When I was about sixteen, I had led a pretty sheltered sexual life. I dated some, but had never gone further than some mutual masturbation with my 'girlfriends'. I had a step-sister, Jennifer (Jen) who was about a year and a half older than me, who, even to say for a sister, had a 'smokin' body. She was really hot, and had no shortness of dates or boyfriends. We were always very open with each other from an early age, (our parents married when we were very young) and seen each other naked many times. Often times at the beach if she was not with a boyfriend, we would play and wrestle in the water, but nothing further ever happened.
One night, after a pitiful date with a girlfriend, I was pretty down when I came in the house. Our parents were out, and Jen asked if everything was OK. I said not really, and that I was going to bed. Jen said if I wanted to talk, she would listen.
It was such a horrible night, I decided to spill my guts. I told Jen that we had got into a makeout session in my car, and that we started to 'mess around' but my girlfriend got really frustrated with me and stopped me from doing anything. Jen asked what we had done, and I plainly told her that I started to finger Maria (my date) and she had taken my penis out of my pants and started to jerk me off, and it hurt. Jen asked me why Maria wanted me to stop, and I told her Maria said I just didn't know how to 'jill off' a girl. Maria said she was dry, and I didn't know what I was doing, so to stop because she didn't like it.
Jen said I needed to know a lot more about girls, but that it wasn't my fault. I asked her what she meant, and she said that once, just once, with some ground rules, if I didn't tell anyone, she would show me what feels good to a girl, and what a girl likes. I asked her what she meant, and she said that 1) there would be no open mouth kissing, 2) there would be no oral sex, and 3) there would be NO intercourse - ever. I agreed.
Jen asked me to go into the hallway for a minute while she changed. I did, and a couple of minutes later, she called me into her bedroom. I entered, and she was lying, fully clothed on her bed. She asked me to lie down beside her, which I did. Jen said 'Now, time for your lesson in 'girl 101'.
Jen asked me to treat her just like Maria, and to do what I did with her. I asked if she was really OK with this, and she said absolutely. I put my face in her neck, (remember, no kissing rule) and I immediately started to pull at Jen's sweater. Jen told me that a girl likes to be cuddled before the groping starts, and that I should just hold and stroke her non-sexual side first. I did that for a few minutes, and Jen started to moan. She said now it's time to carry it a little further. She sat up in bed and told me to take off her sweater, exposing a beautiful dark blue lacy bra. I put my hand on her jeans, near her vagina, and she said 'What did I just tell you, play first.' So for a few minutes, I started to massage her sides, and then her breasts over her bra, and again she started to moan. She sat up and unsnapped her bra letting it fall to the bed. She had the most beautiful tits I had ever seen!!! She said that was good, and now we could start to go further again. All this time I was fully clothed, but had the biggest erection I had ever had. I thought I was going to shoot my load right then and there!! I asked her if I could get undressed and she said to wait, it will make it better later. Jen told me to unbuckle her jeans, and slide them off her. I did that to reveal a pair of lace bikini panties which matched her bra. Jen then slid my shirt off, and gently kissed my nipples. She unsnapped my jeans, and pushed me back on the bed, sliding them off me. I had on a pair of bikini briefs, which hugged my erection, and Jen said made me look soooooo hot. Jen laid back down, and I put one hand on her breast, and one under her panties. Jen pulled it out and said that I should just stroke her over them for a minute. When she was ready, she took my hand and put it under her waistband. I thought that was the go ahead, so I tried to finger her right there.
Jen said that is where I had gone wrong with Maria, that a girl needs to be really wet first.
Jen put her hand over mine and showed me how to stroke her pussy, and her clit. A few minutes later, she said 'Now, here, feel the difference?' and slipped my finger into her wet, hot, waiting vagina. I could not believe how different it felt!!!! It was moist, and warm, and my finger slipped right in. With her hand over mine, I masturbated her for three or four minutes, when she started to wince, and arch her back, she told me she was going to cum. (something I had never had happen with my girlfriends.) I felt her vagina clench around my finger, and spasm when she came. She did that for about 30 seconds, and pulled my hand away.
Jen rolled over on her side and said that it looked like something else needed attention, and pointed to my erection under my briefs. I know I turned bright red, but said yes, 'He' needs some relief too, are you OK with that? Jen said she could do what she does with her boyfriends, and I said go ahead, I am yours. Jen slowly rubbed my erection through my briefs for a minute or two, and then slipped her fingers under both sides of my waistband and slipped them down off me. She took my penis in her hands, slowly stroking it, and asked if that felt good. I could only moan at that point, but said to be careful, because the last time my girlfriend jerked me off, she rubbed the head too hard and it hurt.
Jen asked if she ever used 'lube' and I said no. Jen pulled a tube of lube from her nightstand, and poured some over my cock. She proceeded to rub it over my cock and balls, grabbed my cock and stroked me off to the slickest BEST ever cum in my sixteen years. Just before I came she told me 'I can see you're getting close, I can feel your cock swell in my hand, cum for me Kyle, I want you to cum in my hand.
I had the BEST orgasm of my life so far with my step-sister.
That afternoon, I learned more about girls than I ever had in the past, and would never had known without Jen's help. I thank Jen for her help and instruction. Since then, I have been told I am one of the best lovers my girlfriends have ever had. I had even been with Maria after that and it was INCREDIBLE.
Needless to say, Jen and I had been together a few times after that, but she has moved on to marry, and raise a beautiful family. When I see her husband, I am a little envious, because I know he must have an outstanding sex life with Jen.