This is a story about how I lost my virginity. All names and such have been changed to protect identities.
Let me start out by telling you a little about me, my name is Thomas and these events happened when I was thirteen years old. Back then I was a scrawny stick of a boy standing 5’8” and weighing only 120 pounds. I was never really popular with the ladies, never many girlfriends until I met Christy. Now she wasn’t really a looker at 5’3” and weighing maybe 175 pounds and 38 C breasts. We simply met through a choir function which we were both (forced) to be a part of. I noticed her through the crowd of people and went up to her and just started talking to her. We never considered dating the first few times we met, so I was always out with the cheerleaders helping them learn to flip and basically doing all the guy stuff they needed. I remember the one night that Christy called and told me she wanted to take our friendship to the next level. I was beyond happy, she was my first ever girlfriend that I could actually tell my parents about and my friends also and have them believe me. Now when we first started dating it was just a more casual holding hands at school and seeing each other between classes. It took three years for our relationship to really develop to a physical level to where we were comfortable with kissing each other. In the time we had taken to calling each other at 11 or 12 o’clock at night and just talking until we fell asleep. Our conversations were mostly harmless for the first few months and then we discovered our naughty side. They started out simply with me asking her what kind of panties she was wearing or what color her bra was at the time, and eventually progressed to asking her to finger herself for me and play with random objects.

The first time I asked her it was 12:30 at night, “Christy I have a small question I would like to ask you.” She was quiet for a second and then with a slight hesitation in her voice she answered “You can ask me anything Thomas.” I sat there quiet for a few seconds not knowing how to voice what I wanted to ask her when I heard her voice again “If it is something naughty then just tell me I know what has been going through your head, and I see the way you look at me when we are alone.” I gathered up all my courage and finally managed to squeak out “I would love it if you would finger you while I jack off and we both cum at the same time.” I heard her draw a deep breath and then there was silence on her end. I feared I had driven her away with such a forward statement. I heard her walking and then water running so I ventured a question “Why are you in the bathroom at this time of night, won’t your parents get up and find out what you are doing?” I heard her chuckle and tell me that both her parents had, had a little bit much to drink and were passed out in the living room and she could go jump on both of them and they wouldn’t get up. I asked her again “what are you doing in the bathroom now?” This was common for us to be in the bathroom with each other when we were brushing our teeth before going to bed but, it was way too early for her to even be considering bed. To this day I can swear I hear a smile in her voice when she told me “I am shaving my pussy because I want it to be silky smooth when I play with it for you.” I nearly dropped the phone as I came in my pants, and with my voice suddenly very breathy I said “you never said you would do that and I just came in my pants so can we put this on hold until another night?” She laughed and laughed for a good five minutes before she could even say anything. “You just came in your pants because I said I was shaving my pussy.”

I sat there unable to answer her because this had never happened to me before, I was unsure of how to answer her. I considered hanging up the phone right then and there because the shame I was feeling was multiplied by the thought that I had never done anything sexual before and here I was with a hair trigger and I hadn’t touched it. There was the awkward silence that both of us had fought so hard to avoid in all of our conversations. I took a deep breath and answered her “Yes I did and I didn’t mean to I just got so excited because you are the first girl to ever tell me something like that.” She giggled like a little school girl until I asked her to stop it. She giggled some more and asked me why she should. I told her that the giggling was bringing down my self-esteem because not only was I still a virgin but I seemed to have a hair trigger when it came to things like that. She started taking deep breaths to calm her breathing down until she was able to talk. Our conversations continued like that up until my sixteenth birthday, that was the day that I would get the phone call that would change my teenage life. I had the phone by my side that night because at school Christy had pulled me aside and said she was calling that night and had something very important to tell me. I kept on questioning her every time I saw her and she wouldn’t relent on telling me to wait until later.
Finally when 12 o’clock rolled around, I jumped when the phone started to ring and grabbed fast so not to wake my father. I said hello tentatively when I hear her voice say “I bet you hated me for all that teasing at school when I wouldn’t tell you what this call was going to be about.” I truly did hate that she did that I didn’t hate her. So we settled into our normal rhythm of going back and forth until both of us came and after I finally did, did she tell me what she wanted to tell me. “In honor of your birthday I have decided that this weekend we will finally take our relationship to the last level.” I was shocked beyond belief; I had been waiting for this moment for the longest time. I would no longer be a virgin after this weekend was over. We talked until 2:30 before she said she was going to sleep to try and get this week over with so we could have our special weekend. My birthday came with the pomp and circumstance that came with the usual birthday around my house. I really didn’t talk to Christy that much on the phone since that fateful night. For me the weekend seemed to take forever to get there but when it did I could hardly sleep the night before. I kept on getting weird looks from my parents because I kept on dozing off in the car as we drove to go get groceries. They knew I had plans to go see Christy at the rec center not far from our house. We finally got done shopping and before I knew it I was waiting on Christy to get dropped off. From the moment she stepped out of her mother’s car I knew that it was going to be a very interesting day.

We took our time slowly walking around the perimeter to scope out a good place for both of us to have sex without being seen or not knowing if someone was sneaking up on us. We came to the conclusion that the woods would be the best place since the inside had cameras everywhere. So we took off into the woods and when we found the right spot she jumped on to me kissing me with a passion that I had never seen from her. Our clothes were off in a matter of seconds, we weren’t wasting any time we wanted to get down and get dirty for the first time in our lives. I looked at her and was amazed by what I saw; she was beautiful for her weight. We both were virgins so we didn’t really know how to have sex so we tried different positions until we found the one that worked best for us. I was lying on the ground and she climbed on top of me and just impaled herself on my penis without regard for foreplay or anything. We fucked like rabbits for maybe ten minutes before I came deep inside her without regard for the possible consequences. I smiled up at her and said “That was the best birthday gift any one could ever give me.” She smiled back climbed off of my penis and proceeded to suck it clean and after a few minutes hard again. This time we tried doggy and I managed to last about thirty minutes this time and came deep inside her again. When we got done having sex she was all aglow and she was more than happy to let me watch my cum fall out of her pussy on to the ground. We cleaned up the best we could and headed back to play some pool. After she left I started to consider the events that had taken place that day. We continued to fuck outdoors for another couple of months until I got the most frightening phone call a guy could ever get, she was late. I knew immediately that it was just from all the sex we had been having, throwing caution to the wind. I asked her how far along she was and she said she was about six weeks. She cried to me on the phone for the better part of four hours. I had no idea what I was going to do, or how I was going to tell my parents. The weeks rolled by as I still looked for that one moment to tell my parents that my girlfriend was pregnant when I got another still scary phone call from Christy. This one was to tell me that she had had a miscarriage. I didn’t know what to do and from that moment on I promised myself to be a better man. She didn’t see it that way and just a few days after she miscarried she broke up with me stating that she couldn’t date someone who had created life with her and then to have the life taken away.

To this day I will find my self thinking about what my life would have been like if Christy hadn't miscarried the baby and I would have become a daddy.That part of my life is over and I have moved on.

story by: Lnknprkht

Tags: school first time teen male/teen female virginity true story plumper pregnant sex story

Author: Lnknprkht

Related sex stories: