My First Time [FM]

This is an old story. I’ve been having sex for 27 years now, which is longer than many of you have even been alive! Something I read here recently, though, made me remember the story of my first time.

I have always been sexual.

Seriously, I have masturbated to orgasm for as long as I can remember. I was like 4 or 5 when I start having memories of my parents telling me to stop “playing with myself.” Eventually, I figured out that this is something that I shouldn’t do around the parents. I tried to wank in bed, but I shared a bed with my sister, and she got pissed about me “shaking the bed.” There just wasn’t a lot of privacy, so I had to get creative.

I discovered my dad’s porn stash when I was, oh, 7? Hustler, Playboy, and the Longarm books, which were basically erotica written for men, with all the smuttiness and crudeness that entails.

Flash forward to 17.

My mom wouldn’t let me date. So, my older sister did what cool older sisters have done since maybe the dawn of time. She helped me sneak out. Her best friend in the world was a guy named Matt. Matt’s younger brother was named Sean. I’d had a crush on Sean for years. In a pattern that was to repeat itself over and over again through the years, he’d always been into my best friend.

In another pattern which was to repeat itself, I went after him anyway, and eventually got him. Kinda.

I so wanted him to be my first. I’d already been on the pill for a year, “for my acne and my cramps,” I told my mother. It was technically true, but what a relief to know that I could have sex without getting knocked up!!! Anyway, my sister and I were leaving Matt and Sean’s house one night after a conversation in which I just happened to let it slip that I’d never been kissed. We were pulling away when Sean knocked on the window. I rolled it down, and he leaned in and kissed me.

He stood up, looking surprised.

“Damn!” he muttered, leaning down again. His lips were full, sensual. He tasted of whiskey, cigarettes, with just a hint of something minty. For an endless moment, our tongues eagerly explored each other. My sister’s laughter broke the spell. Thus began a long, hot summer full of sexual explorations … only without the sex. Every time we got close, we’d get interrupted. I mean every time.

Fuck!

I moved away shortly after I turned 18, and that was that for Sean.

Over the next year and a half, I played with guys, mostly for practice, but there was no one who I really wanted.

Until Rick.

I met him in the mosh pit at a punk show, where I was the only girl in there mixing it up. I noticed him early on. He was gorgeous — bright blue eyes, tousled blond hair, and he was tall, with a lean, well-knit body. We shouted our names at each other, he bought me drinks since I didn’t yet have a fake id, and we moshed. I lost track of him after the show and was bummed! As I walked down the street towards my car I miraculously heard my name through the ringing in my ears. Yay! It was him! We exchanged numbers and a really hot kiss.

Turns out, he was a lot of fun to be around. He was in the military, young, hot, laid back, and very honest about wanting to keep things casual. “Fine with me!” I assured him, being that I had just started college and was ready to spread my wings a bit. Even then, with my limited experience, I knew his cock was truly huge. In fact, his is still the very biggest I’ve ever seen up close and personal. It was 10-1/2″ long, and thick, too! After a few weeks of casual dating and really great mutual oral, etc., I made a Really Big Decision.

I told him that I wanted him to be my first.

He declined.

He declined!

He declined??? Really???

He didn’t want “the responsibility” of being the first the fuck me, and he was worried that I’d fall in love.

I can’t tell you how disappointed I was, not to mention stunned. Everything I’d always heard about men was suddenly suspect. I tried to explain that I wouldn’t freak out on him, I told him I was on the pill, I told him how ready I was to have sex, but it was to no avail. He said that we could still fool around if I wanted, but he wouldn’t budge on the “no sex” thing.

Fuck!

In the meantime, my college roommate set me up on a blind date with her boyfriend’s friend, George. I wasn’t immediately attracted to him, but went out together for a while (but that’s another story).

I saw him a few more times, he grew on me. He was a very talented musician and sarcastic as hell. That’s kinda hot, I thought. We made out. He told me he was a virgin (I later found out that he lied). He also told me that he didn’t really believe in sex before marriage.

What???

Fuck!!!

