Where it happened: Her Bedroom
Langauge: English
Sex: Male
Rating: 5
Category: Straight
The first time that I fucked Carolyn she was still fourteen years old, I was slightly older, and she would not become fifteen for a few more months. I don’t know if she offered her virginity to me or had been fucked by someone else previously. After the first time we fucked each other we continued see to each other frequently and the two of us would fuck each other whenever we had the opportunity. We continued to fuck each other until a few months before she turned sixteen.
This evening with Carolyn started the same as every other evening with her during the previous two months. Carolyn and I would be in the living room hugging, kissing, talking and listening to music. Her brother, his wife and my parents would be in the kitchen involved in their favorite pastime, playing cards. Other than our hugging and kissing we were doing nothing that we would have to conceal if any one of them were to enter the room.
Until this time I had never touched her any place on her body that some would consider inappropriate. This included her rear end, breasts and pussy either directly or through her clothing. I don’t know why but for some unknown reason I took a chance with her and slid my hand down the back of her skirt, beneath her panties and onto the soft cheeks of her rear end. I had absolutely no idea what kind of a reaction this would bring from her since I had never attempted to touch her like this previously. Her reaction was to do nothing that would that would give any reason for me to remove my hand from where I had placed it. I took this as her approval to continue and started to rub and squeeze the checks of her rear end. We continued to kiss and embrace each other while I fondled the cheeks of her rear end. It was then that she whispered into my ear “Let’s play a three minute game.” It took only seconds for me to realize what she had said to me. She was telling me that she wanted to be fucked and had just asked me to fuck her. There was no hesitation on my part to agree with what she wanted. This was the chance of a lifetime for me because it would be my first opportunity to fuck a girl.
We listened to see if it might be safe to leave the living room and then very quietly went up the stairs to her bedroom. After we entered her room she placed her hands under her skirt, pulled down and removed her panties. She then lifted her skirt up around her waist and lay across the side of her bed. She lay there with her legs slightly apart and hanging over the side of the bed. Her sparse patch of dark brown pubic hair with her pussy located at its bottom was positioned over the edge of the bed. I stood near the side of the bed and looked at her pussy as she lay there for a few moments. This was the first time I had ever been able to see a girl’s pussy as completely exposed to me as hers was. She was lying there naked from the waist down waiting for me to put my cock inside of her pussy. I lowered my pants to my ankles and then moved close to her, placing myself against her legs with my erect cock almost touching her pussy. I was about to touch her pussy for the first time and it was going to be with my cock as it entered into her. I still could not believe that I was about to put my cock into and fuck a pussy for the first time. I placed the head of my cock against her pussy but when I tried to push it into her I was not able to enter her pussy. After the head of my cock passed between the outer lips of her pussy it would not go any farther. I tried again, this time pushing against her pussy even harder but I was not able to enter any farther than before. It was then that I said to her “I can’t get ’er in”. She found this comment to be very amusing because it sounded as if I were referring to myself in a feminine manner.
I had no idea that getting my cock inside of her pussy could be so difficult. I was still very naive about the anatomy of a woman’s pussy. All I knew was that there was an opening big enough for a man to put his cock into. I knew nothing about the existence of the urethra and clitoris. As far as I knew when a woman urinated it came out of the same opening that a cock would go into. I also had no idea that a woman’s pussy would secrete a natural lubricant that would allow easier entry of a man’s cock when she was ready to be fucked. What I did learn very rapidly is that her legs should be spread far enough apart to open her pussy. I realized much later that I was trying to make a new opening where her clitoris is located. I don’t think that she knew that she could have helped by placing my cock at the opening into her pussy and guiding my cock inside of her pussy.
I asked her to spread her legs farther apart so that I could stand between them and have better access to her pussy. Now I was able to see the opening of the pussy that my cock was trying to enter. I placed my cock against and slightly inside of this opening to her pussy and started to push. This time when I pushed my cock into her pussy I was able to start entering into her and in doing so my virginity became history. I watched as I saw my cock disappear into a pussy for the first time. First the head as I saw it pass beyond the opening that was the entrance into her pussy. I then saw the shaft of my cock slowly vanish from view as it slid into the depths of her pussy. For me it is a visual sight never to be forgotten, watching my cock make its first entry into a pussy. It was only after my cock was completely within her pussy for the first time and the pubic hair of our bodies made contact that I stopped watching. The entry of my cock into her pussy had been difficult because she was barely wet enough. Despite this I had been able to get my cock past the entrance of her pussy and start my entry into her. The deeper I pushed my cock into her pussy the easier it became for me to continue my entry into her. I did not stop pushing into her until I had the entire length of my cock inside of her pussy.
