My First Penis

As a reminder, I was pretty clueless about sex when I was a teen. My parents (more specifically, my mother) never really discussed anything more than the very fundamental mechanics of it, emphasizing the myriad negative consequences for failing to be a “good” girl and having anything to do with a dirty pee-pee tail. I didn’t have an older sister to let me in on the secret, and my few friends were too shy to talk about it or were just as clueless as me. I had to learn about sex via “on-the-job” training.

I scored my first boyfriend when I was 15. I kept him a secret from my family, and only saw him at school or talked to him on the phone when no one was around at home. I was in “love” and we even went so far as to hold hands. I had my first kiss in front of the school while waiting for the late bus on a drizzling spring day. Our torrid romance lasted a whole three months before I got dumped (he told one of my friends to tell me it was over and that we could still be friends).

Once I’d known the joys of having a boyfriend, I was eager to find another despite the heartbreak (which, to be honest, wasn’t as bad as I thought it would be). Danny and I sat next to each other in French class and so we were often paired up for conversation practice – which we were both awful at. He was a nice guy, but I hadn’t considered him as boyfriend material until he asked me out on a real date out of the blue one day. I was sixteen by this time, but the rule was no dating until I was at least 17 (although, if it were up to my dad, it would have been 27). It took a couple fights with mom and dad, but there was a negotiated settlement that I could go out with him if it was a group date.

After that night, we were a thing. There was hand-holding and kissing – all the possibilities when it came to physical love. At least that’s what I thought up until he touched my boob.

We were making out in the last row of the darkened movie theater. We sat back to take a break, his arm draped around my shoulder. Minutes later I felt him shifting. I thought we were going to resume sucking face, but then his hand was there, on my boob, cupping me through my bra and sweater. Panic mode. What was I supposed to do? Slap him? Run away? Call the police? He began squeezing while I ran through my options. I wasn’t supposed to let boys touch me like that, but the problem was that it felt good. Really good!

I didn’t stop him. Furthermore, I hoped he wouldn’t stop. There was more kissing and more chest groping and it was perfectly delightful. So much better than holding hands! Adding my tits into the mix really fired up our relationship for the next couple weeks. We quickly advanced to under-the-shirt/over-the-bra action. Without my mom knowing, I bought myself a bra with a clasp in the front. This provided easy access the next time I saw Danny and he was thrilled to finally get his hands on my bare breasts. His palms were a bit sweaty, but I didn’t care. How could my sex life get any better? That’s about the stage that he gently took my hand and placed it on his crotch.

There was something there. Something long and hard. I knew about penises, and had an abstract notion of erections, but this was something else! I wasn’t sure what to do (or not do), so I just squeezed it the way he did with my boobs. He seemed fairly happy with that, so I figured I was on the right track. Cut to his friend’s house. Brian and Kelly were in the family room making out; Danny and I were in the less-comfortable but private formal living room doing the same. My bra was undone and my shirt pushed up. I was massaging his hard-on through his jeans when he leaned back, unzipped his pants, and pulled it out. Whoa, Daddy!

Sure, I’d been curious, but I wasn’t going to be the one to make that move, or even ask for it. But, as it turned out, I didn’t have to. There it was, my first penis…in the flesh.

It was circumcised (as have been all the penises I’ve been given access to). Looking back, I’d estimate it to be in the neighborhood of 6½ inches. A nice upward curve. Super hard and literally pulsing. I wasn’t introduced to his balls on this occasion, but I was mesmerized. The thing that most surprised me were the veins. That scared me a little. I was expecting the shaft to be smooth – at least that’s what it looked like in the drawing I saw during Sex Ed! I instinctively wrapped my hand around it and our kissing resumed with a renewed passion.

He began kind of humping up and down, which gave me the clue that I needed to be doing something more than just squeezing it. I began stroking and earned a happy moan from him. I wonder if my palms were sweaty…

Before we could get too far, the phone rang. Someone was on the way home, so we all had to cease and desist and head out to the trampoline like that’s what we’d been doing the whole time. Everyone was left frustrated. Danny’s naked cock was all I could think about that night as I lay in bed. I was in one of those times where I was trying to convince myself I shouldn’t masturbate, especially since I had a boyfriend to “satisfy” me, but my will-power had been pushed beyond the limit. I found myself facedown and grinding my mattress. After a few minutes of this I gave in, rolled over, and shoved my hand down into my PJs. I frigged my pussy to a great orgasm. Once I’d violated my promise not to touch myself, there was no further point to not fingering myself. I made myself cum twice more that night, then renewed my promise not to be such a perverted freak from then on.

After seeing Danny’s penis, my perception of sex shifted. I honestly hadn’t considered the cock in much depth before that day, but it had suddenly become a central focus for me. I was fascinated with it. It was like this alien creature living in my boyfriend’s pants. It was so strange, and frightening, and irresistible all at the same time. I loved the way it felt in my hand. The skin was soft and moved in my grip like nothing else did. I came to realize the veins that had put me off at first actually gave it more personality – it would look too weird if it was just smooth skin. I adored his cockhead. The shape, the color, and it’s soft squishiness. The pee-hole was so cute. I tried not to think about it, but as soon as I saw it, I wanted to see what it would like pissing. Gross – what was wrong with me? Or, so I worried at the time. The cock was an amazing thing all on its own, but then the bizarre fact that it was supposed to go into my vagina was almost too much for me to get my brain around.

