She was wearing loose shorts that came down mid-thigh and a tight t-shirt that accentuated those breasts. She had beautiful eyes, a cute nose and a pouty lower lip that she bit as I said hello. We talked for a minute and then headed into the arcade to play some games. I didn’t play any and just spent the entire time watching her. With her focused on the games, I was able to really check her out and I liked everything I saw. After the games we all went and got a slice of pizza. Michelle and I got a table to ourselves and we spent the next hour or so talking. I found out that she was a little younger than me, although she didn’t look it, and went to a neighboring school. I really liked her and decided to just go with and see how things worked out.

We talked on the phone every night and the next time we met at the mall, I asked her to be my girlfriend. Things were still kind of awkward as we were getting to know each other. After my experiences with Rebecca and Ashleigh, I wanted to take things slow because I really did like her and didn’t want to do anything to scare her away. After a few dates, I still had not kissed her, mostly because my buddy and April were always there but also because I seemed nervous around her. Thinking about the things I had already done with two other girls; I couldn’t figure it out and I could tell she was getting frustrated. Looking back, I now know that I was nervous because she was different, and I already had feelings for her. We finally had a date without them and before I left, we were standing in her driveway talking. I was looking into her eyes and don’t remember what she was saying, only that it was time. I took her face in my hands and kissed her. She responded by putting her hand behind my head and pulling me close to her. I leaned her against my car and pressed our bodies together while our tongues probed each other’s mouth. She felt great up against me and I could feel her plump boobs pressed against my chest. I’m sure she could feel the bulge in my shorts pressing against her as well.

That first kiss led to making out in my car every time I saw her. That winter, things were getting serious between us and so were our make out sessions. One night I got the nerve to touch her breast and she didn’t stop me. Her breasts were plump and firm C cups and just a bit more than a handful for me. Touching her breasts was certainly different than Rebecca’s. That first year seemed to fly by and as the school year was coming to an end, our feelings for each other had grown. Making out with the light petting had turned into touching each other sexually. I had begun fingering her pussy and she was rubbing my dick now every time we made out. We never seemed to be alone except when we were in my Honda so we were limited as to how far we could go in two seats. She would lay back and let me run my fingers up her shorts. At first, I just rubbed her through her panties, but it didn’t take long before I found my way into them. Her pussy was always soaking wet and my fingers slid in easily. She went straight for it the first time she rubbed me and the feeling of her hand on my cock drove me crazy. I always stopped her before I came though. Cumming in my pants would have just made a mess I didn’t want to have to go home with. When I got home though, I would always jack-off thinking about her touching me.

We had been together for over a year now and the Honda had been replaced with a Nissan pickup. I was now on the lookout for remote locations where we could park for a while and be alone. I kept a blanket behind the seat that we would lay out in the bed of the truck and our heavy petting quickly turned to oral sex. I had tasted her pussy on my fingers many times but the first time I licked her pussy was amazing. It had been a long time since that night in the tent with Rebecca and I had been longing for this. I couldn’t get enough of her; the scent of her sex drove me crazy. I ran my tongue between her lips tasting all of her, allowing it to be covered with her juices. She rubbed my head and really enjoyed what I was doing to her. I loved eating her pussy and couldn’t get enough of it. After several minutes, I noticed her soft moans getting much louder and her breathing getting heavy. She grabbed my hair and pulled me hard against her so that her whole pussy was in my mouth with my tongue licking her clitoris in a fast-circular motion. It was just a few seconds later that it happened, and I didn’t think she was going to stop. She moaned loudly, her body tensed and then shook. Her back arched and she pulled at my hair. I didn’t think she could have but she got even wetter and covered my mouth with her warm creamy juice. She tasted so good! When she finally relaxed, she let out a deep breath and whispered, “Oh my God”. I don’t know if it was her first orgasm, but it was a good one and she acted like she had been needing it badly. I remembered Rebecca telling me she had made herself cum a couple times by rubbing her clitoris, so I guessed Michelle had probably done the same thing. After all, I jacked off all the time so I figured she must too. Still this really seemed to give her some much-needed relief.

I on the other hand, came quickly the first time she sucked my cock. The feeling of me in her warm mouth was more than I could stand and after only a few short minutes of her licking my shaft and sucking on my head, I erupted into her throat. I’m wasn’t sure she knew what to expect and the amount of cum maybe caught her by surprise but as I filled her mouth, she began swallowing it like she had craved it. I guessed she had done that because she didn’t know what else to do but I would later find out differently.

