Where it happened: basement guest bed
Langauge: English
Sex: Female
Rating: 6
Category: Straight
I was raised in a very strict home and went to an all girls boarding school. Dating was not only discouraged, it was impossible. I learned about sex mainly from my school friends, some of whom were not as restricted as I was. I was very very curious about it, but had little opportunity to explore it.
This past summer I was home from school and our family had visitors for week. They were my dad’s old friend from school and his family. I hadn’t seen them for many years when their kids were very young. They had a son, Dennis, who was now 14 and a daughter, Lori, who was 10. Both kids still seemed very young.
It was late at night on the first day they were with us. I had gotten up to get some water in the kitchen and everyone else was in bed. I heard some noises coming from the basement. The door down there was right off our kitchen. I quietly went through the door and silently started going down the stairs. I stopped when I saw what was making the noise. Dennis was lying on the bed against the wall. The bed was facing away from the stairs so he couldn’t see me. He was naked on the bed masturbating. I just froze looking at him. I had never seen a penis before except in my friend’s magazines. Dennis was stroking his penis up and down with one hand. His legs were outstretched and he was rubbing his feet and legs together. With his other hand he was tickling his nipples. His eyes were closed and he was quietly moaning. That was the noise that I had heard. I was transfixed looking at him. He looked so young. His body was smooth and hairless, except for a little patch of dark pubic hair. He had a full mop of long brown hair that fell in his eyes and made him look even younger. And yet his penis looked fully mature. Watching him, I was experienceing feelings I had never felt before. I was tingling between my legs and my nipples were hardening. Suddenly, a stream of white fluid erupted from Dennis’ penis. It continued to shoot out of him and landed on his chest and stomach. His face looked so happy. I quickly and quietly tiptoed upstairs before he opened his eyes. I went back to my room. got in bed and couldn’t stop thinking about what I had just seen. I began fingereing my own vagina and nipples and fantasized about what it would be like to be with Dennis, or any boy for that matter. I had masturbated many times before, but never had a clear image of a boy in my mind until now. The sight of Dennis ejaculating was burned in my mind forever.
All the next day that’s all I could think of. Now Dennis and I were getting along pretty well and he was a very nice boy. Since he looked so young, I don’t think my dad ever even considered that something could happen between us. Nothing did happen that next night although I did sneak dowstairs again and watched Dennis again. Now I knew what I wanted to do. The next day I got a hold of some condoms and made my plans for that night.
Everyone had gone to bed but Dennis and I were up watching a movie. I wanted to keep him up until I was sure everyone else was asleep. I snuggled on the couch next to Dennis and we starting talking about girls and boys and relationships. He had never had a girlfriend before but he really didn’t have a lot of confidence in himself. I began to boost up his morale. I told him I thought he was cute and sexy. (I did, too) He was wearing shorts and I began to rub his bare thigh. He was enjoying it. I remembered how he rubbed his legs and feet together so I kicked off my sandals and ran my bare foot along his leg. Then I kissed him. It was obvious that this was both our first kisses. We were both a little awkward but soon we were really getting into it. We both still had our shirts on but I enjoyed the pressure of his chest against my breasts. I ran my fingers through his long brown hair and massaged his scalp as we kissed. This was so nice. I could feel his crotch against my leg and he was obviously erect. I told him I never had a boyfriend before because my family was so strict but that I had always wanted one. He said it’s too bad we live so far apart. Me too, I said. All the while the image of Dennis’ naked body and his penis erupting was flashing in my head. I said, “Dennis, you can do me a big favor.” He asked what and I told him I wanted to lose my virginity to him. Well, at first he looked shocked. I continued to stroke his leg and I put my other hand on his chest. Remembering how he had touched his nipples, I began to massage them through his shirt. He said, “I do too, but where do you want to do it?” I said I would meet him down in his room but first I wanted to check to make sure that everyone else was sound asleep first. He said ok and got up and went downstairs. I checked and everybody else was sleeping. I went to my room and took off my clothes and underwear and put on my pajamas. I also took the condoms out of my drawer and went downstairs. That naked image of Dennis was all I could think of.