I left my religion of origin, and I was ready to obliterate every trace of the good girl my mama wanted me to be. For a while there, I thought about walking around campus wearing nothing but a sandwich sign that said, “BREAK MY HYMEN — ASK ME HOW!” I never thought virginity would be so gawd-damned difficult to get rid of! I thought about lying to Rick and telling him that I’d done it, but I wasn’t sure that I wouldn’t bleed. I wanted him so badly I couldn’t stand it.

So, the gropings with both Rick and George continued. I was starting to be a little obsessed. Everyone else I met with whom I felt sparks was dating a friend, and I had literally no idea at that point how to hit on a guy. I was constantly thinking about sex. I yearned for it, and I literally couldn’t believe my bad luck.

I turned 20 over Winter Break. Finally, New Year’s Eve rolled around. George and I had my dorm room to ourselves. We fooled around for hours, so much so that I was a little numb. Then, I lost my virginity. And I do mean I lost it … I didn’t even feel him slide into me! He said, “I think I’m inside you,” and that was pretty much it. He came. I took him home.

I felt cheated. After all these years of waiting, it was hard not to feel let down. I checked my sheets when I got home. No blood. Not a drop. Still, for what it was worth, I thought, I was part of it now. Part of life. Part of the long history of womanhood on this planet. It was the first time I ever really felt connected to myself as a woman.

The next day, I called Rick up and arranged for a meeting. When I got him into his bedroom, I got down on my knees, took his dick out, and got him hard. I stopped and looked into his eyes, smiling.

“I’m no longer a virgin,” I said.

I so distinctly remember this flash in his eyes, and then he said, “Well then come here!” and he pulled me onto the bed and kissed me, slow and hard. He undressed me in a flash and touched my clit. I was so wet! He got me off with his hands, and then he teased my pussy with the head of his cock, and I stopped breathing. He slid into me, just a bit, and waited. I pushed against him. I wanted more. He slid into me a bit further, and there was some resistance. Even though I was wet, it didn’t feel smooth. The feeling, though! I needed to feel more of him. I remember squeezing him tight, as if I was trying to suck him into me.

Very slowly, he started sliding in and out, and I felt for the first time how it feels when my pussy lengthens. To this day, sometimes that feeling surprises me. I felt stretched. Overwhelmed. I couldn’t believe that this was finally happening. I wanted to look him, but I couldn’t. I was too shy. I ran my hands slowly down his back and clung to him while I was getting used to the feeling of him slowly thrusting into me. Something about him always smelled like sunshine, and I breathed in his scent and started to relax a bit and slowly, my trembling slowed.

I risked a glance at him, and he was, well, there was no other word for it, *smirking* at me. I slammed my eyes shut and he suddenly thrust once, really hard and really deep, and stopped. I inhaled deeply in surprise, and a moan escaped my lips. Slowly, he picked up the pace, and it felt so good, I started to move with him. I’m sure I was clumsy, but he was so great to me. He grabbed a handful of my hair and pulled and fucked me harder. I couldn’t believe how amazing it felt to be filled completely. Slowly, I moved my legs and wrapped them around his ass, wincing because it hurt, and then immediately trying to pull him deeper into me. He was as deep into me as he could go, but I wanted more. I felt like such a greedy slut, having two men inside me in less than a day, even though the first one barely counted. Of course, I couldn’t know then how common this would be for me. After I figured out myself a bit, I structured my entire life to make it possible.

He went harder and growled into my ear, “Were you thinking about this the whole time you were fucking that other guy?”

“Yes,” I lied. I mean, it wasn’t technically true, the sex hadn’t lasted long enough, but I always knew that I’d go back for Rick once that pesky virginity was out of the way. And now, it was happening!

And that question? It turned me on so much that I felt my orgasm building. And I felt something pass through his body, this rolling energy that sent me over the edge. My pussy spasmed, and I came, and it was amazing to me. I came again, and then so did he, and I couldn’t believe how good it felt, being filled by him.

I was hooked.

I got the giggles, but I couldn’t tell him why. I felt super shy suddenly, but it wasn’t long before he pulled me back to him, his cock throbbing back to life. I think we fucked three times that night.

I was sore for days.

Source: reddit.com/r/gonewildstories/comments/eufw41/my_first_time_fm