We kept that routine up for weeks with both of us wanting more. I had become good at making her cum with my tongue and she was fantastic at giving me head. We had become very close and ached to have sex. It was now the fall of my senior year. We had been talking about having sex for some time but didn’t want it to be in the bed of my truck especially now that the weather had gotten much colder. We had decided we were going to do it and made plans to be alone at my parent’s house when they were gone. Football season was over, and my Friday nights were now free giving us two nights a week to make it work. My sister had a band concert coming up which would give us about an hour or so alone in my room. It was perfect and we decided that was going to be the night. The week of the concert finally arrived, and we talked about our plans every night on the phone. I didn’t get to see her too much during the school week, so I was jacking off every night thinking about the night to come.

I had a hard on most of the day of the concert and couldn’t stop thinking about what we were going to do that night. I got out of school early that day and went straight to my room and jacked off just for some relief. An hour later, I picked her up from school and we went back to her house to watch TV. I couldn’t take my eyes off her and all I could think about was having her. We told her parents we were going to get a burger but headed to my house and parked down the street. It seemed like it took forever for my parents to leave for the concert, but we finally saw them drive away. The time had finally come, we arrived at an empty house and headed straight for my bedroom. We began kissing while I was undressing her. When she was down to her panties and bra, she stepped away from me and took off her bra. God, she had great breasts. She then slid her panties off and crawled onto my bed. I had seen her breasts, rubbed them and kissed them, fingered and licked her pussy but, this was the first time I had ever seen her completely naked. My God she was beautiful! Her pale skin in the dimly lit room accented all her curves. She lay back against my pillows propping herself up on her elbows watching me undress. My eyes moved all the way down her body. Her eyes seemed to be peering through me. Her lips were full and red. Her breasts were plump and stood almost straight out from her chest and her nipples were hard and poking out. Her stomach was flat, and her hip bones protruded making a little valley from her belly button to the bulge of her pubic bone. Her pussy was covered in a patch of dark curly hair and I could just make out its lips disappearing between her thighs. I pulled my underwear off and my dick popped out, already rock hard and pointing straight up. As I climbed onto the bed she asked if I had the rubber. This time I was prepared, and I pulled it out from under my pillow. My hands were trembling as I opened the package, took the rubber out and rolled it over my dick. As I moved down to her feet, she drew them towards her and spread her legs revealing her pussy to me. She was soaking wet and I was ready to be in her.

As I crawled my way up her, I noticed how hot her body felt. I stopped just long enough to kiss her nipples before finding her waiting lips. I kissed her hard and my tongue found its way into her mouth. Her tongue met mine and as we kissed, I lowered myself on top of her and felt the heat of her soft body against me. I felt my dick settle between her legs and push against her pussy. It felt strange having the rubber on, I could feel her but couldn’t feel her. I pushed and my head parted her lips and began to slide easily into her. I wanted to be gentle in case it hurt her, so I was going slow. She asked what I was waiting for and urged me to take her. That was all I needed and with one quick thrust, I was all the way in her. I didn’t feel the tightness I had felt with Rebecca that had stopped me from entering her but that was it, I was no longer a virgin. She let out a soft moan as she exhaled and looked straight at me with burning eyes. The sensation was unreal as she enveloped me, surrounding me with her warm flesh. Her breasts felt so good against my chest and our breathing was hard and in sync with the others. I could feel her heart beating against me. I kissed her again and then raised up on my hands and began to slowly pump in and out of her. After a couple minutes, I felt myself about to cum. I wanted it to last longer but it was too late, I could not stop it. With a couple fast thrusts, I closed my eyes and felt my orgasm take control. My body tensed and I filled the rubber with spurt after spurt of cum. I fell on top of her and my quickly shrinking cock slid out of her soaking pussy. It was the first time I had gone all the way with a girl and although I didn’t last long, I thought it was amazing. The entire event had lasted less than five minutes. It certainly had not lived up to the love making session I had imagined but was probably par for most teenage kids having sex for the first time. She told me it was good, but I wondered if it had been for her. I didn’t feel the pressure of pushing through her cherry and I often wondered if I had been her first. I loved her and whatever she did before we met didn’t matter. Besides, I had been with Rebecca and Ashleigh and had never told her about them.

Practice makes perfect and we were certainly up for the practice. We spent the next several months having sex every chance we got. Mostly that meant in the passenger seat of my truck which wasn’t the most romantic place, but we were kids and it didn’t matter. I got better and could last longer than a couple minutes and I’m sure it was more enjoyable for her or at least as enjoyable as it could be in the seat of a truck. That spring I turned eighteen and graduated from high school in May. I had no idea what this summer would have in store for us, but a new adventure was on the horizon.