Where it happened: my room
I have been reading this site for the past six months. I was a virgin when I started and had always been sexually curious, but the stories here gave me the inspiration to actively pursue my desires. For that I thank you.
I have never dated much. I am what you might call a plain Jane. (in fact, my name is Janet) I am not unattractive, but I’m certainly not a raving beauty. I’m tall (5 ft. 10) and thin (115 lbs.) My breasts are not bad (32C) but no boy has had a burning desire to see them. My light brown hair is long and stringy, and I can’t really afford to have it professionally styled. So I have felt self conscious and have avoided the dating scene. Besides, I’ve never been asked. Makes it hard to experience sex, doesn’t it.
That hasn’t stopped me from learning how to pleasure myself. I can always bring myself to orgasm. But my right hand is a poor substitute for a boy’s penis. The more I read the stories here, the more I knew I had to do it. Just in case I did ever get lucky, I got myself on to birth control pills. I knew it was safer, plus I didn’t want my first time to be with a condom.
Some of your stories made it clear to me that the answer was living right under my roof. After my parents divorce three years ago, I stayed with my father so I could finish school here rather than leave town with my mother. My father remarried early last year. His new wife had two boys that are now 9 and 14. The 14 year old, Scott, is kind of small for his age and a little shy. He is good looking and girls are always calling him, but he hasn’t started dating, either. We get along very well for step sister and step brother. By now you can figure out who my first time was with.
Scott and I were at home alone on New Years Day 2000. My dad, stepmom and Will, the younger boy, went to watch football at my dad’s friend’s house. Scott and I are not big football fans so we stayed home. I was on line going through a lot of the early stories on this site that morning and was getting very horny. I was reading stories about older girls and younger boys and began thinking about Scott. I knew he looked at Playboys and I suspected that he masturbated and I knew that even though he was shy, he did have normal desires about girls. He was cute, we weren’t blood relatives, he was boy, I was a girl, we were alone, so why not? I logged off and went to the family room where Scott was watching a movie. It was almost over and I watched the end with him. When it finished he turned off the TV and we started talking. I asked him about the girls that had been calling and he said there was one that he really liked. Her name was Katy. He wanted to call her but he said he was afraid. I said any girl would want to go out with a good looking guy like you. (He was attractive, too. Not a blemish on his face, a nice smile, long brown hair that framed his cute face and a small but nicely shaped body. I was getting turned on myself looking at this teenager.) He stammered a bit and I finally coaxed the problem out of him. It seems that Katy was sexually experienced and he was afraid that he might not be able to perform up to her standards since he was a virgin. Well, my goodness, what an opening! I sat down next to him, took his hand, and said, “Scott, how would you like to get some practice before you go out with Katy?” He looked very surprised and said, “you’d do that for me?” I can clearly remmeber my words. “Scott, I’d love to help you because you’d be helping me too. I’m a virgin too and I’m not very comfortable with boys. We can learn together. Besides, I really care about you and I’d be honored to have you be my first.” He asked if I wanted to do it now and I said of course, if you do. He called his mom to see how they were doing, but mainly to check if they were still planning to be out all day. Everybody was most interested in the Orange Bowl, which was the last game of the day. We knew we’d be alone and safe all afternoon.
