Jenny, My First M/F Masturbation

When I was in high school I dated a girl named Jenny G.  Jenny was two years older than me and had a twin named Julie.  They were know as the G-twins.  Both were petite, small breast, thin, shoulder length blonde hair, blue eyes - very pretty girls.  My parents worked nights, so Jenny would often come over my place.  As teenagers, of course our hormones were racing nearly constantly and after about three weeks our hands finally got under clothes... well my hands got under her shirt.  30 years ago and I can still remember the feel of her soft breasts.  Soon we both progressed with our hands in each other's pants, but neither of us knowing what to do.  This led to a bit of frustration because neither of us could get the other person off. Generally after she would go home, I’d be beating off and finishing in mere moments.

By the time the frustration was getting a bit too much to handle, we had already got to the point where we would get naked before our hands got to business.  Jenny asked me why she wasn't getting me off.  I didn't want her to feel bad, but she needed some lube or something because what she was doing wasn't working.  This is when she asked me what I did when I was alone.  I was a bit embarrassed and tried to say that I didn't know what she meant.  She laughed and said, "come on, everyone masturbates".  I was a bit shocked, but at the same time really aroused because she just admitted that she masturbated as well. Our conversation, while totally naked, turned to masturbation.  I learned that she masturbated almost nightly, and I admitted I masturbated at least daily if not more.  Jenny suggested that we masturbate in front of one another to show each other how we do it. I quickly ran off to the washroom and grabbed a bottle of hand cream and we both sat down on the floor in the living room facing one another. I had her start first because I knew I wouldn’t last very long at all if she started using hand cream. It was an amazing moment for me, her pussy was in full display which was much different in terms of view because we generally laid down side by side when we fooled around. I had only seen a pussy in display like this in a magazine. Jenny didn’t shave her public hair, but she had rather light blonde hair that didn’t really obscure the view. I remember her left hand spreading her lips apart while her right two fingers traced around her clitoris, I just loved the sight of it. She licked her fingers to help get herself wet and immediately I asked if she liked the taste of herself. She admitted she did and that she did it often. My cock couldn’t have been harder. At this point in my life, lesbian pornography was my biggest turn-on and by far the thing I fantasized about more than anything else. Of course my mind went to ‘twin lesbian sex’... but that was not a reality. By now I need to start to rub myself. All I could think about was tasting her pussy. Of course I had smelled my fingers previous nights after she had left, while I finished masturbating (what boy didn’t do this?). But to this point, I had never had a real taste... well at least a taste that was fresh. I asked if I could taste her fingers too. Jenny slipped her finger into her opening, pumped it in and out a couple of times before bringing out the glistening finger covered in what I knew would be a defining moment in my life. She brought it to my lips and I brought my mouth forward for my first genuine taste of a woman. The taste was kind of shocking, I’d never really tasted anything like that in my life. It was slightly tangy, but not at all unpleasant. I loved it! We couldn’t have masturbated much longer before I reached my orgasm. In fact, I didn’t even use the hand cream. My cum shot on to her thigh. She squealed a bit and seemed to really enjoy watching my cock spurt rope after rope on to her.

Although spent, I asked her to continue and watched with intense attention how she used her fingers to caress her clitoris, and then dive two fingers inside. I was even more intrigued when her breathing quickened, and I saw her chest becoming flush. I knew this meant she was going to orgasm. I knew that not all women could orgasm easily, but she obviously knew how to pleasure herself. Her orgasm was so sweet to my young eyes, she moaned and bucked her hips a little until she shook. Her eyes were closed and her face a little contorted. She looked so beautiful. When she finished, she moved on to her knees towards me and kissed me, bringing her wet fingers into the mix of tongues. At this point I was hard again and wanting to do this all over again.

Jenny and I masturbated together every chance we could after that point. When never actually had penetrating sex though. She wanted to, but I was really hesitant... I don’t know why, but I was scared at that point in my, what if she got pregnant? I really can’t explain it now... and somewhat regret that I never got past that point with her. We did engage in oral sex a few times, but masturbation was our thing. Sometimes I would suck on her nipples while she jilled, other times she would have me cum all over her face and chest. I was never able to get her to orgasm using my fingers, but I was very proud the time I made her cum with my mouth... I was a very enthusiastic pussy muncher.

Jenny and I broke up maybe 8 months into our relationship. It was all due to a friend of mine that convinced me to break up with her because bros before hoes was what mattered – stupid, but hey, that’s what we do when we’re young. My time with Jenny set the stage for future exploits that may not have occurred otherwise. Also, my fixation with taste and the love of male and female sexual fluids was firmly cemented into my being due to her. She was the first girl to kiss me with my own cum in her mouth (and I loved it).