I still have my doubts as to whether or not she was still a virgin when I first started to enter her pussy. Some of her actions caused me believe that I was the first to have ever fucked her and that she was still a virgin. Yet some other things about her made it appear that my cock was not the first to know the inside of her pussy. It was as if she did not know what to do to allow the entry of a cock into her pussy. I even had to ask her to spread her legs far enough apart to give me access to her pussy. She knew that my cock was supposed to go into her pussy but it appeared she did not know how to make it happen. Only that somehow I was supposed to enter her and be in her pussy with no help on her part. On the other hand there was no bleeding or pain from putting my cock inside of her pussy for the first time. At no time did she show any signs of being shy about exposing her body to me. She was neither apprehensive nor nervous about the fact that my cock was about to enter her pussy and that I would be fucking her. It was as if she had been fucked previously but did not know what she should do to help. I will most likely never know if she gave her virginity to me when I first put my cock into her pussy.
It was not until I had completely entered her pussy that it started to become wet enough for us to fuck. I started to move back and forth instinctively so that my cock was sliding in and out of her pussy. This started some activity on her part as she would lift her hips to meet me as I pushed my cock into her pussy. The position that she was in with her legs hanging over the side of the bed did not allow much motion on her part. She laid there and allowed me to slide my cock back and forth inside of her pussy with only minimum movement on her part. She finally started to get quite wet which made it easier for my cock to slide back and forth in her pussy while I was fucking her. She and I continued to fuck each other, but after a short while she started to become nervous. She was afraid that it would be discovered that we had gone upstairs and would be caught while we were fucking. Despite the chance of our being caught, literally with our pants down, neither of us wanted to or was ready to stop fucking. It would only have taken one of the four adults that were downstairs to use the bathroom and discover that we were no longer in the living room. I was not ready to stop fucking her and she was not ready for me to stop. I desperately wanted to continue fucking Carolyn until I had an orgasm inside of her pussy. I continued to push my cock deep within her pussy only to pull it out again without completely removing it from within her pussy as I fucked her.
I believe that we had been fucking for about fifteen to twenty minutes when I could feel my cock starting to swell inside of her pussy as I approached my climax. It took less than a dozen more deep strokes into Carolyn’s pussy when my orgasm started. The wave of ecstasy that swept through my body with that orgasm as I ejaculated that first load of cum deep into her pussy was unlike anything that I had ever experienced. With each following wave of my orgasm I would thrust my cock deep into her pussy as I released more cum into her. My orgasm did not end until after I had been drained of cum and nothing remained for me to ejaculate into her pussy. I was no stranger to self masturbation but from that moment on I knew it would never feel as good as what I had just experienced. I continued to maintain the rhythm of my cock moving back and forth inside of her now very wet pussy until my erection subsided. After my cock had become completely limp inside of her, I slowly eased myself out of her pussy. I have no idea how it felt for her, for me to fuck her and then to feel cum shooting out of my cock as I erupted inside of her. I like to think that even though she did not appear to have an orgasm it was something that she enjoyed. I do know that for me I had just experienced something that felt absolutely wonderful.
After we were finished fucking, both of us then replaced and straightened our clothing. Then we quietly went back down the stairway to the living room, being careful not to attract the attention of either my parents or her brother and sister in law who were still in the kitchen playing cards. We then did our best to act as if we had been there the entire time and that nothing had happened upstairs in her bedroom. On that night we crossed a major milestone in our relationship and from then it was inevitable that we would fuck each other at every opportunity.
After this first time, over the next six to eight months, Carolyn and I managed to fuck each other about twelve more times. Two of these times when I fucked Carolyn are the most memorable of all. Even though it has been almost sixty years since I fucked Carolyn one of these twelve are among the best fucks I have ever experienced. We had been fucking each other hard and furious for at least two hours and I was still not ready for my first climax even though she herself already had multiple orgasms. It was only after Carolyn said “My pussy is sore.” that I allowed myself to climax and shoot a massive load of cum into the depths of her pussy five to ten minutes later. The other was the last time I fucked Carolyn and it happened about two months after we stopped seeing each other. I was with three of my friends when we went to Carolyn’s home and asked her to go for a ride with us. After she got into the car I asked her if she would allow all four of us to fuck her. After Carolyn said yes we found a secluded place to park and I was the first of the four to fuck her and leave my load of cum inside of her pussy. After Carolyn had been fucked by all four of us we took her home dropped her off at her house.
About a month or so after Carolyn had let the four of us fuck her, I saw her for what would be the final time. The only thing she had to say to me was “You made me into a bad girl.” I did learn many years later that she became pregnant a couple of months after her sixteenth birthday. This would have been about four to six months after the last time I fucked her. Carolyn became pregnant in March and gave birth in December while she was still sixteen years old. This would have been about three weeks before her seventeenth birthday.
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