I was getting so excited as I watched him talking on the phone. We went to my room and we just stood there for a second looking at each other. I decided to take the lead. I said, “Scott, lets go about this slowly so we can learn and really enjoy it.” I stepped toward him and gave him a kiss. He was about five inches shorter than me so I had to bend down slightly. At first we kept our mouths closed with only lips pressed against lips. Then I stuck my tongue out until I felt his teeth. He got the idea and opened wider and our tongues met. I got my first taste of boy and it was nice. He had been eating candy and his mouth was all sweet. We had our hands on each others waists. His eyes were closed but mine were open and I looked at his serene face. I knew I was doing the right thing. I broke off our kiss and he opened his eyes. My hands went from his waist to the bottom of his tee shirt. I grabbed both sides of the shirt and slowly began to lift it up. First his thin waist was revealed above his jeans. The skin on his stomach was smooth and white and I marveled at how flat and hard he was. I raised the shirt higher and his pectoral muscles formed a very attractive young chest. There wasn’t a hair on it and his nipples were a light pinkish brown. He raised his arms and I pulled the shirt up over his head and off. He had a trace of brown underarm hair and his biceps were solid. His hair was messed and I smoothed it down a bit. Looking at his bare chest, I knew the first thing I wanted to do. I sat down on the edge of my bed and had him step close to me. He was still standing and I leaned forward and placed my lips on his right nipple. I twirled my tongue on it and he took a deep breath. I said, “Scott, did that feel good? and he said, “oh, yes.” The right nipple was hard and erect and I went over to his left and repeated the process. As I played with his nipples I was rubbing his back. Looking at his reaction I knew then that I could seduce a boy. I kissed all over his chest and worked my way down his stomach. I stuck my tongue in his belly button and he giggled. By now he knew which way I was going so he gave me a little help. While I was licking around his belly button he reached down and unbuckled his belt. He unbuttoned his jeans and pulled them down and let them fall to the floor around his ankles. A little bit of brown hair was protruding above the wasteband of his white fruit of the loom briefs. Even more obvious was the bulge pushing those briefs out. I moved my hands down lower and placed them on his buttocks which were still covered by the briefs. I got on my knees but did not yet remove his pants. Instead, I licked the bare skin of his inner thighs. I don’t think he was expecting this and he breathed heavily again as he spread his legs apart to let me in. This skin was as soft as his chest and stomach had been. I could feel that his body was tense and was anticipating what I would do next. At the tip of the bulge under his shorts was a small wet spot. I touched it and it was slippery and sticky. I then slowly pulled those briefs down, first revealing more pubic hair and then his penis sprung free. Fully erect and hard, it was about six inches long. The fattest part of the tip was about two inches across and the whole tip was coated with clear fluid that was dripping from the slit in the front. His balls hung in a little pink sac beneath his penis that was also sprouting some brown curly hairs. I let the briefs drop down onto his jeans and took his penis in my hand. I stroked it slowly and spread the pre-cum all down its shaft. Scott was purring softly like a contented cat. My other band cupped his balls and I massaged them gently. I knew Scott was happy but I was too, just knowing I was bringing him such pleasure. I knew mine was to come. My vagina was as wet as Scott’s penis was. I couldn’t wait to show him, but first I had more work to do. I opened my mouth and put my lips over that two inch head of his penis. I closed my lips and twirled my tongue on it. I was getting another taste of boy, and this was really exciting. I took him deeper in my mouth and thrust my lips up and down his shaft. My hands were on his now bare ass. I stopped sucking just long enough to look up and tell Scott to let me know when he was going to cum to I could see it. He was looking down at me through the hair that was falling in his eyes and he had a big smile on his face. I put my mouth back on him and and moved my lips quickly back and forth on the head of his penis. Scott’s voice was changing and it was usually deep, but I heard him say “Janet!” in the higher voice he still had when he was excited. I pulled back and watched as a stream of cum shot straight out of his penis. It hit my face and blouse and was followed up by a series of explosions out of him. I put my hand on his penis and continued to milk him. He finally concluded his ejaculation and my blouse was soaked with his thick white sprerm. He looked down and just said, “oh, thank you.” He was so incredibly cute standing there. I stood up and gave him a big kiss.
I winked at him and said, “well Scott, I’d better take this off!” I unbuttoned my blouse, took it off and wiped off my face, arms and hands with it. He also got some on my jeans and I removed the slippers I was wearing and then removed my jeans too. I was standing there in just my bra and panties. Scott had removed his shoes and stepped out of the jeans and briefs. He sat down on the edge of my bed. I guess he was tired since he had been standing the whole time. I unhooked my bra and slowly removed it. Scott’s eyes were fixed on my bare breasts. Suddenly, I was very proud of them. They are very nice and well proportioned. And yes, I am thin, but my body is not unattractive. Standing there with Scott, I finally realized that. I dropped the bra to the floor and walked toward Scott. Before I got close enough for him to touch me, I stopped and slowly pulled down my panties. I don’t shave and my vagina is surrounded by a thick bush of light brown pubic hair. Right then, a lot of that hair was wet and matted. The panties hit the floor and I stepped out of them and toward Scott. He said, “my turn now” and he planted his mouth on my right nipple. Now I was the one getting pleasure. He kissed and licked me as I had done to him. He went from breast to breast and I was getting more and more excited. I slipped my finger between my legs and massaged my clitoris as my cute 14 year old stepbrother was sucking the hell out of my bare nipples. This was better than I had expected. I looked down at Scott and he was fully erect again. I wanted to experience oral sex, but looking at his penis I was more anxious to feel it inside of me right then. I took the hand out of my vagina and spread my wetness on his penis. Scott continued his work on my breasts. I said, “Scott, you’ve gotten me so excited, I’m ready for you now!” He looked up and his voice cracked again as he said “really?” I said. Oh, yes.”