The next chance we had to be alone was while we were out for a walk. We ducked into the woods. Tits and dick were out in a flash and we picked up right where we left off. It wasn’t long before he was moaning and going crazy. Then all of the sudden he relaxed. I wasn’t sure why, then realized there was something gooey on my hand and all over his T-shirt. I’d made him cum! And I missed it!

Nonetheless, I was pretty proud of myself. I had the power! I was one sexy lady. I could make a guy cum. And everyone knows how difficult that is!

After a couple more such handjobs, I arrange things so he was lying out flat and I was sitting up jacking him off in a way that I would be able to see the whole thing. This actually happened in school, after hours, in a quiet study room of the library. There was a risk of getting caught by one of the custodians, but we were too horny to care. I squealed when I saw the jizz shoot from his cock. I couldn’t believe how far it went or how much there was. That’s probably when my real love affair with cum began.

Things naturally progressed from there. He got into my pants and fingered me. Danny convinced me it would be okay for me to suck his penis, and it was. It really, really was. He never really went down on me. I was a little freaked out by the idea of it, but he did go down there and kiss around a few times. It felt nice, but it stressed me out. When he broke the news to me that his family was moving away in August, I learned what heartbreak felt like for real. It was the following week that I lost my virginity.

There were a couple letters once he’d gone away, and one long-distance phone call, but then we both just sorta moved on. He was a good boyfriend and he opened up a whole new world to me. I finally had an inkling of what real sex was, and how wonderful it could be. I thought I knew it all at that point, but little did I know there was still so much more to learn. But, no matter what else happens in my sex life, Danny’s will always be my very first penis.

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Cumming soon: Open Door Policy 27…

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12 thoughts on “My First Penis

  1. Sweet story my first feels and loss of virginity were with my girlfriend at the time who had the unfortunate nickname of Missy Mouse due to both her real name which I’d rather not give and her height. She was and still is I suppose 4′ 11″ and 1/4 “. I remember the quarter inch was very important too her as it put her over 4’11” even and she was a quarter inch too short for the navy. I’ve often wondered what happened to her since we lost touch.

  2. Thank you for sharing, Rach. First times for anything are stressful, but fun to reminisce over. My introduction to the wonders of the female of the species came as a result of a high school dance. A good friend had broken up with his girl, so I stepped in. Jane was a petite, but very adventurous girl. When we danced, she had one hand draped around my neck and the other pressing against my raging hard-on. Afterward, she convinced me not to take her home, but, rather, park three houses down from her house, where we made out for quite some time. She taught me the ‘art’ of sloppy-wet kissing as well as one-handed bra removal. Shortly after feeling the warmth of her small pointed breast, she delved into my pants, making a glorious mess in my boxers. Before we could agree on another date, she re-united with Bill, and my sex-ed was put on hold until college, where I met my first wife and lost my virginity on my living room floor, with my parents upstairs.

  3. Loved it, the innocence of our youth, the first fumblings in a movie theatre (back row, double seat), the smooth thighs under her skirt with her legs gently parting and the response as I first touch her panties; lying in a field gradually removing our clothes, touching, exposing breasts and cock; finding time at home when our parents were out, and frantically getting dressed when they returned unexpectedly.

    So many memories………

  4. Great story, so much better than my first vagina. LOL

    How cool would it be if the Danny is a fan and reads this and realizes that he was the first and may have contributed to what turned out to be a very sexy and Dirty Minded Mom.

  5. Great story Rachael! Remembering back to those early “make out” sessions, it seems they went on for hours. Most of mine occurred in cars. The sexual tension was almost unbearable. My underwear were always an absolute mess by the time we were done.

  6. @…: That does sound quite ridiculous, I agree! Please point me to the passage where I claimed I didn’t know what an erection was at 16 and I’ll take it out. I don’t remember writing anything of the sort, so if I did I need to fix it immediately. I feel so embarrassed for making such a mistake regarding my own experience. And, of course, it must be my mistake because it couldn’t be that you were careless and misread. Crikey…

  7. What a lucky lad Danny was… good for him!

    And as to you, Rachael, as always, you have the gift of being inherently impossible to write anything that’s not erotic and/or interesting.

    Your fiction is smokin’ hawt, but your true life stories — both past and present — are a joy to read!

  8. I wouldn’t get too hung up about an erect 16 yeAr old penis if I were you Rach.
    Far too much good stuff in there; sure most readers never noticed, or if they did, just ignored it!!

  9. Yes! I love it when Rachael tells us of her experiences! It makes all of her fiction even better! Thank you, Rachael. I’d been away for a few weeks and loved what I found when I returned!

  10. Rach

    Loved this story. I remember my petting time with my then gf, now wife. We played tons never “going all the way” but plenty of wet kissing and hand time.

    Thanks for sharing. Hugs.

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