Where it happened: my basement
when I was 14, I lost my virginity to my sisters best friend. Her name was jenny and she was 18. The two of them attended school together since they were kids and now jenny was living with us because of some problems she was having at home. She was a beautiful girl, 5-6, curly brown hair and an hour glass body. I had been in love with her since the first time i met here. Jenny had been living with us for about a month and she made herself right at home, especially when my parents were gone. She would walk around in a tee shirt and panties, showing off her round plump ass and firm tits. She was always the wild one and I wondered what she saw in my conservative sister. One night, I could not sleep so I decided to head downstairs to the kitchen. I could hear some sound coming from the basement, where Jenny was living so I decided to check it out. It was about 1am and I was wearing only my boxers and a tee shirt. I slowly crept down the steps, careful not to make any noise. As soon as the basement came into view, I was amazed to see Jenny sitting on the couch, with only the glare from the TV lighting the room. On TV was one of those soft porn movies that they show late night. Before she moved in, I use to come down to the basement to jerk off after everyone went to bed. As I watched jenny, I could only see the back of her head. I knew she was up to something because I could hear her moan and see her head tossing from side to side. As I tried to sneak further down the stairs, a creek in the floor boards caught her attention. She turned quickly and caught me on the steps.
Without raising her voice, she asked me what I was doing and I told her that I thought she left the TV on so I was coming down to turn it off. I got a better idea she said, why dont you come turn me on. Being only 14, I had never heard a girl speak this way to me. Even though i was a handsome, tall boy for my age, I had never gone any further than feeling a girl up. As i made my way down the steps, she stood up to greet me. she was wearing a tight short tee that clung to her tits, revealing her erect nipples. Her shirt barely covered her legs and I could see from the glare that her thighs were wet. my cock grew hard just looking at her, then she asked me to take a seat on the couch with her. we sat down side by side and talked as we watched the movie. after a few minutes she began touching my leg, then my cock. She asked me if I liked jerking off and if I had ever done it in front of a girl. I told her yes, then no and she told me that she liked seeing boys jerk off for her. while saying this, her hand found its way into my boxers and pulled out my cock. masturbate with me she told me and i began stroking my cock. she then got up from the couch and stood before me. she lifted off her tee, revealing her braless, 34c tits. I storked harder as she caressed her tits and moved her hands down to her panties. as she slid them down i almost exploded. her bush was trimmed to a thin line and her pussy look delicous. She took a seat on the floor before me and spread her legs. her fingers made their way inside her cunt as i continued pumping my cock. as i was about to cum, she told me to stand up. i did and walked over to her. standing between her legs she ordered me to cum on her. i pumped a few more times and let my load fly onto her chest and stomach. she rubbed it in as she moaned, then she asked me if I wanted to expirement with her. i asked her what she had in mind and she told me she wanted me to fuck her ass. the idea had always sounded dirty to me but if i was ever going to lose my virginity, there was no better time than the present. She rose to her knees and began sucking me hard again. it felt so good to feel her warm mouth on my cock. once hard, she positioned herslef on her knees over the couch. I bent down a little bit and slowly eased my wet cock into her tight ass hole. she flinched at first, then began moving her hips side to side as i pumped my dick in and out. i could feel my balls slapping against her wet cunt. after several minutes, she pulled me out and turned over. sitting on the couch, she placed her legs over my shoulder and guided me into her pussy. i didnt last much longer. i fucked her a few good times while squeezing and sucking on her large tits. when i was about to cum she told me to stand on the couch above her. i did as she said and she took my cum into her mouth and swallowed it. she asked that i didnt tell anyone about this and i didnt. we ended up doing it several more times while she lived with us and i got better everytime.