I was so ready for what was about to happen. All my fantasies and all the hours I had spent reading My First Time were going to finally pay off. Scott was the absolute perfect partner for me. He was so willing and eager and neither of us had to go through an awkward courtship to reach this point. We both wanted this experience and now it was going to happen. I laid down on the bed and he laid down beside me. I looked down his chest to his hard penis and I noticed something. I said, “wait a second” and he said “what?” I scooted down to his feet and pulled his socks off. He laughed and said “oh, I forgot!” So while I was down there I sucked on his toes a bit. He loved it. I worked my way up him again and kissed his penis, which was again dripping. Then I kissed each nipple and finally went up to his mouth. Our tongues again got wrapped up in each others and we laid on our sides with our heads on my pillow as we frenched. I put my arms around him and pulled him up against me. My breasts were pressed against his smooth bare chest and it felt so right. Scott was lightly scratching my back and it felt so good that I had shivers all down my body. He was also rubbing my leg with his foot. Oh, it was great! All the while, his penis was pressed againt my stomach, ready to go.
While still holding him, I rolled onto my back with Scott on top of me. We were still kissing, but I slowly opened my legs apart. His legs were stretched out between mine. I reached down and took his penis in my hand. Then I whispered, “Scott, let me guide you into me.” He scooted down just a bit until the head of his penis was at the entry to my vagina. Still holding him, I rubbed it up and down my slit. We were both enjoying this teasing. Then I held him still and thrust myself toward him. I gasped as my vulva enveloped his tip and I removed my hand and said “Scott, you can go all the way in, now.” He slid in slowly and his shaft dragged across my clitoris as he pushed in. He said, “oh, God, this is great!” as went all the way in. I knew I had all six inches inside when I felt his balls against me. He placed his hands flat on the bed, outstretched his arms and raised up his head and chest so he could begin thrusting. And thrust he did! Scott was a virgin, but nature must have taken over. He went in and out with a steady rhythm and I was experiencing the greatest pleasure of my life. My hands were running up and down his back and he felt so strong. He wasn’t just my little stepbrother anymore. I felt my body shaking and I was getting so warm. My first orgasm was everything I could imagine and more. I screamed, “oh yes, Scott!” as my juices flowed freely. His face was very intense as he continued his assault on my vagina. I wanted him to enjoy his orgasm as much as I had mine. I tightened my legs around his, giving him just enough room to slide in and out. I raised my head to his chest and I licked one nipple as I tickled the other with my finger. He screamed, “Janet, I’m cumming now!” and this time his voice was very deep. Wave after wave of his warm semen splashed inside of me and at that moment I was so grateful that I was on the pill. He thrust until he was dry and then just collapsed on top of me. I brushed the hair from his eyes and kissed his forehead and said, “Scott, you were magnificent!” He had the widest smile I had ever seen and he replied, “so were you!”
He laid on top of me for the longest time and I just continued to caress his bare back and ass with my hands. Finally we sat up and my bed was a mess with our cum mixture. I just said, “oh well” and suggested that we take a shower. We enjoyed soaping each other up but nothing sexual happened in the shower. We were both too tired! We dried off and wrapped towels around ourselves and went to kitchen to get something to drink. We sat down at the dining room table and discussed where we were going to go from here. I knew it wouldn’t be right for us to have a relationship and he agreed. But he asked if it would be okay for us to get together from time to time for some fun and I quickly said YES. After all, I had this boy under my roof and now I knew what he was capable of. I told him that he needed to give Katy a call because he had nothing to be ashamed of. I handed him the phone and he made date to take her to the movies the next day. I was so proud of him. I also knew that I was going to be a lot more confident with boys.
Well, Scott and I did make out like rabbits the rest of the day but that was it. He got together with Katy and by the next weekend he was sharing with her everything he learned from me. I was so proud of him. They make a cute couple. As for me, I’m now seeing a boy in my class. We just started dating and he is very shy. Well, now I know how just how to deal with shy boys! We will be alone this weekend and I plan to get my first taste of him then!!