I couldn’t imagine what was going through his mind as he waited for me. I went through the kitchen and closed and latched the basement door behind me. Dennis was sitting on the edge of his bed still wearing his shorts and tee shirt. I sat down next to him and we kissed again. I put my hand up under his shirt and rubbed his bare chest and tickled his nipple again. Well now he was like putty in my hands. Since he was so young and inexperienced he wasn’t taking any initiative at all. That was ok with me because I thought it was so cute. I said I’m going to get more comfortable and I unbuttoned my top and took it off. Dennis just stared at my bare breasts, which had never been seen by any boy before. Then I reached over and pulled his tee shirt off. I took his hands and put them on my breasts and told him I wanted him to feel them. He timidly rubbed me but it felt so good. Eventually he gently fingered my nipples like I had seen him do to himself. I told him I loved what he was doing to me. As he played with my breasts I reached down to his shorts and unzipped them. I reached in, pushed his little white cotton briefs aside and pulled his hard penis through his open fly. I said, “Dennis, its so big!” and he smiled. Actually it was about five inches, big enough for what I wanted. Dennis laid back on the bed and I began to stroke his penis up and down for a few strokes. Then I stopped and pulled his shorts and briefs completely off. Although Dennis didn’t know it, this was the third time I had seen him nude, but of course never this close. Now I really had no idea how to perform oral sex, and I didn’t want to try for fear of hurting him. I did kiss his penis, though, and I tasted the salty precum that was dripping from him. Honestly, it didn’t do anything for me. While stroking and rubbing his penis and balls with my hand, I kissed my way up his belly and chest. His skin was so smooth and soft, just like mine. I was kind of glad that my first sex was going to be with this boy and not a hairy old man. I had seen my dad swimming and it wasn’t a pretty sight. I began to kiss and suck on his little nipples and he was clearly enjoyng it. Then I said, “Dennis, I want you to do that to me.” I laid on my back and Dennis knelt next to me and planted his lips right on my nipple. He sucked it and twirled his tongue around its tip. On, my God, this was incredible!! He went back and forth from breast to breast as I continued to fondle his smooth genitals. It felt like a river was flowing between my legs. The tingling sensation was intense. I moved my hand up to his shoulder and moved it down his smooth back. His muscles were actually pretty firm and even though he still looked young, he was clearly changing from boy to man. His hair was tickling my chest as his mouth was sucking my nipples and he was in heaven. But not as much as he was going to be. Or me!
I knew now I was ready. I broke him away from my breast and pulled my pajama bottom off. The condom was in the waistband and I took and opened it. Dennis asked if he could look between my legs and I said of course and spread my legs. He put his hand down there and slipped his fingers in. I gasped as he stumbled on to my clit. I told Dennis to just keep rubbing it there and this little 14 year old virgin brought me to orgasm! I wanted to scream but I knew we couldn’t make any noise. When I calmed down I told him he was great and now I wanted him in me. He took the condom and rolled it on to his penis. His hand was still very wet from my cum. He knelt between my legs and stretched out above me. I guided his penis to me and he slid all the way in. My hymen had broken during one of my frequent solo experiences so there was no pain. Finally a boy’s penis was inside of me. And I was glad that it was Dennis. I had really gotten to like him and I was happy that he was my first. I had always heard that you should love the person you had sex with and I really did love Dennis then. He thrust effortlessly in and out of me and I could tell he was enjoying the experience. I know I was! I had my hands on his smooth butt and pushed him into me. He got that look on his face that I had seen when he was alone on his bed and he exploded deep inside of me. I could feel the fluid shooting through his shaft even with the condom on. As he continued thrusting I was again working up to a strong climax. I tightened his legs on him and came again. Now I knew what sex was like! It took me 17 years and a life of guilt but now I knew. Dennis and I held each other in our arms for the longest time. This was a life changing experience for him too.
Unfortunately, this story doesn’t end happily. On the night before they left my dad caught Dennis and me in bed. He had gotten up to get some milk and I had forgotten to latch the basement door. He heard some noise and came downstairs and we were in the act. (Fortunately our second one of the evening.) He ran downstairs and pulled Dennis off and started hitting him. I screamed and soon everyone was down there. Dennis’ dad and my dad got into a big fist fight and it was ugly. Dennis wasn’t hurt too bad but our families’ friendship was over. I got banished back to the boarding school and I’m counting the days until I’m 18. Dennis and I still manage to keep in touch. His family is not mad at me at all and they have invited me to live with them when I turn 18 so I can go to college in their town. I don’t know what is going to happen with me and Dennis, but we will always have that wonderful memory to share. I only hope that someday my dad will understand. I still love him, too.
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