This is the true story of my first masturbation with a girl and with a boy.
When I was 13 I had a crush on my girlfriend's older brother. He was dreamy, 16, and had a motorcycle and a popular cheerleader girlfriend. My friend knew I liked him. Sometimes she would tease me about it. Sometimes she would encourage me to go after him. Sometimes she would be jealous of my attraction. He just ignored me.
She and I talked about boys and sex a lot. We also masturbated together in her bed room or in their basement just about every time we got together. I realized then that I was both a voyeur and an exhibitionist.
This was before the Internet. We would take her brother's porn magazines, Hustler, Penthouse, and Oui, look at them until we were horny, and then push our shorts or pants and panties down and go at it together. I think she enjoyed looking at my pussy more than I did looking at hers. She even suggested we eat each other out. I was afraid of that, although we did finger each other a few times. But I was fascinated by how she masturbated. She would sit back on one hand and fuck her or my fingers, biting her lip, grunting, bucking her hips into her or my hand, and opening and closing her knees. She would also talk dirty, saying 'fuck me' or 'God, eat me out' or 'that's it, do me.' When I masturbated I just spread my knees, sat back, rubbed my clit, and put a finger or two inside my pussy. I also liked to touch my nipples, ass, and asshole. Mostly, I thought about her brother and how I was looking at the same pictures he looked at when he jerked off. That, along with seeing all those pussies and penises, is what really turned me on. Once when we saw two pages stuck together she told me that it was because of his cum. I nearly came hearing that.
Once, when we were really masturbating up a storm, my friend asked me what I was thinking about. We were both near orgasm. I told her I was thinking about sucking her brother's cock. She moaned and came, saying that she bet I wanted his cock inside me, and that she had seen it once when he was masturbating and it was huge. I came, confessing that I was thinking about him fucking me. I pushed her for the details of her catching him masturbating and she told me how nice and hard he had been, lying on his bed, and that he used hand lotion and grunted when he came. That was enough to make me have to masturbate again while she watched.
I have read on here about guys sniffing or licking a girl's panties. I know my boyfriend likes to do that. He claims that he used to steal his own sister's panties and sniff them when he masturbated. I can relate to this. A couple of times my friend and I borrowed her brother's jockstrap or his underwear. We once both sniffed his jockstrap and laughed. I wanted to do more. I wanted to taste the pouch that held his penis. But she always took the underwear back before I had a chance to do anything more.
One summer afternoon her brother caught us masturbating with his magazines. When he walked in on us, I had already lifted my skirt, spread my knees, and had started touching my pussy. My panties were off. This left my pussy totally exposed to him. My friend was nude from the waist down and her hand was busy between her legs. We were both totally absorbed with the sexy pictures and with rubbing our horny young pussies. He just stood there in the doorway watching us for I don't know how long before she noticed him. She said 'Oh, my God!' He came over and picked up the magazines and told us angrily to stay out of his room. He was visibly shaking. I thought then it was because he was angry but I now think it was because he was turned on. I froze. Before I had a chance to close my legs, he was standing directly over me. I knew that he had been staring directly at my open, wet pussy. This simultaneously shamed me and gave me a huge sexual thrill. No boy had ever seen me nude before. He stood there looking down on our bodies. He told his sister we were going to be in so much trouble. Then he left. He slammed the door to his room and we were freaking out. She got dressed and suggested we get as far away from the house as possible. Knowing that he had seen me like that, I was more horny than afraid. I needed to cum really bad. I told her I was going to the bathroom and that I would be out soon.
I was headed for the bathroom to finish masturbating when I passed his door. I felt very powerful and horny. Instead, I went to his room and knocked. I was still holding my panties in my hand. He opened the door and I told him I was sorry. He had calmed down and said it was OK. His shirt was undone and his pants were unbuttoned. I wondered if he had been masturbating. He said that it was just that he didn't want us in his room, especially in his private stuff. He saw the panties in my hand. He smiled and he apologized for screaming at us. Then he asked me if I wanted a ride on his motorcycle. This was a first. I said yes. I went to the bathroom and put on my panties. He got me a helmet and we told his sister that I was going for a ride. She did not know what to think. He told me to hold on tight. I wrapped my hands around his waist and we took off.
The combination of the speed, holding him, smelling him, and the vibration of the ride had my panties soaked in an instant. My panties and pussy were pressed against his tight butt. I instinctively began rubbing my pussy against him. He pressed back. Then he pulled off into a grove of trees near their house. As soon as we stopped, we got off the motorcycle. He asked me if his sister and I played with our cunts often. I had never heard a boy call it 'cunt' before. I thought it was very dirty and sexy. I told him 'sometimes.' He asked me if I was still horny. I said 'a little.' He said he liked watching me play with my cunt. He told me that he wanted me to finger myself in front of him, like I was doing with the magazines, and that if I did it he would show me his cock and he would not tell his parents what we were doing.
I did not hesitate. I lifted my skirt. Then I sat down on a fallen log and spread my legs for him. I began to stroke my slit outside my panties. He began squeezing his cock in his pants and told me to remove my panties. I did. He told me to spread my legs for him. I did. Then he told me to stand up, bend over, and let him see my butt. I did this too. He told me I had a nice ass for a seventh-grader. He had me spread my ass cheeks for him so that he could see my asshole. He stroked me there, touching me everywhere. He stroked my ass crack and my pussy. Then he told me to sit back down and 'Touch your cunt.' When I turned around, I saw that he had taken out his hard cock. I was going mad and I fingered my pussy openly for him. He pulled his cock and stood over me. He began stroking faster and harder. He reached down and put two fingers inside my pussy and finger-fucked me, as I rubbed my clit. It was amazing. I stood up and kissed him on the lips but he told me to sit back down. We resumed our fingering and stroking.
He told me to show him my tits and to open my mouth. I lifted my shirt and bra. He touched my nipples. Then he put his fingers back inside my cunt and the head of his penis just over my open mouth. He told me to tell him when I was going to cum. I thought he wanted me to kiss it. I wanted to suck his penis but I just did what he told me. I put my hand back to hold me up and I was fucking his fingers, lifting my butt up to him, just like his sister did when she masturbated. I then understood why she bucked her hips so hard. I told him I was cumming. He said 'me too'. Then he came hard and long on the side of my mouth, stream after stream. The combination of tasting his salty cum, being fingered, and exposing myself like that gave me the most intense orgasm I have had before or since. He said, 'Don't get any ideas because I have a girlfriend.' He told me not to tell his sister or anyone else or he would tell everyone at school I had fucked him and that I was a whore. I was both elated and crestfallen. We rode back in silence.
He dropped me at their house and rode off. I told his sister that we had just gone for a ride around the neighborhood. She wanted to know if we were in trouble. I said that I didn't think so. She suggested that we go back inside and finish masturbating. I was still horny and had another explosive orgasm in her bedroom.
I kept the secret, not only because I did not want a bad reputation in high school but also because I did not want to share it with anyone, especially his sister. Basically, he completely ignored me after that. I was not surprised. A couple of times he pulled me aside when his sister was out of sight and groped at my pussy, tits, or ass, reminding me that I was his slut. I got great thrills out of this, despite the emotional confusion. I actually looked forward to his slipping his fingers inside my panties out of the blue. I enjoyed the naughty thrill, letting him do to me whatever he wanted whenever he wanted. Secretly I wanted him to take me to his room and fuck me. But it never happened. This groping didn't last but for a few months. In retrospect, I know that he was a jerk, but he gave me one great afternoon. Thanks for listening.